☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 1601 Dodge Street, Suite 3300, Omaha, Nebraska 68102 (Address of principal executive offices, Zip Code) Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant ...

Table of Contents BOSTON OMAHA CORPORATION and SUBSIDIARIES Notes to Consolidated Financial Statements For the Years Ended December 31, 2022 and 2021 We do not intend to pay dividends for the foreseeable future, and our stockholders will not be guaranteed, or have contractual or other rights, to receive dividends. Our Board of Directors may, in its discretion, modify or repeal our dividend policy or discontinue entirely the payment of dividends. The declaration and payment of dividends depends on various fa ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (MARK ONE) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38113 BOSTON OMAHA CORPORATION (Exact Name of Registrant as Specified in Its Charter) Delaware 27-0788438 (St ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (MARK ONE) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38113 BOSTON OMAHA CORPORATION (Exact Name of Registrant as Specified in Its Charter) Delaware 27-0788438 (State o ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (MARK ONE) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38113 BOSTON OMAHA CORPORATION (Exact Name of Registrant as Specified in Its Charter) Delaware 27-0788438 (State ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (MARK ONE) ☒ ANNUAL REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38113 BOSTON OMAHA CORPORATION (Exact name of registrant as specified in its charter) Delaware 27-0788438 (State or other jurisdic ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (MARK ONE) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38113 BOSTON OMAHA CORPORATION (Exact Name of Registrant as Specified in Its Charter) Delaware 27-0788438 (St ...

Billboard Operations - As of June 30, 2021, the company operates approximately 3,200 billboards with about 6,000 advertising faces, having increased its billboard count from approximately 2,900 through acquisitions[180] - Billboard revenues in the first half of fiscal 2021 increased by 8.9% compared to the same period in 2020, indicating a recovery from earlier pandemic-related declines[192] - The company plans to continue expanding its billboard operations and broadband services, as well as exploring acquisitions in other sectors[188] - Billboard rentals net revenue increased by 19.5% in the second quarter of fiscal 2021 compared to the same period in fiscal 2020[207] - In Q2 2021, net billboard revenues increased by 19.5% compared to Q2 2020, attributed to improved rental and occupancy rates post-COVID-19 and the acquisition of billboards from Thomas, contributing approximately 3.6% to revenues[246] - Billboard rentals increased by 8.9% in the first half of fiscal 2021 compared to the first half of fiscal 2020, with net revenues reaching $15,106,517[263] Broadband Services - The broadband services business serves over 17,000 customers across Arizona and Utah, with continued expansion planned in these regions[181] - Revenue from broadband services rose to $3,760,454 in the second quarter of fiscal 2021, up from $1,164,082 in the second quarter of fiscal 2020, primarily due to the UBB acquisition[208] - Broadband revenues reached $7,555,491, a significant increase compared to $1,431,333 in the previous year[278] - Net income attributable to common stockholders in the broadband segment was $369,367 in Q2 2021, up from $298,284 in Q2 2020[260] Insurance Operations - Surety insurance revenues decreased by 37.9%, or approximately $2.9 million, in the first half of fiscal 2021 compared to the first half of fiscal 2020 due to the cessation of rental insurance bonds[193] - The surety insurance business has expanded its licensing to all 50 states and the District of Columbia, enhancing its market reach[188] - Premiums earned from the UCS insurance subsidiary decreased by 45.8% in the second quarter of fiscal 2021 compared to the same period in fiscal 2020[208] - Total operating revenues for the insurance segment declined by 32.9% in Q2 2021 compared to Q2 2020, primarily due to the suspension of UCS's rental guarantee bond program[252] - Total operating revenues for the insurance segment declined by 37.9% in the first half of fiscal 2021 compared to the first half of fiscal 2020, totaling $4,722,892[269] - Insurance commissions increased by 88.3% in Q2 2021 compared to Q2 2020, driven by the ACS acquisition completed in April 2021[253] Financial Performance - The company generated positive cash flow from operating activities of approximately $5.3 million in the first half of fiscal 2021, up from $1.3 million in the same period in fiscal 2020[196] - Total revenues for the second quarter of fiscal 2021 were $14,179,881, a 23.4% increase from $11,492,564 in the second quarter of fiscal 2020[206] - Total revenues for the first half of fiscal 2021 were $27,384,900, representing a 19.6% increase from $22,902,744 in the first half of fiscal 2020[226] - Net income attributable to common stockholders for the second quarter of fiscal 2021 was $8,637,563, or $0.29 per share, compared to $3,402,308, or $0.14 per share, in the second quarter of fiscal 2020[223] - Net income attributable to common stockholders for the first half of fiscal 2021 was $93,075,190, or $3.26 per share, compared to a net loss of $21,331,930, or a loss of $0.89 per share, in the first half of fiscal 2020[243] Investments and Acquisitions - The company holds a 30% stake in Logic and approximately 49.9% in 24th Street Holding Co., with investments totaling $6 million in 24th Street Fund I and II[182] - The investment in Dream Finders Homes, which completed its IPO in January 2021, has shown increased business activity during the pandemic[195] - The company has invested approximately $19 million in CB&T Holding Corporation, focusing on subprime automobile lending, indicating a strategic investment in the financial services sector[184] - The company raised $58.6 million in gross proceeds from a public offering of Class A common stock in April 2021[197] - The company is resuming acquisition activities and capital project spending as business activity improves post-pandemic[199] Cash and Debt Management - The company had approximately $57 million in unrestricted cash and $132 million in U.S. Treasury trading securities as of June 30, 2021[286] - The company plans to finance future acquisitions and investments through cash, debt, and equity securities[286] - As of June 30, 2021, long-term debt included borrowings of $22,470,934, with $1,207,502 classified as current[289] - The company was in compliance with financial covenants, including a consolidated leverage ratio not greater than 3.50 to 1.00 as of June 30, 2021[290] - The existing credit facility imposes restrictions that could limit the company's ability to incur additional indebtedness, make acquisitions, or pay dividends, which may increase vulnerability to adverse economic conditions[301] Operational Costs - Total costs and expenses for the second quarter of fiscal 2021 were $15,273,353, an increase from $12,357,873 in the second quarter of fiscal 2020[212] - Employee costs increased by $1,428,234 in the second quarter of fiscal 2021, mainly due to the UBB acquisition[215] - Total costs and expenses for the first half of fiscal 2021 were $29,964,150, an increase of 20.4% from $24,948,025 in the first half of fiscal 2020[232] - Employee costs rose by $2,537,236, driven by acquisitions, increasing from $6,230,960 in the first half of fiscal 2020 to $8,768,196 in the first half of fiscal 2021[235] Market Risks and Compliance - The company held no significant derivative instruments as of June 30, 2021, indicating minimal exposure to market risks related to interest rates, foreign currency, or commodity prices[308] - The company is at risk of being deemed an investment company under the Investment Company Act if a significant portion of its assets consists of investments in companies where it holds less than a majority interest[302] - The preparation of financial statements requires estimates that may differ from actual results, influenced by factors such as the COVID-19 pandemic[310]

Business Operations - As of March 31, 2021, the company operates approximately 3,200 billboards with around 6,000 advertising faces, having increased its billboard count through acquisitions since 2015[173] - The broadband services business serves over 17,000 customers across Arizona and Utah, with continued expansion planned in these regions[175] - The company plans to continue acquiring billboard assets and expanding broadband services, as well as making additional investments in real estate management services[182] - Billboard revenues in the first quarter of fiscal 2021 were down only 0.9% from the same period in 2020, indicating a return to normal levels[187] - Billboard rentals decreased by 0.9% to $7,153,685 in Q1 2021, accounting for 54.2% of total revenues, while broadband services revenue surged to $3,795,037, up from $267,251 in Q1 2020[202][203] Financial Performance - Total revenues for Q1 2021 were $13,205,019, representing a 15.7% increase from $11,410,180 in Q1 2020, largely driven by the acquisition of FibAire[201] - The net loss from operations for Q1 2021 was $1,485,778, or 11.3% of total revenues, compared to a net loss of $1,179,972, or 10.3% of total revenues in Q1 2020[214] - In Q1 fiscal 2021, the company reported net income attributable to common stockholders of $84,437,627, or $3.09 per share, compared to a net loss of $24,734,238, or a loss of $1.05 per share in Q1 fiscal 2020[216] - The company generated positive cash flow from operating activities of approximately $4.0 million in Q1 2021, compared to negative cash flow of approximately $0.1 million in Q1 2020[191] - Net income attributable to common stockholders was $637,060, or 16.8% of revenues, up from $58,869, or 22.0% in the prior year[233] Insurance Segment - Surety insurance revenues decreased by 48.3%, approximately $1.7 million, in the first quarter of fiscal 2021 compared to the same period in fiscal 2020 due to the cessation of rental insurance bonds[188] - Premiums earned from the UCS insurance subsidiary fell by 48.3% to $1,786,564 in Q1 2021, primarily due to the suspension of new bonds under the rental guarantee bond program[203] - The company’s insurance segment reported a loss from operations of $787,487 in Q1 fiscal 2021, significantly impacted by increased losses and loss adjustment expenses[229] - Total operating revenues for the insurance segment declined by 42.5% in Q1 fiscal 2021 compared to Q1 fiscal 2020, attributed to the same suspension of the rental guarantee bond program[226] Investments and Acquisitions - The company invested $10 million in Dream Finders Homes, which successfully completed its initial public offering in January 2021[177] - The company holds approximately 20% of the issued and outstanding common stock of Yellowstone, a SPAC focused on acquiring businesses in various industries[180] - The company acquired 238 billboard structures and related assets for $6,108,508 during the first three months of fiscal 2021[237] - The company plans to continue acquiring billboard locations and insurance businesses, financing future acquisitions with cash, debt, and third-party financing[241] - The company may need to seek additional capital through long-term debt borrowings or the sale of securities if significant acquisition opportunities arise beyond current cash and U.S. Treasury securities[255] Cash and Liquidity - As of March 31, 2021, the company had approximately $84 million in unrestricted cash and $54 million in U.S. Treasury trading securities[241] - The company raised $58.6 million in gross proceeds from a public offering of Class A common stock in April 2021, ensuring adequate financial resources for future expansion and acquisition opportunities[192] - Net cash provided by operating activities was $4,029,984 for the first three months of fiscal 2021, compared to a net cash outflow of $110,884 in the same period of fiscal 2020[236] - Net cash provided by investing activities was $36,047,823, consistent with the previous year's figure of $36,047,823[237] Cost Management - Total costs and expenses increased to $14,690,797 in Q1 2021, up from $12,590,152 in Q1 2020, with total costs as a percentage of total revenues rising from 110.3% to 111.3%[206] - Employee costs rose by $1,109,002 to $4,242,147 in Q1 2021, driven by the addition of the broadband services business[209] - Employee costs in the billboard segment decreased by 2.6% in Q1 fiscal 2021 compared to Q1 fiscal 2020[222] - Total cost of revenues decreased to $756,213, representing 19.9% of operating revenues, compared to 28.2% in the first three months of fiscal 2020[233] Market Conditions and Risks - The company has taken steps to avoid being deemed an investment company under the Investment Company Act, including selling marketable securities and acquiring non-investment assets[257] - The company is in compliance with financial covenants under its Credit Agreement, including a consolidated leverage ratio of not greater than 3.50 to 1.00[245] - The company’s credit facility imposes restrictions that could limit its ability to incur additional indebtedness or make acquisitions[256] - As of March 31, 2021, the company held no significant derivative instruments that materially increased exposure to market risks[263]

Business Operations - The company operates three main business lines: outdoor billboard advertising, surety insurance, and broadband services, with a focus on acquiring additional billboard assets[22] - As of March 26, 2021, the company operates approximately 3,200 billboards with around 6,000 advertising faces, having increased its billboard count through acquisitions[24] - The surety insurance business has expanded its licensing to all 50 states and the District of Columbia since acquiring United Casualty and Surety Insurance Company in December 2016[27] - AireBeam, a subsidiary, provides high-speed fixed wireless internet service to over 7,000 subscribers in southern Arizona and is building a fiber-to-the-home network[29] Financial Performance and Investments - The company anticipates continued losses for the foreseeable future, which may impact its financial condition and results of operations[13] - The company aims to grow intrinsic value per share by retaining capital for reinvestment and exploring new investment opportunities[40] - The company has made significant minority investments, including $10 million in Dream Finders Holdings LLC and $19 million in CB&T Holding Corporation, focusing on sectors like homebuilding and subprime automobile lending[34][35] - The company has spent over $280 million on acquisitions in outdoor billboard advertising, surety insurance, and broadband services since June 2015[58] - The company has engaged in acquisitions and minority investments totaling $423,648,471 since management took over in 2015, funded by equity investments and debt conversions[86] Acquisitions - Boston Omaha Corporation acquired approximately 3,200 billboard structures with around 6,000 advertising faces for over $190 million[59] - The company paid approximately $19.4 million for the acquisition of one insurance company and four insurance brokerage firms since September 2015[60] - AireBeam was acquired for $12.3 million, providing high-speed internet to over 7,000 subscribers in underserved Arizona communities[61] - UBB was acquired for $21.3 million, serving over 10,000 subscribers in Salt Lake City and surrounding areas[61] - The company acquired substantially all assets of FibAire and UBB, broadband service providers located in Arizona and Utah, respectively, in March and December 2020[89] Market Conditions and Competition - The outdoor billboard advertising market was estimated at $4.7 billion in the U.S. in 2020, with additional outdoor advertising solutions accounting for approximately $1.4 billion[77] - The surety market was estimated at $6.9 billion based on 2019 industry reports, with the company acquiring four surety brokerage firms to enhance its revenue streams[80] - The outdoor advertising industry is highly competitive, with major players generating over 50% of total industry revenues[107] - The company faces intense competition in the outdoor billboard advertising industry from larger companies, which may impact its advertising revenues and market share[209] Financial Strategy and Capital Needs - The company anticipates needing to raise additional financing for significant acquisitions and investments in the future[151] - The company may issue shares of common stock in connection with future acquisitions, which could lead to substantial dilution of existing stockholders[156] - The company may need to rely on additional equity issuances, which could dilute shareholders, or costly debt financings that reduce available funds for operations[208] - The company is subject to risks associated with significant indebtedness, including the potential inability to refinance debts on favorable terms[203] Regulatory and Operational Risks - The company has faced risks related to acquisitions, including the potential inability to successfully integrate acquired businesses[13] - GIG and its subsidiaries are subject to regulation in all 50 U.S. states and the District of Columbia, with varying degrees of regulatory oversight related to solvency standards, licensing, and market conduct[125] - The company may inadvertently be deemed an investment company under the Investment Company Act, which could impose significant operational restrictions[188] - The company may need to sell assets at unattractive prices to remain compliant with the Investment Company Act, which could adversely affect its financial condition[188] Debt and Financing - As of December 31, 2020, the company had long-term debt of $23,057,650, with $1,282,504 classified as current[148] - The company reported a net loss from operations of $4.0 million for the fiscal year ended December 31, 2020, compared to a net loss of $12.4 million for the fiscal year ended December 31, 2019[163] - The company may incur additional indebtedness under future credit facilities, which could include restrictive covenants that may adversely affect its financial condition[201] - Future debt financing arrangements may contain covenants that, if not complied with, could materially affect the company's ability to meet its debt obligations[200] Employee and Operational Structure - As of March 1, 2021, the company had 217 employees, with the majority in billboard and broadband operations[111] - The company has limited experience in the day-to-day operations of the industries in which it operates, which may affect operational efficiency[174]