Managing Risk Is the New Competitive Advantage

Back in 2020, I made a decision that felt like a big risk at the time. But now with the benefit of hindsight, not only did the move make sense, it changed the trajectory of my journey for the better.

At the time, I was two years into a role as Partner and Managing Director in a firm helping athletes navigate the investment world. In addition, I was advising startup founders and investing in early-stage companies. It felt like I was finally turning the corner on the brand and positioning I’d been building toward for years.

Then the world shifted.

COVID forced all of us to re-evaluate. I had to balance my two young kids transitioning to learning from home with the companies that needed leadership. I quickly came to the realization that I couldn’t do both at the level I was accustomed to. I had to make a choice: continue grinding in an industry where I had spent a decade building my reputation, or step back and prioritize what mattered most.

In choosing to prioritize home, I also made the decision to resign from my role at the athlete investment firm. I divested my equity there and walked away many of the other positions I held in the venture capital world. It wasn’t just leaving a role. It was also walking away from 10 years positioning myself as a relevant player in the industry.

It felt like a risk—but sometimes, you have to jump anyway.

As I evaluated what was next, I decided to step into finance from an entirely new perspective—as a financial advisor. Logically, this seemed like a good fit since I could support athletes from within their personal ecosystem instead of as an outside entity.

But in reality, I was starting from scratch. It meant studying for my Series 66 and Series 7 exams from home, by myself, while balancing home life. Diving into a completely new industry with very few resources to lean on made me feel like the rookie in the room again.

Playing It Safe is the Real Risk

Too many people let fear of change keep them stagnant. They stay in careers that no longer challenge them, industries that are evolving without them, and mindsets that no longer serve them.

The real risk isn’t failing. It’s staying where you are while the world moves forward without you.

Here’s the problem with getting too comfortable: the economy in 2025 doesn’t reward comfort—it rewards adaptability.

In other words, stagnation is a fast track to irrelevance. The industries moving the fastest—tech, finance, entrepreneurship—reward people who lean into change, not those who resist it.

The reality of facing risk is that your actions at critical inflection points commit you to a trajectory—either adapting to stay ahead or choosing comfort and falling behind.

Which path are your actions choosing for you?

Using Risk to Your Advantage

Risk isn’t about gambling your future—it’s about putting yourself in position for new opportunities. The most successful people don’t avoid risk. They manage it.

The people who win at the highest level today understand that embracing risk isn't just advisable—it's essential. They aren’t just working harder, they’re thinking bigger, taking calculated bets that force them to grow. They expand into opportunities while others hesitate—that’s how they separate from the pack.

The difference between reckless risk and strategic risk? Preparation.

• Successful people make bold moves, but they also study the game before they play.

• They understand their strengths and position themselves in spaces where those strengths create competitive advantages.

• They don’t wait for the perfect time—because the perfect time doesn’t exist.

Rewiring Your Mindset

If risk makes you uncomfortable, you’re not alone. But the key to meaningful growth is learning how to get comfortable being uncomfortable.

Most people think about risk from a financial perspective first. But it’s just as relevant to your business and career choices. Companies that manage risk effectively outlast and differentiate themselves from the competition—so how do you build that muscle in your career?

• Shift your perspective on failure. Most people see failure as an endpoint. High performers see it as part of the feedback loop. If you learn from it, failure isn’t a setback—it’s a data point.

• Take smaller risks first. Before making a big career pivot, start with smaller calculated bets—new projects, new roles, side ventures. Build confidence in making bold decisions.

• Surround yourself with risk-takers. Your environment shapes you. If you spend time around people who embrace risk, it starts to feel normal. If you spend time around people who fear it, you’ll start second-guessing yourself.

Taking Strategic Risks

The key to strategic risk is knowing how to self-scout to assess where you are, identify the gaps, and position yourself accordingly.

1. Assess Your Strengths. What do you do better than most? Where can that be applied in new industries or roles?

2. Analyze the Market. Where is there demand that aligns with your skills? Where are opportunities emerging?

3. Stack Small Wins. Instead of making a blind leap, build momentum. Start with a side project, take a short-term contract, or upskill in a new area.

Closing Thoughts

For me, the bet I made back in 2020 is paying off in 2025. The insights I learned as a financial advisor—about equity markets, alternative investments, and portfolio construction—became the foundation for the investment firm I launched last year. The ability to synthesize them alongside the 10 years I spent in venture capital have provided a unique lens that allows me to leads strategy at CVP as we grow a first-of-its-kind firm in sports.

At the end of the day, change is inevitable, but uncomfortable. But discomfort is the price of growth. The sooner you embrace short term discomfort, the sooner you can position yourself to win for the long haul.

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