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 (https://jamesgill.substack.com/s/lost-and-founder?utm_medium=podcast)
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 (https://www.gosquared.com/about/timeline/)
Our update on GoSquared after 20 years in business (https://www.gosquared.com/blog/20th-birthday)
Thanks, and see you next time!
P.S. You can also find me at:
✍️ https://www.jamesgill.co (https://www.jamesgill.co/)
🍃 https://ecosend.io (https://ecosend.io/)
📊 https://www.gosquared.com (https://www.gosquared.com/)
Music: Jakarta by Bonsaye (https://www.epidemicsound.com/referral/yjub4r)
Podcast hosting: Transistor (https://transistor.fm/?via=jamesgill)
28 Feb 2022
15. 16 years of GoSquared (Part 1)
On 3rd February 2022, GoSquared celebrated its super sweet 16th birthday. Here are 8 lessons from those 16 years — on building, ideas, and on customer relationships.
6 Jan 2022
14. The January Blues
In my first episode of 2022, I talk about how I’m getting through the darkest month of the year, and why January can actually be a great time reflect, reset, and build a stronger you for the year ahead.
20 Nov 2021
13. The Great Resignation
After a year and a half, it seems that more people than ever are looking for a change in their lives. In this episode I look at how to handle team changes in the wider context of what some have dubbed "The Great Resignation".
10 Oct 2021
12. Steve Jobs
This week marks ten years since Steve Jobs passed away, so in this episode I share how the great man himself inspired me early on.
26 Sept 2021
11. What to do when Everything Breaks
After a brief hiatus, I'm back for our eleventh episode. This week I share why it's so important to take a break, to rest, and recharge your batteries.
4 Sept 2021
10. Time Management
We've reached the huge milestone of episode 10 – thank you, dear listener! In this episode I talk through what I have learned about time management – from how I use my calendar, to the importance of making time for reflection.
26 Aug 2021
9. Finding Focus, Writing, and Habits
In episode 9 I share why it's so hard to find and regain focus in a business and how I'm working to address it. I also explain how writing helps me break down complex topics, and revisit some of the habits I've been working on over the last few weeks.
20 Aug 2021
8. How soon should you launch?
This week we just launched a new product at GoSquared: Lead Forms. Launches are always exciting but how do you know when it’s too soon (or too late) to launch?
12 Aug 2021
7. Ask Me Anything (AMA) Special
In this special episode of the 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.
4 Aug 2021
6. Planning, and Building Healthy Habits
Why do I hate planning so much? This week I share how I've reframed "planning" to help me do more of it. Plus I share what I've learnt from the latest book I've been reading: Atomic Habits.
28 Jul 2021
5. Working On vs In the Business
Last week 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?
21 Jul 2021
4. Vision vs Profit, Realism vs Optimism, and How to be More Helpful
A few things on my mind: 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 can you be more helpful with your team?
14 Jul 2021
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.
5 Jul 2021
2: Strategy, Tactics, and Building Habits
In episode two of Lost and Founder, I share my latest thinking on strategy, why strategy is different to tactics, and talk about building healthy habits both at work and home.
28 Jun 2021
1: Intro, New Quarter Anxiety, and OKRs
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.
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