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Intangible Assets - Summary of Changes in Intangible Assets (Details) - USD ($)
$ in Thousands
 12 Months Ended
Dec. 18, 2017
Dec. 31, 2017
Dec. 31, 2016
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Amortization   $ (3,700) $ (5,100)
Goodwill [Roll Forward]      
Goodwill, Beginning of the period   24,200 0
Goodwill, Additions (Disposals)   (18,800) 24,200
Goodwill, Impairment Loss   (1,500) 0
Goodwill, End of the Period   3,900 24,200
Intangible Assets and goodwill, Beginning of the period   79,600 18,200
Intangible Assets and Goodwill, Additions (Disposals)   (44,600) 66,500
Goodwill and Intangible Asset Impairment   (3,400) 0
Intangible Assets and goodwill, End of the period   27,900 79,600
Trade Mark      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   6,600 1,600
Intangible Assets acquired (disposed) $ (3,100)   5,500
Amortization   (500) (500)
Impairment of intangible assets (excluding goodwill)   (100) 0
Intangible Assets, End of the period   2,900 6,600
Insurance Licenses      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   16,700 16,600
Intangible Assets acquired (disposed)   0 100
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   26,200 0
Intangible Assets acquired (disposed) (21,800)   28,100
Amortization   (2,100) (1,900)
Impairment of intangible assets (excluding goodwill)   0 0
Intangible Assets, End of the period   2,300 26,200
Non-compete Agreements      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   3,300 0
Intangible Assets acquired (disposed) $ (900)   3,900
Amortization   (700) (600)
Impairment of intangible assets (excluding goodwill)   (1,000) 0
Intangible Assets, End of the period   700 3,300
Value of Business Acquired      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   0 0
Intangible Assets acquired (disposed)     1,800
Amortization     (1,800)
Impairment of intangible assets (excluding goodwill)     0
Intangible Assets, End of the period     0
Consulting Relationships      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   900 0
Intangible Assets acquired (disposed)   0 1,000
Amortization   (100) (100)
Impairment of intangible assets (excluding goodwill)   (800) 0
Intangible Assets, End of the period   0 900
Renewal Rights      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   1,700 0
Intangible Assets acquired (disposed)   0 1,900
Amortization   (300) (200)
Impairment of intangible assets (excluding goodwill)   0 0
Intangible Assets, End of the period   $ 1,400 $ 1,700