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0/ I quadrupled down on angel investing this past year and have invested $1M in 20 companies.
In the process, I’ve learned what feels like 5 years worth of lessons.
Here are my 10 biggest takeaways for anybody interested in angel investing:
In the process, I’ve learned what feels like 5 years worth of lessons.
Here are my 10 biggest takeaways for anybody interested in angel investing:
1/ Ownership reality > ownership mindset.
The earlier you think of yourself as an investor, the better.
Investing in startups is a cheat code to participating in the future with asymmetric upside.
Worst case, you lose 1x your money; best case you 1000x it.
The earlier you think of yourself as an investor, the better.
Investing in startups is a cheat code to participating in the future with asymmetric upside.
Worst case, you lose 1x your money; best case you 1000x it.
2/ Investing breaks down into 3 phases:
I. ACCESS: Did I see the company?
II. JUDGEMENT: Did I say yes?
II. VALUE: Did they say yes?
You need to be good at all 3 to get a deal done.
Figure out where you're weak / strong. Each requires a slightly different skill set.
I. ACCESS: Did I see the company?
II. JUDGEMENT: Did I say yes?
II. VALUE: Did they say yes?
You need to be good at all 3 to get a deal done.
Figure out where you're weak / strong. Each requires a slightly different skill set.
3/ Invest in founders that are better than you
When you’re floored by a founder, work with them. Period.
If you're with the right people you’ll either:
(a) make a killing because they’ll figure it out / see something you don’t or (b) learn and develop a killer network.
When you’re floored by a founder, work with them. Period.
If you're with the right people you’ll either:
(a) make a killing because they’ll figure it out / see something you don’t or (b) learn and develop a killer network.
4/ Surround yourself with people that are world class
@arjunsethi has been an amazing friend throughout my angel investing journey.
I've recalibrated by spending more time with him.
The best outcome early in the journey isn't money. It's developing a repeatable system.
@arjunsethi has been an amazing friend throughout my angel investing journey.
I've recalibrated by spending more time with him.
The best outcome early in the journey isn't money. It's developing a repeatable system.
5/ You can diligence yourself out of every deal
It takes a lot for a startup to succeed.
If you just focus on “what can go wrong”, you will say no 100% of the time.
Instead ask yourself, “if this goes right, how big can it be.”
Flipping the framing is an underrated unlock
It takes a lot for a startup to succeed.
If you just focus on “what can go wrong”, you will say no 100% of the time.
Instead ask yourself, “if this goes right, how big can it be.”
Flipping the framing is an underrated unlock
6/ Do the work. There's no substitute for reps.
Get the deck and research the space in advance.
You get better at pattern matching with time, but 0 prep work leads to bad assumptions / bias.
Implication: you will find yourself on the wrong side of a go / no go decision.
Get the deck and research the space in advance.
You get better at pattern matching with time, but 0 prep work leads to bad assumptions / bias.
Implication: you will find yourself on the wrong side of a go / no go decision.
7/ Figure out your value add.
Cliche I know.
But it makes sense when you realize, this is the only asset class where the asset ALSO picks you. It's not a 1 way street.
You need a compelling answer to: "What do you bring to the table?"
The bar for the best deals is high.
Cliche I know.
But it makes sense when you realize, this is the only asset class where the asset ALSO picks you. It's not a 1 way street.
You need a compelling answer to: "What do you bring to the table?"
The bar for the best deals is high.
8/ Analysis paralysis is fatal.
You have to be comfortably moving quickly and dealing with imperfect information or angel investing is impossible.
There were a couple awesome deals (in retrospect) where I could have invested, but fell into analysis paralysis and missed.
You have to be comfortably moving quickly and dealing with imperfect information or angel investing is impossible.
There were a couple awesome deals (in retrospect) where I could have invested, but fell into analysis paralysis and missed.
9/ Always play the long game
I worked with @shaanh for MONTHS before getting to invest in @flockjay.
If you add value, the Founder wants you in.
The ecosystem is also really interconnected. I got into an oversubscribed deal this past year because of a reference from @shaanh
I worked with @shaanh for MONTHS before getting to invest in @flockjay.
If you add value, the Founder wants you in.
The ecosystem is also really interconnected. I got into an oversubscribed deal this past year because of a reference from @shaanh
10/ This is an incredibly exciting time for tech.
There’s a lot of noise about how there’s too much capital sloshing around.
I think there isn't enough capital moving around.
To believe the ecosystem is overcapitalized is to believe that human creativity is fully tapped.
There’s a lot of noise about how there’s too much capital sloshing around.
I think there isn't enough capital moving around.
To believe the ecosystem is overcapitalized is to believe that human creativity is fully tapped.
11/ Thanks for giving me a front row seat on the 
@LedaHealthCo - @martyrdison
@getmatterapp - @benspringwater
@flockjay - @shaanh
@Career_Karma - @rubenharris
Laskie - @ChrisJBakke
@italic - @jjeremycai
@buildatmos - @PrimalNick
@getmati - @getFilip
+ many more!
@LedaHealthCo - @martyrdison
@getmatterapp - @benspringwater
@flockjay - @shaanh
@Career_Karma - @rubenharris
Laskie - @ChrisJBakke
@italic - @jjeremycai
@buildatmos - @PrimalNick
@getmati - @getFilip
+ many more!
