Fundraising Mistakes I Only Realized After Switching to the VC Side

I raised $3M+ as a YC founder. I thought I knew how fundraising worked.

Then I switched sides. Became a venture lead. Reviewed 8,000+ startup applications. Did 500+ investor calls. Helped 100+ founders raise over $100M.

Sitting on the other side, I realized many of the things I did right were actually wrong.

And I watched hundreds of founders make the exact same ones without knowing it.

This is Part I: mistakes founders make before the first investor call. Part II covers what happens during and after.

1. Every VC Call Is a Pitch. Even the Ones You Think Aren't.

Founder side: I used to take investor calls even when I wasn't raising. Inbounds, warm intros, "just building relationships." I'd share a pitch deck thinking it was casual.

It's not casual. It's an audition.

VC side: The moment you hop on a call and share your deck, they're evaluating you. Taking notes. Forming an opinion. And that opinion gets filed in the CRM. When you come back six months later actually raising, they're not starting fresh. They're starting from "last time wasn't convincing."

What to do instead: If you're not in fundraising mode, don't take dedicated investor calls. Chill conversations at events are fine. But a 30-minute call with a deck is a pitch whether you call it one or not. Share the trailer, not the rough cut. Save your full version for when you're ready to close.

2. A Successful Fundraise Is a Sprint. Not a Marathon.

Founder side: When I started raising, I didn't go all in. Taking calls here and there while still building product, shipping features, handling customers. Nothing was compressed. I see founders do this constantly. They spread their raise over months.

VC side: The majority of investors are FOMO-driven. When a VC asks "who else are you talking to?" and the answer isn't "a few dozen investors this week," there's no urgency. No urgency means no FOMO. No FOMO means their default is to wait. And waiting is a soft no.

Worse, if they realize you've been raising for three months without momentum, it kills the hype. "I actually like these guys, but why has nobody else believed in them?" That question will come up in their partner meeting. And it's nearly impossible to recover from.

What to do instead: When you pull the trigger, go all in. Two to three weeks. All intros fired at once. Back-to-back calls. Treat fundraising as the only job. Then get back to building.

3. More Intros Won't Save Your Raise. The Right Ones Will.

Founder side: Many founders, especially first-timers, struggle to build a wide top of funnel. So they default to the easiest options: super connectors, "intro" brokers, investor email groups. I did the same. Shared my deck with every "send me your deck, I know some people" contact. More distribution, more chances. Right?

VC side: Most VCs subscribe to every deal-sharing channel to see more startups. But they mentally rank those sources. Some channels mean "read immediately." Others mean "skim subject line and archive." Your startup might be incredible. But if it arrived through the wrong door, you're downgraded before they even open slide one.

What to do instead: You need a wide top of funnel, but how you build it matters more than how big it is. Lean on warm intros from people who genuinely know you, to specific investors. Avoid the super connectors who share deals wholesale. You want volume, but you also want every investor to feel like getting access to you took effort.

4. Don't Let Investors Decide on Your Company Before the First Call.

Founder side: I've seen founders spend weeks on their deck. Hiring designers, perfecting slide layouts, building a 30-page appendix. Meanwhile the blurb they send with warm intros gets five minutes of thought. Copy-pasted from their 'About' page. And then they share both when asking for a warm intro.

VC side: When a blurb arrives with a deck attached, the deck gets opened first. A deck provides an executive summary of your entire company and triggers the "should I invest?" mindset. They're allocating 60 seconds to answer that question. That's a brutal bar to pass.

A warm intro with just a strong blurb triggers a completely different mindset: "I have questions but this looks promising. Should I allocate 30 minutes to learn more?" That's a much easier bar to pass.

What to do instead: Send the blurb to get warm intros. Not the deck. Spend real time making your blurb hooky and curiosity-driven. The goal is "I need 30 minutes with this founder." Save the deck for after the call is booked.

5. Cold DMs Don't Sell Your Startup. They Sell Desperation.

Founder side: When warm intros dry up, the temptation is to go direct. Template messages to investors. "Hey {{First_Name}}, we're building X and I'd love to chat." Even if it converts 1%, send 1,000 and you get 10 meetings. Better than nothing.

VC side: A templated cold DM signals massive desperation. It reads as "I don't have a network strong enough to get a warm intro." Instant pass.

But the real damage is hidden. If you later get a warm intro to that same investor, they'll search your name and find the old cold DM. Now that warm intro doesn't feel warm anymore. You start with negative points before the conversation begins.

What to do instead: Only cold DM if it's a genuine, specific match. Reply to something they actually posted. Drive a real conversation before ever mentioning your startup. Yes, it's painfully unscalable. That's the point.

6. Talk to Your Dream Investor Last. Not First.

Founder side: Once you have a hot startup, dream VCs will reach out or you'll get warm intros. And the moment they do, every instinct says jump on the call immediately. I did this. Scheduled a call for the next day to show how responsive I was. I wasted my best shot on my worst day.

VC side: Arranging a call for tomorrow signals nobody else is competing for your time. That's not responsiveness. That's low demand. They'll hear your unpolished pitch, spot weaknesses you haven't patched, then ask "who else is in?" You'll say "we just started." No urgency. No FOMO. Deal killed.

What to do instead: Keep your dream investors in the waitlist while you sharpen your pitch with angels and smaller funds. Learn the common tough questions. Improve your answers. Collect some early checks and build momentum. Then go to the lead. "We're 60% committed." Now they see a train leaving the station.

7. Raise to Hit a Milestone. Not to Have Money in the Bank.

Founder side: Most founders pick their round size by looking at what other companies at their stage are raising. "$2M at $20M" because that's what everyone does. Never working backward from what they actually need and the specific milestone they need to hit. Just a number that sounds right and feels safe.

VC side: Your round size tells us whether you understand your business. "$2M at $20M" with no solid justification? It's obvious you copied it. The founders who stood out could trace every dollar to a decision. "We need $3M to hit 500 paying customers in 18 months, which sets up our Series A. Here's how every dollar gets there..."

What to do instead: Start with the milestone that makes you next-round ready. Then map out how you get there. What do you need to build? Who do you need to hire? What does it cost to run for 18 months? You don't need a five-year financial model but you need enough math to show this isn't a number you copied. It's a number you projected.

8. The Best Way to Close a Round Is Knowing You'll Survive Without It.

Founder side: Most founders go into fundraising with one plan. Raise X at Y. That's it. No backup. No survival plan if the raise goes badly. When offers come in below expectations or with bad terms, they panic. Worse, confidence erodes with every "no".

VC side: If your raise isn't going well and you have no backup plan, VCs can smell it. Your tone changes. Your urgency shifts from confidence to survival. The strongest founders, on the other side, are the ones who can confidently walk away. VCs sense that too. That kind of composure is hard to fake when your runway is running out and you have no Plan B.

What to do instead: Before your first call, have a cockroach plan. The bare minimum to survive if the raise fails entirely. If you know you can survive without this round, you'll never accept a bad deal out of desperation or lose your confidence for the next call after a string of rejections.

9. Raising More Than You Need Sounds Like Winning. It's a Trap.

Founder side: When a VC offers a bigger check than expected, it's hard to say no. More money, more runway, more room to grow. Feels like validation. Most founders take it without thinking twice. That's a mistake you won't feel today. You'll feel it at your next round.

VC side: The VCs in your next round will ask: "Does the traction justify what they raised?" Every extra dollar you took raises the bar for what counts as progress. Worse, if you raised at a high valuation and growth doesn't match, you're stuck. A flat round signals failure. A down round kills you. Some founders can't raise again at all because the gap is too wide.

What to do instead: Have a rocket plan before your first call. The maximum you'd take, at what valuation, with clear guardrails on dilution. When a VC offers more than expected, don't let the excitement make the decision.

10. A Valuation in Your Deck Can Become a Promise You Can't Take Back.

Founder side: Even with your three plans locked in, there's one more trap. Many founders put their valuation in their deck or blurb thinking it shows confidence. The moment it's in writing, you can't take it back.

VC side: A valuation in a deck becomes the anchor for every conversation. Not a suggestion. If the raise stalls and you lower it two weeks later, they think "couldn't raise at their own number." Instant red flag and hype killer. If demand picks up and you try to raise it without solid justification, you lose trust.

What to do instead: Say it verbally. Never in the deck or blurb. "Around $3M at $30M" is fine on a call. Keep your valuation alive and flexible. Don't freeze it in a document.

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Part II is coming next. What happens during and after the investor call.

If you're raising soon, DM me. Happy to jam founder to founder.