Lost and Founder

James Gill

Being a startup founder is not all private jets and parties. Truthfully, being a founder is a lonely, difficult, stressful, yet rewarding way to spend your life. From starting out in 2006 with friends from school, to serving some of the largest businesses in the world, this podcast shares the struggles, excitement, and everything in between with refreshing honesty. jamesgill.substack.com

  1. 16. 20 years of GoSquared

    Feb 8

    16. 20 years of GoSquared

    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 yearsOur 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    20 min
  2. 15. 16 years of GoSquared (Part 1)

    02/28/2022

    15. 16 years of GoSquared (Part 1)

    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: Build something people want.Share early, share often.Constraints breed creativity — embrace themThe details are not the details, they make the productOn customers: Use your own product. Be your own customerCharge the trust batteryYour customers are smart — treat them accordinglyTreat each customer as unique, but scale your processLinks and further reading Timeline of GoSquared over 16 yearsThe complete blog post of our 16 lessons from 16 yearsIdeas are fragileTrust batteryThanks, and see you next time! P.S. I'm on Twitter https://twitter.com/jamesjgill Music: Jakarta by Bonsaye Podcast hosting: Transistor This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    18 min
  3. 14. The January Blues

    01/06/2022

    14. The January Blues

    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 is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    15 min
  4. 13. The Great Resignation

    11/20/2021

    13. The Great Resignation

    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 resignationWhat 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    21 min
  5. 12. Steve Jobs

    10/10/2021

    12. Steve Jobs

    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=UF8uR6Z6KLcInsanely Simple: The Obsession That Drives Apple's Success, by Ken Segall: https://amzn.to/3v704lSThanks, and see you next time! P.S. I'm on Twitter https://twitter.com/jamesjgill Music: Jakarta by Bonsaye Podcast hosting: Transistor This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    24 min
  6. 11. What to do when Everything Breaks

    09/26/2021

    11. What to do when Everything Breaks

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    13 min
  7. 10. Time Management

    09/04/2021

    10. Time Management

    "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.comSuperhuman (email client I use): https://superhuman.comMailman (tool to batch up your emails before they hit your inbox): https://mailman.to/james-8ntrxqRemote 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.comGood 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-buildingNew "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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    24 min
  8. 9. Finding Focus, Writing, and Habits

    08/26/2021

    9. Finding Focus, Writing, and Habits

    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-habitsHabit 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-buildingThanks, and see you next time! P.S. I'm on Twitter https://twitter.com/jamesjgill Music: Jakarta by Bonsaye Podcast hosting: Transistor This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jamesgill.substack.com

    21 min
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About

Being a startup founder is not all private jets and parties. Truthfully, being a founder is a lonely, difficult, stressful, yet rewarding way to spend your life. From starting out in 2006 with friends from school, to serving some of the largest businesses in the world, this podcast shares the struggles, excitement, and everything in between with refreshing honesty. jamesgill.substack.com

Information

  • Creator
    James Gill
  • Years Active
    2021 - 2026
  • Episodes
    16
  • Rating
    Clean
  • Copyright
    © James Gill
  • Show Website
    Lost and Founder