TaxHabit

We make a tax a game. Tax Habit gamifies prep for freelancers & teen entrepreneur. Score your readiness, build smart habits, and file like a pro (before Uncle Sam finds you).

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Inspiration:

The Failure Before The Spark

In 2019, I launched a tax tech startup with high hopes and all the ambition in the world. I had the credentials, a degree in accounting, over a decade of experience in tax, and a clear vision to help small business owners and entrepreneurs navigate tax season without fear. I raised an obscene amount of money. I felt like I had it all. But despite my best efforts, in 2023 the startup flopped. I poured everything into it, and it still wasn’t enough. The failure wasn’t just financial, it hit me personally. I questioned my instincts, my ideas, and my worth.

I spiraled through a year of false starts, chasing ideas that didn’t stick, desperate to build something that mattered, not just to the market, but to me. When I found Bolt it was like a shock to the system. I had a renewed sense of fight. I knew the problem I was trying to solve was still a problem, I just didn't go about it the right way the first time around. I wasn’t just looking for a hit anymore. I was searching for a redemption arc.

Searching For Redemption

In April 2025, something changed. I started paying attention to the moments that consistently frustrated my clients and community, not knowing what to track, when to do it, or how taxes even worked as a freelancer or a young entrepreneur. They weren’t lazy, they were lost. And I realized, tax software wasn’t solving this. It assumed users already knew what to do.

That was the insight I needed: People don’t need automation, they need coaching, behavior change, and confidence.

What it does

Tax Habit is a gamified tax readiness coach that helps side hustlers, freelancers, and entrepreneurs go from tax chaos to confident prep.

  • Readiness Score – Like a credit score, but for taxes. Track how prepared you are year-round.
  • Smart Habit Coaching – Daily nudges that build lasting tax skills in 2 minutes or less.
  • Learning Modules – Bite-size lessons tied to real behavior, like logging expenses or estimating taxes.
  • Deduction Explorer – Discover what you can write off based on your life and side hustle.
  • Tax Package – Profit and Loss Statement, General Ledger and a completed Schedule C for tax filing.

How I built it

Built with no prior coding experience, I used Bolt’s visual builder, ChatGPT to help with organizing the prompts, Notion to plan and track, Claude integration for smart habit coaching, and prompt-based logic to make the app feel human, educational, and encouraging. This was built entirely inside Bolt with no external dev stack, custom scoring logic, coaching engine, and integrations all run natively in Bolt.

Challenges I ran into

  • Imposter Syndrome – After failing before, hitting “publish” felt terrifying. Every day, I had to choose momentum over fear.
  • Limited Budget – I built Tax Habit for under $150, leveraging every free resource I could find.
  • Learning UX on the Fly – I had to teach myself design principles while building real features.
  • Gamification Logic – Balancing education with motivation required rethinking how to score progress, reward users, and guide them without overwhelm.
  • Keeping It Personal – I wanted it to feel like a coach, not a spreadsheet. That took dozens of iterations on language, tone, and visual flow. -**File Size Limits - After the project reached a certain size I kept hitting snags when submitting prompts, which slowed down the build process tremendously.

Accomplishments that I'm proud of

I'm really proud of the community I was able to build while posting about my progress daily on YouTube and TikTok. I connected with other people building using AI, and people afraid to build but finding confidence watching me do it everyday.

I am also really proud of my effort. Getting up everyday continuing to try when I have every reason not to has rejuvenated my inspiration, and helped me lean into a version of myself I always knew was there even if I didn't always feel it.

What I learned

  • Build what you know and what you need. Unlike before, this time I wasn’t designing a product. I was solving my past self’s tax problems as a service provider. Problems I saw in my clients when they came to me with a mess to clean up.
  • Simplicity wins. People don’t need another dashboard, they need a reason to care and a way to win.
  • Community is fuel. Sharing my build process daily on TikTok and with other founders gave me real-time feedback and accountability.
  • Redemption is earned in reps. Every line of copy, every UX tweak, every bug fix was one step further away from failure and one step closer to proof that I still had it in me. Proof that I am who I always thought I was.

What's next for TaxHabit

I want to take Tax Habit to market. My goal is to run it as a lean, bootstrapped startup with as few employees as possible, staying close to the people I built this for. I want to prove you don’t need VC funding to build something that changes lives, you just need proof it works, a clear mission, and relentless heart.

Here's the plan:

Launch with a paid feature model – Let users have access to all of the features except the Tax Package, that they pay for on an as needed basis.

Use content and community to grow – I’m already showing up daily on TikTok and YouTube. That’s where the education happens, the trust is built, and the users are waiting.

Offer workshops and 1:1 coaching – These services will generate early revenue while giving me a direct line to user pain points.

Build slow, but smart – Every dollar will go back into product development. No fluff. Just focused, sustainable growth.

Prioritize user impact – I’ll measure success not just in revenue but in transformation: Did this tool make someone feel more in control? Less afraid? More ready?

Eventually, I want Tax Habit to be the go-to tax education layer for new entrepreneurs, side hustlers, and teens figuring this out for the first time. Not just another tool, but a coach, a companion, and a quiet confidence boost in a space that usually feels overwhelming.

I failed before. But this time, I’m building with nothing to prove, just something real to offer.

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