Thread by @chrishlad

THE Angel Investor you definitely HAVE heard of : @Jason

1 book, 51 podcast guest appearances👇

@APompliano
@JordanHarbinger
@ShaneAParrish
@karaswisher
@HarryStebbings
@garyvee

and 1,000+ episodes on @TWiStartups

10 of his BIGGEST ideas on investing and life

🧵👇

1/ Who is @Jason? 

• Founded and sold Webblogs, @markcuban invested

• Angel investor in @Uber, @thumbtack, @RobinhoodApp,@calm

• Host of @thisweekinstartups, @allinpod

• Founder of Launch and The Syndicate

• Writer of Angel: How to Invest in Tech Startups

2/ Invest in People not Companies

“People aren’t everything, they are the only thing”

"When the right person fails, they always improve on their mistakes, but when a company fails, it can’t try again"

People > Market > Tech

3/ How to Assess a Founder

“I look in people’s eyes, and while they’re talking I can tell – and it might be from poker – if they actually believe what they’re saying”

Founder traits…
• Delusional and highly skilled
• Detail-oriented
• Actionable list to improve the biz

4/ Why Startups Fail

Reason 1: Founder quits.
• It is NOT just when founders run out of money
• Look for founders who refuse to give up

5/ Poker vs. Angel Investing

Poker teaches you about risk with skin in the game.

• Read people
• Take intelligent risks
• Only make money if you take risks on a consistent basis

Difference: angel investing has limitless upside, not just the chips at your table.

6/ Key Investing Questions

• Why has this founder chosen this business?

• How committed is this founder?

• What are this founder’s chances of succeeding in this business— and in life?

• What does winning look like in terms of revenue and my return?

7/ Pre-Product Investing

DON’T DO IT.
• Wait until the product has been in-market for at least a few weeks

WHY?
• You can talk to REAL customers and see if they LOVE the product

8/ Learning Skills

“There is NO excuse for not having the skills today.”

• You can learn 95% of desired skills on the internet

• Take open source classes from MIT, Stanford, Harvard…then get any job you want.

• Don’t watch hours of TV and complain about opportunity

9/ Work-Life Balance

• You can’t build a unicorn and have “work-life” balance

• People who struck oil think you don’t need hard work

• Effort + Skillset = Outcome

• If you love what you’re doing, work REALLY hard at it

We try to make success look easy… it ISN’T

10/ Reviving the American Dream

DEMOCRATIZE private investing

• Uber drivers investing in @Uber
• Airbnb hosts investing in @Airbnb

Fix investor accreditation rules and revive upward mobility

11/ If you liked this, check out my podcast interview with @sanderdaniels of @thumbtack.

We talk about focusing on ONE thing, how Thumbtack followed NONE of the rules of a marketplace, and Sander’s personal goal setting system.

Thumbtack is one of @Jason’s best investments!

12/ Sources

listennotes.com/podcasts/the-j…

listennotes.com/podcasts/the-p…

smashnotes.com/p/recode-decod…

13/ Sources (cont.)

fs.blog/knowledge-proj…

thetwentyminutevc.com/jasoncalacanis/

podchaser.com/creators/jason…