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’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’s lifelong obsession with the internet began at its inception; in a time when there were no rules or standards, this self-taught developer was always focused on 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 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 Verheove 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 rose proviced 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 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.  

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 in relationships. 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.

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. 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.

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, 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, 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.

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 Cofounding 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.