If you're reading this, you've probably told someone "we're crushing it" while quietly wondering if this thing is even going to work.
Every Wednesday, you get the stories founders don't tell on LinkedIn. What they got wrong. What it cost. What they wish they had known a year earlier.
First issue: Miami, last fall. Three founders, an hour-long panel, the two teardowns that stuck. Plus the next room worth booking.
Lessons From The Room
Three founders at Miami. Below: the two teardowns that stuck.
1. The seven-year build that exited on the wrong thing
Nafis Azad speaking. Left to right: Nafis (Lucky, sold to SPINS), Bogdan Savonea (Blindspot), Guillermo Gonzalez Aleman (Litebox), Anson Wu (host).
What he got wrong. For seven years, Lucky thought it was a consumer experience company building retail partnerships. Sephora, Ulta, Nordstrom, Bloomingdale's, Walmart, Best Buy.
What it cost. Seven years building a product that turned out not to be the asset.
What he wishes he had known. The proprietary retail data they were accumulating across those partnerships was the real asset. The buyer paid for the data, not the product.
"We probably exited based off of underwriting that had nothing to do with really the product that we had built in 2021. It was a lot more to do with the partnerships and the data we had accrued trying to build that product."
If you're seven months into a build and the thing your customers actually keep coming back for is something you weren't even tracking last quarter, pay attention to it before someone else does.
2. The RTO experiment that almost broke forty people
Bogdan speaking.
What he got wrong. Tried five days a week in office. Then two days a week. Both failed.
What it cost. Months of bad policy across teams in Ukraine, India, Romania, New York, LA, and Miami. Plus the trust hit every team takes when leadership reverses itself on where people work.
What he wishes he had known. The cadence that actually worked was one day a month. Everyone shows up, works together, has a beer at the end of the day, goes home.
"We tried two days a week, which was just as bad. And then we tried something. One day a month. And that was probably the most successful thing. Everybody comes to the office, they work together, have a beer at the end of the day."
The default debate is full RTO versus hybrid. The answer Bogdan ran the actual A/B test on was neither.
Listen to the whole Ugly Talk on the Podcast
Ugly Talk Happening Next
FEATURED · BOSTON Friday, May 29 · 2:00–4:00pm ET
How To Actually Build At The Speed Of AI And Outship A Bigger Team
Greg Cucino takes the floor. Inc. 500 entrepreneur. Co-founder of the MIT Sloan CFO Summit. Now building InfinixIQ, an AI-powered ERP launching this month.
The conversation: the practical AI moves small teams are running this year to ship faster than incumbents three times their size. Not prompt-engineering theatre. The workflow plays that actually compound, and the vanity buys you'll regret 18 months from now.
Havana Event Space · CIC Cambridge, 1 Broadway
🗽 New York
🦞 Boston
If a lesson up there landed, forward this to the founder you know who needs to hear it. They probably told someone they were crushing it this morning, too.
See you in the next Ugly Talk.