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Revenue from Contracts with Customers - Disaggregation of Revenue (Details) - USD ($)
$ in Thousands
 12 Months Ended
Jun. 30, 2021
Jun. 30, 2020
Jun. 30, 2019
Disaggregation of Revenue [Line Items]      
Total revenue $ 937,815 $ 531,515 $ 337,469
Contract with customer, liabilities 5,080 1,738  
Marketing Development Funds      
Disaggregation of Revenue [Line Items]      
Contract with customer, liabilities 3,800    
Commission      
Disaggregation of Revenue [Line Items]      
Total revenue 826,606 476,606 296,000
Production bonus and other      
Disaggregation of Revenue [Line Items]      
Total revenue 111,209 54,909 41,469
Intersegment Eliminations      
Disaggregation of Revenue [Line Items]      
Total revenue 7,302 1,314 335
Intersegment Eliminations | Commission      
Disaggregation of Revenue [Line Items]      
Total revenue 2,004 534 335
Intersegment Eliminations | Production bonus and other      
Disaggregation of Revenue [Line Items]      
Total revenue 5,298 780 0
Senior      
Disaggregation of Revenue [Line Items]      
Total revenue 728,701 361,673 192,257
Senior | Commission      
Disaggregation of Revenue [Line Items]      
Total revenue 638,340 331,245 173,849
Senior | Medicare advantage      
Disaggregation of Revenue [Line Items]      
Total revenue 595,132 285,957 138,526
Senior | Medicare supplement      
Disaggregation of Revenue [Line Items]      
Total revenue 23,431 34,301 25,118
Senior | Prescription drug plan      
Disaggregation of Revenue [Line Items]      
Total revenue 1,652 2,867 3,209
Senior | Dental, vision, and health      
Disaggregation of Revenue [Line Items]      
Total revenue 15,969 7,758 4,470
Senior | Other commission revenue      
Disaggregation of Revenue [Line Items]      
Total revenue 2,156 362 2,526
Senior | Production bonus and other      
Disaggregation of Revenue [Line Items]      
Total revenue 90,361 30,428 18,408
Life      
Disaggregation of Revenue [Line Items]      
Total revenue 185,503 129,967 110,493
Life | Commission      
Disaggregation of Revenue [Line Items]      
Total revenue 162,649 107,864 89,246
Life | Core      
Disaggregation of Revenue [Line Items]      
Total revenue 79,666 75,236 76,135
Life | Final expense      
Disaggregation of Revenue [Line Items]      
Total revenue 78,764 30,592 11,057
Life | Ancillary      
Disaggregation of Revenue [Line Items]      
Total revenue 4,219 2,036 2,054
Life | Production bonus and other      
Disaggregation of Revenue [Line Items]      
Total revenue 22,854 22,103 21,247
Auto & Home      
Disaggregation of Revenue [Line Items]      
Total revenue 30,913 41,189 35,054
Auto & Home | Commission      
Disaggregation of Revenue [Line Items]      
Total revenue 27,621 38,031 33,240
Auto & Home | Production bonus and other      
Disaggregation of Revenue [Line Items]      
Total revenue $ 3,292 $ 3,158 $ 1,814