Redefining Wealth: Inclusive Investment Strategies with Kelly Ann Winget
If there’s one thing I want every founder to walk away with from this season of Finding Fearless, it’s this: wealth is not just for the privileged few. Wealth—real, lasting, generational wealth—is something we can all build when we stop playing by the rules that weren’t designed for us in the first place. And no one embodies this philosophy more than my guest this week, Kelly Ann Winget, the powerhouse behind Alternative Wealth Partners.
Kelly has done what few have—she’s raised nearly a billion dollars (yes, with a B) in private capital. But even more than that, she’s proving that the world of alternative investments doesn’t have to be an exclusive club for old-money elites. She’s opening the doors to new kinds of investors—women, queer folks, and people of color—who have historically been shut out of these conversations. If you’ve ever thought that private equity, venture capital, or big-money deals weren’t for people like you, this episode will change your mind.
One of the first things Kelly dismantles is the myth of what wealth actually looks like. We’ve been sold this idea that wealth means Lamborghinis, designer everything, and Instagram flexing. But Kelly knows better. The real wealth builders? They’re often quiet, unflashy, and investing in things that actually matter—businesses, infrastructure, and industries that will last for generations. She calls out a hard truth: most of us were raised without a real financial education. And that lack of confidence around money—how to make it, how to invest it, how to grow it—keeps so many talented, brilliant people stuck. It’s not about working harder; it’s about shifting how we think about money altogether. Kelly’s mission is to give more people access to wealth-building tools that have been gatekept for too long.
If there’s one thing Kelly and I could talk about all day, it’s the confidence gap that holds women back from stepping into their full power. She shared a moment that completely changed her trajectory—sitting in a room full of investors, moving around absurd amounts of money, and realizing: I am the smartest person in this room. That moment was a wake-up call. If she was the smartest one there, why was she waiting for someone else to give her permission to lead? This is where so many women get stuck. We second-guess ourselves. We think we need one more certification, one more degree, one more “I just need to learn a little more” moment. Meanwhile, men (with half the knowledge) are jumping in headfirst, making deals, and getting the backing to build their businesses. Kelly’s advice? Stop waiting. Take up space. Move with the confidence of the mediocre men who get funded every single day.
At Fearless Foundry, we say this all the time: entrepreneurship is one of the greatest tools for equity. And Kelly makes this case better than anyone. So many of us are taught that the only way to build wealth is through real estate. And sure, real estate has been a powerful vehicle for many. But the real wealth-building families? They didn’t make their money flipping houses. They built industries. They owned businesses. And owning a business—not just working in one—is what changes the financial future of your family for generations.
But here’s the best part: it doesn’t have to be a “sexy” business. HVAC companies, plumbing, bookkeeping firms—these businesses print money. Kelly sees a massive opportunity for young entrepreneurs to buy out older business owners who don’t have succession plans. You don’t need a tech startup to build a financial empire—you need a profitable, scalable business with real demand.
Kelly breaks it down simply: you don’t need millions to start investing. You can start with:
• Angel investing—Pooling funds with friends to support startups or local businesses
• Small business acquisition—Buying into a stable, existing business
• Alternative investments—Exploring funds like Kelly’s that allow smaller investors to get a seat at the table
And if this whole world of investing still feels overwhelming? Start by getting educated. Kelly wrote Pitch the Bitch to help close the knowledge gap and make wealth-building accessible, not intimidating.
Here’s what I hope you take away from this conversation with Kelly: No one is going to give you permission to build wealth. You have to decide that you’re worthy of it. That means:
• Charging what you’re worth
• Getting comfortable with big money conversations
• Understanding that owning a business—not just working in one—is the fastest track to generational wealth
This episode left me fired up, and I know it will do the same for you. If you’re ready to shift your mindset and start playing a bigger game, go listen now. And if you want to start learning about money on your own terms, grab Kelly’s book.
The world of wealth is changing. Let’s make sure we’re part of that change.
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