Why We Bootstrapped Our Private Beta

When we first began sharing the concept behind Levelup, we expected the core value proposition to center around valuation. We believed that helping small businesses track, understand, and grow their valuation would be a breakthrough offering—something both owners and advisors could rally behind.

But in our early conversations with investors, we noticed something surprising: the valuation angle was contentious.

Some were skeptical of applying valuation models to messy small business data. A few even pushed back on whether valuation was something business owners actually wanted to hear about in real time.

So we listened—and pivoted.

We quickly realized that the more universally useful part of our platform wasn’t the valuation output itself, but rather the financial intelligence layer underneath it: the ability to standardize data, clean up the chart of accounts, visualize KPIs over time, and create clear, comparable insights across entities.

That became the foundation of Levelup—and the reason we decided to bootstrap our way through the private beta.

1. Excitement Isn’t the Same as Conviction

From day one, the idea behind Levelup generated strong interest. Advisors, operators, and even early-stage investors were intrigued. We heard things like “I’d absolutely use this” and “This is something every small business needs.”

But Jon and I knew that early excitement doesn’t always translate into conviction—especially when you're building something as technically ambitious as Levelup.

Despite having built 14 software tools together—including a proprietary CFO platform we used inside our accounting firm—we understood that we didn’t look like traditional “technical founders” of a complex financial SaaS startup.

We didn’t want potential investors to have to imagine what we could do. We wanted to show them what we’d already built.

2. We’ve Had Exits Before—But This Time, It Was Personal

We’ve been in this space for a while. Jon and I have had three successful exits. We’ve built services businesses, productized internal tools, and scaled software to acquisition.

But Levelup felt different. The stakes were higher—not just technically, but emotionally.

We weren’t trying to solve a niche operational problem. We were trying to rethink how small businesses and their advisors interact with financial data. And that meant building:

We didn’t want to raise capital just because we had experience. We wanted to earn it by building something real—again.

3. Two Weeks in Costa Rica: Building, Testing, and Team Vision

As we started building Levelup, we knew that success would require more than just a good idea and two committed founders. We needed to prove the core tech—and figure out how to attract the kind of world-class team that could take it to the next level.

So we flew to Costa Rica and dedicated two focused weeks to solving both challenges.

We set up shop in an Airbnb and divided the work. I went deep on the AI component—building, testing, and refining prompt chains that could turn messy small business financials into standardized, structured intelligence. I ran hundreds of test cases, iterated on logic, and worked to ensure the model produced consistent, high-value output.

Jon focused on the technology foundation—thinking through how we’d structure the app, manage the data pipeline, and scale the product with performance and flexibility in mind. But he also zoomed out.

He spent hours searching for talent across the globe—reviewing portfolios, reading GitHub histories, studying architectural decisions from other modern SaaS platforms, and asking one core question: What kind of team do we need to build something truly great?

That trip wasn’t just about building software. It was about pressure-testing the entire vision—product, people, and platform. We came back not only with working prototypes, but also with clarity on what kind of company we wanted to build.

4. Bootstrapping Gave Us Focus, Not Limitations

We worried that focusing on raising capital would introduce pressure that had the potential to pull us away from the actual problem we're solving. We had spent time in earlier months optimizing pitch decks, growth projections, investor milestones—not exploring actual product-market fit.

By bootstrapping, we removed that noise. There were no board meetings, no growth metrics to focus on, no pressure to sound “big” before we were ready. Just real work on a real problem.

We could talk to potential users, build prototypes, test features, and iterate quickly without the added pressure.

5. We Wanted to De-Risk the Investment—For Everyone

We believe in capital. But we believe in taking that capital responsibly.

If someone’s going to back us, we want them to do so with eyes wide open—understanding the opportunity and the execution.

Bootstrapping allowed us to:

When we raise, we want to come to the table with traction, not theory.

6. We Built the Foundation Ourselves—And It Shows

One of the most valuable outcomes of bootstrapping was that we stayed incredibly close to the product.

We didn’t delegate our way through development. We wrote the queries, designed the normalization logic, iterated the UI, and handled bug identification and resolution ourselves. We're also incredibly close to the sale and the customer support process at this early stage.

That intimacy helped us avoid waste and spot insights early. We can see exactly where users are getting stuck. We have identified which outputs aren't resonating or where navigation doesn't make sense. Bootstrapping has given us craftsmanship, clarity, and control.

7. Bootstrapping Got Us Here—Now We’re Ready to Raise

We didn’t bootstrap because we were against raising capital. We bootstrapped because we wanted to earn it.

Now that we’ve validated the technical core, built a working private beta, and clarified our go-to-market strategy, we’re preparing to raise our pre-seed round, starting conversations in August and targeting a close in October.

This next phase of capital isn’t about scaling prematurely—it’s about finishing the product, bringing in a few key hires, and launching our public beta with discounted pricing for early adopters.

But we’re not raising just to raise. We want to be extremely selective about who we bring on as investors.

We’re looking for true capital partners—people who are emotionally invested in our mission, who believe in the impact of financial intelligence, and who see what we see: that helping small businesses make smarter financial decisions can reduce failure rates, unlock economic mobility, and change lives.

This isn’t just about building a product—it’s about creating a platform that makes small businesses stronger, more resilient, and more successful.

We want to change the world. And we want investors who are ready to help us do that.