AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I.

SEC source: 0000351040-24-000013 · primary_doc.xml · nonDerivative · entry 1

AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. · CIK 0000351040 · Director · 10% owner · See Remarks

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,700,761

F1 · kind: The shares were sold in connection with an underwritten public offering of the Issuer's Common Stock (including pursuant to the underwriters' exercise of their over-allotment option) at a net price per share of $27.695, after underwriting discounts and commissions.

F1 · price: The shares were sold in connection with an underwritten public offering of the Issuer's Common Stock (including pursuant to the underwriters' exercise of their over-allotment option) at a net price per share of $27.695, after underwriting discounts and commissions.

F2 · balance_after: Includes 117,679 shares that were distributed to American Family Mutual Insurance Company, S.I. ("AFMIC") in connection with the dissolution of Bowhead Insurance Holdings LP.

F3 · ownership.direct: GPC Partners Investments (SPV III) LP ("GPC") and AMFIC are parties to a Voting Agreement, dated May 22, 2024, and each may be deemed to be members of a "group," as defined in Rule 13d-5 of the Securities Exchange Act of 1934, as amended. The share ownership reported herein does not include any shares owned by GPC, and AFMIC disclaims membership in a group with GPC and disclaims beneficial ownership of any shares owned by GPC.

SEC source: 0000351040-24-000010 · primary_doc.xml · nonDerivative · entry 1

AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. · CIK 0000351040 · Director · 10% owner · See Remarks

10b5-1 filing: No plan indicated

Ownership: Indirect · (1)

Disclosed balance after: 6,061,081

F1 · kind: American Family Mutual Insurance Company, S.I.'s (AFMIC) pecuniary interest in the shares is held through its limited partnership interest in Bowhead Insurance Holdings LP (BIHL), which directly owns the shares.

F2 · kind: In light of the performance of the Issuer's common stock following its initial public offering, the limited partnership agreement of BIHL was amended to adjust upward the number of shares of common stock to be distributed to the holders of BIHL Class P interests upon dissolution of BIHL, thereby reducing the number of shares to be distributed to the holders of BIHL Class A interests (including AMFIC) upon dissolution. This number is subject to adjustment based on the actual number of shares of Issuer common stock distributed after accounting for costs associated with the dissolution of BIHL

F2 · price: In light of the performance of the Issuer's common stock following its initial public offering, the limited partnership agreement of BIHL was amended to adjust upward the number of shares of common stock to be distributed to the holders of BIHL Class P interests upon dissolution of BIHL, thereby reducing the number of shares to be distributed to the holders of BIHL Class A interests (including AMFIC) upon dissolution. This number is subject to adjustment based on the actual number of shares of Issuer common stock distributed after accounting for costs associated with the dissolution of BIHL

F3 · balance_after: GPC Partners Investments (SPV III) LP ("GPC") and AMFIC are parties to a Voting Agreement, dated May 22, 2024, and each may be deemed to be members of a "group," as defined in Rule 13d-5 of the Securities Exchange Act of 1934, as amended. The share ownership reported herein does not include any shares owned by GPC, and AFMIC disclaims membership in a group with GPC and disclaims beneficial ownership of any shares owned by GPC.

F1 · ownership.nature: American Family Mutual Insurance Company, S.I.'s (AFMIC) pecuniary interest in the shares is held through its limited partnership interest in Bowhead Insurance Holdings LP (BIHL), which directly owns the shares.

SEC source: 0000351040-24-000009 · primary_doc.xml · derivative · entry 2

AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. · CIK 0000351040 · Director · 10% owner · See Remarks

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 816,471

Underlying: Common Stock · 28,236 shares

Expires 2029-05-22

F4 · security: Pursuant to a Call Option Agreement, dated May 22, 2024, with GPC Partners Investments (SPV III) LP.

F5 · shares: In accordance with its terms, the Option became exercisable for an additional 28,236 shares upon closing of the underwriters' over-allotment option on May 28, 2024.

F5 · derivative.underlying_shares: In accordance with its terms, the Option became exercisable for an additional 28,236 shares upon closing of the underwriters' over-allotment option on May 28, 2024.

SEC source: 0000351040-24-000009 · primary_doc.xml · derivative · entry 1

AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. · CIK 0000351040 · Director · 10% owner · See Remarks

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,670,721

Underlying: Common Stock · 56,471 shares

Expires 2034-05-23

F1 · security: Pursuant to a Warrant Agreement, dated May 23, 2024, with the Issuer.

F2 · shares: In accordance with its terms, the Warrant became exercisable for an additional 56,471 shares upon closing of the underwriters' over-allotment option on May 28, 2024.

F3 · derivative.exercise_date: This Warrant will vest as to 20% of the total number of shares subject to the Warrant on the first, second, third, fourth and fifth anniversaries of the vesting commencement date (05/23/2024).

F3 · derivative.expiration_date: This Warrant will vest as to 20% of the total number of shares subject to the Warrant on the first, second, third, fourth and fifth anniversaries of the vesting commencement date (05/23/2024).

F2 · derivative.underlying_shares: In accordance with its terms, the Warrant became exercisable for an additional 56,471 shares upon closing of the underwriters' over-allotment option on May 28, 2024.

SEC source: 0000351040-24-000008 · primary_doc.xml · derivative · entry 1

AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. · CIK 0000351040 · Director · 10% owner · See Remarks

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,614,250

Underlying: Common Stock · 1,614,250 shares

Expires 2034-05-23

F1 · security: Pursuant to a Warrant Agreement, dated May 23, 2024, with the Issuer.

F2 · shares: This assumes that the over-allotment option granted by the Issuer to the underwriters will not be exercised. To the extent it is exercised, the Warrant will be increased by a number of shares equal to 5% of such additional shares issued, up to a maximum of 1,670,721.

F3 · derivative.exercise_date: This Warrant will vest as to 20% of the total number of shares subject to the Warrant on the first, second, third, fourth and fifth anniversaries of the vesting commencement date (05/23/2024).

F3 · derivative.expiration_date: This Warrant will vest as to 20% of the total number of shares subject to the Warrant on the first, second, third, fourth and fifth anniversaries of the vesting commencement date (05/23/2024).

F2 · derivative.underlying_shares: This assumes that the over-allotment option granted by the Issuer to the underwriters will not be exercised. To the extent it is exercised, the Warrant will be increased by a number of shares equal to 5% of such additional shares issued, up to a maximum of 1,670,721.

F2 · balance_after: This assumes that the over-allotment option granted by the Issuer to the underwriters will not be exercised. To the extent it is exercised, the Warrant will be increased by a number of shares equal to 5% of such additional shares issued, up to a maximum of 1,670,721.