Acquisition and Discontinued Operations - Discontinued Operations (Details) $ in Thousands	3 Months Ended				6 Months Ended		12 Months Ended
	Mar. 31, 2020 USD ($)	Jun. 30, 2019 USD ($)	Mar. 31, 2019 USD ($) claim	Jun. 30, 2018 USD ($)	Jun. 30, 2019 USD ($)	Jun. 30, 2018 USD ($)	Dec. 31, 2018 USD ($)	Dec. 31, 2019 USD ($)	Oct. 18, 2018 USD ($)	Apr. 01, 2015
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net		$ 0		$ (6,628)	$ 0	$ (6,628)
Final aggregate purchase price				1,700		1,700
Mendota
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net		$ (8,000)					$ (8,500)
Final aggregate purchase price									$ 28,600
Escrow deposit									$ 5,000
Maximum obligation				$ 2,500		$ 2,500
Number of claims settled | claim			1
Indemnification claim settled			$ 500
Mendota | Forecast
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Estimated net loss								$ 1,600
Released escrow deposit	$ 3,400
Discontinued Operations
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net							$ 1,300
Future earnout payments, as a percentage of written premium and fee income										1.25%