Entrepreneurship

Rubenstein says entrepreneurs constantly expect something bad to happen and he still worries every day.

“No, because if you're an entrepreneur, you always think something bad is going to happen”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 20:12

Rubenstein argues that company builders share extraordinary self-confidence.

“if you go back and look at anybody that built a company, they have self-confidence that is staggering”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 15:58

Rubenstein asserts that nearly all U.S. startups fail within five years.

“remember 99.9% of the companies that started the United States are not in business five years later”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 6:33

Rubenstein says he started Carlyle at 37 because he had read that people who have not started a company by that age probably never will.

“If you haven't done it by 37, I read, you probably will never start a company”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 5:32

Friedman cites Nick Saban's view that complacency leads to bad decisions as a reason not to coast after success.

“He said, complacency leads to bad decisions, bad decisions lead to bad outcomes”

The Dylan Gemelli Podcast: Episode #168: He Turned Down Shark Tank and Built a $300M Business... But Was It Worth It? Featuring Nick Friedman (Sep 30, 2026) · Listen from 50:19

Friedman argues that growing his existing $300 million business by 10 percent outweighs starting new ventures.

“So if we grow that business... 10%, that's $30 million growth. Like, you know how hard it would be to get a business to go from zero to $30 million”

The Dylan Gemelli Podcast: Episode #168: He Turned Down Shark Tank and Built a $300M Business... But Was It Worth It? Featuring Nick Friedman (Sep 30, 2026) · Listen from 45:53

Friedman admits he held his organization back by generating too many ideas and forcing them on his team.

“I've been somebody that's sort of holding the organization back because I'm coming up with too many ideas and I'm forcing them on the organization”

The Dylan Gemelli Podcast: Episode #168: He Turned Down Shark Tank and Built a $300M Business... But Was It Worth It? Featuring Nick Friedman (Sep 30, 2026) · Listen from 45:53

Ryan says New York is booming, with many people moving from Europe to start companies there.

“I see so many people moving from Europe, coming to New York, starting up companies”

The Tim Ferriss Show: #884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More (Sep 24, 2026) · Listen from 1:20:37

Ryan says he pursues an idea if his intellectual 'business crush' on it persists for about two weeks, without building a business model.

“And if that sticks with me for like two weeks, I generally do it”

The Tim Ferriss Show: #884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More (Sep 24, 2026) · Listen from 39:43

Ryan says he has avoided e-commerce since Gilt because he views the problem as already solved.

“I can get anything delivered to my house in like 27 seconds. I can return it. It's inexpensive. So I don't know how to do better”

The Tim Ferriss Show: #884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More (Sep 24, 2026) · Listen from 21:44

Rothblatt advises entrepreneurs to pursue projects that can be fully commercialized within five years.

“come up with a project, a program, a technology, a service that can be completely commercialized within a five-year period”

Moonshots with Peter Diamandis: Martine Rothblatt: Growing Unlimited Organs, AI Consciousness, & Digital Personhood by 2030 (Sep 15, 2026) · Listen from 47:55

Rothblatt says she treats each rejection as information that makes her smarter and welcomes criticism.

“I look at each no as a way to make me smarter. So I'm a person that's very open to criticism”

Moonshots with Peter Diamandis: Martine Rothblatt: Growing Unlimited Organs, AI Consciousness, & Digital Personhood by 2030 (Sep 15, 2026) · Listen from 7:13

Rothblatt argues that a venture changes the world only if its technology can be scaled to affect billions of people.

“So is that a technology that can be scaled to billions of people? If it can, then you're going to change the world”

Moonshots with Peter Diamandis: Martine Rothblatt: Growing Unlimited Organs, AI Consciousness, & Digital Personhood by 2030 (Sep 15, 2026) · Listen from 10:19

Frisella argues anger at capitalism should target the handful of richest people rather than local business owners.

“Be mad at those fucking ten people. Don't be mad at your local guy who's trying to make it and create jobs”

REAL AF with Andy Frisella: 1022. Q&AF: Fitting In While Growing, Finding Purpose In Success & Hiring Your First Employee (May 4, 2026) · Listen from 41:39

Frisella argues the therapy industry is predatory because it profits from keeping clients in a victim mindset.

“They have no interest in making you any better because they lose their income. So they have a direct interest in keeping you in victim mindset”

REAL AF with Andy Frisella: 1015. Andy, Chad Bianco & DJ CTI: Communists At No Kings Rally, Ground Operations In Iran & Tiger Woods DUI (Mar 31, 2026) · Listen from 1:29:34

Frisella argues that young people today have more entrepreneurial opportunity than ever and says he earned $58,380 total in his first ten years in business.

“i made $58,380 my first 10 years combined. Not every year. The first 10 years, I made $695 a month for seven fucking years”

REAL AF with Andy Frisella: 1015. Andy, Chad Bianco & DJ CTI: Communists At No Kings Rally, Ground Operations In Iran & Tiger Woods DUI (Mar 31, 2026) · Listen from 1:31:02

Sacks says the best way to become more profitable is to ask for more, raise prices, and cut underpaying clients.

“your prices, cut clients who are sucking you dry and not paying you enough”

Young and Profiting (YAP) with Hala Taha: Entrepreneurship and Self-Improvement Podcast: Haley Sacks: The American Dream Is Dead! The New Rules for Building Real Wealth | Finance | E419 (Oct 5, 2026) · Listen from 1:02:17

Sacks argues women in particular should focus on earning more rather than cutting spending, because women are underpaid.

“I think women are severely underpaid. We don't ask for enough”

Young and Profiting (YAP) with Hala Taha: Entrepreneurship and Self-Improvement Podcast: Haley Sacks: The American Dream Is Dead! The New Rules for Building Real Wealth | Finance | E419 (Oct 5, 2026) · Listen from 26:56

White attributes much of his success to timing rather than luck.

“I wouldn't call it luck. I'd call it timing. Everything in life is about timing”

The Diary Of A CEO with Steven Bartlett: Dana White: This Generation Thinks You Can Build A Business From Home, It's Impossible! (Oct 5, 2026) · Listen from 1:05:50

White says anyone starting a business to gain more free time has chosen the wrong path.

“If you're looking to start your own business because you want more time to yourself, you are picking the wrong thing to do”

The Diary Of A CEO with Steven Bartlett: Dana White: This Generation Thinks You Can Build A Business From Home, It's Impossible! (Oct 5, 2026) · Listen from 11:52

Levesque advises focusing on one acquisition channel, one conversion method and one offer until reaching a million dollars.

“Pick one channel, one way to attract, one way to convert, and one way to serve. And do that until you get to a million dollars”

the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 36:56

Levesque argues a few-million-dollar lifestyle business may be more aspirational than a $20 million business demanding constant scaling.

“a business that does a few million dollars a year that provides a great lifestyle for you and your family is, in my experience, you know, perhaps more aspirational”

the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 30:14

Neumann predicts that artificial intelligence will enable almost anyone to start a business.

“With AI coming in, everybody's about to be a founder. Everybody can start a business”

The Diary Of A CEO with Steven Bartlett: Adam Neumann: The Real Story Behind WeWork, A $4 Billion Cab Ride, And Surviving A $460 Million Debt (Sep 28, 2026) · Listen from 1:19:31

Neumann says that among the many successful people he knows, none became fulfilled by reaching a financial number or material goal.

“I have not seen one that got happy or fulfilled from attaining a number or a material thing”

The Diary Of A CEO with Steven Bartlett: Adam Neumann: The Real Story Behind WeWork, A $4 Billion Cab Ride, And Surviving A $460 Million Debt (Sep 28, 2026) · Listen from 16:56

Yeung argued founders take risks hired CEOs won't and should stay involved in all key decisions.

“the founders were able to take risks that a CEO wouldn't be able to take”

My First Million: How we scaled to $100M in under a year (ft. IM8 co-founder Danny Yeung) (Sep 7, 2026) · Listen from 47:01

Yeung said his board opposed entering supplements and he offered to resign if wrong.

“If I'm wrong, I'm going to resign. I'm going to quit, right? That was my position”

My First Million: How we scaled to $100M in under a year (ft. IM8 co-founder Danny Yeung) (Sep 7, 2026) · Listen from 11:14

Rexius says a CEO at his corporate job told him he needed to run his own ship, which shaped his return to entrepreneurship.

“you need to be at the helm. You need to have boundless opportunity. And the only way you can do that is to run your own ship”

Mick Unplugged: Unleash Your Power: Integrating Life & Work with Tim Rexius (Jul 2, 2026) · Listen from 40:34

Rexius argues that entrepreneurs who plateau do so because they try to outthink hard work, which he says is impossible.

“the vast majority of entrepreneurs who struggle and get stuck at that plateau level, it's because they're spending all their time trying to out think hard work”

Mick Unplugged: Unleash Your Power: Integrating Life & Work with Tim Rexius (Jul 2, 2026) · Listen from 12:57

Okereke says he founded two black-car chauffeur services, one in Miami and one in New York.

“I've started two car companies. They're black car chauffeur services, like private chauffeur services, one in Miami”

Unblinded with Sean Callagy: Bobby Okereke: The Mindset Behind NFL Success (Jun 11, 2026) · Listen from 44:35

Okereke says he aims to convert his influence as an athlete into sustainable infrastructure in business, finance, and charity.

“i'm trying to be strategic and think about how i can convert this influence that I have into sustainable infrastructure, whether it's business”

Unblinded with Sean Callagy: Bobby Okereke: The Mindset Behind NFL Success (Jun 11, 2026) · Listen from 43:44