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Caitlin Thompson

Tennis has always been a passion for Caitlin Thompson, and now she is able to hone in on that passion with her own magazine, Racquet. From a young age, she knew being on the tennis court and telling stories were two things that just came natural to her. She continued those two natural feelings by playing tennis for the University of Missouri, which also happens to be one of the best journalism schools in the country. She went on to lead a very fulfilling life in journalism, writing for newspapers and magazines all over the world, and even though our world is shifting more to digital, nothing compares to the excitement and dedication to her own print magazine, and how she feels destiny has brought her two favorite worlds together into one.

What You’ll Learn:

– Why Racquet is is so important for such a small community (5:10)
– How money is valuable and media should not be free (28:54)
– Why tennis has always been written on a spectrum of utility instead of about the people (30:37)
– How Racquet is putting tennis players back into the cultural conversation (39:06)

Ilir Sela

Growing up in the Albanian community of New York, Ilir Sela was poised to continue the age-old tradition of owning and operating a local pizza shop. But simply following suit was not enough, and, as he grew and advanced in his technical skills, Ilir became the go-to in the community for all things IT related, starting with websites and online ordering, but later realizing the shifting needs of the industry, not only in New York, but nationally. It was this unique circumstance that equipped him to create a major platform to bring about the evolution needed to keep these local businesses connected with the communities they fed. As the founder of Slice, a digital ordering platform, he is constantly finding new ways to do this and to continue to ensure that this community staple finds it’s place in the future.

What You’ll Learn:

– Creative ways to garner interest in tech in an industry that has existed without it

– Why the local pizza shop industry deserves a different solution than big ordering platforms

Kate Gardiner

It goes without saying that the more connected we’ve become – the world, and the events reported around it, have changed; with information traveling the fastest it ever has, the role of storytellers has evolved and there’s nothing that stands in the way of telling the goings on from every which end. And still, while the world continues to get “smaller,” it’s becoming continually challenging to know the happenings taking place in your own neighborhood. Kate Gardiner has spent her many years in and around the journalism world being a voice from an often unheard vantage point – whether it’s reporting in the isolated community of Molokaʻi or growing a network of professional women via theLi.st – and even in her work today as founder of audience engagement firm, DSTL. Kate’s goal is simple: to build bigger and better communities and to connect them with the information they need to continue to grow.

What You’ll Learn:

– The importance of getting the right story to the right audience

– How lack of innovation in local news has failed local audiences

– A tale of evolving entrepreneurship, beginning with exotic fish sales

Michael Cerveris

It’s safe to say that while the entertainment industry is so ingrained in our daily lives, it’s inner workings and the lives of those in it are elusive to most. Over drinks at Fool’s Gold, Michael Cerveris gave us a glimpse behind the scenes including all of the exciting, high parts of his career: headlining a banner Broadway show, winning Tonys, making breakthroughs in television. However he also shared how in acting, much like other industries, even when you achieve a certain level of success, imposter syndrome is nearly impossible to avoid, and why he approaches each new project as way to start over again. And Again. And again.

What You’ll Learn:

– How to maintain enthusiasm for a job even if it seems like you’re doing the same thing over and over every day.

– Why “losing” can ultimately be better for your career.

– How imposter syndrome affects other industries.

Jennifer Wright

Jennifer Wright began her career – with a passion and innate skill for writing – and during a time when content on the web was hitting critical mass, allowing personality and perspective to shine through unlike any time before. She boasts experience with publishing powerhouses like the New York Post, Cosmopolitan, and Glamour – as well as authored her own acclaimed books. We caught up with Jennifer at Fool’s Gold in New York City and over Snake Bite Violette’s she talks about how she got to where she is, what has inspired her writing thus far, and how the shift in our political atmosphere has ignited in her a new approach to her writing that she never expected.

What You’ll Learn:

– How to pursue a passion in writing without being defined by your “beat.”

– The new responsibility all journalists and content creators have in producing content and the necessity to consider global context

Ben Hill

Ben Hill was a student not unlike many others; getting into school and choosing a path that seemed to make sense and not questioning why. It’d only make sense that when he graduated from Pitt with a degree in Communications he was left wondering what to do next. Over Teeling whisky at Fool’s Gold, Ben talks about the roundabout path he took to get to where he is today – the voice of an important aspect of Americana writing about Minor League Baseball – and the impetus for his blog “Ben’s Biz,” 12 years ago.

What You’ll Learn:

– How Minor League Baseball impacts American culture beyond the sport.

– What it’s like to create a new niche in journalism.

Kristen Hawley: Part Two

When Kristen Hawley set out to create her newsletter, Chefs + Tech, she had years of publishing and tech experience under her belt (spending time at Hearst, Pop Sugar, and Twitter in her early days). As such, as a founder, she always dreamt C+T would be part of a bigger editorial platform and, as of a year ago, that dream was becoming a reality. Joining us for the second time in the Charming Robot offices over Pinot Noirs, she fills us in on the last year of Chefs + Tech: being acquired by Skift and the challenges of a founder (and new mother!) in this position, how C+T has grown since joining the Skift ecosystem, and finally, to share the news of its latest iteration: Skift Table, which is officially launched at the Skift Forum in New York City last week.

What You’ll Learn:

– How to start and evolve a product that you have large aspirations for.

– The questions you should ask (and answer) as a founder with the prospect of being acquired.

– How becoming a parent influences all of the above – and then some.

Anthony Batt

Anthony Batt, Co-Founder & Executive Vice President of VR company Wevr, obviously spends much of his time thinking about future innovations. However, it’s this curiosity that has been a driving force through much of his life and career – leading to the creation of products like Craigslist, Buzznet, and Thrash Lab, amongst others. Over La Croix Pure in his amazing office – former home to Dennis Hopper in Venice, CA – he explains his challenge of always thinking many steps ahead while waiting for technology to catch up and how this is especially true now in the lifecycle of VR.

What You’ll Learn:

– Why sometimes being first in the world of tech does not always guarantee your success.

– How solving a problem can lead to creating a product, even when you don’t mean to.

– The challenge of creating content and products that you know are too early for adoption – and the key decisions to make in this circumstance.

Christina Heller

Christina Heller is the Chief Development Officer of VR Playhouse, a creative production studio based in LA which is dedicated to creating great content for virtual reality experiences; a company she co-founded in 2014. It’s an industry she’s found by way of her love of storytelling, with a background in theater, political journalism radio, and documentary filmmaking. Over micheladas, Christina shares her thoughts on the budding industry, how it’s suffered because of unrealistic expectations set by those within it, the obstacles that still need to be overcome in order for it to reach mass adoption, and some of her great experiences creating content (which may or may not include a run in with one of her heroes, Ken Burns).

What You’ll Learn:

– Why VR is far from “dead.”

– Insights into developing some of the first VR experiences for Time, amongst others.

– The future of virtual experiences – and how you can eventually date without leaving the privacy of your own home.

Adi Levanon

As VC who invests in early stage companies – Adi Levanon of Symmetrical Ventures embraces the opportunity to help grow companies from the ground up. In fact, growing up in Silicon Valley with visionary-type parents, she was poised from an early age to enter the industry. However, she attributes a lot of her success to her time living in Israel, serving in the military, and later becoming a lawyer. Over mezcal margaritas at Fool’s Gold in New York City, Adi enumerates how “everything I’ve done has lead me to what I am doing now” – including sharing her daily experiences in her own podcast “The Adi Tells” podcast.

What You’ll Learn:

– How to take a headstrong approach to entering a new field and finding a job in a new city.

– Why learning you’re not a fit at a company is not a failure.

– The value of working with investors who understand your industry.

– Mistakes to avoid when you pitch.

Alexander Reyna

Alexander Reyna is the Creative Director, Games and VR at MLB Advanced Media – whose primary role is to help bring to life the most innovative ways to put baseball content into the hands of its passionate fans. It’s a role that suits him well, as it intersects his entrepreneurial spirit and his design background, dreaming up big ideas and solutions as technology evolves. However, the road to get there was not without its perils. Over The Main Brewey’s Tiny Beautiful Something at Fool’s Gold he talks about the many failures and obstacles he overcame as an artist in his early career, his entry into tech from the gaming world, and how those experiences shape the work he’s doing today.

What You’ll Learn:

– How to take an entrepreneurial approach to the product design process

– Insights into how the tech and design industry has evolved

– Learning how to thrive beyond “failure”

Emily White

Emily White is the co-founder of Dreamfuel and Whitesmith Entertainment, two companies helping musicians and athletes achieve their goals. However, she began her professional career as a competitive swimmer. Born into a family of athletes, it only made sense that Emily attempt a stint in the pool but, when her interests deviated to the music world, she resourcefully used her competitive career as a springboard to get into the program of her choice at Northwestern. Over mocktails at Fool’s Gold in NYC, she describes her path through the music world – where she’s experienced almost every role in management from touring to talent – and how it’s lead her full circle back to swimming, as she contributes in a way she could’ve never envisioned.

What You’ll Learn:

– The important career lessons one can learn from jam bands.

– A woman’s perspective to the perils and biases encountered while fundraising.

– How understanding each part of your business is fundamental to being a strong leader.

Phillip Bowden

Phillip Bowden has spent over the last decade entrenched in the world of tech; arguably the most evolutionary period in the industry’s history. What’s more, he’s experienced its growth from several key vantage points. From his earliest experience with computers – by way of tinkering around on a household PC he wasn’t supposed to – he essentially dove into the field in early development roles at Gowalla and Tumblr. However, when friction within the industry increased, he ultimately decided to do his own thing, co-founding consultancy Brooklyn Computer Club with Buzz Andersen. Over Penicillins, he explains the challenges of this ever-evolving industry and his shifting role within it, even today as he helps tech darling Spotify continue to grow.

What You’ll Learn:

– Why having more people on a team doesn’t ultimately solve a problem faster.

– The pros and cons of working in the tech field with little formal tech education.

– Insights into working for both early stage and larger companies – and the benefits of each.

Jess Brown

When Jess Brown got her start with computers she spent her time designing for fun and trolling chat rooms online – seemingly a world away from a career in the then fledgling user experience industry. In fact, it was her love of math and the practical application of it at Stanford University that set her in motion. Over an Aperol Spritz, Jess tells us about those early days in a nascent industry, how she was able to guide her first gig with user research and why that lead her to join other startups like Threadflip and Rent the Runway. Today, she is Head of User Experience at Vice – applying the knowledge she’s gained along the way to this ever-expanding, content behemoth – which is no small task.

What You’ll Learn:

– Why test methodology matters in user research – and the importance of determining which is appropriate for understanding the specific user behavior you are testing.

– Why founders of companies may not necessarily need to be their end users and how that impacts design decisions.

Khayyam Wakil

Khayyam Wakil boasts a career with an unbelieveable trajectory – all thanks his ability to identify and capitalize on trends. From Saskatoon, Saskatchewan, Canada, he rose to Twitter fame in the early 2000s, but what he didn’t know at the time was that his lighthearted exercise in gaming the platform would actually lead to true social influence. Over Malopas (mezcal palomas), he explains just how he became one of the 5% creating content on Twitter which lead to being one of the few selected to be a part of the UN’s envoy to curing malaria and how those experiences, in addition to his time in VR, have shaped his take on both activism and tech. This is especially important today, as he aims to bring more “first hand” experiences to the public in his latest endeavor as Head of Creative Partnerships at Live Planet.

What You’ll Learn:

– The pros and cons of the “empathy machine” that is tech and Virtual Reality \

– Why sometimes having the propensity to learn is far more powerful than a linear path in education

– The unfortunate truths about how social media has changed activism

Bianca Bosker

Bianca Bosker is a journalist and nonfiction author whose body of work truly runs the gamut; from bowling to covering tech for HuffPo and spending a decade plus becoming an expert in Chinese “duplitecture” and beyond – it’s a career that appears to have no rhyme or reason. However, over Sage Beers at Fool’s Gold she helps explain the method to her madness – that, as a storyteller, she’s found true the old adage that “truth is stranger than fiction” and her obsessive nature helps her get to the heart of these truths. This is especially the case for her latest, bestselling book “Cork Dork” which chronicles her choice to drop everything and start at the bottom of the wine industry as “cellar rat” to endure the challenging path to certified sommelier.

What You’ll Learn:

– Behind the scenes of the early days of HuffPo’s tech coverage – and their thesis for differentiation

– The ins and outs of paving one’s way in the often elusive wine industry

Preston Pesek

In the startup community – from founders to investors to customers and employees – the first question that should be asked is “does this product solve a real problem?” Enter Preston Pesek, the founder of Spacious, a coworking company that aims to answer “yes” to solving not one, but two problems in major cities. Over Micheladas, Preston describes the painstaking process he took to identify and solve the problems of an ever-growing and displaced coworking crowd, as well as the vacancy of off-hours restaurants; with beta testing and shifting business models to transforming physical spaces – it’s a product that attempts to benefit all parties, and ultimately a story that shows how a real product process can lead to success.

What You’ll Learn:

– How to approach being a first-time founder

– The value of knowing what skills you possess and how to hire for those you don’t

– Understanding how to create a product that addresses a real problem vs. creating a problem to fit your product


Beth Newell & Sarah Pappalardo

Often times in our increasingly divided and contentious society, for better or worse, comedy is the only and best way to actually be heard. It’s something that Beth Newell and Sarah Pappalardo, co-founders of Reductress.com, know first hand. Dubbed the “the one and only fake women’s news magazine” – through its satirical content –  Reductress aims to raise awareness of feminist issues. Over Bell’s Oberon Ale, Beth & Sarah talk about how it came to be and how their roles have evolved during its lifespan and the method to their madness of creating relevant content on a daily basis.

What You’ll Learn:

– Why, more than ever, fake news may be EXACTLY what we need to understand important issues

– Why being the “Oprah of satire” is the ultimate goal


Sutian Dong

Sutian Dong, Partner at Female Founders Fund has spent much of her career in the Venture space – getting her start in Business School at NYU Stern and early experience at First Mark Capital thereafter. However, it’s a path that was not always so clearly defined for her. Over mezcal at Fool’s Gold, she explains her unique process of elimination in pursuing this direction, how it ended up getting her into venture during some of the key, formative years of startups and tech in NYC, and how it’s culminated to her unique position at Female Founders Fund today.

What You’ll Learn:

– The experience of starting in VC when it was the “step cousin” to private equity and other, more “trendy” finance roles

– What key things VCs want to hear from founders

– Why diversity matters in company cultures and how it correlates with success

Jacob Lewis

Jacob Lewis spent much of his early career in publishing – at the helm of the New Yorker and Conde Nast – during one of the most transitional times in the industry’s history. It was a vantage point that revealed a bird’s eye view of evolving processes and the eccentricities of staff – and ultimately the folly in flailing and dying publishing behemoths. It’s an experience that inspired him to do an about-face and embark on a company on his own – to pursue a path in tech. Over whisky (AND beer) at Fool’s Gold, he explains the challenges of establishing that first company, Figment.com, the lessons he’s learned along the way, and how he’s applying them to his latest endeavor – restaurant rating platform, Renzell.

What You’ll Learn:

– A story of amazing career growth – from working in the mail room to executive levels.

– Behind-the-scenes insights about the challenges of evolving with tech in the publishing world.

– The importance of nuance of the service industry in reviews.

Brad Lauster

With the major growth of the tech industry it’s never been easier to become a specialist; from hardware to software, design and development, bootcamps and formal degrees there are no shortage of avenues to take to lead you into your career. This is much different than the opportunities Brad Lauster had when his passion for technology began – as he worked his way from the ground up copying printed programs from Atari magazine. Over Sazeracs at Fool’s Gold in NYC, he shares his wealth of experience in both hardware and software, design and development roles spanning across companies like Intel, Stanford University, Equinox – as well as starting his own product, Bindo – all while making the web a better, more usable tool. This experience is especially important today, as he leads product design at Weight Watchers and helps to bring this aging company into a more engaging future.

What You’ll Learn:

– What key characteristic all User Experience designers should have.

– The pros and cons of working for large companies.

– The first step to approaching a career in tech.

Jo Piazza

Jo Piazza is an award-winning journalist and writer – known for her approach to covering the behind the scenes perspectives of the world’s most taboo or inaccessible topics. From fiction to non- she’s explored a lot of unchartered territory; the world of celebrity endorsements to the elusive lives of nuns and the leaders of a nascent tech industry, and most recently behind the closed doors of marriage. Over mocktails at Fool’s Gold in New York City, she explains how her passion for telling the stories that are not often told was a trajectory set when she was a curious kid growing up in Philadelphia – getting the scoop on locals at a neighborhood bar. It’s certainly a methodology we can raise a glass to.

What You’ll Learn:

– How Instagram is ruining marriage.

– The challenges of being a full time writer in 2017.

– How talking with people in bars can lead to a successful career.

Bart Mroz

As the tech industry has evolved there is one thing that has separated those who have been successful from those who were not – and that is their adaptability to change. This is a quality that Bart Mroz, CEO of SUMO Heavy Industries, has exuded nearly all his life – since the young age of 12 when he came to the US from Poland without being able to speak a word of English. Since then he has experienced myriad roles in tech – often bearing the burden of being the spearhead of a nascent discipline within older companies and continuing to evolve after he set his sights on a more the entrepreneurial path of running his own company.

What You’ll Learn:

– The value in channeling a “you just gotta learn” attitude in uncertain moments of your life and career

– How major loss can be beneficial to shaping the future of your business

– A unique perspective of immigrating to the US and how that experience helped lead to a career of entrepreneurship

Sehreen Noor Ali

At the height of the information age, emphasis on education is also at an all-time high and conversations about the best approach and paths to success are in abundance. Sehreen Noor Ali, VP, Business Development at Kaplan, not only confronts this from a business perspective, but has been considering the multitude of options for many years. Over grapefruit spritzers, she recalls her personal path through formal education, with many years of post graduate studies and nontraditional, as she learned during her days at the State Department, and finally now, as a mom who is looking for the optimal environment for her daughter to thrive. It’s certainly not a one-size-fits-all model, which has benefit from her warrants consideration ensuring her continued success.

What You’ll Learn:

– How governments use social media to impact diplomacy

– The importance of understanding your learning style – finding the right way to maximize it

– How education has had to adapt in the world of digital

– Why you should worry about being well-rounded vs. well-educated

Alex Zalben

When it comes to content – on the internet or otherwise – people usually fall predominantly into a category of “consumer” or “creator,” but can you be both? Alex Zalben’s passion for entertainment started at a young age – with a love of Monty Python that overshadowed his apprehension of public performing and a desire to write that catapulted him into a career of sketch comedy. However, over time and experience in both the comedy scene in NYC and professionally at Marvel, MTV and TVguide.com, he’s used his unique perspective to blur the lines and stay true to both aspects of his passion – a true appreciator (and self-proclaimed nerd) of the art he loves and a contributor who furthers the art himself.

Arikia Millikan

Arikia Millikan is a journalist and entrepreneur with a resume that boasts digitizing traditionally print-centric brands. It’s a career that’s given her a fair share of behind-the-scenes experiences with the epidemic that’s overtaking the industry – the continued and steepening uphill battle of maintaining the right motivation in the world of news and content. Over Bloody Marys (with a fun twist) at Fools Gold in NYC, she explains how her unique approach in applying engineering principles paired with a “squeaky wheel” reputation help her press forward and innovate within this challenging space.

What You’ll Learn:

– The harm in not keeping balance in the separation between content and revenue in the world of publishing.

– Why it’s valuable to apply approaches from other disciplines when innovating and evolving media.

– How improved tools can make all the difference in quality content creation.

Austin Smith

If you’ve ever dreamed of your hobby becoming a career, Austin Smith’s story will resonate with you. Growing up in Des Moines, Iowa, Austin’s earliest interest was music, which led him to be the music director at his dad’s church at the ripe old age of 13. Going on to study music Washington University, technology was just a side interest that he didn’t know could be a career.

Over Zinfandel from Ridge Vineyards, Austin talks about the most formative experience of his career, how hacking his customer service job with technology helped him realize that maybe it was time to turn that side interest into a job, and how working on technology for The Observer and The Economist led him to form Alley Interactive with his business partner, Matt Johnson, to simplify life for the people creating journalism and to help people connect with the world around them.

What You’ll Learn:

– How going with your gut, being willing to figure it out as you go along, and partnering with the right people can lead to a great business.

– How working in a service job early on helps you relate to people throughout your career.

Alex Leo

Alex Leo is a news content and product development expert – with a resume that includes roles at ABC news, Reuters, and most recently as VP of Audience Development at the Daily Beast. And while there’s no shortage of great experience in the field, as it turns out, her education in the space began much earlier. Growing up with two writers as parents – her mom for Family Circle, amongst others, and her dad taking on conservative media – she began thinking about content at an early age. Over white wine spritzers at Fool’s Gold in New York City, Alex recalls her first steps into the industry, beginning with a traumatizing experience in visiting colleges with her parents, to pursuing english at Wesleyan University, and ultimately leading to her latest position – essentially a front row seat to observing the unprecedented and controversial marketing tactics used in the 2016 election cycle. She has a unique perspective that can only be forged by a lifelong relationship with the news – and one that has her poised for her next endeavor – starting her own thing to influence real change in the criminal justice realm.

What You’ll Learn:

– What “dark post” means and how it helped Trump win the election

– How to combine your professional skills with a personal passion to make a career move

– Why large media companies would do well if they adopted a startup approach to innovation and digital product development

Gabriel Snyder

As technology has evolved, the distribution channels for audiences and consumption of content are at an all time high, the world of journalism is facing unprecedented pressure to “evolve or die.” This problem, however, is not new. It’s an ongoing struggle for balance that’s existed since news organizations appeared online over two decades ago. No one knows this more than Gabriel Snyder. As a writer in this pivotal time, he has been witness to the last decade plus of digital media evolution at major publishers like Gawker, Newsweek, the Observer, and the New Republic. Over rum old fashioneds provided by Fool’s Gold, he recalls that while each suffered from nuanced challenges, no publisher was spared and his insight to what he has seen and the lessons learned along the way are critical to understanding where the industry is headed.

Nisha Chittal

As both a journalist and digital strategist, with a background in social media marketing for large brands and a passion for politics, the stars seemed to align for Nisha Chittal during this past election cycle. Nisha helped lead major news organizations like NBC and MSNBC in their content production and distribution across emerging platforms and nontraditional channels like Facebook and SnapChat, which, of course, is not without many unique challenges. Over Aperol Spritzes at Fool’s Gold, Nisha describes how the newsroom organized itself in order to support these platforms, the shift in their approach after the widespread epidemic of “fake news,” and the importance of finding balance in a 24/7 news cycle world – including when it may be right to call it quits altogether.

What You’ll Learn:

– How are publishers using social to tell the story in a different way.

– The heightened responsibility of the journalism community to debunk and fact check their sources.

– The incredible challenge to remain objective in a polarizing news cycle.

Derek Parham

As the dust settles on a historical election season and people continue to comb through all of the factors that lead to its results – one thing remains top of mind: the role of digital. Derek Parham, who acted as Deputy CTO of the Hillary Clinton campaign, offers some behind-the-scenes insights into the most internet-centric campaign to date; his integral role within the digital team which operated much like a well-funded startup. Over bourbon at Fool’s Gold in New York City he recounts his trajectory leading to this very unique role – starting with software development with his dad in the basement of his family’s Bedford, MA home to helping create Google’s suite of apps, to his startup trials and errors. It’s an experience that exemplifies tenacity and one that certainly gets our vote.

What You’ll Learn:

– The value of learning all parts of the digital product process.

– Why sometimes leaving a job without another lined up can be the best way to find the next opportunity.

– The many unexpected pitfalls of tech-adoption within the political realm.

Dana Schwartz

As the world of journalism continues to evolve, so does the role of writers who exist within it. Enter Dana Schwartz. While her resume calls her an Arts and Entertainment writer for the Observer, that’s hardly encompassing of her “day job.” At 24, she has an impressive background; starting as a pre-med student at Brown before doing an about-face to pursue her passion in writing – and the many avenues it covers – including penning her first novel while interning at the Late Show, contributing to Mental Floss, and finding her balance with comedy and journalism as a “blue check mark” on Twitter. Over old fashioneds at Fool’s Gold in New York she describes her journey of falling head first into major media frenzies and taking the bold step of calling out her boss, and how it’s compelled her to continue to contribute and learn what her personal responsibility is along the way.

Charles Adler

Charles Adler embodies the true spirit of being a maker in the age of the internet – starting with the inception of an idea through prototyping, beta testing and ultimately launching and evolving as he goes. It’s a process he’s developed and perfected over the course of his career – with myriad roles including UX designer, visual designer, developer, founder, and more – in both on and offline companies. It’s this varied background and methodology that lead to his most popular endeavor yet as co-founder of crowdfunding site, Kickstarter, but over Bulleit Rye in WGN’s studio in Chicago, he explains how his background in the budding punk and EDM scenes and the self-starter culture that accompanied it not only lead to creating that platform, but has inspired him since. And that is still true today, as he approaches a new company – furthering facilitating the makers community in a more tangible way than ever before.  

Sara Chipps

Sara Chipps is, first and foremost, a developer. At a very young age, growing up in New Jersey she was intrigued with the internet and all the possibility it held. As a student, she pursued coding with a passion – overcoming the hurdles that come along with being a woman in a field traditionally dominated by men. Her current startup, Jewelbots, which makes smart friendship bracelets that are designed to inspire girls to get more involved in coding, is the culmination of her experience and this early passion. Over sancerre provided by ABC Wine Co., Sara and I discuss her experience as a temp working a helpdesk, as the CTO of Flatiron school and founder of nonprofit Girl Develop It, that helped her form a company career that teaches people of all ages that not only does coding not have to be intimidating, but that it can be fun as well.

What You’ll Learn

– How everyone can learn to code if they just give it a try

– How getting involved in coding at a young age can open up opportunities

– The key differences between being a CTO and a CEO

Soren Bowie

One of the themes of Story in a Bottle is that there’s no one path to a career in ___. Soren Bowie, a writer and editor at Cracked, is certainly the embodiment of that. While Soren was always interested in entertainment, his path to comedy writing was a winding one. From starting out as a child actor and star of some straight to DVD films, to getting paid to watch movies for a living as a DVD quality tester, to a few unintentionally unpaid writing assignments, to finally working his way into Cracked by making funny videos for eHow, Soren kept taking risks and following his interests. In a wide-ranging conversation over Moscow Mules, we talk about his path from rural Colorado to LA, the role of humor in explaining geopolitical drama, the trajectory of a joke on Twitter, why arguing with someone with opposing political views is never going to change their mind and, finally, why all the moms on 80s sitcoms were dead.

Eve Peyser

Gizmodo Night Editor Eve Peyser always knew she wanted to be a writer. However, it was a chance encounter at a bar with a college friend paired with her talent for comedy that has landed her firmly at the intersection of journalism & comedy, especially as a powerful (and hilarious) voice on Twitter. Starting out as a sex and dating reporter, she would often mine her personal life for editorial content. As she has evolved personally, she’s pulled back on the self-professed over sharing and is using humor to delve into more serious topics such as mental illness, the current political climate, and the pitfalls of capitalism.

What You’ll Learn:

– A good scoop can come from anywhere – even Tinder!

– Why the responsibility of the media is more important than ever – even for those in non traditional, journalistic roles.

– The pros and cons of the over sharing culture on the internet.

Robert Simonson

Author Robert Simonson always knew he wanted to be a writer, but even in his early career, never imagined where he ultimately ended up. Starting out as a theatre reporter in New York, but he grew tired of the beat and made a bold move into the world wine of wine to find more of a community. However, it was this change in trajectory, which corresponded with the cocktail revival in the US around 2006, that opened the door to his latest and lasting pursuit: the art and history of the cocktail. As one of the first reporters to cover this reviving scene, Robert saw an opportunity and became an expert, furthering his career as he authored The Old-Fashioned and A Proper Drink. Over Boulevardiers (Negronis with Rye instead of Gin) at Fools Gold Bar, Robert talks about the origins of the cocktail revival, how he educated himself when he wanted to change reporting beats, and how big liquor companies influence what we drink.

What you’ll learn:

– How and when to educate yourself to take advantage of an opportunity

– How knowing what you want to do early on can lead to a great career

– About the past, present, and future of the cocktail revival

Susan McPherson

“We’re living in an era where companies can stand for something,” says Susan McPherson, founder of McPherson Strategies, a consultancy that connects brands and social good. Starting out as a journalist at USA Today, Susan’s road to entrepreneurship has been filled with unexpected twists and turns. With her dad’s words of “nothing is a prison sentence” in her head, Susan took risks, from changing the direction of her career from journalism to marketing to relocating from Washington DC to California and then Seattle. Over un-oaked South African white wine, she discusses how these risks set into motion the path to becoming an entrepreneur that she still follows today, as she opened up new markets and introduced new products at PR Newswire to the work she does today helping corporations create messaging and strategy through the lens of social good.
What You’ll Learn:

– How corporate social good programs can attract and retain the best customers and employees.

– How working as an “intrapreneur” in established companies can prepare you for entrepreneurship.

– How knowing your strengths and hiring great people to supplement your weaknesses can lead to success as an entrepreneur.

Merrill Brown

Merrill Brown has worn many hats over the course of his career in journalism; beginning at the Washington Post to founding editor-in-chief of MSNBC.com, he’s seen first hand the evolution of the industry. From printing to mass distribution and the improvement of tools to help information spread faster, it’s never been an industry that benefit from resting on its laurels. Over beers at ABC Beer Co. in New York City, Merrill talks about how he’s kept this innate truth as motivation – and maintained a focus that’s one step ahead. This has served him especially well, as technology has made an ever-expanding world that much smaller and content production that much easier. Today, he’s poised to coach a new class of journalists to do the same, as the Director of the School of Communication and Media at Montclair State University where he helps to shape the future of the industry.

What You’ll Learn:

– How and why a journalist’s responsibilities have increased over time

– Why the industry may not be prepared for the short and long term of this political season

– The danger in ignoring or rejecting trends in technology

Rebecca Soffer

One of the unfortunate, universal truths of humanity is that, at one point or another, everyone deals with the loss of a loved one. Be it a family member, close friend, spouse or partner, grief can manifest in many forms and stages, and so while it’s not novel in concept, it affects everyone completely differently. For Rebecca Soffer, the loss of both of her parents inspired her to seek company in others who have experienced the same, and was the catalyst that lead her to her co-founder, and ultimately their site Modern Loss. Over Shirley Temples, Rebecca talks about her path leading to that point – being the product of two parents who fostered her love of words, her unique background in Hispanic marketing (including several stints abroad), and how she eventually realized her dormant dream of going to Columbia Journalism School. And just when it seemed her resume was a bit winding, it was this distinct experience of loss that tied it all together to give her perspective. Modern Loss is as its name suggests: a community that embraces mourning and the unique circumstances created from it within the modern world, especially compared to the historical solution of trite, “this too shall pass” advice. Rebecca explains that, while all content on the site is singularly linked with the throughline of mortality, that it’s truly about the lives of the people who carry on, and how they have been impacted by their loss – happy, sad, confused or otherwise. And, while Modern Loss has been the solution to the problem she had personally needed to solve, becoming a founder has, of course, lead to more challenges as she grows and expands the site to help create that haven for others.

What You’ll Learn:

– How to create a content site where you may be part of the audience, but not the only audience.

– The value of taking comfort where it provides itself – even if it is not your perspective.

– Why being a successful founder takes a healthy combination of “balls and ignorance” (at least, according to her dad).

Tony Mugavero

A natural entrepreneur is someone who, despite his best effort, can only excel in business when he works for himself. However, when he can also focus that drive with the clear vision to see opportunity where others do not, he’s passed litmus test as a true innovator. Tony Mugavero is just that. As co-founder and CEO of Virtual Reality platform Littlstar, Tony and his team come up with innovative ways to bring virtual reality to the masses; from 360-degree, journalistic videos to immersive, branded content, across myriad devices, they are leading the charge in this seemingly nascent industry. Over Victoria Prima Pilsners provided by ABC Beer Co., Tony talks about not only his path leading to this industry – by way of small businesses since he was a kid growing up in Dallas to his experience creating a music streaming service in the mid-2000s – but also the growth of virtual reality since its inception. Though it’s one of the hottest, up-and-coming trends in the tech world today, which is just now getting to some of the peak experiences at consumer level, he reminds us that VR has been around for decades and gives insight about how we can expect the best experiences ahead of us.

What You’ll Learn:

– How to not only make it, but pioneer an industry where you have little to no experience

– Behind the scenes in virtual reality content distribution

– The challenges in trying to work with Lucas Films and Star Wars

Jenna Matecki

One of the most valuable characteristics an entrepreneur can possess is having a well-rounded background of roles and perspectives over the course of his or her career – establishing a baseline of context and experiences to better serve in business pursuits. It’s a quality that is not lost on Jenna Matecki, founder of Matecki & Co. When considering her path, on the surface, it seems obvious that she is driven by the pursuit of her passions, sharing equal time between politics and art while layering in tech and startup experiences, as well. Over negronis, we learned what’s truly at the heart of her drive: her natural tendency to uncover the most interesting aspects that define the story, and, while the subject matter may change, it’s this role as a modern historian which remains constant. That is especially apparent today, as founder of Matecki & Co., where she sits poised at the intersection of brand, PR, and marketing – helping companies large and small define the elements of their DNA and, ultimately, their story. And as a personal project – leads her to uncovering the stories of others, which she showcases on her podcast ‘Notes On Doing’ (which may or may not have a familiar guest this week).

What You’ll Learn:

– As a company – the value of expressing what is special and unique about what you do.

– How to put an interesting lens on what otherwise might be considered banal.

– Why straying from societal norms can be important to your or your company’s success.

Will Mayo

As technology continues to evolve and consumer habits shift so do trends in content creation in order to reach people in myriad ways. And while there is no end in sight, Will Mayo, founder of Spoken Layer is doubling down on sound. Growing up with dyslexia and overcoming the challenges that came along with it as a student, Will has not only appreciated this medium, but thrived because of it – benefitting from having his textbooks audio-translated. Moreover, in having a musical inclination and passion for choral singing, this interest was only further substantiated. Over ginger beers he explains how the culmination of these things plus his academic career in engineering lead to the first iteration of Spoken Layer – with a goal of being a music collaboration tool. However, like any great founder, he was able to listen to the needs of his audience and, while learning how to operate at various life stages of his company, he was also able to pivot (twice) in order to finally realize the true problem audio was able to solve. Today, as the company has grown to fit into the more compartmentalized consumption habits of the population – as an audio-transcription of some of the most popular content on the internet – Will too is figuring out how this fits into his day-to-day as a founder and thought leader in the space.

What You’ll Learn:

– How to transform a space to adhere to meditation, work, and life

– The benefit of test and learn approaches to product development

– The importance of managing your expectation of employees based on your company’s life stage

Gillian Morris

Gillian Morris, founder of travel app Hitlist, has a story that is unsurprisingly filled with travel; from family trips to Canada as a kid, a stint living in a bell tower in Paris, and journalist gig in Turkey, she’s certainly appreciated many points of view across the globe. That’s how she became the unordained travel agent of her immediate friends and family, and despite her initial tech ineptitudes, was uniquely poised to bring these types of opportunities to the market. Over ginger beer and vodkas, we get a behind the scenes peek at the milestone moments that have lead her to where she is today; with a resume that includes a Harvard degree, international journalism experience with CNN, and even parakeet wholesaling (yes, that’s right). Gillian explains how the single driving motivator has always been to set her sights on a new place and see what happens and how she’s able to continue to achieve that today, even with a founder’s schedule keeping her mostly grounded.

What You’ll Learn:

– The myriad trials-and-errors of fundraising

– How it’s possible to turn your passion into a business

– The benefit of changing your perspective – and the impact it can have on your career

Brad Svrluga

A strong investment thesis can help VCs sift through the plethora of companies that come their way. With Primary Ventures, Brad Svrluga’s second venture firm, he’s focused on companies that are solving real problems with SAAS products for both businesses and the general public. Over Mezcal, Brad talks about his path to venture after shortly considering a career in chemistry, his quick shot up and even faster fall down in the venture world of the dot-com boom, and what it takes to get in front of him and his partner to pitch your startup.

What You’ll Learn:

– The challenges in building product and distinguishing between what the market thinks they want vs. what the market needs

– Why investing in a great idea and an authentic founder without a clear business plan is okay

– How the way startups approach funding is can be an example of how they run their companies

Caitlin Strandberg

Caitlin Strandberg has a resume that spans many industries and roles — from studying history in undergrad and a MBA from Harvard post-grad, to a stint in content creation and publishing in the music world, to hands-on founder apprenticeship at noteworthy startup, Behance — she’s appreciated many perspectives. However, over Arnold Salazars (an homage to her hometown in Florida that she shares with pro golfer Arnold Palmer) she explains that her drive is that of the eternal student – that once she overcomes a steep learning curve of one industry, she’s searching onward to the next. That path has served her well, and especially today, as a “student” of Venture at Firstmark Capital, where she brings her unique background to the table while she embarks on the path to becoming the next best investor.

What You’ll Learn:

– The value of having a great mentor

– How sometimes making a career out of your passion may not be the best move

– The benefit of being a “student” in your career – and how to approach new opportunities

Charlie O’Donnell

In the high risk world of venture capital, investors need to not only be savvy, but also innovative. Charlie O’Donnell stands out in the crowd as one such VC whose process is nothing less than unorthodox. The native New Yorker and sole partner of Brooklyn Bridge Ventures sets his own rules – taking meetings literally anywhere with anyone, resulting in one of the most diverse portfolios (including an incredibly diverse stable of founders) to-date. Over homemade milkshakes from one of his investments, Ample Hills Ice Cream, he talks about how this diversity is important for early stage investors specifically, but not without the challenges of growing into this position of power and the scrutiny that comes along with it.

What You’ll Learn:

– How to learn and grow from criticism and setbacks, especially when they are public

– How to find and deliver value in every meeting

– Why it’s important to know your expertise – and when to call on others who know more than you

Bianca Caampued

Bianca Caampued, one of two small girls who founded the aptly named Small Girls PR, began her career under the equally appropriate internet pseudonym BiancaRocksOut. In those early days, she rocked out in every aspect of her life, from running PR for Cure, a thrift store in New York City to seeking out the unique opportunities of the social and tech landscape that the city afforded. The circumstance was primed such that when she connected with her co-founder, whose birthday party she crashed, they found they shared a desire to create content and an entrepreneurial spirit that lead them to create Small Girls PR. Over glasses of Pedialyte (there’s an explanation, we promise), she shares how their interest in creating a web series lead to the founding of their PR company and how they’ve figured it all out along the way. Now, several years, incredible clients and projects in, the company has grown well beyond its initial expectation, boasting a staff of 40+ spanning both coasts (and more than small girls, at that), but is still rocking out… maybe in a slightly different way.

What You’ll Learn:

– Whether or not a formal business plan is necessary when starting a company

– The value of culture and a personal brand within your company

– The perspective of starting a company with social media at its core

Michael Cervieri

If there are two sides to every story, it seems that at the speed in which information travels these days, and the multitude of sources, perspectives are, more than ever, in great conflict. Enter Michael Cervieri. Michael has always known he was meant to be a Writer (with a capital “W”), and, while he spent his early days pursuing the life of a great novelist, he has consistently chosen to entrench himself in perspective and presented his work accordingly. However, when his travels in Central America lead him to deviate from fiction down a path of adventure journalism he was able to see most clearly where that perspective was most desperately needed. Over negronis, Michael talks about how this awareness lead him back to journalism school on the heels of 9/11 and a stint in the Middle East thereafter, and how it’s all culminated at his current project – the Future Journalism Project. His mission has never been more clear; the news cycle demands a rewrite and while the interconnectedness of social has given us the ability to share information at a rapid pace, not all news warrants that protocol.

 What You’ll Learn:

– How every company is a media company.
– Why discerning the importance of news events is an ongoing challenge for the public – “When everything has this heightened importance, nothing really has heightened importance.”
– The difference between the practice and academics of journalism.

Renee DiResta

Renee DiResta’s career has been far from conventional; from a government gig to programmer-turned-trader on Wall Street to a stint as a VC in Silicon Valley, she’s certainly appreciated many points of view. Today, as the Founder and Director of Marketing of Haven, a shipping container marketplace catering to myriad clientele, that varied experience has proven to be helpful as she navigates the complicated world of a startup – especially one trying to innovate and bring a centuries old industry into the world of digital. Over virgin mimosas (orange juice and seltzer) she explains how she’s had to evolve her working style from industry to industry, the importance of empathy when building both products and teams, the logistics of logistics and the many challenges of revolutionizing one of the the world’s first industries.

What You’ll Learn:

– As a startup, how to avoid building something nobody wants (hint: it starts with company leadership)

– Why a product should aim to “enable” rather than “disrupt”

– How to succeed in an industry even if you’re not a subject matter expert

Tomer Sharon

In the world of User Experience, the argument of formal education vs. on the job training is bigger than ever. One could argue that Tomer Sharon began his education in User Experience long before the field even existed. As a young man serving seven years in the Israeli Defense Forces, and as a project manager at a defense contractor after, he was immersed in training in problem solving and complex systems and the use of technology in critical circumstances. However, what his service left him longing for was bringing creativity into his day to day vernacular, which finding, was less clear. After several attempts at school and work – from copywriting to advertising gigs – he eventually found a path officially into User Experience; a world he understood long before he arrived. Since then, he’s spent the better part of his professional life at Google where he helped inform many products, most recently gathering insights impacting search results – a system that, while simple to the user, is solely so because of the careful consideration of the team. Today, as Head of UX at WeWork, he has taken his immense knowledge of complex systems and user research to bridge the customer experience both on and offline. Over Sam Adams he tells us about his approach to resolving the issues of this growing company and why, while largely unavailable to him, formal education is at the top of his checklist for potential User Experience candidates.

What You’ll Learn:

– The importance of a discerning mind in user research – why all insights shouldn’t be taken at face value.

– How becoming your audience may be the key to understanding your product.

– Behind the scenes of Google’s hiring process and why it takes so long.

Drew Grant

Drew Grant has spent the better part of her professional career at the forefront pop culture; from her early days as an editorial assistant at 236.com to establishing one of Observer’s most successful verticals, it’s a niche subject matter where her personal interest and voice thrive. Over hard root beers provided by ABC Wine Company, she recalls some of the more exciting moments of her career: from her early childhood inspiration that got her interested in entertainment news (spoiler: it has to do with Jurassic Park) and how it ultimately paid off, meeting President Obama (twice!), and the unique opportunities and editorial liberties she’s been given, including most recently becoming the Arts and Entertainment Editor of the New York Observer. She attributes her success to staying true to her passion & voice and never taking herself too seriously – we attribute it to her natural talent.

What You’ll Learn:

– Why childhood influences shouldn’t be ignored

– The value of having a scripted response (and perhaps more than one) in potentially overwhelming situations

– The importance of finding ways to evolve while staying true to yourself – for both businesses and individuals

Firat Parlak

Firat Parlak is a true problem solver, but his path to becoming a professional User Experience Designer came about through a series of unconventional steps. As a 14-year-old, he immigrated to the United States from Turkey, landing in New York City with equal parts ignorance and motivation. Determined to make a life for himself, he spent all of his energy focusing on high school, after school language classes, and working as a Flash developer through the contacts he made scouring Craigslist. What culminated was a refined sense of problem-solving, both personally and professionally, and an unprecedented self- and circumstantial- awareness with which to approach those problems. Today, as the founder of Awesome, a mobile design agency, he is now applying these life lessons not just to the work he does with his team, but also by educating others. His most ambitious education project is a program aimed to bring the vocational studies of User Experience to the incarcerated, a challenge given that the audience has no access to modern technology and internet. Over sauvignon blanc provided by ABC Wine Co., he explains that while his journey has been winding, he maintains that with passion “not everyone is made for UX, but anyone, not matter who you are, could be made for UX” as long as empathy remains the core of what you do.

What You’ll Learn:

– Why emotional intelligence can be just as important as formal training and education.

– Key advice for getting started in UX and the first decisions you should make.

– The benefits of teaching prisoners how to think like a user experience designer.

Elizabeth Osder

If anyone has been at the forefront of innovation in media and technology for as long as the World Wide Web has existed, Elizabeth Osder can certainly claim that title. Growing up in Englewood, New Jersey, one of her earliest memories was spending time in the local print shop with her mom – a graphic designer – basking in the scent of the ink and sitting in awe of the prints she’d made; it was those experiences that inspired her to become a journalist. However, as she delved into her studies and career, particularly in photojournalism, she ultimately had the realization that the infatuation was not actually with the printed materials she made, but rather telling the story mattered to her most. Over diet ginger beers, Elizabeth talks about how it was this mantra that has kept her at the forefront of technology; from helping launch the first version of the New York Times online, shaping the digital focus of NYU and Columbia University’s journalism programs, and today as she helps reinvent video strategy and experience for local news companies. While her path has certainly been winding and the industry is ever changing, her charge remains: never lose sight of the bigger picture – the story.

What You’ll Learn:

– The most important key to creating the best work is to put together a team of professionals that can solve the problem.

– Why tenure is a killer of innovation.

– The danger in people caring more about where they are doing something rather than what they are doing.

Cody Brown

It’s been said that “if you do what you love, you never work a day in your life” and Cody Brown is the true embodiment of that. Not to discredit the hard work he’s done, but in always allowing his passions to drive his pursuits, he’s been able to spend his academic and professional career pushing the boundaries of industry and technology in impressive ways. As a kid, Cody spent his days practicing his Academy Award speech, spending his days honing his filmmaking skills. However, when approaching his studies at NYU, he furthered this love of creation and self-publishing when he founded his first product, NYU Local, much to the chagrin of the archaic news sources of the University which preceded it (and got him mistaken infamy for plagiarism in Gawker). Over Don Draper style old fashioneds, he chronicled how all of this has foundationally kept him at the edge of tech, these days manifesting as the founder of VR IRL, one of the preeminent virtual reality production companies. His story boasts an exciting past, creating and selling innovative products to the likes of WordPress, but most importantly it looks to the future. He describes the moment when he realized that cyberspace is now real, the difficulty in the charge to bring that experience to the masses, but the amazing opportunity in connecting people through virtual reality that continues to motivate him to do so. Oh, and his beef with the term “VR.”

What You’ll Learn:

– How sometimes the nonobvious intersection of your passions can be the best place to innovate.

– The opportunities and challenges of building in a nascent industry like VR.

– Why “VR” may be a temporary title.

Prita Kumar

Prita Kumar boasts an impressive resume where her academic accolades are only surpassed by her practical experience. As a NYU Stern graduate, her trajectory seemed clear as she embarked on a life in the world of finance. However, an incessant need to problem solve paired with an MBA from Harvard Business School drove her to create a product she truly believed in. Over glasses of Chardonnay provided by Alphabet CIty Wine Company (abcwinecompany.com), she discusses how her concept for Booya Fitness – a streaming group exercise class experience – immediately caught on, winning grant money and sponsor backing, gaining an audience, and potential investors. Booya’s a momentum was fueled by Prita’s hard work facilitating all parts of the business, a drive that kept Booya moving forward in an uphill battle against the saturated intersection of content and fitness. Unfortunately it was a battle that Prita ultimately realized was going to prevent her from ever reaching critical mass. This Story in a Bottle shows the excitement of potential success, but illustrates the true challenges of how to stay afloat and even pivot when you desperately believe in your idea and just need that “one more thing” to keep you going – and how to pick yourself up when that one thing arrives too late.

What You’ll Learn:

– How wearing multiple hats as a founder can ultimately inhibit the business

– The challenges of running a business for three and a half years on a shoestring budget

– Navigating the the myriad advice you receive as a founder – because everyone has some and not all of it is right for you

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.