Chris Messina says he has lived 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

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.

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.

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 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

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

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

“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.”

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 her role as the Head of New Products at ABC News, where she’s doing her most innovative work yet.

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 Forbes, 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.

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.