3 Startup Rules I Broke — And Why It Saved My Business

Why I ditched the “best practices” everyone swears by — and why breaking the rules saved my solo AI startup from failure.

By Jeremy Gustine edited by Maria Bailey Oct 13, 2025

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Key Takeaways

  • Bootstrapping my solo AI startup showed me that the common “best practices” aren’t always what they seem.
  • I discovered that sometimes, breaking the rules is exactly what you need to do when you’re flying solo.

When you’re bootstrapping a solo AI startup, everyone has an opinion.

Freemium. Waitlists. Subscriptions. Build in public. Raise capital.

These so-called “best practices” get repeated like gospel. But here’s what I’ve learned the hard way: most of them aren’t rules — they’re just suggestions that worked once for someone else.

Some advice is useful. Most of it is conditional. And a lot of it? Just noise.

I don’t ignore all of it. But I’ve learned when to break the rules — and why it can actually work better when you do.

1. I skipped freemium. Here’s why I don’t regret it.

Freemium is almost gospel in SaaS: show your value before asking for payment, let users try it, love it and convert. It’s a model that works — until it doesn’t.

For PhotoPacks.AI, my startup that creates high-quality AI headshots, freemium wasn’t just risky — it was financially impossible. Every photo upload requires training a model on expensive GPUs, costing me $3 to $4 per user. With thousands of browsers likely to take a single free headshot and never return, offering a free sample was a fast track to bankruptcy.

Instead, I relied on social proof. I charged upfront, kept prices low at launch and focused on a seamless experience. While it turned some people away, the customers who stayed were more committed — and those were exactly the ones I wanted.

Related: 3 Essential Skills I Learned By Growing My Business From the Ground Up

2. I raised prices — and my customers got better

At first, I priced it at $9.99 — cheap, probably too cheap. I wanted traction, but I noticed a pattern: most support requests came from the lowest-paying customers. More refunds, more complaints, more time wasted.

So I doubled the price — and then raised it again. I lost about 10% of my volume, but refund requests dropped sharply. My average customer was more pleasant, emails were friendlier and I made more money with less effort.

The lesson? Pricing isn’t just about revenue. It’s a filter for the kind of customers you want to serve.

3. I ignored the hype machine

I also skipped the waitlist. Collecting emails doesn’t guarantee real users. Validation can be a false high — people often click “Join Waitlist” out of curiosity, not intent. I preferred building an MVP quickly and getting genuine feedback over chasing vanity metrics.

The same goes for social media. I tried TikTok, Facebook and Instagram, but none drove meaningful traction. What worked instead was organic search, word-of-mouth, and direct conversations with customers. So I focused on those and stopped worrying about the rest.

Related: 5 Things You Need to Stop Doing as a Solopreneur

Not all rules are useless — just overrated

There’s one rule I still live by: the golden rule. Treat others how you want to be treated. That shows up in how I handle support, how I price fairly, and how I prioritize features. It’s not revolutionary. But it works.

And here’s the bigger point: best practices are just averages. They’re designed for the “typical” startup — the one with a team, capital and time. If you’re a solo founder building something weird, niche or scrappy? You’re the exception. And exceptions make their own rules.

So learn the playbook — then feel free to throw it out.

Key Takeaways

  • Bootstrapping my solo AI startup showed me that the common “best practices” aren’t always what they seem.
  • I discovered that sometimes, breaking the rules is exactly what you need to do when you’re flying solo.

When you’re bootstrapping a solo AI startup, everyone has an opinion.

Freemium. Waitlists. Subscriptions. Build in public. Raise capital.

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Jeremy Gustine

Founder and CEO of PhotoPacks.AI and Mimic.art at PhotoPacks.AI
Entrepreneur Leadership Network® Contributor
Jeremy Gustine is a seasoned software developer and entrepreneur. As founder of PhotoPacks.AI and Mimic.art, he blends his passion for AI and computer vision to make professional, creative tools accessible to all, helping people elevate their personal and professional brands.

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