The endless treadmill

Why I'm prioritizing the journey over the destination

👋 Welcome to The MVP Sprint! I’m Tim.

I’m sharing my public process of taking HelloHailey from idea to thriving SaaS startup as a bootstrapped solopreneur.

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I’ll be happy when…

I’ve spent most of my professional life optimizing for the future:

  • As a 22-year old founder at a VC-backed startup, working 80-hour weeks for less than minimum wage - It’ll all be worth it when we’re billionaires changing the world (spoiler - it didn’t happen…)

  • As a Product Manager at a Silicon Valley tech company - I’ll be happy when I can quit, travel, and be a founder again.

  • As a bootstrapped founder (now) - I’ll be happy when HelloHailey hits $10k / month.

Happiness is a moving target.

Mortgaging the present for the future creates debt that can never be paid down. No amount of money can buy back time.

Actions express priorities

When I skipped vacations, nights out with friends, or trips to visit family, I was implicitly saying that these things were less important than my future goals.

So what’s the inverse of this?

Optimize for the journey

By expressing my priorities as uncompromisable constraints, I’m prioritizing the “journey” ahead of the “destination”.

For me, these constraints are (in no particular order):

  • Family - I’m going to travel to see my immediate family every quarter.

  • Friends - I’ll go out of my way to visit close friends. I’ll never miss an important social event.

  • Travel - I’ll live nomadically for as long as I enjoy it, spending 1-2 months in each destination.

  • Health/Fitness - I'll work out almost every day, and budget enough money to eat healthy.

With very few exceptions, these constraints will always come before my company.

This tradeoff increases my monthly burn and decreases how quickly I can grow. But I can solve for these problems as long as I'm playing the right game.

Pick the right game to play

I believe this approach is possible for most people if they’re building a business where:

💸 They can start making money in 1-2 months, not 6-12.

I launched my HelloHailey MVP in 3 weeks. I should make $3k-$5k in revenue in June. Early revenue + low-cost lifestyle = infinite runway.

💰They don’t need outside capital

There’s nothing wrong with raising money, but it makes it much harder to ruthlessly prioritize like I’ve described. When you raise money, you’re hiring a boss.

I built up runway by living well below my means for years, and build and operate HelloHailey by myself.

🌏 They’re not in a large, winner-take-all market

They can be successful with a small chunk of a huge market or a large chunk of a small niche. Good luck competing with Instagram or Airbnb while working 20 hours a week in Bali.

HelloHailey is a 7-figure opportunity with <1% of my total market (all remote teams).

❗️Their product or service isn’t “mission critical” for their customers

They won’t be getting calls from angry CEO’s if it goes down at 3am.

I'd get some emails from disappointed team members if HelloHailey went down for a couple days, but that's probably it.

Play it with the right strategy

When I work around my constraints, I have less time to work. So I have to be ruthlessly efficient.

I’m optimizing for one metric - the number of teams actively using HelloHailey. Every day, I work on what will be most impactful towards making this metric go up:

🌟 Choose a north star metric.

👣 Set a path to get there.

🙅‍♂️ Eliminate everything else.

💸 My first enterprise deals

I recently notified all teams that their free ride will be over on June 20th. I should hit $300-$600 MRR by the end of June, with most of that coming as up-front annual payments.

My January self would’ve been ecstatic about this progress. And I am! But these brief moments of ecstasy have quickly been replaced by more ambitious goals.

And therein lies the allure of the endless treadmill.

My promise to myself is that I’ll enjoy the journey towards the next milestone even more than today’s destination.


📈 Launching on Product Hunt

After months of ideating, researching, and building, it’s time to share HelloHailey with the world.

It’s live on Product Hunt!

🤞 Fingers crossed for a successful launch!


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