#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head

As the year winds down, I want to share an end-of-year message for practical SaaS founders who want to make better progress in 2026. Based on my recent conversations with more than 40 CEOs in my Practical Founders peer groups, it’s clear that growth rates alone don’t define whether it was a “good” year. Founders experienced very different outcomes—and very different feelings about them.

In this episode, I walk through five practical questions I believe founders should ask as they look ahead to 2026 (or their next quarter). These questions focus on whether you’re working on the right hard things, what you’re deliberately changing next, what help you actually need, whether you have enough cushion in the business, and the story you’re telling yourself and your team about progress.

This isn’t about templates, quick-fixes, hype, or perfect planning. It’s about making steady progress on the hardest, most important things in your business—while staying independent and resilient. 

Success isn’t final and failure isn’t fatal. What matters is whether you keep going—and keep making progress. If you’re still here, still building, still learning—you’re doing something right. I respect practical founders who choose independence, solve real problems, and do hard things year after year.

Key Takeaways

• Progress Over Growth Rates - What matters is whether you moved the hardest, most important parts of your business.
• Focus Is a Force Multiplier - Trying many things without concentration is why most initiatives stall.
• Companies Mirror Their Founders - The company’s strengths and weaknesses often mirror the founder’s.
• Cushion Creates Resilience - Cash, energy, and upsides protect businesses when headwinds inevitably appear.
• You Make It Up - How you frame last year’s results shapes decisions, morale, and alignment.

Quote from Greg Head, founder of Practical Founders

“Everybody's doing really hard things who are practical startup founders. I know you are too. The question isn't about what the perfect growth rate or planning process is for you right now. The question is, are you lined up to actually do enough of the most important hard things in your business next year?

Are you really set up to make the kind of progress you want along the bigger vision you have for the company? There are all kinds of ways to do it. You can go fast or slow, or it could be an invest year, a rebuild year, or a steady year. You can choose your growth rate, your profitability, and all of that. 

“You get to do it your way. You've bought your independence, or you are paying for it the hard way. There’s no one right way to do all of this, if you're making big progress and getting better every year in the eyes of your customers, employees, and the owners.”

Links

• Greg Head on LinkedIn
• Practical Founders on LinkedIn
• Practical Founder website

Podcast Sponsor – Cypress Growth Capital

This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company’s future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/

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