The Education of a Startup Investor

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#CapitalAtRisk

Matthew Stafford
Jul 31, 2022
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Above: Start something that matters by Blake Mycoskie

History doesn't repeat itself, but it often rhymes

The ‘Great Recession’ officially began in December 2007 and ended in June 2009, which made it the longest recession since World War II

1
.

That didn’t stop some people:

  • Airbnb, August 2008. “brian, i thought of a way to make a few bucks…”

    2
    .

  • Dropbox, September 2008. “I'd rather see the idea through, but I'd probably have a hard time turning down $1m”

    3
    .

  • Bitcoin, October 2008. “What is needed is an electronic payment system based on cryptographic proof instead of trust, allowing any two willing parties to transact directly with each other without the need for a trusted third party”

    4
    .

  • Groupon, November 2008. Groupon came from Andrew Mason’s frustration trying to cancel a mobile phone contract in 2006

    5
    .

  • WhatsApp, February 2009. Initially, WhatsApp was not intended to be a messaging app

    6
    .

  • Uber, March 2009. After spending $800 hiring a private driver, Garrett Camp wanted to find a way to reduce the cost

    7
    .

What should you do?

It’s going to get rough, but I think the tough times make us think harder about what matters in the long-term. When things are difficult they can actually become much more manageable.

To the founders and the investors among you: Work hard and smart, be patient, and most of all, keep going.

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Important: None of these posts are investment advice. If you are thinking about investing you should seek the advice of a suitably qualified independent advisor.

#CapitalAtRisk

1

Federal Reserve History, here.

2

From an email from Joe Gebbia to Brian Chesky, here.

3

From Drew Houston’s Y Combinator application form, here.

4

From Bitcoin: A Peer-to-Peer Electronic Cash System, here.

5

From Wikipedia, here.

6

From Wikipedia, here.

7

Business Insider, here.

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