YC S26 is getting close to demo day, so I’ve been thinking about our fundraising last year.
I don’t think I was particularly great at fundraising. We got it done, but looking back, there are a bunch of things I would do very differently.
This is not “how to fundraise”. This is mostly a list of things I think would’ve worked better for me, after having gone through it once.
Stop being an energizer bunny
I thought I had to be “on” all the time.
High energy. Confident. Excited. Constantly selling.
I think I overdid it.
Being confident and acting confident are very different things, and investors talk to enough founders that they can probably tell.
If I did it again, I’d spend much less energy trying to project what I thought a fundable founder was supposed to look like. I’d slow down, listen more, and just know my stuff really well.
Own your calendar
One stupid thing I did was send investors my cal.com link.
I thought I was being efficient. What I was actually doing was giving everyone else the ability to optimize my calendar around their convenience.
I wouldn’t do that again. I’d give people three slots.
“Tuesday at 2, Wednesday at 11, or Thursday at 4?”
That sounds like a tiny optimization, but when you’re doing multiple investor meetings every day, it matters a lot.
I’d batch meetings, protect the hours when I’m sharpest, and be much more intentional about which investors I talk to when.
Fundraising is one of those weird periods where calendar management is actually strategy.
Treat fundraising like sales
Last year I mostly thought about fundraising as pitching.
If I did it again, I’d think about it much more like running a sales pipeline.
I’d research every investor before the meeting. What have they invested in? What do they actually care about? How do they make decisions? Are they capable of leading? Are they mostly looking to follow someone else? Who do they tend to follow?
Then I’d cluster similar investors together and, when possible, meet them around the same time.
Not because I’d tell everyone a different story. The core story should stay the same.
But I’d change the emphasis.
Some investors care about the market. Some want to understand the product. Some care about technical differentiation. Some mostly want enough social proof to know that someone they respect is going to lead the round.
Same company. Same story. Different emphasis.
I think I would’ve gotten much better at pitching much faster if I had approached it this way.
Pitch to your cofounders. Yes, it’s embarrassing
I’d practice the actual pitch in front of my team way more. Especially my cofounders.
It’s embarrassing. You’re pitching the company to people who already know everything about it, and you’re probably going to sound stupid the first few times.
Do it anyway.
And for 30 minutes, ask them to forget that they’re your cofounders.
Be the annoying investor. Interrupt me. Question my assumptions. Tell me when something doesn’t make sense. Ask the stupidly obvious question that I’ve stopped noticing because I’ve been thinking about the company for years.
I’d rather get destroyed by my cofounder at 10pm than discover the hole in my pitch in front of the investor I wanted most.
Warm intros are king
I underestimated how much fundraising is a hive mind effort.
The best intros are warm. But there are different levels of warm.
An investor who already believes in you introducing you to another investor is incredibly powerful.
Another really good one is a founder introducing you to their investor. If your friend has already made someone money, and they tell that investor “you should really meet these guys”, that means something.
So I’d ask for intros much more deliberately.
Not spray “can you intro me to VCs?” everywhere. I’d ask people who genuinely believed in us: “who do you think I should meet?”
And I’d do the same for other founders.
Especially inside YC, fundraising shouldn’t be 200 companies individually trying to reconstruct the same investor graph from scratch. Help each other.
I’d do a fundraising retro every night
This might be the biggest thing I’d change.
After 5 or 10 investor meetings, everything starts blending together.
You vaguely remember that one investor really liked something. Someone else asked a question you answered badly. Another meeting felt amazing, but you’re not entirely sure why.
Then you wake up and do it again.
I wish we had recorded every investor conversation and spent 20-30 minutes every night actually reviewing them.
Where did they lean in? Where did I lose them? What questions keep coming up? What part of the explanation consistently lands? What objections am I answering poorly? Who was genuinely excited and who was just being polite?
Then I’d change the pitch the next morning.
During fundraising you’re getting an absurd number of data points compressed into a couple of weeks. Not systematically learning from them was probably one of my biggest mistakes.
Use tools like anarlog, circleback, fathom, whatever. Don’t throw away the data.
Shameless plug: anarlog is actually pretty great for this now. Record the meetings, transcribe them, and dump them into AI at the end of the day.
If your cofounder is fundraising, give them some space
This sounds contradictory after saying “destroy their pitch during practice”, but there are two different modes.
Before the meeting: be brutal.
After the meeting: be supportive.
Fundraising sucks.
Unless you’re the hottest kid on the block, a lot of it is rejection, ghosting, “let’s keep in touch”, meetings you thought went incredibly well that somehow go nowhere, and repeatedly performing the same excitement and conviction for the 8th time that day.
It is genuinely exhausting.
So if your cofounder is doing most of the fundraising, don’t critique every single call afterward. Don’t ask “how did it go?” 10 times a day. Don’t turn every rejection into an emergency strategy session.
Take other things off their plate. Let them complain. Keep the company moving.
Fundraising already generates enough disappointment on its own.
Don’t beat yourself up if you’re not Travis Kalanick
Some people are just incredibly good at fundraising. They walk into a room and people want to give them money.
Maybe you’re that person. Great.
I don’t think I naturally am.
And I think I wasted some energy wondering why I wasn’t better at it instead of figuring out how I could get better at it.
Everyone has different strengths.
Fundraising is important, but your ability to fundraise is not the same thing as your ability to build a great company.
One last thing about YC advice
Listen to your group partners. Listen to your cofounders too.
But don’t turn every piece of advice into a law of physics.
YC has to give advice to an enormous number of companies, with different founders, markets, products, traction, and fundraising dynamics. Some advice will be incredibly relevant to you. Some won’t.
I think the useful distinction is this: failure formulas are much more transferable than success formulas.
YC has seen an absurd number of companies fail in the same ways. When they warn you about one of those patterns, listen very carefully.
But there probably isn’t a universal sequence of steps that turns you into the hottest company in the batch.
You have to figure out your own success formula.
Anyway, this is just the advice I wish I could’ve given myself a year ago.
Good luck, S26.
August 10, 2026