Jun 16, 2026
In February 2020, Willie Litvack had his biggest month ever. Squadup — the self-service ticketing platform he'd spent six years building brick by brick — had just crossed $400K in monthly revenue. The business was profitable. The momentum was real.
Then the phone rang.
Within nine days, revenue went from $400K to zero. Willie had to furlough 17 people on a call with a lawyer billing $700 an hour — a lawyer he couldn't afford. And he had to figure out how to keep the lights on with almost nothing in the bank.
What he did next is a masterclass in leading through chaos.
In this episode, Willie shares:
How he built Squadup from zero to $5M ARR without VC money — and why that made COVID hit harder
The emotional reality of letting 17 people go in a single day and what it took to carry that
Why the CEO's job is to be a shield — and what happens when the shield breaks
How they used the downtime to rebuild the product and came out stronger on the other side
The eventual exit and what it actually felt like
Why he started Press On Ventures — and what "press on" means to him personally
The three I's framework he uses to evaluate every founder: Integrity, Intensity, Intelligence
The role his wife Madeline played in making all of it possible
If you've ever had to hold it together when everything was falling apart — this one's for you.