👋 Brendan says hi from a fork in the road

Have you ever made the same mistake twice?

My last note here was back in November of 2021, when I was shutting down my previous business, Eyeconic.

3 years later, I’m in a similar boat:

• I spent the last year building an AI journaling app called HeyOK

• HeyOK lets you journal by talking, instead of typing. It feels like a conversation with a therapist.

• So far, people try it and don’t come back.

So here I am, with another failure notch on my belt.

I’ve repeated mistakes from my last startup:

• Too little attention to distribution

• Building in a silo / not asking for enough help

I’ve also made a ton of progress:

• Built the app myself, a big deal for this formerly non-technical designer

• Spoke to dozens of people who tried the app and iterated based on usage/feedback

Progress is great. But the bottom line is still: HeyOK isn’t working.

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It’s strange.

I’ve seen glimpses of a working product:

People talking to HeyOK for a long time—10 minutes, 20 minutes—an eternity in consumer apps. They open up about problems they haven’t shared with friends or family and get emotional about it. There’s something here.

Those same people quickly abandon HeyOK. There’s something missing.

The metal detector is ringing. I haven’t struck gold.

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The weird part? I want to keep going!

I have a ton of energy for the mission and ideas on how to make it work. I lack the personal runway to do this full-time.

3 things can change my ability to work on this full-time:

1. 10 paid users who keep coming back.

2. 1+ great cofounder/collaborator: I’ve been doing this solo.

3. $250k+ funding.

Without those things, I will get a job. AI is exciting and I’d love to help build new consumer & work experiences. There’s so much opportunity right now. Future entrepreneurs will be jealous of the blue skies opening at this moment.

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I'm writing to you because sharing helps.

I want your help: Help me connect the dots. Help me meet the people I should meet. Help me celebrate progress.

Thanks for being a part of my journey. I appreciate you. I’ve gotten some lovely replies and I save all of them, like drawings on a fridge, artifacts of my community caring about me.

Let’s see what happens! The adventure continues.

With love,

-bmac¹

1. For social media/branding reasons, I’m going by my friends’ nickname for me (bmac) instead of my first name (brendan) 🤠