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 face-to-face interview with Lori Rosenkopf since early April, and after publishing it last Friday, we’re excited to dive into her insights.
She holds an endowed chair at Wharton — the Simon and Midge Pally Professorship — which is one of the highest faculty honors.
She’s also the faculty director for Venture Lab, which is UPenn’s home for student entrepreneurs.
And she just wrote a book called “Unstoppable Entrepreneurs” in which she highlighted seven paths people can take towards entrepreneurship.
The mainstream media often focuses on just one of the seven paths — The Disruptor — making people forget there are six other paths that might actually work better for them.
The Disruptor is the person who raises massive capital to build mega-businesses that reshape entire industries.
Think: Facebook/Meta, Uber, Lyft, Airbnb.
ok. cool. 🙂
But here’s the thing: there are six other paths that might be a better fit for you.
Let’s unpack these.
First, The Bootstrapper represents 80 percent of small businesses in the U.S.
No investors, no loans, just hard work and reinvested profits. This is the the real backbone of American business.
These businesses are entirely self-funded. The founder invests in themselves and their ideas, starting the business with some savings and running a lean operation by investing more time than money.
Founders often start these part-time or on-the-side while working a day job. They reinvest every dime back into the business until it’s doing well enough that they can go full-time.
These businesses grow more slowly, but that growth is more stable.
Next, there’s The Social Entrepreneur, where purpose and profit blend together.
The first step is raising money. These are often funded by pitch competitions, philanthropic grants, incubators and accelerators that focus on social enterprises, crowdfunding platforms, or social impact investors.
(These could also be bootstrapped, but please know that there are plenty of seed funding sources for people who are serious about social impact entrepreneurship.)
Then there’s The Tech Commercializer. These are the people who bridge the gap between technological innovation and profitability.
They find academics or researchers who have promising new discoveries, and operate in that Venn diagram intersection between tech innovation and business acumen.
Their focus isn’t developing original ideas (R&D), but rather the business side of bringing those ideas to market. Universities are sitting on billions of dollars worth of research that never makes it to consumers — that’s where these entrepreneurs come in.
Next there’s The Funder, the people who put together private funds that invest in other entrepreneurs and creators.
Many entrepreneurs start by creating their own business and later become funders, as a way not just to provide capital, but also to provide mentorship and guidance to the next generation.
Many successful bootstrappers eventually gravitate toward this role — it’s a natural evolution from building your own company to helping others build theirs.
There’s also The Acquirer, a path that’s blown up in popularity online in the last few years.
As more Baby Boomers retire — many of whom have children who want to pave their own path, and don’t want to work in the family business — there will be increasing opportunities to acquire strong small businesses.
We discussed this at length in our in-depth interview with Codie Sanchez (run time: 1 hour, 40 min without ads). Watch that for a deep dive.
Finally, there’s The Intrapreneur. The word is a portmanteau of “inside” and “entrepreneur,” and it refers to employees who develop ideas and products within an existing company.
Essentially, it’s a reference to employees who think and act in an entrepreneurial way within the scope of their full-time W-2 job.
There’s huge appeal to this, because it holds a lot of the creativity, innovation, and fun, without the pressure.
But it also lacks the upside, and you need to find the right company that would be open to this in the first place.
The great thing about these seven paths? There’s no hierarchy.
The bootstrapper building a steady $2 million business isn’t less successful than the disruptor raising $50 million. They’re just playing different games.
The question isn’t which path is “best” — it’s which path is best for you, right now, with your current resources and goals.
You don’t have to hold to just one path forever. You can start with whatever fits you right now and change in the future as your priorities and circumstances shift.
And you can also pursue two of these paths simultaneously. Maybe you’re an Intrapreneur at your day job and a Bootstrapper in the evenings and weekends.
Maybe you’re an Acquirer who wants to buy a small business and a Social Entrepreneur as a key value within that.
Maybe you’ve already been a Bootstrapper and now you want to transition into being a Funder so that you can pay that knowledge forward.
The point is this: entrepreneurship isn’t a one-size-fits-all journey.
Take an honest look at your situation — your risk tolerance, your resources, your timeline — and choose the entrepreneurial path that makes sense for your life right now.
You can always evolve later. In fact, you’ll almost certainly evolve later, because these paths aren’t static.
And that means — you don’t need to wait for the ‘perfect’ path or the ‘right’ moment. You just need to start (if you want to).
