Right on Time: Lessons in Freedom, Risk, and Investing from Annie Evans

Reflections on angel investing, parenting, and the courage to choose freedom.

When I sat down with Annie Evans of Dream Ventures, I knew we’d talk about angel investing. What I didn’t expect was how much her story would stretch far beyond checks and cap tables into the territory of courage, trade-offs, and how we define wealth itself.

Annie Evans' path is not the straight line we so often imagine when we picture successful investors. She grew up around entrepreneurial parents who treated both wins and failures as something to celebrate. She moved to New York with big-city dreams, waitressed at the W Hotel, and spent her early paychecks on designer shoes (me too!). And she only really began saving and investing at age 38, when family planning shifted her priorities.

That part struck me. So often, the money narrative we hold up is “start early, be disciplined, never veer off course.” Annie’s story shows us another way: that joy, travel, adventure, and even missteps can be part of the journey. That starting “late” doesn’t mean you’re behind; it means you’re right on time for your life.

I remember feeling that myself. My first foray outside the stock market was into the secondary market, a turning point when I realized I could invest not just in abstract tickers, but in companies and products I actually used. In 2017, I wrote my first check into a private company, and I thought I was late to the game. Looking back now, I see I was right on time for my own path.

And then came my own bold “yes.” In 2018, I invested $20,000 into Substack pre-IPO. I had used the platform in the first company I founded, and when the chance to invest came, it felt like more than just a financial opportunity, it felt like a chance to participate in shaping the future of how voices get heard. That investment later doubled. But more than the return, what mattered was the alignment: backing something I believed in, something I knew firsthand could change the landscape.

That’s why Annie’s story about wiring her entire $10,000 bonus into iFundWomen resonated so strongly. On paper, maybe it wasn’t the “responsible” choice. But it gave her a seat at the table with 40 powerhouse women, and it became the catalyst for Dream Ventures. Sometimes the riskiest checks are the ones that define us, because they’re the ones that reflect not just our wallets, but our values.

Annie’s throughline is freedom, the freedom to choose family over a startup airline, to walk away from corporate life when severance opened the door, to invest in companies that reflect her values, to raise her son in a home where money, chores, saving, and even Bitcoin are dinner table topics.

I see echoes of that in my own life as a stepmom to three boys, ages 8, 11, and 13. With them, I love teaching not just about money, but about value and critical thinking, how not to get swept up in the hype, how to trust their own lived experience and judgment. Because wealth isn’t just what you earn or invest; it’s also the lens you develop to navigate a noisy world.

Listening to Annie, I kept circling back to one phrase she shared: “We rise by lifting others.” That’s her life mantra. And it’s evident in how she runs Dream Ventures, how she nurtures founders, and how she calls women into investing not just with their dollars but with their influence, connections, and belief.

I feel that same call in my own work. Annie has done an incredible job of adding visibility and capital to female founders, and I’m a big fan, and a grateful supporter, of the ripple effect she’s creating. Her mantra reminds me that every dollar, every introduction, every stage we hold open is a chance to lift someone else, and in doing so, lift ourselves too.

For me, this conversation was a reminder that wealth is not a fixed point, it’s a practice. Sometimes it looks like splurging on Louboutins at 24. Sometimes it looks like wiring your whole bonus into a risky bet because your gut says yes. Sometimes it looks like teaching your boys how to think critically about value before they even hit high school.

Mostly, it looks like choosing, again and again, to align your money with your values, and to make sure that freedom, not fear, is what’s guiding your hand.

Missed this conversation? Find it here (listen wherever you get your podcasts).