</figure>

I try to be helpful.

I say yes a lot.

People in the community reach out, founders ping me, friends text me, and most of the time I genuinely want to be useful. I like seeing people make progress. I like seeing people get unstuck.

But every so often, someone makes it harder than it needs to be—without realizing it.

It almost always comes down to the shape of the ask.

Not what they want, not how big it is… but whether the request is specific and finite or general and open-ended.

That distinction makes all the difference in whether someone says “Sure, I can squeeze that in” or “Oh no, this is going to be a whole thing.”

Let’s break this down.

People Don’t Budget Minutes. They Budget Commitments.

Whenever someone asks for help, what I’m really evaluating isn’t the time—it’s the commitment.

People think in blocks:

“Do I have room for another ongoing thing in my life?”

Not:

“Do I have 20 minutes free next Tuesday?”

A finite ask is easy to process:

• 
  

  “Can you look at my website for 10 minutes and answer 3 questions?”

  
  


• 
  

  “We’re having two strategy sessions over the next month, each two hours. Can you sit in and give investor perspective?”

  
  

  
  

Those might be small or large lifts—but they’re contained.

They end.

If I have a light December, maybe I can make those four strategy meetings work. I know what I’m signing up for.

An open-ended ask goes in a completely different mental category:

• 
  

  “Can you help me think through fundraising?”

  
  


• 
  

  “Can you advise us as we build this out?”

  
  


• 
  

  “Can we hop on calls as needed?”

  
  

  
  

  That’s not an hour. That’s a new relationship, a new permanent slot in the calendar. Even if the actual time commitment is tiny, it feels infinite and everyone has a limited number of “infinite” slots.

  
  

So when you ask someone for help, the first question they’re really answering is:

Are you giving me something I’ll be done with at some point… or something I’m now responsible for forever?

Help Has to Feel Effective

Once someone agrees to help, the next thing on their mind—whether they articulate it or not—is:

Will this actually move the needle?

People want their time to have impact. So two things matter a lot:

1. Are you someone who acts on advice?

Nothing kills future help faster than this sequence:

• 
  

  You ask for guidance.

  
  


• 
  

  They give you a clear suggestion.

  
  


• 
  

  A month later, you come back with the same problem.

  
  


• 
  

  And you didn’t try the suggestion.

  
  

Why would someone record a custom podcast for an audience of one…
…if you didn’t listen to the 200 episodes that already exist on the topic?

If you’re not willing to help yourself, why should someone else feel optimistic about helping you?

2. Are you doing the basics before I show up?

There is so much publicly available material about fundraising, building, hiring, pitching—you name it.

If you show up with absolute beginner questions you could have solved with a single search, it reads as:

• 
  

  “My time is too valuable, so I didn’t spend time on homework.”

  
  


• 
  

  “Your time is free, so you can do it for me.”

  
  

That’s disrespect, even if you don’t mean it that way.

Compare that to someone who shows up prepared:

“I’ve listened to X, read Y, watched Z. Here are the three places where I’m seeing conflicting advice. Here’s why I think your experience could help me choose between A and B.”

That is a great meeting. That’s a meeting worth saying yes to.

Often, the person has already done all this—they just don’t make it clear in the ask.

Earn the Ongoing

Ongoing support is not something people grant on the first ask. You work up to it.

You do that by making each interaction…

1. 
   

   Finite

   
   


2. 
   

   Prepared

   
   


3. 
   

   Actionable

   
   


4. 
   

   Closed-loop

   
   

“Closed-loop” means you follow up. It sounds simple, but almost nobody does it.

• 
  

  “Tried A and B like you suggested—A worked. Thanks again.”

  
  


• 
  

  Two weeks later: “Here’s the result. Just wanted to close the loop.”

  
  

What that demonstrates:

• 
  

  You listen.

  
  


• 
  

  You act.

  
  


• 
  

  You don’t create new work for the other person.

  
  


• 
  

  You make progress without them needing to carry you.

  
  

String together a few of those interactions, and suddenly if you ask someone:

“Would you consider joining my board?”

…they might actually say yes.

Because every data point tells them:

“This person is a great use of my time.”

Common Asks That Backfire

There are a few patterns that almost always signal a deeper issue—and where the ask is not really the thing the person wants help with.

“Can you help me find investors?”

Usually this means:

• 
  

  You have a top-of-funnel full of passes,

  
  


• 
  

  And you think the issue is that you need more top-of-funnel.

  
  

But there are tons of investor lists. Crunchbase exists. Referrals exist. Founder communities exist.

Lack of names isn’t the problem.

The problem is usually something like:

• 
  

  The idea isn’t fundable at the stage you’re at.

  
  


• 
  

  You haven’t done enough work to make it compelling.

  
  


• 
  

  Your story’s unclear.

  
  


• 
  

  Or investors already gave you a signal… and you didn’t want to process it.

  
  

“Help me find investors” is often code for:

“Help me avoid the hard truth.”

That’s not a good ask.

“Can you look at my deck?”

This one sounds reasonable on the surface, but it’s often a trap—because the founder usually doesn’t want feedback. They want validation.

Here’s how it typically goes:

• 
  

  They send a 22-slide deck with no context.

  
  


• 
  

  No version history.

  
  


• 
  

  No explana