Written By Paula Pant
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 the Vice Dean of Entrepreneurship at Wharton Business School.
We’ve been planning this […]
By Paula Pant
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.
By Paula Pant
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.
By Paula Pant
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.
By Paula Pant
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!
By Paula Pant
Imagine saving nearly your entire paycheck while your rental properties cover your bills. That’s exactly where real estate investor Andrew finds himself — and yet he’s at a crossroads.
At FinCon, a personal finance conference, former financial advisor Joe Saul-Sehy and I sit down with Andrew and another attendee who bring their money dilemmas live on stage.
Andrew’s question seems simple at first: should he sell his index funds to pay off his rental mortgages? But the real story runs deeper.
He feels called to entrepreneurship and wants to quit his corporate job to pursue it full-time. He could achieve minimal financial independence (lean-FIRE) if he pays off the properties, but that might limit his options.
Next, Chris, a Gen X dad, opens up about his Gen Z kids’ gloomy money outlook. His 22 and 24-year-old children, especially his daughter, believe their generation “will never retire.” They see high inflation, expensive housing, and low wages as insurmountable obstacles.
This sparks a deeper conversation about generational perspectives. We note that similar fears existed 15 years ago when millennials entered the workforce during the Great Recession. Joe shares how he helped his own kids develop healthier money mindsets by introducing them to financial voices they could relate to, like Broke Millennial author Erin Lowry.
The discussion evolves into how today’s young people actually have more opportunities than previous generations — they can work remotely, start online businesses with minimal capital, and create multiple income streams through platforms that didn’t exist before. Chris’s daughter, for instance, sometimes makes $35/hour driving for DoorDash during peak times.
We wrap up by talking about the importance of focusing on what you can control and finding purpose beyond just retirement planning. As Andrew points out, it might be worse to spend the best years of your life doing work you don’t care about than to face uncertainty in retirement. The key is taking action on the things within your control while building toward long-term security.
Throughout the conversation, both guests share personal stories that illuminate their situations – from Andrew’s experience at an oil refinery that pushed him toward entrepreneurship to Chris’s daughter storing cash for taxes from her DoorDash earnings, showing she’s more financially aware than she might think.
By Paula Pant
If you want to learn about building wealth through entrepreneurship, you’ll enjoy this episode.
When Rachel Rodgers graduated from law school, she didn’t take the conventional path to working at a big law firm. Instead, she opened her own practice, specializing in intellectual property law. Many of her clients were entrepreneurs and small business owners.
Rachel quickly realized that many of her clients faced significant challenges in trying to grow their business. This ignited a new vision in her: to not just provide legal services but to help entrepreneurs achieve financial success.
She pivoted, shutting down her law practice to open Hello Seven, a company that offers comprehensive business strategies to help entrepreneurs reach seven-figure incomes.
She joins us today to share actionable insights that can help any entrepreneur, side hustler or small business owner reach seven figures in revenue.
By Paula Pant
If you’ve ever thought: “I’d love a business BUT …
“I don’t have TIME.”
“I don’t have MONEY.”
“I don’t have IDEAS.”
“I have TOO MANY ideas and I don’t know where to start.”
“I’m not technical.”
“I’m not creative or artistic.”
“I’m not good at sales.”
You’re not alone. Countless people don’t start businesses or side hustles for these reasons.
And they’re losing thousands — perhaps millions — in opportunity cost.
How much could you make if you started a side hustle that eventually scaled into a business? Possibly millions. Today’s guest, Noah Kagan, is living proof.
Noah was employee #30 at Facebook. His stock options, if fully vested, would be worth over $1 billion today.
(If you want to do the math — his stock options came to 0.1 percent of the company, which has a current market cap of $1 trillion.)
But Noah was fired just a couple months before his stock options vested. So rather than getting a billion-dollar payout, he got nothing.
He sank into a deep depression, eventually recovering with the help of a therapist who counseled him on how to reframe the experience.
Then he rolled up his sleeves and got to work. He became a serial entrepreneur, building multiple businesses. His most successful venture now makes $80 million in gross revenue, and his personal take-home is $3.3 million per year (which comes from a $200,000 annual salary and $3.1 million profit distribution.) His net worth is $36 million.
Not a billion, but still not too shabby.
Noah recently wrote a book called “Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours.”
He sits down with us (in person!) to share:
— how to find business ideas
— how to overcome objections and rejections
— how to scale
By the end of the episode, the common objections that you often hear — like “I don’t have time/money/ideas” — will be quashed.
Please enjoy!
By Paula Pant
As a society, we’re fascinated by stories of the rich. We hear news, see social media posts, and read books about how others become wealthy, how to maintain that status, and what their lifestyles look like.
But what if the media we’re consuming is misleading us?
Dr. Seth Stephens-Davidowitz’s research shows that the stories about the rich that dominate the popular press are misleading.
Stephens-Davidowitz holds a PhD in economics from Harvard University. He’s a data scientist and a New York Times bestselling author.
In today’s episode, we discuss the misleading stories around the rich. We unearth the truth behind those stories, using data rather than narrative.
We explore the types of businesses that quietly make people millionaires. We describe the ages, occupations and locations of people that become rich, and the unexpected paths they take to achieve this. And we share actionable takeaways that will help you do the same.
By Paula Pant
We sit down with Steve Chou, an accomplished entrepreneur who, alongside his wife, built two businesses that each bring in seven figures – and gives them the freedom to spend more time with their kids.
We delve into the challenges he faced in the early stages of his business and how he overcame these obstacles.
Additionally, Steve opens up about the personal and emotional aspects of running a business. He candidly discusses the fears, doubts, and sacrifices he and others have encountered during this transformational journey, emphasizing the importance of resilience and avoiding the comparison trap.
Whether you’re contemplating leaving your job to start your own venture or simply seeking inspiration from a seasoned entrepreneur, this episode with Steve Chou is a must-listen.
