The Education of a Startup Investor
The Education of an Angel Investor
'Steal My Marketing' podcast
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'Steal My Marketing' podcast

I was on a podcast

Abhishek Kumar invited me onto his ‘Steal My Marketing’ podcast (thanks for the introduction Hrishi). If you listen to it you’ll hear me talking about t-shirts, YCLDN, 9others, DMG, networking, hustle and more.

2 x 10 years of lessons

My career is easily split into two decade long stints and, while there are show notes below (thanks Abhishek), I wanted to also share the top three things I thought about after listening again today, which are:

1. You only get today once

  • I knew YCLDN was such a good idea I just had to talk to people and make it happen. I didn’t care if it eventually failed. Turns out that’s what made it a success.

2. Friction is good

  • Ask tough questions and wait for the answer. Ask yourself and ask others. One of the best is, “Yeah, but why?”.

3. You recover quickly

  • To create something new, interesting and valuable you might have to destroy what went before. Not everyone will like that or see that it has to happen.


Show Notes

From Abhishek’s Twitter thread (his words, not mine):

  • Started a T-shirt company, wrote 100 letters a day.

  • Hosted the coolest Y Combinator event ever.

  • Built a global network of 4,000+ entrepreneurs.

  • Became an Angel Investor.

  • Started a t-shirt company: ultimately noticed pubs were the ones buying his t-shirts.

  • So started reaching out to a 100 pubs and restaurants a day.

  • They'd buy his t-shirts for their employees and loyal customers.

  • Later, quit that and talked himself into a software job, without a degree.

  • YCLDN: Hosted the coolest Y Combinator event ever.

  • Noticed Y Combinator was doing an event in New York - YCNYC.

  • He thought they should do one in London too.

  • Shared the idea with Katie Lewis.

  • Katie said, You should make this happen”.

  • Knew no one.

  • So he bought the domain name ycldn.com and made an image "Y NOT?" for why not in London, copied the YCNYC website and started emailing people.

  • Paul Graham replied to the Hacker News post, said it can't happen now .

  • So he gave up. Just kidding!

  • Convinced Y Combinator partner Harj Taggar to come over to London and 500 people signed up for the event in less than a week.

  • Crazy, right?

  • There are 2 more stories:

  • Built a global network of 4,000+ entrepreneurs in 46 cities.

  • Nine years back, almost to this day, Matthew had the idea of hosting a dinner just for founders.

  • Nine other founders gathered at a place in Central London to bounce around the idea.

  • That led to 9others.

  • Back in 2012 helped Ryan Graves and Sam Gellman launch Uber
    in the UK.

  • Became and Angel Investor.

  • He's invested in:

  • Talks highly of Jason and Chris. Both of them have inspired him in a lot of ways. The most important? Being kind. Be helpful. That's the greatest leverage one can have.

  • His favourite Podcast? Episode 291 of TWiST.

  • Favourite books of @mstafford:


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.

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