Uploaded January 2021 | Updated September 2026, 3 days ago
I'm joined by Jason DeBolt who shares the ups and downs of his TSLA investment journey on his road to being retired at 39 years old.
Jason DeBolt on Twitter: twitter.com/jasondebolt
Timestamps:
00:00 - Introduction
2:00 - Investing for outsized gains
4:25 - What led up to your first TSLA investment?
9:10 - Overview of Jason account
11:00 - Growing up in Silicon Valley
16:20 - College and compounding
19:35 - Post college at Google
27:15 - How software background impacts investments
31:00 - What triggered his first 500 pre-split purchase in 2013?
41:15 - Jason's second TSLA purchase at $82 pre-split
44:50 - Going on margin
55:55 - Getting margin called
1:01:25 - Reaction to Tesla's unravelling
1:11:20 - Paying off margin
1:15:40 - How past experience affects Jason's future investing approach
1:18:16 - TSLA exit plan
1:24:20 - Working at Tesla
1:28:00 - Google vs Amazon and Tesla
1:32:40 - Being smart in one area vs being multidisciplinary
1:38:30 - Personal conviction in the future of Tesla
1:42:50 - Ross Gerber's advise to sell some TSLA
1:48:00 - Roth IRAs
1:51:00 - Conclusion
Social
🐦 Twitter mobile.twitter.com/heydave7
🎧 Apple Podcast: podcasts.apple.com/us/podcast/dave-lee-on-investing/id1493031991
🎙️Spotify open.spotify.com/show/2iin015s0k21Bt4ldep9XT?si=uBV4Ft8hQEu_GE4YSIDDGg
📸 Instagram instagram.com/heydave7
💁🏻♂️ Disclaimer: All content on this channel is for discussion and illustrative purposes only and should not be construed as professional financial advice or recommendation to buy or sell any securities. Should you need such advice, consult a licensed financial or tax advisor. All views expressed are personal opinion as of date of recording and are subject to change without responsibility to update views. No guarantee is given regarding the accuracy of information on this channel. Neither host or guests can be held responsible for any direct or incidental loss incurred by applying any of the information offered. Author is long TSLA, LMND, SQ, and other stocks at time of original video publish date.
Buying a Tesla?
🚗 Car: Use my referral link to receive 1,000 free Supercharger miles with the purchase of a new Tesla. http://ts.la/david7556
☀️ Solar: You’ll get $100, I’ll get $500 for a new install of a Tesla solar system. http://ts.la/david7556
Videos:
Tesla ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9QkDHJ5hbv5rMvpRse9C-re
SpaceX Starlink ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9QrcuyoiO1tjQs_yzer72EI
Square ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9Q3PIw2JOQr4qoL_fSrIZA7
Lemonade ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9StEd21tlQBndopSTek8iAZ
Company Analysis Videos: youtube.com/playlist?list=PLfibpgBinf9QMjeqM7he4G7FLhI88ZXdo
Interviews: youtube.com/playlist?list=PLfibpgBinf9QdC6pEaycZvv3pGyvEbO8P
Check out my archived articles/posts on Tesla and investing: teslamotorsclub.com/tmc/threads/articles-megaposts-by-davet.23473/#post-485768
I'm joined by Jason DeBolt who shares the ups and downs of his TSLA investment journey on his road to being retired at 39 years old.
Jason DeBolt on Twitter: twitter.com/jasondebolt
Timestamps:
00:00 - Introduction
2:00 - Investing for outsized gains
4:25 - What led up to your first TSLA investment?
9:10 - Overview of Jason account
11:00 - Growing up in Silicon Valley
16:20 - College and compounding
19:35 - Post college at Google
27:15 - How software background impacts investments
31:00 - What triggered his first 500 pre-split purchase in 2013?
41:15 - Jason's second TSLA purchase at $82 pre-split
44:50 - Going on margin
55:55 - Getting margin called
1:01:25 - Reaction to Tesla's unravelling
1:11:20 - Paying off margin
1:15:40 - How past experience affects Jason's future investing approach
1:18:16 - TSLA exit plan
1:24:20 - Working at Tesla
1:28:00 - Google vs Amazon and Tesla
1:32:40 - Being smart in one area vs being multidisciplinary
1:38:30 - Personal conviction in the future of Tesla
1:42:50 - Ross Gerber's advise to sell some TSLA
1:48:00 - Roth IRAs
1:51:00 - Conclusion
Social
🐦 Twitter mobile.twitter.com/heydave7
🎧 Apple Podcast: podcasts.apple.com/us/podcast/dave-lee-on-investing/id1493031991
🎙️Spotify open.spotify.com/show/2iin015s0k21Bt4ldep9XT?si=uBV4Ft8hQEu_GE4YSIDDGg
📸 Instagram instagram.com/heydave7
💁🏻♂️ Disclaimer: All content on this channel is for discussion and illustrative purposes only and should not be construed as professional financial advice or recommendation to buy or sell any securities. Should you need such advice, consult a licensed financial or tax advisor. All views expressed are personal opinion as of date of recording and are subject to change without responsibility to update views. No guarantee is given regarding the accuracy of information on this channel. Neither host or guests can be held responsible for any direct or incidental loss incurred by applying any of the information offered. Author is long TSLA, LMND, SQ, and other stocks at time of original video publish date.
Buying a Tesla?
🚗 Car: Use my referral link to receive 1,000 free Supercharger miles with the purchase of a new Tesla. http://ts.la/david7556
☀️ Solar: You’ll get $100, I’ll get $500 for a new install of a Tesla solar system. http://ts.la/david7556
Videos:
Tesla ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9QkDHJ5hbv5rMvpRse9C-re
SpaceX Starlink ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9QrcuyoiO1tjQs_yzer72EI
Square ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9Q3PIw2JOQr4qoL_fSrIZA7
Lemonade ONLY Videos: youtube.com/playlist?list=PLfibpgBinf9StEd21tlQBndopSTek8iAZ
Company Analysis Videos: youtube.com/playlist?list=PLfibpgBinf9QMjeqM7he4G7FLhI88ZXdo
Interviews: youtube.com/playlist?list=PLfibpgBinf9QdC6pEaycZvv3pGyvEbO8P
Check out my archived articles/posts on Tesla and investing: teslamotorsclub.com/tmc/threads/articles-megaposts-by-davet.23473/#post-485768
