Greg Head
I work with 45+ bootstrapped SaaS founders every month and see what’s actually working across dozens of real companies — in real time.
I run Practical Founders CEO Peer Groups. I host the Practical Founders Podcast. And I’ve spent 30 years building and scaling software companies — including two that grew to $100 million in revenue and one that went public.
But what matters most is what I’m doing right now: helping bootstrapped SaaS founders make better decisions as their companies grow. This is my main work.
What I Do Today
I work with about 45 SaaS founders each month in small, curated peer groups.
These are bootstrapped or lightly funded founders, typically with $1M to $20M in ARR, who are building valuable software companies without big VC funding.
We focus on one thing: helping founders make better decisions as their companies grow.
Not theory. Not content. Real decisions — every month.
Hiring key leaders. Changing pricing. Pushing for growth or staying profitable. Navigating AI. Thinking about selling — or not.
Every month, I’m in the room when these decisions get made. That’s where the patterns become clear.
What I See Working (and Not Working)
Working closely with dozens of SaaS founders every month — and hundreds more through the podcast — I see patterns in real time.
What’s Working
- Founders who pick a focused market and own it — vertical SaaS with clear positioning
- Strong retention and revenue quality over raw growth
- Thoughtful AI adoption inside the product and team
- Steady, compounding growth — 20–60% annual growth sustained over years
What’s Not
- Chasing tactics without strategic context
- Over-hiring before the revenue justifies it
- Forcing growth at the expense of profitability
- Making big decisions without enough perspective
Why I Started Practical Founders
Here’s Why I Do This — When I Don’t Have To
I’ve built companies. Taken one public. Won some. Lost some. I don’t need to do this. I do this because I’m sick of the perception that VC funding is the game for software founders. It’s not. For most founders, it’s a rigged game with bad odds.
I do this because I love working with serious, practical founders who are solving real problems with their products and companies.
I do this because I learn something every week. The real patterns — the stuff that doesn’t show up in books, blogs, or AI chats.
And I do this because growing a company is a human game. It’s harder than it looks, but it’s completely possible. Founders just shouldn’t have to figure it all out alone.
Practical Founders Podcast
I’ve interviewed 150+ SaaS founders who have built and often sold valuable software companies — most without big funding. Together, they’ve created over $11 billion in founder equity.
These aren’t the usual startup stories. They’re practical, real-world examples of how companies actually grow, scale, and create wealth for founders.
What I Believe About Building SaaS Companies
- You don’t need VC funding to build a very valuable software company.
- Most success comes from avoiding big mistakes, not making perfect moves.
- Revenue quality and retention matter more than growth hype.
- Vertical SaaS and focused businesses win long-term — for founders.
- Founders should have control, options, and time — not just growth pressure.
- AI creates real opportunities and real challenges — and most SaaS founders aren’t moving fast enough on either.
There’s more than one way to build a valuable software company. This is the practical path.
How I Work With Founders
CEO Peer Groups (Primary)
Small, curated groups of SaaS founders working through real decisions together every month. This is my main focus — and where I spend most of my time.
1:1 Advisory (Limited)
Intense deep-dive work with individual founders who want to focus in and move fast. Limited availability.
A Bit About Me
I prefer depth over scale. I’d rather work closely with 50 serious founders than loosely with 500. I split my time between Southlake, Texas, and Park City, Utah. I’ve been married 30+ years. My kids are grown. I’ve built the kind of life that lets me do work I care about, with people I respect, on my own terms.
That’s the same thing most of the founders I work with are trying to build — a company and a life that work together.
If This Approach Resonates
If you’re building a SaaS company and making important decisions every month, you don’t have to do it alone.