Introduction

Fundraising is one of the hardest parts of being a founder. It kinda sucks, actually.

It's stressful, confusing, exhausting, frustrating, bat shit... and sadly, necessary. But I've found the problem with fundraising is that it's kind of a black box.

Mixed signals online from founders (many of whom have never raised meaningful rounds themselves), stories of founders seemingly raising with no effort at all (not true), and investor feedback that sometimes contradicts the experience most founders actually have.

Not to mention the phrases every founder hears on repeat:

"Have you found a lead yet?" "Is a tier 1 interested?" "What's your traction? TAM? GTM?"

One of the reasons we started the Fun Raising podcast (which I strongly suggest you take a look at), and co-built VCSheet.com (I also strongly recommend) was to help founders navigate fundraising. To give them a leg up in a process that so often feels stacked against them. I felt the best way to get that advice was to go straight to the investors themselves, and ask them all the questions founders need answered before they raise.

We just passed 50 episodes of Fun Raising. That's 50 early-stage investors giving a peek behind the curtain and shedding some light on what otherwise feels like a black box. I spent this week combing through the episodes, looking for common patterns and overlapping advice, and pulled together the 10 things we heard most often (plus four things that didn't have consensus).

So, without further ado, here are the top 10 learnings from 50 early-stage investors on the fundraising process.

1. Your cold email gets 60 seconds at best

Most founders treat the cold email like a mini pitch deck (it isn't). Its only job is to earn the next click, and that click usually happens on a phone, between meetings, in under a minute. Most of our guests get 100+ cold inbound pitches per week, so they aren't reading yours closely. They're scanning for a few signals. Is this a real person? Is it in my lane? Is there one thing here I can't ignore?

Make them dig for these answers and they won't.

The founders who get replies make it easy. One clear line on what they build, a reason they're the one to build it, and a single proof point that's hard to scroll past.

And write it yourself. THIS IS IMPORTANT. One of the most common things I'm hearing right now is how bad AI-generated cold emails are. Investors can spot one in the first three sentences, and if they can sniff it, they'll move on to the next one.

For what it's worth, I'm a cold email believer. I raised my first check with an email made entirely of emoji. It works when it's yours. So let em' rip.

Additional tips on this topic

2. Plan on 100+ conversations before you get a YES

This was one of the most consistent thoughts on the show, and the one founders least want to hear. It routinely takes 100+ investor conversations to land a first check or a lead. Most first-time founders show up with a list of 30. That gap is why so many raises stall. You burn through the list in three weeks, collect a pile of soft nos and decide the company must be the problem.

Usually it's just the math. Early-stage venture runs at roughly a 1% conversion rate. Most investors pass for reasons that have nothing to do with you, so you need enough at-bats for the few true believers to find you. Plan for the volume upfront and every no stops feeling like a verdict.

The best founders also start long before they raise. My favorite system came from my teammate Andrew Couillard. Start taking coffee chats months early. End each one by asking if they want a call when you raise. Score each firm's enthusiasm as a percentage and multiply it by their average check. When the total hits 300% of your target, you start.

Volume doesn't mean blasting, though. When it's go time, compress everything into a tight window.

A fundraise is a sales process with one twist: You need every customer to close at the same time. So you speed some investors up and slow others down until they land together.

Additional tips on this topic

3. Few will read your TAM slide. Most go to your team slide first.

Founders pour weeks into the deck, and a lot of that effort goes to the wrong slides. Early-stage investors aren't underwriting a market model. At pre-seed there's barely a company to underwrite. They're underwriting you, and whether you've seen something the rest of the market hasn't.

That's why eyes go to the team slide first and skip the TAM slide almost entirely. A giant top-down number proves nothing, because every deck has one (and they are more often wrong). What moves an investor is a clear story. Who you are, what you noticed, why now, and how you get from a narrow beachhead to something huge.

Why the team slide? Because at pre-seed it's often the only real data in the deck. The product will change. The market story will get rewritten. The people are what's left. As one guest put it, pre-seed data rooms are ghost towns. So investors read that one slide hard, and they're looking for a few specific things.

Does your background explain why you saw this problem before anyone else? Is there someone who can build it and someone who can sell it? Is there one thing you're world-class at, not just good at everything? Would great people quit their jobs to follow you?

Pedigree matters less than founders think. Logos open doors, but earned insight is what investors remember. Lived experience in the problem. Hundreds of customer conversations. A real reason you're obsessed with this.

Now the TAM slide. Skipping it was about as close to unanimous as the show gets. If your market is obviously huge, you don't need the slide. If it isn't, a top-down number won't convince anyone.

Show your path instead. Where you enter, how you own that beachhead and how each milestone unlocks the next. One guest calls it a campaign plan. He'd met a three-month-old defense startup that already had its path to a program of record mapped out.

And don't lean on famous names of advisors to carry the deck.

Additional tips on this topic

4. The first meeting is decided in minutes

Founders walk into a first meeting thinking they have 30 or 45 minutes to make their case. The truth is most investors know their level of interest within the first five to ten minutes, and the rest of the call is spent confirming (or undoing) that first read.

So the opening matters way more than the deck. In those first few minutes, an investor is quietly answering a few gut questions. Is this person lit up by the problem? Do they know this space cold? Would great people follow them? Would I want to work for them? You can't fake any of that with slides. You show it with energy, depth and how you handle pushback. The good news is a great founder can win the room before ever getting to slide three.

And what wins those first minutes is intensity. Not polish.

Then depth. The founders who stand out can talk forwards and backwards about their industry. Why past attempts failed and why theirs won't. They can explain it to an expert, then explain it again to the rest of us.

The smartest move I heard all year was a founder who emailed the investor two days before the call. Five key takeaways, plus the top two reasons other investors had passed. Trust was built before anyone said hello.

And end every meeting with the same question.

Additional tips on this topic

5. VCs talk. Fake FOMO gets caught.

Every founder hears that FOMO closes rounds, and it's true. But the problem is most founders try to manufacture it. You've run one fundraise (maybe two). The investor across the table has seen hundreds, and they've seen every trick in the book. The fake Friday deadline. The phantom term sheet. The tier-one firm that's "getting close." Investors also talk to each other constantly, especially in deep tech where everyone seems to know everyone.

One text message is all it takes to check your story, and if you get caught, you don't just lose that firm. You lose everyone they talk to. Real FOMO is a lot more boring than the tricks. It's more demand than there is room in the round, and the only way to get there is real progress and a tight process.

This isn't hypothetical. One founder told a guest they had a soft commit from Draper. The guest checked. Draper had never said it. The founder lost both firms.

The line between storytelling and lying is simple.

Additional tips on this topic

6. Pick the partner, not the price

When you finally have options, the instinct is to take the highest number. Resist it. A seed valuation is one stop on a ten-year road, and an inflated one becomes a hurdle you have to clear at the next round. Raise at $65M out of the gate and you'd better look like a $150M company a year later. If you don't, you're staring at a flat or down round and a team holding underwater equity.

Meanwhile, the person you pick will be on the phone with you through every crisis the company has, and unlike a bad hire, you can't fire them. A few points of dilution won't matter if you build a billion-dollar company. The wrong partner can make sure you never get there.

Here's the uncomfortable part. Most VCs won't move the needle for you. My rough split is 60% net zero, 25 to 30% net negative and only 10% net positive. Your first job is avoiding the negatives. So interview your investors as hard as they interview you.

Be careful with multi-stage money at seed, too. The big name feels safe. One seed fund ran the numbers. About two-thirds of its companies reach a Series A, but the multi-stage fund that wrote the seed check leads that A only about 15% of the time.

Additional tips on this topic

7. Closing is the starting gun

The day the wire hits feels like the finish line. It's actually the starting line. You just sold a group of investors on a plan, and now the clock is running on proving it. The hardest part is the mindset switch. For a year or two you've been frugal out of necessity, squeezing every dollar (ramen, anyone?). Keep doing that after a real raise and you'll lose ground to the teams that move faster. You aren't up against capital anymore, you're up against time, and the money exists to buy speed.

That means hiring, shipping and selling now. It also means keeping your investors close enough that they're ready to back you again when the next round comes.

The most common mistake I see is raising millions and still living like you have none. Founders keep eating ramen, refuse to hire and wonder why they're falling behind.

The other half of post-close is your investors. Most founders send updates when things are good and go quiet when they're not. That's backwards.

Additional tips on this topic

8. Most startups die of people problems

Ask an investor why startups fail and you'd probably expect to hear about markets or competition. That's not what I heard. Over and over again, the answer was people. Co-founders who stop trusting each other. A founder burning out alone. A board blindsided by bad news it heard about way too late.

Markets are hard, but a strong team can pivot through a bad one (a broken team can't survive a good one). That's why investors watch for cracks from the very first call, and why the best founders treat their relationships like infrastructure. Co-founders, family, early hires and investors all need maintenance, and they need it most when things get hard.

Some investors will walk the moment they see it.

The fix starts with honesty. Your investors can only help with what they know about.

Additional tips on this topic

9. Desperate customers over cool technology

This one hits deep tech founders the hardest. You've spent years on a breakthrough, so it's natural to lead with what the technology can do. But investors kept telling me that's the wrong starting point. The companies that work start with a customer in real pain. Someone who needs the problem solved badly enough to bet on an unproven startup, sit through a long integration and take a risk on a new vendor.

"A technology looking for a market" was one of the most common killers guests named, and it rarely shows up in the pitch (it shows up a year later, when the pilots don't convert). So prove the pull early. Talk to more customers than feels reasonable, get something in writing, and let a third party say your product is worth paying for before you ask an investor to believe it.

The failure mode is subtle. The technology is real, the team is great, and nobody needs it badly enough.

The good news for deep tech founders is that proof doesn't have to mean revenue. It means evidence you did the work.

Additional tips on this topic

10. Raise for a milestone, not a number

Founders love to ask how much they can raise. The better question is how much they need. Every round is a bet that this money gets you to a specific proof point. A product shipped, a customer signed, a metric hit. That proof point is what justifies the next round.

Raise too little and you run out before you get there. Raise too much, or at too high a price, and you've quietly raised the bar you have to clear next time. Bigger rounds set bigger expectations, shrink the list of funds that can lead your next one and dilute you for money you didn't need. So work backward. Name the milestone that unlocks your next raise, cost it out honestly, add a buffer because everything takes longer than you think, and raise that. Then keep checking that it's still the right milestone by the time you get there.

The trap is that a bigger round feels like winning. It isn't. It just moves the bar higher.

Additional tips on this topic

Four additional things that didn't have consensus

The agreements are useful. The disagreements are more honest. Smart investors look at the same question and give opposite advice, usually because they're playing different games. A solo GP reading 300 pitches a week sees cold email very differently from a partner whose whole pipeline is portfolio referrals. Here's where they split, why, and where I land.

Warm intro or cold email?

This is the oldest fight in early-stage fundraising, and AI just made it louder. Inboxes are flooded with polished, machine-written outreach, and some investors have responded by trusting cold email even less.

The warm camp is blunt about it. One guest has invested in exactly one cold inbound, ever. Another has answered two cold emails in three years. To them, a trusted founder saying "this person is special" is worth more than anything you could put in a deck.

The cold camp thinks that's a trap, especially for founders without a network. Some of them read every inbound pitch personally. One guest has read over 10,000. Their view is that a stranger's intro can't make them write a check anyway, so founders should spend that energy on volume and on a great written pitch.

Where I land. Both camps are right about different investors, so play both games. Get the warm intro when it's there, and the best one comes from a founder the investor already backed. Build that network months before you raise, at conferences, online and by helping other founders. But never let the lack of an intro stop you. A sharp, human cold email still gets read. Mine did, and it was made entirely of emoji.

Spend it or sit on it?

Both camps have watched companies die. They just watched different deaths. One side has seen founders raise real money, freeze and get outrun by teams that moved faster. The other has seen founders hire ahead of need, burn through a round in a year and walk into the next raise with nothing to show for it.

The spend camp says the money is there to buy speed. Hire the best people now. Bring in the PR firm. Stop rationing like a grant-funded lab.

The save camp says slow down and learn what you actually need first. One guest calls it hiring in arrears instead of in advance. Wait until you're drowning in a task, so you know exactly what success in that role looks like, then hire for it. Another tells founders to park the cash and behave as if they never raised.

Where I land. I'm firmly in the spend camp, but speed isn't the same as headcount. Both sides agree on the real metric, which is progress per dollar toward the milestone that unlocks your next round. Spend hard on the things that clearly move that milestone. Hire in arrears for roles you don't understand yet. What you can't do is sit on the money out of fear while someone else takes your market.

Does tranching work?

Tranching means pricing your round in steps instead of at one number. The first money in gets a lower cap. Later money pays more. The idea is to reward the investors with the most conviction and to avoid the classic stall, where everyone waits for everyone else and nobody signs.

The fans say it's the best closing tool a seed founder has. One guest put it just behind a tier-one term sheet. Another lays out the exact math.

The skeptics say investors see straight through it. Nobody wants to pay more than the people closing next to them, so a step-up that isn't backed by real progress reads as a pricing trick, not momentum.

How to think about it. Tranching works when there's real demand behind it and real time between the steps. If the first million genuinely closes fast at the lower cap, the step-up is just the market talking. If you're announcing three caps on day one with no one committed, it's the same fake FOMO investors already ignore. Know which investors on your list like the structure before you lead with it.

Is the no about you?

Every founder collects dozens of passes, almost all of them polite and vague. "Not a fit for us right now." "Too early." "Keep us posted." The fight is over what those passes actually mean, and it matters because the answer decides whether you should change anything.

One camp says most passes have nothing to do with you. Funds have portfolio conflicts you can't see. Partners have internal politics. Some firms are between funds and can't deploy. And investors have little reason to tell you the real reason anyway.

The other camp says that's a comforting story. Investors understood the business fine. They passed on the founder, and you're better off accepting that and staying relentlessly yourself than rationalizing it away.

Where I land? Both are true, which is why a single pass tells you almost nothing. Treat passes as data in aggregate. If 30 investors give you 30 different reasons, that's noise. If ten of them circle the same concern, listen. And stop guessing. Ask every investor what their concerns are before the call ends, so you hear the real reason while they're still in the room.

Conclusion

Fundraising is a sales process with pretty terrible conversion rates. So treat it like one. Build the list, work the list and qualify your leads.

If you zoom out, almost all 10 of these come back to the same idea. Fundraising isn't magic, and it isn't luck (well, mostly). It's a process, and the founders who treat it like one tend to win. Keep the email short and write it yourself. Lead with your team, know your story cold and be ready to win the room in the first five minutes. Run a tight, honest process, pick partners over price and raise for the milestone that gets you to the next round.

Then, once the money hits, move fast and keep your people close. None of it is easy, and you'll still hear a lot of nos along the way. But the black box gets a lot less scary once you know what's actually going on inside it.

And remember who needs whom.

Thanks to every guest who sat down with us. On to the next 50.