I passed on a startup—and I’ve regretted the way I handled it ever since.

In diligence, we followed our process—opportunity, company, partnership. There were some concerns: a TAM that felt narrow, a valuation that felt rich. But if I’m honest, the real reason I couldn’t get to conviction was the founder.

I thought he was arrogant, and I worried his ego would cloud judgment and slow learning—fatal flaws for a first-time founder in an early-stage environment. I came to this conclusion because I’d introduced him to a couple of experts, hoping both to add value and to get a second read, but in the calls he barely engaged. Maybe he didn’t rate them. Maybe he was too far out of his depth to know what to ask. I didn’t know for sure. But I’d already made up my mind: this wasn’t a founder who would learn fast enough.

Here’s the part I regret.

When it came time to give feedback, I didn’t tell the truth. I pointed to the valuation and gestured vaguely at market size. And when he asked me directly—“Is that really why?”—I dodged. I didn’t say, “we don’t believe you’re the kind of founder who will evolve fast enough.” I didn’t offer specific examples. I wasn’t clear. I wasn’t kind.

And the irony? One of the reasons I passed was that I didn’t think he took feedback well. And then I denied him the very feedback I thought he needed. 

Why VCs struggle to give good feedback

The startup world loves to talk about feedback. Coachability. Openness. Growth mindset. Founders are told to “listen closely,” “stay curious,” and “take nothing personally.” They’re praised for vulnerability and punished for defensiveness.

And that all makes sense—if the feedback is specific, honest, and useful. Too often, it’s vague, sugar-coated, or just plain unhelpful.

Here are common “pass” phrases—and what they often mean:

• “Too early” – We don’t have conviction in you and/or this space.
• “Not enough traction” – We don’t get your GTM, or we’re not ready to back you.
• “Unclear differentiation” – We got bored and didn’t dig in.
• “We’re focused elsewhere” – Maybe true, maybe just a dodge.
• “Founder dynamics” – You made us uncomfortable, and we don’t know why”
  

Investors aren’t obligated to give feedback, and often we don’t. Sometimes the reason is valid: the company’s outside our mandate, or our views on the space are public. Sometimes we’re just moving fast.

But too often, we hedge because we’re not sure what we think—or we’re not ready to say it out loud. Saying “no” is easy. Explaining “why” takes time, clarity, and guts. It means confronting your own biases (“Was that a red flag, or just unfamiliar?”) and risking being misread or misquoted.

So we soften. We avoid. We move on.

And while we quietly guard our reputations, founders are left to interpret the fog.

They’re walking a tightrope: Be vulnerable, but not too raw. Be confident, but not cocky. Ask for feedback, but don’t push. Be open to learning, but only on the investor’s terms.

Because in this industry, even though no one wants to say it out loud, founder reputation isn’t just about what you build—it’s about vibes. Reputations travel fast, and they’re often shaped less by results than by how you make investors feel. Did you handle the pass with grace? Did you follow up, nod politely, integrate the feedback, and never make anyone uncomfortable?

Meanwhile, we as investors manage our reputations in private. We choose when and how to share a view. We backchannel. We preserve optionality. 

It’s not an equal exchange.

Why giving real feedback is worth it

The system doesn’t reward clarity—especially when you're saying no. But that doesn’t mean it isn’t valuable. In fact, I’ve come to believe that giving clear, honest feedback is one of the most underused tools we have as investors.

• It forces us to sharpen our thinking. To get to a real point of view—not just hedge until the market decides for us.
•  It shows us how a founder responds when things get uncomfortable—arguably a better test than any pitch.
• It builds trust, even in a “no,” and leaves the door open for the future.

And in rare cases, it makes the company better. And you create the chance to be more than a critic from the sidelines. You can be part of what made it work.

Feedback isn’t charity. It’s discipline. It’s craft. It’s the hard, human edge of doing this job well.

How I’m taking responsibility to do better

This isn’t a callout. I’ve failed at this. Most investors I respect have, too.

But if we say we value transparency, coachability, and strong founder relationships, we need to be honest about the signals we’re sending—and the systems we’re reinforcing.

Here’s what I’m trying to do better:

• Be clearer about the real reasons behind a “no”—especially when it’s about the team or founder dynamics, which are often the hardest to talk about and the most valuable to hear.
  
  
• Check my language when I catch myself softening or hedging—what am I actually trying to say, and who does my vagueness protect?
  
  
• Ask for permission before offering feedback, and respecting when a founder isn’t up for it.
  
  
• Interrogate my own bias, especially when something feels off but I can’t articulate why.

And most importantly, I’m working on not managing the founder’s emotions for them. That’s not my job. My job is to be honest, clear, and respectful—and trust that they can handle the truth, just like we expect them to handle every other hard thing that comes with building a company.

Feedback isn’t always comfortable, but it should be useful. And kindness doesn’t mean sparing someone discomfort—it means being brave enough to say the thing they might need to hear.

Clear is kind… and brave 

I think about that founder sometimes. I still believe he wasn’t the right fit for our firm. But I also know I didn’t give him a fair shot to grow. I told myself I passed because he didn’t take feedback well. But the truth is—I didn’t offer it well, either.

Clear is kind. But feedback is a muscle. So is courage. I’m still strengthening both.

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