Kevin Wagstaff

Founder, operator, investor.

I co-founded and sold a software company. Now I invest, advise, and spend an unreasonable amount of time trying to get good at golf.

More about me

ABOUT

Still curious. Still starting over.

I’m Kevin Wagstaff. I co-founded Spectora with my brother and spent eight years building it into the home inspection industry’s leading software — bootstrapped from zero to a $100M+ exit.

Before any of that I was a basketball player. High school, college, then a short stint playing professionally in the Philippines — which, as a Filipino kid from Colorado, was challenging and incredible to see where my family came from.

These days I invest selectively, look for businesses to get involved with, and I’m building a golf community called LOGO Golf Club. I found golf late (at 41) and it has taken over my life.

Don’t worry, I lost the man bun

Founder

Operator

Investor

Advisor

Bootstrapper

Former Athlete

THE PATTERN

I keep starting over on purpose

At 30 I quit basketball — the thing I’d been great at my entire life — and started playing grass volleyball. Then beach volleyball. From scratch, with no experience, as the worst player on every court I stepped onto.

I loved it.

Being brand new at something made me feel vulnerable and driven to improve, and that turned out to be the most motivating feeling I know.

So I went all in: lessons from multiple coaches, relentless practice, played every chance I could. Ten years later I was competing at an Open level in Denver and placing high in tournaments.

Then in 2025 I picked up a golf club, and the whole thing started again.

It’s the same pattern every time:

Be willing to be bad at something publicly, then do the work almost nobody else is willing to do. That’s how I built a company, and it’s how I’ve approached every endeavor I’ve ever cared about.

It’s the same pattern every time:

Be willing to be bad at something publicly, then do the work almost nobody else is willing to do. That’s how I built a company, and it’s how I’ve approached every endeavor I’ve ever cared about.

WHAT I’VE DONE

The work.

1998–2014

Basketball

High school, college, then a short professional stint in the Philippines.

Read the clippings

2014–2026

Beach Volleyball

Started from zero at 28. Ten years later, got to Open level locally.

2008–2017

Finance & Tech jobs

Learned how to invest at Charles Schwab & how tech companies operate at HomeAdvisor/Angie's List.

2017–2024

Spectora

Co-founded with my brother. Bootstrapped to the category leader in home inspection software, then a $100M+ exit.

2025–now

What’s next

Investing, advising, LOGO Golf Club, and a golf obsession I can’t explain.

Good things get built with good people. Our Spectora team when we stepped away.

WHAT I’M DOING NOW

Three things, and one of them is golf

BOARD & ADVISORY

Businesses I actually want to be around

I’m looking for companies to get involved with at a board or advisory level — golf, live house music experiences, and SaaS. The last because I spent a decade there and know where the bodies are buried. The first two because it doesn't feel like work.

INVESTING

Selective, and honest about it

Small checks in a small number of places. I’m more useful as someone you can call than as a line on a cap table.

LOGO GOLF CLUB

For people who found golf late

I picked up a club at 41 and it rearranged my life. LOGO is for everyone in the same boat — built for fun, with no particular plan for it to become anything else.