At a VC dinner a few weeks ago, one of my closest and oldest VC friends (even though she’s MUCH younger & smarter than me) told the room about the first time we met. She laughed as she recalled how I compared the relationship between an early-stage investor and a first-time founder to your first high school relationship.
At first, the room chuckled. But the more we unpacked it, the more it resonated. Because let’s be honest—first-time founders and early-stage investors go through the same emotional rollercoaster as two teenagers navigating their first serious relationship.
We start with the courtship, aka, the pitch process. Remember the nerves before asking someone out in high school? The overanalyzing, the rehearsed lines, the silent hope that they’d say yes? That’s a first-time founder walking into their first VC pitch.
The founder is trying to say all the right things, put their best foot forward, and prove they’re worth the commitment. Meanwhile, the investor is sizing them up—do they have potential? Do they have staying power? Do they seem like someone they’d want to be in a long-term relationship with?
And just like in high school, sometimes the biggest mistake is trying too hard to be what you think the other person wants instead of just being yourself.
We enter the honeymoon phase – once the investor commits, it’s all excitement. The founder feels validated, the investor feels like they got in early on something special, and both sides are optimistic about the future.
During this phase, everything is going right. Revenue is up! Growth is happening! The founder is sending updates full of good news!
Just like that high school relationship where you’re convinced, this is it.
Life is not all roses –reality sets in. Things start to get hard. Customers push back, product issues arise, hiring is tough, and revenue projections miss the mark. Suddenly, the investor—who was all praise a few months ago—has questions.
What’s the plan? Why isn’t growth faster? Do you need to make some tough calls?
It’s like the first big fight in a high school relationship. Do you communicate and work through it? Or do you start to resent each other?
Every successful relationship is built on trust and communication. If the only updates an investor gets are when things are going great—or worse, if the founder ghosts them when things go wrong—trust erodes.
It’s like in high school for the digital native generation (note passing for others) when someone just stops texting back. You’re left wondering, Did I say something wrong? Are they okay? Should I reach out, or do I wait for them?
The best founders, like the best partners, keep the lines of communication open—especially when things aren’t perfect.
But even when things go well, relationships drift.
Just like in high school, where you and your first love swear you’ll always stay close—but then college happens, new experiences happen, and life pulls you in different directions—the same thing happens with founders and early-stage investors.
A few years in, the founder raises their Series A, and the new investors take center stage. The founder’s priorities shift, they have a bigger team, bigger challenges, and bigger expectations. The seed investor, who once got every update and every late-night call, now gets a quarterly email and the occasional “Hope you’re doing well!” text.
It’s not personal. It’s just life.
And eventually, as the company scales, that once all-consuming founder-investor relationship fades into a distant memory—one you both look back on fondly but know was just a chapter in a much longer story.
At the same time, not every relationship works out nor is every company successful. Sometimes, an investor who seemed great at the start turns out not to be the right fit. Sometimes, a founder pivots in a direction that makes sense for the business but not for the investor. And sometimes, external forces—competition, market downturns, bad timing—force a breakup.
And like a high school breakup, some end amicably, and others… not so much. The best ones end with mutual respect, keeping the door open for future opportunities. The worst ones leave baggage that follows you for years.
Every investor has the one that got away—the company they could have backed but didn’t. And every founder has the investor they should have chosen but didn’t.
At the end of the day, the best founder-investor relationships—like the best high school relationships—are built on honesty, mutual respect, and the ability to grow together.
Some will last, some won’t, but all of them teach you something for the next one.
Next time, we’ll dive into the first date—aka the pitch meeting. Because just like in high school, getting the first meeting is one thing. Nailing it? That’s a whole different challenge.