Ryan Letzeiser

Co-Founder & CEO @ Obie | Insurance & Real Estate Nerd | Y Combinator S-19

Co-founder

Obie· Summer 2019Greater Chicago Area

2018Co-founder· Obie

Founder · since 2018

Company

Obie

Role

Acquired Jan 2026 (BWIN - Nasdaq)

current

Stage

—

no public source

Raised

—

no public source

Based

Chicago, Illinois, United States

current

Founder / co-founder — the company's markEmployee / research role

Profile coverage5 of 7 · missing posts, contact

Obie

Moving Investment Property Insurance Forward

Experience

Career

Obie
Co-founder
Co-Founder & CEO (YC S19) - Acquired Jan 2026 (BWIN - Nasdaq) · Chicago, Illinois, United States · 2018 – Present
2018
MAC Properties
Managing Member · 2015 – Present
2015
Hudson Capital Investments
Sr Investment Associate · Charleston, South Carolina Metropolitan Area · 2011 – 2015
2011
Ram Real Estate
CRE Development and Investment Analyst · Palm Beach Gardens Florida · 2010 – 2011
2010
Clemson University
Graduate Assistant · Clemson, SC · 2008 – 2010
2008
Dyanmic Edge inc
Business Development & Sales · Ann Arbor, Mi · 2006 – 2008
2006
C and L Ground Designs
Owner · Novi, Mi · 2001 – 2007
2001