Back around 2005, I built a B2B SaaS platform for the legal and mortgage servicing industries while also helping run one of the industry’s larger law firms.

Building Without a Net

There was no engineering team, no product organization, no sales or marketing department, and no outside capital behind it.

There was just me.

I designed and coded the platform, operated the infrastructure, supported customers, handled security reviews, and worked through the realities of selling technology into regulated environments – all while practicing law.

The platform soon became the OS of the business – supporting enterprise customers, clearing multiple security audits, underpinning the firm’s growth to $25M in annual revenue, and eventually becoming part of merger negotiations with another firm.

The Merger

While industry realities required consolidation, I structured the merger transaction so the software platform and intellectual property remained separately owned and licensed.

At the time, I viewed that mostly as practical business structuring. I felt the platform had independent value, and the acquiring firm was primarily interested in our book of business.

Looking back, however, I underestimated what had actually been created.

The platform is still licensed and operating today, twenty years after I originally wrote it, and it has continued to evolve over time.

Originally, the model was true SaaS, where I remained responsible for infrastructure and support. More recently, I negotiated a new agreement with a successor and transitioned the arrangement into passive IP licensing.

The Value Wasn’t the Infrastructure

Over time, I realized the most valuable part of the platform was never the servers, hosting environment, technology stack, or even the patents it once earned.

The real value was durable intellectual property and the ability to adapt its commercial model over time – from SaaS to passive IP licensing – even as the environment around it changed.

Technology changes quickly. Frameworks, hosting models, architectural trends, and development tooling all evolve.

But durable systems that solve real operational problems – and can adapt commercially over time – can continue creating value, even across multiple decades.

Why I Stopped Talking About It

For a long time, I rarely talked publicly about this part of my background.

Part of that was practical. At one point, I needed stable employment, and I found the resume screen doesn’t really have a box for “built and operated a SaaS platform while also building the $25M company that used it” – and, fair or not, there was also a tacit “family business” discount on what we had built.

Hiring managers couldn’t fit my background into their existing frameworks – and I couldn’t get an interview.

So I simplified the story.

I intentionally re-focused on engineering and database roles, re-entered as a mid-level developer, and rapidly rebuilt credibility inside larger enterprise environments where I continue to work today.

That experience has been valuable in its own right. It has deepened my technical skills, broadened my operational perspective, and proved – to both myself and others – I could succeed well outside the (family-owned) environment where I started.

But looking back, I also made a mistake.

I allowed other people’s framing of my experience to shape how I viewed it myself.

Relearning the Value of My Own Experience

Over time, I minimized parts of my background that were actually foundational: building software, operating a business, negotiating commercial agreements, managing regulated technology environments, and evolving a platform that has remained commercially viable for two decades.

I wrote it off as history. Nobody seemed to care, so eventually I stopped caring too.

I no longer believe, however, that authentic leadership means hiding meaningful parts of your own story – or my story.

More importantly, I no longer believe those experiences were things to minimize in the first place.

If anything, they shaped how I think about technology more than almost anything else in my career – not just as code, infrastructure, or delivery, but as long-term business capability.

For years, I thought this chapter of my career no longer mattered professionally.

I was wrong.

— Scott