I’ve spent the last decade evaluating long-term relationships through my work as a venture capitalist, investing in startups and founders. Now, as I step back into dating for the first time since I was 21, I’m struck by how much the venture capital mindset applies to modern relationships. However, just as I had to learn in venture capital, it’s easy to ignore lessons learned and convince myself that “this time will be different.” These are the 5 venture capital lessons I most want to remember as I play the dating game.
1. Shoot for the Moon
When I first started investing, I made a series of “safe bets.” They were unlikely to yield 100x returns, but they were on a clear path to produce singles and doubles. And…most of those companies still failed. A whopping 75% of venture-backed startups fail. And about 60% of second marriages end in divorce. Building startups and relationships (especially later in life) is HARD. There are no safe bets.
So, if I settle for something that seems safe, I will likely fail anyway and I will almost certainly be bored long before that happens. When I allow myself to unapologetically pursue the best possible outcome—instead of settling or hedging—unexpected opportunities open up. Some of the most “unrealistic” outcomes have become reality when I’ve raised my standards and stayed aligned with them.
2. Flexibility Creates Opportunity
Every investor starts with a mental model of the “ideal” company. And almost every great investment breaks that mold. The same applies to relationships. After my divorce, I created a list of 47 qualities I wanted to find in a man. So far, the man I’ve had the most meaningful relationship with since then had only about seven of the items on that list!
My mentor and friend Mikela Tarlow found a similar experience, which she shared in one of our podcast episodes, “When Life and Love Don’t Have to Be Hard.” It was only when she let go of her rigid idea of the “perfect man” that she was able to find real love.
Some of my best investments—and best connections—have come from situations that didn’t fit my original criteria.
3. See Enough Deal Flow (Yes, Even in Dating)
Early in my career, my worst investments were the ones I made too quickly, without enough exposure or comparison. It wasn’t until I met at least 30 entrepreneurs that I was able to distinguish the good from the extraordinary.
Dating works the same way. You have to “kiss a lot of frogs” to find your prince.
4. Be Open to Creative Structures
Not every successful company—or relationship—looks traditional.
I’ve seen thriving couples design unconventional but deeply fulfilling arrangements: partners living in adjacent homes, ethical non-monogamous relationships that meet everyone’s needs, etc.
The takeaway? There’s no single blueprint for success. The best structure is the one that actually works for the people in it.
5. Trust Your Intuition
One of my seemingly best investments failed about 18 months in. Both the opportunity and the entrepreneur looked perfect on paper, but I just had this feeling she wasn’t going to go the distance. I had no evidence to back up my hunch so I invested anyway—and 18 months later she gave up and shuttered her business.
Every time I’ve ignored my gut feelings, I’ve regretted it.
The same goes for dating.
Chemistry, alignment, and intuition—these are all critical data points. If something doesn’t feel right, it usually isn’t.
Final Thought
Whether in venture capital or relationships, success comes from a mix of strategy, openness, and instinct.
The frameworks may be different—but the patterns are surprisingly similar.
What’s a lesson from your career that has shaped how you approach your love life?
