Startups & Founding — what 180 operators said

The episodes

Stop Being a Hobby Hustler: How Derrick Hayes Took Big Dave’s Cheesesteaks from a Gas Station to a Franchise

How to Build a Profitable Turo Rental Fleet with George Madden

Turn Your Expertise Into Income: Mitch Matthews on Coaching, Speaking and the Authority Bridge

This One Platform Could Replace Your Entire Business Tech Stack | Robin Alex

Building Wealth With Other People’s Money: Justin Brennan on Multifamily Real Estate

Why Is Your Best-Selling Product Losing You Money?

The Self-Made Millionaire: Why Struggle Was His Greatest Advantage

Building a $25M Business From the Attention Economy with Dan Novaes

Most Businesses Should Never Raise Venture Capital | Navin Goyal

The Legal Tax Moves That Help Rich People Get Richer | Mark J. Kohler

From Finance to Netflix: Chris Allen on Influence, Sales, and Startups

Founder Lessons From Scaling, Going Public, and Rebuilding | Rick Jordan

How a Viral Congressional Trading Tracker Became a $1B+ Fintech Business | Autopilot

How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng

From Zero to Hero: Lessons on Rejection, Resilience, and Momentum

With $50K Left and a 40% Failure Rate, How FightCamp Rebuilt After the COVID Boom and Bust

Questions answered on startups & founding

Why doesn't Whoop pay athletes to wear its fitness tracker?

In their words

I was always meant to be an entrepreneur and I'll tell you one point of discrimination or illustration of this point, which is an entrepreneur, okay, a non entrepreneur will be in traffic and they'll come across a stop sign and they'll stop, right?

Michael Loeb · Serial Entrepreneur Michael Loeb: E-commerce, Sales, (25:58)

There's a reason why diamonds are made out of pressure. If there's a tipping point for every entrepreneur, it depends on what decision you want. You want to go down, you want to go up.

Amrinder Kamboj · Business Power Moves: Navigating High-Stakes Entrepr (0:00)

Well, here's something I've learned, and I think you can relate to this as an entrepreneur, is that history repeats itself. Different players, different names, different geographies, but history always repeats itself.

Arjun Rai · Arjun Rai, The CEO and Founder of HelloWoofy.com, Ta (14:12)

I'm a very poor entrepreneur at this point because everything that I made from the government went into these communities in this R&D.

James Merrill · James Merrill - Founder and Chief Executive Officer (25:12)

And so knowing how there are entrepreneurs who can't leave their desk. And that's not an entrepreneur. That's a job.

Mike Lazerow · SHOVELING SH*T: The Entrepreneur's Messy Path to Suc (24:24)

I think it's an entrepreneur. You can't get too high and you can't get too low.

Nate Kennedy · Nate Kennedy - CEO, Builder of Funnels, Master of Ad (17:00)

And I always say, if you're an artist, you're an entrepreneur, you just are.

Richard 'RB' Botto · Richard ‘RB’ Botto, Actor - Producer, Speaker, Autho (31:08)

I think people overstate the risks to starting a company or overstate the risks associated with being an entrepreneur because the process for becoming an entrepreneur for starting something reveals so much about who you are as a business leader, what your strengths are, your character, where your holds are, what you need to improve.

Brad Lea · Best Business Advice on the Planet with Guests Marc (25:47)

I look to expand founders, CEOs, whether it's whether it's co-founder communication, whether it's the vision of the company, whether it's making sure we're stress testing and keeping everyone firing like during the Olympics going for a goal medal as they're going through the whole stage of growth, right?

Andy Murphy · Andrew Murphy - Forbes Mental Performance Expert, Tr (19:29)

My story is the basic entrepreneurial story of I had absolutely no experience of being an entrepreneur, no plan on being an entrepreneur and no experience in the industry in which I started a business and just dove in head first.

Ben Spell · Trusting Your Gut | Building the Good Ranchers Brand (1:24)

I think the key to being an entrepreneur is perseverance. There's there's kind of what is your idea is the market right? And then are you willing to just stick it out? Because no matter what shit's going to be hard.

Allison Ferenci · Allison Ferenci - CEO and Co-Founder of Camera IQ (2:53)

My whole belief, if I can come in and I can just help you make some decisions as if I was your co-founder, but I'm not your co-founder.

Yarin Gaon · Why Is Your Best-Selling Product Losing You Money? (12:46)

What comes up again and again

The order of difficulty in a startup is not what founders expect: making a good product is easiest, selling it is harder, and leading a cohesive team is hardest. (With $50K Left and a 40% Failure Rate, H)
Founders should never run out of optimism, and it's fine to ask your co-founders to lend you theirs when you're carrying it alone. (With $50K Left and a 40% Failure Rate, H)
In the early days the founders responded to every single comment and message on Instagram and Facebook, which turned customers into organic micro-influencers who tagged friends. (Sawyer Hemsley - Cookie Crumbl: Organic )
Build a symbiotic rather than codependent relationship between the founder brand and the company brand, so the company can eventually stand on its own with the founder as spokesperson. (How To Be Unstoppable with Self Made CEO)
Founders in Michael's straw polls say they spend up to 75% of their time raising capital or keeping existing investors happy, which he calls the worst possible use of a founder's time. (Serial Entrepreneur Michael Loeb: E-comm)
Founders should challenge their own assumptions: Tony tells entrepreneurs their first 10 ideas suck, and Ryan reframes it as falling in love with the customer's problem, not the idea. (Build a Brand That Sells: Lessons From B)
Fewer than 2% of companies actually need venture capital; Navin actively discourages most founders from taking money from a fund and suggests staying scrappy or using in-kind services instead. (Most Businesses Should Never Raise Ventu)
Bringing experienced executives in-house through the investor can reduce how much money a company needs to raise, cut wasted experimentation, and reduce how much equity the founder gives away. (Most Businesses Should Never Raise Ventu)
Loud Capital reviews decisions and spend roughly monthly with founders, asking whether they're getting bang for the buck, and holds itself accountable in the same review. (Most Businesses Should Never Raise Ventu)
The ideal venture-backed founder is ambitious and humble, willing to be outgrown by their own company and managed alongside executives who may be more experienced. (Most Businesses Should Never Raise Ventu)

Questions this topic answers

All 186 episodes

Search within

Oct 9, 2026

Who is the founder of Big Dave's Cheesesteaks?

Why do founder-led businesses stall between $1 million and $5 million in revenue?

When should a founder pivot the business model?

How can a startup raise less money and give away less equity?

What kind of founder is a good fit for venture capital?

What is the most important business skill for founders?

Should a founder put personal money into a failing company?

What gives an AI startup a defensible advantage?

All 186 episodes

Big Dave's Cheesesteaks: Gas Station to Franchise

How to Build a Profitable Turo Fleet With George Madden

Mitch Matthews on Turning Expertise Into Income

Robin Alex on Replacing Your Business Tech Stack

Justin Brennan on Multifamily and Other People's Money

Why Your Best-Selling Product Is Losing You Money

Moses Heredia: Why Struggle Was His Biggest Advantage

Blue Moon and White Claw Brand Lessons With Tony Vieira

Dan Novaes: Turning Phone Attention Into Income

Why Most Businesses Should Never Raise Venture Capital

Legal Tax Moves That Help the Rich Get Richer

Mrs. Meyer's Founder Monica Nassif on Disrupting a Category

Chris Allen on Netflix Fame, Sales, and Startup Pivots

Rick Jordan on Going Public, Failing, and Rebuilding

Pelosi Tracker to $1B Fintech: Chris Josephs of Autopilot

Anya Cheng on AI, Data Moats and the Future of Shopping

Rejection, Resilience and Momentum: From Zero to Hero

FightCamp's Khalil Zahar on Surviving the Valley of Death

Scott Clary on Using AI to Build Wealth Faster

AI, Aging, and the $2.5M Long-Term Care Problem

Iran War, AI and the Small Business Economy

Real American Beer's Playbook for Breaking Into Big Beer

AI for Small Business Growth with Dave Charest

Ken Goldin on Attention, Hype and Collectibles

Jamil Damji: No One Is Coming to Save You

Kaylor Betts: Stop Consuming, Start Winning

AI Productivity vs AI Security: The Human Risk

Mike Sancho: From Expelled to Passive Income Builder

Anik Singal on Surviving an FTC Investigation

Jen Gottlieb: Authenticity Is Authority

Agentic AI and Atoms: Ideas to Revenue With Ethan Ouyang

How to Build a Website That Converts With Sam Dunning

Scott Scovill on Turning Fear of Failure Into Tenacity

Derrick Hayes: Big Dave's Cheesesteaks Franchise Story

Inside the Rental Car Business with George Madden

Build the Business First, Then the Personal Brand

Mark J. Kohler on How the Rich Use Tax Strategy

Matt Higgins: Why a Plan B Kills Your Plan A

Brad Blazar on Raising Capital With Other People's Money

Podcasting's Next Era with Jeff Umbro