I had the tweet typed out. My thumb was over the button. And I sat there feeling like an idiot.
I was about to publicly ask the CEO of Slack, a company worth billions, to give my tiny community free software.
For almost a full minute, I couldn't send it.
This was years ago. I've since landed 200+ press features, in the New York Times, the BBC, Forbes, and on Good Morning America, and built a handful of companies. Back then I was just a guy running a group chat with no money and a problem I couldn't solve.
The group was called 18percent. A free mental health community on Slack. It grew to more than 18,000 people.
It was named for the roughly 18% of Americans living with mental illness. Good Morning America covered it. So did the Washington Post. We even partnered with Crisis Text Line. It became a place thousands of people leaned on.
Here's what I was stuck on. As we grew, members wanted to save conversations and go back to reread them. The kind of support you return to at 2am when you need it most.
Slack's free plan didn't let you do that. We needed the paid features. And we had exactly zero dollars to pay for them.
I looked for workarounds for weeks. Exported transcripts. Cheaper tools. Hacky spreadsheets.
None of it felt right, because the community lived on Slack and moving it would have killed it.
So I did the thing that felt embarrassing. I stopped hunting for a clever workaround and just asked.
Publicly. On Twitter. To Stewart Butterfield, the CEO of Slack himself.
I don't remember the exact words. It went something like this: I run a mental health community of thousands of people on Slack, we have no budget, and the paid features would change what we can do for them. Can you help.
Then I put the phone down and tried to forget I sent it.
His chief of staff had it set up within an hour.
An hour. No press release, no announcement. Just a CEO quietly telling his team to take care of a mental health community he'd learned about sixty minutes earlier.
Two things have stuck with me ever since.
The first is that people are far more generous than you expect, as long as the mission is real. Butterfield didn't help because I mattered. He helped because thousands of people were using his product to hold each other up, and that meant something to him.
The second is the one I think about almost every week. The ask you're embarrassed to send is usually the exact one that changes everything.
I almost didn't send that tweet because it felt small. Needy. Like I was bothering someone way above my pay grade.
The polished move was to stay quiet and find a workaround. It would have left us stuck.
I've built my whole career on this since. Almost every good thing that's happened to me started with an ask I was nervous to make.
The cold email that put my dad's COVID story in the New York Times. The investors I had no business pitching. The tweet to a billionaire. None of it was talent. It was just messages I sent that most people delete.
Most people never send the message. They write it in their head, talk themselves out of it, and move on with a quiet little "what if."
The whole game is sending the message.
One thing to try this week.
Think of the one ask you've been sitting on. The pitch. The intro. The favor. The email you've rewritten four times and never sent.
Send it this week. Keep it short and honest. Say what you're doing and what you need. The worst case is a no, which is exactly where you're standing right now anyway.
So tell me. What's the ask you keep talking yourself out of? The pitch, the cold email, the favor. Hit reply and tell me what it is. I'll tell you if I'd send it, and how I'd word it.
Zach
P.S. For most founders, the scariest ask is pitching a journalist. PressPitch finds the right reporters for your story and writes the pitch for you. Free for 7 days, no credit card. presspitchai.com
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