Asking for help is one of those things that seems like it should be easier than it is. It’s literally just asking. 

Words come out of your mouth (or fingers/thumbs since these things usually happen over email and text). Someone says yes, no, or ignores you, and life goes on. 

But for a lot of founders, it becomes this weird emotional obstacle course. They overthink it, avoid it, soften it, bury it, make it vague, or do that thing where they pretend they’re just “catching up” when everyone involved knows there’s an awkwardly worded ask coming three sentences later. 

I say this with some sympathy because I’m not a gifted help asker myself. 

I was raised to never be a burden to others. In my house, if you could even hypothetically do something yourself…that’s what you should do.  That sounds lovely and polite until you realize it can also train you to underutilize every relationship you’ve ever built and eat rocks when you could’ve been at the finish line eating dessert. I still default to “prove you can do it yourself,” even when that is obviously the slower and dumber path AND the path i so often coach against in my content. 

So yes, this is going to be a little bit of a “do as I say, not as I do” essay. 

Maybe this isn’t something that comes natural to you but unfortunately, if you’re fundraising, you don’t really get to avoid it. Fundraising is basically one giant coordinated campaign of asking for help. Every investor intro is a mini request for help. Every request for feedback, every “who should I talk to?”, every “would you be willing to forward this?” is asking someone else to spend a little time, attention, or social capital on your behalf. And if it’s not super obvious… the final ask for money is one massive request for help. 

That’s the job. Or at least a bigger part of the job than founders want to admit. 

This came up recently with a founder I was helping with fundraise prep. His background was absurdly strong. Stanford. Google. Startups with successful exits. Friends with the kinds of entrepreneurs most founders would love to have anywhere near their cap table or intro path.

In other words, not someone lacking access. But when we got to the part of our work where he actually needed to ask people for help, he froze. Not fully. Not dramatically. Just enough that you could feel the friction. The names were there. The possible paths were there. The people who could help were there. But every ask suddenly felt like this heavy thing. 

I understood because I see this constantly. But that doesn’t make it any less disappointing to see. 

Founders spend years building credibility, being thoughtful, helping others, staying in the game, earning real relationships, and then when it’s time to call on a little bit of that goodwill, they act like they’re doing something shameful. It kills me because fundraising is already hard. You don’t need to add difficulty points by incorporating the “I refuse to ask anyone for anything” move. 

I’d like to try to fix this at least slightly.

So here are 5 ways founders make it harder for people to help them fundraise (and some potential fixes).

The worst time to remember your network is when you urgently need it. Yes of course you’ve been heads down building but it won’t help you to disappear for three years before sending someone a note that is basically, “Hey, hope you’re well! Anyway, can you introduce me to your most famous investor friend?” 

I’m exaggerating slightly, but not that much. People are much more likely to help when they feel some ongoing connection to your life and work. They don’t need to be updated every week. They don’t need a board deck. But they do need some evidence that the relationship exists outside of the moments when you need something. This is where founders get too hermit-y.  Some neck beard tendencies are good, but if you go to far your network won’t be ready to jump in. 

Here are some ideas on how to with little effort keep that that thing well watered:

- If you’re traveling to a city, look people up.
- If something reminds you of someone, send the note.
- If it’s the new year, send more happy new year messages than feels normal.
- If you have enough going on personally or professionally, send an annual update. Not a self-congratulatory investor update disguised as a friendship note. A real update. What happened this year, what you learned, what you’re excited about, maybe what was hard.

The point is not to “network”. Forget about nurturing an “asset” or prepping for a fundraise. The point first is to stay connected to people that maybe you want to hear from, that you’d want to help if they knew they could ask, is to keep human connections alive so that our future AI world will few less robotic.  Use that as your main goal…having something that might help with fundraising is an added side benefit.

A network is not an emergency-use-only asset. It’s a living thing. If you leave it in a drawer for five years, don’t be surprised when it feels stiff when you finally try to use it.

Sometimes the relationship is fine. The person likes you. They would probably help. You have done enough over the years to make the ask reasonable. And then you just don’t ask. You hint. You hover near the ask. You say “would love your advice” when what you really mean is “can you introduce me to these three people?”

You send a long update and hope the other person magically identifies the place where they can help and volunteers the exact thing you were too uncomfortable to request. This is fundraising by telepathy, which is not a category I recommend. I get the instinct, though. Some people really don’t want to feel like a burden. Some people are culturally predisposed to avoid asking. Some people worry that the ask will change the relationship or reveal that they needed something all along. And some people, myself included, have a slightly broken pride mechanism where asking for help feels like admitting they couldn’t figure it out on their own.

But if you’ve been good to people, and the relationship is real, and the ask is reasonable, then you are allowed to make it. Not demand it. Not guilt them into it with a scoreboard check. Just ask. Give them the dignity of deciding for themselves instead of pre-rejecting yourself on their behalf. “They’re probably too busy” might be true. It also might be the story you’re telling yourself because it’s more comfortable than risking a no. And btw, a no is usually not fatal. Founders hear no from investors all the time and somehow survive. You can survive one from a friend too.

Side note: one thing that can help with this is think about how much you’d wantto help them if it were easy. That can often remind you of where you stand with them!

There is a version of asking for help that rides a wave, and there is a version that exports your uncertainty onto someone else. That second one is where founders get themselves into trouble. They’re not fully excited yet. They haven’t really found the conviction in the fundraise. The story is still mushy. The target investor list is half-researched. They are sort of asking for an intro, but if you listen closely, they are also asking the other person to validate whether the company is worth introducing at all. 

You have to remember: if you ask me for an investor intro, I am not just moving information from one inbox to another. I’m spending some amount of social capital. I’m telling the investor, implicitly, “I think this founder is worth your time.” That doesn’t mean I need you to be perfect. I don’t need every answer to be crisp like you were assembled in a fundraising lab. But I do need to believe you’re going to represent yourself well. And honestly, you should believe that too.

The best intro requests have this quiet confidence underneath them. Not arrogance. Not necessarily “this investor would be lucky to meet me” energy but hey also not bad.... It’s more like: I know what I’m building, I know why it’s exciting, I know this person would be interested, and I believe this is a good use of everyone’s time. 

If you don’t feel that yet, it doesn’t mean you should never ask. It probably just means you need to do more work before asking. AND THAT’S OK!

Keep working on building your own conviction in the opportunity. Tighten the narrative. Build the investor list more thoughtfully. Get clear on the round. Make sure you can explain why this company matters and why this intro makes sense. When you ask with real conviction, the other person can feel it. When you ask while secretly hoping they’ll provide the conviction for you, they can feel that too.

My favorite bad fundraising ask is some version of: “Do you know any investors who might be interested?”

The answer is “probably” but what is your expectation here? Am I supposed to mentally scan every investor I’ve ever met, map them against your sector, stage, traction, check size, geography, fund timing, current appetite, my relationship strength, and whether I’m willing to burn political capital on this intro?

That’s an exaggeration of course.  But it’s not an exaggeration to say that even a light scan of who i might be able to introduce is a tax that many busy people who have great networks will avoid if they can.

A lot of founders think they are being easygoing by keeping the ask open-ended. They don’t want to be too demanding, so they make it broad. But broad often means cognitively expensive, and cognitively expensive requests die quietly in inboxes. 

The better move is to do the work ahead of time.

If you want intros, send specific names. If you want feedback, say what kind of feedback. If you want advice, ask the actual question. If someone needs to forward something, include the forwardable blurb before they ask for it.

Bad version: “Know any investors who might be a fit?”

Better version: “I saw you’re connected to Sarah at XYZ Ventures. She’s invested in two companies selling into regional hospital systems, which is close to our wedge. Would you be comfortable introducing us? I included a short blurb below you share if helpful.” 

Those two asks are not even in the same universe. The second one shows that you thought about fit. It shows that you value the other person’s time. It makes the action obvious. It also gives them an easy way to say no if they don’t think it’s a fit, which is underrated. 

A lot of my fundraising content talks about urgency, scarcity, FOMO, momentum, all that stuff. I love that stuff…and of course those matter. But a shocking amount of fundraising execution is just reducing friction. Make it easy for the person who wants to help you to actually help you.

This one happens because a lot of fundraising asks travel through personal relationships. You know the person. You have history. Maybe you worked together, went to school together, played on the same team, saw them at a wedding, met over a drink at a networking event at CES in 2019 and now technically count each other as friends... 

So when you write the email, you first try to lead with personal. Personal is good and human and you should be a good human.

But then you try to have the personal note flow seamlessly into the fundraising ask. It sounds like: “Hey John, hope things are going well on your side. How’s your dog? On my side, I started a company last year called XYZ Corp which is at the cutting edge of AI and we’ve been executing really well. We’re now going out to raise...” 

You’ve seen this email. I know because it’s probably in your sent folder somewhere. I have definitely sent some version of this email, so I’m not judging from an ivory tower here.

The issue with that blended personal and professional writing is that it doesn’t accomplish either goals particularly well. The personal part feels thin because it’s obviously just the little on-ramp to the ask. The professional part gets wordy because you’re still writing in the tone of a casual catch-up note, so instead of being precise, you end up with a bunch of soft conversational filler around the actual information.

A better structure is to separate the two. I call this format the “Email Appendix”. 

Here’s how that works: start your email like a normal person. Actually be personal, but keep it short. “Hey John, it’s been a while since we hung out at Brian’s wedding. That was so fun. I wish we got more chances to catch up.”

Then create a clean break. “Anyway, I’m working on a fundraise for my company and was hoping you might be able to help with an intro. I included more context below so you can see if it makes sense.”

Then sign off like a human “Best, Jason”  Then below that, put a completely new section “My company: XYZ Corp” and under that include the useful stuff. Company description, highlights, specific intro request… use short impersonal wording, use bullet points (all the things that would feel weird in a personal note).

The Email Appendix format is great because it lets the personal part be personal and the professional part be precise. You don’t have to make one paragraph do every job. I think this is especially important because people can feel when you’re using personal warmth as camouflage for a vague ask. It’s not malicious. It’s just awkward. But it still creates that tiny bit of distrust where the reader is like, “Are we catching up or am I being processed through a fundraising sequence?”

Don’t make them wonder. Be warm, then be clear.

Being good at asking for help does not mean everyone says yes. People are busy. Some people won’t think the intro is a fit. Some people won’t want to spend the social capital. Some people will intend to reply and then your email will sink into the swamp forever. That’s all part of it. The goal is not to engineer a 100% yes rate. The goal is to stop creating unnecessary reasons for people to not help. If your network is cold, the ask feels transactional. If you never actually ask, people can’t help you.

If you ask before you have conviction, people feel like they’re being asked to carry weight you haven’t picked up yet. If your ask is vague, you turn goodwill into homework. If you muddy the message, you make people work too hard to understand what role you want them to play. None of these are moral failures. They’re just execution mistakes. And in fundraising, execution mistakes compound quickly. It already takes a ton of time so don’t make these errors build up. 

This is the part I keep coming back to for myself too. I can tell founders to short circuit the process by asking for help all the time. I can explain why it matters, how to do it, how to make it easy, how to be specific. And then in my own life, I will still catch myself trying to prove I can do everything alone like some noble little idiot. So I’m not writing this because I’ve perfectly solved it. I’m writing it because I’ve seen how expensive it is when founders don’t. 

Make the ask. Make it specific. Make it easy to say yes (and easy to say no). Keep the relationship human, but don’t hide the professional request inside a fog machine of fake casualness. 

You won’t always get help.

…but if you don’t ask, you are guaranteeing you won’t. 

How cringe is this next sentence going to be? Maybe a bit, but it’s too appropriate to not use. 

Remember: you miss 100% of the shots you don’t take. 

Alright, hope all of this has made sense… till next time 

Be chased, 
Jason

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