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Intangible Assets and Goodwill - Summary of Changes in Intangible Assets (Details) - USD ($)
$ in Millions
 3 Months Ended
Jan. 19, 2016
Mar. 31, 2018
Mar. 31, 2017
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Amortization   $ (0.4) $ (0.9)
Goodwill [Roll Forward]      
Goodwill, Beginning of the period   3.9 24.2
Goodwill, Additions   0.0 1.8
Goodwill, End of the period   3.9 26.0
Intangible assets and goodwill, Beginning of the period   27.9 79.6
Intangible Assets and Goodwill, Acquired   0.0 1.8
Intangible assets and goodwill, End of the period   27.5 80.5
Trade Mark      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   2.9 6.6
Intangible Assets, Additions   0.0 0.0
Amortization   (0.1) (0.2)
Intangible Assets, End of the period $ 4.0 2.8 6.4
Insurance Licenses      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   16.7 16.7
Intangible Assets, Additions   0.0 0.0
Amortization   0.0 0.0
Intangible Assets, End of the period   16.7 16.7
Agency Relationships      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   2.3 26.2
Intangible Assets, Additions   0.0 0.0
Amortization   (0.1) (0.4)
Intangible Assets, End of the period 25.0 2.2 25.8
Non-compete Agreements      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   0.7 3.3
Intangible Assets, Additions 2.9 0.0 0.0
Amortization   (0.1) (0.2)
Intangible Assets, End of the period   0.6 3.1
Consulting Relationships      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   0.0 0.9
Intangible Assets, Additions   0.0 0.0
Amortization   0.0 0.0
Intangible Assets, End of the period $ 1.0 0.0 0.9
Contractual Rights      
Finite and Indefinite Lived Intangible Assets [Roll Forward]      
Intangible Assets, Beginning of the period   1.4 1.7
Intangible Assets, Additions   0.0 0.0
Amortization   (0.1) (0.1)
Intangible Assets, End of the period   $ 1.3 $ 1.6