What I'd Do Differently If I Were Building My First SaaS Again

I spent nearly a decade building my telecom expense management SaaS from zero to eight-figure revenue and a successful exit. Along the way, I made every mistake in the book — and a few that aren't in any book yet.

If I could go back to day one with everything I know now, here's what I'd change.

I'd Validate With Revenue, Not Conversations

My first mistake was spending too long in 'discovery mode.' I had dozens of conversations with potential customers who said they loved the idea. But love doesn't pay invoices. I should have put a price on the table within the first month and let the market tell me the truth with a credit card.

The fastest path to product-market fit isn't more interviews — it's a landing page, a price, and a deadline.

I'd Hire a VP of Sales Before I Thought I Was Ready

I was the sole seller for far too long. I told myself the product wasn't ready for a sales team, but the truth was I was afraid of letting go of the thing I was best at. The moment I hired someone who could sell as well as I could, revenue doubled in nine months.

If you're a technical founder doing all the selling, you're the bottleneck. If you're a sales-minded founder doing all the selling, you're still the bottleneck.

I'd Pick a Smaller Wedge

We tried to be everything for everyone in telecom expense management from day one. It took us three years to figure out that our best customers were mid-market companies with 500-2,000 mobile lines. If I'd started there — just that segment, just that use case — we'd have hit $1M ARR two years sooner.

I'd Invest in Systems Earlier

For the first three years, we ran on spreadsheets and heroics. Every customer onboarding was a custom project.

Every report was manually generated. When we finally invested in building real systems — automated onboarding, self-serve reporting, proper CS tooling — our margins went from 40% to 72% almost overnight.

The founders who build systems early don't just scale faster. They build more valuable companies.

I'd Raise Less Money and Keep More Equity

We raised capital when we didn't strictly need it because it felt like validation. But every dollar of outside capital comes with expectations, timelines, and dilution. I would have been better off bootstrapping to $2M ARR and then raising a smaller round at a much higher valuation.

The Bottom Line

Every founder's journey is different, but the patterns are remarkably similar. The mistakes I made aren't unique — I see founders making the same ones every week. That's exactly why I do what I do now: to help founders skip the three-year lessons and get to the inflection point faster.

If any of this resonates, let's talk.

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