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Serendipity Hacks

Above: Atomic Habits by James Clear

Engineering serendipity

In 2011 as part of the ‘Gateway2Investment’ programme I was working on I came up with the idea of doing some investor dinners and investor breakfasts in London. The programme was all geared towards helping startups raise equity investment and I had been inspired by something I had seen happening in Silicon Valley. It may have been Jason’s Open Angel Forum but I honestly cannot remember. I wish I could so I could give proper credit.

Anyway, throughout 2011 myself the G2I team hosted a bunch of these dinners and breakfasts. They were small groups of 15 or so people and I invited proper angel investors and VCs (people I knew were ready, willing and able to write investment cheques) and good startup founders (people I knew would pitch well and were good enough to have a chance at getting investment).

I saw putting the right people in the right room then letting them get on with it as engineering some much needed serendipity and the dinners were a huge success — follow-up meetings followed and a good number of the founders ended up getting investment. As this was an HMGovernment programme I didn’t get involved in the minutiae of the investment or take any fees, the G2I team was there to stir the pot, to set the stage and make good things happen.

And happen they did. Those dinners ended up contributing a lot to the £22m of investment that the G2I programme helped raise for 52 startups back in 2011. Great job. Sort of.

Something bothered me with those dinners and breakfasts. I was disappointed with the founders. I thought they’d missed a trick and could have done more…

But I was wrong

What bothered me was that at the end of every dinner and breakfast the founders would huddle together, away from the investors, and talk amongst themselves. At first this really annoyed me — I’d got them there to talk to the investors, not gossip with each other!

However that happened often enough with different groups of people I tried to figure out what was going on. It turned out they were talking to each other about the every-day, business-of-business challenges they were facing. These were things they couldn’t really talk to anyone else about. When with investors, clients, users and potential hires they had to be confident and everything had to be brilliant, up and to the right! Their friends who were not founders didn’t understand what they were going through and their partner at home was probably sick of hearing about it all…yet again.

Katie (who I worked with on the G2I programme) and I wanted to do something about it. We wanted to help those founders. We wanted to create a serendipitous environment where they could talk freely about the challenges they faced, and a place where they could give and get help. As we had just run a bunch of dinners we thought that would be a great place to start.

So on 8th December 2011 in a cafe near Trafalgar Square we hosted the first ‘good meal with 9others’. A deliberately small (only ever 10; oneself and nine others), loosely curated group of founders who could come together, share a challenge, and help each other out. We were again stirring the serendipity pot and we loved it.

Almost nine years later not much had changed.

Until March 2020.

Have a system

The elephant in the room right now is of course Covid-19. We all want to connect with good people and often the best connections and the best ideas come from chance encounters. People typically put that down to serendipity and luck, as if there’s nothing they can do about it. However what I have seen through 9others is that serendipity can be engineered if you have the right system, even in a pandemic.

With a few months of lockdown in the spring and another looming during what will be a long winter how can serendipity and chance meetings happen when we’re stuck at home in front of a screen?

Below are three parts of my system. These are things that I have done a few times during the last few months to connect and re-connect with people so that I don’t suffer from too much cabin fever mixed with Groundhog Day. I hope that you find them useful too:

Search some random emails

  • Go back a few years, make a search query for emails from, say, a month either side of 02/05/2014 and reply to 20 interesting people. What should you say? Ask how things are going and offer to help. No one *really* wants more emails, especially long ones, so never write more than three lines — remember it’s a conversation here not an essay.

Download all your LinkedIn connections

  • Do you remember when having ‘500+’ LinkedIn connections was a thing? I was really pleased when I got there. I now have 6,294. Blimey. I like to think I’m pretty good at remembering people but can’t remember that many. So I do some scrolling and names from the past pop out, which is lovely to see and I get in touch. If you get a good conversation going then how about asking them to introduce you to five of the smartest people they’ve met recently?

Go through Twitter DMs

  • This also works for Slack messages, WhatsApp messages, SMS and the like. Get the scroll going by flicking up your thumb then wherever it settles reply to some DMs. The good thing about DMs, WhatsApp messages etc is that they’re short. You can instantly see what the conversation was about at the time and you can ask them about it. Did they solve that problem? Get that investment? Make that sale?

Then keep going

When I started hosting meals with 9others I had no idea where it would go. I certainly didn’t think hosts in 45 other cities around the world would get on board so we could host over 4,500 founders almost 9 years later. But I did know that if I did that first dinner, then another, then another….that surely something good would come from them. Now the trusted relationships I’ve started and built at 9others drive everything I do — so many good friends, a growing portfolio and my own trusted counsel.

And that’s the point really. It turns out these things aren’t the hacks or shortcuts that many people spend a lot of time looking for; they’re habits in a system.

You have to begin yours.

And then you just have to keep going.


Over the course of the next few weeks I will be sharing more posts like this. You can subscribe to the written posts for free. If you become a paid subscriber (for $50 per year) you also get access to the weekly audio interviews I do with angel investors plus you get my mobile number so you can WhatsApp me anytime to continue the above, or similar, discussions.

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