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Family and personal life
1 min read
Sources:
his own videos, Form 1-A, Kevin's account (Sept 29, 2026)
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Short answer
Fast, by his account. In November 2024 he filmed what he called only his second time in a small plane, a Cirrus SR20 with an instructor in Las Vegas, with McKay along. On December 25, 2024 he posted How I Became a LICENSED Pilot in 24 Days, covering the cost and the checkride. He had a first-class medical by about November 2024. In 2025 he added instrument, multi-engine and the Phenom 300E single-pilot type rating, and flew the jet he had owned since December 2022 as pilot in command. His last flight was August 31, 2025. 1234
Nov 2024: Cirrus SR20 (with an instructor; second time in a small plane)
Dec 2024: Licensed in 24 days (private pilot certificate)
2025: Instrument, multi, Phenom 300E (per the Form 1-A)
Aug 31, 2025: Last flight (his son's 10th birthday)
Before he could fly
The Phenom 300E was delivered on December 24, 2022, and for two years professional pilots flew it while Kevin sat in the back scouting markets for the company. In the delivery video he joked that you cannot get a DUI on a plane because he does not fly.
Learning
Kevin’s account
This is only my second time ever in a small plane. The first time I ever did it I was freaking out, super nervous. 1
That was November 2024, a Cirrus SR20 with a Las Vegas instructor. Thirty-seven days later he posted the video on earning the private certificate in 24 days, with the cost and the checkride preparation. A first-class medical, the airline-pilot standard, came around the same time. 24
2025
Instrument rating, multi-engine rating, and a single-pilot type rating in the Phenom 300E, each with its own training and checkride, all in one year, per the offering circular. He then flew the jet himself, including a landing in heavy turbulence he filmed in July 2025. 3
Stopping
His last flight was August 31, 2025, a trip for his son’s tenth birthday; the jet was sold October 31, 2025. His reasoning is on the does-he-still-fly page: the skill fades without constant practice, so he stopped flying, and the company travels commercially. 4
From a nervous first hour in a Cirrus to a jet type rating in about a year. Then he stopped, because a pilot who is not current is not safe. 123
Simply put
✅ The timeline
➡️ November 2024: second time ever in a small plane.
➡️ December 2024: private pilot license, 24 days of training.
➡️ 2025: instrument, multi-engine, and the Phenom 300E jet rating.
➡️ August 31, 2025: last flight.
✅ The oddity
➡️ He owned the jet for two years before he could fly it himself. Professional pilots flew it.
Sources
Kevin on YouTube, "Meet Kevin's First Flight | Pilot Debrief - Cirrus SR-20 Parachute Plane" (2024-11-18), at 0:00: “this is only my second time ever in a small plane, the first time I ever did it I was freaking out, super nervous” Watch from 0:00
Kevin on YouTube, "How I Became a LICENSED Pilot in 24 Days (How much it Cost to be a Pilot & PPL Checkride Prep]" (2024-12-25), at 0:00: “How I Became a LICENSED Pilot in 24 Days (How much it Cost to be a Pilot & PPL Checkride Prep]” Watch from 0:00
Form 1-A, Directors, Executive Officers and Significant Employees (private pilot 2024; instrument, multi-engine and Phenom 300e single-pilot type-rated 2025) Open the filing
Kevin's account (Sept 29, 2026), Question 98, flying: “Kevin received a first-class medical certificate in approximately November 2024. Kevin took his last flight on August 31, 2025.” Read the excerpt
