Selected transactions
A selection of companies where Ryan Addis led, operated or advised, from Oak Stream mandates to earlier ventures.
2026 · Oak Stream transaction
Health insurance distribution, Michigan
An Oak Stream Partners transaction led by Ryan Addis. Bryson, a diversified insurance and financial services organization based in Long Beach, California, announced its acquisition of Altruis, a Michigan-based health insurance distribution organization serving independent insurance professionals, on October 1, 2026, establishing a platform for its expansion in the Midwest.
2019–2020 · President & COO
Auto and home insurance agency and insuretech platform
Ryan led operations and growth for this 45-state agency with more than $175M of in-force premium. Revenue doubled and EBITDA grew fivefold within 12 months, enterprise-value offers rose from about $3M to more than $70M during his tenure, and he secured growth capital for the business.
2017–2019 · Consultant
Multi-state auto managing general agent
Ryan served as a consultant to this auto MGA with $45M in premium and placed a $30M quota-share reinsurance program.
2015–2016 · Chairman & CEO
National P&C and auto managing general agent
Ryan led this MGA writing more than $150M of annual premium through more than 2,100 independent brokers, where EBITDA margin rose from 24% to 39% in 18 months. He built a forecasting model accurate to within 0.7% monthly error, introduced fraud-detection and claims technology, launched a program with a pure loss ratio under 55% and positioned the company for a successful acquisition exit.
2002–2005 · Co-founder & COO
Wholesale mortgage, mortgage banking and escrow
Ryan syndicated a group of independent mortgage brokers and merged with a mortgage bank to build a wholesale platform that reached $1.2B of annual origination volume across 26 states, followed by a liquidity event in 2005.
Roles describe Ryan Addis’s personal involvement. Some engagements predate Oak Stream Partners or were undertaken in an executive capacity. Figures come from company records and Ryan’s professional history and are approximate. Past results are not indicative of future results. Not every engagement is listed, and some were confidential.
Confidential conversation
If you own a business in our range, or in insurance and warranty specifically, we would welcome a confidential conversation.