When creating a product, often times the best approach is to start small with core group of users and use cases and grow. Michael Pryor successfully bucked that trend when he co-founded Trello, basing his company on the idea of “bringing structure to any process,” regardless of the aim of the project or industry using it.  Since its launch at TechCrunch Disrupt 4 years ago, it has gained 10+ million registered users who are utilizing it for projects that span from wedding planning, to HR onboarding for small companies, to Sales CRM and beyond. Their reach is only growing thanks to the evangelization of the product by many core users. Trello wasn’t Michael’s first attempt at digital products. Growing up in Lancaster, PA, he had early interest in computer science. Over a few cans of Mama’s Little Yella Pils (generously provided by Alphabet City Beer Co.), he remembered his ‘tech’ origins (which involved meticulously inputting Basic code from coding magazines, into his Texas Instruments computer), his time at Dartmouth building websites for professors, and his subsequent years working for Juno and a development consultancy that weathered the pop of tech bubble by creating their own products (most notably Stack Overflow). Several decades, products, and teams later, he’s continuing to get to the root of user obstacles, creating the best tools to solve them. Needless to say, he’s on to something good.

Kellee Khalil grew up surrounded by entrepreneurs. Her father moved to America with a one-way ticket and an eye on the American dream. His business-minded attitude, paired with the creative influence of her florist mother, set a lifelong example of finding an opportunity and making it work. As a true California girl, she attended USC where her major was entrepreneurial studies. This gave her not only the foundation to become an eventual business owner, but helped solidify the business acumen she had grown up with: “identifying problems and building solutions around it.” As the Maid of Honor for her sister’s wedding, she found such a problem to solve as she was constantly turning to Google for answers to everyday, commonplace, wedding planning needs. The outdated and unhelpful businesses that comprised the $99 billion dollar wedding industry needed innovation and that’s just what she was going to bring to the table with her company, Loverly. Over Tito’s vodka sodas, provided by Alphabet City Wine Co., we discussed her take on outside capital (“Sometimes it’s better to sell the dream and get as much money as you can, then you have enough time how to figure out how to execute.”) and how ripe the wedding industry is for an innovative overhaul.

Growing up, every kid wants to be an astronaut. For Inder Singh it wasn’t just a dream: he “did everything in [his] power to get there.” He threw himself into the field starting with attending Space Academy as a kid, learning to fly a plane at 16, and finally working at major rocket labs while studying engineering at the University of Michigan (which he was compelled to attend because their symbol flies on the moon). This full-speed ambition, along with a with drive to constantly be learning from the best and the brightest is a theme throughout Inder’s life and has produced a dizzying number of accolades: the founding of a successful nonprofit, 3 master’s degrees between MIT and Harvard, and public praise from Bill Clinton for his work in bringing more affordable malaria treatments to the third world, just to name a few (though his mom still wanted him to follow in his family’s footsteps and become a doctor). His latest venture, Kinsa, looks to combine his extensive background to revolutionize how the spread of infectious diseases are tracked, starting with a simple device that every household has: a thermometer. In this episode, we sat with Inder to walk through his story and what he sees next on the global health tech horizon. While he may not be an astronaut or doctor, we think his mom is still pretty proud. This episode’s Wodka tonics were provided by our friends at Alphabet City Wine Company.

As a day trader at JP Morgan your life often resembles that of a startup founder: too much to do, constant pressure, and around the clock hours. What you may not see is a key difference in a lack of flexibility. Carolyn Lanzetta entered the finance world after graduating from Dartmouth. She was drawn to the banking field by the clearly defined roles and expectations. After the birth of her first child, though, she knew something, mainly her profession, had to change. Parents, especially mothers, were not abundant on the trading floor and the rigidity of the job allowed for zero flexibility. In the cut-throat world of big finance “you barely grab lunch from the delivery guy who brings it to the lobby, let alone an appointment at your kid’s school.” So she quit and left a world of clear cut rules and entered the completely foreign world of startups. Plum Print is the brainchild of Carolyn and her cousin. Together, they pooled their knowledge and sought to address a need of many parents: preserving their child’s artworks and momentos in a meaningful way, while also reducing the clutter. They started small, and as the company grew, so did their web footprint. Over John Daly’s we sat to discuss the parallels between finance and the tech world, how, with zero tech knowledge she has found both her footing and place as a startup founder, and the challenges, mistakes and lessons that she has encountered along the way.

Unlike many of our guests, you won’t find Sam Kassoumeh on Twitter. In fact, you won’t find his profile on any social media sites. He removed them all before Snowden’s leaks, based on an inkling. Growing up in ‘Ford Country’ he was surrounded by friends and family working in the automotive industry. It was assumed he would follow in their footsteps. At 14, he was drawn to a different path as he began ‘white hat’ hacking as he broke screenname rules on AOL 2.0. From these humble beginnings he began his career as a top internet security expert. After graduating from The University of Michigan and a few corporate jobs that followed, he worked his way up the ranks, eventually helping build a military level security system at Gilt. He realized at this point how much the sphere of the internet needed better security as a whole and launched his company Security Scorecard. Over a bottle of Cotes du Rhone, we discussed his take on internet security and why it’s not that “people should be fearful, but with that being said, people need to be educated.” In the age of celebrity cell phone hacks and Ashley Madison data leaks, it should come as no surprise that 70% of breaches are due to third party intrusion. This statistic becomes more and more relevant as we become increasingly reliant on the cloud. Our conversation was truly one of the most enlightening that we’ve had to date. With the knowledge that “a basic level breach costs a company $6 million and 2 years of remediation” it’s a conversation that could save companies both large and small.

Much like many who found themselves in tech, Christina Lewis Halpern began her career in journalism. Unlike most though, it’s her first foray into tech from that world that is making the biggest splash. From covering crime in Stamford, CT to grabbing quotes from Donald Trump on Wall Street, as well as the boom and bust of the real estate industry, she saw the true spectrum of wealth and humanity play out in the daily news. It left her wanting to help inspire change, much like her initial source of inspiration: her father. As the first African American to build a billion dollar company he sought (and succeeded) to bring diversity to some of the business world in the 1980s. It was his path that ultimately helped Christina find her calling with All Star Code. As she says, "Tech is the engine of job growth and wealth creation... and if we don't have people from diverse backgrounds in tech we face many problems." With All Star Code she is helping to bring some much needed diversity to the world of coding. Over Sancerre provided by ABC Wine Company, we sat with her to discuss the evolution of tech and how it not only can, but desperately needs, to be more diverse in order to avoid a new economic crisis.

What if the games you played as a kid shaped your eventual career? Dennis Crowley grew up in a family that made everything into a game with the simple goal of adding an element of fun to everyday life. After graduating from Syracuse University he moved to New York where he nurtured his passion for creating, with stints at early tech companies (Jupiter Research, Vindigo) until the first dot com bubble burst. At that time, when it seemed like the fun was over for many in the industry, he set out to find those still passionate about tech and a bit of direction, leading him to the esteemed ITP program at New York University. It was there that he developed his thesis Dodgeball, which would later be purchased by Google, immediately immersing him in the world of big tech and startups. Whether it was a product that was ahead of its time or just lost in a large company without a clear plan, Dennis eventually saw the writing on the wall and painfully walked away from Dodgeball with Google pulling the plug shortly thereafter. Dennis was still convinced that making the mundane fun could be a reality and the ideas behind his grad school thesis were worth another shot. Foursquare was born. As Foursquare evolved and the social media scene exploded, Dennis found himself at a crossroads. The original intention for the app was there, but user behavior was shifting and the company had to make major changes. Swarm, their most recent endeavor, is now in its second year. Over Keegan’s Mother’s Milk beer, we discuss the decision to pivot the Foursquare brand, the real reason behind it, and how following the path that’s been your guiding force since childhood can pay off in big ways.

Alexandra Klasinski doesn’t play by anybody’s rules. As a Silicon Valley native, she grew up surrounded by technology and thought processes about innovation, but even immersed in the heart of it all, unsurprisingly veered away from the tech path and towards her passions: art, photography and doing the unexpected.. From managing a fast food restaurant to working with high profile comedy writers and eventually with musicians (and a stint in a band herself), she’s let all of her experiences stay true to her idea that every job offers the opportunity to do something new. While conversing with us over boxed rosé spritzers (what she's coined "the douchebag"), she explained that as the music and arts spaces have evolved to be more digital centric, she has now found her way back into that space. Of course, on her own terms. When working with companies like Lomographic Society International and Edelman didn’t prove to suit her personal growth (the primary focus of all her pursuits) she didn’t let her deter her. Today, she sits very happily at the intersection of art and tech at 20x200 as the Director of Partnerships & Programming where she is able to bring art to the masses in a way that is both special and unique to the artists, especially herself. To see her (and other great artists') work in action, check out 20x200. And adventures @alexandrak.

Mark Mangan is the cofounder of Flavorpill Media, a company he started 15 years ago as last ditch attempt to save a failing startup. He took one element of the existing business: an added value email newsletter, which, at the time (and even now) seemed like an impractical way to sustain a business. But, from this (at the time) unique offering of a list curated local, cultural events (with a harsh editorial guideline to maintain authenticity) the company grew to become a leading culture and lifestyle brand. And with every success, they expanded, eventually creating large custom events of their own such as the renowned First Fridays at Guggenheim, as well as expanding to many markets & content types, including noteworthy blog, Flavorwire. As the head of  their innovation lab, Mark won’t let the company rest on its laurels, as he continues to push the envelop to new platforms as media consumption evolves. This position has not been without its challenges. Over 2 bottles of lambrusco, Mark shared his beginnings -- which actually start with him searching for the net (that’s right, it took a couple months for him to actually find it). Once he did he was scrappy in his approach, building websites which turned to companies, seeing the many successes and failures that can only be seen by someone who was pioneering virtually unchartered territory. The result was a personal realization: that as a founder, often times losing part of your team is more difficult than folding a company. The early insights also inspired his professional approach to begin early dialogue about freedom of speech on the web in a book he coauthored, which was noted by the New York Times as “required reading for anyone interested in free speech in modern society.” For more from him, don’t go to Twitter (because he doesn’t tweet), but keep an eye on the upcoming innovations from Flavorpill.  

As a digital designer, Timoni West’s portfolio started much like many others in the late 1990s: on Geocities. During those early days, when formal design education opportunities and mentorship eluded her, she applied self-motivation and a fearless approach to obstacles which ultimately allowed her to succeed beyond her imagination. With a career that boasts the likes of companies like Flickr and Foursquare, as well as navigating the sometimes frustrating world of freelance, her often unconventional methods have resulted in a career that is as strategic as it is creative. Over a bottle of Kim Crawford Sauvignon Blanc, we discussed her upcoming endeavor as the principle designer of Unity Labs. There, she will be pushing her collective experience in a new direction into the realms of virtual reality. We look forward to raising our glasses to what comes next! For more from her, follow @timoni.