McCathron Richard

SEC source: 0001567619-22-012545 · doc1.xml · nonDerivative · entry 2

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,372,204

F2 · shares: 1/16th of the RSU shares shall vest on each quarterly anniversary of May 15, 2022 over 4 years.

F4 · balance_after: Includes 2,537,686 restricted stock units.

SEC source: 0001567619-22-012545 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,910,708

F1 · shares: Commencing on May 15, 2022, the RSU shares shall vest over 4 years contingent on the satisfaction of both a 1-year service-based requirement and performance-based requirements divided into three separate tranches of performance goals based on the company's stock price, revenue, and adjusted gross profit.

F3 · balance_after: Includes 2,076,190 restricted stock units.

SEC source: 0001567619-22-011204 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,760,708

F1 · balance_after: Includes 926,190 restricted stock units.

SEC source: 0001567619-22-008588 · doc1.xml · derivative · entry 2

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,684,121

Underlying: Common Stock · 2,684,121 shares

Expires 2032-04-11

F3 · derivative.exercise_date: 1/16th of the shares underlying the option vest on each quarterly anniversary measured from February 15, 2022 for the first four quarters, and 3/16th of the shares shall vest quarterly thereafter for the remaining four quarters, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0001567619-22-008588 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,776,635

F1 · shares: The Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. 25% of the RSUs shall vest as to 1/4th on each quarterly anniversary of February 15, 2022 and 75% of the remaining RSUs shall vest as to 1/4th on each quarterly anniversary thereafter, subject to the Reporting Person's continued service to the issuer.

F2 · balance_after: Includes 989,376 restricted stock units.

SEC source: 0001567619-22-005000 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,111,135

F1 · balance_after: Includes 323,876 restricted stock units.

SEC source: 0001567619-21-021992 · doc1.xml · derivative · entry 4

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 382,666

Underlying: Common Stock · 125,000 shares

Expires 2029-05-14

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from May 13, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0001567619-21-021992 · doc1.xml · nonDerivative · entry 2

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,117,538

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 345,468 restricted stock units.

SEC source: 0001567619-21-021992 · doc1.xml · derivative · entry 3

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 86,929 shares

Expires 2027-02-28

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: This option is fully vested and exercisable.

SEC source: 0001567619-21-021992 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,992,538

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 345,468 restricted stock units.

SEC source: 0000899243-21-046180 · doc4.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,905,609

SEC source: 0001567619-21-020120 · doc1.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,878,069

F1 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. 25% of the RSUs shall vest as to 1/4th on each quarterly anniversary of November 15, 2021 and 75% of the remaining RSUs shall vest as to 1/4th on each quarterly anniversary thereafter, subject to the Reporting Person's continued service to the issuer.

F2 · balance_after: Includes 345,468 RSUs.

SEC source: 0000899243-21-039732 · doc4.xml · derivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 633,875

Underlying: Common Stock · 633,875 shares

Expires 2031-09-09

F1 · derivative.exercise_date: 1/16th of the shares underlying the option vest on each quarterly anniversary measured from September 15, 2021 for the first four quarters, and 3/16th of the shares shall vest quarterly thereafter for the remaining four quarters, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-033944 · doc4.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,532,601

SEC source: 0000899243-21-031699 · doc4.xml · derivative · entry 7

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 695,433

Underlying: Common Stock · 695,433 shares

Expires 2030-09-27

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F7 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from August 27, 2020, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-031699 · doc4.xml · derivative · entry 6

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 507,666

Underlying: Common Stock · 507,666 shares

Expires 2029-05-14

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F6 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from May 13, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-031699 · doc4.xml · derivative · entry 5

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 362,209

Underlying: Common Stock · 362,209 shares

Expires 2029-01-22

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F5 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from January 23, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-031699 · doc4.xml · derivative · entry 4

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,594

Underlying: Common Stock · 163,594 shares

Expires 2028-01-23

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F4 · derivative.exercise_date: 1/16th of the shares underlying the option vest on each quarterly anniversary measured from January 23, 2018, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-031699 · doc4.xml · derivative · entry 3

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 86,929

Underlying: Common Stock · 86,929 shares

Expires 2027-02-28

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F3 · derivative.exercise_date: This option is fully vested and exercisable.

SEC source: 0000899243-21-031699 · doc4.xml · nonDerivative · entry 2

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,508,506

F2 · kind: Shares redeemed by the Issuer at a price per share of $10 in a transaction exempt pursuant to Rule 16b-3(e).

F2 · price: Shares redeemed by the Issuer at a price per share of $10 in a transaction exempt pursuant to Rule 16b-3(e).

SEC source: 0000899243-21-031699 · doc4.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,008,506

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

SEC source: 0000899243-21-033800 · doc4a.xml · derivative · entry 7

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 695,433

Underlying: Common Stock · 695,433 shares

Expires 2030-09-27

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F8 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from August 27, 2020, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-033800 · doc4a.xml · derivative · entry 6

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 507,666

Underlying: Common Stock · 507,666 shares

Expires 2029-05-14

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F7 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from May 13, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-033800 · doc4a.xml · derivative · entry 5

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 362,209

Underlying: Common Stock · 362,209 shares

Expires 2029-01-22

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F6 · derivative.exercise_date: 1/48th of the shares underlying the option vest on each monthly anniversary measured from January 23, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-033800 · doc4a.xml · derivative · entry 4

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,593

Underlying: Common Stock · 163,593 shares

Expires 2028-01-23

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F5 · derivative.exercise_date: 1/16th of the shares underlying the option vest on each quarterly anniversary measured from January 23, 2018, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date.

SEC source: 0000899243-21-033800 · doc4a.xml · derivative · entry 3

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 86,929

Underlying: Common Stock · 86,929 shares

Expires 2027-02-28

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F4 · derivative.exercise_date: This option is fully vested and exercisable.

SEC source: 0000899243-21-033800 · doc4a.xml · nonDerivative · entry 2

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,508,501

F3 · kind: Shares redeemed by the Issuer at a price per share of $10 in a transaction exempt pursuant to Rule 16b-3(e).

F3 · price: Shares redeemed by the Issuer at a price per share of $10 in a transaction exempt pursuant to Rule 16b-3(e).

SEC source: 0000899243-21-033800 · doc4a.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,008,501

F1 · price: Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards.

F2 · balance_after: The original Form 4 filed by the Reporting Person on 8/4/2021 contained administrative errors. This Form 4/A corrects the aforementioned errors and accurately reflects the Reporting Person's ownership.