Skin in the Game

Fearless Girl

When I worked at a hedge fund, pitching investment ideas to my boss was an adrenaline rush. I’d research a company, prepare my case, and present it with all the energy I could muster. My boss would push back, challenge my assumptions, and question my numbers. Then I’d go back, refine, and follow up—until eventually, he might give me the green light to buy the stock.

Even though I wasn’t the portfolio manager, I still had skin in the game. If my idea worked, the firm made money, and so did I. If it didn’t, I felt it. That accountability sharpened me.

But here’s the irony: once you have your own money, it’s easy to get… lazy. When you’re not pitching to someone else, when there’s no outside scrutiny, you risk losing that edge.

So how do I fight that?

Lessons from Venture Capital

I borrow from what I’ve seen venture capitalists demand. Entrepreneurs pitching for funding don’t get the luxury of “good intentions.” They need evidence—a minimum viable product, a customer base, real traction.

The best way to break in is by shipping. Build something real. Let customers use it, talk about it, and validate it. That track record is what opens doors. It’s proof of execution.

And it’s not about charisma—it’s about being compelling. A founder’s conviction in their product, their market, and their customer is what draws investors in.

But What About Knowledge Workers?

Most of us aren’t building rockets or bagel brands. We’re knowledge workers—financial advisors, consultants, marketers, storytellers. We don’t ship physical products.

But we still need an MVP.

For me, that means content.

• I’m working on a book for strivers in their second half of life.

• I’m designing a financial education course for young women, helping them see that they are already part of the money game—and the sooner they learn the rules, the stronger their position.

These projects are my MVPs. They are my way of shipping.

Pitch Yourself First

The hardest person you’ll ever pitch is yourself. That’s why I sit down and write investment memos for my own ideas. What do I want to build? Why does it matter? What do I hope to achieve?

Henry Ford said:

“Whether you think you can, or you think you can’t—you’re right.”

That quote unblocked me five years ago when I started my business.

And it still drives me today.

So right now, I’m putting together an investment memo for myself.

It’s my vision board, but sharper, clearer, and backed by numbers.

And soon, I’ll pitch it to my forum group for accountability.

Because whether you’re raising money from others—or funding your own dreams—you’ve got to prove, first to yourself, that you’re worth betting on.

✨ What about you? If you had to pitch yourself today, what would your investment memo say?

Tiffany Kent

Your Friendly Wealth Engagement Guide

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