Entrepreneurship was always somewhere in the back of my mind.
My grandfather was an entrepreneur. He owned and operated several small retail stores and was always trying something new. Growing up around him, I regularly heard some version of, “You should run your own business.”
Instead, I found my place in corporate America.
I spent 25 years working in technology, first on the technical side and later in sales, where I spent roughly 15 years. I spent more than a decade at Microsoft, eventually leading its U.S. enterprise business across sports and entertainment.
It was a great run.
Microsoft opened doors for me. I met some amazing people, built relationships that continue today, and had my two children while I was there. It gave me opportunities I never could have predicted when I started my career.
It also helped prepare me for what I wanted to build next.
Relationships outlast roles
Large companies teach you how to work with all kinds of people. You work across teams, reporting structures, personalities, priorities, and incentives. You learn quickly that having authority over someone isn’t the same as having their support.
Relationships are what make the work move.
That includes the people who report to you, the extended teams around you, your customers, and the people you meet along the way. Many of the relationships I built during my corporate career have carried into what I’m doing now. We still collaborate, share ideas, make introductions, and look for opportunities to work together.
I was probably more naive about this earlier in my career. I assumed most people were trying to do what was best for the company, the team, or one another. Over time, I learned that people have their own ambitions, interests, and incentives.
That doesn’t mean you stop trusting people. It means you become more deliberate about who you build with.
You need a circle of people who can get things done together, trust one another, and genuinely celebrate shared wins. Sometimes you have to take a chance on people. Sometimes you get burned. That’s part of building the right circle.
Growth eventually runs into the boundaries of the system
Sales is interesting. You can have a great year, and your reward is usually a higher quota.
That isn’t a complaint. It’s how the system works. But it creates a constant grind, especially after you’ve captured much of the opportunity within your existing role.
During my time leading Microsoft’s sports business, we achieved significant growth. Eventually, I believed the next opportunity required a broader mandate and a willingness to approach the market differently.
I made the case for taking on something larger. The idea received attention from senior leadership, but it didn’t move forward.
That experience taught me something important about large organizations. They have real constraints. Leaders are balancing risk, competing priorities, internal structures, and the needs of thousands of employees. Even a strong idea can stall when it doesn’t fit the organization’s direction or structure.
I wanted to keep building. If I couldn’t build the next thing inside Microsoft, I was eventually going to build it somewhere else.
The right amount of process depends on the risk
When you work at Microsoft, you live inside its ecosystem. You learn its tools, forecasting, product reviews, contracting, security requirements, and legal processes.
Much of that structure exists for a reason. If an enterprise customer can’t access its cloud infrastructure, the consequences can be serious.
But not every business carries that level of risk.
The consumer apps I’m building today don’t need the same machinery as an enterprise cloud platform. If someone’s water tracker has a problem, that matters, but it isn’t the same as a global company losing access to critical systems.
Becoming a founder required me to unlearn some of the weight that comes with operating inside a huge company. I still value discipline and good judgment. I’ve just learned to match the process to the actual risk.
A smaller company has to move. You make the best decision you can, create fair terms, get the deal done, learn, and adjust.
AI changed who gets to build
The leap into entrepreneurship became practical for me because the tools changed.
AI has made technical people more technical. More importantly for someone like me, it has allowed business-minded and outcome-focused people to become technical builders.
I spent years in highly technical rooms. I wasn’t always driving those conversations, but I participated, listened, asked questions, and learned how technology decisions get made. That experience matters now.
I don’t need to pretend I’m the strongest engineer in the room. I need enough understanding to direct the work, question decisions, evaluate tradeoffs, and recognize whether we’re building something useful.
People talk about “AI slop,” and some of that criticism is deserved. But AI-assisted work isn’t automatically low quality. The outcome still depends on the person directing it, the standards they apply, and whether they’re solving a real problem.
In five months, I launched four apps, with two more on the way. Building them through traditional consultancies could easily have required six-figure investments for each product. Instead, I’ve been able to move from an idea to a working product on my phone, sometimes in less than 24 hours, using the AI tools I already subscribe to.
That speed changes everything.
I can form an idea, build it, test it, learn whether people want it, and change direction without betting the entire company on one decision. As a solo founder, I can touch every part of the business: product strategy, code, design, websites, creative, SEO, go-to-market, and social media.
I’m still a one-person company, but AI gives me leverage across nearly every part of the work. An individual builder has never had access to this level of capability, speed, and reach.
Success looks different when you own the outcome
For years, success was measured through revenue, quotas, growth, and the size of the business I managed.
Those things still matter. I’m building a business, not a hobby.
But success now also means spending more time with my family. It means carrying less stress and choosing what deserves my attention. I can learn fast, fail fast, pivot, and try something different.
There’s freedom in that.
Large companies have to create standards and ask people to operate within them. When you employ tens of thousands of people, you don’t have much choice. I learned how to succeed inside that kind of system, but I also regularly felt that some of my ideas were being contained by it.
Now I make the calls, and I’m responsible for the results.
That responsibility is real. I walked away from a very comfortable career, and everything that comes into this business is now on me. I expected that to create more anxiety than it has.
My faith is a major reason it hasn’t. I’m at peace with the decision, and I believe God is guiding what I’m building. The risk didn’t disappear. I just don’t feel controlled by it.
There may never have been a better time to try
If you’ve spent 20 or 25 years building a corporate career and keep feeling pulled toward entrepreneurship, take that feeling seriously.
You don’t have to quit tomorrow. But take one of your ideas and see how far you can push it.
If you’ve been thinking about making the leap, the tools have never been more accessible. If you’ve been laid off and are struggling to find your way back into the same system, this may be an opportunity to build something of your own.
Your career experience isn’t baggage. It may be the judgment, perspective, and network that allow you to use these new tools well.
Take an idea. Build something. Put it in front of people.
See how far you can take it.