Aaron Letzeiser and Ryan Letzeiser of Obie named Entrepreneur Of The Year 2026 Midwest Finalists by EY US

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EY US celebrates ambitious entrepreneurs shaping the future of business

‍CHICAGO, April 22, 2026 — Aaron Letzeiser, Co-Founder and COO, and Ryan Letzeiser, Co-Founder and CEO of Obie, have been named finalists for the Entrepreneur Of The Year® 2026 Midwest Award by Ernst & Young LLP (EY US).

Now in its 41st year, the Entrepreneur Of The Year program celebrates the bold leaders who disrupt markets through the world’s most ground-breaking companies, revolutionizing industries and uplifting communities. The program honors entrepreneurs whose innovations drive economic growth and help shape the future of business.

An independent panel of judges selected Aaron and Ryan Letzeiser among 37 finalists from 30 companies based on their entrepreneurial spirit, purpose, company growth, and lasting impact in building long-term value.

“This recognition means a lot to us. It reflects the work we’ve put in to build a platform that’s truly aligned with how our partners and customers operate. We’ve made meaningful progress, and that’s a direct result of the team and the people we work with every day. We’re proud of how far we’ve come and even more focused on what’s ahead,” said Aaron Letzeiser, Co-Founder and COO of Obie.

Founded in 2017, Obie was built to solve a problem Aaron and Ryan experienced firsthand: securing insurance for real estate investments was slow, opaque, and built for a different era.

Drawing on their backgrounds in insurance and real estate private equity, they set out to create a faster, more transparent experience. What started as a solution to a personal frustration has since grown into a platform that enables landlords, agents, and partners to move from quote to coverage in minutes, not weeks.

Since then, Obie has secured more than $60 billion in coverage and written over $300 million in premium, supporting a growing network of real estate investors, property managers, agents, and lending partners nationwide. The company’s approach to embedded insurance has also expanded how coverage is delivered, integrating directly into the platforms and workflows where real estate transactions happen.

Under Aaron and Ryan’s leadership, Obie has continued to evolve alongside the needs of the market, expanding its product offerings, strengthening its carrier partnerships, and investing in technology that simplifies how insurance fits into real estate.

In 2026, Obie was acquired by The Baldwin Group (NASDAQ: BWIN), a leading independent insurance brokerage firm. The acquisition further strengthens Obie’s ability to scale its platform while continuing to focus on the specialized needs of real estate investors and the partners who support them.

About This Honor

The Entrepreneur Of The Year program recognizes leaders who are building and scaling companies with lasting impact. From early-stage founders to established operators, the program highlights those who are pushing industries forward through innovation, growth, and long-term value creation.

Aaron and Ryan’s recognition as finalists reflects the progress Obie has made in rethinking how insurance fits into real estate. What began as a solution to a broken process has grown into a platform used by investors, agents, and partners across the country.

This year’s Midwest finalists represent a diverse group of companies across Illinois, Indiana, and Wisconsin, spanning industries from technology to manufacturing and financial services. Winners will be announced on June 11 in Chicago and will advance to the national stage later this year.

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About Obie

Obie is an insurance platform built for real estate investors, offering fast, technology-driven coverage for rental properties. Founded in 2017, Obie provides instant, bindable insurance solutions and partners with agents, lenders, and property managers to simplify the insurance experience across the real estate ecosystem.

Sponsors‍

Founded and produced by Ernst & Young LLP, the Entrepreneur Of The Year Awards include presenting sponsors PNC Bank, Cresa, LLC, Marsh USA, SAP, and the Ewing Marion Kauffman Foundation. In Midwest, sponsors also include Platinum sponsor LaSalle Network, Gold sponsors Becker Professional Education and Big Picture, and Silver sponsor ADP.

About Entrepreneur Of The Year®

Founded in 1986, Entrepreneur Of The Year® has celebrated more than 11,000 ambitious visionaries who are leading successful, dynamic businesses in the US, and it has since expanded to nearly 80 countries and territories globally. The US program consists of 17 regional programs whose panels of independent judges select the regional award winners every June. Those winners compete for national recognition at the Strategic Growth Forum® in November where national finalists and award winners are announced. The national overall winner represents the US at the World Entrepreneur Of The Year® competition. Visit ey.com/us/eoy. 

About EY‍

EY is building a better working world by creating new value for clients, people, society and the planet, while building trust in capital markets. Enabled by data, AI and advanced technology, EY teams help clients shape the future with confidence and develop answers for the most pressing issues of today and tomorrow. EY teams work across a full spectrum of services in assurance, consulting, tax, strategy and transactions. Fueled by sector insights, a globally connected, multi-disciplinary network and diverse ecosystem partners, EY teams can provide services in more than 150 countries and territories. All in to shape the future with confidence.

EY refers to the global organization, and may refer to one or more, of the member firms of Ernst & Young Global Limited, each of which is a separate legal entity. Ernst & Young Global Limited, a UK company limited by guarantee, does not provide services to clients. Information about how EY collects and uses personal data and a description of the rights individuals have under data protection legislation are available via ey.com/privacy. EY member firms do not practice law where prohibited by local laws. For more information about our organization, please visit ey.com. 

Media Contact:
Obie Insurance
press@obieinsurance.com
‍obieinsurance.com

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