52 Founders

In this episode, you’ll hear about: -The state of innovation in Chicago, and how the startup ecosystem has changed since Sean built his first company -Sean’s transient childhood, and the hardships he saw his parents endure as Taiwanese immigrants who tried to be restauranteurs -Why hard work is not enough to be successful, and why it’s important to spend time thinking about business dynamics in any industry -How Sean views mentorship, and the relationship that guided him to a career in product -Why Sean hates the celebration of entrepreneurs who put work above all else, and how that can lead to a lack of diversity in your company -Why important decisions should never be made in Slack Be sure to check out the last few minutes of the episode, where Sean shares some of his favorite Chicago startups and the founder he would most want to interview (it’s a new one, and a bit of a surprise!).

In this episode, you’ll hear about: -Why constant work chatter is actually detrimental to progress, and how to avoid the FOMO that comes from not immediately responding to messages -How Basecamp’s maintained steady growth over the past 13 years, and why rapid growth is not necessarily synonymous with success -Ideas for creating connections amongst remote workers, and the benefits that come with having a diverse set of employees -The words of wisdom Jason took from his father, and the ones he chose to ignore -How having both a wonderful and a terrible manager shaped the boss that Jason wanted to be -Why being risk averse and ignoring your competition can actually make you a better entrepreneur Check out the ending, where Jason shares a Chicago company he loves and why he really wants to talk to Judge Judy.

In this episode, you’ll hear about: -Who the ideal Fossa customer is, and why enterprise companies are not the only ones who care about code quality and security -The evolution from TLDRLegal to Fossa, and the opportunity Kevin saw to create a sustainable business -How attending the Illinois Mathematics and Science Academy boarding school shaped Kevin’s childhood and led to his early independence -How Kevin’s parents, who emigrated from China, were the driving force behind his technical education -The “dual life” Kevin led growing up between school and freelance coding, and how the latter became his motivation to start a company -How working at Techstars Chicago marked the beginning of Kevin’s startup journey, and why he decided to move to San Francisco Be sure to stay tuned at the end of the episode, where Kevin shares some favorite Bay area companies and explains why there isn’t just one person he would most want to interview.

In this episode, you’ll hear about: -How Bitnami evolved from a side project in 2008 to become a full fledged company in 2013 when the founders saw an opportunity surrounding the deployment experience -The pros and cons to raising outside funding, and why the Bitnami team choose to wait until the point where not raising would impede the business -Growing up in the Bay area, and how having an entrepreneurial father inspired Erica’s own ventures from a young age -How Erica views the idea of “being your own boss” and the misconception people may have about how it actually works -Her experience working at T-Mobile that taught her how to hire and manage large teams, and how to constantly be a better manager -How a founder’s job adapts with the evolution of the company, and why learning as you grow is critical to success Catch the fun question round at the end, where Erica shares a few favorite San Francisco startups (hint: one’s a 52 Founders alumn), and the founder she would most want to interview and why (it ma

In this episode, you’ll hear about: -Critical advice on how to bring new products to market, and how to find your ideal customer -Why business is fundamentally creative versus competitive -The strategy and decision making process as to why Sir Kensington’s is headquartered in New York City -How Scott’s childhood growing up in the Bay area influenced his idea of entrepreneurship -How living in Japan shaped Scott’s thinking on Sir Kensington’s flavor profiles, brand marketing, packaging, and manufacturing (kaizen!) -Who “Sir Kensington” is, and how the company went about creating this eccentric character to represent the brand Be sure to catch the end of the episode, where Scott shares which Sir Kensington’s product is his favorite, in addition to the NYC startup he loves and who he most would want to interview.

In this episode, you’ll hear about: -100 State, the largest coworking space in Wisconsin, and how it aims to be the center of gravity for the budding Madison entrepreneurial scene -How creating seven healthcare startups made the founders realize the need for Redox, and how the team solved the classic “chicken-and-egg” platform problem -Why his parents’ jobs instilled a deep ethical compass for Luke, and why you have to do what’s right even when it’s hard -Luke’s experience bringing iSAC , an international student exchange group that contracts with local city businesses, to Cornell -Why semi-informed advice is always the worst kind, and how to best take action from the cacophony of available data that exists -Why finding smart people is not the only metric you should considering when hiring, and why it’s imperative to think of what each hire will do when you are starting to scale At the end of the show, Luke shares one of his favorite Midwest startups (hint: it’s mine as well), his interest in the genetics /

In this episode, you’ll hear about: -The beginnings of Ionic, which originated from Codiqa, a drag-and-drop tool for jQuery mobile that stemmed from the desire (and frustration) to quickly build great apps -Why the pair feels so strongly about building Ionic from Madison, and the cabin (aka garage) phase of the company -The private messaging forum / blog they created among their friends in high school (before the days of Facebook) to share poetry, stories, and updates (and gossip) -The thought process Max and Ben individually had surrounding becoming an entrepreneur, and how Y Combinator’s resources inspired them to start -What it’s like to hire and work with your friends, and the advice Max and Ben have for those that go down that path -Why it’s critical to find your evangelists when you build products, and how you come to terms with killing features and designs you love that others may not -How Max and Ben bootstrapped Ionic to get it off the ground, and advice for entrepreneurs on how to smartly start a co

In this episode, you’ll hear about: -Why Boxed surprisingly has very little customer overlap with the traditional brick-and-mortar discount clubs -Why seasoned entrepreneurs go after different markets than first-timers, and how to look beyond just solving a problem -The culture behind Boxed that has made it such a publicly lauded company (see here and here), and why these values actually do positively affect your bottom line -How Chieh’s parents, who emigrated from Taiwan, managed to leapfrog the generation lag that comes with the proverbial American dream by placing a large emphasis on education -How growing up economically constrained has permeated Chieh’s business thought process -Why Chieh decided to quit being a lawyer to become an entrepreneur, and why the timing of his first job made the biggest impact of all Be sure to check out the end of the episode, where Chieh talks about the other New York companies he admires (hint: one’s a 52 Founders alumn!) and the current (and future) state of e-commerce.

In this episode, you’ll hear about: -How the idea for Pressbox started from Vijen’s aim to simply make life easier, and the other ideas he entertained before settling on dry cleaning -Vijen’s experience in high school reselling Cubs tickets at a lofty margin, and how that sparked his urge to be an entrepreneur -Why math was the center of Vijen’s life, and how this logical framework showed him how to create change (including how to lose weight) -How attending Notre Dame shaped Vijen’s perspective and future career by providing Vijen with future mentors for Pressbox -Why Vijen believes passion inspires others to help you, and why it’s critical to find something that you truly believe in Bootstrapping versus raising venture capital, and how the former makes you a much smarter money manager Stay tuned until the end of the episode, where Vijen shares a Chicago startup he really loves (looking at you Mark Lawrence) and we talk about the incremental improvements that can be made in healthcare.

In this episode, you’ll hear about: -Tradesy’s beginnings, and the little hacks Tracy did to build up both sides of the marketplace -Tracy’s transition from artist to entrepreneur and how she dealt with all of the responsibility that came with it -Why it’s important to pick activities that force you to learn-as-you-do them, and how Tracy took that to heart while living in Mexico -What it’s like being a female entrepreneur running a female-centric business pitching to mainly male venture capitalists -How Tracy originally bootstrapped Tradesy by renting out her room on Airbnb to cover initial costs (and how she ended up marrying her first guest!) -How earlier hardships taught Tracy to never quit, even during the hardest of times, and why resilience is the key to success Check out the end of the episode, where Tracy recommends her favorite books for entrepreneurs to read, the fields of tech she sees taking off, and, of course, the founder she most would want to interview and why.

In this episode, you’ll hear about: -Why Danielle and Michael decided to focus solely on younger founders, regardless of whether or not they attended university -How starting a venture fund increased her empathy for entrepreneurs, particularly through fundraising efforts -Danielle’s experience starting a charter school in San Diego, and why it was easy to fall prey to “imposter syndrome” during that time -Her experience as an instrumentalist growing up and how that helped her learn to lead, direct, and give feedback to her peers -Why previous execution is critical for applicants to the Thiel Foundation and for entrepreneurs looking for investments from 1517 Fund -The correlation between alternative schooling and entrepreneurship Stay tuned to the end of the episode, where Danielle shares why founders should read personal development books and her current interest in sensor-based technology.

In this episode, you’ll hear about: -How Popular Pays evolved its product since its inception based on the feedback it got from its initial customers -Why building a company on a mission is more important (and challenging) to Corbett that figuring out ways to simply make a profit -His father’s own work on a startup, and how that helped Corbett learn more about term sheets, making connections, and raising initial funding -How failure can teach you a lot about your appetite for risk, and how Corbett’s experience in advertising helped him build a thick skin -The “graveyard” of ideas Corbett’s cofounder built while at Leo Burnett, and how it served as future inspiration for new ideas -Why having a cofounder is a good way to hold yourself accountable and why picking the right one is the most important thing you’ll ever do Check out the final few minutes of the show, where Corbett shares a few book recommendations and why he’d want to interview more recent startup founders than the traditional tech giants.

In this episode, you’ll hear about: -How one customer with over 5,000 employees saved $48M in savings in a year from offloading these everyday tasks to Zoom -Why Toronto is the ideal location for creating a machine learning / AI company, and how it’s become the 3rd largest technology hub in North America -How being an only child raised by a single parent made Roy think creatively about how to make extra money from a young age -How Star Wars and his first software sale made Roy realize he was meant to be an engineer, and why joining someone else’s startup first made him a better entrepreneur -Why building a business is like being in a dark room with lots of furniture, and how befriending experienced founders will keep you from getting hurt -Roy’s experience as a solo founder, and why he doesn’t recommend being one to other people Roy’s also an investor an advisor to other startups, so be sure to catch the end of the episode where he shares the advice he gives to first time founders and the best books to read

In this episode you’ll hear about: -The struggles of content marketers today, and why media startups need to be especially scrappy and resourceful to succeed -The present opening Rachel sees in media companies and who the Love Stories TV’s typical user is (it may surprise you) -Rachel’s childhood growing up in suburban Detroit, where she was a competitive, synchronized skater! -How coming from a family of entrepreneurs helped inspire Rachel to eventually become one herself -The grand vision beyond weddings that Rachel sees for Love Stories TV, and why content is king when it comes to videos -Why entrepreneurs should be wary of using the “we’re the [blank] for [blank]” description when first building their companies Stay tuned until the end of the episode, where Rachel shares the best piece of advice she’s gotten thus far and explains why she’d want to interview The Knot’s Carla Roney if given the chance.

In this episode you’ll hear about: -The origins of Kylie.ai, and why it’s entrepreneurs should always listen to prospective customers when developing new products  -How his mother’s blend of math and psychology, and his father’s 30+ year tenure working at GE, inspired him to be an entrepreneur -Sinan’s experience as a professor at Johns Hopkins’ (after finishing his Bachelor’s degree in just 2 years), where he met his then-chocolatier (yes, chocolatier!) cofounder  -How Sinan fell in love with data science after teaching himself how to code as it’s the perfect blend of computer science and math -Why it’s critical to continually show people what you are building Sinan’s response to critics of AI, and why the winners of AI will be ones that can integrate successfully into what humans are already doing Be sure to stay tuned to the end of the episode, where Sinan explains his love for Henry Ford and why he’d want to talk about the way Ford integrated technology with the masses to ensure widespread adoption.

In this episode you’ll hear about: -When Taylor first saw the opportunity for Tiz, and why he decided to work at -Drizly before striking out on his own -The benefits of launching a startup in Chicago over San Francisco, and why top universities are critical to the ecosystem -How Taylor broke the family occupational mold by being an entrepreneur (he comes from a long line of surgeons!) -Why working in sales at a tech startup provided the best foundation for eventually running a company -Why attending college was always the choice to make, and why Taylor would encourage others to do the same Catch the end of the episode, where Taylor goes over the best (and worst) advice he’s ever heard as an entrepreneur, and why you shouldn’t hold a grudge when things don’t work out.

In this episode you’ll hear about: -Why innovation tends to happen at the cross-section of disciplines, and how Sparrho is helping foster that innovation -Vivian’s childhood growing up in Australia (with parents working in education and publishing) where she discovered a love for science -The “contained chaos” that happens when getting a PhD at Cambridge, and the opportunities for leadership that were there -Why the occupational and cultural diversity in London will continue to drive problem solving and lead to the creation of more startups -The state of entrepreneurship and venture in Australia -How learning to program gave Vivian an appreciation for logic that went beyond her education in science Be sure to check out the end of the episode, where Vivian succinctly sums up the best piece of advice she’s ever received, the question she’d want to ask Elon Musk, and why she’d want to interview small-scale entrepreneurs.

In this episode, you’ll hear about: -The genesis of Aire, the vision Aneesh sees for the next 20+ years, and how to show value to investors along the way -His own transient childhood as the son of the diplomat (and a journalist), and how the “start, restart” mindset led way to entrepreneurship -Aneesh’s early activism, starting with an angry letter he wrote to Panasonic as a 16 year old to fix his MD player, and why he has always refused to accept “no” as an answer  -What leadership truly means in an organization, and how his opinion has evolved over time -The value of building a startup in London, especially if you know the fintech ecosystem -Why having the right foundations means everything when starting a company, and why complexity at the beginning will only create more worries later on At the end of the episode, be sure to catch Aneesh’s recommendations on top books to read as a founder and his response to the founder he would most like to interview (hint: it’s a new one!).

In this episode, you’ll hear about: -Why it was important for Cleo to have a personality, and the opportunity Aleksandra sees in the space -Growing up in Poland and how her father helped foster her early interest with -technology  -How, as a child, computer science felt like wizardry, where scripts were spells and programs were magic -Why Aleksandra was not deterred by not having prior leadership experience (and why learning by doing is critical to success) -Why London is the perfect locale for launching a new venture -The importance of having balanced personalities between cofounders Check out the end of the episode, where Aleksandra talks about the future of VR and why it’s critical to not be afraid of who you are (and who you want to be).

In this episode, you’ll hear about: -How the idea for Occasion was born out of frustration from being unable to reserve tennis court time in Chicago -Aksh’s view on how AI will transform his industry -The long lineage of entrepreneurship in Aksh’s family, and how it molded his childhood dreams -Why Aksh works at his mother’s store every six weeks, and how that enables him to build a better product -The apprenticeship program Occasion started for its employees in order to gain more customer empathy -Why entrepreneurs shouldn’t equate business failure with personal failure Catch the end of the episode, where Aksh talks about the growing importance of voice interfaces and why it’s critical to surround yourself with mentors who are much more senior in their career.