0 for 1, Learnings From my First Launch Failure

A Postmortem of TaxEstimate.fyi

After building for ~2 months, I launched and abandoned my first project TaxEstimate.fyi within the same week.

I knew from the get-go this would be a learning launch. Though harboring some secret hope it would find success, I was fairly realistic that it would likely flop, and I should strictly time-bound this thing.

Why Spend 2 Long Months?

I kind of intentionally wasted more time than I should have because honestly, building it was novel and fun:

• I hadn’t written front-end code in a decade

• I hadn’t played with ChatGPT/Copilot augmented development yet

• I hadn’t ever done product design to think through a customer problem and crafting a product to solve that

• I hadn’t ever done UI/UX design to think in the eyes of the user

• I hadn’t ever written marketing copy

• I hadn’t ever “launched” anything

• I hadn’t ever played with search-engine-marketing

• I hadn’t ever searched for users

Doing all the above was energizing in and of itself. But eventually I had to face the reality that the “learnings” were more for fun, and not actually bringing me any closer to my goals.

What Went Well

I’m honestly proud of the user experience I built. I set out to create a better tax estimator for myself, and I will definitely be using this for my own tax estimations. Luckily, I built efficiently so it will continue to be hosted forever on free-tier infrastructure.

I also had a few moments of creator-joy for the first time in my life:

• the second customer I showed it to, said with glowing eyes “wow that’s amazing” on two separate occasions.

• heard “very simple and very useful” via email feedback

• heard “I love the detailed breakdowns, Turbotax is terribly surface-level” via email feedback

Though all the above should be taken with a grain of “friends trying to be encouraging” salt.

What Went Wrong

Ultimately, it didn’t solve a pressing enough problem. Tax estimates are hard to do and useful to have. But people won’t pay for something slightly better when there are pre-existing free & adequate solutions (IRS, Turbotax, Smartasset). There’s probably some type of upmarket service that people would be willing to pay for, but the discovery path seems long and hard.

Surprising Learnings

Cool Doesn’t Pay - I’ve heard countless “that’s so cool”, and I impress myself with “that’s so cool” on a regular basis when creating new features. But “cool” is just self-masturbation, and so far away from enough value for someone to pay

Iteration on Bad Ideas is Futile - I knew initial traction was very thin. Only a few potential users found it useful, and none would pay for it. I convinced myself that I could continually make improvements until the whole thing “clicked together”. But that was never going to happen.

The Web Can Be a Silent Void - I had some grandiose expectations that posting to HN and reddit would kickstart my user base, or at the very least start a discussion. But both were met by crickets. I’ve realized, to work, these types of posts need to be really sexy in their own right or backed by a strong pre-existing audience who trusts your sexy brand. Going to start building my personal entrepreneur brand.

What’s Next

Follow The Money - I approached my first product far too idealistically. I had all these good-sounding prerequisites that I now realize were naive:

• unique passion for the product—I’m most passionate about fun things like bouldering or snowboarding, hard to build an enterprise SaaS out of those

• hasn’t been done before—probably because it’s a bad business, it’s unlikely I’m building the next ChatGPT from my laptop

• very low overhead—means my product won’t provide much value

• solves my own problem—all my own problems are just low-value consumer annoyances

My next project is going to tackle higher value problems that people are willing to pay for.

B2B - Really want to do B2B rather than B2C. It’s higher barrier to entry because I don’t know B2B needs as well, and I have fewer natural acquisition channels. But it’s probably worth it because it really sucks begging consumers for my $5 app.

Validate Even Faster - No more “playing entrepreneur house”. It was fun lying to myself and pretending to be building something useful. But it’s time to be more ruthless and not waste time on a “fun idea”.

Hope you guys found this useful or entertaining. Any thoughts or things I missed? Let me know in the comments below!

P.S. I recommend watching Alex West’s YouTube video on business ideas. I fell for every one of the pitfalls he mentions. He really captures exactly where I’m at in the “learning from failure” process.