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Intangible Assets and Goodwill | 12 Months Ended
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Dec. 31, 2022
Intangible Assets and Goodwill |
Intangible Assets and Goodwill | 6. Intangible Assets and Goodwill Intangible Assets Intangible assets are stated at cost or acquisition-date fair value less accumulated amortization and impairment losses. Intangible assets consist of the following as of December 31, 2022: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | Weighted |  | ​ | ​ | ​ | Accumulated | ​ | ​ | ​
​ | ​ | Average | ​ | Intangible | ​ | Amortization | ​ | Intangible
​ | ​ | Useful Life | ​ | Assets, | ​ | And | ​ | Assets,
​ |  | (in years) |  | gross |  | Impairment |  | Net
Customer relationships |  | 9.0 | ​ | $ | 69,730 | ​ | $ | (15,079) | ​ | $ | 54,651
Acquired technology |  | 5.0 | ​ |  | 37,932 | ​ | ​ | (16,468) | ​ |  | 21,464
Trademarks and tradenames |  | 10.0 | ​ |  | 25,071 | ​ | ​ | (5,724) | ​ |  | 19,347
Non-compete agreements | ​ | 3.0 | ​ | ​ | 619 | ​ | ​ | (407) | ​ | ​ | 212
Value of business acquired | ​ | 1.0 | ​ | ​ | 400 | ​ | ​ | (400) | ​ | ​ | —
Renewal rights | ​ | 6.0 | ​ | ​ | 9,734 | ​ | ​ | (2,113) | ​ | ​ | 7,621
Insurance licenses | ​ | Indefinite | ​ | ​ | 4,960 | ​ | ​ | — | ​ | ​ | 4,960
Total intangible assets |  | ​ | ​ | $ | 148,446 | ​ | $ | (40,191) | ​ | $ | 108,255
​ Intangible assets consist of the following as of December 31, 2021: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | Weighted |  | ​ | ​ |  | ​ | ​ |  | ​ | ​
​ | ​ | Average | ​ | Intangible | ​ | ​ | ​ | ​ | Intangible
​ | ​ | Useful Life | ​ | Assets, | ​ | Accumulated | ​ | Assets,
​ |  | (in years) |  | gross |  | Amortization |  | Net
Customer relationships |  | 9.0 | ​ | $ | 56,810 | ​ | $ | (6,760) | ​ | $ | 50,050
Acquired technology |  | 5.0 | ​ |  | 48,135 | ​ | ​ | (10,095) | ​ |  | 38,040
Trademarks and tradenames |  | 12.0 | ​ |  | 25,389 | ​ | ​ | (2,587) | ​ |  | 22,802
Non-compete agreements | ​ | 2.0 | ​ | ​ | 450 | ​ | ​ | (251) | ​ | ​ | 199
Value of business acquired | ​ | 1.0 | ​ | ​ | 400 | ​ | ​ | (294) | ​ | ​ | 106
Renewal rights | ​ | 6.0 | ​ | ​ | 9,734 | ​ | ​ | (811) | ​ | ​ | 8,923
Trademarks and tradenames | ​ | Indefinite | ​ | ​ | 4,750 | ​ | ​ | — | ​ | ​ | 4,750
Insurance licenses | ​ | Indefinite | ​ | ​ | 4,960 | ​ | ​ | — | ​ | ​ | 4,960
Total intangible assets |  | ​ | ​ | $ | 150,628 | ​ | $ | (20,798) | ​ | $ | 129,830
​ During the third quarter of 2022, the Company recorded impairment charges of $17.7 million, primarily related to acquired technology, trademarks and tradenames, and customer relationships for certain asset groups within its Vertical Software segment. Impairment charges are included in impairment loss on intangible assets and goodwill in the consolidated statements of operations and comprehensive loss. There were no impairments of intangible assets during the years ended December 31, 2021 and 2020. Aggregate amortization expense related to intangibles was $23.8 million, $12.3 million, $2.9 million for the years ended December 31, 2022, 2021 and 2020, respectively. Estimated intangibles amortization expense for the next five years and thereafter consists of the following: ​
​ | ​ | ​ | ​
​ | ​ | Estimated
​ | ​ | Amortization
​ |  | Expense
2023 | ​ | $ | 19,992
2024 | ​ | ​ | 18,998
2025 |  | ​ | 15,140
2026 |  | ​ | 10,201
2027 |  | ​ | 9,090
Thereafter |  | ​ | 29,874
​ | ​ | $ | 103,295
​ Goodwill The following table summarizes the changes in the carrying amount of goodwill: ​
​ | ​ | ​ | ​
​ |  | Goodwill
Balance as of January 1, 2020 | ​ | $ | 18,274
Acquisitions | ​ | ​ | 10,176
Divestitures | ​ | ​ | (161)
Balance as of December 31, 2020 | ​ | ​ | 28,289
Acquisitions | ​ | ​ | 197,365
Balance as of December 31, 2021 | ​ | ​ | 225,654
Acquisitions | ​ | ​ | 38,064
Impairment loss | ​ | ​ | (43,758)
Purchase price adjustments(1) | ​ | ​ | 24,737
Balance as of December 31, 2022 | ​ | $ | 244,697
​ (1) During the year ended December 31, 2022, the Company recorded an adjustment to the fair value of net assets previously acquired during the year ended December 31, 2021. See Note 12. Business Combinations and Disposals for more information. During 2022, the Company recorded impairment charges of $43.7 million, related to its Insurance segment. Impairment charges are included in impairment loss on intangible assets and goodwill in the consolidated statements of operations and comprehensive loss. There were no impairments of goodwill during the years ended December 31, 2021 and 2020.

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