An Entrepreneur's Guide to the Galaxy: What an Investment Wizard Taught Me About Business

The Motley Fool’s David Gardner has been picking stocks for 30 years. His cost basis on Amazon? 16 cents. On Nvidia? Pennies. But here's what surprised me during our conversation for my Founding DC podcast: this investment wizard's best advice isn't about stocks – it's about building businesses and the beautiful construct of commerce that advances humanity, aka, one of my favorite topics: conscious capitalism. 

LISTEN TO THE FULL FOUNDING DC PODCAST WITH DAVID GARDNER

"I'm a better investor because I'm a businessman, and I'm a better businessman because I'm an investor," Gardner says, quoting Warren Buffett. After reading his soon-to-be-released book, Rule Breaker Investing: How to Pick the Best Stocks of the Future and Build Lasting Wealth, which I think should be called “An Entrepreneur’s Guide to the Galaxy,” and diving deep into his philosophy during our podcast chat, I realized every entrepreneur needs to think like an investor.  

Lesson 1: Don't Fight Goliath – Outsmart Him 

"The only way David beats Goliath is by not following the rules," Gardner explains. When The Motley Fool started, they willingly called themselves "fools" – a fool and his money are soon parted. Why would anyone do that? 

Because it perfectly set up the framework to spend the rest of their business life proving why what they were doing was right. They didn't try to out-Wall Street Wall Street. They ignored the establishment's rules and built something entirely different. 

Gardner draws this insight from an unexpected source – art. "There's a beautiful book called Drawing on the Right Side of the Brain by Betty Edwards," he explains. "I draw very, very poorly, but I got a little bit better when I started realizing it's not the thing itself you're drawing. It's actually the negative space around the thing that you're drawing." The same principle applies to business: sometimes the most important insights come from studying what is not there. Gardner frames this with a powerful question:

What is something that you believe that most people don't believe? That's just a fun question for anybody. For entrepreneurs, if you can answer that question with a business, that's one of the most powerful things you could do.

The Entrepreneur's Lesson: Never try to out-Goliath Goliath. Start with what you believe that others don't. Look for the empty spaces – the problems no one else is solving, the customers no one else is serving, the markets everyone else has written off. The most interesting place in any industry is where no competitors are standing. That empty space isn't a warning sign – it's your invitation to build something the world doesn't yet know it needs. 

Lesson 2: Your Biology Is Working Against You 

Here's a brutal truth: The pain of loss is three times as strong as the joy of gain. We're wired to run when the bushes shake, because our ancestors are the people who ran while the others got eaten. But in business, Gardner says, this fear response is usually wrong:

That pit in your stomach when you're about to launch? That's not danger – that's opportunity disguised as risk. 

The Entrepreneur's Lesson: Train yourself to run towards the fear, not away from it. That uncomfortable feeling when you're considering a big move? That's probably your compass pointing toward growth. As Gardner puts it: "In today's world, there's probably not a tiger behind the bush. There's probably an opportunity." 

Lesson 3: Back Genius, Not Just Talent 

Arthur Schopenhauer's distinction changed how Gardner invests: "Talent hits a target no one else can hit. Genius hits a target no one else can see." 

Gardner doesn't just look for skilled operators. He hunts for visionaries who see possibilities others can't imagine. For example, John Mackey when everyone thought organic food was hippie nonsense and started Whole Foods anyway. 

The Entrepreneur's Lesson: Whether you're hiring, partnering, or choosing co-founders, don't just look for competence. Look for people who see opportunities that don't exist yet. Back the dreamers who make others uncomfortable. 

Lesson 4: Live in the Future, Invest in the Present 

Gardner's license plate reads "FUTURE." He thinks from tomorrow backwards to today, asking: "How do I want the world to look, and what needs to happen now to get there?" 

This isn't wishful thinking. It's strategic positioning. As a DC native who's built his business in the heart of one of America's entrepreneurial engines, Gardner understands something profound about commerce: business is beautiful because it's voluntary. "You're good at this, let me buy that from you. I'm good at that, you can buy that from me," he explains. "Look at how it's advanced humanity over the last few centuries." 

The Entrepreneur's Lesson: Stop reacting to today's problems. Start building tomorrow's solutions. And remember – every transaction is a vote for the kind of world you want to create. An entrepreneur’s motive is personal, and as long as it is intentional, it can serve you well. As you think about intentionality, decide where you are on this journey, which reminds me of a blog I wrote long ago, which could still be of use to some: The Capitalist’s Journey to Consciousness: Lessons from the Yellow Brick Road.   

Lesson 5: Optimism Is Rational 

Gardner's most powerful insight? "Optimism is the rational choice." 

Every generation thinks they're living in the end of times, but humanity keeps getting better. The stock market trends up and to the right over any meaningful timeframe, not because of luck, but because people keep working to make things better. 

The Entrepreneur's Lesson: Your job isn't to fix everything that's broken. Your job is to build something that makes tomorrow better than today. Or, as Gardner says:

The world needs what you're building, even if it doesn't know it yet. 

The Ultimate Lesson: Write Things Down 

David Gardner spent 15 years taking notes before writing his book, Rule Breaker Investing: How to Pick the Best Stocks of the Future and Build Lasting Wealth, which will be released in September 2025.  

The Entrepreneur's Lesson: Gardner’s advice for entrepreneurs and frankly everyone: Start writing things down today. Your future self will thank you. So, here I am taking the advice and getting back to regular writing and blogging. 

LISTEN TO THE FULL FOUNDING DC PODCAST WITH DAVID GARDNER