The Education of a Startup Investor

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10 years of 9others
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10 years of 9others

#CapitalAtRisk

Matthew Stafford
Dec 10, 2021
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10 years of 9others
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Above: The first good meal with 9others

Going from Zero to One

On 8th Dec 2011 Katie Lewis and I thought it would be a good idea to host a nice meal with a small, loosely curated, group of nine other entrepreneurs.

And for the last 10 years we've hosted a meal with 9others once a month ever since.

Hosting 4,500+ entrepreneurs at 400+ meals in 45+ cities

It's been an absolute privilege, I've certainly learned a heck of a lot and the relationships started and built through 9others drive everything I do.

Here are ten important thing I've learned:

  1. Success requires the aid of others. To be successful you will need help. And the best way to get help is to help others first — do that and you’ll be amazed at what comes back.

  2. Learn to trust your gut — if it doesn't feel right now, it's probably not.

  3. Build your network before you really need it — cold-email people you admire, tell people you like them, aim high.

  4. The long-term pay-off for being generous far outweighs any short-term pain from being cheated (which, by being generous, will inevitably happen).

  5. Make something within what you do ‘antifragile’. You’ll be more successful the more comfortable you are having uncomfortable conversations, and being vulnerable with the right people will make you stronger. Engineer this.

  6. Invite challenge — as time goes on most things drift towards the mean. Make sure to introduce randomness, keep close to those you think are exceptional and make time for catching up with the weird and wonderfully unconventional thinkers from a different walk of life.

  7. Keep things simple — if in doubt: Subtract, simplify, and don’t be a fool1.

  8. Activity does not equal achievement — your biggest impact will come from a very small number of emails, decisions and connections. Choose wisely2.

  9. Stick at it — the very best things take a long time. Be patient and trust in the process — a good deal in the short term may not be a good deal in the long term.

  10. To learn the most, ask better (simpler) questions. For example, “Yeah, but why?”3 Then be sure to keep quiet and listen.

See you in January

Thank you to everyone who's ever come along, shared a challenge and helped the 9others around the table over the last decade.

I’m hosting my next meal with 9others on Wednesday 26th January 2022 and you can sign up here.

In the long term I want 9others to solve all business challenges. That’s a tall order so I recently wondered, how will I know if it’s doing that? The answer I came up with is that 9others should outlive me. Hopefully that’ll take a while yet…

Get 9others event listings and news


In other news

Back in November 2020 Abhishek Kumar was kind enough to invite me on his ‘Steal My Marketing’ podcast, here. Since then he’s been writing the ‘Intellectual Software’ Substack, here, and each post is a short summary, or deconstruction, of how these smart people think.

Below is the latest about Michael Ovitz:

Intellectual Software
Michael Ovitz: Empire Builder
Hi Friends :) I’m back with Michael Ovitz. As I write this to you from this little town in England, I’m still amazed by what I just read. Who is Michael Ovitz is a monster read. The playbook, way ahead of its time. The accomplishments, unmatched. The stories, heartbreaking…
Read more
7 months ago · Abhishek Kumar

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

Remember, A crowd is not company, here.

2

Be more 80/20 — learn more here.

3

Talking to Founders, here.

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