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:
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.
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& #39;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& #39;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& #39;ve recalibrated by spending more time with him.

The best outcome early in the journey isn& #39;t money. It& #39;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
6/ Do the work. There& #39;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.
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& #39;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.
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
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& #39;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 https://abs.twimg.com/emoji/v2/... draggable="false" alt="🚀" title="Rakete" aria-label="Emoji: Rakete">

@LedaHealthCo - @martyrdison
@getmatterapp - @benspringwater
@flockjay - @shaanh
@Career_Karma - @rubenharris
Laskie - @ChrisJBakke
@italic - @jjeremycai
@buildatmos - @PrimalNick
@getmati - @getFilip

+ many more!
You can follow @RomeenSheth.
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