Scaling from 40 to 8 People Doubled Profits — High Ticket AI Systems Podcast

About this episode

I sat down with Jordan Lally on the High Ticket AI Systems Podcast for a conversation that wandered well past email tactics — into why I stayed in one lane, how we've run remote from day one, and the messy middle of growing an agency too big for its own good.

We talk about stubbornness and depth: fifteen years in DTC email and SMS, eleven-plus running Essence of Email, and why going deep has always felt more interesting to me than going wide. Jordan asked how I balanced travel and work in the years we were highly mobile (~40 countries, always remote-native since late 2013). Honest answer — work is infinite; some experiences aren't. You have to choose, and sometimes you choose the cliff dive.

The heart of the episode is the scale-up / scale-down story. We undercharged early, demand piled up, and I didn't know how to grow a team well — underpaying for talent, stacking management layers and SOPs too soon, chasing what I thought a “real company” was supposed to look like. Headcount climbed toward forty. Delivery got thinner. Competition got louder. I burned out, stepped back for a stretch, and eventually had to walk back in and make cuts that still sit heavy — then rebuild around our DNA, who we work with, and what we refuse to half-do.

On the other side: a leaner team (~8), less impressiveness on a LinkedIn headcount, more profit, better people, and work that still excites me. We close on recalibrating what success actually means as you change — and what I'm excited to build next with AI for our clients, plus a personal note on living in Kyiv right now.

Key takeaways

I’d rather go deep than wide — one lane, one craft, and a network that compounds over years.
In a talent business, A-players vs. everyone else isn’t a 1.5× gap. It’s closer to 10× constructive vs. −10× destructive. You get what you pay for.
If the system is broken, scaling headcount just scales the break — same as pouring budget into ads with negative ROAS.
I tried to bolt enterprise SOPs and management layers onto a small team too early. We got meetings about meetings — not leverage.
We grew toward ~40 people. I burned out, stepped back, and eventually had to cut deep when delivery and the economics cracked.
The hardest cuts weren’t fat — they were people we valued, when we were already lean. Necessary. Still rough.
Coming out the other side: a smaller team (~8), less vanity revenue, our most profitable year, and work I actually want to do with people I love working with.
What you wanted two years ago may not be what you want now. Hit the old goal without recalibrating and you can still feel empty.
Protect some recovery — weekends, space — so you can stay in the game at high RPMs for a marathon, not a permanent sprint.
What’s next for us: building a proprietary AI strategic layer for our clients — customized, not a public product that distracts from the craft.