Founder Keith McCall on building companies, software, and real-world execution.
I need to say something blunt to founders: Some of you are sabotaging yourselves with terrible slides. I was incredibly clear beforehand: ONE slide. That’s it. My recommendation: - A strong photo of yourself - A QR code people can scan - Minimal text - Guy Kawasaki simplicity
When you walk into a room full of entrepreneurs and investors, pay attention to the host. Specifically: Watch who the host hugs.
In 2008, the Seattle Seahawks went 4–12—a team with talent, history, and expectations… that simply wasn’t working. In 2004, I built my first real company—Azaleos—in Redmond. Redmond made sense. Close to Microsoft. Close to talent. Close to the center of gravity for enterprise software at the time. But by 2007, something shifted—not in our business, but in where energy lived. Microsoft lost focus on partners. So we moved to Seattle: South Lake Union.
I just read “Why ADHD Is the Cheat Code of the AI Era” by Brian Sugar — and it hit. For years, corporate systems were designed to suppress ADHD, not leverage it.
Across every stage—angels, family offices, venture—the real question is the same: Who is the person that will lead this company, 3 to 5 years from now? Who can scale, navigate pressure, and drive to an outcome—acquisition or IPO? That’s not a model. That’s judgment.
It starts with a spark. A founder or founding team sees something that could change the world for the better: * a problem that shouldn’t exist * an opportunity no one is executing on * a timing shift the market hasn’t caught up to That’s the spark. But a spark doesn’t last. So you build structure.
Every founder hears it, especially from inexperienced angel investors, or from angels who are patent lawyers (they want your business). “You should patent that.” Most don’t understand the mechanics—or the strategy. The strategy counts.
It’s exciting. Fast. Meaningful. You’re building something from nothing. But the moment someone actually considers leaving a stable role at a large company, the thinking shifts—fast.
Someone new connects with me on LinkedIn every single day. And I usually accept. Why? Because I’m building a community—people who want to see what my portfolio companies are doing, learn from it, maybe even contribute to it.
This week, a question forced a reset: “What wouldn’t you do?” Not what I should do next. What I would stop doing entirely.
I’ve been doing this for over 30 years. There are a lot of stories, a lot of mistakes, a lot of things that actually worked… and most of it just sits in my head. That doesn’t feel right. So I started trying to write a little more. Not because I love writing—I don’t—but because I feel like I should be giving something back at this point.
I remember driving from Washington into California with my younger son—wildfires burning along the way. We were visiting schools. He was figuring out his path. I was doing what I always do—building the playlist before we went, and adding to it as we went. We ended up at University of California, Santa Cruz.
And along the way, I’ve learned something that doesn’t get talked about enough: Reputation isn’t built when things are going well. It’s built when things get uncomfortable.
One of the most interesting policies I’ve seen comes from Esri. They cap gifts at around $25. Anything beyond that gets refused. At first glance, it feels rigid. In practice, it’s clean.
At first glance, “OG” sounds like it means old guy. That’s not it. OG = “Original Gangster.” The term came out of West Coast hip-hop—most notably Ice-T’s O.G. Original Gangster. It wasn’t about age. It was about credibility earned the hard way.
Almost every day, I get the same two messages: “We can help you outsource your development.” “Would you consider an offshore team to scale faster?” My response is always the same: We don’t outsource. Period.
The belief model matters more than most founders think. I started my first company before I even left Microsoft. Enough time has passed that I can probably admit that without getting in trouble. In 2003, about a year before I left the Microsoft Exchange team, I intentionally took responsibility for relationships with venture capitalists. That gave me a window into a world most entrepreneurs only see from the outside. In the lead-up to Microsoft’s acquisition of Groove, I spent time with people from Sequoia, Benchmark, Accel, and others across the Valley trying to align their portfolio companies with Microsoft. I did the job. But that wasn’t the real purpose.
During COVID, getting to Chile wasn’t a trip. It was a commitment. My wife and I flew into Santiago, got tested, and waited 24 hours in a hotel. If positive? Five days in quarantine. We got lucky.
Most founders think incorporation is the milestone. It’s not. It’s the starting line.
A perspective on capturing moments, experiences, and life context in ways that persist beyond memory.
Lessons from early web infrastructure, proxies, and systems thinking that still apply to building companies today.
A practical perspective on leadership, accountability, and building companies with clarity under pressure.
Founders win by turning urgency into disciplined execution rather than mistaking noise for progress.
Leadership is tested through execution, alignment, and how quickly a team can move together.
A grounded view on venture capital, timing, and what fundraising does and does not solve inside a startup.
Execution is where intent either compounds into value or disappears into delay.
Resilience is one of the most important operating assets when outcomes resist expectation.