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Business Combinations - Schedule of Business Acquisitions (Details) - USD ($)
$ in Thousands
6 Months Ended
Jun. 30, 2020
Jun. 30, 2019
Jun. 01, 2020
May 01, 2020
Apr. 01, 2020
Jan. 01, 2020
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid $ 231,737          
Fair value of contingent earnout consideration 25,188 $ 25,619        
Fair value of equity interest 52,130 $ 31,963        
Business Combination, Consideration Transferred, Liabilities Incurred 300          
Total consideration 309,355          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash 7,625          
Premiums, commissions and fees receivable 26,763          
Property and equipment 444          
Other assets 230          
Goodwill 171,056          
Total assets acquired 330,464          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable (19,715)          
Accrued expenses and other current liabilities (1,394)          
Total liabilities acquired (21,109)          
Net assets acquired 309,355          
Maximum potential contingent earnout consideration (1) 127,528          
Lanier            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid 24,450          
Fair value of contingent earnout consideration 1,628          
Fair value of equity interest 6,119          
Total consideration 32,197          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash           $ 2,413
Premiums, commissions and fees receivable           2,494
Property and equipment           294
Other assets           168
Goodwill           23,739
Total assets acquired           35,416
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable           (2,954)
Accrued expenses and other current liabilities           (265)
Total liabilities acquired           (3,219)
Net assets acquired           32,197
Maximum potential contingent earnout consideration (1)           11,000
Highland            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid 6,603          
Fair value of contingent earnout consideration 788          
Fair value of equity interest 4,500          
Total consideration 11,891          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash           1,542
Premiums, commissions and fees receivable           5,977
Property and equipment           0
Other assets           13
Goodwill           4,228
Total assets acquired           19,133
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable           (6,374)
Accrued expenses and other current liabilities           (868)
Total liabilities acquired           (7,242)
Net assets acquired           11,891
Maximum potential contingent earnout consideration (1)           2,450
IRP            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid 26,223          
Fair value of contingent earnout consideration 5,521          
Fair value of equity interest 7,535          
Total consideration $ 39,279          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash         $ 1,694  
Premiums, commissions and fees receivable         3,229  
Property and equipment         123  
Other assets         22  
Goodwill         30,250  
Total assets acquired         43,580  
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable         (4,301)  
Accrued expenses and other current liabilities         0  
Total liabilities acquired         (4,301)  
Net assets acquired         39,279  
Maximum potential contingent earnout consideration (1)         44,399  
Compound annual revenue growth rate 50.00%          
Period to which compound annual revenue growth rate has been applied 3 years          
Rosenthal            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid $ 75,936          
Fair value of contingent earnout consideration 7,051          
Fair value of equity interest 10,147          
Total consideration 93,134          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash     $ 954      
Premiums, commissions and fees receivable     4,734      
Property and equipment     0      
Other assets     11      
Goodwill     56,253      
Total assets acquired     96,561      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable     (3,427)      
Accrued expenses and other current liabilities     0      
Total liabilities acquired     (3,427)      
Net assets acquired     93,134      
Maximum potential contingent earnout consideration (1)     30,843      
TBA/RBA            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid 76,272          
Fair value of contingent earnout consideration 7,000          
Fair value of equity interest 21,427          
Business Combination, Consideration Transferred, Liabilities Incurred 300          
Total consideration 104,999          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash     0      
Premiums, commissions and fees receivable     8,731      
Property and equipment     0      
Other assets     0      
Goodwill     44,264      
Total assets acquired     107,074      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable     (2,075)      
Accrued expenses and other current liabilities     0      
Total liabilities acquired     (2,075)      
Net assets acquired     104,999      
Maximum potential contingent earnout consideration (1)     30,147      
All Others            
Business Combination, Consideration Transferred [Abstract]            
Cash consideration paid 22,253          
Fair value of contingent earnout consideration 3,200          
Fair value of equity interest 2,402          
Total consideration 27,855          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Cash       $ 1,022    
Premiums, commissions and fees receivable       1,598    
Property and equipment       27    
Other assets       16    
Goodwill       12,322    
Total assets acquired       28,700    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]            
Premiums and producer commissions payable       (584)    
Accrued expenses and other current liabilities       (261)    
Total liabilities acquired       (845)    
Net assets acquired       27,855    
Maximum potential contingent earnout consideration (1)       8,689    
Purchased customer accounts            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets 107,133          
Purchased customer accounts | Lanier            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           6,308
Purchased customer accounts | Highland            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Purchased customer accounts | IRP            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets         8,262  
Purchased customer accounts | Rosenthal            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     33,670      
Purchased customer accounts | TBA/RBA            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     53,900      
Purchased customer accounts | All Others            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets       4,993    
Distributor relationships            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets 14,600          
Distributor relationships | Lanier            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Distributor relationships | Highland            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           6,500
Distributor relationships | IRP            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets         0  
Distributor relationships | Rosenthal            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Distributor relationships | TBA/RBA            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Distributor relationships | All Others            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets       8,100    
Carrier relationships            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets 659          
Carrier relationships | Lanier            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Carrier relationships | Highland            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           659
Carrier relationships | IRP            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets         0  
Carrier relationships | Rosenthal            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Carrier relationships | TBA/RBA            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Carrier relationships | All Others            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets       0    
Software            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets 565          
Software | Lanier            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Software | Highland            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Software | IRP            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets         0  
Software | Rosenthal            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Software | TBA/RBA            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     0      
Software | All Others            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets       565    
Trade names            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets $ 1,389          
Trade names | Lanier            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           0
Trade names | Highland            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets           $ 214
Trade names | IRP            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets         $ 0  
Trade names | Rosenthal            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     939      
Trade names | TBA/RBA            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets     $ 179      
Trade names | All Others            
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]            
Intangible assets       $ 57