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 may surprise you!).

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 / genomics space, and the future implications of sharing healthcare data.

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 company

-Defining moments in the company’s history thus far through the founders’ eyes

-Why being relentless and having passion are always the best way to know if you should work on an idea

Catch the end of the episode, where Max and Ben answer some fun questions, like companies they are evangelists for, other markets in which they would consider starting a business, and why they love Signal vs Noise, the Gospel of Basecamp.

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.