Inspiration

A 17-post collection

An interview on the Misfit Founders podcast

The incredibly generous and supportive Biro Florin recently invited me on his show Misfit Founders.

The show was filmed in his beautiful house in Brighton, UK, and we chatted about building a SaaS business, and a whole lot more.

It's the first time I've spoken at length about our work on EcoSend and how GoSquared fits into a bigger picture more than ever.

It's a very long show (the best part of two hours!) so if you have the time, I hope you enjoy it.

Thank you Biro, for inviting me on, and helping to set my life goals for a podcasting setup like yours!

Designing the LoveFrom, Serif typeface

If you're into design, and especially typography, you're going to love this.

With a brief introduction from Sir Jony Ive, this talk dives deep into the design of the LoveFrom, Serif typeface.

I found it fascinating to learn how the team took inspiration from the original works of Baskerville, even finding the original hand-made steel plates that measure just a few millimetres, made hundreds of years ago.

Where do you find inspiration to write?

Every so often, I feel at a loss when trying to figure out what to write about.

I frequently feel uninspired and lacking in ideas, so I will go weeks, possibly months without writing.

But there’s a great source of material I haven’t turned to enough: questions.

Whenever I speak at an event, or meet another founder, or really, anyone, I’m usually thrown a question of some sort.

I’ve started to note these questions down, as they’re the perfect starting point for topics to write about.

I’ve found that writing answers to questions I’ve been asked has three valuable advantages:

1. Writing addresses my frustration

If I had more time, I’d have written a shorter letter. — Blaise Pascal

When I’m asked a question, typically I must think on my feet.

Occasionally, that works OK. But sometimes, about 2 minutes after I’ve answered the question, I’ll realise I had something better to say on the topic.

There’s no rewind, or “edit” button for live conversation.

It can be incredibly frustrating!

By retrospectively writing an answer to questions I’m asked, I can address my frustration by giving a better answer.

2. Writing helps form better answers

I find writing to be a fantastic way to clarify my thoughts.

It forces me to consider something on a deeper level. The act of writing can crystallise a topic for me.

It’s correlated to the way I like to learn: if I must teach someone about something, it will absolutely force me to learn more about that thing.

I’ve often found that teaching others is the best way to teach myself, but it always feels like cheating!

3. Writing multiplies my impact

I’d like to think another benefit of turning these questions into written articles shared here, is that I can be more helpful to you, the reader of this blog.

When I have a chat with a friend, or when I am fortunate enough to speak at an event, I often think “gosh I wish that was recorded, the conversation could have been very helpful for more people.”

A wonderful thing about writing is it tends to last a lot longer than audio or video. It’s easier to find via search, and can more easily be edited to bring it up to date.

Some questions I have written answers to

Some questions I need to write answers to

  • Why are you building an email marketing tool, when it’s one of the most crowded markets you could possibly enter?
  • What’s driving you after so many years to keep doing GoSquared?
  • How have your values influenced your decisions and lifestyle recently?
  • What advice do you have for someone starting out on their own startup journey?

Do you have a question for me? Please

Measurement, goals, and instinct

“Not everything that can be counted counts. Not everything that counts can be counted.” — Albert Einstein

A friend shared a fantastic podcast episode with me today: Brian Chesky of Airbnb on Steven Bartlett’s show, “Diary of a CEO.”

Brian shares his journey building Airbnb and covers many of the low points and personal challenges of being a founder, grappling with balancing work and friendships, and a lot more. I highly recommend giving the episode a listen.

Something Brian also talked about creativity, instinct, and measuring success.

He highlighted that Airbnb is one of the few companies in the Fortune 500 with a designer and creative talent in the boardroom.

The world of business has come to praise measurement and financials more than creativity. Yet, the world is changing faster than ever, requiring ever more creative thinking to adapt and change.

I’ve always struggled with balancing instinct, creative ideas, and doing bold but immeasurable work against the “proper” way to do things: small, measurable experiments, data-driven decision-making, and focusing on ROI.

It reminded me of a quote I read a while ago from David Ogilvy:

“I notice increasing reluctance on the part of marketing executives to use judgment; they are coming to rely too much on research, and they use it as a drunkard uses a lamp post for support, rather than for illumination.”

Why put craft into anything if you can’t prove it makes a difference?

Why go the extra mile to make things “just right” if no one seems to care?

Brian’s suggestion is to not try to measure it.

As soon as someone passionate about their craft has to justify making their work as good as it can possibly be, they should probably move on.

Craft and creativity must be baked into your company’s culture. As a leader, you are the one that sets and reinforces that culture in every action you take.

The whole conversation inspired me. Speak up for what you believe in a little more.

Episode 14 of Lost and Founder — The January Blues

In my first episode of Lost and Founder of 2022, I talk about how I’m getting through the darkest month of the year, and why January can actually be a great time reflect, reset, and build a stronger you for the year ahead.

I always find January a tough month — all the fun and excitement of Christmas and new years is over, the weather is awful, it’s dark outside, and to top it all off we’re still in the midst of a global pandemic.

But fear not, there’s a world of opportunity out there! I’m spending some time at the start of January to reflect on 2021. I’m not setting myself huge audacious goals because I don’t know what the future holds, and I know the chances of success are low unless I use my previous experience to inform my future actions.

Don’t get caught up in all the “new year, new you” nonsense — be careful what you read on social media! Instead, look at yourself, spend time reflecting on your own successes and where things could have gone better, and use that to channel your next steps as you enter the new year.

Actions / take aways

  • Go easy on yourself — the last two years have been hard on all of us.
  • It’s never too late to reflect — if you haven’t already, you still have time to reflect on 2021.
  • You don’t have to make new years resolutions — instead get clearer on your values.
  • If you are clear on your values, channel your thinking around small habits you can adopt day by day rather than setting huge unwieldy goals.
  • Give yourself something to look forward to at the end of January — like a trip to somewhere you like, a gift to yourself, or some other treat.

Thanks, and see you next time!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

The crippling fear of hitting “publish”

“I am always doing that which I cannot do, in order that I may learn how to do it.” — Pablo Picasso

I’ve been feeling it increasingly — I’ll put a tweet together, a short article, maybe even a visual piece of work. I’ll be feeling pretty good about it, and then the time comes to hit “publish”…

That’s when the fear creeps in. What if this is rubbish? Is this going to offend someone? Will it be misunderstood? Will people judge me for it?

It’s been enough to make me undo all my work and not hit publish on countless occasions.

I know I’m not alone on this — even the best feel it to some degree whenever they’re about to publish their work.

I keep trying to tell myself, though: don’t let it stop you.

Usually, the worst thing that happens is no one cares. Everyone looks the other way and gets on with their lives.

No one cares as much about you and your work as you do.

With that in mind, I urge you (and my future self) to overcome that fear next time by hitting publish. It’s the fastest, most effective way to learn, iterate, and improve.

Remembering Richard Rogers (1933–2021)

I woke up this morning to see the news that Richard Rogers had passed away aged 88. Richard Rogers has been one of the most influential architects of the last 100 years, and while I’ve always been aware of his work I didn’t realise quite how many of my favourite buildings were created by his practice.

Among others, Rogers is responsible for the Lloyds Building in London, the Pompidou Centre in Paris, the Millennium Dome, Terminal 5 at Heathrow Airport, and The Leadenhall Building (aka “the Cheesegrater”).

Rogers’ work has influenced my fascination with modern architecture since I was in my earliest years. I still have the fondest memories of visiting the Millennium Dome as a boy in 2000 and being awed by the scale of the place. I still recall having the sense that “this is a significant moment in the world, and I’m living through it”, and the architecture I associate with that moment is almost entirely the work of Richard Rogers.

The Rogers-designed spaces I’ve been fortunate enough to visit have me feel inspired, motivated, and ambitious, but also have made me feel closer, more connected to the people around me.

His legacy will live on for many generations to come, and I hope will continue to inspire many more.

Thank you for architecting some of my favourite landmarks of London.

Read more on Wallpaper

Photo: Interior of the Lloyds Building, 2006 by Phogel.

Building a long lasting startup – interview with Biro Florin and yours truly

Building a Long Lasting Startup

I had the pleasure of being interviewed by prolific podcaster, entrepreneur, and all-round lovely guy Biro Florin this week on the The Startup Corner.

We spoke about how GoSquared got started, why a healthy dose of naivety can be an asset, and how raising money ideally needs to start with asking yourself a big, deep question. Plus a whole lot more.

If you have a spare moment in your day I'd encourage you to check out the show – Biro is a fantastic host and presenter, and a real pro when it comes to producing a quality podcast in record time.

View the show on YouTube

Episode 12 of Lost and Founder — Steve Jobs

This week marks ten years since Steve Jobs passed away, so in this episode of Lost and Founder I share how the great man himself inspired me early on.

Anyone who knows me knows I have been a fan of the fruit company from California for a long time. In this episode, I share how I became a fan of Apple early in my life – from hanging out in the design agency my mum worked at, to being fortunate enough to get an unwanted Mac from my dad's office.

Steve Jobs influenced me in many ways – through his keynotes, his showmanship, his stories, and through the many products his company brought into the world.

In this episode I summarise three key areas where Steve Jobs had an impact on me: his showmanship, his obsession with simplicity, and his views on life.

Actions / take aways

Thanks, and see you next time!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

Episode 7 of Lost and Founder – Ask Me Anything (AMA) Special

In this special episode of the Lost and Founder podcast I share my answers to three questions I received when doing an AMA (Ask Me Anything) with the Software as a Service community on Reddit this week.

It's hard to scale down an hour long conversation, followed by an evening of written Q&A on Reddit into a 20 minute show, but I tried.

In this episode I have experimented with a different format – with three questions from the AMA, and a summary of my answers. I hope you enjoy the episode!

I share my answers to these three questions:

  • How has working with the team changed over the years?
  • How have we managed to get publicity for GoSquared over the years?
  • What advice would I give to my 20 year old self?

Actions / take aways

As I have been doing for a few weeks, I want this podcast to be increasingly valuable for listeners, so I tried to boil down the show into a few actionable takeaways:

  • As a CEO, a lot of your job is to: give direction, unblock, and communicate with your team.
  • Don't purely focus on the marketing that is measurable – take risks, experiment, be bold. Do things that are impossible to measure.
  • With your marketing – make time for responding and reacting to news-worthy events in your industry. Newsjacking is a thing!
  • Be clear with what you want from life, from your business, from your team. It will make a lot of things easier.
  • Find a coach to help you make time for yourself and clarify your thoughts. You'll be glad you did.

A few links to what I mentioned in this episode of Lost and Founder:

Thanks, and see you next time!

Finding time and making time

People often say “I don’t have time”.

  • I don’t have time to write a blog post.
  • I don’t have time to learn to draw.
  • I don't have time to play a masterpiece on the piano.
  • I don’t have time to start a business.
  • I don’t have time to cook.

We all have the time. We’re all given the same 24 hours in every day, and 7 days in every week.

It’s not the time that’s the issue.

Our circumstances, attitudes, environments, goals, and clarity – those are the things that vary.

If your goals are clear, if your environment encourages you to achieve those goals, if your circumstances can be adjusted to allow you time and space to work on your goals – then time… time is made.

  • You make time for writing a blog post – one sentence a day.
  • You make time for drawing – with an open sketchbook, and a pencil at the ready, one 5 minute drawing at a time.
  • You make time for that masterpiece by time-boxing 10 minutes at the piano each morning.
  • You make time to start that business by sharing the idea with one person tomorrow and getting their feedback.
  • You make time to cook by drawing up a meal plan tonight.

Next time you hear yourself saying “I wish I had time to do that” ask yourself how much you wish you had the time. If you want the time enough then it’s really the motivation, clarity, focus, environment, and other factors you’re lacking – the time will be made.

Is your business your identity?

I saw this tweet and it made me want to smash the “reply” button and disagree. But then I resisted – it needed more words, more thought.

As with most topics, and controversial points: it's nuanced and it depends.

Businesses grow up to inherit traits from their leaders – good and bad

From everything I can see, startups (and all companies) naturally adopt the culture and behaviours of the people running them.

Whether it’s the aggressive, winner-takes-all approach of Uber (and Travis Kalanick), the hungry, fast moving, detail obsessed approach of Stripe (and the Collison brothers), or the decisive, crazy, design-obsessive approach of Apple (and Steve) – I struggle to think of a company that isn’t an extension of the identity of the people in charge of it.

That’s not to say that the company can’t adapt or adjust to address the shortcomings of the founders. In fact, it has to to succeed. We all have flaws – and the bigger the business, the more publicly known those founder flaws are.

I find this all the time at GoSquared – as I’ve grown up, I’ve tried to increasingly make myself aware of my strengths and my weaknesses. I try to ensure we hire for people that fill the vast gaps in my own skill set, and I try to ensure I keep my mouth shut on topics where I really don’t consider myself an expert.

Your identity doesn't need to map 1:1 with your business

The reason I struggle with this tweet, is that it’s a two-way statement – it’s stating your startup = your identity. I find it much easier to agree that one’s startup is heavily influenced by the founder’s identity. I find it much harder to agree that a startup defines the founder’s identity.

GoSquared defining my own identity has honestly been its own small challenge for most of my adult life.

It's been a challenge in small ways and large – for example, my first Twitter account was not "@jamesjgill" it was "@GoSquared" – the very personification of GoSquared and myself on social media back in the day were the same thing. It was this decision to not start a personal Twitter account earlier that almost certainly caused me to miss the opportunity of being "@jamesgill" on Twitter, damnit!

It’s always hard for me to have a conversation with a friend before the question of “how’s GoSquared going?” cropping up within the first 5 minutes. Work is always a logical topic to talk about when catching up with a friend, but I find that answering this question, as a founder who has only ever worked in one place for my entire career, is a deeper question.

It’s a question of “how are you finding work?”, sure, but also “how has this career path you’ve chosen worked out so far?”, and “how is the

Silent Meetings

Since remote working became default, we've all been trying different ways of working – from those adopting Slack or Teams for the first time, to doing one-on-ones over Zoom.

There's never been a better excuse to try radical changes to team collaboration.

The weekly kickoff

Every Monday morning we start the week with a kickoff.

We have a Notion doc that everyone has access to, with a clear agenda and structure.

The person who owns each “department” of the business outlines how they're doing against their objective for the quarter, and their action plan for the week to get closer to achieving it.

We used to do these kickoffs in person in our office. And then one of the team moved to Scotland (who can blame them!), so we started do do our kickoffs with one person on a video call and the rest of us in the office.

And then 2020 hit and we were forced to all join our Scottish colleague and communicate via Zoom in these Monday morning meetings.

Lack of engagement and no lack of chaos

We started to notice a few trends in these meetings:

  • Some people would speak for more than they needed, while others would speak less.
  • We saved questions to the end and found many of the team would not have the opportunity to ask what they needed.
  • Regardless of Zoom it was often hard to digest numbers and explanations on the spot when spoken aloud.

Most of all, we started to question the very purpose of these meetings – what's the point of us all getting together at the same time on a call if we aren't going to interact? If we are just going to speak at each other?

Meetings are expensive.

“A man who dares to waste one hour of life has not discovered the value of life.” – Charles Darwin

Take an hour for the meeting (assuming it starts on time and finishes on time), plus the hour before to prepare, plus the 30 mins after to fully get back into your flow, multiplied by the number of people in the meeting.

Add all this up and you quickly realise you're taking 15+ hours of the team’s time.

Every member of the team is incredibly skilled, ambitious, and driven. One resource that is impossible to replace is their time – once it’s spent they’re not getting it back. So I try to be extremely cautious of any time we take from anyone on the team. In that time, does every member of the team feel like it was valuable to help them grow, perform better, and achieve their goals? Or do they feel like that meeting just robbed them of an hour of their life?

15 hours is a lot of collective team time, and when you also consider that everyone is being paid to be there, a lot of money being spent too.

Efficient, well run meetings not only matter morally but they make financial sense too for

Speaking on the Scaleup podcast

The Scaleup podcast is led by Charlotte, CEO of Equalture, as she chats with other founders and CEOs from all over the world about their journey of building a team and the impact that their teams have on their businesses. Milestones, failures and lessons learned.

I was honoured to speak with Charlotte earlier in July, and we had a fun discussion about some of the highs and lows of running GoSquared, about mistakes we've made along the way, and we dug into the back story of starting GoSquared in the first place.

Be sure to check out the full series for many other honest and open discussions with founders.

Thanks to Charlotte for inviting me on the show!

I ran the marathon

Today is Sunday 26th April – the date of the 2020 London Marathon. Except it's not happening today.

Last year, I ran the marathon – for the first time, and it was one of the best days of my life.

Before the memories of the day blur too much, I wanted to write them down. Perhaps someone else is thinking about taking part on this incredible day once the world returns to some form of normality.

Here's my story.

The build up

“Good luck! I’ll be watching from the pub.”

This was the first person I saw after leaving the house – a black cab driver – on my walk to East Dulwich station. What an appropriate way to start the most London of days – by bumping into someone with the most London of professions.

It was early. It was quiet. And it wasn't raining. Not hot, but also not cold. Perfect running weather.

It was eerily quiet – was it really the right day? Was this just a dream? Can I return to bed?

I had nothing but nerves. I could barely speak from the moment I woke up.

Should I drink more water?
Should I drink less?
Have I eaten enough?
Should I eat more?
I don't feel hungry! I don't want to be sick!
Will my top rub?
Will my knee hold out?
What if I trip?
Are my trainers going to be OK?
What if my timing chip doesn't work and my times don't get counted?
What if my bib number falls off?
Did I actually register everything OK?
What if I injure myself and have to pull out – my whole family are following me from the app?
Am I going to get there too early? Too late?

Once I reached the station – the platform was quiet, but a handful of other runners turned up. Clearly they've done this before. This is the correct day! This is the correct time.

When I arrived at London Bridge Station, the atmosphere became real – it was busy, despite being so early on a Sunday. People were shuffling around, following coloured flags to different platforms.

When I reached the top of the escalator up to the platform for the train to Maze Hill there were plenty of police around and lots of runners. The helicopter in the sky set me off – this is real. This is the London Marathon – and I am taking part in it.

Police were everywhere – looking after the runners, helping guide everyone to the right place. An immediate wave of positivity, of excitement, but also of collective nervousness diffused through the air.

London Bridge is where you must say goodbye to anyone you've been travelling with up until this point. You're on your own from here. I had to disconnect from the warm reassurance of Lauren. What I'd do to go and sit in a cafe and have a bacon roll right now...

The train journey vanished past, and before I knew it, we were at Maze Hill station.

The

NetNewsWire – Just the news you want, and nothing you don’t

NetNewWire icon
There’s never been a better time to get back into RSS. – John Gruber

I recently started using NetNewsWire on both my Mac and my iPhone to consume news via RSS feeds.

I made the change just before everything kicked off and the world got turned upside down, but it’s proved to be good timing.

I had previously been using Apple News to both keep up to date with the wider world, as well as follow specific sites.

But right now I can’t take it – the sensationalist headlines, the click bait, the fear mongering. I don’t need more of that in my life.

RSS isn’t a new technology, but it’s making yet another resurgence, and for me it’s because of one app – NetNewsWire.

NetNewsWire – the beautifully simple RSS reader for iOS and Mac

NetNewsWire for macOS
NetNewsWire shows you articles from your favourite blogs and news sites — and keeps track of what you’ve read.

It’s like podcasts, but for reading.

If you’ve been going from page to page in your browser looking for new articles to read, let NetNewsWire bring them to you instead.

NetNewsWire is free for both platforms, and it’s open source. Don’t be fooled by the term “open source” – it can often be misconstrued as synonymous for “designed by developers and decided by committee”, but that couldn't be further from the truth here.

NetNewsWire is an unbelievably great piece of software – opinionated , fast, light, accessible, and beautiful, and it’s unapologetically native. [1]

It’s apps like NetNewsWire that make me want to learn to code – to think that one day I could build something as great as this.

If you’re looking for some serenity in your news reading habits, and you’ve got an iPhone or a Mac, I implore you to go check it out.

Learn more about NetNewsWire

  1. Opinionated software tends to trump "please everyone" software – especially when you agree with the opinions of the decision maker. Brent Simmons, the creator of NetNewsWire has a fantastic blog where he shares his thought processes for many decisions he makes in bringing this wonderful app to life. ↩︎

General Magic

A few weeks ago I was fortunate to see one of the first screenings of General Magic in London.

Since seeing the movie, I've been telling everyone I meet about it.

It’s a story of one of the greatest teams of product, engineering, marketing, and leadership people coming together to build a device eerily similar to the iPhone, but in the early 90s.

Sketches of the original Genral Magic device

The movie pieces together with original footage how this incredible team came together, worked their socks off, and ultimately failed to deliver what they set out to achieve. It’s a story that makes you question the definition of failure – a ridiculous number of people from General Magic went on to practically define the world we live in now, and the ideas behind the device were spot on – they just took longer to get here than orignally thought.

Just a few of the people who were involved with General Magic:

  • Tony Fadell – joined General Magic as an intern, co-inventor of iPod and iPhone, founder of Nest.
  • Marc Porat – the CEO of General Magic, and visionary of the original device.
  • Megan Smith – became CTO of US, and VP at Google.
  • Andy Hertzfeld – member of original Macintosh team, also co-created Google Circles.
  • Joanna Hoffman – another member of original Macintosh team.
  • John Sculley – former Apple CEO, also launched the Newton to compete with Genral Magic.
  • Kevin Lynch – former CTO of Adobe, creator of Dreamweaver, VP of technology at Apple.

Huge thanks to Emma Sinclair for arranging a screening of this movie, and to Sarah Kerruish and Steve Jarrett for the fascinating Q&A after the movie.

If you're interested in the history of computing, you want to see a wealth of on-the-ground footage from one of the most influencial teams of people in technology, or you just want to be inspired by the willpower and hard work of an incredibly smart group of people, you have to watch this movie.

Learn more about General Magic the movie