Podcast

A 17-post collection

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!

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.

Episode 15 of Lost and Founder — What we've learned from 16 years of GoSquared

On 3rd February GoSquared turned the grand age of sixteen.

In the latest episode of Lost and Founder, I talk about eight of the 16 lessons from those 16 years — on building, ideas, and on customer relationships.

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

Thanks, and see you next time!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

Episode 14 of Lost and Founder — The January Blues

In my first episode of Lost and Founder 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.

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!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

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 12 of Lost and Founder — Steve Jobs

This week marks ten years since Steve Jobs passed away, so in this episode of Lost and Founder I share how the great man himself inspired me early on.

Anyone who knows me knows I have been a fan of the fruit company from California for a long time. In this episode, I share 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

Thanks, and see you next time!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

Episode 11 of Lost and Founder — What to do when Everything Breaks

After a brief hiatus, I'm back for the eleventh episode of Lost and Founder.

This week I share why it's so important to take a break, to rest, and recharge your batteries.

I’ve spoken a lot about habits and healthy routines on the 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.
  • Every so often 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!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

Episode 10 of Lost and Founder — Time Management

We've reached the considerable milestone of episode 10 of Lost and Founder — thank you, dear listener!

In this episode, I talk through what I have learned about time management — from how I’ve been using my calendar instead of a to-do list, to the importance of making time for reflection each week.

I hope you enjoy the show — even if I say so myself, I felt like this was a good one.

“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

Actions and 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 to-do 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.
  • We each have different limits — so try to find what works best for you.

Thanks, and see you next time!

Music: Jakarta by Bonsaye. Podcast hosting: Transistor.

Episode 9 of Lost and Founder — Finding Focus, Writing, and Habits

In episode 9 of the Lost and Founder podcast, 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.

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 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

  • How Ulysses (a writing app) has helped me achieve my goal of writing 200 words a day.
  • 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 to-do 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.
  • Try breaking down your habits into the smallest possible activity. Don’t give up.

Thanks, and see you next time!

Music: Jakarta by Bonsaye Podcast hosting: Transistor

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!

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!

Introducing the Lost and Founder Podcast

I co-founded GoSquared all the way back in 2006(!) with two of my best friends from school – Geoff and JT, and have been building, learning, failing, and winning in the world of software ever since.

Monday of this week was a rubbish day for me. I woke up frustrated, anxious, feeling deflated and not sure what to do. I almost felt like calling in sick. But instead I put my running kit on and got out for a run in the rain.

When I came back, I said "screw it" and hit record on my Mac, and spoke about what was on my mind.

Later in the evening, through the wonders of SaaS – tools like Transistor, Descript, and Epidemic Sound enabled me to take my ramblings and make them into a podcast in a few hours.

I didn't overthink this, and I know I can do better, but I started, and I hope I can continue.

Here's the show: Lost and Founder podcast

This whole thing is a bit scary – I haven't been this open or put myself personally out there much like this before. I hope you’ll like the show and join me as the journey continues.

Speaking on the Scaleup podcast

The Scaleup podcast is led by Charlotte, CEO of Equalture, as she chats with other founders and CEOs from all over the world about their journey of building a team and the impact that their teams have on their businesses. Milestones, failures and lessons learned.

I was honoured to speak with Charlotte earlier in July, and we had a fun discussion about some of the highs and lows of running GoSquared, about mistakes we've made along the way, and we dug into the back story of starting GoSquared in the first place.

Be sure to check out the full series for many other honest and open discussions with founders.

Thanks to Charlotte for inviting me on the show!