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Debt - Narrative (Details) - USD ($)
3 Months Ended 6 Months Ended
Apr. 07, 2020
Apr. 01, 2019
Dec. 03, 2018
Jun. 30, 2020
Mar. 31, 2020
Jun. 30, 2019
Jun. 30, 2020
Jun. 30, 2019
Dec. 31, 2019
Dec. 23, 2019
Mar. 31, 2019
Dec. 31, 2018
Jun. 15, 2018
May 11, 2018
Debt Instrument                            
Fair value investments       $ 2,656,900,000   $ 2,483,000,000.0 $ 2,656,900,000 $ 2,483,000,000.0 $ 2,746,000,000.0     $ 2,328,700,000    
Total debt       349,800,000     349,800,000   283,500,000          
Total commitment under revolving credit facility $ 291.4       $ 234,000,000.0                  
Repayments of debt             (1,100,000) (21,700,000)            
NSM Bank Facility                            
Debt Instrument                            
Face amount                           $ 100,000,000.0
Other Operations                            
Debt Instrument                            
Total commitment under revolving credit facility       16,300,000     16,300,000              
NSM Holding Co LLC                            
Debt Instrument                            
Total debt       268,400,000     268,400,000   219,200,000          
NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total debt       267,000,000.0     267,000,000.0   217,400,000          
Face amount       $ 273,400,000 220,700,000 222,300,000 $ 273,400,000 222,300,000 $ 221,300,000   $ 186,400,000 $ 180,400,000    
Percentage of discounted future cash flows             10.00%              
Debt, weighted average interest rate, all-in       7.21%     7.21%   6.60%          
Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                   $ 124,000,000.0        
Kudu | Kudu Debt [Member]                            
Debt Instrument                            
Total debt       $ 70,800,000     $ 70,800,000   $ 53,600,000          
Term Loan | Other Operations                            
Debt Instrument                            
Total commitment under revolving credit facility       11,300,000     11,300,000              
Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Face amount 276,400,000     $ 273,400,000 224,000,000.0   $ 273,400,000   $ 221,300,000          
Effective percentage       7.20%     7.20%   7.50%          
Unamortized issuance cost       $ (6,400,000)     $ (6,400,000)   $ (3,900,000)          
Repayments of debt       0   (500,000) (600,000) (1,000,000.0)            
Proceeds from borrowings       52,400,000   42,900,000 52,400,000 42,900,000            
Debt Instrument, Increase (Decrease), Other, Net       300,000   0 300,000 0            
Term Loan | NSM Holding Co LLC | Other NSM                            
Debt Instrument                            
Total debt       1,400,000     1,400,000   $ 1,800,000          
Face amount       $ 1,600,000     $ 1,600,000              
Effective percentage       3.20%     3.20%   3.00%          
Term Loan | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Face amount       $ 74,000,000.0     $ 74,000,000.0   $ 57,000,000.0          
Total commitment under revolving credit facility                   57,000,000.0        
Proceeds from Issuance of Long-term Debt       $ 5,000,000.0     $ 17,000,000.0              
Term Loan | Kudu | Kudu Debt [Member]                            
Debt Instrument                            
Effective percentage       8.10%     8.10%   8.30%          
Unamortized issuance cost       $ (3,200,000)     $ (3,200,000)   $ (3,400,000)          
Term Loan | Other | Other                            
Debt Instrument                            
Total debt       10,600,000     10,600,000   10,700,000          
Face amount       $ 10,900,000     $ 10,900,000   $ 11,100,000          
Effective percentage       9.30%     9.30%   8.30%          
Unamortized issuance cost       $ (300,000)     $ (300,000)   $ (400,000)          
Delayed Draw Term Loans [Member] | Other Operations                            
Debt Instrument                            
Total commitment under revolving credit facility       3,000,000.0     3,000,000.0              
Delayed Draw Term Loans [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                   62,000,000.0        
Delayed Draw Term Loans [Member] | Kudu | Kudu Debt [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                 125,000,000.0          
Revolving Credit Facility | Other Operations                            
Debt Instrument                            
Total commitment under revolving credit facility       2,000,000.0     2,000,000.0              
Revolving Credit Facility | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total commitment under revolving credit facility 15,000,000.0       $ 10,000,000.0                  
Repayments of debt       0   (6,500,000) 0 (6,500,000)            
Proceeds from borrowings       $ 0   0 $ 0 6,500,000            
Revolving Credit Facility | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                   $ 5,000,000.0        
Interest Rate Swap | NSM Holding Co LLC                            
Debt Instrument                            
Derivative, fixed interest rate                         2.97%  
Derivative, variable interest rate       0.17%     0.17%              
Interest Rate Swap | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total debt       $ 148,400,000     $ 148,400,000              
Total commitment under revolving credit facility                         $ 151,000,000.0  
Hedged Liability, Fair Value Hedge                         $ 151,000,000.0  
Derivative, fixed interest rate         2.97%                  
Debt, weighted average interest rate, all-in       6.78%     6.78%              
London Interbank Offered Rate (LIBOR) | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             1.00%              
London Interbank Offered Rate (LIBOR) | Minimum | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Debt Instrument, Interest Rate, Increase (Decrease)             1.00%              
Basis spread on variable rate         4.25%   5.50%              
London Interbank Offered Rate (LIBOR) | Minimum | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             5.50%              
London Interbank Offered Rate (LIBOR) | Maximum | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Debt Instrument, Interest Rate, Increase (Decrease)             1.25%              
Basis spread on variable rate         4.75%   6.00%              
London Interbank Offered Rate (LIBOR) | Maximum | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             6.25%              
Prime Rate | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             1.00%              
Prime Rate | Minimum | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             4.50%              
Prime Rate | Maximum | Line of Credit [Member] | Kudu | Kudu Bank Facility [Member]                            
Debt Instrument                            
Basis spread on variable rate             5.25%              
Designated as Hedging Instrument | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Debt, weighted average interest rate, all-in       6.67%     6.67%              
Designated as Hedging Instrument | Interest Rate Swap | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total debt       $ 148,400,000     $ 148,400,000              
Debt, weighted average interest rate, all-in       8.72%     8.72%              
Not Designated as Hedging Instrument | Interest Rate Swap | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total debt       $ 125,000,000.0     $ 125,000,000.0              
Effective percentage       6.90%     6.90%              
Kingsbridge [Member] | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Proceeds from borrowings       $ 52,400,000                    
Embrace | NSM Holding Co LLC                            
Debt Instrument                            
Proceeds from borrowings   $ 20,400,000                        
Embrace | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Proceeds from borrowings           $ 20,400,000                
KBK Insurance Group, Inc. & KBK Premium Services, Inc.                            
Debt Instrument                            
Proceeds from borrowings     $ 30,100,000                      
Renewal Rights | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Proceeds from borrowings               $ 22,500,000            
Carrying Value | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Total debt       267,000,000.0     $ 267,000,000.0   217,400,000          
Debt securities issued by corporations                            
Debt Instrument                            
Fair value investments       505,800,000     505,800,000   467,200,000          
Debt securities issued by corporations | AAA                            
Debt Instrument                            
Fair value investments       8,300,000     8,300,000   9,500,000          
Debt securities issued by corporations | AA                            
Debt Instrument                            
Fair value investments       53,600,000     53,600,000   73,900,000          
Debt securities issued by corporations | Standard & Poor's, A Rating [Member]                            
Debt Instrument                            
Fair value investments       314,100,000     314,100,000   288,500,000          
Debt securities issued by corporations | BBB                            
Debt Instrument                            
Fair value investments       128,100,000     128,100,000   95,300,000          
Debt securities issued by corporations | BB                            
Debt Instrument                            
Fair value investments       $ 1,700,000     $ 1,700,000   $ 0          
United Kingdom, Pounds | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Face amount 42,500,000                          
United Kingdom, Pounds | London Interbank Offered Rate (LIBOR) | Minimum | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Basis spread on variable rate             6.00%              
United Kingdom, Pounds | London Interbank Offered Rate (LIBOR) | Maximum | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Debt Instrument, Interest Rate, Increase (Decrease)             1.25%              
Basis spread on variable rate             6.50%              
Derivative, Cap Interest Rate       1.25%     1.25%              
United Kingdom, Pounds | Kingsbridge [Member] | NSM Holding Co LLC                            
Debt Instrument                            
Proceeds from borrowings 42,500,000                          
United States of America, Dollars | Term Loan | NSM Holding Co LLC | NSM Bank Facility                            
Debt Instrument                            
Face amount 52,400,000                          
United States of America, Dollars | Kingsbridge [Member] | NSM Holding Co LLC                            
Debt Instrument                            
Proceeds from borrowings $ 52,400,000