Captain's Log
Captain's Log
Stories from the trenches of running companies.
From a $3 Million Lowball to a $70 Million Offer in 12 Months
How a break-even insurtech agency found its rhythm, measured in milliseconds, and then bet against the herd when COVID hit.
5 min read · 7 min listen →
The Deal That Blew Up the Day Before Closing, and the Deal That Came Out of It
A failed acquisition, a surprise promotion in a boardroom, and a 72-hour stretch with no sleep.
6 min read · 8 min listen →
I Thought It Was a Safe Port. It Turned Out to Be the Eye of the Storm.
A Hollywood gala, a nonprofit turnaround, and two years inside the wholesale division of America's biggest mortgage lender as the 2007–2008 crisis hit.
6 min read · 8 min listen →
The Syndicate, the Shoeshine Boy, and Knowing When to Get Off the Ship
How a 23-year-old with long hair went from a commission-only loan originator to $1.2 billion a year in mortgages, and why he walked away in 2005.
5 min read · 7 min listen →
"The Stupidest Idea Ever," Strep Throat, and the Birth of Oak Stream
How a mortgage guy without a Harvard or Stanford MBA bet everything, with no plan B, on raising a search fund in 2013, and why the people who backed him had all built something themselves.
6 min read · 8 min listen →
Confidential conversation
Considering a sale, recapitalization or succession?
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@oakstreampartners.com - Office hoursMonday–Friday, 9 AM–5 PM Central