Over the years, I’ve made a lot of investment decisions. Some were big wins. Others? Let’s just say they were lessons disguised as losses. But the more I’ve reflected on my journey as both an entrepreneur and investor, the more I realize how much psychology—more than spreadsheets or market trends—plays into success.

There’s no exact formula to getting investing “right.” Sure, due diligence, data, and strategy matter. But often, the real difference-makers are your mindset, instincts, and ability to hold steady when others are shaking. In my experience, intuition, grit, and timing are three of the most underrated tools in an investor’s toolkit.

Let’s talk about why they matter so much—and how you can strengthen each one.

Trusting Your Gut: The Power of Intuition

There’s a moment in every deal where numbers and projections take a back seat to a gut feeling. Do I believe in this founder? Does this product make sense for the market? Is there something here that data can’t fully explain but my instincts are pulling me toward?

I’ve learned to listen to that inner voice—especially when it’s built on years of exposure to brands, people, and patterns. Intuition isn’t just a “hunch.” It’s a quiet, cumulative knowledge built from experience. It kicks in when something feels off, or when something feels electric before the world catches on.

Some of the best investments I’ve made didn’t make total sense on paper. But I believed in the founder. I believed in the category. And I believed in the energy of the moment. That’s where intuition shows up. And the more deals you look at, the sharper your instincts become.

But a word of caution: don’t confuse intuition with impulse. Intuition is earned. Impulse is reactive. The best investors know the difference.

Grit Over Glamour: Playing the Long Game

A lot of people get into investing thinking it’s about the fast win—the big exit, the headline deal. But real investing takes grit. You have to weather the ups and downs, support founders through hard pivots, and sometimes wait years before seeing a return.

This is where mental resilience comes in. I’ve backed brands that took twice as long to scale as expected. I’ve watched founders grind through supply chain issues, funding gaps, and changing consumer trends. What kept us both in the game? Grit.

As an investor, your role is more than writing a check. It’s believing in the journey and showing up when things aren’t sexy. This isn’t Shark Tank. It’s real life. And real-life investing is about staying the course and encouraging your portfolio teams to do the same.

Founders feed off your energy. If you panic, they’ll panic. If you stay steady, it helps them stay focused. That’s the psychology of support—and it’s just as important as financial backing.

Timing is Everything (But You Can’t Force It)

Let’s be honest—timing plays a massive role in whether an investment hits or misses. The right product at the wrong time can flop. An average product at the perfect time can soar. And sometimes, it’s just about catching the right wave.

You can’t always control timing. But you can recognize trends, pay attention to shifts, and position yourself to move when the moment is right.

I’ve had success investing in wellness brands that launched just as health consciousness exploded. I’ve also seen promising startups struggle because they were ahead of their time or entered a saturated market too late.

The key is being present—reading consumer behavior, listening to what’s not being said, and being open to adjusting your thesis. Great investors are students of culture, not just balance sheets.

And sometimes, you have to be patient. Just because a category isn’t hot today doesn’t mean it won’t catch fire tomorrow. The art is knowing when to hold, when to push, and when to walk away.

Emotional Discipline: The X-Factor

Behind every good investor is emotional discipline. The ability to say “no” to shiny distractions. To sit on the sidelines when others are rushing in. To stay calm during market chaos.

Emotions drive markets more than most people want to admit. Fear, greed, hype—they’re always lurking. But successful investors know how to detach from the noise and stay grounded in their principles.

That doesn’t mean being emotionless. It means managing your reactions. Being aware of your biases. And knowing when your ego is making decisions instead of your logic.

This kind of self-awareness is what separates seasoned investors from gamblers.

The Human Side of Investing

At the end of the day, investing is about people. It’s about believing in someone’s vision and helping them bring it to life. It’s about relationships, trust, and shared ambition.

That’s why psychology matters so much. We’re not just betting on products—we’re betting on the people behind them. Their ability to lead, adapt, and grow. And our ability, as investors, to support, advise, and empower.

So yes, look at the numbers. Do the due diligence. But also trust your gut. Build your mental toughness. And study the moment. Because in this game, intuition, grit, and timing can make all the difference.