X0407 4 2023-05-05 0001290677 Turning Point Brands, Inc. TPB 0001794878 Purdy Graham 5201 INTERCHANGE WAY LOUISVILLE KY 40229 true President & CEO false Common Stock 2023-05-05 4 A 0 26966 22.25 A 173812 D Options (2022) 30.46 2032-03-14 Common Stock 12000 12000 D Options (2021) 51.75 2031-02-18 Common Stock 9000 9000 D Options (2020) 14.85 2030-03-18 Common Stock 11000 11000 D Options (2019) 47.58 2029-03-20 Common Stock 5500 5500 D Options (2018) 21.21 2028-03-07 Common Stock 8900 8900 D Options (2017) 15.41 2027-05-17 Common Stock 5000 5000 D Options (2014) 3.83 2024-08-08 Common Stock 5216 5216 D Granted pursuant to the issuer's 2006 Equity Plan Granted pursuant to the issuer's 2021 Equity Incentive Plan. The options vested and became exercisable as to 50% of the underlying shares on August 8, 2014, 25% of the underlying shares on August 8, 2015 and 25% of the underlying shares on August 8, 2016. Granted pursuant to the issuer's 2015 Equity Incentive Plan. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2018, 33% of the underlying shares on January 1, 2019 and 33% of the underlying shares on January 1, 2020. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2019, 33% of the underlying shares on January 1, 2020 and 33% of the underlying shares on January 1, 2021. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2020, 33% of the underlying shares on January 1, 2021 and 33% of the underlying shares on January 1, 2022. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2021, 33% of the underlying shares on January 1, 2022, and 33% of the underlying shares on January 1, 2023. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2022, 33% of the underlying shares on January 1, 2023, and 33% of the underlying shares on January 1, 2024. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2023, 33% of the underlying shares on January 1, 2024, and 33% of the underlying shares on January 1, 2025. Represents grant of restricted stock units ("RSUs") pursuant to the issuer's 2021 Equity Incentive Plan. These RSUs will vest 33% on the first, second and third anniversaries of March 31, 2023. RSUs convert into shares of Common Stock on a 1-for-1 basis. The total reported in Column 5 includes 29,466 restricted stock units and 144,346 shares of common stock. /s/ Graham Purdy 2023-05-09