One night biking through the coast of Manhattan, I noticed a subtle pattern – the same dynamics that had played out in my last relationship were mirror images of what I was experiencing as a founder. Here are some parallels that I see in the two seemingly disconnected worlds.
1. Timing Is Everything (In Love and Fundraising)
The best time to fundraise is when you don’t need to.
Sound familiar? It’s the same cruel irony of dating: you’re most attractive when you’re not desperately seeking validation. VCs don’t want to rescue a sinking ship any more than someone wants to be your emotional life raft.
When our startup was thriving, investors were sliding into our DMs. When we actually needed capital? Radio silence. Just like in relationships, desperation has a smell, and it repels the very people you’re trying to attract. No matter how strong you are, you can’t jump from one relationship to another without healing the wounds from the past.
The lesson? Build from a position of abundance, not scarcity. Whether it’s raising money or finding love, confidence born from genuine options always wins.
2. Product vs. Distribution: The First Love Syndrome
First-time founders obsess over the product. Second-time founders obsess over distribution.
I learned this the hard way. When users told us our product didn’t add value, we did what any logical (first-time) founder would do – we disappeared into our development cave for six months to “fix” everything.
We emerged like proud parents with our beautiful, redesigned baby, only to discover we still had the same handful of lukewarm users. Meanwhile, a competitor with an arguably worse product had eaten our lunch simply because they understood something we didn’t: distribution beats perfection.
We had been trying to solve a distribution problem with a product solution. It’s like spending all your energy becoming the “perfect” partner while never learning how to actually connect with people.
This mirrors first love perfectly. The first time you fall, you give everything: no strategy, no self-preservation, just pure, reckless intensity. But the second time? You know what you’re looking for. You understand that compatibility matters more than chemistry, that sustainable connection beats passionate chaos.
The irony is that this wisdom can sometimes make you too calculated, letting logic overpower those magical moments that make relationships worth having in the first place.
3. The Pivot vs. The Ring
Here’s where startups and relationships diverge beautifully:
In startups, when you’ve tried everything and you’re still stuck at rock bottom, the answer is clear: pivot. Learn from your mistakes and iterate on the problem.
But relationships? That’s different. If you find someone who stays when they have every reason to leave, who sticks with you at your lowest point — look up at the sky and be grateful. You’ve found the finger for the ring.
Of course, this only works when both people are complete and secure in themselves. Codependency isn’t romance; it’s just two people drowning together.
4. The Only Answer That Matters
In relationships, you’ll inevitably face these questions:
“What if you meet someone smarter?”
“What if there’s someone more compatible?”
“Why would you stay with me?”
There’s only one answer that carries you through: “Because you’re mine. No matter who comes along, they’ll never be the one I committed to.”
In startups, the questions sound different but feel the same:
“What if this doesn’t work?”
“What if we can’t build what we envisioned?”
The founder’s version of that answer: “We’ll make it work. If we can’t, we’ll learn from the failure and pivot. We’re founders – we fall in love with problems, even when our solutions don’t work.”
5. Trust Your Gut (Before It’s Too Late)
If you have that feeling in your stomach that something’s off, trust it. Your mind can stitch the facts together later, but your intuition is processing signals your conscious brain hasn’t caught up to yet.
It’s easy to ignore gut feelings when overwhelmed by the intoxication of being in love. By the time those instincts demand attention, it can feel too late. Often, the signs were visible all along; they just weren’t ready to be acknowledged.
The same applies to startups. That nagging feeling that your target market isn’t responding the way you hoped, that your unit economics don’t quite add up — pay attention to those whispers before they become screams.
The Beautiful Mess of Being Human
Here’s the truth: If you’ve never failed at a startup, never had your heart broken, never made a mistake that taught you something essential about yourself, you’re not experienced, you’re just lucky. And luck runs out.
If you built a unicorn on your first try or married your first love without ever fighting, congratulations — you’re the human equivalent of a ChatGPT wrapper: technically impressive but missing the messy wisdom that comes from actually living.
But if you’ve messed up, learned from it, and grown in the process? Welcome to the club. You’re beautifully, imperfectly human and that’s exactly what makes you capable of building something real.
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