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 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

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 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 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 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.

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 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.

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 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 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.