“Propose on the First Date” and Other Crazy Relationship Advice That (Surprisingly?) Worked + What this newsletter is all about
Let’s Start With a Confession
I once proposed to a woman within an hour of meeting her. That woman is now my wife.
Was it sheer desperation? A mad social experiment? Nope.
It was just me, your friendly neighborhood serial entrepreneur, creating an all-time great “founder pitch”—except the “startup” was my future marriage.
And guess what? It worked.
In a recent interview on the Modern Relationships podcast, my wife Rie and I laid bare the earliest days of our relationship.
We talked about:
Why she thought I was an angel investor and gave me a 30-second startup pitch…
How I was actually looking for a date (thanks, friend-with-the-cute-single-friends!).
The moment I blurted out, “I’ll marry you,” as if I were ordering dessert.
How my wife and I maintain a true 50/50 relationship - but also why so many couples sabotage themselves seeking this type of “perfect equality.”
I’m about to give you the spiciest stories from that conversation—just enough to tease you into checking out the full conversation (where the real bombs get dropped). So buckle up and keep the children at bay.
Wait, Who Is This Guy?
For those who subscribed because of a recommendation or don’t remember me - hi, I’m Adam. I’m a serial founder who built and sold a bunch of companies (bootstrapped and venture backed), lived nomadically for 5 years, predicted how COVID would unfold, and went pretty deep in Vipassana meditation and neuroscience. I’m married to fellow repeat founder Rie Yano, with whom I have two lovely kids (2, 7).
In recent years I’ve been laser-focused on longevity—as in, solving aging and death so we can live in great health as long as we like. I’ve been angel investing in the category for a few years now (companies such as NOVOS, Loyal, Fitnescity, Immunage and more) and recently co-founded Vitalism to advance anti-aging science at humanity-level scale. We are holding a huge event called Vitalist Bay in California in a couple of months.
What motivates me most is the desire to answer the big mysteries of existence; what is the true nature of reality? why are we here? what does it mean to be human? (check out this cool video about just that)
In the meanwhile, I try to push the envelope on how to do life, from first-principles.
So if you stick around, you’ll see me talk about everything from relationship hacks to biotech breakthroughs and investing. Expect startup war stories, geopolitical analysis, global adventures with two kids, homeschooling, and the latest in longevity research and applications.
In short: the goal is to expand the possibilities of human life—and make it a lot more fun along the way.
The Reluctant Pitch Turned Marriage Proposal
“I could be Roger,” I said, stepping into a bar on a Monday night in Chelsea, NYC. And that, dear friends, became the single weirdest opening line of my life.
Rie thought she was meeting an investor named Roger. I was definitely not Roger. But I was sufficiently smitten (read: drooling) to go along with the confusion. One thing led to another, and a few hours later, I was telling her I’d marry her if that was what it took to keep her from getting deported.
Was it logical? Probably not.
Did Rie think I was trying to get into her pants? Absolutely.
But it was the boldest pivot I’ve ever attempted, and for once, it wasn’t about startup valuations—it was about snagging the best co-founder I could imagine for life.
“Work on Your Relationship”? We Kinda Disagree
Most relationship gurus say: “Relationships are work—compromise, therapy, rinse, repeat.”
We say: “Heck, no.” If a relationship demands hammering and chiseling from day one, you’re forcing a shape that probably doesn’t fit.
We’re not talking about zero friction, because conflict is as inevitable as your college roommate eating your leftovers. But at the core, we believe if you find a truly aligned partner “product-market fit,”, the big stuff clicks smoothly, and doesn’t devolve into daily emotional warfare.
We’re also not naive. Sometimes, yes, real couples do real relationship push-ups; but the baseline shouldn’t be a never-ending Ironman Triathlon.
Our 50/50 Approach to (Almost) Everything
Q: “Should we literally schedule who changes the diaper at 2:47 PM?”
A: “Yes.”
Rie and I are committed to fairness, calendaring ownership time with the different parts of our life responsibilities: who’s on kid duty, who’s getting a sabbatical day, and who’s cleaning up the fallout in the kitchen.
Why do we do this?
We’re both care about efficiency
We deeply value equal freedom and responsibility.
Perhaps ironically, by systematizing the mundane, we free up room for those lightning-bolt romantic escapades and weird, improvised date nights.
Our “Co-Locating” Love Story
No conversation about us is complete without a nod to our bizarre pre-moving-in routine:
I asked Rie to keep her Skype on 24/7 (this was pre-zoom) for days so we could “co-locate.”
She thought it was anxiety provoking to be “watched” hahaha.
But it gave me a real-time window into her world—and her into mine. (Ever wonder if your new love interest can actually see those spinach bits between your teeth over Zoom? Answer: They can.)
Sometimes building a relationship is just about clocking in the hours.
There’s More Where That Came From
If you’re thinking, “Wait, you actually proposed on the first night? And the lemon-water meltdown in your marriage is a real fight story? And you believe relationships are an effortless synergy?”—well, that’s just the half of it. Literally.
Chek out our full Modern Relationships interview for:
The best (and worst) secrets we gleaned from friends’ disastrous divorces
Why we left NYC and hopped countries for 5 years
Our “co-founder” approach to marriage—the lines between romance and boardrooms really blur sometimes…
→ Check out the full podcast or YouTube episode ← (Go on, you know you want the uncut version.) Or get it as a podcast on Apple or Spotify.
What else would you like me to write about?
I plan to keep dropping stories from the intersection of longevity, AI, startups, software, and insane relationship experiments. But I want to hear from you.
Drop a comment below or hit me up with your hottest takes. Let’s keep this conversation very real, very weird, and mostly helpful!
Until next time—remember that finding that great relationship may be a big challenge, but the returns are even bigger.
And if it’s meant to be, well… you might just find yourself spontaneously offering to marry someone at a bar on a Monday night.
– Adam
P.S. If you liked (or hated) this post, share it with a friend or foe and let them weigh in. I’m always game for a debate, especially if it involves sour lemonade.
Well done, Adam!! You are a true and daring entrepreneur!! Looking forward to more!