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Make More Money! Jerry Bostleman | Wait What!? with Aimee Mayo #4

Shownote

Jerry Bostleman co-founded Vaco from zero, built it into a $1 billion company, made over 100 millionaires, and has invested in nearly 100 companies across industries. He also got pushed out of the company he built — and what he learned from that is the mos...

Highlights

Jerry Bostleman, co-founder of Vaco, shares raw insights from building a billion-dollar company, getting pushed out, and the lessons that followed. This conversation covers investing, delegation, and the mindset needed to succeed.
00:00
Focus on tasks only you can do.
01:30
THC beverage helps with social anxiety and hangovers
05:59
Ancestry DNA tests sell your data.
07:44
He recounts raising $500,000 in 2001 from investors despite the post-9/11 economic climate
12:08
Vaco liberates top talent from soulless bureaucracies.
18:27
Vaco's value is saving time and creating certainty of success.
26:10
No just means you asked the wrong person.
29:52
Fear of change drives city council opposition.
37:09
No hangover, better social lubricant.
41:40
Cannabis brings peace where opiates fail.
47:31
I was a joy bully and a workaholic.
1:00:18
Being a control freak is not scalable.
1:10:31
Setbacks can lead to unexpected successes
1:17:06
Most people are not intentionally rude, just busy.
1:19:47
Write a robust business plan and set a go-for plan to test viability.
1:28:50
I'm an entrepreneurial junkie.
1:35:58
She sent it directly to Kenny Chesney who cut it immediately.
1:41:00
I have a secret billion-dollar idea.
1:53:34
AI will be the last to disrupt the creative mind.
1:54:09
Thanks for watching

Chapters

Cold Open: Invest, Delegate, Survive
00:00
Seltzers And The Nightcap
01:30
Childhood Money Lessons And Adoption
03:30
First Big Raise After 9/11
07:39
What Vaco Actually Does
12:07
Hiring, Firing, And Nanny Nightmares
15:52
Yes And: Better Business Conversations
21:52
Beating Bureaucracy With The Right Person
27:37
Building Drinks In Tennessee
34:27
Daylight Savings Time Sucks
39:00
The Mistake: Ignoring Your Own Demons
45:17
Investing Criteria: Teams And Coachability
52:37
Entrepreneurship Feels Like Dragon Slaying
1:05:08
Assume Positive Intent And Forgive Faster
1:11:43
Business Plans And Escaping Micromanagement
1:19:47
Making Money By Scaling
1:28:50
Leading Manufacturing With Process And Joy
1:35:58
Secret Ideas And Favorite Investments
1:41:00
Laptop + $1,000 = MILLIONS!
1:50:30
Closing Toast
1:54:09

Transcript

Jerry Bostleman: many things you invested in, so I'm invested in, I mean, a lot, like maybe 75 or 85. Aimee Mayo: I spend a lot of my time doing shit, I'm terrible at that, I don't need to be doing. In the first place. I was asking, ChatGPT, what do I k...