Fundraising Mistakes I Only Realized After Switching to the VC Side - Part II

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+ startups. Took 500+ pitch calls. Invested in and helped 100+ founders raise over $100M.

Part I was about the mistakes you make before the first call.

This part is harder. These are the mistakes you make while looking the investor in the eye. The ones that feel like good instincts. They're not. I only saw them clearly after becoming a VC.

1. Time Is Never on the Founder's Side. It's Always on the VC's.

Founder side: You're doing everything right. Warm intros firing. Back-to-back calls. Momentum is building. But you never gave investors a deadline. You figured the momentum would speak for itself.

VC side: Without a deadline, there's always one more thing to check. One more reference call. One more week to find a "smart" reason why this won't work. Time is the ultimate deal killer.

What to do instead: Set a closing date before you send the first email. "We're closing by the end of the month." A deadline tied to a product launch. A deadline tied to a valuation increase. YC demo days work great for this. If you don't have one, create your own. When you set the timeline, you control the game and add natural FOMO to every conversation.

2. Your Job Isn't to Pitch. It's to Make the VC Pitch for You.

Founder side: You prepared a killer deck. You walk through it top to bottom, deliver a seamless 15-minute presentation, cover everything. The investor is nodding along and doesn't even interrupt with questions. Well done, right?

VC side: When a founder turns the call into a presentation, the VC doesn't need to talk. And when they don't need to talk, they disengage. They go on mute. Open X. Start reading their next deal. You didn't just lose the conversation. You lost your most valuable asset. Their attention.

What to do instead: Send the deck before the call. Use the meeting for conversation, not a one-sided presentation. Ask them questions. Let them brainstorm with you. When they start sharing ideas, they stop evaluating and start co-building. Confirmation bias does the rest. You want them to leave thinking "we figured this out together." Not "I sat through a pitch."

3. Short Answers Close Questions. Long Answers Open Questions.

Founder side: The VC throws a tough question. You practiced for this one. You nail it in 30 seconds. Clean, confident, done. But the silence after feels awkward. So you keep going. You add context. A caveat. A second example.

VC side: The founder already gave a perfect answer. The VC was ready to move on. Had more things to dig into. But the founder kept explaining. Then the founder mentions something that sparks a completely new concern. "That's it. That's why this won't work."

What to do instead: Answer the question briefly. Stop. Let the silence sit. The investor will ask a follow-up if they need more detail. Your job is to answer the question, not every question around it.

4. You Can't Sell to a VC Who Never Had to Sell to You.

Founder side: You walk into the call ready to present. The VC says "tell me about what you're building" and you go non-stop. Questions keep coming. Before you know it, it's the 30-minute mark. The VC says "this was great, I've got to jump." You never asked a single question.

VC side: The best founders pick their investors. VCs know this. When you don't question their value, their track record, their portfolio support, you're signaling you'll take any check from anyone. And every minute you spend answering without asking, the dynamic hardens. They attack. You defend.

What to do instead: Make sure you ask questions first. "What's your thesis in this space? How do you support founders post-investment? What does your decision timeline look like?" When a VC feels like they need to earn a spot on your cap table, the dynamic levels out. It's no longer an interrogation. It's a potential collaboration.

5. Momentum Doesn't Stand Still. It Either Builds or Dies.

Founder side: You had a great call. Real engagement, sharp questions, good energy. They said "we'll get back to you soon." A week goes by. Nothing. So you follow up. "Hey, wanted to check in. Any update on next steps?"

VC side: For the strongest founders, a week is a long time. They ship features. Close customers. Collect checks. When they follow up, the email opens with momentum and closes with a shrinking allocation. "Just checking in" says the opposite. Nothing happened in seven days. And if nothing happened in seven days, maybe nothing is happening at all.

What to do instead: Don't stop building while you're raising. Ship. Close customers. Get more checks in. Then follow up with the update. "Signed 3 new customers this week. Down to only $200K left in the round." That's the headline. Then add "any update on your end?" as the footnote.

6. The Pitch Deck Gets You the Call. The Investment Memo Gets You the Check.

Founder side: Had a great call and answered everything. You follow up with a thank-you email and attach the deck. You figure everything the VC needs is already in there. They'll share it around internally and you'll get a check.

VC side: Before writing a check, VCs need an investment memo. Why now. How this returns the fund. What needs to be true for this to work. Your deck answers maybe 30% of that. The rest takes hours of research, thinking, and writing. They need to do that while handling 10 other deals on the table.

What to do instead: Write your investment memo before talking to any VC. After the call, share it with them. Your thesis becomes their lens. You just replaced 80% of their work. When that memo is already written for them, they're not building a case from scratch. They're editing yours.

7. An Intro Without a Check Isn't a Favor. It's Additional Due Diligence.

Founder side: You pitched an investor. It went well. They seem interested and offer to introduce you to a few VC friends. You're thrilled. More warm intros. More fuel in the pipeline. It feels like momentum.

VC side: If that investor hasn't committed, they're not vouching for you. They're outsourcing diligence to a friend. The DM reads something like "interesting founder, not sure yet, worth a look?" And it's way easier for the receiving VC to sound smart by finding holes than by championing your deal.

What to do instead: Only accept intros from investors who are committed. "I invested in these guys and you should take a look" is a warm intro. Anything less is homework for another VC. If they offer intros without committing, flip it into FOMO. "Thank you, I'd love to connect with them but I'm slammed with back-to-back investor calls."

8. A Verbal Yes Means "Give Me More Time." A Written One Means "I'm In."

Founder side: You had a great call. Nailed it. The VC says "we're in." You count it toward your round. Update your spreadsheet. On the next investor call, you say "we just closed another check, room is getting tight."

VC side: A verbal commit is a free option. It keeps the deal alive without committing capital or time to make an actual decision. There's zero reputational cost to backing out of something never written down. Market shifts. A partner raises a concern. Your "yes" quietly becomes "let's revisit next quarter." You'll get silence instead of wiring instructions.

What to do instead: After any verbal commit, immediately get written confirmation using the YC Handshake Protocol. Amount. Valuation cap. Timeline to wire. Once it's written, backing out carries real reputational cost. Only after that do you count them in.

9. Your Call Isn't a One-to-One. It's One-to-Many.

Founder side: You tailor your pitch for each investor. Reorder your priorities based on what each one cares about. Lead with MAU for one, ARPU for another. And when they ask who else is in, you spill a name under pressure. Even if there's no handshake yet.

VC side: The moment you name a VC, they're DMing that person. Just after the call if not during it. They learn it's just tentative at best. Your integrity takes the first hit. Then they compare notes and find discrepancies in your priorities. You lose not only the round but, more importantly, your reputation.

What to do instead: Assume every investor you talk to is on the same team, sharing notes in real time. Don't name-drop VCs to create FOMO, even if they look extremely interested. Same story. Same priorities. Same numbers. Every single call.

10. Today's "No" Is Next Round's "Yes." If You Keep the Relationship Warm.

Founder side: You had multiple calls with a VC. Made it to the partner meeting. Felt great. Two days later, a pass email lands. Frustrated, you fire back a wall of text disagreeing with their reasons. Feels justified. Or you go silent. Remove them from your list and never send an update.

VC side: A pass isn't a verdict on your company. It's a snapshot of right now. VCs pass for reasons that have nothing to do with you. Low allocation. A distracted partner. Bad timing. The ones who give feedback are leaving the door open on purpose. But an emotional reply slams it shut. And silence lets it close on its own.

What to do instead: Thank them. If you disagree, share it briefly without being too defensive. Then keep them warm. Add them to your investor update list. Send quarterly progress. A warm relationship and consistent progress can turn a "no" into a "yes" easier than any cold pitch ever will.

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Every mistake in this thread felt like the right move when I was a founder. Present thoroughly. Over explain. Follow up without FOMO. Accept warm intros. Celebrate a verbal yes. None of it works the way you think it does.

Your instincts were trained by the wrong side of the table.

More coming soon. I'll be covering the most common mistakes I see in pitch decks, blurbs, and investment memos. Follow me so you don't miss it.