Would you trust someone with your money if the “interview” for the job was a fifty-page pitch deck and a decade-long commitment?
That’s essentially what happens every time someone becomes a limited partner in a venture capital fund.
I sat […]
Tag: entrepreneurship
#732: Why The Customers Nobody Wants Are the Best Ones to Sell To, with David Bell
Why can’t you buy Vegemite in Philadelphia — and what does that have to do with building a wildly profitable online brand?
There are invisible forces shaping what you buy. Where you live. Who’s around you. What your local stores do — […]
#731: Is AI Making You Dumber? With Lorraine Marchand
IQ scores have been sliding since 1970, and Lorraine Marchand thinks AI is quietly speeding that up.
She’s also in the middle of building an agentic AI board of directors for her own company — one she jokes could someday vote to fire her.
Lorraine teaches […]
#675: The Myths We Believed About Startups [GREATEST HITS]
Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid […]
#652: Why High Earners Stay Broke – with Rose Han
What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke?
That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path […]
The 7 Types of Entrepreneurs (You’re Probably One of Them)
We cover five pillars: Financial psychology, Increasing your income, Investing, Real estate, and Entrepreneurship. It’s double-ii FiiRE.
Today, we’re diving into Pillar Five: Entrepreneurship.
Pillar V | Entrepreneurship
Earlier this month, we covered the first four pillars in this newsletter.
But it wasn’t until Friday that we published our long-awaited interview with Lori Rosenkopf, the Vice Dean of […]
#634: Wharton Professor: The 7 Hidden Types of Entrepreneurs, with Lori Rosenkopf
Picture this: you’re 26 years old, fresh out of Wharton, and you decide to start a business with two friends. You spend years building a digital marketing firm that eventually works with Dollar Shave Club and Madison Reed. You bootstrap the entire thing without taking a dime of venture capital funding.
That’s exactly what one Wharton graduate did — and her story represents the reality of entrepreneurship that most people never hear about.
Lori Rosenkopf, a management professor at Wharton Business School and head of Venture Labs, joins us to shatter the biggest myths about starting a business. The Mark Zuckerberg college dropout story? It’s not just rare — it’s misleading.
Research shows that the most successful entrepreneurs, those in the top 0.1 percent of venture-backed firms, average late 30s to early 40s when they start their companies. Many continue launching businesses into their 50s and 60s.
Your age and corporate experience isn’t holding you back from entrepreneurship — it’s actually giving you an advantage.
Rosenkopf breaks down seven different types of entrepreneurs, from disruptors who overturn entire industries to bootstrappers who build profitable businesses using their own resources. You’ll hear about a founder who disrupted the hair color industry in her 50s with Madison Reed, and a banker who built an entire financial services division inside Square.
We cover the rise of direct-to-consumer brands in 2013, why 80 percent of entrepreneurs are bootstrappers, and how artificial intelligence is creating new opportunities for people to start businesses without massive upfront investments.
Rosenkopf explains her “six Rs” of entrepreneurial thinking: reason, recombination, relationships, resources, resilience, and results. She argues that most people already think entrepreneurially without realizing it — even parents who optimize their family routines are solving problems through innovation.
We explore the world of “intrapreneurs” — people who build new businesses within established companies — and discuss acquisition entrepreneurship, where people buy existing small businesses instead of starting from scratch.
Whether you want to start a side hustle, position yourself for a promotion, or eventually launch your own company, Rosenkopf’s framework shows multiple paths to creating value through innovation.
#612: How to Know If You’re Cut Out for Entrepreneurship Before You Risk Everything, with Grant Sabatier
Grant Sabatier never worked in retail, never worked in a bookstore, and had no idea what he was doing when he opened Clintonville Books in Columbus, Ohio.
But that’s exactly the point.
The experiment required 1,200 hours of solo work — measuring spaces, moving 40,000 books, and navigating city regulations.
But it taught him something crucial: even experienced entrepreneurs face steep learning curves when they try something new.
The serial entrepreneur and author of “Inner Entrepreneur” joins us to share his unconventional journey from online businesses to brick-and-mortar retail.
He also explains why he believes everyone will become an entrepreneur within the next decade — whether they want to or not.
We dive deep into Sabatier’s framework for the four stages of entrepreneurship.
The first stage is experimental — you’re figuring out how entrepreneurship feels and testing ideas with minimal risk. Most people skip the crucial research phase and invest too much money too quickly.
The second stage focuses on building sustainable systems as a solopreneur. Thanks to AI and modern tools, Sabatier launched a new website in 10 minutes recently — something that would have taken two weeks just five years ago.
Stage three involves intentional growth. Sabatier warns against the common trap of scaling rapidly without considering how you want entrepreneurship to fit into your life.
The final stage is empire entrepreneurship — using cash flow from successful businesses to acquire other companies rather than investing in traditional assets like stocks or real estate.
Throughout our conversation, we explore the most common reasons businesses fail, how to avoid fragmented attention, and why Sabatier believes your story is your competitive advantage in an AI-driven world.
#565: Codie Sanchez: From Wall Street to Washing Machines
When Codie Sanchez worked in finance, she wasn’t planning to buy a laundromat. But facing 60-70 hour workweeks and realizing she didn’t want her boss’s job, she started looking for an exit strategy. Instead of buying a fancy car during her “midlife crisis,” she purchased that first laundromat – a decision that would lead her to acquire multiple laundromats, car washes, and other local businesses.
Codie joins us to break down how regular people can buy and run profitable local businesses, even without previous ownership experience. These “Main Street” businesses – think laundromats, car washes, landscaping companies, and other local services – often generate steady cash flow without requiring complex technology or massive scale.
She shares eye-opening stats about business ownership in America: while 80 percent of Americans owned a business in the 1800s, today that number has dropped to just 6 percent. Meanwhile, private equity firms have increased their ownership of small businesses from 4 percent in 2000 to 20 percent by 2020.
But there’s good news for aspiring business owners. Codie breaks down 21 different ways to finance a business acquisition, from seller financing to equipment loans. She explains that 60 percent of businesses sell with some form of seller financing, making ownership more accessible than many realize.
Want to avoid common pitfalls? Codie introduces her RICH framework:
– Research: Define what type of business fits your goals and skills
– Invest: Get skin in the game, but never risk bankruptcy
– Command: Use systems and metrics to avoid accidentally buying yourself a job
– Harness: Build toward bigger goals if desired
She emphasizes starting small — master one business before attempting to build an empire. A successful acquisition requires understanding the “roadmap to making money” – the 5-7 key steps that drive profit in any business.
The numbers tell an encouraging story: while 90 percent of startups fail within 10 years, small business acquisitions have a 75-95 percent success rate. Codie attributes this to buying proven business models rather than starting from scratch.
Perhaps most importantly, she challenges the notion that “boring” businesses can’t generate serious wealth. From a roofing company founder becoming one of the world’s wealthiest women to a garbage collection entrepreneur building a billion-dollar enterprise, Main Street businesses have created numerous millionaires and billionaires.
Want to learn more? Check out Main Street Millionaire.
#559: Q&A: Should We Ditch Rental Properties Entirely?
An anonymous caller, whom we name “Samantha,” and her husband are financially strained and feeling torn. Shortly after purchasing two rental properties, their income dropped dramatically. Should they sell?
Tina is a full-time environmentalist. She’s worried that her index funds don’t align with her values on sustainability. Is there a world where she can be a savvy investor and fight climate change?
Another anonymous caller, whom we name “Sarah,” is excited and uncertain about her growing business. Should she hold steady or invest more resources into it? And how does she know if she’s making the right call?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
Enjoy!
