5 Risk-Taking Lessons From Founders Who Bet Big and Won

Playing it safe in business? That’s exactly why you’re stuck. The harsh reality is that the biggest wins in entrepreneurship come from bold, audacious bets — the kind of decisions that make most people sweat and question your sanity. It’s not about recklessness; it’s about having the courage to step outside the norm, seize opportunities others overlook and embrace the uncertainty that comes with pursuing greatness.

The difference between merely surviving and truly thriving isn’t in doing what’s expected but in taking calculated risks that redefine the rules and change the game entirely.

Related: You Have to Take Risks to Succeed. Here Are 4 Risk-Taking Benefits in Entrepreneurship

1. Elon Musk: Go all in (even when it’s crazy)

Risk: Elon Musk famously poured his entire PayPal fortune into his next ventures — SpaceX and Tesla — leaving himself nearly broke.

In 2008, both companies were on the brink of collapse. Tesla’s production delays and SpaceX’s failed launches nearly bankrupted Musk. Instead of cutting his losses, he doubled down, betting everything on one more launch for SpaceX. That launch was successful, securing a $1.6 billion NASA contract and saving both companies.

The lesson: Most entrepreneurs hedge their bets to avoid failure. Musk’s story shows that sometimes, the only way to win big is to go all in. The difference between success and failure often comes down to sheer determination and risking it all for the vision you believe in.

2. Sara Blakely: Bet on yourself (when no one else will)

Risk: Sara Blakely, the founder of Spanx, had zero experience in fashion or business. She took her entire life savings — $5,000 — and invested it into her crazy idea for footless pantyhose.

Blakely was rejected by every hosiery manufacturer she approached. Instead of giving up, she hand-sewed her first prototypes and hustled to get her product into Neiman Marcus. That risk paid off. Spanx became a billion-dollar brand, and Blakely became the youngest female self-made billionaire.

The lesson: No one is going to believe in your idea as much as you do. Waiting for someone else to validate your vision is a surefire way to fail. Betting on yourself means pushing forward when the odds are stacked against you.

Related: (Podcast) Barbara Corcoran Reveals How to Not Be Afraid of Taking Risks

3. Jeff Bezos: Keep reinvesting (even when you’re profitable)

Risk: In Amazon’s early days, Jeff Bezos took all of the company’s profits and reinvested them into growth.

At a time when competitors were cashing out, Bezos took massive risks by building infrastructure and expanding Amazon into new markets, often at a loss. That relentless focus on reinvestment is why Amazon went from a bookstore to one of the largest companies in the world, dominating cloud computing, logistics and retail.

The lesson: Short-term wins won’t build a legacy. If you’re playing it safe by pocketing profits and holding back on growth, you’ll fall behind. Entrepreneurs who win big take the long view — and are willing to sacrifice short-term comfort for long-term dominance.

4. Richard Branson: Embrace the risk culture (even when it fails)

Risk: Richard Branson’s Virgin brand is synonymous with risk. He launched Virgin Records, Virgin Atlantic and even Virgin Galactic — a space tourism company. Not all of his ventures succeeded. Virgin Cola, Virgin Brides and Virgin Cars all failed spectacularly.

But Branson’s “risk culture” is what makes him one of the most successful entrepreneurs in the world. He views failure as a necessary step to innovation. By embracing risk, he’s built a multi-billion-dollar empire spanning industries.

The lesson: Failure isn’t fatal — but playing it safe is. The only way to innovate is to take risks, even when there’s a chance of failure. If you’re not failing occasionally, you’re not taking big enough risks.

Related: Richard Branson on the Importance of Taking Meaningful Risks

5. Howard Schultz: Double down on expansion (even when everyone says stop)

Risk: Howard Schultz took Starbucks from a small Seattle coffee chain to a global powerhouse by betting big on expansion.

During the 2008 financial crisis, while most companies were scaling back, Schultz doubled down on Starbucks’ global growth, investing in new stores, technology and customer experience. His risk paid off. Starbucks came out of the recession stronger, more profitable and more innovative than ever before.

The lesson: When everyone else is retreating, the boldest move is to advance. History shows that some of the most successful entrepreneurs made their mark by leaning into uncertainty when others hesitated. By taking calculated risks during tough times, they positioned themselves to seize opportunities, innovate and build resilience.

If you’re playing it safe, you’re playing to lose. The greatest entrepreneurs in history didn’t get there by avoiding risk — they bet big on their visions, doubled down during tough times and weren’t afraid to fail. The question isn’t whether you’ll face risk in your business. The question is: Will you be bold enough to take the kind of risks that lead to life-changing rewards? After all, the biggest breakthroughs often come from the biggest leaps of faith.