S2 | E4: The Psychology of Serial Entrepreneurship

In the final episode of season 3, Alice and Gena reflect on the five conversations they've shared. We hope you’ve found these conversations as valuable and thought-provoking as we have. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

In this episode Gena and Alice had the pleasure of speaking with David Booth, the founder and CEO of OnDeck—a curated community designed to increase your odds of building a successful venture-backed company. Now, if you're thinking that sounds a bit similar to Entrepreneur First's mission, you wouldn't be far wrong. Both organizations share a belief that the world is missing out on some of its best founders, and a passion for catalyzing globally important companies by reducing the barriers for the world's smartest and most ambitious people to go and found them.  In this conversation Alice, Gena and David talked about how David's parents raised him to be entrepreneurial from an early age, why founders need community before they need advice, the mistake of seeking external validation and credentialism as a way of outsourcing your own judgment of readiness, and much more.  Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

In this episode, Alice and Gena spoke with Blake Scholl, founder of Boom Supersonic. Described by The Guardian as 'the man who aims to bring the son of Concorde to the skies', Blake is on a mission to bring supersonic commercial passenger flights to the world as soon as 2026.  Why, you ask? Well, since Blake never got the chance to fly on the Concorde himself, and nobody appeared to be trying to revive supersonic air travel, he decided to do it himself. In his words, 'I realised that I wanted to work on the most important thing that's not impossible'.  In this conversation Gena, Alice and Blake discuss what moved Blake to take on this mission at a time when it would’ve seemed crazy to almost everyone, how he honestly answered the question 'am I the person to go do this?', how he’s had to grow and change to keep pace with his company, and much more.  Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

This episode is a little bit different and a particular delight for Gena, because she got to talk to one of her colleagues and direct inspirations: Amy Buechler—who is not a startup founder herself, but rather a psychotherapist turned executive coach. And not just any executive coach, but one of Silicon Valley’s most sought-after coaches, having served as Y Combinator’s first and only in-house Founder Couch for nearly 5 years before building her own independent coaching practice. In this episode, Alice, Gena and Amy talked about some of the distinct psychological patterns and pitfalls Amy has observed in the countless founders she’s worked with, from feeling empowered and disempowered all at once, to being pushed along by fear; and Amy shares some of her tools and frameworks for addressing those challenges.  They also talked about the very scrappy, entrepreneurial path Amy herself has taken in developing her founder coaching methodology, which really resonated with my own experience. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

In this episode, we spoke with Brett Kopf, a serial entrepreneur at the intersection of fintech and education. In 2011 Brett founded 'Remind', a tool designed to improve communication between teachers and parents. Remind has since grown to over 30 million active users, and is used by 80% of teachers in the United States. Remind has raised $60 million to date from the likes of Naval Ravikant and billionaire philanthropist John Doerr, and Brett remains on the company's board.  Brett's current company, Omella, is an all-in-one platform for payments, forms and signatures that Brett founded after seeing thousands of educators struggling with collecting money.  In this conversation, we talked about Brett's journey into therapy and how it helped him as a founder, the differences in approach between his first company and his second, how prioritizing his responsibilities as a father actually makes him a better founder, and much more.  Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

In this season we’re bringing you a veritable feast of bold and inspiring entrepreneurial guests, from the founder who’s building the world’s first commercial supersonic aircraft, to one of Silicon Valley’s most sought-after founder coaches. And this time no topic of conversation or exploration is off the table. En route to discovering the mindsets and strategies that have aided our guests on their journeys, we plumb the depths of their personal origin stories, battles with identity, and at times crippling mental health challenges. We hope you enjoy listening to this season of the Founder's Mindset as much as we’ve enjoyed creating it.  In this first episode, we spoke with Dan Murray-Surter, a multi-award winning serial entrepreneur, top podcast host and public speaker. Dan’s been described by The Sunday Times as a founder 'not afraid to rip up the plans', and by Entrepreneur magazine as 'one of the few brave voices speaking up about mental health and entrepreneurship'.  Dan's current business, Heights, manufactures a multi-vitamin aimed at improving brain function. In this wide-ranging conversation we talk about how Dan grew up watching his immigrant father struggle and concluded that business was a terrible thing, how he ended up starting one anyway, why he's building Heights in public, and much more. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

When you’re someone who’s as ambitious and driven as founders tend to be, it can be hard not to merge your personal identity with your company - despite all advice to the contrary. No-where has this been clearer than the conversations we’ve had this season of ‘The Founder’s Mindset’ .In this episode, Alice Bentinck and Gena Gorlin reflect on the insightful conversations we’ve had around entrepreneurship and personal identity. They share their learnings, including on how to deal with failure when it feels close to home; what motivates and inspires the most successful founders; how to reconcile differences in motivation between you and your co-founder; how to cope with stress; and how to build resilience. We hope you’ve found these conversations as valuable and thought-provoking as we have. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

In this episode Gena spoke with Ray and Rebecca Girn, two people who utterly defy all conventional wisdom about maintaining work-life balance. When it comes to both work and love, they are, as they often describe it, “all in”. Ray and Rebecca are part of the founding team of Higher Ground Education, which offers a radically different kind of education, centred around developing natural interests rather than formal teaching. Higher Ground owns and operates over 100 Montessori schools, one of which Gena’s daughter attends. This is a conversation about what it’s like to put all your eggs in one basket. Ray and Rebecca don’t mince words about what makes that approach so difficult, but they’ll also get you thinking about why it’s so sublimely and unquestionably worth it. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

What are the psychological building blocks that support a serial founder’s journey from ideation to massive growth to acquisition, to building again—and again? On this special episode of The Founder’s Mindset, Dr Gena Gorlin is joined by serial Silicon Valley entrepreneur Keith Schacht, who has founded and sold 4 technology companies. His latest, Mystery Science, was being used in over half of American elementary schools at the time of its acquisition by Discovery Education.  Now, he’s working on world-changing venture number 5. He joins Gena for a candid discussion of how he stays anchored to reality during that elusive, early search for product-market fit; why and when he made the decision to sell his company; and how he approaches starting all over again. Gena and Alice then debrief to explore what other founders can learn from his experience. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.

How do two very different co-founders reconcile—even leverage—their differences in motivation, temperament, and working style? Jack and Rob, the co-founders of social sports prediction platform Herd, join psychologist Dr. Gena Gorlin to explore the core ingredients of a functional co-founder relationship, and what they've done to turn their differences into a feature rather than a bug. Subscribe to The Founder’s Mindset so you never miss an episode. This is a podcast from Entrepreneur First. Learn more at joinef.com Thank you to Woolly Mammoth Media for consulting on and producing the show.