Intangible Assets and Goodwill - Carrying Amounts of Goodwill and Intangible Assets (Details) - USD ($) $ in Thousands	6 Months Ended
	Dec. 31, 2021	Dec. 31, 2020	Jun. 30, 2021
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	$ 46,756		$ 46,386
Accumulated Amortization	(9,029)		(5,716)
Net Carrying Amount	$ 37,727		40,670
Weighted-Average Remaining Useful Life	6 years 7 months 6 days	7 years 1 month 6 days
Goodwill	$ 73,732		68,019
Auto & Home
Finite-Lived Intangible Assets [Line Items]
Goodwill	5,364		5,364
Senior
Finite-Lived Intangible Assets [Line Items]
Goodwill	68,368		62,655
Customer relationships
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	17,492		17,122
Accumulated Amortization	(4,817)		(3,448)
Net Carrying Amount	12,675		13,674
Trade Name
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	2,680		2,680
Accumulated Amortization	(893)		(625)
Net Carrying Amount	1,787		2,055
Proprietary Software
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	1,592		1,592
Accumulated Amortization	(601)		(382)
Net Carrying Amount	991		1,210
Non-compete agreements
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	1,292		1,292
Accumulated Amortization	(303)		(163)
Net Carrying Amount	989		1,129
Vendor relationships
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	23,700		23,700
Accumulated Amortization	(2,415)		(1,098)
Net Carrying Amount	$ 21,285		$ 22,602