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Jesse Middleton

Jesse Middleton is, at his core, a problem solver. Early in his career, he used this ability, in addition to his natural curiosity of the internet, to found and “pivot” several companies. Ultimately, his trial and error  of his businesses lead him to partner with the then-budding coworking space, WeWork, adding to their suite of offerings as co-founder of WeWork labs. However, as the company grew exponentially, so did Jesse’s role, and in that growth,opportunity struck again. Now, as a VC at Flybridge, he uses his valuable problem solving skills along with the knowledge he’s gained as an operator to invest in and advise the companies seeking his support. Over dirty martinis, he explains the key characteristics that have helped his career thrive: the importance of a familial atmosphere when approaching business, overcoming the obstacles of being an introvert, and through it all, why every major decision he’s made ultimately comes down to what feels right.

What You’ll Learn

- Why being suspended from school is not always a bad thing

- How transparency with your investors is core to your relationship

- How problem solving is a unique skill in and of itself – especially for operators

Jocelyn Leavitt

While Jocelyn Leavitt has had a clear goal throughout her academic and professional career – to make education more accessible – her path to achieving it has been anything but. The spark was ignited while she was majoring in geography at Dartmouth, however, since then she’s spent her time teaching the underprivileged in Hawaii and New York, earning an MBA from Columbia University, pursuing a path in private equity and real estate before ultimately starting in the software space. It’s this varied experience and drive to bring inclusivity to the tech world that’s given her a unique set of skills suited to create Hopscotch – the only application optimized to build and consume apps exclusively on mobile. Over micheladas from ABC Beer Company, she describes their growth since launching in 2013, and the success in continuing to inspire kids ages 9-12 in their early stages of programming to create and play games and hopefully start a lifelong love of making.

About this episode:

- Why not having a technical background shouldn’t deter anyone from innovating within the space

- The differences in the startup and tech scenes in New York versus San Francisco

- How computer science can and should influence younger generations

Nihal Mehta

Nihal Mehta has been investing in the mobile space for the last 15 years, long before he became General Partner of Eniac Ventures. In fact, he started his career founding one of the earliest mobile ad products, long before the smartphones and ad buys we know today. In those early days he invested his time and effort chipping away at the potential the mobile space offered. After seeing many successes and failures as a multi-company founder, exits to companies like Omnicom and Google, and the evolution of technology and honing his expertise, he now spends his days advising companies with founders who share his passion for the industry. Over Pinot Noir he explains what inspired him to get started in this, then, largely uncharted territory and how his experience as a founder makes him uniquely qualified to invest today.

What You’ll Learn:
- What early stage companies should do before they raise
- Why former founders make optimal VC partners
- How investing in early technologies can pay off

Elizabeth Green

It’s been said that “knowledge is power” and no one embraces that more than Elizabeth Green. She has dedicated her life and career to bringing information to the masses in the hopes of bettering the US education system. Over Campari and Soda provided by Alphabet City Wine Company, she remembers very distinctly the moment in highschool when she realized the educational inequities amongst her own group of friends. From then on she was compelled to a path of journalism – with the aspiration of shedding a light on this increasingly complicated industry. However, when the traditional newsroom fell short in it’s support of the coverage she felt so passionately about, Elizabeth took matters into her own hands to create a publication that would cover it correctly. Now, as the cofounder and CEO of Chalkbeat, a nonprofit education news organization with the goal of keeping regional educators abreast of policy within their industry, she faces a new set of obstacles. All this while still finding the time to continue to be a thought leader in the community and writing a New York Times Book Review Notable Book: “Building a Better Teacher: How Teaching Works (and How to Teach it to Everyone)”

What You’ll Learn:

- How and when journalism can effect real change

- As a founder: the importance of empowering a team to put their best work forward

- The anxieties of being a startup founder and business owner at different stages of her company’s lifecycle

Rob Markman

Rob Markman is the storyteller’s storyteller. Growing up in the in the heart of the cultural epicenter that was Brooklyn in the 80s & 90s, during the birth of rap music, he was hooked on to the genre early on. However, when his friends’ interests halted at memorizing the lyrics to Slick Rick or Kris Kross, he dug deeper. As he continued to mature, he did so alongside the music, eventually taking a chance on open mic nights and battling in lower Manhattan. Over Hennessey and Cokes, he tells us that at the core of this obsession has always been clear: to change the culture of how we talk about music and his innate drive to investigate the meaning and influence of each track in an encyclopedic manner. It makes sense then that as he entered into the professional world “journalism chose him” and he made a name for himself in the industry as Senior Hip-Hop editor for MTV (and also noted as one of BK Mag’s Most Influential 100). Now, as Artist Relations Manager at Genius, he’s even closer to realizing his goals than ever before, bridging the gap between artists and fans and helping to bring the heart of the story back to the forefront of the conversation.

What You’ll Learn:

- The pros and cons of technology’s influence on the music industry.

- How your passion can become your career in ways you may not have expected.

- Why in a creative industry, the true star should be the work and not necessarily the artist.

Photo credit: Daniel Dorsa

Maddy Maxey

Maddy Maxey boasts a career path that spans a variety roles and industries – from Tommy Hilfiger to General Assembly she has covered the fashion and technology realms with fluidity and ease, and at 23, it’s only just the beginning. It’s a background that has not only returned high recognition like being listed as one of Forbes 30 Under 30, but has also  provided her the experience to recognize and carve out a unique intersection of the two industries – and led to the founding of her company, the Crated. Focusing on cutting-edge innovation, her company collaborates with others in the space to further the offering of wearable tech, and most specifically, smart fabrics. Over tempranillo provided by Alphabet City Wine Co. she gives us the fascinating perspective of how she was able to be a trailblazer in this industry, especially with the challenges of it being in its infancy, why not being popular in high school was ultimately a good thing, and that, above all else, being a maker is her single greatest motivator.

What You’ll Learn:

- How sometimes a hands-on education is better than following a university curriculum.

- Why it takes a certain personality to start a business.

- How to make the most of resources in the early stages of an industry.

Andy Ellwood

Andy Ellwood started his first company at the age of 12 – a lawn care business unlike your typical teen gig – one that stayed in the family, and passed from brother to brother for 19 years. That experience, paired with his focus on finance at Texas A&M, has set his course as an expert salesman since, with an emphasis on his unique ability to make a sale, regardless of the product. That’s why, when making the leap from his home state of Texas to New York City with no job prospects, his best friend of several decades knew he would excel as the biz dev lead for his budding tech company, Gowalla (even if Andy didn’t know what “biz dev” meant. Or API. Or anything about tech, really.) It’s a decision that has lead him further down the path of technology, ultimately leading to his latest venture offering major savings to offline shoppers: Basket. Over bottles Shiner Bock, Andy shared his milestone experiences: how a tough professor steered him into finance, the continued benefits of being an Aggie, and his theory for how he avoided a Texas accent.

What You’ll Learn:

- How your competition can be a great motivator.

- Why sometimes confidence that you’ll learn on the job is all the experience you need.

- What distance you’ll travel to save $10.

Allison Goldberg & Jen Jamula

Alli Goldberg and Jen Jamula have made a career out of coaching people to face their greatest fear; public speaking. It’s a position they ended up in almost by happenstance. As Yale University theater grads, these ladies set out as many post-graduation students do, subsidizing their passion for acting with jobs they found less than fulfilling. However, when the pursuit of theater also left them wanting, a chance reunion gave them the spark for an idea – creating their own kind of theater using the Internet’s greatest content as the script of their production, Blogologues. And as that legitimized, so did the requests for coaching as well. By way of a shared office space, Alli and Jen became some of the more popular folks around the water cooler, where budding entrepreneurs pined for assistance in crafting and telling their stories. Over Rebel Yell Small Batch Reserve Bourbon compliments of Fool’s Gold, the Blogologues and GoldJam founders tell how they evolved at every turn, ultimately turning their speaking advice into tailored workshops for companies large and small, and their quest as faux tech people to reestablish verbal communication (by starting the no text weekend).

What you’ll learn:
- Why public speaking skills matter, even if you think you don’t need them.
- The importance of knowing your strengths as a founder, and how to hire for your weaknesses.
- The value of communication in a text heavy, digital world.

Dennis Mortensen

Dennis Mortensen is a serial entrepreneur, despite his best efforts to avoid it; seemingly ingrained in his blood, Dennis comes from a lineage of business owners and seeing their painstaking efforts while growing up, originally hoped to avoid that path. However, when his plan to pay off college debt went awry, his instincts lead him on an entrepreneurial course which has been his trajectory since. In those early days, after several successful sales and exits, his strategy was bold: doubling down on his successes with each new endeavor and angel investing the next. Ultimately he hit his first bust, a venture he’s since coined his “very expensive MBA,” which left him with 4 tickets to the caribbean and some soul searching. Over red bulls, a staple of his daily diet, Dennis tells us how he got up after his fall, still unable to shake his entrepreneurial drive, the successes he’s seen since by focusing on a single thru line; focusing heavily on analytics and inching closer to digital intelligence and automation. This is a system he’s closest to today as founder and CEO of x.ai, an artificial intelligence startup committed to solving the problem of calendar management once and for all, or as he puts it, “we schedule meetings.”

What You’ll Learn:

- The pros and cons of building a business exclusively on cash flow.

- Why your product focus should be being world class at one thing, versus half-assed at seven.

- Why all no commercial websites should exist without analytics.

Jackie Cuscuna & Brian Smith

When Brian Smith and Jackie Cuscuna met, they were teachers. However, as time would have it, their relationship and careers have evolved to a place they could’ve never imagined. Over a decade later, as their relationship evolved, a shared dream has come to fruition as the purveyors of some of the country’s most delicious ice cream, Ample Hills Creamery in Brooklyn, New York (and they are not your typical entrepreneurs). Over Dark and Stormies (and delicious Bourbon Street ice cream), they share their true entrepreneur story: what inspired and continues to inspire them as ice creamers, how that path was in jeopardy after only 4 days of business, and how a special relationship with Disney has gotten them beyond the dark side (and continues to help them grow). While the journey has certainly not been an easy one, the result is undoubtedly sweet.

What You’ll Learn:

- How not being prepared for the best case scenario may be a problem.

- Why in entrepreneurship you should dare to be bold and never be afraid to throw a hail Mary pass

- The importance of remembering to keep a balance in work and life – and noting where the two can intersect

Jenny Boylan

Jenny Boylan has spent her life and career in constant transition. She embodies this evolution not only as a personal motivator and measure for progress as a notable member of the transgender community, but professionally, as she encourages others to do the same, regardless of their pursuits. As writer and professor in the English Department at Colby College and now at Barnard College, she has helped budding writers find and refine their voices and love of the craft for over 20 years. As a writer, she’s authored thirteen books and dozens of short stories, more recently shifting from humor to share her personal transition through the likes of her memoir “She’s Not There: A Life in Two Genders” – the first bestselling work by a transgender American. Most recently she has become one of the de facto spokespeople and advocate in the LGBT community and appeared as a consultant and cast member on “I Am Cait” (amongst other efforts). Throughout, she has used her experience to empower others, helping them find their way within an often divided community. Over a selection of ABC Beer Co.’s favorite Belgian-style beers, she explains the obvious and not so obvious challenges she’s encountered: why not all transgender people are not created equally and the value of being honest about yourself in order to connect with others in a meaningful way.

What You’ll Learn:

- Why making people laugh is great, but making people cry is better.

- How division within a minority group can often be as detrimental as those who oppose them.

- The challenges that come with being the “voice of reason” a divided community struggling for recognition.

© 2007 Photos by James Bowdoin.

Stephen Elliot

It has been said that often the truth is stranger than fiction, and no one demonstrates that more than Stephen Elliot, founder of The Rumpus. He has spent his life using writing and filmmaking as an outlet for expression when he often had nothing else. Growing up in group homes for orphaned kids in Chicago, he found himself in precarious situations and circumstances, ultimately at the helm of his own destiny. Over ginger beers provided by Alphabet City Beer Company, he describes exactly what that meant: negotiating his right to attend public school, why majoring in history lead to a tailspin with drug use, how he overcame that to get a Masters from Northwestern, all the while suffering the severe ups and downs that culminated in his life’s work. The results are captured in his novels and films, particularly his memoir, the Adderall Diaries, (and then the film about making the film that James Franco wrote and starred in). Today, as a contributor to Epic, he continues taking on new perspectives to tell stories, immersing himself in situations for months at a time in order to give the behind the scenes take on things like LA’s Silicon Beach, amongst others, as well as his own experience having a “real” job for the first time in his whole life.

What You’ll Learn:

- Why sometimes having no money is better than not having enough money

- What it’s like to go through your career without ever having a “real” job

- What happens when you bring a dominatrix to a film premiere

Michele Serro

Michele Serro’s career has been driven by finding and seizing opportunities as they are presented to her. As a kid, this meant that a natural singing talent turned into a pursuit of an Opera career and training at both Julliard and Indiana University. However, when subjectivity and politics trumped her passion, she shifted her artistic abilities and soft skills to the world of design, where she was able to gain experience in product and innovation at IDEO, amongst other places. It was when she was confronted with the practical and emotional challenges of first time homebuying that entrepreneurship struck and she was inspired to “revolutionize, not disrupt” the real estate world with her company Doorsteps. Over negronis with campari provided by ABC Wine Company, she explains how, while unconventional, the path of her career and consistently being a “beginner” ultimately lead to her success as an entrepreneur, why that success should not only be defined by the acquisition of her company, and the challenges of figuring out what comes next.

What You’ll Learn:

- The value of knowing your strengths as a founder and knowing which part of the process they should impact

- How empathy and prototyping should drive design

- Why founders should “date” ideas before building them

Oz Lubling

Oz Lubling’s lifelong obsession with the internet began at its inception; in a time when there were no rules or standards, he split is passions between graduate school years focused on Computer Science and a love for creating products and pushing the envelop. This carried over to the foundations of his professional career — a developer turned UX professional — when both disciplines were largely undefined and Mountain View was still a rural town in Northern California. Over lychee martinis Oz recalls the course of his 20+ year career alongside the growth of internet; why being employee number one of the now digital agency behemoth Razorfish gave him a front row seat its evolution and how after several years he’s found his way back to making products with its co-founder, Jeff Dachis at One Drop.

What You’ll Learn:

- The importance of context within product.

- How even products which solve problems well can fail.

- Why company culture may still have value in the modern tech world.

Allison Schrager

Allison Schrager doesn’t see obstacles, only opportunities. As a student with no mathematical background she set out and earned a PhD in economics from Columbia University. When her graduate advisor failed her, she changed her trajectory and made a career as a successful pension economist. At the onset of the financial crisis of 2008, she transitioned to journalism. While her accomplishments and accolades across various industries are no short of impressive, most noteworthy about her is that the goals she strives to achieve seem to always sit at the pinnacle of what most would consider an insurmountable uphill battle. Over wine, Allison explains why she thrives in these challenging situations, why her dream jobs exists at the epicenter of finance and creativity, and how her enthusiasm may be her greatest asset.

What You’ll Learn:

- Why obtaining wealth shouldn’t be a goal for retirement.

- How enthusiasm can bring opportunity, but doesn’t replace hard work.

- Why validation can be a motivator if you keep it in check.

Wesley Verhoeve

Wesley Verhoeve has made a career of helping others tell their story: from his time in the music industry, to partnering with startups, and most notably as a photographer, he finds the gifts that each brings to the table and helps to emphasize them. In his latest passion-project-turned-real-project, One of Many, he traveled to underrated art communities across the US to shine a light on them and unite makers in each; connecting them with others like them and giving them a platform to showcase their work. But what about the storyteller’s story? Over rosé provided by Alphabet City Wine Company, we heard from Wesley about how his patchwork background from rural Netherlands to Bloomington, Indiana and ultimately a bicoastal residency makes him uniquely qualified to be the one to unite the many.

What You’ll Learn:

- Why you should follow your passions, even if the path seems unpaved.

- Being successful in tech or art in the US is not confined to New York or San Francisco.

- How being a part of a team can ultimately help you become stronger as an individual.

Andrea Syrtash

One of the ever-growing concerns as the digital world expands is what effect it will have on relationships; from business correspondence to social media to online dating, we’re constantly changing the way we interact with one another. Leading the charge in research and expertise, Andrea Syrtash is constantly monitoring and navigating the myriad perspectives and implications on modern relationships and advising on how to navigate them. A self-described “slasher” and naturally born advisor, her certified expertise spans across multiple forms of media as a coach, author, television personality, and most recently, podcast host. Over Chardonnay provided by ABC Wine Co., Andrea explains that while the problems she aims to solve can be complicated, her goal is quite simple: to contest the poor advice so often given in this space and to help people break free of their preconceived perspectives in order to find what suits them – from lasting companionships to a reason to swipe left.

What You’ll Learn:

- The single thing that both men and women want.

- How perspective becomes reality and how to changing it may be important.

- Not all expertise comes from experience; sometimes the best way to advice comes from learning from others.

John Gardner

If there’s one constant in the startup world it’s that no two companies can follow the same path to reach the same conclusions; LearnVest is no different. Over Ridge Three Valley Zinfandel, CFO and cofounder John Gardner recounts their very comprehensive story. As a hedge founder founder seeking an alternative path, he started the company from the ground up in a partnership between himself and his cousin, Alexa von Tobel. Over time, they grew and evolved that business in both size, offering, and locations, all the while setting and achieving goals only to reset and start the process again. It’s because of this laser sharp process and their keen ability to surround themselves with both subject matter experts as well as be inspired by universally innovative thought leaders which lead to their eventual, successful exit to Northwestern Mutual (and the work doesn’t stop there).

What You’ll Learn:

- The importance of creating the narrative for your product, especially if it doesn’t exist.

- How to approach growth incrementally and the importance of being comfortable with evolving the product versus having it all on day one.

- Why striking a balance in experience with both employees and board members is key.

Liz Wessel

Some people have an entrepreneurial sense ingrained in their very persona, and Liz Wessel is a perfect embodiment of that. In fact, she has been systematically starting and pioneering companies and thought leadership in a real way since her days in college. Since then, after a stint at Google, she’s founded WayUp, a company that is revolutionizing how college students find their first real jobs post-university. Over pickle martinis provided by Alphabet City Wine Company, Liz shared her matter-of-fact way of pursuing the things that are a “Liz Wessel thing(s) to do,” a gift which gives her ability to see opportunity everywhere. It’s this which inspired her unorthodox path to starting WayUp, how she’s learned to run a company in such a short amount of time, and how not she’s not been afraid to put herself out there to anyone and everyone (and how that’s paid off in great and unexpected ways).  

What You’ll Learn:

- The power of cold emailing.

- Why self-awareness and confidence can be the ultimate keys to success.

- How hacking a hackathon can be the solution to finding your perfect co-founder.

Dan Frommer

Dan Frommer, editor-in-chief of ReCode, has made a career at the crossroads of technology and journalism. Growing up as a tech enthusiast-turned-developer, on the surface it would seem surprising that he ended up in journalism. However, over a variety of hard ciders, he explains how this practical knowledge has served him well, both in creating efficiencies in content development, as well as informing the overall structure to be more conducive to his audience. His tenure as the inceptor of what is now Business Insider, as well as his time as technology editor at Quartz are perfect examples of just how that works, using trial and error to arrive at a new take on often archaic practices in the publishing space.

What You’ll Learn:

- The importance of brevity and simplicity in journalism.

- How email is making a comeback and how to use it to your advantage.

- Why sometimes being both a participant in tech and a journalist can be morally tricky, and where to draw the line.

Elizabeth Spiers

When it comes to content and the internet, Elizabeth Spiers is one of the most influential names in the business. Born and raised in rural Alabama, Elizabeth changed the face of writing for the web when she became Founding Editor of Gawker, establishing one of the best-known, snarky voices on the internet; then just a blog that she maintained exclusively for $1200 per month. Since, she’s taken great strides, experiencing roles at the likes of the NY Observer and most recently co-piloting EverUp in collaboration with Flavorpill, all the while maintaining the drive to make as much impact in this ever-changing landscape. Over Muriel Rioja, she shared with us her points of view about morality in journalism and abandoning archaic revenue streams in order to continue to fight the good fight for content on the web.

What You’ll Learn:

- When building something from scratch why short term obstacles should not stand in the way of long term goals.

- Why owning your own failure is the key to avoiding compromise.

- The importance of sticking to your values, even if it’s a riskier path to success.

Albert Wenger

As the startup world continues to expand, with it the myriad opportunities and options for success do as well; and no one process suits everyone. As a partner at preeminent VC firm Union Square Ventures, Albert Wenger navigates that everyday, and as a failed entrepreneur, it’s something he’s experienced even more personally. A self-described technology optimist, takes us through the approach he and his partners take to investing and advising companies, how, as a company, they aim to be effective and not “right,” and why staying focused on a single (evolving) thesis has lead to their success.

What You’ll Learn:

- Why as a founder one of the biggest mistakes you can make is hiring people like you.

- How raising money is like singing in the shower (and why that matters).

- How deferring funds early on is a better path to success.

- What will upstage capital as the new most important commodity in business.

- Why all software can and should be social at its core.

Meghan Graham

As interconnectivity of the world increases, so does the call for authenticity and two-way, flexible, communication. Brands who once dominated the marketing conversations are now struggling to find meaningful ways to engage with their customers, companies large and small who once offered canned benefit packages are struggling to relate to and support their employees. Meghan Graham first became aware of this phenomena in a meta-scenario as she was reporting on the decline of advertising dollars to publishers as a writer for Wired; however, since then the writing on the wall has only become more clear. Seizing the opportunity to modernize the way we engage with people (customers, coworkers, parents, or all three) on a personal level, she founded Brick Wall Media, which is not only guiding brands to be more impactful, but setting the example for companies to do that as well.

What You’ll Learn:

- Why sharing values with your customers and employees is table stakes for remaining relevant.

- How flexible hours may be the solution to long-term satisfaction and productivity. (See her Medium article about it.)

- How larger brands need to evolve their thinking around what it means to connect with their customers through truly useful content.

Tony Hendra

Tony Hendra is, without question, one of comedy’s living legends. Described by the Independent of London as “one of the most brilliant comic talents of the post-war period,” Tony boasts a career including being one of the original editors of the National Lampoon magazine, discovering some of the original members of Saturday Night Live, and as one of the stars of the rockumentary This Is Spinal Tap. Over champagne at this Upper West Side apartment, he discusses how the industry and art has changed over time, particularly as it’s adapted for new media, how he’s adapted to that with his podcast the Final Edition Radio Hour, and his stance that no two vessels deliver the punch line the same.

What You’ll Learn:

- Why you shouldn’t chase trends and why media matters.

- The parallels of satirists and monks.

- How brands can rise & fall depending on vision and leadership.

Check out some of Tony’s latest work as founder of the Latest Edition Radio Hour: https://soundcloud.com/thefinaledition

Rachel Sklar

One of the paramount needs of an industry so dependent on innovation as tech is the ability to understand varied perspectives and experiences; and yet still, the issue of diversity, specifically gender representation, is longstanding. It’s an issue that, over the course of her career, Rachel Sklar has not been able to ignore. Starting off as a lawyer in New York City, it became clear to her that she was perhaps an outsider in the boys club. However, it was when she transitioned to a stint in the early days at the Huffington Post, fighting tooth and nail to create opportunities for herself and ultimately getting access and insight into other industries, that the “where are the women?” drumbeat was evident in every single one. Over Cole del sole prosecco provided by Alphabet City Wine Company, she talks about her outspoken nature on the issue of gender politics and her efforts in advancing the conversation through founding both The List and Change the Ratio.

What You’ll Learn:

- The parallels of founding a startup and early parenthood.

- How being hungry and creating opportunities is still the norm for women in modern industries.

- How tech is no longer an industry on its own, but rather, sits at the center of the venn diagram that is business.

- Why it’s important to say you’re an expert and mean it.

Avi Flombaum

With exponential growth in innovation and tech, the world around it has shifted, leaving opportunity for new jobs and new fields that never existed before; it’s a sector that was created by a generation of makers who saw the early days of the internet not for what they were, but what they could be. Avi Flombaum is one such maker. As a kid growing up in the early nineties in New York City, Avi was introduced to the internet by way of occupying his time in a computer lab while his mother tutored and it was then a passion was forged; A passion that would sustain him down a path of self-taught development skills, foregoing a formal college degree, but opening the door to a successful career in tech, and ultimately founding the Flatiron School. His vision is clear: to shepherd students like him, with a passion for technology and a desire to help shape its future, to have access to a curriculum that he could only dream to have as an adolescent and to give them the chance to change their lives.

What You’ll Learn:

- How vocational schools can get you to your desired goal, but is not a shortcut.

- The importance of a well-rounded educational experience.

- How growing up in tech has changed in two decades and the opportunities created from it.

Jessica Beck

By her resume alone, it’s no surprise that Jessica Beck is a successful startup founder: from her roots at Harvard Business School and experience at McKinsey, she has been brought up with a sustainable business acumen. However, as she describes over a bevvy of micro IPAs, this sort of formal training can only take you so far. There was a lot she had to learn on the job  when creating her product, Alfred, which bridges the service industry with the on-demand expectation of users by providing the everyday person with a personal assistant, or “Alfred,” to help with their intimate daily tasks (think: errands, shopping, laundry) … without them ever actually meeting.

What You’ll Learn:

- As a founder, knowing when you should ask for help (in both funding and roles)

- The benefit of knowing how to do every job in your company

- How a lightweight, non-digital version of your product is the best proof of concept

Justin McLeod

Online dating is a crowded space and becoming increasingly so across platforms. Seemingly a new phenomenon over the past few years, this extreme growth could be attributed to a time in 2011 when, within two weeks of each other, Tinder and Hinge launched and changed the game as we knew it. Hinge’s founder, Justin McLeod, had been working on the app for two years, pushing off a start date at McKinsey until he finally decided to make the app his full-time job. Over grapefruit La Croix, Justin discusses the evolution of the online dating space and how to differentiate in such a saturated industry.

What You’ll Learn:

- The data showing difference in gender behaviors on dating apps and the impact on the products

- Where and when the content of a dating profile matters

- How to approach launching a product that requires people to be on it for true success

- Defining success from a business perspective and the surprising front runners in the industry

Hilary Mason

One of the most important and valuable commodities in the digital world is data. However, accessing and harnessing this powerful resource can be intimidating; that’s where Hilary Mason and her team at Fast Forward Labs step in with their goal to demystify these complexities and instill confidence in their clients. As a computer scientist, Hilary has spent her career fascinated how by how she can use her programming skills, deductive reasoning, and strategic thinking to help create new, useful, and often necessary digital products. Over crisp apple cider, she discusses her experience as the chief scientist at Bit.ly and how that lead to her deciding to create her own thing.

What You’ll Learn:

- The tenets of what makes a great computer scientist

- How computer science (and it’s subset data science) is completely accessible

- Why data can hold the secrets to everything you need to know about your product or audience

Nick Chirls

The world of venture capital in New York City tech has changed significantly in the past decade with access to investment for early stage companies becoming more and more challenging. Enter Notation Capital and it’s co-founder, Nick Chirls, who believe that there’s a gap for seed stage investments that he and his team intend to fill. And Nick knows the NY Tech scene. Over beers provided by Alphabet City Beer Company, he walked through his disgust with the traditional finance world and why he left it to explore the startup world, ultimately landing as a the head of investments at Betaworks.

What You’ll Learn:

- How investors choose their first investments

- The importance of sticking to your thesis as a VC

- How the evolution of older, larger funds has hurt early stage tech companies

- The challenges of being in an equal partnership

Alanna Gregory

As we’ve learned, there is no clear path to successful entrepreneurship and Alanna Gregory’s story is a shining example of that. With an engineering background and beginnings in the world of finance, she was unexpectedly struck with inspiration. Now, as the co-founder of Vive, an on-demand blowout scheduling app for women in metropolitan areas, she’s had to continue to make a lot of risky decisions in order to grow and pivot her business. Over pinot noir, generously provided by Alphabet City Wine Company, she talks to us about the importance of assessing the data at every turn, but that ultimately your passion for your company is paramount to your success.

What you’ll learn:

- Sometimes data doesn’t tell the whole story

- How pivoting in life and in your company can be a saving grace

- Why the motivation of founding a company should be more than big business

- Why it’s important to put something out there, even if it’s not 100%

Chris Messina

Chris Messina is the Developer Experience Lead at Uber, a role he attributes to a life “peppered with serendipity.” A native New Englander, he’s also lived a life that truly embodies the spirit of the internet – a place where everyone has an equal voice, where democracy enables true societal progress. At least in theory. Over Failla Pinot Noir, Chris discusses his high school days in New Hampshire, battling his school to ensure the Gay-Straight Alliance had a place on its website (a battle which almost cost him his diploma), helping develop web standards with the launch of Mozilla, using pioneering social media tactics to launch BarCamp, and how no matter what he does, it’s about continuing in a career he 100% believes in.

What you’ll learn:

- The challenges of web design in the early days of the Internet

- The story behind the invention of the hashtag (#)

- How web standards have remarkably improved the state of product creation

- How his event, BarCamp, helped launch Techcrunch, Pandora, and Flickr

Alexandra Cavoulacos

There comes a time when a person struggles with the “What If” moment in their life and/or career. For Alexandra Cavoulacos, that fork in the road came when she had to decide between continuing down the stable and successful partner track as a consultant at McKinsey or to throw caution to the wind and create her own company, The Muse, a startup she co-founded with Kathryn Minshew. Over glasses of Alsatian white wine, generously provided by Alphabet City Wine Company (abcwinecompany.com), she discusses how she and Kathryn had been burned creating a startup once before and why, since choosing the startup route, she hasn’t looked back.

What you’ll learn:

- The myths and benefits of going through an accelerator program, and why the prestige should not negate the hard work it takes.

- How the stresses of a startup evolve and change as you achieve success.

- Why it’s important for founders to put themselves outside of their comfort zone; “just fucking launch.”

- Gender biases and how to navigate them in raising venture.

Jay Parkinson

The medical industry, while growing and innovating all the time, appears to be stuck in the past; often leaving patients needing something more user friendly. Jay Parkinson, MD, is trying to rethink that world, leveraging the benefits of technology and the emotionality of humanity. He founded Sherpaa in 2012 in order to make health, medicine, and insurance more accessible to everyone. And he’s just the guy to do it; while he’s a pediatrician by training, he has a clear aptitude for systems thinking (a quality which is actually antithetical to the competitive spirit encouraged in med school).

Over Bulleitt Bourbon, provided by Alphabet City Wine Company, we discussed how he’s a taken a problem solving approach and an always-ask-why mentality since med school, and how it’s lead him to focus on creating patient-centered practices and products utilizing technology to actually help people with ease.

What you’ll learn:

- The parallels between digital product creation and innovation in the medical industry.

- The importance of always remembering to ask “why?”

- Why sometimes the best thing to do is the simplest.

- How medicine is too often overly tied to tradition.

- What having a cofounder and having a spouse have in common.

Keeping Up with the Cultural Zeitgeist: The Pop Culture Round-up

Keeping Up with the Cultural Zeitgeist: The Pop Culture Round-up

The world of tech and media is a constantly evolving one. Everyone’s darling one minute can quickly disappear, become a spoof of itself or just become a digital pariah. Creating these trends and even keeping up with them can be a job in itself. The episodes below outline some of our most powerful pop culture conversations of 2015.

 

Gavin Purcell, producer of The Tonight Show with Jimmy Fallon, helps birth some of the funniest and most viral videos on the internet.

What we drank: Greenhook Gin & soda with lime

 

Fred Graver has written for some of the most successful TV comedies of all time (Cheers, In Living Color, Late Night with David Letterman) & created VH1’s Best Week Ever. Now he brings his unique perspective to Twitter as Head of TV.

What we drank: 40’s of Diet Coke

 

Mark Graham‘s job, as Editor-in-Chief of Decider.com, is to have his ear to the ground on all things pop culture. Mark also introduced Dan to his drink kryptonite.

What we drank: Bud Lite Staw-Ber-Ritas

 

Lauren Leto is the inventor of the massively successful Texts from Last Night, which propelled her into unexpected and unwanted internet fame.

What we drank: Ridge Geyserville Zinfandel

Starting Your Own Thing: The Entrepreneur’s Guide

Starting Your Own Thing: The Entrepreneur’s Guide

In 2015, we had the opportunity to hear all sides of the challenges that come with creating your own company. From fundraising, the equity, to ramping up to, sometimes, failing and picking yourself back up again, these stories inspired, educated and helped give a well-rounded look at the truth around what it means to be an entrepreneur.

 

Matt Lieber talks about being the co-founder of Gimlet Media and accidental entrepreneur.

What we drank: Mezcal

 

Ellie Wheeler, partner at Greycroft, her thoughts from a venture capital standpoint are valuable for any founder.

What we drank: Mary Edwards Pinot Noir

 

Kevin Kearney tells the origin story of Hard Candy Shell and what drives passion around creating great products is one of the more emotional episodes of Story in a Bottle.

What we drank: High West Double Rye

 

Christina Wallace‘s experience founding and ultimately leaving her startup, Quincy, is one any aspiring entrepreneur should hear.

What we drank: Whiskey Gingers

Lindsey Green

Lindsey Green has a life checklist and she’s quickly making her way through it. Currently, as the VP of Corporate Communications at Bustle, she is embracing being a millennial – a point of personal pride – as she helps manage the most successful site for other women like her (and, at the time of recording, the 32nd most popular site on the Internet). But in true Millennial fashion, her checklist is varied, as her career experience includes stints in fashion, food, and, of course, permeating passion for tech. As she says, “I don’t want to be less connected, I want to be more connected. I want more Internet.” Over Cupcake Prosecco in wine glass (her signature), Lindsey shares her obsessive relationship with gymnastics, why New York was always the dream, and how she’s working to combat that “there’s a great misconception of [her] generation as a whole,” especially when it comes to ego vs. empathy.

What you’ll learn:
- Why the Millennial generation is truly unique (which makes them a challenge to market to)

- The importance of always staying true to yourself

- How carrying gum can lead to a huge career shift

- That it’s possible to do more than one or two or three things at once and be successful

- No one needs to have just one dream

Matt Lieber

While he’s probably best known from Gimlet Media‘s StartUp podcast, Matt Lieber’s relationship with the audio world harkens back to his undergraduate days, where he ran the radio station at his alma mater, Bowdoin College. As a teenager and into his early career, Matt knew that he wanted radio content to be a major part of his life, but what that actually meant wasn’t apparent. Over glasses of Mezcal, Matt talks about his experience walking away from radio and the subsequent winding path that took him through MTV, Nepal, MIT, and consulting before boomeranging back to the world of audio content at Gimlet; where he and Alex Blumberg are creating an empire out of quality content one episode at a time.

Tequila provided by Alphabet City Wine Co.

Things you’ll learn:

- Why entrepreneurs say, but rarely feel they are actually “crushing it.”

- Public radio is one of the most challenging professions

- In the world of Business Consultancy, it’s possible that everyone’s a novice

- Sometimes the best way to find yourself is in the everyday things you do

- What happens when your startup explodes publically overnight

Brooke Moreland

As a second-time founder, Brooke Moreland has been through it all. She’s watched her former company, Fashism, skyrocket to the front page of the fashion section of the New York Times, receive endorsement and investment from celebrity investors like Ashton Kutcher, only to face the harsh reality of shutting down her dream. In her new startup, Jewelbots, she’s applying all the knowledge she learned from her last experience and creating brand new technology geared at helping girls learn how to code in a fun and relevant way. Over Bulleit Bourbon, generously provided by Alphabet City Wine Co., we discussed how Jewelbots came to be and why being banned from schools is the bar she’s set for success.

Things you’ll learn:

- How to launch a successful kickstarter campaign (or read about it here)

- What you should know you don’t know as a first-time founder

- The challenges of designing digital product for young kids

- The differences between raising venture as a first- vs. second-time founder

- How and when to hire internally versus outside agencies

- How to make the, often heartbreaking, decision to shut it all down

Mike Rothman

“There are no shortcuts to enlightenment.” That quote by Mike Rothman sums up his approach to the impressive career and life that he has lead thus far. In this episode, Mike, the co-founder of Fatherly, a new parenting product  that takes a unique approach to content and commerce, talks about the entrepreneurial spirit drives him. 

Episode highlights include:

- The story behind the origins of Thrillist.

- Why email is “the cockroach of the internet” and why it’s currently one of the most important communication tools for brands.

- How a cross-country bike ride for charity can (or cannot) change your life.

- What you can learn from being Conan O’Brien’s writing intern.

- Why his biggest lesson learned to date is: “Focus, focus, focus. Especially early on… as great as you are, you can only do one thing well at a time.

Over Blanton’s Bourbon was provided by Alphabet City Wine Company.

 

Maya Baratz

Maya Baratz spent her childhood filling up dozens of notebooks passionately writing. At the time, she had no idea that what seemed to be a necessary reality for her own personal psyche could translate into a career. Her love of content, however, could only be equaled with her obsession with technology.

Over prosecco generously provided by Alphabet City Wine Company, Maya discusses the challenges of immigrating to the United States from Israel as a pre-teen – with very little grasp of the English language – through her early years discovering that her love of both content and tech could translate into a real career. Her unique experiences working as a speechwriter for former senator John Kerry and innovating how Monster.com shaped it’s early community have helped lead her to the role of  Head of New Products at ABC News, where she’s doing her most innovative work yet.

Erick Schonfeld

Over the past twenty years, journalism as an industry has evolved significantly. Erick Schonfeld has not only reported on tech throughout that process, but he’s been a major catalyst for innovation within the field as well. His experience follows the shift from print to digital as a priority at Fortune, to the professionalization of blogs at TechCrunch, up until now, as he is championing new technologies to enhance digital storytelling as the co-founder of Touchcast.

Over a few glasses of Grgch Hills Estate Cabernet Sauvignon, Erick discussed the challenges he’s faced at the forefront of journalism; how, over time, the lines blurred between being a “content creator” to the creating of the product itself. Those key learnings have been instrumental for Touchcast, and explain why it’s been embraced by companies like The Wall Street Journal, the BBC, and Style.com, as well as its popularity in the world of education. 

Mari Sheibley

It’s no secret that most successful products are born out of collaboration. Mari Sheibly has made a career of proving that time and time again as a designer for some of the internet’s best, including Foursquare, Rent the Runway, and now at budding Walker & Co.

Early on Mari was dissuaded from the dream of being a professional artist while attending art school which lead to her focusing her sights on the world of product design. In the years since, she’s surrounded herself with teams that challenge her and that she challenges back, building and rebuilding digital products until she knows, almost instinctively, it’s time for her to move on to the next. Over dirty vodka martinis, Mari shared her thoughts around being on both sides of process (client and agency), her lessons from helping a young startup like Foursquare evolve and find itself, and how Walker & Co. is ensuring it does not find itself caught in the stereotypical web of homogeneity.

Michael Pryor

When creating a product, often times the best approach is to start small with core group of users and use cases and grow. Michael Pryor successfully bucked that trend when he co-founded Trello, basing his company on the idea of “bringing structure to any process,” regardless of the aim of the project or industry using it.  Since its launch at TechCrunch Disrupt 4 years ago, it has gained 10+ million registered users who are utilizing it for projects that span from wedding planning, to HR onboarding for small companies, to Sales CRM and beyond. Their reach is only growing thanks to the evangelization of the product by many core users.

Trello wasn’t Michael’s first attempt at digital products. Growing up in Lancaster, PA, he had early interest in computer science. Over a few cans of Mama’s Little Yella Pils (generously provided by Alphabet City Beer Co.), he remembered his ‘tech’ origins (which involved meticulously inputting Basic code from coding magazines, into his Texas Instruments computer), his time at Dartmouth building websites for professors, and his subsequent years working for Juno and a development consultancy that weathered the pop of tech bubble by creating their own products (most notably Stack Overflow).

Several decades, products, and teams later, he’s continuing to get to the root of user obstacles, creating the best tools to solve them. Needless to say, he’s on to something good.

Kellee Khalil

Kellee Khalil grew up surrounded by entrepreneurs. Her father moved to America with a one-way ticket and an eye on the American dream. His business-minded attitude, paired with the creative influence of her florist mother, set a lifelong example of finding an opportunity and making it work. As a true California girl, she attended USC where her major was entrepreneurial studies. This gave her not only the foundation to become an eventual business owner, but helped solidify the business acumen she had grown up with: “identifying problems and building solutions around it.”

As the Maid of Honor for her sister’s wedding, she found such a problem to solve as she was constantly turning to Google for answers to everyday, commonplace, wedding planning needs. The outdated and unhelpful businesses that comprised the $99 billion dollar wedding industry needed innovation and that’s just what she was going to bring to the table with her company, Loverly.

Over Tito’s vodka sodas, provided by Alphabet City Wine Co., we discussed her take on outside capital (“Sometimes it’s better to sell the dream and get as much money as you can, then you have enough time how to figure out how to execute.”) and how ripe the wedding industry is for an innovative overhaul.

Inder Singh

Growing up, every kid wants to be an astronaut. For Inder Singh it wasn’t just a dream: he “did everything in [his] power to get there.” He threw himself into the field starting with attending Space Academy as a kid, learning to fly a plane at 16, and finally working at major rocket labs while studying engineering at the University of Michigan (which he was compelled to attend because their symbol flies on the moon). This full-speed ambition, along with a drive to constantly be learning from the best and the brightest is a theme throughout Inder’s life and has produced a dizzying number of accolades: the founding of a successful nonprofit, 3 master’s degrees between MIT and Harvard, and public praise from Bill Clinton for his work in bringing more affordable malaria treatments to the third world, just to name a few (though his mom still wanted him to follow in his family’s footsteps and become a doctor).

His latest venture, Kinsa, looks to combine his extensive background to revolutionize how the spread of infectious diseases are tracked, starting with a simple device that every household has: a thermometer. In this episode, we sat with Inder to walk through his story and what he sees next on the global health tech horizon. While he may not be an astronaut or doctor, we think his mom is still pretty proud.

This episode’s Wodka tonics were provided by our friends at Alphabet City Wine Company.

Carolyn Lanzetta

As a day trader at JP Morgan your life often resembles that of a startup founder: too much to do, constant pressure, and around the clock hours. What you may not see is a key difference in a lack of flexibility. Carolyn Lanzetta entered the finance world after graduating from Dartmouth. She was drawn to the banking field by the clearly defined roles and expectations. After the birth of her first child, though, she knew something, mainly her profession, had to change. Parents, especially mothers, were not abundant on the trading floor and the rigidity of the job allowed for zero flexibility. In the cut-throat world of big finance “you barely grab lunch from the delivery guy who brings it to the lobby, let alone an appointment at your kid’s school.” So she quit and left a world of clear cut rules and entered the completely foreign world of startups.

Plum Print is the brainchild of Carolyn and her cousin. Together, they pooled their knowledge and sought to address a need of many parents: preserving their child’s artworks and momentos in a meaningful way, while also reducing the clutter. They started small, and as the company grew, so did their web footprint. Over John Daly’s we sat to discuss the parallels between finance and the tech world, how, with zero tech knowledge she has found both her footing and place as a startup founder, and the challenges, mistakes and lessons that she has encountered along the way.

Sam Kassoumeh

Unlike many of our guests, you won’t find Sam Kassoumeh on Twitter. In fact, you won’t find his profile on any social media sites. He removed them all before Snowden’s leaks, based on an inkling.

Growing up in ‘Ford Country’ he was surrounded by friends and family working in the automotive industry. It was assumed he would follow in their footsteps. At 14, he was drawn to a different path as he began ‘white hat’ hacking as he broke screenname rules on AOL 2.0. From these humble beginnings he began his career as a top internet security expert.

After graduating from the University of Michigan and a few corporate jobs that followed, he worked his way up the ranks, eventually helping build a military level security system at Gilt. He realized at this point how much the sphere of the internet needed better security as a whole and launched his company Security Scorecard. Over a bottle of Cotes du Rhone, we discussed his take on internet security and why it’s not that “people should be fearful, but with that being said, people need to be educated.” In the age of celebrity cell phone hacks and Ashley Madison data leaks, it should come as no surprise that 70% of breaches are due to third party intrusion. This statistic becomes more and more relevant as we become increasingly reliant on the cloud.

Our conversation was truly one of the most enlightening that we’ve had to date. With the knowledge that “a basic level breach costs a company $6 million and 2 years of remediation” it’s a conversation that could save companies both large and small.

Christina Lewis Halpern

Much like many who found themselves in tech, Christina Lewis Halpern began her career in journalism. Unlike most though, it’s her first foray into tech from that world that is making the biggest splash.

From covering crime in Stamford, CT to grabbing quotes from Donald Trump on Wall Street, as well as the boom and bust of the real estate industry, she saw the true spectrum of wealth and humanity play out in the daily news. It left her wanting to help inspire change, much like her initial source of inspiration: her father. As the first African American to build a billion dollar company he sought (and succeeded) to bring diversity to some of the business world in the 1980s. It was his path that ultimately helped Christina find her calling with All Star Code.

As she says, “Tech is the engine of job growth and wealth creation… and if we don’t have people from diverse backgrounds in tech we face many problems.” With All Star Code she is helping to bring some much needed diversity to the world of coding. Over Sancerre provided by ABC Wine Company, we sat with her to discuss the evolution of tech and how it not only can, but desperately needs, to be more diverse in order to avoid a new economic crisis.

Dennis Crowley

What if the games you played as a kid shaped your eventual career? Dennis Crowley grew up in a family that made everything into a game with the simple goal of adding an element of fun to everyday life. After graduating from Syracuse University he moved to New York where he nurtured his passion for creating, with stints at early tech companies (Jupiter Research, Vindigo) until the first dot com bubble burst. At that time, when it seemed like the fun was over for many in the industry, he set out to find those still passionate about tech and a bit of direction, leading him to the esteemed ITP program at New York University. It was there that he developed his thesis Dodgeball, which would later be purchased by Google, immediately immersing him in the world of big tech and startups. Whether it was a product that was ahead of its time or just lost in a large company without a clear plan, Dennis eventually saw the writing on the wall and painfully walked away from Dodgeball with Google pulling the plug shortly thereafter. Dennis was still convinced that making the mundane fun could be a reality and the ideas behind his grad school thesis were worth another shot. Foursquare was born.

As Foursquare evolved and the social media scene exploded, Dennis found himself at a crossroads. The original intention for the app was there, but user behavior was shifting and the company had to make major changes. Swarm, their most recent endeavor, is now in its second year. Over Keegan’s Mother’s Milk beer, we discuss the decision to pivot the Foursquare brand, the real reason behind it, and how following the path that’s been your guiding force since childhood can pay off in big ways.

Alexandra Klasinski

Alexandra Klasinski doesn’t play by anybody’s rules. As a Silicon Valley native, she grew up surrounded by technology and thought processes about innovation, but even immersed in the heart of it all, unsurprisingly veered away from the tech path and towards her passions: art, photography and doing the unexpected. From managing a fast food restaurant to working with high profile comedy writers and eventually with musicians (and a stint in a band herself), she’s let all of her experiences stay true to her idea that every job offers the opportunity to do something new.

Over boxed rosé spritzers (which she’s coined “the douchebag”), she explained that as the music and arts spaces have evolved to be more digital centric, she has now found her space in tech. When working with companies like Lomographic Society International and Edelman didn’t prove to suit her personal growth (the primary focus of all her pursuits) she didn’t let her deter her. Today, she sits very happily at the intersection of art and tech at 20×200 as the Director of Partnerships & Programming where she is able to bring art to the masses in a way that is both special and unique to the artists, especially herself.

To see her (and other great artists’) work in action, check out 20×200. And adventures @alexandrak.

Mark Mangan

Mark Mangan is the cofounder of Flavorpill Media, a company he started 15 years ago as a last ditch attempt to save a failing startup. He took one element of the existing business: an added value email newsletter, which, at the time (and even now) seemed like an impractical way to sustain a business. But, from this (at the time) unique offering of a list curated local, cultural events (with a harsh editorial guideline to maintain authenticity) the company grew to become a leading culture and lifestyle brand. And with every success, they expanded, eventually creating large custom events of their own such as the renowned First Fridays at Guggenheim, as well as expanding to many markets & content types, including noteworthy blog, Flavorwire. As the head of  their innovation lab, Mark won’t let the company rest on its laurels, as he continues to push the envelop to new platforms as media consumption evolves.

This position has not been without its challenges. Over 2 bottles of lambrusco, Mark shared his beginnings — which actually start with him searching for the net (that’s right, it took a couple months for him to actually find it). Once he did he was scrappy in his approach, building websites which turned to companies, seeing the many successes and failures that can only be seen by someone who was pioneering virtually unchartered territory. The result was a personal realization: that as a founder, often times losing part of your team is more difficult than folding a company. The early insights also inspired his professional approach to begin early dialogue about freedom of speech on the web in a book he coauthored, which was noted by the New York Times as “required reading for anyone interested in free speech in modern society.”

For more from him, don’t go to Twitter (because he doesn’t tweet), but keep an eye on the upcoming innovations from Flavorpill.  

Timoni West

As a digital designer, Timoni West’s portfolio started much like many others in the late 1990s: on Geocities. During those early days, when formal design education opportunities and mentorship eluded her, she applied self-motivation and a fearless approach to obstacles which ultimately allowed her to succeed beyond her imagination. With a career that boasts the likes of companies like Flickr and Foursquare, as well as navigating the sometimes frustrating world of freelance, her often unconventional methods have resulted in a career that is as strategic as it is creative.

Over a bottle of Kim Crawford Sauvignon Blanc, we discussed her upcoming endeavor as the Principal Designer of Unity Labs. There, she will be pushing her collective experience in a new direction into the realms of virtual reality. We look forward to raising our glasses to what comes next!

For more from her, follow @timoni.

 

Fred Graver

It takes great skill to to be able to write consistently funny jokes on a day-to-day basis. To be able to do that across mediums as audiences adapt and technology evolves is a skill that surpasses the word ‘advanced.’ Over the past 30 years, Fred Graver has leant his talents to a staggering list of extremely popular comedic experiences with diverse voices and few commonalities (apart from their successes). He helped reinvent the format of the talk show with Late Night with David Letterman in the 1980s, the limits of sketch comedy with In Living Color in the 1990s, and how we talk about pop culture in with VH1’s Best Week Ever in the 2000s.

Over magnum sized Diet Cokes, he told us how as the creative lead of TV at Twitter he is able to continue leveraging his skills at adapting the art of storytelling in the TV world and bring it to the masses in an even more meaningful way. However, the stakes now aren’t just ratings: he’s pushing the networks to compete in a real-time global conversation that extends beyond their traditional broadcast comfort zones. All the while, keeping his eye on whatever may be the next big movement in storytelling. Cheers!

Stacey Mulcahy

Stacey Mulcahy is a technologist of the masses who has built her career on “just figuring it out.” As a social worker in Ontario, Canada, her career originated both geographically and professionally far from where she is today. She was drawn to the field, inspired by the teachers in her family who preceded her. While this path was ultimately not for her, she left with the motivation to better the status quo of the people she worked with. She has taken this same altruistic approach to the tech and corporate world where she was met with an entirely different set of challenges.

Over Moscow Mules, she recounts her upbringing in the digital space: becoming a developer by accidental necessity in order to pick up the slack of her team, transitioning from small to large agencies, and learning at each turn that we’re all better at what we do when we can learn from each other. Now, in her current role as Senior Technical Evangelist for Microsoft (a developer who talks to developers), she is finding the balance of being in a traditionally corporate environment and remaining true to herself as @BitchWhoCodes. However, we learned that it is because of her unconventional, ‘no shits given’ approach to an often disheartening, patriarchal field that makes her one of the right people to further the future of the industry and lead the next generation of tech.

For more, check out @bitchwhocodes and https://tmedium.com/@bitchwhocodes.

Buzz Andersen

Buzz Andersen has a resume which reads like the starting lineup of a tech all-star team, boasting the likes of Apple, Tumblr, and Square. More impressively, however, is his learn-on-the-go attitude which got him in the door of each, starting with his dissatisfaction with the basic computer courses offered in his Colorado high school and the curriculum which was written for him because of it. And as an engineer, he has continued to push the envelop, has honing his skills around iOS development, starting with his iPod transfer app, PodWorks (which started as a means to introduction to Apple), and early Twitter client Birdfeed, all the while enjoying the merits of each.

Over freshly made margaritas with Tres Generaciones tequila, we got a peek behind the curtain of these tech behemoths, who surprisingly share many of the same challenges startups face everyday. It’s because of his experience and consistent chutzpah that lead Buzz on his latest endeavor, now on the agency side, as co-founder of 3 year old Brooklyn Computer Club, a development consultancy agency; appreciating and overcoming the challenges that this new role brings.

To keep up, follow @buzz and check out Brooklyn Computer Club.

Kelly Goldston

Kelly Goldston is a marketer after our own hearts: data-driven to the core, she’s changing the norms in the “fast fashion” space as VP of Marketing at ELOQUII.COM, her dream job. In her arsenal, the power afforded her as a digital retailer partnered with a fan army who, when faced with the potential of ELOQUII closure, petitioned for and ultimately inspired it’s spin off from the Limited brand. The best part? She was one of those fans.

However, as we learned over Roederer Estate Brut, the perfect pairing to her bubbly personality, this happenstance would not have been possible without the career path which precedes it. From a controversial period in sales at early Groupon and ultimately data analysis, she was compelled to further her trajectory to better serve the customers she advocated for. So, with a stint at Amazon’s Quidsi brands, Diapers.com and Casa.com, to be exact, and an NYU Stern MBA specializing in marketing and business analytics it only seemed natural that she’d end up where she is. All it took was that one customer service call…

For more from Kelly, please see @MsKellyGoldston.

Mark Graham

Many of our guests can trace their internet beginnings to one pivotal moment which changed their entire trajectory. For Decider.com’s Editor in Chief Mark Graham, it was his first search query on Netscape Navigator in 1994: “Björk.” From those humble beginnings and his unparalleled affinity for brands and advertising, he has enjoyed an interesting and varied career riddled with the adventures that growing up in the early dot com era affords. However, in a time when people were trying to figure things out online, he had the added pressure of making that happen from his hometown of Detroit within behemoth companies like Borders and OnStar; this, made all the more complicated while maintaining a secret persona online Uncle Grambo, with his pop culture blog-before-blogs Whatevs.org.

Suffice to say, when the time came, Mark took a leap and ended up amongst his internet brethren in New York City after a failed attempt to join Best Week Ever ultimately paid off. It was this which lead to leadership positions at VH1, Gawker, and now heralding at Decider.com. It’s been quite the journey, for sure, made all the more entertaining while being shared over Bud Lite Strawberitas. (And also our worst hangover to-date!)

Cheers!

For more from Mark, check out the latest at his (legitimized) whatevs.tumblr.com and his musings at @unclegrambo.

Ashley Granata

Ashley Granata has spent her career bringing her passion for fashion to the forefront of the tech world. As an FIT grad, she lept right in as a buyer for Bloomingdale’s (on the seemingly lowest rung of the web store) and has never looked back. However, it’s because of her keen sense of the industry and drive to innovate that she is now working on her second startup in the fashion and retail tech scene.

Over Fernet Branca, she recounts how the impetus for her first co-founded company, Fashism, began with the idea of by encouraging people to feel comfortable in their own skin and find their unique style while stepping out of their comfort zone by connecting them with others. And ultimately that product also encouraged her to do the same, forcing her to step out of her own when finally making the difficult decision to close shop. However, never discouraged, we got a sneak behind the virtual curtain into her latest endeavor as Entrepreneur in Residence at Rothenberg Ventures where she is further bridging the fashion space into cutting edge VR technology. She continues to  believe that when “you know you that you look good, you feel really good and you can be at your best” and, what can we say? We’re feeling pretty good about how the future of tech is looking.

For more from her follow @ashley_jeanne.

Seth Porges

Seth Porges is a jack of all trades; a journalist, tech entrepreneur, TV personality, and semi-professional karaoke enthusiast, who is constantly jumping between media in pursuit of his interests. As a young man he became interested in pursuing a career in journalism with the allure of the perks associated (free movie tickets, anyone?). However, it was after his time at Northwestern when he saw how that field actually does pay off. Upon graduation, he fully entrenched himself into reporting in the budding New York tech scene, which opened the many of the doors he’s entered today.

Now, with a strong writing career behind him, he is able to attribute this immersion to other aspects of his life, particularly his co-founded passion-project-turned-successful-startup Cloth App and added a foray into the TV world. Over Lagavulin scotch, he explained to us that, in his career, it’s all come down to seizing the right moments and timing, and having a signature karaoke move.

Oh, and did we mention he also did this Action Park documentary?!

For more from him, check out @sethporges and download Cloth App.

Alex Tryon

When Alex Tryon finally got her first bonus at American Express, all she wanted to was buy a piece of art by Jock Sturges, her favorite artist. But the gallery world road blocked her and painted her into a virtual corner; thus, the idea for her startup, Artsicle, was born.

However, Alex’s love of art didn’t start at Amex, but rather was inspired while traveling in Europe as a kid. A native Texan, she loved discovering the world that art overseas opened up for her. She then pursued that knowledge, along with the practical study of business communications, at U Penn. Her journey from startup idea to formidable business isn’t what you may expect, but it’s a unique tale that truly embraces love, risk and, ultimately, the culmination of her dream.

To keep up with her, check out @alexistryon.

 

Ulrik Hogrebe

As Creative Director of one of the world’s most well-known and respected news organizations, BBC News, Ulrik Hogrebe definitely has his tasks set out for him. This is true especially when you consider the ever evolving landscape of how news is created, disseminated, and consumed on a daily basis. It’s a position which he found seemingly naturally, by way of many years of education and experience: from brand strategy at E-Types and post-graduate studies at both the Copenhagen Business School and Copenhagen Institute of Interaction Design, he is compelled by a desire to be a part of the “making of things.”

Luckily for us, his background also includes a stint as a bartender; so, over hand-crafted old fashioneds, he filled us in on how his experience has been about raising the bar from a culture of “good enough” to meaningful interactions, knowing when to push pride aside and ask for help, and that the best way to get into something is to just get your hands dirty. His story is a reminder to us that the best way to learn and grow, both for a product and as a person, is by not getting bogged down by formality and tools and to continue to experiment and take risks.

For more from him, see: @ulle69.

Lauren Leto

When Lauren Leto, at age 22, started a blog listing random text messages from her boyfriend and friends, she had no dream or idea that it would immediately turn into the massive success that Texts From Last Night became, and cast a spotlight on her that she never expected or wanted. As a law student at Wayne State with a passion for writing (and actual dreams of becoming the next John Grisham) she didn’t even have ambitions for tech.

However, over glasses of Ridge Geyserville, we learn how this unexpected twist allowed her to rise to the occasion and inspired the next steps of her journey in New York City. Once there, she saw the rise and fall of a company, Bnter, took a short stop as a Hacker-in-Residence at Betaworks, and set the foundations for her forthcoming new endeavor, Listen, all while maintaining a healthy distance from being the “Texts From Last Night girl.” Lauren’s path is filled with a lot of hats, some accidental successes, and some hard learned lessons (oh, and a podcast of her own) – a true founder’s story.

For more from her, check out @laurenleto and Judging a Book By it’s Lover.

Neil Capel

As the founder and CEO-turned-Chairman of Sailthru, Neil Capel has spent many of his days helping brands personalize every interaction they have with consumers. In fact, thinking about these meaningful interactions is something he and his family have been doing in real life for generations as greengrocers in England. Sailthru, however, was his way of offering them at exponential scale while solving the growing complications brands faced as digital evolution was distancing them from their customers.

Ironically, by starting a company to help solve these problems for others, he was presented with a new set of worries: learning the ins, outs and pure mistakes of raising money, the art of using improv in sales meetings, the importance of work-life integration, and ultimately how to truly evolve a company from startup to a fully-functioning corporation.

AND, just before this episode was set to launch, we learned that Neil was experiencing a new set of obstacles; as a follow up discussion, he shared with us his most recent undertaking in replacing himself within the company as he transitioned from CEO to Chairman, making his life all the better.

For more from him, check out @neiljcapel and Sailthru.

Aubrey Sabala

Aubrey Sabala is a leading marketer in tech, with many major brands who credit part of their success to her time there: Facebook, AOL, Digg, and currently, Google, to name a few. In fact, @Aubs, as she’s known to her over 28 thousand Twitter followers, has followed a path over the past 15 years that traces the journey of the internet itself.

But in our conversation over Heitz Cellars cabernet sauvignon, we learn that that’s just scratching the surface. In fact, she cites her love of spreadsheets and the parallels she draws to scientific processes she learned while majoring in Biology and Genetics that have lead her to become the success she is today. And it’s her desire to continue to find unique opportunities for brands to provide exclusive access to the masses which will further her successes in the future.

For more from her, see aubreysabala.com.

Kevin Kearney

Kevin Kearney is one of the foremost thought leaders of user experience in the industry. He studied literature and philosophy, but transitioned to a career in UX largely before the discipline existed. Websites were haphazardly assembled with few goals and considerations for the end user. Kevin knew there had to be a better way.  It was after many years of working for big agencies (such as razorfish) and big media companies (such as Hulu) that he became frustrated with the soulless processes and smoke in mirrors of advertising. Together with our host, Dan Maccarone, he was  inspired to try to make it better on his own by founding the agency Hard Candy Shell. In his own words he knows he’s “not curing cancer, just trying to make the world suck less”. 

Over a bottle of High West Double Rye, we began one of our most personal stories to date. Kevin shared the fundamental pieces important to user experience: caring about people and checking one’s ego at the door; a compassion that will continue to better the internet as we know it. 

Alli Mooney

In the digital universe, Allison Mooney plays a role which is rare and invaluable in what makes and breaks a product’s success; in identifying trends, she has her finger on the pulse of how people are engaging, which is often an undervalued piece of the industry. But this isn’t new territory for her.

In fact, it was early in her career at Details magazine where she began to see the writing on the wall: recognizing how important the Web would be for content and finding early insights in the significance of mobile. It was that keen awareness which lead her to become the Head of Trends for Google and editor-in-chief of Think with Google, where she currently preaches what she practices: letting digital and data be the heart and start of what comes next for products and brands alike (versus being the last minute add on or falling by the wayside entirely).

As such, and as the co-host of the BCC party, one of NYC Tech’s most attended monthly gatherings, Alli has established herself as a consistently important and friendly voice in the industry. Cheers to that!

Check out @allimooney for more on what she’s up to.

Jonathan Basker

Jonathan Basker has spent his career becoming an expert in people. As a self-described “dork” in his early years growing up in sleepy Issaquah, WA (fun fact: where Harry and the Hendersons was filmed) and majoring in poetry in University of Washington, it is certainly an unexpected career trajectory. However, with a life that has been split between traveling the world and helping growing companies like Betaworks, Etsy, and BarkBox find the right teams, he’s studied humans in myriad cultures; learning lessons along the way which are  applicable to startups and individuals alike.

In this episode we hear how all of this knowledge lead him to eventually found a company of his own, his newest venture, Basker & Co, as well as the critical lessons he has learned along the way in company culture, leadership and how to hire and grow companies successfully. And, as you listen, you may notice some stronger than normal language due to the excessive amount of WhistlePig Rye …and Porkslap consumed.

For more words of wisdom, see @basker tweets.

Kate Lee

Kate Lee is a Senior Editor at Medium.com; a role which is the perfect culmination of the career path that precedes it. After graduating from the University of Pennsylvania, she started her career as a reporter for US Weekly. However, at a time when the internet had not yet entrenched the magazine world, Kate still turned to it, and the early world of blogs for inspiration. It was in her next job, as a literary assistant-turned-agent at International Creative Management, that this inspiration turned into much more; a niche offering which Kate found a competitive edge while helping to actualize the true potential of some of the prominent voices of the budding digital landscape. However, as the internet grew, what once was the source of her success eventually became her biggest obstacle. When ebooks and Amazon shook that world, Kate made the leap from a 10 year career for something new.

After spending some time consulting and soul searching (and a period of daily afternoon naps), she ultimately found her place at Medium where her current role allows her to continue to give prominent people the opportunity to share their point of view with a global audience. While the entirety of her career was not spent with a digital focus, it was certainly a major influence; one which she is continuing to learn about and directly impact with her gift of finding the industries boldest voices.

To see her in action, check out https://medium.com/@kate or holler at @katelaurielee.

Lockhart Steele

Lockhart Steele has spent his life taking a revolutionary approach to publishing. Even as an eight year old, his passion was well established as he spent his free time breaking local school news stories (by way of a typewriter and photocopier) with two of his friends. However, without many options to explore an academic career in journalism, he majored in history at Brown University, but quickly found his way back to writing when he accepted a position writing for a trade magazine in New York City. From there, the rest is history.

According to him, his career path was not very cohesive, but as we discussed over chilled rose (a bold move for the cooler season), we realized that all of his experiences culminate in such a way which has lead to the success he celebrates today. From breaking boundaries and formats at Gawker, a successful self-published-turned-professionally-published book about jam band Phish (the Pharmer’s Almanac), attempting & failing at his own startup, and ultimately committing to his vision with Curbed – he’s continued to exceed the limitations of the status quo in business, publishing, and writing. Today, after a successful acquisition of his company by Vox, he continues to press his team onward, encouraging them to do the same as the Editorial Director. After all, he attributes much of his progress to the people – the investors, mentors, partners, and teams – who have steered him in key moments of his career and ultimately, whose collaboration have created that “secret sauce” which is so important to the evolutions of innovative products.

Check out @lock and lockhartsteele.com to follow what he’s working on next.

Katie Welch

Katie Welch is the Executive Vice President of Global Brands at Weber Shandwick which is a hefty title and even more hefty responsibility. As a self-described steward of brands, she is responsible for how major companies communicate with their customers on a daily basis. This role requires both a strategic and creative mind, as well as a sound awareness of all of the intricacies of consumer engagement in this fast-evolving space; skills Katie has sharpened over her years of experience both in and outside of the Public Relations field.

Over Absolut Elyx, she shared her path to getting here: beginning with an English degree from Denison University and a passion for fashion & beauty leading to a stint as an intern in the publishing world at Hearst’s Marie Claire. It was this foundation which inspired her to ultimately throw the Hail Mary pass to try to make it in New York and the PR world. However, after many challenges and strategic career moves, time in Chicago and back in New York, and at companies like Macy’s, Victoria’s Secret, and Bliss Spas before returning for her third (yes, third) role at Weber Shandwick — she learned and continues to remind herself of the importance of the details and her advice that is invaluable to anyone in the product world.

For more from Katie, tweet at @KatieWelch.

Gavin Purcell

While it creates exceptional opportunities for growth, one of the biggest challenges in tech is helping older media embrace them, especially TV. Enter Gavin Purcell. As Producer of the Emmy-winning team behind the Tonight Show starring Jimmy Fallon, and before that, Late Night, bringing innovation and maintaining relevance across platforms is a charge he continues to lead. In fact, he and Jimmy have created their own company to ensure that they are able to create digital products – websites and apps – which help bring the show to the forefront of viewers, beyond its nightly airing.

This is certainly not bad for someone who never planned on getting into TV, or tech for that matter, and started his career as a production assistant at the National Enquirer. Over Greenhook Gin from Brooklyn, Gavin shares his incredible story; growing up in Seattle as a “fat kid” who loved video games, he attributes his success to a series of hits and misses – spending time teaching English in Korea, being rejected from grad school, becoming a PA in Hollywood, all the while maintaining the importance of initiative and hard work (even when it comes to cleaning a television studio’s fridge). It’s because of this work ethic, forward-thinking and creative edge, that he has become a pioneer for the integration of tech in the TV world (and vice versa), realizing his “dream job” at G4’s Attack of the Show and now at NBC’s Tonight Show. Bravo!

For more of his musings, check out @gavinpurcell on Twitter and, of course, see the Tonight Show starring Jimmy Fallon weeknights (or, y’know, the internet for the epic clips).

Lara Crystal

Lara Crystal is a founder amongst founders, and frankly, our hero. As one of the brains behind Minibar, she is bridging the gap of all things hot in tech startups at the moment — mobile, on demand services … and alcohol. That’s right, Minibar is a platform she developed alongside her partner, another former Wharton grad, to help connect users with their local liquor stores to help solve for the intimidating experience of going in person and the convenience of having booze delivered to your doorstep in under an hour. At just over a year old, Laura is utilizing app data and her previous experience in marketing and fashion to help take the company to the next level.

Over a couple glasses of sauvignon blanc, we learned how her path, while in seemingly  unrelated fields, has positioned her for this leap into the industry. As an undergrad at Cornell University majoring in business, she had no sights on tech, but instead began her career where most people would like to end it, focusing on retirement (as an Actuary, at least). Fortunately for us, this path was short lived and inspired her to make an about-face to pursue a path of building and making things for herself. From there, she spent many years in the fashion industry, working with brands like Coach, Chanel, and Cole Haan (with a brief stint at business school), but ultimately landed as one of the first hires at Rent the Runway. It was there that she learned while building her first product just how much she could accomplish, and eventually inspired her take her own advice to budding entrepreneurs with an idea: “believe in it and believe it’s gonna work.”

We’ll drink to that.

For an exclusive offer from Minibar, listen to this episode. For more on what they’re up to, follow @minibardelivery and @lecinnyc.

Rafat Ali

Rafat Ali is best known for his coverage of the New York tech scene — which he’s done since dot-com boom 1.0 went bust. However, what’s amazing is that he began his career as a computer engineer, pre-internet in India and found his way into the industry at large by way of a Masters Degree from Indiana University and a personal blog. It’s because of these experiences that he found himself humbly rising the ranks during a tumultuous time at the frenzied start up Inside.com, and finally made his way to covering the industry itself with Jason Calacanis’s Silicon Alley Reporter (just as it’s own print publication went bust). Eventually, and seemingly accidentally, he turned his side project, paidcontent.org, into a must-have for media professionals before even more accidentally turning that into a surprising and swift exit. His experience sums up the evolution of New York new media.

Now as the CEO & Found of his latest project, Skift, Rafat is using the knowledge he’s gained along the way to create a truly profitable journalism product that covers the biggest industry in the world – travel – from a b2b perspective. We’ve learned that 3 years in, Skift is in the black and has three equal revenue streams that give Rafat and his team the runway to build the company that works the way they want it to in a way that benefits both users and advertisers alike. Cheers!

For more from him, follow @Rafat.

Ellie Wheeler

As we’ve learned about the tech industry thus far, the road to success is usually unpaved. This week we learn that becoming a VC is not dissimilar. Ellie Wheeler is a principal at Greycroft Partners, where she is a Series A investor and has been investing in the tech industry for almost four years. However, getting here was not an easy or clear path, in fact, one that she didn’t even know existed. What it took was dropping out of medical school, balancing the world of Private Equity and major corporate M&A, a business school degree and exposure to the startup world filtered through Chris Sacca. Her story is a meticulous experience of writing and rewriting checklists that have helped her get to whatever next step she needed to make.

Over a couple glasses of Merry Edwards Pinot Noir, Ellie shared with us the method to her madness; how in her experience, she has been able to develop a set of standards and keys for success for any startup in this industry, as well as a list of red flags. This, of course, is critical to her as an investor, as she has her finger on the pulse of business and sees trends come and go every six months. And this, of course, is critical to anyone in the early stages of the tech industry — as founders and investors — who are looking to be meticulous in their next steps as well.

For more insights, check out @Ellie on Twitter.

David Kassan

Early in his career, David Kassan lead a double life: interactive art director by day and painter by night. While designing and quickly rising through the ranks of one of dot-com 1.o’s largest consulting companies, iXL, and later at Digital Club Network, an indie music startup, he was simply “paying the bills.” It was when things went awry in the dot-com burst, that David made the bold move to pursue his passion and threw his whole effort into painting professionally. He has never looked back. Fortunately, he did so with a solid foundation; an innate artistic ability, a fine art background from Syracuse University, and gallery representation at Gallery Henoch starting at age 21. It was this catalyst which lead to an unpredictable career path.

Over a couple Sixpoint beers we learned that since then, technology has followed David. From early iPad innovation and real-time painting videos helping him achieve temporary internet fame, to launching his own revolutionary design for The parallelPalette on Kickstarter, to the interconnectedness the internet has afforded the art world, the surprising lessons David draws from his time in tech, how it impacted his painting and vice versa remain valid today for all visual, UX and product designers alike. And, of course, his position on the age old debate — is product design art?

Check out David’s work here or give him a shout on Twitter at @DavidKassan.

 

Caroline McCarthy

Spoiler alert: Caroline McCarthy ended up in tech despite her best efforts to avoid it. It’s true. After sitting down over Pine Barrens whiskey she shared her story of having an innate interest in tech, but after experiencing the isolating and stereotyping that comes with being “that kid” in school, repressed it in favor of just about anything. Not without accolades, of course, this Princeton University graduate (with a degree in the History of Science – what?) and champion rower, found herself without real direction upon graduation. In an effort to pursue her lifelong interest in writing, she entered the working world as a journalist for CNET, covering the budding tech startup scene in New York City. And that was when the gig was up and she was catapulted back into the world she could no longer actively avoid.

Years later her career boasts more than her long standing tech journalism career, but a tech marketing gig at Google, as well, working on projects like Google+. However, after seeing how the industry works on both of these, often very opposing sides, she has decided to join a “startup like” company where she is able to make lasting change. These days you can find Caroline fighting the good fight as the Vice President of Content & Communications at True[X], where she is helping the future of media by calling out the too old smoke-and-mirror games played by the digital display world… and trying to solve for what comes next.

For more from Caroline (and, at the very least, cute photos of her cat Caterpillar): @caro

Chris O’Leary

One of the biggest, and often overlooked, challenges in product and brand building is that of identifying your audience, but beyond that, is reaching that audience. As technology advances and “touch points” are exponentially increasing, as consumers become more savvy, and as companies are being held accountable for their communications, the ecosystem only becomes more and more complex. This week we had the great pleasure of meeting with media strategy extraordinaire, Connections Associate Director at MediaVest, Chris O’Leary, who broke it down for us; how to derive the best value for your advertising budget, the difficulty of measuring against new technologies (::cough cough:: mobile) and the benefit of new platforms, and how we’re poised, more than ever, to actually fulfill those “personas” of advertising yore.

Over beer selections from Westbrook (One Claw and White Thai), Chris explained his path to media expertise; how studies at Ithaca College in Television-Radio/Media Management and his early desire to become a journalist (met with a harsh job market) turned to a career in media. With experiences spanning from a 40 person agency in Burlington, Vermont to 9-figure budgets in New York City, he has sharpened his mind to determine the best way to communicate a brand’s message to the right audience in the right place at the right time. And, of course, marrying that experience to his love of craft beer, leading to the establishment of Brew York (bringing all things craft beer to the masses of New York). But, truly, what chops would he have if he didn’t seize the perfect moment at the intersection of media and technology to have the ultimate viral selfie.

For all things beer and media (not necessarily in order of importance), see @ohhleary.

Caroline Waxler

It’s our opinion that the best entrepreneurs, very simply, are greater than the sum of their experiences, and have found the best ways to extract value from each. Case in point: Caroline Waxler. In her career, Caroline has spanned many industries and roles, starting in the mailroom at Newsweek and using it as a springboard, she ultimately rose through the ranks of the publishing world, working for titles like Forbes and Cosmo. However, she didn’t stop there, and expanded her horizons, both physically and professionally, by moving across the country, she ultimately established herself as a “name” in the freelance writing world. Since then, her writing has transcended the traditional publishing route and has manifested in the form of several highly acclaimed books (see: “Stocking up on Sin”) and successful comedy shows (see: Best Week Ever). But when that wasn’t enough, Caroline joined LearnVest at the ground floor, which is where a spark ignited and she was inspired to create something of her own.

So when Caroline joined us for a custom, Story in a Bottle concoction of Sauvingon Blanc, bitters, soda, and fresh orange juice, (henceforth, the Waxler), she shared with us how creative callings rarely follow direct paths. It’s this pursuit and culmination of experiences which has lead Caroline to be the very capable Founder of Harkness Hall, a conference programming and digital strategy company based in NYC and has helped companies including Google, Forbes, Condé Nast, and Advertising Age program their brilliant live events. (And we couldn’t think of someone with a more qualified background to do it — no joke.)

For more from her, holler at @cwaxler.

Steve Schlafman

In the ecosystem of the startup and tech world, VCs play a vital role to keep the community flourishing; with the ability to coach along the best and brightest into the future, they help to cultivate innovation in many ways. Amongst them, Steve Schlafman is a natural leader. Steve is a Principal at RRE Ventures, focusing on early stage companies in mobile services, hardware, and marketplaces and what he brings to the table is a level of experience and business savvy that is truly impressive.

Steve joined us for a trio of tripels* and helped us dissect this often elusive piece of the business. From his seemingly accidental path into the investing world by way of a love of Nintendo as a kid, to Northeastern University (with an amazing co op program which encourages students to have real world experience while studying), to a stint with Microsoft and the New England Patriots, and eventually getting his foot in the door at Lerer Ventures, he has been able to refine his knack for successful business ventures and worthy founders. He explained to us why sometimes even the best ideas get passed over for 2 rounds of funding only to ultimately receive his support and what makes a standout founder in this day and age. If you are in any stage of raising, consulting, or pursuing a portfolio of your own, his is a perspective worth investing in.

For more from Steve, consult @schlaf on Twitter and check out his Guide to NYC Tech and Raising Seed Capital.

**Allagash, St. Bernardus, and Westmalle Trappist

Christina Wallace

Christina Wallace is a tried-and-true “jack of all trades.” A self-prescribed generalist, she’s made the successful leap through many different industries and roles; from degrees in mathematics and theater from Emory, to “diva management” at the opera, to Harvard Business School and founding her first company, Quincy. And while her path was winding, it’s very much by design. Refusing to focus, she’s set out to “do” all of the things she loves, drawing parallels where they exist, which have ultimately culminated as her dream job as the Founding Director of BridgeUp: STEM, a new educational initiative at the American Museum of Natural History focused on introducing girls and minorities to computer science.

But no great story is without its challenges. Over whiskey gingers, Christina gave her candid account of how to make it work and what she did when it didn’t (like at a $1MM company that was failing, for example). She reminds us to be resilient, what REAL networking is, and proof of the power of the Violence of Articulation. And through her efforts, she continues to inspire us that the future of tech is a bright one.

For more on BridgeUp: STEM, which has it’s first cohort of new after-schoolers starting this month, see: http://www.amnh.org/learn-teach/grades-9-12/bridgeup-stem/brown-scholars

And, of course, hit up @cmwalla. Tell her we sent you.

Matt Lee

Matt Lee is currently a Senior Usability Researcher for Booking.com, but in his remarkable career, he has played many other roles: a Business Administration graduate, a field researcher representing companies like Canon… and Vicodin, a Usability Engineer for the first Xbox live and Amazon, and User Researcher Manager at Zappos. More than that, however, he is a true advocate for the betterment of the internet, championing the important learnings he has acquired about user behaviors and bringing them to the forefront of each product he’s worked on.

In this episode, we sit with him over a bottle of Hibiki (a Japanese Suntory Scotch) and we hear his story; the good, the bad, and the very very awkward moments that come along with user research. What we learned, is how the digital world is changing; from people not knowing how a mouse works (seriously) to the exponential growth from products to devices and how data can and should be at the core of all innovation. He maintains that more than ever before  “it’s less about getting from A to B.” So, if you’re building a new product or growing an existing one — you’ll certainly want to hear this.

And if you want even more from him, hit him up @mleeconsulting.

Lindsay Kaplan

This week is another first for Story in a Bottle; for the first time we are hearing the point of view of the arguably unfairly named redheaded stepchild of the internet, social media. (We’ll pause while you process that.) But seriously, who better to represent it than one of the internet’s most beloved redheads, Lindsay Kaplan?

Lindsay joined us for Glenmorangie scotch and shared her experience of growing into the world of social media and communications. She started by way of an English Philosophy and Creative Writing Degree from Brandeis and dreamt of a future in editorial writing. However, a chance interview steered her in another direction and she never looked back. Since then, for better or worse (and we’ll say better), she’s had a host of publishing and PR jobs, including becoming the first Social Media Manager for ELLE. Through the challenges of being on the forefront of social and having to continually prove herself as a worthy seat at the table, Lindsay has certainly triumphed and has invaluable advice to share with the very much lagging industry. After all, it’s this insight and being headstrong that brought her to her current role as VP of Communications at Casper, a sleep startup. We learned so much from our conversation with Lindsay and hope you do too.

For more from her, check out @lindsaykap and @Casper.

Steve Martocci: Part Two

Last week we met with Steve Martocci and heard about the challenges of being a first time founder in the early stages of a tech startup. This week, he continues his story (as he and Dan finish the bottle Angel’s Envy bourbon) about the evolution of GroupMe from $850K to $10MM and what that growth meant. This is when it gets real.

He walks us through their growth, utilizing groundbreaking PR tactics at SXSW, to raising vs. partnership conversations with major players in the space, and finally becoming one of New York tech’s biggest exits to-date (and life beyond that acquisition). Steve’s candid account offers invaluable advice for investors and founders alike, and moreover, insight into the very nuanced and complicated realm of the startup world. (We’ll drink to that.)

For more from Steve, holler @smart and see his newest product Splice.

 

Steve Martocci: Part One

Steve Martocci is the co-founder of Splice, a technology platform for music creators which streamlines the fragmented process of creating and sharing music, freeing musicians to spend their time and energy on the creative process. Previously he was a co-founder of GroupMe, a group messaging service that in August 2011 was acquired by Skype, which was subsequently acquired by Microsoft in October 2011. Prior to GroupMe, Steve was a lead software engineer at Gilt Groupe and founded Sympact Technologies and Bandwith.us.

However, it was over Angel’s Envy bourbon that we learned that Steve’s success can really be attributed to the breakup of Phish. Of course, he had all of the accolades to garner a successful career, Steve graduated from Carnegie Mellon University in 2004 with a B.S. in Information Systems, and has had a string of high profile tech jobs with amazing collaborators which give him his business-savvy and tech know-how. However, it was his love of music that has motivated him and remains a constant thread across his  career.

In part one of our (first ever!) two-part story we learn a lot about those early days in his career and the catalysts that set his trajectory toward the tech superstar we know today.

Naama Bloom

It’s said that true innovation is the reduction of complexity, and if that’s the case, Naama Bloom is an innovator amongst innovators. Most recently acclaimed as the woman who brought the period to virality status, she has made a business of taking the often overly complex conversations of women’s health and milestone moments (which were reserved for whispers or clinical jargon) to the tens of millions of views on YouTube and furthering it to content and newsletters via her company HelloFlo. However, while demystifying these conversations amongst women seems like a “no brainer,” it is not without a sharp strategic mind and business savvy that it has been executed.

As a tech vet, for better or worse earning her nickname as “the Closer,” Naama spent majority of her early days jumping from digital company to digital agency and over again as they folded in the early nineties, which inspired her to eventually go to Cornell Business School. Upon completion, she emerged with more solid footing in the business world and began to climb the ranks as a marketing executive at both American Express and Harvest before she was inspired to take on founder life full-time.

Over a bottle (or two) of red Zinfandel from Sonoma County, Naama shared her experiences of starting a company with just a great idea and great chutzpah, the importance of choosing a cofounder with complementary skills, and the painful battle of raising money while trying to build a brand (and the battle of maintaining a two founder household with her husband, David Bloom). True to her nature as an innovator, she tells her story without euphemism or pleasantries and for that and more, she is truly commendable.

For more from Naama, she tweets as @NaamaBloom and be sure to check out Camp Gyno and First Moon Party on YouTube.

 

Gene DeRose

We at SIAB call Gene DeRose the “O.G. of the New York Tech Scene.” In his 25 year career here, he’s surely seen and been a part of his fair share of the evolution of the industry. Hailing from Westchester and going to school in Virginia, he landed back in NYC originally in the pursuit of journalism. However, as the tides shifted, he steered a new course (well, with a brief stint as a bartender) and became the co-founder of Jupiter Communications; taking it from a newsletter to the media success it became, and then taking it public. Beyond that, he’s consulted and founded a number of interesting projects, harnessing digital-virtual power and bringing it back to the real world with both Mouse and House Party.

Gene joined us for Herradura Añejo on the rocks (with a little lime) and bestowed his saga; from those early journalistic experiences, surviving the “digital winter” of the mid 2000’s, taking a company public (and maybe not doing it soon enough), making good and bad investments, and the “borderless internet” he’s working towards now. Gene’s is a true founder’s story and we can all take a page from his experience.

You can find Gene on Twitter @genederose.

Kristen Hawley

Kristen Hawley has one of the most diverse and inspirational stories we’ve heard to date. With a journalism degree, background in media, love of epicurean culture and experience dabbling in the tech world, she’s created a path for herself which only begins at the intersection of these things. However, her agility and strategic perspective has lead her to create Chefs + Tech, offering an interesting and unique spotlight on the emerging technology trends in the culinary world.

Kristen has certainly earned her chops along the way by navigating various industries and cities; circumventing the treacherous publishing and media world at Hearst in New York City and skimming the tech scene at PopSugar and Twitter in San Francisco, she ultimately decided to combine the two things she’s most passionate about – food and media – to create her ideal job. Her story encourages us to follow our gut and remain adaptable, and do not be fooled. What she calls “luck,” is really her tenacity to adapt quickly and to create the next best opportunity (when it otherwise doesn’t exist).

Oh, and she changed our minds about Pinot Noir, as well!

Get in on the latest on Chefs + Tech here. And more from Kristen: @kh.

Richard Blakeley

In this week’s episode we hear from Richard Blakeley who is an award-winning internet innovator and entrepreneur. However, most noteably to us, Blakeley has pursued a career of pushing the boundaries of content as he navigated through the digital world; starting with a personal Live Journal, to founding the over the top food blog turned book This is Why You’re Fat, and eventually rising through the ranks of media world as Editor-in-Chief of Gawker.TV and heading Content & Strategy at Thrillist. Not to mention, he extends the limits of the online realm as the founder of Internet’s biggest annual party, The Webutante Ball.

He joined us for 2 bottles of Sauvignon Blanc (prompting him to suggest our show be called ‘Story in a Bottles,’ touche) and he recounted to us how his relentless drive to see ideas through myriad experiences has helped him disrupt the status quo of both content and digital products, and reminded us that so long as you’re learning, no day is ever wasted on the internet. Cheers to that.

For more from Blakeley: @blakeley

Soraya Darabi

This week’s episode features our friend Soraya Darabi, the co-founder of Zady. Zady is the online destination for conscious consumers. They source and sell and make stylish apparel for men and women, and detail the stories and origins of the items produced. Much more than a fashion startup, her company is a brand and a movement towards responsible manufacturing, global sustainability, and human rights in the apparel industry.

However, before that, we follow her journey from working as a College Marketing Rep for Sony Music, to jobs in media, both bringing journalists at The Washington Post into the digital present and discovering the NYC tech world while at Conde Nast & The New York Times. Ultimately, she found her way to become an entrepreneur at startups like drop.io, foodspotting and now Zady. Her path is in no way ordinary and extends beyond the “tech socialite” description she’s been ascribed. Oh, and she also offers up the secret to a mean mango mimosa.  

Hit her up with follow up questions at @SorayaDarabi.

Rex Sorgatz

Rex Sorgatz is a jack-of-all-trades; self-described as a media collector, product strategist, creative technologist, culture hacker, writer, designer, advisor, and consultant, but who is currently spending his time as the Founder & Partner of Kinda Sorta Media.

He joined us for homemade cider, which he made and provided (a SIAB first), and told us about his very fascinating path; from starting as a Pultizer-prize winning journalist in North Dakota to working at a print magazine ABOUT the internet (yes, this is a thing), and how he became @fimoculous. From there, he’s made his way through different parts of the digital industry, with “view source and hack it backwards” beginnings, and offers a unique point of view because of it. At the end of the day, Rex is fighting the good fight to find the balance between being an expert or generalist (and probably both).

Rex’s musings can be found here and he also contributes to a Medium group dubbed the Message.

Christina Mercando

Christina Mercando is the founder of Ringly, a wearable technology company based in Brooklyn, New York which launched in June of this year. However, with 10+ years in the technology industry, Christina has taken quite the interesting path to get here.

She joined us for sparkling wine and shared her early experiences in tech; helping her dad manufacture medical CD roms in their home in Irving, New York and her days working through video projects at HCI at Carnegie Mellon. Christina ultimately found her way into the professional realm working in the music marketing industry and finally doing user experience and design at Hunch, which was later acquired by Ebay.

However, Christina always had the ambition to do her own thing. Now, with Ringly, she’s able to take the lessons she’s learned in working in both large- and small-scale companies and continues to evolve with the future of technology. To other entrepreneurs: “take a risk if you can.”

To hear more from Christina, follow @jetpea on Twitter.

Tom Clifton

Tom Clifton is co-founder and head of B2B at Animoto, a subscription-based web and mobile platform that enables businesses and consumers to create dynamic, professional videos. Launched in 2007, Animoto has grown through several rounds of funding to over 10 million users and has won every major industry award, including two Webbys, a Crunchie, and a SXSW Interactive Award, as well as being chosen as Crain’s Top 25 Best Places to Work in New York City.

However, getting to this point has not been without its many steps; Tom joined us for Negronis and told his story — his tech beginnings as a 12 year old in Seattle pitching & building websites with his brother, an academic career including bible, computer science & music schools, and ultimately co-founding Animoto with a group of entrepreneur friends. All the while learning that building and working with a great team in order to make a great product is one of the keys to finding balance as an innovator.

For more on what Tom’s up to, check out @Animoto.

Amanda Peyton

Amanda Peyton is the co-founder of Grand St., a marketplace for creative technology that was recently acquired by Etsy. Peyton is a technologist at heart and has worked at the intersection of technology and design for her entire career. She is an alum of MIT Sloan, Northwestern & Y Combinator and currently lives in New York City. But that’s just scratching the surface.

Amanda “classed it up” with Bulleit Rye on the rocks and shared her beginnings as the “5th grader with the side hustle,” living in China, becoming the “queen of the geeks” in Texas, and ultimately her three-startup-strong experience. All the while maintaining a DIY, entrepreneurial spirit and embracing the mess of the startup world by seizing the opportunities it has to offer. Her story is certainly as bold and strong as her drink of choice – cheers!

You can check out more of her musings on the internet via @amandapey.

Scott Beale

Scott Beale is the founder and primary tentacle of Laughing Squid, as well as advisor to Selfie.com and All Power Labs. Scott took his early beginnings in film to create one of the biggest art, culture and technology blogs and hosting companies (which boasts a record 1MM visits in a single day). From growing up and delivering pizza in Dayton, Ohio to pursuing a documentarian career to a stint at Burning Man and ultimately growing Laughing Squid to where it is today, his experience is both entertaining and inspirational.

We joined him for his favorite cocktail, the Bloody Gin and Tonic (made by his wife, Lori Dorn), to hear his perspective of the industry but found even more with his insightful perspectives on authenticity, sensationalism, memes, and common mistakes on the internet.

You can hear more from him on Twitter at @ScottBeale.

 

 

Brooke Hammerling

Brew Media Public Relations founder, Brooke Hammerling, has created one of the go-to PR companies in the tech world. Her clients have included GroupMeGeneral AssemblyOracle & Refinery29 and her philosophy about working with growing companies – young or old – is one any leader could learn from. Her path to where she is, from growing up in the suburbs of New York City to founding the company from her apartment on W10th Street in NY’s West Village, was not a predictable one. We sat down over “the wine of the Gods”, Domaines Ott Château De Selle Rosé Coeur de Grain and talked about how she went from an early ’90s club kid without direction, to one of the most successful, creative and innovative voices in tech. 

You can hear more from her on Twitter at @Brooke.

SPONSOR: This episode is brought to you by SUMO Heavy, a premiere NYC development and consulting firm specializing in eCommerce. SUMO is growing their team and looking for talented developers. Apply now at careers@sumoheavy.com with the subject line Story In A Bottle.

Rick Webb

Rick Webb is currently the VP of People Operations at Percolate and one of New York’s most well known and respected figures in technology. As the co-founder of The Barbarian Group, an angel investor, a partner at Quotidian Ventures and a mentor to so many, he’s been a fixture of the tech world for over a decade. We had he pleasure of talking to him for our innagural episode. For an hour, over a Malbec mixed with soda water (Rick’s drink of choice), we heard about his upbringing in Alaska, his migration east and the lessons he’s learned by going with his gut.

You can find him on Twitter at @RickWebb

SPONSOR: This episode is brought to you by SUMO Heavy, a premiere NYC development and consulting firm specializing in eCommerce. SUMO is growing their team and looking for talented developers. Apply now at careers@sumoheavy.com with the subject line Story In A Bottle.