Trean Insurance June 2022 Investor Presentation

Investor Presentation

June 2022

Disclaimer

This presentation of Trean Insurance Group, Inc. (the "Company") contains forward-looking statements as that term is defined in the Private Securities Litigation Reform Act of 1995. Forward-looking statements include statements that are not historical or current facts. These statements may discuss the Company's net income, cash flow, financial condition, impairments, expenditures, growth, strategies, plans, achievements, dividends, capital structure, organizational structure, market opportunities and general market and industry conditions. You can identify forward-looking statements by words such as "anticipate," "estimate," "expect," "intend," "plan," "predict," "project," "believe," "seek," "outlook," "future," "will," "would," "should," "could," "may," "can have," "likely" and similar terms. Forward-looking statements are based on management's current expectations and assumptions about future events. These statements are only predictions and are not guarantees of future performance. Forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those in the forward-looking statements, if the underlying assumptions prove to be incorrect or as the result of risks, uncertainties, and other factors, including the impact of the COVID-19 pandemic on the business and operations of the Company and our policyholders. Other factors that may cause such differences include the risks described in the Company's filings with the U.S. Securities and Exchange Commission (the "SEC"), including its Quarterly Report on Form 10-Q for the quarter ended March 31, 2022. These forward-looking statements speak only as of the date of this presentation. Except as required by applicable securities laws, the Company disclaims any obligation to update or revise any forward-looking statement, whether as a result of new information, future developments, changes in assumptions or otherwise. You should not place undue reliance on the forward-looking statements contained in this presentation.

All future written and oral forward-looking statements made in connection with this presentation attributable to the Company or persons acting on the Company's behalf are expressly qualified in their entirety by the above paragraph.

Filings with the SEC

The Company's filings with the SEC can be accessed through the "Investor Relations" link on the Company's website, www.trean.com. The Company's filings with the SEC can also be accessed through the SEC's EDGAR Database at www.sec.gov (EDGAR CIK No. 0001801754).

Non‐GAAP Financial Measures

Within this investor presentation we may present certain financial measures, including‐adjusted retuon equity and adjusted net income,‐ which are "non‐GAAP financial measures" as defined in Regulation G pursuant to Section 401 of the Sarbanes Oxley Act of 2002. If presented, a reconciliation of such‐ non GAAP financial measures to our most directly comparable GAAP financial measures will be included in the attached appendix. Management believes that these non GAAP financial measures are important to the Company's investors, analysts and other interested parties who benefit from having an objective and consistent basis for comparison with other companies within our industry. Management further believes that these measures are more relevant than comparable GAAP financial measures in evaluating our financial performance.

These measures should not be viewed as a substitute for those determined in accordance with GAAP. Reconciliation of these measures to their most comparable GAAP financial measures are included in the appendix to this presentation. They are also included in our most recent earnings release available in the "Investor Relations" section of our website at www.trean.com.

Company Overview

Trean Insurance Group, Inc.

An established, growth-oriented company providing products and services to the specialty insurance market. With a focus and expertise in underserved specialty casualty markets, Trean offers a multi-service model and produces a diverse set of revenue and earnings streams including:

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Company Overview

1. Represents the percentage of net earned premiums relative to gross earned premiums
2. Upgraded from A- (Excellent) to A (Excellent) in May 2019

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Key Investment Highlights

Multi-Service Value Proposition

• Allows for unique positioning within the market
• Creates better-than-industry results

Proven and Sustainable Growth Strategy

• Strong and disciplined program partner selection process
• Disciplined risk management & well-managed balance sheet

Entrepreneurial, Experienced Management Team

• Expertise in Specialty Insurance, decades of industry experience and executive leadership
• Supported by a board of directors with deep expertise and commitment to the Company

Well-Positioned for Future Growth

• Attractive embedded potential earnings
• Consistently creating new opportunities

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