I'm dead by default

Building, learning, and iterating my way to profitability

I’m building HelloHailey in public.

I share my metrics, successes, failures, and all the ups and downs of being a bootstrapped solopreneur.

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💀 I’m “Default Dead”

As an American, I can’t dine in restaurants, go to bars, or travel. But I have more freedom than I’ve ever had before.

I choose the problems I want to work on. I figure out how to solve them. I set my own schedule and answer to no one (except you of course… 😉).

It’s only been a few months, but I’m already hooked on the lifestyle of a bootstrapped founder. But right now it’s not sustainable - I’m currently dead by default.

The term comes from this essay by Paul Graham, founder of Y Combinator:

When I talk to a startup that's been operating for more than 8 or 9 months, the first thing I want to know is almost always the same. Assuming their expenses remain constant and their revenue growth is what it has been over the last several months, do they make it to profitability on the money they have left? Or to put it more dramatically, by default do they live or die?

My goal for 2021 is to become Default Alive - to cover my living expenses with my business(es).

Around $3,500 / month should do that for me today; I value my freedom more than a mansion or expensive cars. It’s far from my end goal, but it buys me the runway to keep going.

To push the metaphorical carrot a bit further, my 2021 goal is to reach $5k MRR (monthly recurring revenue).

In Q1, I want to hit $250 MRR. I’ll be rolling out HelloHailey for free for about a month. By talking to users and iterating quickly, I’ll (hopefully) reach a point where early customers will pay me. I probably need 5-6 paying customers to hit my goal.

Time to revisit the rollout plan from my last update


😫 Failing my way to success

In Stage One, I rolled out HelloHailey to a Slack workspace with some good friends.

Before I dive into how it went, I’ll give you a quick recap of what the product does.

Hailey is a personified (remote) office dog that lives in Slack. She connects remote coworkers with games and lighthearted conversation prompts.

Sometimes she asks questions for anyone to answer:

Sometimes she’ll mention a specific person:

Sometimes she’ll stir up some friendly controversy:

Back to Stage One…

I said that founders should feel embarrassed by the first version of their product… and I was definitely embarrassed!

I’m confident my MVP will bring laughs and conversation to remote teams, but it’s miles from what I want it to be. I keep reminding myself to trust the process.

More urgently, it was buggy. First, Hailey didn’t work at all. Next, she started spamming the channel with a bunch of messages in quick succession.

So I spent a few days adding some technical stability:

  1. I fixed some bugs.

  2. I wrote some automated tests so the most critical ones never surface again.

  3. I set up better error logging and alerting.

I consider Stage One a success because of the bugs, not despite them. All MVPs are buggy. I’d rather fix them now, before launching to “real” users.


🐶 Letting Hailey run free

This week I’ll begin Stage Two. Over the next two weeks, a few friends of mine will install HelloHailey inside their teams of engineers, product managers, and designers. It’ll be my first opportunity to learn from real teams of unbiased users.

Because these first users are good friends, I’ll get quick, honest feedback. Here’s what I hope to learn:

  1. What messages drive the most engagement?

  2. What’s the right message cadence? Does Hailey chime in too often, or not enough?

Whether users love it or hate it, I’ll consider Stage Two a success if I can answer these questions.

Want to be one of the first users to try out HelloHailey for free with your team?

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❓How does your team stay connected while working remotely?

Reply to this email and let me know! I’m always looking for inspiration.


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