E39: Jack learns about Tech Debt
In this episode of the SAAS Operators, we go from HVAC techs to stablecoins to tech debt, the question is the balance between speed to market and borrowing from the future. The trades, like HVAC techs, are winning because real work still needs to get done. Zach explains about how he's running ads for his brothers home services business, and says it’s basically shooting fish in a barrel. If he ever moves to the jungle he's turning into a media buyer. Then we talk about 2026, how building is getting cheaper, teams are getting smaller, and the bar is moving. Taylor Holiday describes stablecoins as contribution margin tech because traditional rails, wires and card fees are stuck in the Stone Age. The conversation closes on velocity and speed of change. How most decisions are two way doors, and why Jack believes shipping more, worrying less, and how “doing it right” kills momentum. But let's be honest, Jack's still learning about tech debt.
In this episode of the SaaS Operators Podcast, we map out what’s actually going to matter in 2026, without the fluffy prediction nonsense.
We start with HVAC techs and end up in stablecoins, tech debt, and AI turning execution into fast forward. Same point the whole time: reality wins, and the people who ship win.
The Trades Don’t Care About Your Roadmap
You hear a story about an electrician quoting $40,000 for two days of work.
Not because it’s funny. Because it’s true.
Some problems are physical. They have to get fixed. There’s no “we’ll circle back in Q2.”
That’s why trades keep getting more lucrative. Real demand, limited supply, urgent outcomes.
And then there’s the kicker: running ads for home services can feel like shooting fish in a barrel.
Simple offer. Clear intent. Basic marketing competence. Leads show up.
If you’ve ever wanted a boring business that actually works, that’s the pitch.
2026 Feels Like Payoff Season
2025 felt like a heavy execution. Not necessarily emotionally brutal, just hard work and lots of moving pieces.
2026 feels different. More answers, fewer mysteries. Repeat what works, and you get compounding results.
The last couple years have been rough for most businesses since mid 2022. There’s a sense the pressure is easing, even if it’s not “easy” yet.
“Most Businesses Fail” Isn’t a Useful Thought
You can say “most businesses fail” and feel smart.
But it’s a garbage stat if you don’t define “business.” Cupcake stores, side projects, random Delaware LLCs, all in the same bucket.
The better point is capital requirements are falling fast.
It’s cheaper to build, cheaper to keep something alive, and small teams can do way more than they used to. That means more businesses will exist. Some will win big. Some will quit. Some will just quietly print.
Stablecoins Are Boring, That’s Why They’re Interesting
Stablecoins come up as the rare crypto thing that isn’t trying to cosplay the future.
The pitch is simple: payment rails are outdated, and stablecoins are basically contribution margin tech.
And you don’t need to believe in crypto religion to agree that wires are insane.
You can’t send a wire on Sunday.
Sometimes you can’t send one after 4pm.
You send it Friday and it clears when it feels like it.
That’s not “how money should work in 2026.” That’s a museum.
Even if stablecoins only replace wires, that’s a real change.
Marketing Is Moving From Opinions to Orchestration
They hit a point that matters if you run paid social or build anything creative:
Formats keep expanding. Nothing replaces anything. It just stacks.
AI UGC isn’t a silver bullet. It’s another format. The meme aesthetic changes. The ad aesthetic changes. Attention shifts. Human taste evolves.
So the job becomes less “pontificating about the perfect ad” and more “direct the system.”
Connect the pipes.
Create volume.
Review what works.
Ship more.
Repeat.
Tech Debt Isn’t a Religion Either
You also get the practical version of the tech debt debate.
If something is a 4 out of 10, don’t stop the company for three months to make it a 9. Get it to a 5. Incremental improvements reduce the compounding pain without killing momentum.
But ignoring everything forever makes the system fragile. Fire drills happen. Output drops. Quality drops.
The decision is tied to the objective:
High churn? Fix what’s broken.
Good retention but slow growth? Build new stuff.
AI Makes the Tactical Work Ridiculously Fast
The most “okay this is real” moment is using AI to speed up DevOps style work and finding serious cost savings fast.
Not because AI runs the company. Because it makes diagnosis quicker and execution cheaper.
Tactical work gets faster.
Strategic decisions still matter.
2026 isn’t going to reward the best opinions.
2026 is going to reward velocity, iteration, and people who ship, learn, and adjust without turning every decision into a sacred ritual.
