Wes Mathews didn’t start his second company because he needed another win.
He started it because the first win taught him what actually matters—and what breaks founders over time.
After building High Level Marketing from zero to $20M+ and exiting, Wes hit a truth most founders don’t say out loud: he fell out of love with his own company. The business didn’t need him anymore, his identity was tangled up in it, and he felt stuck. So he did the harder thing—he built again.
In this conversation, second-time founder & CEO Wes Mathews and Josh Linkner get real about the street-fight season of entrepreneurship: why founder-led sales is non-negotiable, why ego has to give way to leverage, and why chaos isn’t a surprise—it’s the tax you pay for growth. Wes also shares how being a dad of five shapes his operating system, and why business should fuel life, not consume it.
In this episode, we jam on:
1. Why founder-led sales is the unreplicable unlock.
What actually breaks momentum when founders step out of sales too early, and why no hire, system, or playbook replaces founder conviction in the market.
2. How to avoid ego sabotaging scaling.
Why Wes stopped trying to be everywhere, do everything, and “prove” himself — and how leverage only shows up once ego steps aside.
3. Why chaos isn’t a leadership failure at $1–$10M.
How growth creates disorder—and what happens when founders design for chaos instead of reacting to it.
4. The trap of “I’ll deal with life later.”
How Wes built rules around family, health, and energy — and why burning your personal capacity eventually burns your business too.
