Ex 991 2019 Annual Meeting Slides

Annual Shareholders Meeting May 21, 2019

FORWARD-LOOKING STATEMENTS As a reminder, we will be presenting certain forward-looking statements, within the meaning of the Private Securities Litigation Reform Act of 1995, or the Reform Act, during this presentation which may include, but are not limited to, statements regarding the Company’s, plans, objectives, expectations and intentions and other statements contained in this presentation that are not historical facts. The forward-looking statements are based on management's current views and assumptions regarding future events and operating performance, and are inherently subject to significant business, economic, and competitive uncertainties and contingencies and changes in circumstances, many of which are beyond the Company’s control. The statements in this presentation are made as of the date of this presentation, even if subsequently made available by the Company on its website or otherwise. The Company does not undertake any obligation to update or revise these statements to reflect events or circumstances occurring after the date of this presentation. Although the Company does not make forward-looking statements unless it believes it has a reasonable basis for doing so, the Company cannot guarantee their accuracy. Certain factors could cause actual results to differ materially from those described in these forward-looking statements. For a list of factors which could affect the Company’s results, see the Company’s filings with the Securities and Exchange Commission, “Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations,” including “Forward-Looking Information,” set forth in the Company’s Quarterly Report on Form 10-Q for the period ended March 31, 2019. No undue reliance should be placed on any forward-looking statements.

CONTENTS Results Examined Growth Key Initiatives

RESULTS EXAMINED Income Statement For the Quarter Ended Year Ended March 31, 2019 December 31, 2018 December 31, 2017 Net premiums earned 12,445,914 $47,116,961 $44,213,271Net investment income 795,373 2,890,266 2,632,498 Net realized investment (losses) gains (47,426) 975,993 1,064,577 Other-than-temporary impairment losses (16,178) (57,316) Net unrealized gains on equity securities 1,840,418 Other income (53,887) 196,649 325,127 Consolidated revenues 14,980,392 51,163,691 48,178,157 Losses and settlement expenses 9,607,290 31,262,462 29,009,833Policy acquisition costs and other operating expenses 4,850,186 18,214,983 17,307,700 Interest expense on debt 32,014 140,877 225,379 General corporate expenses 143,161 545,986 555,109 Total expenses 14,632,651 50,164,308 47,098,021 Earnings before income taxes 347,741 999,383 1,080,136 Total income tax expense 58,993 106,087 372,285 Net earnings 288,748 893,296 707,851 Other comprehensive earnings (loss) , net of tax 1,474,209 (3,808,045) 706,414 Comprehensive earnings (loss) 1,762,957 (2,914,749) 1,414,265 Unaudited

RESULTS EXAMINEDCombined Ratio By Product Line 200% 180% 160% 140% 120% 100% 80% 60% 40% 20% 0% ICC Holdings Net Combined Ratio By Product BP BL LL WC UL Total 12/31/2017 12/31/2018 3/31/2019 Goal

RESULTS EXAMINED Combined Ratio By State 200% 180% 160% 140% 120% 100% 80% 60% 40% 20% 0% ICC Holdings Net Combined Ratio by State IA IL IN MN MO WI OH KS CO MI PA Total 12/31/2017 12/31/2018 3/31/2019 Goal

RESULTS EXAMINED Catastrophic Claim Activity CAT Event Criteria Annual Avg. During 08-17 (10 Years) Annual Avg. During 13-17(5 Years) 2017 2018 2019Number of occurrence CAT events (over $500k) 0.8 0.6 2 2 1 Ceded losses from CAT occurrence treaty $143,911 $78,444 $91,860 $826,404 $2,296,944Number of CAT events subject to aggregate CAT treaty (over $50k) 8.1 9.8 12 18 4Number claims in CAT events 148 151 199 192 120Ceded losses subject to CAT aggregate treaty $1,364,898 $1,485,575 $1,983,046 $2,140,241 $668,201Ceded losses from CAT aggregate treaty $397,816 $369,382 $483,046 $640,241 $0Retained losses from all CAT events $1,232,323 $1,495,540 $2,100,000 $2,400,000 $868,201Reinstatement Premium $4,680 $4,652 $9,461 $120,900 $459,278Retained losses from all CAT events and reinstatement premium

RESULTS EXAMINED Balance Sheet As of March 31, 2019 December 31, 2018 December 31, 2017 Assets Unaudited Investments and cash: Fixed maturity securities 89,927,455 88,981,159 89,605,073 Common stocks 13,701,398 11,843,223 8,534,109 Preferred stocks 3,867,429Other invested assets 243,200 154,200 Property held for investment, at cost, net of accumulated depreciation 3,560,838 3,586,273 3,126,566Cash and cash equivalents 6,409,153 4,644,784 6,876,519 Total investments and cash 113,842,044 109,209,639 112,009,696 Accrued investment income 681,569 648,321 687,453 Premiums and reinsurance balances receivable, net 22,081,040 21,404,344 19,013,262 Ceded unearned premiums 783,694 796,065 274,972Reinsurance balances recoverable on unpaid losses and settlement expenses, net 15,108,689 6,735,964 10,029,834Current federal income taxes 999,614 847,271 573,147Net deferred federal income taxes 253,642 1,021,398 349,258 Federal income taxes 1,253,256 1,868,669 922,405 Deferred policy acquisition costs, net 5,243,470 5,247,188 4,592,415 Property and equipment, at cost, net of accumulated depreciation of 3,229,627 3,332,810 3,503,904 Other assets 1,046,815 1,040,193 1,301,420 Total assets 163,270,204 150,283,193 152,335,361 Liabilities and Equity Liabilities: Unpaid losses and settlement expenses 61,017,342 51,447,440 51,074,126 Unearned premiums 29,983,133 29,972,623 26,555,582 Reinsurance balances payable 4,544,231 993,004 327,483 Corporate debt 3,484,606 3,484,606 4,339,208 Accrued expenses 2,570,332 4,536,218 4,274,002 Other liabilities 1,217,501 1,256,003 1,663,415 Total liabilities 102,817,145 91,689,894 88,233,816 Equity: Common stock 35,000 35,000 35,000 Treasury stock, at cost (3,001,395) (2,999,995) Additional paid-in capital 32,545,836 32,505,423 32,333,290 Accumulated other comprehensive earnings, net of tax 1,259,530 (1,580,976) 2,227,069 Retained earnings 32,603,153 33,680,702 32,787,406 Less: Unearned Employee Stock Ownership Plan shares at cost (2,989,065) (3,046,855) (3,281,220) Total equity 60,453,059 58,593,299 64,101,545 Total liabilities and equity

RESULTS EXAMINED Historical Book Value Per Share $18.40 $18.30 $18.20 $18.10 $18.00 $17.90 $17.80 $17.70 $17.60 $17.50 $17.40

CONTENTS Results Examined Growth Key Initiatives

GROWTH Positive Premium Growth $70,000,000 $60,000,000 $50,000,000 $40,000,000 $30,000,000 $20,000,000 $10,000,0002010 2011 2012 2013 2014 2015 2016 2017 2018 2019 Projected

GROWTH Geographic Expansion Currently Doing Business Licensed Only Application to be Filed

CONTENTS Results Examined Growth Key Initiatives

STRATEGIC INITIATIVES Efficiency Customer Experience Online Rating Auto-Renewal of Insurance Policies Real-Time Interface Rate Adequacy Improved Profitability

STRATEGIC INITIATIVES Average Premium Per Policy Average Premium by Line of Business Avg. BP Premium has increased by 40% while Avg. Exposure has increased by 12% since 2011 $7,000 $6,000 $5,000 $4,000 $3,000 $2,000 $1,000 $0 2011 2012 2013 2014 2015 2016 2017 2018 2019 Ql- Avg. BP Premium - Avg LL Premium - Avg. UL Premium -Avg. WC Premium -Avg Bldg & BPP Limit $1,200,000 $1,000,000 $800,000 $600,000 $400,000 $200,000 $0

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