Show Me The Money: What we made, what we spent, and what we learned for next time

Over a couple of quarters, I bootstrapped my first software business — SnapFile — with a co-founder. We built software to help small business owners file their BOI Reports under the new Corporate Transparency Act. The product worked, people paid us, and we even had repeat customers. But by the end, we had to shut it down thanks to legal and regulatory curveballs we couldn’t control. We ended up being unprofitable, which isn't what we expected but is normal for a first time business.

This post isn’t about the product or the shutdown (that’s over here). This one’s about what we spent money on, what we got right, and what I’d change next time.

1. Legal Setup Was a Bigger Time / Money Sink Than I Expected

Early on, I filed in the wrong state. That meant dissolving, re-filing, redoing bank accounts, redoing EINs, and generally spending too many hours fixing something that didn’t move the business forward.

And that was before figuring out how to stay in compliance — one-off filings, annual reports, registered agents, and sooo much more. Every entity you spin up adds a new to-do list. That’s fine when you're making money — not so much when you’re still testing if something works.

💡 Next time: one LLC in my home state with a flexible name, and I’ll use DBAs for any offshoots. Much easier to experiment without all the admin baggage.

2. Marketing: Small Tests Paid Off, Eventually

We spent a little bit in a lot of places: Google ads, email lists, LinkedIn ads, TikTok and Instagram experiments, and some SEO work. I’m glad we didn’t go big early — especially since most of it didn’t work.

Google Ads in particular felt like a black hole. We didn’t spend a ton, but it was clearly designed for pros running large campaigns. It’s just not built for small businesses with little budgets and tiny streams of data.

Where we eventually got traction was with businesses — CPAs and lawyers — who needed to file dozens or even hundreds of reports. Our direct-to-consumer efforts weren’t wasted, but the real opportunity was in bulk filings. We just didn’t discover that early enough to go after that market aggressively.

💡 Next time: experiment with small dollars across platforms, see what works / doesn’t, and keep pivoting. For B2B, consider some more obscure opportunities like industry newsletters.

3. Doing the Work Ourselves Was the Right Call

We didn’t outsource much. Friends pitched in for free and for money, and we paid lawyers to get our business structure in order. But most of it — product, support, marketing, backend — we did ourselves.

That wasn’t just about saving money (though we definitely did). It gave us tight feedback loops and let us move fast. Had we spent more on contractors or agencies, I think we’d have learned less, moved slower, and definitely lost more money.

💡 Next time: same approach. Use freelancers where critical, and only once I know exactly what I need.

4. We Kept Our Software Stack Lean

All-in, software and admin tools made up less than 15% of our total spend. We used Vercel, Stripe, Webflow, Sendgrid, and a few low-cost AI tools to get the job done. Nothing fancy. We paid monthly when possible and canceled anything that wasn’t essential.

I think this is one of the underrated advantages of modern bootstrapping — you can go surprisingly far without a big bill. Also, you become fluent very quickly in super important technology that changes constantly… because you have to.

💡 Next time: stay scrappy here. It’s not about having the best tool, it’s about having the lightest tool that works.

5. We Made Real Money — But Then the Law Changed

This part still stings. We had momentum. People were finding us, paying us, coming back to file more reports. And then we hit endless legal and regulatory challenges in our little industry.

Almost overnight, our market froze then shrank by 99%. Not because our product was bad. Not because customers didn’t want it. Just extenuating circumstances.

We had structured pricing to match the flow of filings — usually collecting revenue only once the customer completed everything. That meant a long delay between someone signing up and us getting paid, especially with larger customers (their business was basically bookings). So when enforcement paused, that future revenue vanished.

💡 Next time: be careful tying a business directly to a new law. Especially one where the rules might shift midstream. We knew this was a risk, but it was a higher risk than we realized.

What I’d Do Differently Next Time

• Start with one legal entity, keep it flexible, and avoid re-filing messes
  
  
• Run lean, structured marketing tests — but test B2B early in addition to B2C
  
  
• Outsource only when clear on the scope and needs
  
  
• Stay skeptical of opportunities tied to government enforcement
  
  
• Use the simplest, cheapest stack that does the job
  
  

It’s frustrating to close down a product that had some traction, but I don’t regret the experience. We actually built something! And Launched it! People paid for it! I learned more than I could’ve by reading another startup blog or taking another course.

And next time — because there will be a next time — I’ll be a lot smarter.