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Intangible Assets - Summary of Changes in Intangible Assets (Details) - USD ($)
$ in Thousands
 12 Months Ended
Dec. 18, 2017
Dec. 31, 2018
Dec. 31, 2017
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Amortization   $ (1,600) $ (3,700)
Goodwill [Roll Forward]      
Goodwill, Beginning of the period   3,900 24,200
Goodwill, Additions (Disposals)   0 (18,800)
Goodwill, Impairment Loss   0 (1,500)
Goodwill, End of the Period   3,900 3,900
Intangible Assets and goodwill, Beginning of the period   27,900 79,600
Intangible Assets and Goodwill, Additions (Disposals)   0 (44,600)
Goodwill and Intangible Asset Impairment   0 (3,400)
Intangible Assets and goodwill, End of the period   26,300 27,900
Trademarks      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   2,900 6,600
Intangible Assets acquired (disposed) $ 0   (3,100)
Amortization   (400) (500)
Impairment of intangible assets (excluding goodwill)   0 (100)
Intangible Assets, End of the period   2,500 2,900
Insurance Licenses      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   16,700 16,700
Intangible Assets acquired (disposed)   0 0
Amortization   0 0
Impairment of intangible assets (excluding goodwill)   0 0
Intangible Assets, End of the period   16,700 16,700
Agency Relationships      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   2,300 26,200
Intangible Assets acquired (disposed) 0   (21,800)
Amortization   (500) (2,100)
Impairment of intangible assets (excluding goodwill)   0 0
Intangible Assets, End of the period   1,800 2,300
Non-compete Agreements      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   700 3,300
Intangible Assets acquired (disposed) $ 0   (900)
Amortization   (300) (700)
Impairment of intangible assets (excluding goodwill)   0 (1,000)
Intangible Assets, End of the period   400 700
Consulting Relationships      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   0 900
Intangible Assets acquired (disposed)     0
Amortization     (100)
Impairment of intangible assets (excluding goodwill)     (800)
Intangible Assets, End of the period     0
Renewal Rights      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   1,400 1,700
Intangible Assets acquired (disposed)   0 0
Amortization   (400) (300)
Impairment of intangible assets (excluding goodwill)   0 0
Intangible Assets, End of the period   $ 1,000 $ 1,400