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Lost and Founder
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Lost and Founder

Author: James Gill

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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. James Gill started GoSquared with two friends from school in 2006, and in this podcast he shares his struggles, excitement, and everything in between with refreshing honesty.
15 Episodes
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 readingTimeline 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 Jakarta by BonsayePodcast hosting: Transistor
14. The January Blues

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 awaysGo 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 Jakarta by BonsayePodcast 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 awaysEvery 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 readingThe Great Resignation on Google Trends resignationWhat is driving the Great Resignation?, and see you next time!P.S. I'm on Twitter Jakarta by BonsayePodcast hosting: Transistor
12. Steve Jobs

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 awaysSteve Jobs commencement speech: Simple: The Obsession That Drives Apple's Success, by Ken Segall:, and see you next time!P.S. I'm on Twitter Jakarta by BonsayePodcast 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 Jakarta by BonsayePodcast hosting: Transistor
10. Time Management

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: Superhuman (email client I use): Mailman (tool to batch up your emails before they hit your inbox): Remote meetings (an article I wrote on some tips for better remote meetings): Lifeline Pomodoro Timer for Mac: Good piece on how one CEO spends their time: New "Focus Mode" coming to iOS soon: Thanks, and see you next time!P.S. I'm on Twitter Jakarta by BonsayePodcast 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.FocusIt'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 learnWriting 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.HabitsSkipping – 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 awaysFocus 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 readingAtomic habits by James Clear: tracker journal: (signup here to get $10 off and tell them I sent you: for writing goals: one CEO spends their time, and see you next time!P.S. I'm on Twitter Jakarta by BonsayePodcast 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 awaysSet a deadlineAssign an owner if you're in a teamBe clear on your prioritiesIf in doubt, optimise for speedLinks and further readingLaunching is like inviting your friends over: Forms by GoSquared:, and see you next time!P.S. I'm on Twitter Jakarta by Bonsaye, provided by
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 awaysAs 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 readingCh Daniel on Twitter: Ink – Ch Daniel's product: https://simple.inkReddit AMA with yours truly: of GoSquared history:, and see you next time!P.S. I'm on Twitter Jakarta by Bonsaye, provided by
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 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 I'm doing – if you try it out, be sure to let me know!Actions / take awaysSet 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.Links and further readingAtomic habits by James Clear: you fail to plan, you are planning to fail:, and see you next time!P.S. I'm on Twitter Jakarta by Bonsaye, provided by
In episode five I chose to focus on one topic that's been on my mind: spending my time in the best way possible as a founder, and as the CEO.I'm sure many of the others founders listening along also started out as makers – either as programmers, designers, or perhaps another creative field.But as you've grown your business and added people to your team, perhaps you've struggled with what I frequently come up against: prioritising time between actioning work "in" the business and working "on" the business.In this episode I share a few of the ways I'm trying to keep myself on track.Key highlights / actions this week:To be a better version of yourself, try to visualise that person and ask what they would do next time you're in a tricky situation.Box your time – either by hour or by day, to give you time for the important and the urgent tasks.Don't be too harsh on yourself or your team-mates: everyone in the world is tired and exhausted after over a year of the global pandemic. It's OK to not be your 100% self right now.Thanks again to everyone who is tuning in – if you have any thoughts on this episode, let me know!Links and further reading:Paul Graham's Maker vs manager essay: post I wrote a while back on time boxing:, and see you next time!P.S. I'm on Twitter Jakarta by Bonsaye, provided by
LOTS of people reaching out after episode three either going through similar struggles or know people who are. YOU ARE NOT ALONE!In episode four I surface a few of the many things on my mind since last week – whether it's OK to be unclear on the vision of your business, why startups are so hard, how to balance realism vs optimism, and how to be more helpful with your team.Key highlights / actions this week:Vision is good, but a business is better (in my opinion) – ideally you want both!Maintain a healthy optimism when building a business – start with yes to avoid shutting ideas down too early.Don’t ask “How can I help?” – try to be more helpful than that by offering suggestions.Links and further readingLink to the tweet thread I mention in this episode: "How can I help?" blog post I wrote on starting with yes: out to Liam for putting this diagram together to visualise some of the thinking in episode three: again to everyone who is tuning in – if you have any thoughts on this episode, let me know!Thanks for listening, and see you next time!Music: Jakarta by Bonsaye, provided by
Episode 3 is here and I am so grateful to everyone who's been tuning in so far. I've been hearing many lovely stories, and helpful feedback to make this podcast better. Thank you.This week, it's been a tough week. I started this podcast as a way to speak some of my thoughts out loud, and I said I'd be as open and transparent as I possibly can be. This week you'll see that I wasn't lying.This episode runs a little longer than previous episodes, but the thoughts were flowing and I kept recording. Hope you can forgive me.Here's what I cover:* How I find positives from my anxiety and stress.* How I overcome feeling physically sick with worry.* The importance of exercise, habits, and a healthy routine.* How transparent should you be with your team?* Why making the wrong decision today can be better than no decision at all.* The importance of having clear goals and a timeline to achieve them.It's a packed episode. It's full of rambling. But it's honest to its core. I hope you find value in the show, and I look forward to sharing more updates as we move together on this journey.Thanks, and see you next time.Music: Jakarta by Bonsaye, provided by
Thank you so much to everyone who tuned in for episode 1 last week!This week I wanted to follow on from some of the topics we touched on last week – particularly around starting a new quarter, and the need to define strategy without a crystal ball to see what works.I also touch on when to use data vs your gut and why sometimes gut is under-rated (and how it's not something many want to admit to using these days).As a second part of today's episode, I talk about forming habits – why I bought a skipping rope at the weekend, and how you can grow as an individual and as a company by building small, healthy habits.Why this all belongs together in one show? It's all on my mind – and Good Strategy + Healthy Habits I think can lead to great success.I truly hope you enjoy episode two, and please let me know on Twitter if you want to hear about another topic next time!Music: Jakarta by Bonsaye, provided by
In the first (and hopefully not only) episode of Lost and Founder, hear how a new quarter is causing some anxiety for me, and what to do when everyone looks to you for answers.This episode, because we're talking about a new quarter, naturally goes into discussion about OKRs and how to set goals for the team. We can go deeper on all these topics in the future, but the primary goal of this episode was to share what's on my mind right now and get a show out there.I hope you enjoy the show, the format, and the idea – and if you have suggestions, questions, or feedback, let me know on Twitter!Music: Jakarta by Bonsaye, provided by