Multi-Family Office

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TrueNorth Companies

TrueNorth Companies is a family office and insurance brokerage founded in 2001, led by CEO Jason Smith. Operates across 22 U.S.

TrueNorth Companies

Discover insurance, risk, and financial solutions tailored to businesses, individuals and families nationwide. Find your TrueNorth today.

General information

Firm type

Multi Family Office

Year founded

2001

AUM

Undisclosed

Location

Region

North America

Country

United States

City

Cedar Rapids

Corporate office

Cedar Rapids, IA, United States

Additional offices

Denver, CO · Rosemont, IL · West Des Moines, IA · Alabama · Arizona · Arkansas · Colorado · Florida · Georgia · Illinois · Iowa · Kansas · Michigan · Minnesota · Montana · North Carolina · South Carolina · Tennessee · Texas · Utah · Washington · Wisconsin

Principals

Jason Smith

CEO

Trent Tillman

President and Chief Revenue Officer

Duane Smith

Former CEO (founding CEO)

Sector focus

InsuranceRisk ManagementTransportationAgribusinessConstruction

Frequently asked questions

Who runs investment decisions at TrueNorth Companies?

Jason Smith, CEO, and Trent Tillman, President and Chief Revenue Officer, lead strategic direction. The firm's SRO strategy is executed by its executive team, with Chad Thurm as CFO and Matt Rathje as COO (per firm website, 2025).

How does TrueNorth source proprietary deal flow?

TrueNorth sources investments through its SRO strategy, which targets businesses that complement its core insurance and risk management services. The firm also uses its network of 22 U.S. offices and its First MainStreet Insurance (FMSI) affiliate to identify acquisition targets among independent agencies.

Is TrueNorth structured as a single family office or does it operate more like a venture firm?

TrueNorth operates as a hybrid — primarily an insurance brokerage with a family-office-style investment arm. Its SRO strategy acquires and holds operating businesses, generating recurring revenue and capital appreciation, more akin to a multi-family office or holding company than a traditional venture firm.

Does TrueNorth participate in fund commitments or only direct deals?

TrueNorth's public disclosures focus on direct investments through its SRO strategy, acquiring businesses that complement its brokerage services. It does not report participating in external fund commitments.

What investment stages does TrueNorth typically target?

TrueNorth targets mature, cash-flow-generating businesses in the insurance and risk management ecosystem, typically through acquisitions of independent agencies or complementary service providers via its SRO strategy.

Which sectors does TrueNorth explicitly focus on?

TrueNorth concentrates on transportation, agribusiness, and construction, alongside broader property and casualty insurance and employee benefits. It does not publicly disclose sectors it avoids.

Does TrueNorth maintain philanthropic structures, and how are they separated?

Yes, TrueNorth launched the TrueNorth Legacy Foundation in January 2021, a private 501(c)(3) foundation focused on community philanthropy. It is separated from the for-profit brokerage and operates as a distinct legal entity (per firm website).

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