Intangible Assets and Goodwill (Tables)

12 Months Ended

Dec. 31, 2023

Goodwill and Intangible Assets Disclosure [Abstract]

Schedule of Intangible Assets

The following tables summarize intangible asset balances.

As of December 31, 2023	Weighted Average Useful Life (in years)	Intangible Assets, gross		Accumulated Amortization And Impairment		Intangible Assets, Net
Customer relationships	8	$	69,504	$	(24,153)	$	45,351
Acquired technology	5	36,041		(22,358)		13,683
Trademarks and tradenames	11	23,443		(6,701)		16,742
Non-compete agreements	3	616		(455)		161
Value of business acquired	1	400		(400)		—
Renewal rights	6	9,734		(3,415)		6,319
Insurance licenses	Indefinite	4,960		—		4,960
Total intangible assets		$	144,698	$	(57,482)	$	87,216

As of December 31, 2022	Weighted Average Useful Life (in years)	Intangible Assets, gross		Accumulated Amortization And Impairment		Intangible Assets, Net
Customer relationships	9	$	69,730	$	(15,079)	$	54,651
Acquired technology	5	37,932		(16,468)		21,464
Trademarks and tradenames	10	25,071		(5,724)		19,347
Non-compete agreements	3	619		(407)		212
Value of business acquired	1	400		(400)		—
Renewal rights	6	9,734		(2,113)		7,621
Insurance licenses	Indefinite	4,960		—		4,960
Total intangible assets		$	148,446	$	(40,191)	$	108,255

Schedule of Estimated Intangibles Amortization Expense

The following table shows estimated future intangible amortization expense for the next five years and thereafter.

Year ending December 31,	Estimated Amortization Expense
2024	$	18,439
2025	14,862
2026	10,201
2027	9,063
2028	8,347
Thereafter	21,344
	$	82,256

Summary of Changes in the Carrying Amount of Goodwill

The following table summarizes the changes in the carrying amount of goodwill:

Balance as of December 31, 2020	$	28,289
Acquisitions	197,365
Balance as of December 31, 2021	225,654
Acquisitions	38,064
Impairment loss (Insurance segment)	(43,758)
Purchase price adjustments(1)	24,737
Balance as of December 31, 2022, net of accumulated impairment of $43.8 million	244,697
Acquisition	2,421
Impairment loss (Insurance segment)	(55,211)
Balance as of December 31, 2023, net of accumulated impairment of $99.0 million	$	191,907

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(1)During the year ended December 31, 2022, we recorded an adjustment to the fair value of net assets previously acquired during the year ended December 31, 2021. See Note 12, Business Combinations, for more information.