Episode Stack: https://stackl.ist/48R3vkY

Don't miss this episode. I loved this conversation with Stephen Messer, who co-founded LinkShare with his sister in the late 90s and sold it to Rakuten after about 10 years. He's now building Collective[i], an AI platform that makes your professional network actually usable.

Stephen walked me through the first four years of LinkShare when they lived in one apartment, rotated shifts on two computers, and he worked directly on the main server because they couldn't afford another machine. During their pitches they had to spend first hour explaining what the internet was before they could even talk about the business. Revenue didn't grow until year six or seven because they charged 2% per transaction and needed massive volume.

One of my favorite stories: Michael Dell called him on a Sunday night and Stephen thought it was a prank for 30 minutes. That partnership changed everything. The first retailers all said "call us when you have affiliates," but direct marketers like Omaha Steaks understood the model from catalog days and signed up first.

His take on most startup advice: ignore it and find your own style. Really appreciated Stephen's time and honesty about what building actually looks like.

0:00 - Introduction
2:49 - Growing Up Outside NYC & Getting Into Law
6:46 - Coming From an Entrepreneurial Family
8:03 - The Origin of LinkShare & Affiliate Marketing
9:24 - Living in One Apartment, Sharing Two Computers
11:45 - Pitching Before E-Commerce Existed
14:03 - Getting First Customers: Omaha Steaks & 1-800-FLOWERS
16:28 - The Michael Dell Sunday Night Call
19:15 - Four Years of Pain Before Growth
21:30 - Why Revenue Didn't Grow Until Year Six
24:15 - The Rakuten Sale & Going IPO
27:45 - Why Founding is "Shit All The Time"
30:20 - Life After Selling: You Can't Turn It Off
33:40 - Why Past Skills Don't Always Transfer
37:15 - The Danger of Becoming Overconfident
40:30 - Starting Collective[i] & Neural Networks
45:20 - The Network Problem: Why We Can't Use Our Relationships
51:45 - How Collective[i] Works
56:10 - Advice for Founders: Ignore Most Startup Content
59:30 - Never Live Above the Second Floor