How an investor who turned me down ended up sleeping on my couch

Written on 22nd September, 2012

Last week I had the great pleasure of grabbing dinner with Jon Bradford, and having him stop over at my place on his way to speak on a panel at an event in Jerusalem.

The story of how I know Jon is a crazy one, and one which whenever I think about always reminds me of the power of being on great terms with as many people as I find myself being in contact with.

Brief contact years ago

I first met Jon several years ago, when I was working on my previous startup. At that time, I’d just graduated and had jumped straight into the startup scene with a lot of passion to build something. I had no clue about what was involved in creating a startup, and ultimately the startup I worked on at that time was not successful.

I was very naive and looking back at some of the things I did and the way I wrote emails or thought about building the startup leaves me feeling grateful for how much I’ve been able to learn in the last few years. I was, however, always looking for opportunities to meet others in the startup scene (small as it was in the north of the UK), and so I created my own startup meetup and attended many others. I also tried to continually push myself out of my comfort zone, and I met Jon when I pitched the previous startup at an event in Manchester (something very uncomfortable for me at the time).

Startup accelerator rejection

At the same event I pitched my startup, Jon spoke about the startup accelerator he was creating. It was modelled on TechStars and was unique in the UK, especially in the north. Since the first accelerator around 2 years ago, Jon has gone on to help start 12 accelerators from Montreal to Moscow and runs 5: Springboard, ignite100, Startup Wise Guys, Eleven and TexDrive. I think there may well be even more on the way, too.

After hearing Jon speak about the accelerator, I spoke with my co-founder at the time Oo Nwoye and we decided it made a lot of sense to apply. We felt like we had a pretty good chance, especially since we were moving fast and had some users. A couple of weeks later, we got our rejection email and felt quite disheartened. We pushed forward regardless and ended up getting into a smaller scale incubator with a grant in Birmingham before eventually deciding that the startup wasn’t working out.

I exchanged a few emails with Jon at this time, and I remember a feeling of a lot of mutual respect. Despite the rejection, things were very amicable, and I’m happy that was the case.

No contact but a lot of progress

After that short-lived connection, the two years following were defining for myself, and evidently now with 12 accelerators he is part of, they were two short years with much progress for Jon too. For myself, I realised that the previous startup wasn’t working out (Jon made the right call) and moved on to Buffer, where applying my learnings of lean startup got the startup off to a great start. Since then, we’ve gone through AngelPad, brought great investors and advisors on board and grown Buffer to 325,000 users, an $800,000 annual revenue run rate and a team of 7.

An email to kick things off again

One of the most fascinating things about Jon is just how good he is at email. He shared with me his calculation about how much email he does, and the result was that whilst working (which is by no means any normal working hours) he sends an email every 6 minutes. Jon is someone I’m very inspired by to become much better at email. With this kind of volume, it’s no surprise that even after not being in touch for 2 years, his “touch base” email was the following, in its entirety:

Hey dude

Congratulations on AngelPad and follow-on funding - when you are next back in the UK - let me know and can catchup and grab a coffee/beer.


I know now that even the “Hey dude” was a slight exception for Jon. He gets straight to the point and this is something I’m trying to do more and more, too.

"Could I crash over?"

I’d been in touch a few times after we reconnected via email, and Jon introduced some smart people to me.

Around a month ago I got another classic Jon Bradford sized email:

What are you doing on the evening of Monday 10th? Could I crash over?


I jumped at the opportunity to get some of Jon’s time and learn from his experiences and accumulated pattern recognition. We grabbed dinner in the evening, and then headed back to the apartment where Jon made some amazing introductions for me.

This whole experience made me realise how great it is to know lots of people, even if only as acquaintances initially for a long time.

Have you had any experiences like mine of an unlikely connection becoming something very powerful? I’d love to hear your stories!

Disclaimer: I’m a mentor at ignite100 and know a few startups who’ve gone through Springboard.

Photo credit: Andrew Ferguson