Uh-Oh Everything's Broken with Jonathan Sturgeon

Welcome back to Founder Mode!

I spend a lot of time thinking about systems. Sales systems. Product systems. Support systems. And today I want to share something we don’t hear enough: You don’t need to be an influencer to win.

In this week’s episode of Founder Mode, we talked to Jonathan Sturgeon. He runs two real businesses (a creative agency and an IT company) with no personal brand, no daily posting habit, and no growth hacks. His model is simple. Be useful. Reach out directly. Deliver value.

It sounds obvious, but most founders today are being told to post daily and chase followers. Jonathan proves there’s another way.

Let’s get into it.

Pretty Good IT: A New Model

At Pretty Good AI, we believe in building trust by delivering results. Jonathan’s new business follows the same mindset.

Here’s what he did:

• Offers 30 days of IT support for free
• Then let customers pay what they think it’s worth
• Handles everything in Slack, no portals or ticket systems
• Starts small and builds trust over time

That last one stuck with me. As Jonathan said:

“As a founder, do you think I want to go submit a ticket? No. I want to talk to a person and get it done.”

That’s the mindset we use at Pretty Good AI. We don’t sell hype. We solve problems. And sometimes the simplest interface is the right one, even if that’s just a Slack ping.

5 Key Takeaways

1. You don’t need a personal brand to build a real business. Cold emails and direct outreach still work. Just have a strong offer and a solid system.
2. Don’t just post. Talk to customers. Jonathan built his agency by calling leads and closing deals. No ads. No posts. Just conversations.
3. Pricing experiments succeed when you build trust first. “Pay what it’s worth” may seem risky, but great service fosters loyalty quickly.
4. Remote IT can be delightful if built right. Forget clunky help desk software. Just solve problems fast and don’t make the founder do more work.
5. Don’t overthink your growth stack. Most people spend too long planning. Jonathan’s team launched a simple page with jokes, and it went viral thanks to Sam Parr. Momentum beats perfection.

Final Thoughts

I like this episode because it reminds us that attention isn’t the only asset that scales. So does trust. So does consistency.

Jonathan’s story is a good reminder: If you make something useful and tell people about it directly, that’s still enough.

We apply the same principle at Pretty Good AI. No bloated sales decks. Just live demos, working integrations, and fast onboarding.

If you’ve been chasing growth through social posts but not seeing results, maybe it’s time to go old school. Pick up the phone. Send a real email. Ask a customer what’s not working.

Sometimes the best growth isn’t loud. It’s just good.

🎧 Listen to Episode 39 here:

Uh-Oh Everything's Broken wi... Jan 15 · Founder Mode 28:18   ​

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-kevin

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