Business

A 42-post collection

34 lessons

I’m turning thirty four years old. I had been meaning to write a post on my birthday for at least four years, so it’s long overdue that I get my typing fingers out and commit myself to writing this.

Let me be abundantly clear: these are not lessons I have fully learnt. But they are lessons that I hope will prove as useful to you as they have to me.

What started as a ”30 lessons at 30” post has turned into “34 lessons at 34”.

Which is a wonderful tee up for lesson one…

1. Start today

The best time to plant a tree was thirty (four) years ago. The second best time to plant a tree is now.* Get started and stop thinking you're too late.

2. Get a coach

Find someone who can support you, listen to you, never judge you, and help you be the best version of yourself. I have worked with a coach on and off for the last four years. In that time I have become clearer than ever about what I want from life, I have co-founded a new endeavour, proposed to my partner, become fitter and healthier than ever before, and I feel more comfortable than ever in my own skin. For me, coaching has given me the space I didn't realise I needed to explore and articulate my thoughts. You can solve so many of your challenges if you give yourself the space and ask the right questions.

3. Wake up earlier

Wake up early — you can be a morning person if you fix your evenings. I believe I am naturally a night owl, but I love an early morning when I can do it. Earlier dinner, earlier bed-time, reducing screen time, and a consistent routine seem to be the path to earlier mornings for me.

4. You can run a marathon

You can run a marathon, but you need to put some trainers on first. Master putting your kit on and the rest will get easier. I still don't really think of myself as "a runner", but I find immense satisfaction from running.

5. Write a diary

It’s therapeutic and develops like a second brain. I can look back on any day in the last year and recall the tiniest details I noted down. Magic. Much like coaching, it enables me to clarify my thoughts and spot patterns in how I approach situations.

6. Take a break

Take a break – don’t quit. One day may be all you need to check in with yourself and get yourself back on track.

7. Overnight success is easy

Overnight success is easy once you’ve spent years (or decades) practicing, building, failing, and learning.

8. Build habits

Build habits a day at a time. This applies to both good and bad habits. Acknowledge what triggers both, and try to avoid living on autopilot with all of them. Small changes can compound

It just works

There’s a saying, much popularised by Apple, that distinguishes certain products:

"It just works."

It seems like a very low bar on the surface, doesn’t it?

Surely every product works, to some extent.

“It just works” only becomes a selling point when you consider how much hassle most products are to use.

Remember the last time you bought anything significant — was it entirely effortless? Was it a pleasure? Was it obvious at every step what you needed to do to start getting value from it?

I think this concept applies to services and experiences as well as products. I've written before about the experience of using my gym for the first time. And there are plenty of restaurants and hotels I've been to that fall short of the mark when judging them by the "it just works" assessment.

I don’t believe these are exhaustive, but here are a few principles that come to mind for building a product or service that just works:

  1. “It just works” means a lack of cruft and complexity.
  2. "It just works" means the product is reliable and consistently so over its lifetime.
  3. “It just works” means the maker has an opinion.
  4. “It just works” cuts to the chase, and gets the user to their desired outcome as quickly as possible.
  5. “It just works” eschews end-user choice for simplicity and obviousness.
  6. “It just works” means prioritising the primary function of the product above all else, even if that is at the expense of other meaningful uses.

These are easy to write, but very hard to achieve in a team building a real product.

It begs the question, then, why do so many products and services not “just work”?

I believe most products on the market exhibit some combination of the following:

  • A lack of care. The designers and makers just don’t care enough about the end user.
  • There is a misunderstanding of the core purpose of the product.
  • Feature creep. In a drive to make the product more attractive to more people, extra features are added in.
  • Short-term financial incentives drive cost-cutting and profit over product quality.

There are too many products that fall short of the "it just works" goal. Fortunately, that leaves tremendous opportunity for makers willing to go the extra mile.

A few products I’ve used recently that just work:

  • Granola — we’ve all been on a Zoom call that has had some form of AI note taker unexpectedly join. We’ve all experienced how useless a transcription can be. And we’ve all tried taking notes from a meeting only to find we either weren’t paying attention or missed a critical piece of information. Granola is the first note taker I’ve found that truly “just works”. You install it on your Mac, there are no awkward bots, and the results I've seen have been exactly what I wanted. It just works!
  • The Journal app — one of Apple's more recent new apps. I've

Two Clothes Hooks

It has flown by, but one of my highlights in January was attending the Better Business Summit in Manchester.

Inspired by the Better Business Summit

It’s an annual gathering of inspiring people running businesses small and large, all finding ways to do business in a better way. There were conversations on all the topics you might imagine — paying staff fairly, making products with sustainability in mind, and questioning what each of us can do to both sell and shop more thoughtfully.

Rather than relay the whole thing here, go check out the post I wrote on the EcoSend Blog about the Better Business Summit.

Patagonia, clothing, and going back in time

One of the images that has stuck in my mind since the Summit was from the impossible-to-pronounce Patagonia movie about how our habits around buying clothing have changed over the last few hundred years.

There was a time, some years after we evolved from Neanderthals, but some years before today, where we had clothes, but significantly fewer.

There was a time where each of us had just two clothes hooks.

One hook was for our everyday clothes — the ones we wore to work the land and around the house for six days of the week.

The other clothes hook was for our special clothes — the fancier of the two options that would be worn to church on a Sunday — that we kept clean and pristine.

Some years later, supposedly the French aristocracy invented something called “fashion” and it’s all gotten a bit out of hand since then.

In today’s world of fast fashion, things have changed somewhat. Even compared to 1980 (quite recent in the scheme of things), as a percentage of household spending, spend on clothing has halved, while the number of items purchased has more than doubled.

What can I do about it?

It prompted me to ask, not just for my clothes, but for all aspects of my life: do I need as much stuff?

What do I need? What do I want? And what can I give to a better home?

Last weekend I found it therapeutic to clear out over 30 items of clothing, sending them all to the local charity collection.

I now have much more space in my wardrobe. I can see more easily what I have. And I appreciate the clothes I kept.

And I still need a LOT more than just two clothes hooks.

Other things

  • I never normally catch the Super Bowl, but I always love to see the ads. Nike’s ad was my favourite this year. Incredible marketing, and a great sound track. So Win.
  • Also Super Bowl related — the Half Time Show is quite something. Here’s a look at how they put on a full-on concert in the space of about 15 minutes. I am such a geek for insider information like this!
  • The Art of Fauna is my favourite new iOS app / game — it’s a beautifully made puzzle

Reflecting on 2024

As is often the case, the Christmas period was a busy one, full of delightful moments with loved ones. I wanted to write a little about 2024 in 2024 but, predictably, I ran out of time.

We are just teetering on the edge of ”Happy New Year!” being a stale greeting, so it’s now-or-never for me to share a look back at 2024 and jot thoughts down about the year ahead.

Highlights of 2024

2024 has been a momentous year for me, with some life-defining moments I will never forget.

Engagement

I don’t think my partner would forgive me if I didn’t put this at the top of my list.

In January I took a trip to Rome and proposed. In fact, it was on this very day last year.

It felt like a dream, and was a moment I had envisioned for a long time. Somehow I managed to keep it secret, even though my partner fiancée is a rather impressive detective!

There's not a detail about the weekend I would change. It underscored my love for the person I am choosing to spend my life with, and for Italy!

Running and exercise

Accountability

Both 2023 and 2024 have been big years for my exercise regime. Early in 2023 I began working Daily Body Coach, run by a friend of mine. The experience has driven me to achieve things I never thought possible. I've transformed my attitude to fitness, to eating, to routines, and have been blown away by the results.

While DBC was not specifically about running, it clearly had an impact here. I have written about running before, and while I didn't run a marathon in 2024 it was still a personal-record-breaking year for me.

Half marathon

I took part in the Royal Parks Half marathon and completed it in my fastest time yet. I wrote a piece shortly after this about why I run.

The Hardest Mile

I also completed an event called The Hardest Mile. It's hard to describe this as anything other than ridiculous. The challenge is to get around a running track four times in an hour. Does that sound hard? No. Not until you add in the small detail of how you get around each lap:

  1. Burpees
  2. Lunges
  3. Bear crawl
  4. Run

It was brutal! Once it was over, and I made my way home on a rail replacement bus service, I reflected. When I was at school, or even just a few years ago, I would never have even contemplated doing something like this.

Parkrun

Parkrun has also been a mainstay of my weekly routine. Almost every Saturday, I get down to my local park and run 5km.

If you've never heard of Parkrun, I can't recommend it enough. It's a free, community event where you can walk, jog, or run 5km around your local park. You can volunteer or spectate as people make their way around, and they happen all around the world.

Having taken part in Parkrun

The joy of creation

Lately I have been conflicted in where I spend my time.

I love creating things. But I also love building a team, leading, marketing, and selling.

There have been patches of time where I have done very little creation, and in those periods I realise I quickly become demoralised.

I find joy in creation.

For as long as I can remember, I have been in awe of the idea that anyone can grab a computer, connect it to the internet, and build something. And that someone else on the other side of the world can then utilise and benefit from that thing.

Anyone can create something of value, and you don't need to ask anyone else for permission.

Creating vs publishing

I don't just like creating, I like publishing.

Don't get me wrong, publishing can induce immense fear.

But I get a kick out of directly creating something and then putting it live.

Getting feedback is addictive — whether it's seeing usage, receiving comments, or simply knowing "it's out there".

I sense that the act of creating is never complete, but publishing (or shipping) is a marker to say: I've completed the first step.

"Publishing" can mean anything here — deploying to production, putting a blog post live, hitting send on a Tweet or Thread, or even just writing an idea down and sharing it with your team.

The critical benefit of "publishing" is that you not only get to call your work "done" for now, you get to receive at least a little feedback: did anyone care?

Speed vs perfection

There's a study I read a while back in the book Art and Fear that summarises the dichotomy of aiming for perfection:

The ceramics teacher announced on opening day that he was dividing the class into two groups. All those on the left side of the studio, he said, would be graded solely on the quantity of work they produced, all those on the right solely on its quality.

His procedure was simple: on the final day of class he would bring in his bathroom scales and weigh the work of the “quantity” group: fifty pound of pots rated an “A”, forty pounds a “B”, and so on. Those being graded on “quality”, however, needed to produce only one pot – albeit a perfect one – to get an “A”.

Well, came grading time and a curious fact emerged: the works of highest quality were all produced by the group being graded for quantity. It seems that while the “quantity” group was busily churning out piles of work – and learning from their mistakes – the “quality” group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay.

Ever since I read this, it changed my views on perfection.

"Quick and scrappy" is often viewed as "not the proper way". The proper way is to do X and Y and Z in a specific order.

In reality,

Olympic precision, and advice from Sam Altman — weekly roundup

Last week I shared a post summarising what I had learned in the week.

I found it helpful for myself, and hopefully it may be at least mildly interesting for others too.

Here’s a few things I found interesting this week.

An incredibly densely packed set of wisdom from Sam Altman. I found this very motivating to read:

7 frameworks Sam Altman wishes someone told him earlier

I found this via Joel Hansen of Napkin Notes.

  • Getting an idea off the ground: “Optimism, obsession, self-belief, raw horsepower and personal connections are how things get started.”
  • Thinking long term: “Cohesive teams, the right combination of calmness and urgency, and unreasonable commitment are how things get finished. Long-term orientation is in short supply; try not to worry about what people think in the short term, which will get easier over time.”
  • Hiring: “Spend more time recruiting. Take risks on high-potential people with a fastrate of improvement. Look for evidence of getting stuff done in addition to intelligence.”
  • Coworkers: “Working with great people is one of the best parts of life.”
  • Making bets: “Concentrate your resources on a small number of high-conviction bets; this is easy to say but evidently hard to do. You can delete more stuff than you think.”
  • Wasting time: “Fight b*llshit and bureaucracy every time you see it and get other people to fight it too. Do not let the org chart get in the way of people working productively together.”
  • Time: “Fast iteration can make up for a lot; it's usually ok to be wrong if you iterate quickly. Plans should be measured in decades, execution should be measured in weeks.”

Other things this week

  • The first week of the Olympics in Paris has been incredible. Beautiful venues, Paris at its best.
  • I’m blown away by how little separates Olympic athletes between a gold medal and no medal. The men’s 100m final separated gold from silver by just 0.005 of a second.
  • We wrapped up July at EcoSend and it was a busy month.
  • I figured out how to add the Lost and Founder to YouTube. A while ago I started sharing my deepest darkest thoughts as a founder. I haven’t published in a while but I’m hoping to change that. I’ve just started posting old episodes to YouTube to give them a new lease of life. Stay tuned to YouTube for more.
  • I’m excited for something new for GoSquared next week. Stay tuned!

A quote for the week ahead

"The ultimate form of preparation is not planning for a specific scenario, but a mindset that can handle uncertainty." — James Clear

P.S. If you’re receiving this via email, you might notice it’s not sent from EcoSend. I’ll be changing that soon!

A few things I learned this week

A handful of things I learned in the last week:

  • Carpetright was taken (back) over by its original founder, Lord Philip Harris who grew up in Peckham near where I live. He started with a market stall in Peckham, and built it up over time to become the most successful carpet retailer in the U.K. The story of the takeover and Lord Harris’s empire is outlined in The Times. It’s also available to Apple News+ subscribers.
  • By switching to using a compostable toilet you can save 27,000 litres of fresh clean drinking water per year.
  • I was on the “Can marketing save the world?” Podcast talking about EcoSend and responsible email marketing.
  • Nestle built a supermarket on a barge to sell confectionary to communities along the Amazon river. Years on, these local communities have experienced greater rates of obesity as locals began to prefer processed foods over their native diet. I learned this while reading the truly life-changing book: Ultraprocessed.
  • The Olympic opening ceremony for the Paris 2024 games happened on Friday. Despite many dismissive reports of the ceremony, I thought it was full of incredible moments. The Eiffel Tower looked stunning, and I have no idea how they have achieved the floating balloon for the Olympic cauldron!

A quote for the week ahead

"If you want to kill any idea in the world, get a committee working on it."

— Charles Kettering (an American inventor and the holder of 186 patents)

What sells? Climate or ROI?

Climate vs ROI

What sells? 🌍 Climate, or 💰 ROI?

In the world of sustainability, what *actually* sells?

Is it a friendly, climate-focused tagline?

Or is it cold, hard business return-on-investment?

As someone who’s been leading with a sustainability focused message for over a year, just asking that question makes me feel a little uncomfortable.

When selling a product in a crowded market, you always need to stand out from the rest of the industry. And it’s hard to dislike a more sustainable alternative.

Standing out from the industry tends to mean leading with a proposition that is different. If everyone else leads with a pitch around ROI, then how do you lead with a pitch on ROI and still maintain differentiation?

I recently had an inspiring conversation with Tim Schumacher who put the question to me: do people buy based on environmental benefits or business benefits?

What gets you in the door might not be what gets you bought.

From what we’ve seen at EcoSend, leading with a pitch around climate is a fantastic way to drive awareness and attention, and it expresses our values in building the most environmentally conscious email marketing platform in the world.

However, leading with an environmental pitch doesn’t always drive business.

In fact it’s a challenge I’ve heard many times from other founders in the climate space — people love the idea of changing the world for the better, but when push comes to shove the business decision almost always wins out.

That business decision might be:

  • Switching will take time, so we’ll stick with our current tool.
  • We will go with the most trusted brand, to avoid unnecessary risk.
  • There’s a specific feature we need that your product doesn’t have.
  • We can get this cheaper elsewhere.

Fortunately with many environmental focused products and propositions the trade-off of climate vs ROI doesn’t necessarily need to exist.

Often what is better for the environment is also the more effective, more impactful decision for the business.

The challenge is finding the right balance between communicating your climate focus while driving awareness of business impact.

It’s something we’re going to experiment with more at EcoSend — by focusing on sustainability, we’re building a highly optimised, efficient platform where your emails are much more likely to get delivered, opened, read, and actioned.

Can we ultimately drive more people to a climate conscious solution by leading with a business focused pitch?

We’ll find out.

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!

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.

Thready or not, here I come

As you’ve probably seen, Meta launched their newest app today, Threads.

It’s like Twitter, only considerably slimmed down.

For day one, it seems it couldn’t have gone better for the makers of Instagram.

As someone who geeks out on tech products all the time, I find the Threads launch fascinating, so I jotted a few notes and observations down about it.

Timing is everything

It’s no coincidence that Threads is launching in the same week that sentiment towards Twitter is at an all-time low.

Elon Musk decided to enforce aggressive rate limiting for all users, made Tweeetdeck redundant for many, and obliterated the value of public URLs by preventing tweet embeds for non-logged-in users.

It’s clear Threads could be better.

It could have more features.

It’s not quite ready when you compare the feature checklist.

But launching this week while Twitter is in the dumps (more than usual) may just give it the strong gust of goodwill that helps this spark of a product turn into a full-blown, roaring fire of a platform.

Ship early, iterate

Many “critical” features aren’t in at launch, but is the app and experience solid? Is it easy for new users to onboard? Is the experience reaching a threshold that the majority of users will enjoy and trust? Yes.

You want the ability to filter your feed, you want better search, you want to have more clarity on who’s following you. You want an API. You want the app if you’re in the EU!

But all of those are trade-offs between shipping now or shipping later.

Someone had to make that call. The easy option is always to wait. Waiting always feels safer.

Shipping this week looks like it was the right call. The rest can come later.

Aside: If you’re interested, a while ago I wrote about the importance of shipping early, and often.

Nothing to lose

What I’ve enjoyed most so far as an observer of the Threads launch today has been seeing Meta operate like they have nothing to lose.

Launch today. Move fast. Share the numbers. Integrate with the open standards (eventually).

It seems unlike many of Meta’s most significant big launches: Instagram Stories was a bolt-on to not lose out to Snapchat, Reels is another tab to avoid losing out to TikTok, and Instagram itself was an acquisition.

Threads, though, is a joy to see: Zuck and the team building something that doesn’t just compete, but that could genuinely be better than Twitter. Making something people want. With a beautiful blank slate.

Maybe I am just relieved to not have another tab, view, or swipe in the Instagram app. Or perhaps it’s that my trust in Twitter has dwindled.

Whatever the reason, I’m rooting for Threads. If you’re on it, join me!

Why would Apple make a VR headset?

A quick sketch of my dream Apple headset

The silence is deafening — Apple is going to announce a VR headset imminently.

The very fact Apple hasn’t denied any rumours, and the increasing nods towards a big launch, are evidence enough. If they weren’t, then we’d know by now.

The feeling is very reminiscent of the run-up to the launch of both the original iPhone and Apple Watch — both products were widely expected to be unveiled, but the knowledge of exactly what they would entail was almost entirely unknown.

We’ve been here before

My sketches of the proposed Apple Watch ahead of its announcement.

While I never wrote about that feeling before the iPhone launch, I wrote a piece just before the Apple Watch was announced: “Why would Apple make a Watch?” in which I tried to get into the mind of the decision makers at Apple and understand why they would enter the watch market and what the device might enable.

Looking back at that piece, I feel quite proud. While I was not the only person pondering such concepts, I proposed the Apple Watch (or iWatch as I believed it’d be called at the time!) would:

  • Enable you to pay on the Subway, and allow for contactless payments — before Apple Pay came along.
  • Have easily detachable / swappable straps.
  • Become a key health companion, continuously monitoring your activity and heart rate.
  • Enable you to sleep better and wake up at the optimum time.
  • It’d prioritise telling the time at all costs, despite its smart features.

I got many things wrong too — I thought the Watch would:

  • Have incredible, unbelievable battery technology.
  • Rethink the concept of a display: “I will eat my metaphorical hat if we see a full colour backlit Retina display on the device”.
  • Be the “magic wand” remote to your Apple TV.
  • As you can see from my sketches — the physical appearance of the Watch I believed Apple would make was more akin to a Fitbit activity band.

I love reflecting on that post because it’s what makes following a secretive company like Apple so fun — you can dream and imagine, and you get to find out eventually if you were right. You get to decide if you felt Apple lived up to, exceeded, or missed your expectations.

So with an entirely new device and category just around the corner, what do we hope to see from the Californian giant?

Let’s dig in…

What will it be called?

I don’t believe Apple will call this a “headset” at all. Apple has never referred to the iPhone as a “handset” even though it’s how carriers and many consumers referred to phones before the iPhone.

Normal people don’t buy “headsets”. Headsets are for gamers and geeks.

Apple makes products for people who want the best, and they, of course, charge prices aligned with that approach.

There are numerous rumours and trademark filings, and even supposed confirmations in various code

16 lessons from 16 years of GoSquared

Today marks the 16th (yes, you read that right — sixteenth) birthday of GoSquared.

We were just kids when we started building this thing.

We were meant to be doing homework and getting into trouble, but we were obviously far too cool for that.

To celebrate this milestone, we put together a timeline of our journey from February 2006 to today.

We also took the opportunity to reflect on some of the lessons we've learnt along the way. 16 lessons to be precise. Maybe you've come across many of these before, but it never hurts to reflect...

1. Build something people want.
2. Share early, share often.
3. Constraints breed creativity — embrace them.
4. The details are not the details, they make the product.
5. Use your own product. Be your own customer.
6. Charge the trust battery.
7. Your customers are smart — treat them accordingly.
8. Treat each customer as unique, but scale your process.
9. Never underestimate what a small group of focused, aligned, motivated people can do.
10. Celebrate the small wins. Have fun along the way.
11. Most meetings don’t need to happen.
12. Knowing yourself is a superpower.
13. Simplicity is a war.
14. If you think you’re repeating yourself too much, repeat some more.
15. Focus is impossibly hard, but without it you’re doomed.
16. Just do it.

If you want to dive into any of these lessons further (and have a cup of tea in hand), then please take a look at the complete post over on the GoSquared Blog.

Finally, a huge thank you to everyone who has supported us on this journey so far. Friends, family, colleagues, customers, investors, and all the amazing people we've met along the way.

Episode 13 of Lost and Founder — The Great Resignation

It's been a fair few weeks since the last episode of Lost and Founder, but I'm pleased to return with a topic I've been doing a lot of thinking on lately: the Great Resignation.

I hope you find this episode helpful, and as always, if you want to talk about anything in the show, please reach out.

After a year and a half, it seems that more people than ever are looking for a change in their lives.

In what some have dubbed "The Great Resignation", in this episode I look at how to handle team changes in the wider context of managing a team through a period of significant change.

This year, the term "the Great Resignation" has been increasingly used to describe the explosion in people wanting to change their careers.

As a planet, we're in unprecedented times – and it's no wonder that many teams are going through a tumultuous time with changes never seen before.

If you're anything like me, handling team changes is one of the most challenging aspects of being a manager and leader. I find it hard to even know where to begin on this topic, but I thought I'd share my latest thinking in this episode with the hope it will be valuable to others out there going through similar challenges.

Actions / take aways

  • Every change is an opportunity to look at the business – what is going well, what isn't?
  • Understand people’s goals and desires and ensure they’re on the right path.
  • When someone leaves there can be tremendous opportunity for others on the team to grow into new roles.
  • Be clear with yourself on the goals and needs of the company.
  • Remember: everyone is on their own journey. You can’t control that! Focus on what you can control – organisation design, encouraging the culture and performance you want to see, leading by example, and making people the hero on their own journey.
  • You’re not alone. This stuff is hard. Talk to others and you’ll realise that many others are in the same boat and going through similar challenges.

Links and further reading

Thanks, and see you on the next show!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

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 8 of Lost and Founder — How soon should you launch?

Lead Forms by GoSquared

This week we just launched a new product at GoSquared: Lead Forms.

Launches are always exciting, and every time we do a launch we learn from it, so I decided to focus this episode of Lost and Founder on the topic of launching.

As I’ve written in the past, I feel launching is a bit like inviting your friends or relatives over to your house. Inviting someone over forces you to get your house in order — to tidy, to prepare for a deadline, and to prioritise unfinished tasks.

When launching a product or a feature, or even launching a whole new business, it’s often difficult to know when to do it. You’re pretty much always going to launch too early or too late — from my experience, it’s almost impossible to launch “perfectly on time”.

If you’re getting ready to launch something, I hope this episode is helpful for you.

Actions / take aways

I’ve outlined some key actions and take-aways for those too busy to listen to the full thing:

  • Set a deadline for your launch — every time you do this you learn how to get better at setting deadlines.
  • Assign an owner if you're in a team — if more than one person “owns” a project, then no one actually owns it.
  • Be clear on your priorities — ensure everyone is aware of what is most important to the launch and the company.
  • If in doubt, optimise for speed — moving faster tends to solve more problems than it creates. Speed means you learn faster.

Subscribe for future episodes

If you haven't already, it'd mean the world to me if you subscribe to Lost and Founder wherever you get your podcasts — find all the links to subscribe here.

Thanks and see you next time!

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!

The 2x Preparation Rule: How to turn Good Meetings into Great Meetings

A general rule of meetings I’ve found to hold true through the years: however long your proposed meeting is, you need to prepare for at least twice that amount of time in order for the meeting to run optimally.

That may sound like overkill, but I hope you can hear me out...

As with any rule, there are always exceptions. I have always found if I prepare for twice the duration time of the meeting then the outcome of the meeting itself is dramatically better. For example, if I have a 30 minute meeting to discuss a topic with three other team members, with the goal of getting to an outcome, I know that I should ideally prepare for at least an hour for it.

The seemingly excessive time I spend is recouped by saving even more from the attendees of the meeting.

This likely doesn’t need to apply for every one-on-one or regular meetings you’ve really got into a groove with, but for new meetings, and especially for meetings with 5+ people, the time one person spends preparing is often recouped several times over by being more efficient with the time of the attendees.

A while ago I wrote about how we do silent meetings – these are a great example of how the preparation beforehand is so critical, and can lead to a far better outcome for a meeting.

The expense and value of meetings

Meetings are expensive – the more people and the more time given, the more expensive they become. But they're also valuable moments where team members get to collaborate, bond, and integrate with each other.

Through lockdown and working remotely, I sense that many people enjoy a meeting to get together with their colleagues. It’s not surprising we all crave social contact and want to hear how each other is doing.

Trying to find the balance between social and “work” focus in a meeting will vary by team and culture, but it’s possible to find a sweet spot, and preparation before a meeting will help get clearer on what is needed from a meeting, and help you ascertain just how much time to spend on catching up on your weekend plans at the start of a Zoom call!

Try this out and let me know how it goes

For the next meeting you’re in charge of, book out twice the time of the meeting beforehand to prepare for it. And then assess:

  • Did the meeting run better?
  • Did you get better or clearer outcomes?
  • Did the attendees feel more energised at the end of the meeting?
  • Was the meeting shorter thanks to the preparation?
  • Did the meeting even need to happen once you did the prep?

Good luck!

Episode 6 of Lost and Founder – Planning and Habits

Another week, another episode of Lost and Founder. Really trying to keep this habit up!

Speaking of habits...

In episode six, I share my distaste for planning and how I have been reframing planning in my head to encourage me to do more of it. Setting a deadline, and making myself accountable for what I am planning has been useful for showing an outcome to my thinking and planning in the last week.

I've also been reading a helpful and practical book called Atomic Habits, by James Clear. It's all about improving your life by adopting positive, healthy habits, and trying to eliminate your bad habits.

I'm still reading it, but a rule I've already been finding helpful is the two minute rule – try adopting a new habit by breaking it down into the smallest possible task, something that can be done in just two minutes. If you can master that then you're laying the ground work for bigger things. We'll check in next week to see how we're doing – if you try it out, be sure to let me know!

Actions and take aways

  • Set a deadline, a format, and find someone to hold you accountable to your planning.
  • Try the 2 minute rule with habits – let me know what you can achieve and I’ll give a shout out next week to anyone who successfully starts adopting a new habit.

Thanks, and see you next time!

Lost and Founder episodes 3, 4, and 5

I was a little forgetful in posting about each of these episodes, so here's a batch update of my Lost and Founder podcast and a little update.

Episode 3: Anxiety vs Exercise, Bad Decisions vs No Decisions, and Goals

In episode three I talk (very) openly about how I'm working through some business challenges, discuss the value of transparency, the importance of goals, and why I benefit so much from a healthy routine.

Episode 4: Vision vs Profit, Realism vs Optimism, and How to be More Helpful

A few things on my mind in this episode: is it OK to be unclear on the vision of your business? Why are startups so hard?(!) How do you balance realism vs optimism? And how can you be more helpful with your team?

Episode 5: Working On vs In the Business

In the week before recording this episode I spent too much time "in" the business – actioning urgent tasks, contributing on design, writing, and making small, quick decisions.

Instead, I should have been spending it "on" the business. So what am I doing about it? Listen in to find out!

I hope you're enjoying the show!

Thanks to everyone who's subscribed, downloaded, listened, and given me feedback on Lost and Founder so far. I'm so thrilled to hear from listeners who are finding these stories helpful.

A key reason for starting the podcast was to help myself – to voice what was on my mind, with the hope that it would be useful to others. Having heard stories and feedback from so many people, I'm so glad I started.

Remember: no matter where you are on your journey, you are not alone!

If you haven't already, please subscribe, and tell me what you think of the show – if you have feedback, or suggestions for future topics, I want to hear from you.

Episode two of Lost and Founder – strategy, tactics, and habits

Another tough week, and episode two of my new podcast, Lost and Founder.

My goal with each episode is to be open and honest, and give a side to the founder journey that often isn’t shared enough – the unglamorous, stressful, uncertain side.

Hope you enjoy the show, and thanks to everyone who tuned in for episode one and gave me feedback and support. I owe you!

Launching is like inviting your friends over

For the last year, very few of us have had the chance to have anyone over to our homes, but I was recently casting my mind back to those happier times, and I made a connection in my mind.

I am not sure about you, but in our house, whenever we invite someone over, it’s always a deadline – a fixed point in time to get our house presentable.

I am not saying my house is a mess, but when people come over I want to present the best version of myself and my house to my guests. And when we don’t have guests, sometimes those standards can slip a little. The handful of cups on the kitchen counter. The stack of 5 letters on the kitchen table. The extra pair of shoes left out in the hall.

Having people over pushes me to tidy all these little things up – to wash the cups, to sort the letters, to hide the shoes.

In my mind, that’s exactly what launching / shipping does: you may not be ready, but you have to get your product or feature presentable – ready for others to experience it. It focuses you.

Who care where the shoes go, or whether the cups are in the dishwasher or hidden in the sink. What matters is the place looks good and feels warm and welcoming.

When shipping – who cares if the extra settings option can’t make the cut, or the secondary heading on that alert modal isn’t precisely following the style guide. What matters more than anything is you hit the launch date and ship.

Having a deadline (like knowing a friend is coming to visit) forces you to tidy, focuses you, and restricts you from tackling anything too ambitious. External judgement and validation can be a powerful motivator to prioritise.

Amazon Basics vs Peak Design

A tale of two Slings

I love this response from Peak Design.

When a huge megacorp such as Amazon blatantly rips off your work, you can respond by complaining, by writing angry tweets, by reducing your prices, by panicking, or... by putting together a hugely entertaining ad.

Always a good reminder that every day we get a chance to influence the world around us: vote with your wallet.

(Via Gruber)

15 years of GoSquared

February 3rd 2021 marked the 15th birthday of GoSquared.

It’s crazy to look back at those 15 years – it’s more than half my life!

Of course, what we’re doing now is slightly different to what we started out doing all that time ago.

We’ve learnt a lot, and I wrote about just three of my biggest lessons in a blog post on the GoSquared Blog:

  1. Build it and they will not come
  2. You make your own luck
  3. People are more difficult, and more powerful, than code

I hope you enjoy the full post: 15 years and counting running GoSquared

You might also be interested in the visual timeline of GoSquared – there’s something in there for everyone!