About Jake

I’ve been building things with technology for more than 25 years.

My journey started in 1988 when I got my first computer, an Epson Equity 1+ with an 8088 processor, 640K of RAM, a tiny hard drive, and a stack of manuals for MS-DOS and GW-BASIC. Like many kids who grew up around computers in the 1980s and 1990s, I was fascinated by the idea that you could create something from nothing with a keyboard and a little imagination.

That curiosity never really went away.

Over the years I’ve worked as a software engineer, architect, CTO, CIO, Chief Innovation Officer, Vice President of Technology, founder, inventor, consultant, and mentor. I’ve helped build ecommerce platforms, ticketing systems, data products, cloud platforms, integrations, automation systems, and AI-powered solutions. Along the way I’ve contributed to patented technologies, helped scale companies, built and led engineering teams, and spent time working directly in data science and machine learning long before AI became the topic of every conversation.

One of the things I’ve learned after watching multiple technology cycles come and go is that the technology itself is rarely the hard part.

The hard part is solving real problems.

The organizations that succeed are usually the ones that can connect people, processes, and technology into systems that actually work. That belief has shaped much of my career and eventually led me to start Transcendent Software, where I’ve spent years helping organizations modernize operations, automate workflows, integrate systems, and build practical technology solutions.

Most recently, I spent several years helping build and lead technology organizations at TFL, where I was responsible for growing engineering teams, expanding technical capabilities, investing in data and automation initiatives, and helping the company build software products and platforms to support future growth. It was an important chapter in my career and one that reinforced many of my beliefs about leadership, technology, and building strong teams.

Today my focus is on the next chapter.

I’m investing my energy into Transcendent Software, CoffeeBreak, and a collection of projects that sit at the intersection of software, AI, automation, and human creativity. CoffeeBreak is my vision for practical AI orchestration, helping organizations coordinate AI, tools, workflows, and human review to accomplish meaningful work. I’m also spending time exploring Open Jibo, an effort to bring new life to a beloved robot platform that still inspires curiosity and creativity years after its original company disappeared.

This site is where I share what I’m learning along the way.

You’ll find thoughts on software engineering, AI, entrepreneurship, leadership, automation, technology trends, and the challenges of building products and businesses. Some posts are technical. Some are strategic. Some are simply reflections from someone who has spent decades watching technology evolve and trying to understand where it might be headed next.

Outside of technology, I enjoy life on acreage outside Kansas City, spending time with family and friends, gardening, BBQ, live music, golf, and cheering on the Chiefs and Royals. I’m a musician at heart, with guitar being my first creative outlet long before software became my profession.

You may also notice a fedora appearing from time to time.

That started years ago as a nod to Indiana Jones and a fascination with classic Americana. For a while it became part of my identity and even found its way into logos and branding. These days you’ll usually find me in a trucker cap instead, but the fedora occasionally shows up as a reminder that curiosity, adventure, and a willingness to be a little different have always been part of the journey.

If something I write resonates with you, I’d love to connect.

After all these years, I’m still learning, still curious, and still building.

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