Everything Marketplaces · Oct 5, 2026 · 46m · 32m saved
With John Koelliker, Co-founder and CEO of Leland
Leland replaced an email sales team with a group of AI agents that one entry-level employee oversees part time, and the agents bring in more than $1M a year, co-founder John Koelliker said.
Investors have cooled on marketplaces while money pours into AI companies that resell model capacity. Koelliker thinks marketplaces grow more slowly than those companies but build network effects that last longer.
"And at the end of the day, supply really just wants to earn money." — John Koelliker
John Koelliker, Co-founder and CEO of Leland, on Everything Marketplaces, has worked on marketplaces for a decade: as an intern at Uber, on LinkedIn's sales and talent marketplaces, and at the shopping-advice startup Curated. Leland, which connects people with paid coaches and experts for career and education goals, has raised more than $20M. The show's own fund, Marketplace Capital, is one of its investors.
The full interview is covered here so you can skip it. 46 minutes of audio, 14 minutes of reading.
Here are the 17 lessons that matter.
Key Takeaways
Fake one side of a new marketplace and sell before building anything
Koelliker was already referring coaching clients to other coaches by hand before Leland existed
The average Leland customer spends over $1,000, and employers were often paying without Leland knowing
A sales team at Anthropic bought coaching on its own, which led Leland to sell company-wide programs
A team of AI agents now brings in over $1M a year with one entry-level employee spending 15% to 20% of his time on it
Leland raised its Series A at about 6M in gross sales and 2M in net revenue, while already cash-flow positive
A preemptive term sheet is usually an uncompetitive process on the investor's terms, in his view
Thumbtack charges for the lead, not the relationship, because customers leave once they meet the provider
His biggest mistakes came from trading customer resonance for scale
1. From MBA Side Hustle
The host asked for Koelliker's background and how Leland started.
Marketplaces became the theme of his career by accident
"I interned at Uber in 2016." — John Koelliker
He then joined LinkedIn, working on its sales and talent marketplaces, and later Curated, a marketplace that connected shoppers with experts. On the side he had been selling coaching and content. He started Leland about five years ago.
He began Leland as an MBA student, and his second child was born in his second week of school
His side business helped people apply to deferred MBA programs, which he called a very small niche. A marketplace was the only way he saw to bring prices down and serve many more kinds of people. He spent a few months persuading engineers he had worked with at LinkedIn to build a first version on the side, during COVID, when they were not going into an office.
Leland launched in one category, raised a $1M pre-seed round at launch and a $4M seed round shortly after. The team was spread across the Bay Area, New York and Los Angeles and has since moved to Utah.
