Steve McLeod
@steveofmcleod.com
I'm writing a book: Kill the HiPPO: How small, bootstrapped software companies decide what feature to build next.
Follow along or be a beta reader at killthehippo.com
Follow along or be a beta reader at killthehippo.com
Pinned
helpthisbook.com
A new draft chapter of my book “Kill the HiPPO: How bootstrapped software companies decide what feature to build next” is ready to read.
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
Listen to this to hear all the details of the (re-) acquisition of the Bootstrapped podcast.
107: A Ruthless Capitalist
@ianlandsman.com and @aaronfrancis.com discuss screen time for kids, the impending launch of Database School, why Ian acquired Bootstrapped.fm, and more.
@ianlandsman.com and @aaronfrancis.com discuss screen time for kids, the impending launch of Database School, why Ian acquired Bootstrapped.fm, and more.
Bootstrapped
This is the archive of Bootstrapped.fm. A seminal Bootstrapper-oriented podcast started in 2013 by Ian Landsman and Andrey Butov. The first iteration ran for 104 episodes. In 2019, Steve McLeod took over for another 139 episodes. We've set this podcast to release order so you can experience it as it was initially presented.
Bootstrapped.fm
November 18, 2025 at 3:15 PM
Listen to this to hear all the details of the (re-) acquisition of the Bootstrapped podcast.
A new draft chapter of my book “Kill the HiPPO: How bootstrapped software companies decide what feature to build next” is ready to read.
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
helpthisbook.com
November 18, 2025 at 10:19 AM
A new draft chapter of my book “Kill the HiPPO: How bootstrapped software companies decide what feature to build next” is ready to read.
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
“Until Your Company is Much Bigger, YOU are the Product Manager”
A very fitting final chapter of the book's main part.
helpthisbook.com/steve-mcleod...
For our trip to London, my daughter made a passport for Dudu, her fav stuffed toy.
November 17, 2025 at 7:26 PM
For our trip to London, my daughter made a passport for Dudu, her fav stuffed toy.
My 6-year-old daughter wanted to go ice skating at London’s Winter Wonderland yesterday.
Thing is, kids that young need to have an adult with them on the ice.
First time I had ice skated since being a teenager. Challenging for my calves - and fun until my daughter fell and pulled me down too!
Thing is, kids that young need to have an adult with them on the ice.
First time I had ice skated since being a teenager. Challenging for my calves - and fun until my daughter fell and pulled me down too!
November 17, 2025 at 8:39 AM
My 6-year-old daughter wanted to go ice skating at London’s Winter Wonderland yesterday.
Thing is, kids that young need to have an adult with them on the ice.
First time I had ice skated since being a teenager. Challenging for my calves - and fun until my daughter fell and pulled me down too!
Thing is, kids that young need to have an adult with them on the ice.
First time I had ice skated since being a teenager. Challenging for my calves - and fun until my daughter fell and pulled me down too!
I’m in London with my daughter for a couple of days.
Curious to discover that I can’t DM here in the UK on Bluesky unless I go through an age verification process.
But it seems that I can still post publicly.
Curious to discover that I can’t DM here in the UK on Bluesky unless I go through an age verification process.
But it seems that I can still post publicly.
November 16, 2025 at 8:26 AM
I’m in London with my daughter for a couple of days.
Curious to discover that I can’t DM here in the UK on Bluesky unless I go through an age verification process.
But it seems that I can still post publicly.
Curious to discover that I can’t DM here in the UK on Bluesky unless I go through an age verification process.
But it seems that I can still post publicly.
I just signed an NDA with a massive tech company you've heard of - and quite likely given lots of money to.
I'm surprised by how reasonable the NDA is. I've signed far more onerous ones with obscure companies.
(And yes, this NDA allows me to mention that it exists. 😅 )
I'm surprised by how reasonable the NDA is. I've signed far more onerous ones with obscure companies.
(And yes, this NDA allows me to mention that it exists. 😅 )
November 14, 2025 at 7:29 AM
I just signed an NDA with a massive tech company you've heard of - and quite likely given lots of money to.
I'm surprised by how reasonable the NDA is. I've signed far more onerous ones with obscure companies.
(And yes, this NDA allows me to mention that it exists. 😅 )
I'm surprised by how reasonable the NDA is. I've signed far more onerous ones with obscure companies.
(And yes, this NDA allows me to mention that it exists. 😅 )
It was amazing of @ianlandsman.com to offer to do this. The Bootstrapped lives on as an archive - a relic of sorts.
Recently @steveofmcleod.com announced he's stopping the Bootstrapped podcast. A show I started with Andrey Butov in 2013 and which Steve has shepherded since 2019
Steve graciously transitioned the show back to me, and I'll continue to maintain the site as an archive of early Bootstrapper podcasting
Steve graciously transitioned the show back to me, and I'll continue to maintain the site as an archive of early Bootstrapper podcasting
November 14, 2025 at 6:49 AM
It was amazing of @ianlandsman.com to offer to do this. The Bootstrapped lives on as an archive - a relic of sorts.
I just found out a competitor closed down.
I feel for them - as a fellow founder you know how much work goes into creating a product, and how hard the decision is to close it down.
Our approaches differed: they were sales-led and charged $30K/year. We prefer self-service, at ~$100/month.
I feel for them - as a fellow founder you know how much work goes into creating a product, and how hard the decision is to close it down.
Our approaches differed: they were sales-led and charged $30K/year. We prefer self-service, at ~$100/month.
November 13, 2025 at 10:38 AM
I just found out a competitor closed down.
I feel for them - as a fellow founder you know how much work goes into creating a product, and how hard the decision is to close it down.
Our approaches differed: they were sales-led and charged $30K/year. We prefer self-service, at ~$100/month.
I feel for them - as a fellow founder you know how much work goes into creating a product, and how hard the decision is to close it down.
Our approaches differed: they were sales-led and charged $30K/year. We prefer self-service, at ~$100/month.
Something I just wrote in a private chat about podcasting:
“It’s quite amazing how talking into a microphone for 30 minutes each week and then pushing ‘publish’ makes people think you are an authority in something.”
(In case it sounds negative, I mean this in a very positive way.)
“It’s quite amazing how talking into a microphone for 30 minutes each week and then pushing ‘publish’ makes people think you are an authority in something.”
(In case it sounds negative, I mean this in a very positive way.)
November 13, 2025 at 7:09 AM
Something I just wrote in a private chat about podcasting:
“It’s quite amazing how talking into a microphone for 30 minutes each week and then pushing ‘publish’ makes people think you are an authority in something.”
(In case it sounds negative, I mean this in a very positive way.)
“It’s quite amazing how talking into a microphone for 30 minutes each week and then pushing ‘publish’ makes people think you are an authority in something.”
(In case it sounds negative, I mean this in a very positive way.)
“Have you tried SEO? or Google Ads? What about A/B testing?”
- my well-meaning freelancers who don’t realise just how long I’ve been doing this “making and selling software on the Internet” gig.
- my well-meaning freelancers who don’t realise just how long I’ve been doing this “making and selling software on the Internet” gig.
November 12, 2025 at 5:09 PM
“Have you tried SEO? or Google Ads? What about A/B testing?”
- my well-meaning freelancers who don’t realise just how long I’ve been doing this “making and selling software on the Internet” gig.
- my well-meaning freelancers who don’t realise just how long I’ve been doing this “making and selling software on the Internet” gig.
I finally put an end to Bootstrapped, my old podcast, that had dwindled away to near abandonment.
bootstrapped.fm/episodes/243...
bootstrapped.fm/episodes/243...
#243: The End | Bootstrapped
The time has come to finally put this mostly abandoned podcast to rest. It's kind of a sad day for me but it is time to do this.
Thank you listeners, thank you to Ian Landsman and Andrey Butov who ga...
bootstrapped.fm
November 11, 2025 at 3:47 PM
I finally put an end to Bootstrapped, my old podcast, that had dwindled away to near abandonment.
bootstrapped.fm/episodes/243...
bootstrapped.fm/episodes/243...
Does your job involve a risk of occasional death threats?
A community manager's job does, sometimes.
John Lloyd told me of his experience with this darker side of his job. It's not a pleasant thing to experience.
Listen here: featureupvote.com/thecommunity...
A community manager's job does, sometimes.
John Lloyd told me of his experience with this darker side of his job. It's not a pleasant thing to experience.
Listen here: featureupvote.com/thecommunity...
When players take it too far ft. Community Manager John Lloyd - Feature Upvote
(You can also watch this episode on YouTube.) Today’s guest is John Lloyd, Community Lead at The Path, a UK-based games marketing agency. John’s journey into community management began long before his...
featureupvote.com
November 11, 2025 at 1:42 PM
Does your job involve a risk of occasional death threats?
A community manager's job does, sometimes.
John Lloyd told me of his experience with this darker side of his job. It's not a pleasant thing to experience.
Listen here: featureupvote.com/thecommunity...
A community manager's job does, sometimes.
John Lloyd told me of his experience with this darker side of his job. It's not a pleasant thing to experience.
Listen here: featureupvote.com/thecommunity...
A problem with working with people in the video games industry: many of them start their working day much later than I start mine.
Perhaps I should follow their lead?
Perhaps I should follow their lead?
November 10, 2025 at 9:37 AM
A problem with working with people in the video games industry: many of them start their working day much later than I start mine.
Perhaps I should follow their lead?
Perhaps I should follow their lead?
In a PR, Copilot chastised me for using a British spelling in a code comment instead of an American spelling - and had no other feedback.
It truly is like experiencing the most annoying nitpicking colleague.
It truly is like experiencing the most annoying nitpicking colleague.
November 5, 2025 at 11:00 AM
In a PR, Copilot chastised me for using a British spelling in a code comment instead of an American spelling - and had no other feedback.
It truly is like experiencing the most annoying nitpicking colleague.
It truly is like experiencing the most annoying nitpicking colleague.
I really like this quote on NOT hiring a product manager too soon.
It's from an interview with a bootstrapping founder for Kill the HiPPO, the book I'm writing.
It's from an interview with a bootstrapping founder for Kill the HiPPO, the book I'm writing.
November 4, 2025 at 10:37 AM
I really like this quote on NOT hiring a product manager too soon.
It's from an interview with a bootstrapping founder for Kill the HiPPO, the book I'm writing.
It's from an interview with a bootstrapping founder for Kill the HiPPO, the book I'm writing.
The latest episode of my podcast The Community Lounge has - quite unexpectedly - done really well.
The episode is currently at almost 1000 views on YouTube alone. Anyone who podcasts knows that, biiiiiig podcasts excepted, this is a Very Rare Thing Indeed!
The episode is currently at almost 1000 views on YouTube alone. Anyone who podcasts knows that, biiiiiig podcasts excepted, this is a Very Rare Thing Indeed!
November 3, 2025 at 5:53 PM
The latest episode of my podcast The Community Lounge has - quite unexpectedly - done really well.
The episode is currently at almost 1000 views on YouTube alone. Anyone who podcasts knows that, biiiiiig podcasts excepted, this is a Very Rare Thing Indeed!
The episode is currently at almost 1000 views on YouTube alone. Anyone who podcasts knows that, biiiiiig podcasts excepted, this is a Very Rare Thing Indeed!
I very much enjoyed Ben Elton’s autobiography.
Having grown up in NZ and Australia, I was surprised to learn that he was an on-screen celebrity in the UK.
I knew of him as a writer (Young Ones, page-turner comic novels etc) and occasional fill-in TV host when the regular host was away.
Having grown up in NZ and Australia, I was surprised to learn that he was an on-screen celebrity in the UK.
I knew of him as a writer (Young Ones, page-turner comic novels etc) and occasional fill-in TV host when the regular host was away.
November 2, 2025 at 7:22 AM
I very much enjoyed Ben Elton’s autobiography.
Having grown up in NZ and Australia, I was surprised to learn that he was an on-screen celebrity in the UK.
I knew of him as a writer (Young Ones, page-turner comic novels etc) and occasional fill-in TV host when the regular host was away.
Having grown up in NZ and Australia, I was surprised to learn that he was an on-screen celebrity in the UK.
I knew of him as a writer (Young Ones, page-turner comic novels etc) and occasional fill-in TV host when the regular host was away.
Awesome episode of @myperfectconsole.bsky.social podcast.
There’s powerful themes in this one, such as growing up as a kid of immigrants.
And the emptiness, loneliness - and maybe even guilt - that can come with unexpected success.
shows.acast.com/my-perfect-c...
There’s powerful themes in this one, such as growing up as a kid of immigrants.
And the emptiness, loneliness - and maybe even guilt - that can come with unexpected success.
shows.acast.com/my-perfect-c...
Rami Ismail, gamemaker (Nuclear Throne, Ridiculous Fishing, Luftrausers, Australia Did It). | My Perfect Console with Simon Parkin
shows.acast.com
October 30, 2025 at 3:30 PM
Awesome episode of @myperfectconsole.bsky.social podcast.
There’s powerful themes in this one, such as growing up as a kid of immigrants.
And the emptiness, loneliness - and maybe even guilt - that can come with unexpected success.
shows.acast.com/my-perfect-c...
There’s powerful themes in this one, such as growing up as a kid of immigrants.
And the emptiness, loneliness - and maybe even guilt - that can come with unexpected success.
shows.acast.com/my-perfect-c...
"“The 70% rule: If you’re roughly 70% happy with a piece of writing you’ve produced, you should publish it."
Read this today. It's good.
From: ckarchive.com/b/wvu2hghk5m...
Read this today. It's good.
From: ckarchive.com/b/wvu2hghk5m...
October 30, 2025 at 12:08 PM
"“The 70% rule: If you’re roughly 70% happy with a piece of writing you’ve produced, you should publish it."
Read this today. It's good.
From: ckarchive.com/b/wvu2hghk5m...
Read this today. It's good.
From: ckarchive.com/b/wvu2hghk5m...
I just finished recording a episode of The Community Lounge podcast with a YouTuber as the guest.
Which means he has decent mic, headphones, and camera, set up correctly, and used well.
Makes such a difference at our end when we get high quality raw video and audio!
Which means he has decent mic, headphones, and camera, set up correctly, and used well.
Makes such a difference at our end when we get high quality raw video and audio!
October 29, 2025 at 1:29 PM
I just finished recording a episode of The Community Lounge podcast with a YouTuber as the guest.
Which means he has decent mic, headphones, and camera, set up correctly, and used well.
Makes such a difference at our end when we get high quality raw video and audio!
Which means he has decent mic, headphones, and camera, set up correctly, and used well.
Makes such a difference at our end when we get high quality raw video and audio!
It's a buzz seeing what parts of Kill the HiPPO, my book-in-progress, resonate with beta readers.
Read the newest chapter - "The Big Rocks Go First" - in the beta version of Kill the HiPPO here: helpthisbook.com/steve-mcleod...
Read the newest chapter - "The Big Rocks Go First" - in the beta version of Kill the HiPPO here: helpthisbook.com/steve-mcleod...
October 29, 2025 at 7:27 AM
It's a buzz seeing what parts of Kill the HiPPO, my book-in-progress, resonate with beta readers.
Read the newest chapter - "The Big Rocks Go First" - in the beta version of Kill the HiPPO here: helpthisbook.com/steve-mcleod...
Read the newest chapter - "The Big Rocks Go First" - in the beta version of Kill the HiPPO here: helpthisbook.com/steve-mcleod...
"build only the bare minimum features"
It's amazing - or maybe not amazing at all - how many times I've heard variants of this from people I've interviewed for the book I'm writing on how bootstrapped founders choose what feature to build next.
It's amazing - or maybe not amazing at all - how many times I've heard variants of this from people I've interviewed for the book I'm writing on how bootstrapped founders choose what feature to build next.
October 28, 2025 at 10:09 AM
"build only the bare minimum features"
It's amazing - or maybe not amazing at all - how many times I've heard variants of this from people I've interviewed for the book I'm writing on how bootstrapped founders choose what feature to build next.
It's amazing - or maybe not amazing at all - how many times I've heard variants of this from people I've interviewed for the book I'm writing on how bootstrapped founders choose what feature to build next.
I sometimes watch Only Connect; I do the NYT puzzles every morning.
There's a fun-to-watch battle going on between them about NYT's "Connections" daily puzzle (which is more than just "inspired" by Only Connect).
Today's Connections puzzle sent a very clear message to Only Connect.
There's a fun-to-watch battle going on between them about NYT's "Connections" daily puzzle (which is more than just "inspired" by Only Connect).
Today's Connections puzzle sent a very clear message to Only Connect.
October 27, 2025 at 7:38 AM
I sometimes watch Only Connect; I do the NYT puzzles every morning.
There's a fun-to-watch battle going on between them about NYT's "Connections" daily puzzle (which is more than just "inspired" by Only Connect).
Today's Connections puzzle sent a very clear message to Only Connect.
There's a fun-to-watch battle going on between them about NYT's "Connections" daily puzzle (which is more than just "inspired" by Only Connect).
Today's Connections puzzle sent a very clear message to Only Connect.
“Hey, Steve! Thank you for the amazing platform Feature Upvote.”
Some people really know how to start an email.
(That’s from one of our customers at a video game publisher.)
Some people really know how to start an email.
(That’s from one of our customers at a video game publisher.)
October 25, 2025 at 7:29 AM
“Hey, Steve! Thank you for the amazing platform Feature Upvote.”
Some people really know how to start an email.
(That’s from one of our customers at a video game publisher.)
Some people really know how to start an email.
(That’s from one of our customers at a video game publisher.)
You should read Ian’s blog post.
It is unusual to have this longevity in a software product.
(Although I do know a few other family-run small-scale software firms like Ian’s that have been around for years!)
It is unusual to have this longevity in a software product.
(Although I do know a few other family-run small-scale software firms like Ian’s that have been around for years!)
I wrote up a few thoughts on HelpSpot turning 20 today ianlandsman.com/helpspot-tur...
HelpSpot Turns 20
ianlandsman.com
October 24, 2025 at 5:56 PM
You should read Ian’s blog post.
It is unusual to have this longevity in a software product.
(Although I do know a few other family-run small-scale software firms like Ian’s that have been around for years!)
It is unusual to have this longevity in a software product.
(Although I do know a few other family-run small-scale software firms like Ian’s that have been around for years!)