Are You Poor, Broke, and Not Dumb, Trying to Start a Business?

If you’re smart but broke, the hardest part of starting something isn’t building it. It’s figuring out what to build, and then actually reaching out to strangers.

Finding a path #

I found my semi-path almost by accident. I posted on Reddit, got into a conversation with an attorney, heard a real need, and built something to solve it. No grand vision. The idea actually came from my then-girlfriend’s brother-in-law, and funny enough, he never ended up using the thing I built either.

If you don’t know what to build, solve your own problems and talk to people. Most needs don’t show up until someone walks you through their day and you notice the part they hate doing. The Mom Test is the book to read on how to talk to users without leading them into telling you what you want to hear.

Hunter S. Thompson’s letter to Hume Logan makes a related point: instead of picking a fixed goal, find a way of living that fits you. It works for finding an idea too.

Reaching out is the hard part #

Talking to strangers to find a need takes work. You have to ask for help without being annoying, and there’s a good guide on how to ask for help. You also have to be willing to send what one writer calls “earnest spam”: cold outreach that’s thoughtful instead of lazy.

When you do send that email, keep it short and specific. Say what you’ve built and who you’ve already talked to so you’re not a total stranger, ask for a small amount of their time, and offer to pay for it. Something like:

Hi [Name],

I’m building [thing] for [who], and I’ve been talking to a few [role]s to understand [problem] better. Would you be open to a 20-minute call? Happy to pay for your time or send something for the trouble.

Thanks, Chris

Expect a lot of nos. This video, “After 1000 Rejections, I Learned This…”, is a good reminder of that.

The honesty tension #

This is the part I go back and forth on.

When you reach out, there’s pressure to inflate yourself so people take you seriously. A few white lies to look bigger and more important than you are.

But honesty matters. People only share their data and their real problems when they trust you. You might get away with puffing yourself up once, but it falls apart fast when the whole thing depends on people handing you sensitive information.

If you want the business side #

If you’re bootstrapping, these notes on designing the ideal bootstrapped business are a good filter for which ideas are worth chasing.