Lost and Founder

After a four year hiatus, Lost and Founder is back. On 3rd February 2026, GoSquared celebrated 20 years in business. Here are 8 lessons I have been meaning to share for over four years: on team, leadership, and focus.

Earlier this week when we celebrated 20 years of GoSquared, I thought it was the perfect excuse to resurrect the Lost and Founder podcast and share some of the lessons I never got a chance to since our last show — over four years ago.

In this episode I share a few lessons I have learned the hard way, from team building, to leadership, to focus. And a few inspiring quotes are thrown in for good measure!

On team:

  1. Never underestimate what a small group of focused, aligned, motivated people can do.

  2. Celebrate the small wins. Have fun along the way.

  3. Most meetings don’t need to happen.

  4. Knowing yourself is a superpower.

On business and leadership:

  1. Simplicity is a war.

  2. If you think you’re repeating yourself too much, repeat some more.

  3. Focus is impossibly hard, but without it you’re doomed.

  4. Just do it.

Links and further reading

• Timeline of GoSquared over 20 years
• Our update on GoSquared after 20 years in business

Thanks, and see you next time!

P.S. You can also find me at:

• ✍️ https://www.jamesgill.co
• 🍃 https://ecosend.io
• 📊 https://www.gosquared.com

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

Recently when GoSquared turned 16 years old (or young?) we shared a blog post with 16 lessons from those 16 years. We received a ton of great feedback on the post, so I thought it’d be good to share some of those lessons on the show and speak about them a little more.

Here are the first 8 of the 16 lessons we’ve learned along the way so far...

On ideas and building:

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

On customers:

1. Use your own product. Be your own customer
2. Charge the trust battery
3. Your customers are smart — treat them accordingly
4. Treat each customer as unique, but scale your process

Links and further reading

• Timeline of GoSquared over 16 years
• The complete blog post of our 16 lessons from 16 years
• Ideas are fragile
• Trust battery

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

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!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

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

• The Great Resignation on Google Trends https://trends.google.com/trends/explore?q=great resignation
• What is driving the Great Resignation? https://hbr.org/2021/09/who-is-driving-the-great-resignation

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

Anyone who knows me knows I have been a fan of the fruit company from California for a long time.

In this episode, I talk through 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

• Steve Jobs commencement speech: https://www.youtube.com/watch?v=UF8uR6Z6KLc
• Insanely Simple: The Obsession That Drives Apple's Success, by Ken Segall: https://amzn.to/3v704lS

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

I have spoken a lot about habits and healthy routines on this podcast in previous episodes, but this week I wanted to change the focus to what happens when you fall out of touch with those routines and start to feel overwhelmed.

It's so important to give yourself time to rest and recharge – it's only by pausing you can truly reset and move forward stronger.

As the renowned street artist Banksy once said: "Learn to rest, not to quit."

Actions / take aways

• Find ways to check in with yourself to understand how you're feeling.
• If you feel you're overwhelmed or struggling, don't be afraid to pause and rest.
• Sometimes a reset is what you need – take the time you need to get back on track.
• You might not need a holiday – sometimes just a day to yourself can help.
• If you've been stuck in the same surroundings, try getting into a different environment – a coffee shop works for me.

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

"The secret to doing good research is to always be a little underemployed; you waste years by not being able to waste hours." — Amos Tversky

• Opposite of "traction" is "distraction".
• Making time to make time - weekly reflection on your previous week, be deliberate about your upcoming week.
• Tracking and awareness is the first step to acknowledging and improving.
• How I've been using a calendar instead of a todo list for a few weeks.
• Pomodoro technique – try it for the most challenging tasks!
• Meetings can be incredibly disruptive – I share a few tips on how to be more careful with meeting time management.
• Enable "Do Not Disturb" on macOS and iOS.
• Having Slack and your email inbox open throughout the day can be incredibly distracting. Try to open them at fixed times and batch up this work.

Actions / take aways

• Take time each week to reflect, and map your time. Book in 15 minutes this week.
• Try using a calendar instead of your todo list to plan your tasks.
• Keep meetings to fixed days in the week – like Mondays and Tuesdays, to free up your other days for deeper work.
• Wrap up meetings with 5 minute breaks in between to refresh and re-energise.
• Close your email and only open it at fixed times in the day.
• Enable "Do Not Disturb" on your devices.
• Don’t be afraid to pause, and make time for you. You can’t spend every waking hour being productive - you will eventually crash. But we each have different limits – so try to find what works best for you.

Links and further reading

• Nir Eyal: https://www.nirandfar.com
• Superhuman (email client I use): https://superhuman.com
• Mailman (tool to batch up your emails before they hit your inbox): https://mailman.to/james-8ntrxq
• Remote meetings (an article I wrote on some tips for better remote meetings): https://www.jamesgill.co/remote-meetings/
• Lifeline Pomodoro Timer for Mac: https://www.saent.com
• Good piece on how one CEO spends their time: https://review.firstround.com/an-exact-breakdown-of-how-one-ceo-spent-his-first-two-years-of-company-building
• New "Focus Mode" coming to iOS soon: https://www.macrumors.com/guide/ios-15-focus-mode/

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

In episode 9 I talk through a bunch of topics on my mind in the last week – finding and regaining focus as a team, how writing helps me break down complex topics, and I check in on some of the habits I've been trying to build.

Focus

• It's really hard to gain once you lose it as a business.
• Loss aversion can hold you back from making the right decisions.
• You often lose focus for very good reasons – regaining it can cause people to be short-term frustrated. Difficult transition, but the long term benefits are almost always worthwhile.
• Not everyone will be happy in the short-term, and that’s OK – as long as you take their feedback onboard, understand it and address it as best you can.
• Focus is hard!

Writing to learn

• Writing 200 words a day – Ulysses (a writing app) has helped me achieve this goal.
• Writing helps me understand topics better.
• Writing forces me to learn – if I want to teach and share with others I need to understand the subject better.

Habits

• Skipping – not done enough in the last few weeks, despite feeling great when I was doing it. My goal is now to aim to do a shorter time skipping and bake it into my routine.
• Writing – going well! Writing 200 words a day, thanks to encouragement from Ulysses.
• Blocking time in my calendar, instead of using a todo list – has changed a lot about my approach to time management.

Actions / take aways

• Focus is about saying no to really good ideas.
• Be clear on what you want, and what your priorities are – so spend time on those.
• Don’t be afraid to take time out to get clear on what is important to you.
• Challenging topic you're struggling to understand? Try to write it down. Scribble it, type it, and you’ll likely find it helps you clarify your thinking.
• Habits: try breaking down your habits into the smallest possible activity. Don’t give up!

Links and further reading

• Atomic habits by James Clear: https://jamesclear.com/atomic-habits
• Habit tracker journal: https://baronfig.com/tools/confidant/guided?edition=clear+habit+journal&journal=flagship&recurring=One+time+purchase (signup here to get $10 off and tell them I sent you: http://baronfig.refr.cc/jamesgill)
• Ulysses for writing goals: https://www.jamesgill.co/ulysses/
• How one CEO spends their time https://review.firstround.com/an-exact-breakdown-of-how-one-ceo-spent-his-first-two-years-of-company-building

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye

Podcast hosting: Transistor

Launching is a lot like inviting your friends over – it forces you to focus.

But when is it too early to launch, and how do you tell if you've waited too long? Let's dig in to find out.

Actions / take aways

• Set a deadline
• Assign an owner if you're in a team
• Be clear on your priorities
• If in doubt, optimise for speed

Links and further reading

• Launching is like inviting your friends over: https://www.jamesgill.co/invite-your-friends-over/
• Lead Forms by GoSquared: https://www.gosquared.com/lead-forms/

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye, provided by https://www.epidemicsound.com/referral/yjub4r

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 tonight I tried.

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

In this episode I share my answers to:

• 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 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.

Links and further reading

• Ch Daniel on Twitter: https://twitter.com/chddaniel
• Simple Ink – Ch Daniel's product: https://simple.ink
• Reddit AMA with yours truly: https://www.reddit.com/r/SaaS/comments/p31kiy/ive_spent_half_my_life_15_years_building/
• Timeline of GoSquared history: https://www.gosquared.com/about/timeline/
• Newsjacking: https://amzn.to/3AzNeht

Thanks, and see you next time!

P.S. I'm on Twitter https://twitter.com/jamesjgill

Music: Jakarta by Bonsaye, provided by https://www.epidemicsound.com/referral/yjub4r