How I Built a $200M Company with 96% Margins (Before AI Was Cool)
Long before AI was trendy, I was running a health insurance startup with a secret weapon:
26 employees...but 5 of them weren’t human.
Instead of building bloated teams, we used bots to automate what others hired for. We scaled fast, stayed lean, and kept 96% of every dollar.
Today, building an AI-first business is 10x easier — and it will define who wins over the next five years.
Back then, it wasn’t easy.
We had to custom-build most of the systems ourselves — bots for onboarding, billing reconciliation, customer service, and reporting.
It wasn’t about adding tech to support people. It was about redesigning the business so it needed fewer people to begin with.
Fast forward to today — and founders have an even bigger advantage.
What took us months (and engineering teams) to build can now be set up in days with AI agents, swarms, and automation tools that didn’t exist 10 years ago.
The opportunity isn’t just to save costs. It’s to fundamentally rewire how businesses are built — and create exponential leverage with a fraction of the effort. When I built Joany, we achieved outsized revenue and outsized margins with a tiny, AI-augmented team.
But if I had to build that company again today?
I’d push even further.
I would slash at least half of the remaining human-driven workflows — especially in areas like customer support — and move them to AI-driven processes.
Not because I couldn’t before. But today, I wouldn’t need a 5-person engineering team to pull it off.
I could do it myself over a weekend, or with one strong automation and AI specialist hire.
How We Used Bots 10 Years Ago
Even back then, at Joany, we were already using bots to manage core operational areas:
Invoice Reconciliation
Collections Tracking and Escalation
State Filing
Licensing Management
Talent Sourcing and Scheduling
Health insurers had no idea they were communicating with our bots. These bots handled data-heavy, rules-based work that didn’t require human judgment, even before modern AI tools made it easier.
"Employee" Bots at Joany in 2015
Where I Would Push AI Further Today
If I were building the same company today, here's where I would immediately push even deeper into AI-first workflows:
Customer Support: FAQs, ticket routing, escalation triage, AI agents as first-line support.
Customer Messaging: Automated behavioral emails, text reminders, push notifications.
Collections Escalation: Payment plan offers, late invoice workflows, personalized escalation paths — AI-managed.
Finance Reporting: Daily reconciliation, vendor payment auditing, automated finance dashboards.
Operations Support: Task routing, backend updates, internal ticket management.
Regulatory Compliance Prep: Data assembly, deadline alerts, reporting prep.
Digital Marketing: SEO content drafts, ad copy variations, A/B testing ideas.
Internal Analytics: KPI monitoring, trend reporting, churn risk alerts.
About 40–50% of Joany’s workflows could now be fully AI-driven, with dramatically less manual effort, higher speed, and even wider margins (!!)
The Mindset Shift Founders Need to Make Now
When I coach founders today, this is the shift I push them to make:
It’s not about asking "how can AI support my team?"
It’s about asking "what parts of my business should AI run entirely?"
Tobi Lütke, CEO of Shopify, recently told his team:
“Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI.”
The smartest founders aren’t treating AI like a tool. They're rebuilding their companies to be AI-first — not AI-assisted.
This isn’t about trends. It’s about survival.
In 5 years, AI-first companies will dominate every sector.
Founders who adapt now will be light years ahead.
Those who wait will spend the next decade trying to catch up.
A Real Example: Why This Matters Today
On a recent coaching call, a founder I work with faced a hard choice:
His company was burning cash faster than expected. Pressure from investors was mounting. The instinct was to cut staff — fast.
The problem?
Every role he cut would also cut a piece of the company's growth engine.
In trying to save cash, he risked killing future revenue, too.
It’s a common trap:
Cut expenses → Cut capacity → Lose revenue → Burn anyway.
What he needed wasn’t just a smaller team. He needed more leverage with fewer people. He needed a different operating system.
That's where AI comes in.
How Founders Can Start Building an AI-First Company Today
If you're in the same spot — feeling cash pressure, growth pressure, hiring pressure — you don't need to overhaul everything overnight.
You just need to start moving.
Here’s where I'd start:
Spend 20 minutes a day tinkering with AI tools. ChatGPT, Claude, Lindy — don’t study them. Play with them. See what’s possible.
Pick one painful task to automate. Scheduling? Lead follow-ups? Social content? Start there.
Map your business by workflows, not job titles. What repeatable processes exist? That’s where your first AI agents should go.
Challenge your leadership team. Instead of asking for more headcount, ask: “How much of this can we automate?”
Redesign from first principles. Not “how do we help employees with tech.” But “what functions can run 90% AI, 10% human oversight?”
Start small. Move fast.
Let momentum compound.
The Founders Who Will Win the Next 5 Years
Here’s the truth:
Founders who master AI-first thinking will build businesses that are faster, leaner, and more resilient than anything we’ve seen before.
They’ll create moats so wide it’ll be almost impossible for traditional companies to catch them.
Founders who don’t move now will spend the next five years bleeding cash, fighting headcount battles, and wondering what went wrong.
This isn’t a tech trend. It’s a business survival strategy.
The sooner you start, the bigger the gap you’ll build between you and everyone else.
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See you next week! 👑
If you're ready to scale smarter,
Here's where to start:
⚫️ The CEO Delegation Mastery: Delegate 80% of your workload and reclaim your time.
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