Most aspiring entrepreneurs focus on the wrong things.

They obsess over perfect business plans, prestigious connections, and impressive credentials. They study successful founders, analyze market opportunities, and craft detailed financial projections. They believe preparation equals success.

They’re wrong.

According to John Harthorne, who built MassChallenge into the world’s largest startup accelerator before founding Two Lanterns Venture Capital, entrepreneurship isn’t about having all the answers. It’s about possessing what he calls an “unreasonable attachment” to a problem you can’t ignore.

During our conversation, Harthorne shared insights that fundamentally challenge conventional startup wisdom. His perspective, forged through evaluating thousands of entrepreneurs and investing in dozens of companies, reveals why most ventures fail—and how the successful ones break through.

Here are five principles that separate entrepreneurs who build lasting companies from those who never get off the ground.

1. Solve Problems That Haunt You

The most successful entrepreneurs don’t choose problems—problems choose them.

“You have to have an unreasonable attachment to some outcome,” Harthorne explains. This isn’t about market size or profit potential. It’s about encountering a problem so fundamental, so personally frustrating, that ignoring it becomes impossible.

Harthorne’s own epiphany came during the 2008 financial crisis. Lying awake at night, frustrated by an economy focused on “fighting over slices of existing pie” rather than creating new value, and thinking “Somebody needs to fix this … the President, Congress, the Fed, maybe Wall Street …” he suddenly reached a powerful realization: “Wait! I’m somebody. Why don’t I fix it?”

That moment of personal responsibility—not market analysis or entrepreneurial ambition—sparked MassChallenge.

The litmus test: Ask yourself, “If I don’t solve this problem, who will?” If you can easily name someone else, find a different problem. The best entrepreneurs solve problems that feel uniquely theirs to address.

Take action: Before writing business plans or seeking funding, share your problem/solution proposal with as many close friends and advisors as possible to let them help you understand which parts of your plan are most compelling and which parts are downright stupid. Every initial plan is wrong, so don’t take offense—seek solutions and ask for alternative options when people identify elements of your plan that may not be realistic.

2. Fail Fast, Learn Faster

Your first business plan is guaranteed to be wrong. Embrace this reality.

Harthorne learned this through public humiliation. His initial MassChallenge pitch involved securing $50 million in government funding to run a venture fund—despite having zero investment experience.

“We had embarrassing meetings,” he recalls. “You would go and pitch, and people would just intellectually destroy you. You’d walk out thinking, ‘That was terrible—we are way off.'”

Instead of retreating to perfect their pitch, Harthorne and his co-founder scheduled more meetings. Thousands of them. Each rejection became education. Each criticism became course correction.

“One week of real-world testing teaches more than months of theoretical planning.”

This approach—which Harthorne calls “bias toward action”—transforms failure from something to avoid into something to accelerate. The faster you fail, the faster you learn what actually works.

The principle: One week of real-world testing teaches more than months of theoretical planning. Your job isn’t avoiding failure—it’s failing efficiently.

Take action: Commit to 50-100 stakeholder conversations in 30 days— including potential customers and investors. Don’t pitch—listen. Ask what problems they face, how they currently solve them, and what solutions they’d pay for. Let their responses reshape your assumptions.

3. Make Pies, Don’t Fight for Slices

The most profound business insight often comes from the simplest frameworks.

Every company, Harthorne learned in business school, has two fundamental responsibilities: create value and capture value. “Think of creating value as making pie—you are making something new and valuable that benefits the world,” he explains. “Capturing value is keeping a slice for yourself as compensation for your contribution.”

Most entrepreneurs focus primarily on capturing value—competing for market share, undercutting competitors, optimizing margins. They’re fighting to get a bigger slice of the existing pie.

Successful entrepreneurs do something different: they make entirely new pies.

“Entrepreneurs are the ultimate pie makers,” Harthorne says. “They start from nothing and often create entirely new industries that never existed before, creating massive amounts of value.”

When you focus first on value creation, value capture becomes easier. When you only focus on making money, you’re trapped in zero-sum competition.

The reframe: Before every pitch or product decision, ask: “Am I expanding the market or just competing within it?” The best opportunities don’t steal customers—they create new categories of customers.

Take action: Map your competitive landscape, then identify what new value you could create that doesn’t currently exist. Focus on the gaps, not the overlaps.

4. Get Comfortable with Discomfort

Entrepreneurship requires developing an unusual relationship with embarrassment.

Most people avoid situations where they might look foolish. Entrepreneurs must actively seek them out.

Harthorne’s early fundraising meetings were “terribly embarrassing” because he was “constantly exposing our own stupidity and naivete.” But this wasn’t a bug in his process—it was the feature that made everything else possible.

“That’s how we got smart,” he explains. “The market taught us what would work through thousands of awkward conversations.”

“Your comfort zone is the enemy of learning.”

Each embarrassing encounter provided data—direct feedback from the market about what was wrong and what needed fixing. Most people interpret embarrassment as a signal to stop. Entrepreneurs interpret it as a signal to continue, just differently.

The mindset shift: Embarrassment isn’t failure—it’s education. Your comfort zone is the enemy of learning. Growth requires regularly putting yourself in situations where expertise is uncertain and outcomes are uncomfortable.

Take action: Schedule one potentially embarrassing professional interaction each week. Pitch someone out of your league. Ask for feedback on rough work. Request introductions you might not deserve. Track what you learn from each uncomfortable moment.

5. Develop Unreasonable Persistence

The difference between entrepreneurs who succeed and those who quit isn’t intelligence, resources, or luck—it’s attachment to outcome.

Even the best venture capitalists see 60% of their investments return zero. Most startups fail. Most entrepreneurs eventually give up.

But some don’t.

“In some of my failed investments,” Harthorne observes, “the founders gave up. They said, ‘This got really hard. I don’t see a path to making a billion dollars anymore, so I just don’t want to do it.'”

The entrepreneurs who succeed possess what Harthorne calls “unreasonable attachment”—a refusal to accept failure when the problem remains unsolved. This isn’t blind optimism. It’s deeper: a conviction that the problem matters too much to abandon.

The foundation: Resilience isn’t a personality trait—it’s the natural result of caring about something bigger than yourself. When you’re solving a problem you can’t ignore, quitting becomes literally unthinkable.

Take action: Write down exactly why solving your chosen problem matters to you personally. When you hit inevitable setbacks, return to this document before making any decisions about continuing or quitting.

The Execution Imperative

“You can’t think your way to becoming better,” Harthorne concludes. “You have to do it.”

Consider learning to ride a bike. Imagine trying to master cycling by reading books and articles and planning out a strategy on a whiteboard versus just getting on the bike and trying to ride it. Which approach do you think will yield faster, better results?

This philosophy—action over analysis, iteration over perfection, learning over planning—separates entrepreneurs who build meaningful companies from those who remain perpetually preparing to build them.

The most successful entrepreneurs aren’t the smartest or best prepared. They’re the ones who start before they’re ready, learn faster than they fail, and refuse to quit on problems that matter.

Your next move isn’t to perfect your plan. It’s to take the first imperfect action toward solving a problem you can’t stop thinking about.

John Harthorne is the founder of MassChallenge and managing director of Two Lanterns Venture Capital. Learn more at 2L.vc.