Journal of Olly Headey. Co-founder & CTO at FreeAgent.

👋 HEY.com vs Fastmail. A review.

July 15th, 2020

I've been a fanboy of DHH and Jason of Basecamp since around 2006 when I first read Getting Real and started writing code in Rails. We used Basecamp (and for a brief time, Highrise) as our primary communication tool for the first few years of FreeAgent and it was a big influence from a product point of view. For the past 8 years though, I've not really used Basecamp products but I have remained a follower of the company and founders, reading their books and enjoying their Twitter rants. I'm still an ardent Rails fan as well 👨‍💻 

When I heard about HEY, I was immediately interested. Not because I've lost control of my inbox (I'm an order-freak and avid filterer so my inbox is generally a tranquil place), but because the HEY statement about why "Email’s a treasure" rang so true to me and because a brand-new, Rails-based, Basecamp product is always going to be pretty exciting to try.

I got my invite early and I've been kicking the tyres for a while, so I've written up a few thoughts to get them out there and to hear about what other people think.

Locked In The House (Vol. 1)

April 15th, 2020
Once upon a time I used to buy vinyl records and play them in dark rooms full (sometimes) of people. I used to record mixes to C90 cassette (!), and eventually on CD, and I'd design covers and send them to willing listeners I met on obscure internet mailing lists in the 1990s. They were halcyon days ☀️

I flogged my decks and mixer in 2011 and haven't bought vinyl since the mid-00s (I still have all my records in the garage though, if anyone wants them?). I do miss it a bit, but life moves on.

I still love the music though and my tastes in 'dance' music haven't really changed that much. The music might be similar but the technology has moved on enormously. I can now instantly buy tracks in lossless digital format for a fraction of what I'd pay for vinyl even a decade ago, and I can mix them up with nothing more than an iPad and the Traktor DJ app which, while not quite a substitute for the tactile 1200s experience, is still remarkably satisfying. 

At the start of lockdown I bought a bag of tracks from Juno Download and threw a new mix together.



2019 was a blur

December 30th, 2019
Years now fly by. 2019 feels more of a blur than any previous year, which is probably the ageing process. Some great highs this year, but sadly some deep, dark lows. 2019 was definitely a year where I’ve felt like there’s been a lack of ‘thinking time’, but despite that I always seem to do enough to pull together an annual cultural highlight list.

How to Eat a Burrito

August 29th, 2019


I was privileged to be able to speak at the Turing Fest conference in my home town of Edinburgh today. It's a "cross-functional tech conference" covering everything from marketing, sales, engineering, startups and business growth. I've been every year for the past three (or perhaps it's four) years and it's always been excellent. It's great to see such a high quality conference in Edinburgh, it's up there with the world's best.


The calibre of talks is generally really high, so I put in what felt like an inordinate amount of time preparing the talk. Partly this was because I really didn't want to cock it up, but largely because it turns out preparing a well-rehearsed talk - even a 30 minute one – is a mightily time-consuming thing to do! I really enjoyed the whole process – even delivering the talk was fun, if slightly surreal – but my respect for the speakers has gone through the roof now that I can properly appreciate the amount of time and sheer effort they devote to putting together their presentations.

Time Well Spent

January 30th, 2019
A question that’s always worth asking yourself: is the time I’m spending doing a particular task or activity well spent? Is it adding value to you or to your business in some way? Before you start work on something, ask yourself the question. In the middle of working on something, pause and ask yourself the question. When you’ve left a meeting, reflect and ask yourself the question. Was it time well spent? If it wasn’t, try and make a change.

So long, 2018

January 1st, 2019
I always get this feeling of gritty ambition at the start of a new year. Those pre-Christmas months, from the start of autumn through to winter take their toll, and while Christmas is a special time of year, for us it's usually hectic in one way or another so not exactly conducive to relaxation. Those quiet days between Hogmanay and back to work/school are when I finally feel I have time to relax, reflect and re-energise. It's this state of mind, free of hurry and stress, that seems to result in a surge in creative ideas for me. I imagine it's the same for many people, hence all the 'year in review' lists and eager self-improvement resolutions. It feels good to set goals... when you're up for taking them on.

Still Working Backwards?

December 12th, 2018
Sometimes you come across a fantastic article that is totally relevant but seems positively jurassic in internet years. Maybe you actually read it at the time, years ago (especially if you're a quadragenarian like myself). If you did, maybe you even briefly experimented with the approach, but most likely you forgot all about it and moved on to reading the latest articles because surely they're more relevant and contain better advice?

This gem from Werner Vogels is twelve years old. It describes how Amazon approached software service development to ensure they remain "customer obsessed" (noting that the customer could be internal or external). It's as relevant now as it was in 2006 and it's a worthy reminder about why software development needs to focus on the customer, why it should always start with simplicity, and why software teams need to be brought together with a shared vision.

Leadership lessons learned

May 22nd, 2018
Suhail Doshi, founder of Mixpanel, posted a Twitter thread distilling a decade of experience into fifteen bite-sized ‘lessons learned’ since becoming a founder and CEO at age 20. It’s fantastic advice, not just for CEOs but for anyone in a leadership position having to deal with scaling a team or a company. If that describes you, at any level of experience frankly, you will be able to take something from it.

Certainly much of it compared with my own experience, especially these themes: delegate early, listen intently and learn voraciously.

Security for CTOs

December 7th, 2017
Myself and Jean-Baptiste Aviat, CTO at Sqreen, took part on a panel hosted by Rodrigo Martinez from Point Nine Capital at the marvellous SaaStock 2017 in Dublin. The recording is now available on YouTube.


The Eisenhower Matrix

August 24th, 2017
I’ve only just learned about this prioritisation system despite using it successfully for two decades. I’ve always referred to it as the The Four D's: Do It, Decide When, Delegate It, Delete It. 

Regardless of what you choose to call it, it works wonders.