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
Steve McLeod
@steveofmcleod.com
· Jun 21
Kill the HiPPO - Add a Button; Remove a Button - Help This Book
Read "Kill the HiPPO" by Steve McLeod and Siew Ann Tan on Help This Book
helpthisbook.com
A new draft chapter of my book “Kill the HiPPO: How bootstrapped software companies decide what feature to build next” is ready for you to read.
“Add a button; remove a button”
I’m particularly happy with this chapter:
helpthisbook.com/steve-mcleod...
“Add a button; remove a button”
I’m particularly happy with this chapter:
helpthisbook.com/steve-mcleod...
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!)
You know that tiresome friend who spent time in, say, Italy or Spain or Japan, and whenever you go to an Italian, etc restaurant with them, they complain that the food isn’t how isn’t authentic enough?
That’s me with Lebanese food.
Except this place I went to last night that made PERFECT labneh.
That’s me with Lebanese food.
Except this place I went to last night that made PERFECT labneh.
October 24, 2025 at 8:34 AM
You know that tiresome friend who spent time in, say, Italy or Spain or Japan, and whenever you go to an Italian, etc restaurant with them, they complain that the food isn’t how isn’t authentic enough?
That’s me with Lebanese food.
Except this place I went to last night that made PERFECT labneh.
That’s me with Lebanese food.
Except this place I went to last night that made PERFECT labneh.
Talking to a potential new customer yesterday:
"My colleague found your tool, and… and was like, hey, look at this, I think this is what we need, and I was like, oh my gosh, yes it is, that looks perfect!"
"My colleague found your tool, and… and was like, hey, look at this, I think this is what we need, and I was like, oh my gosh, yes it is, that looks perfect!"
October 23, 2025 at 11:04 AM
Talking to a potential new customer yesterday:
"My colleague found your tool, and… and was like, hey, look at this, I think this is what we need, and I was like, oh my gosh, yes it is, that looks perfect!"
"My colleague found your tool, and… and was like, hey, look at this, I think this is what we need, and I was like, oh my gosh, yes it is, that looks perfect!"
The barrista attempted a Halloween-theme latte art.
October 22, 2025 at 8:14 AM
The barrista attempted a Halloween-theme latte art.
A customer reported a bug, and sent a video recording showing the bug.
While watching the video, I noticed the customer had an awkward workflow. It was awkward not because of them, but because of our user interface.
That's a problem that we need to fix before adding any new features.
1/2
While watching the video, I noticed the customer had an awkward workflow. It was awkward not because of them, but because of our user interface.
That's a problem that we need to fix before adding any new features.
1/2
October 21, 2025 at 9:02 AM
A customer reported a bug, and sent a video recording showing the bug.
While watching the video, I noticed the customer had an awkward workflow. It was awkward not because of them, but because of our user interface.
That's a problem that we need to fix before adding any new features.
1/2
While watching the video, I noticed the customer had an awkward workflow. It was awkward not because of them, but because of our user interface.
That's a problem that we need to fix before adding any new features.
1/2
I just discovered that Stripe is pulling this nonsense with my customers:
4% "conversion fee" to "guarantee the exchange rate".
i.e. 4% rent extraction for zero benefit to me and zero benefit to my customer.
Seeing how Stripe has changed over time kinda makes me sad.
4% "conversion fee" to "guarantee the exchange rate".
i.e. 4% rent extraction for zero benefit to me and zero benefit to my customer.
Seeing how Stripe has changed over time kinda makes me sad.
October 21, 2025 at 8:31 AM
I just discovered that Stripe is pulling this nonsense with my customers:
4% "conversion fee" to "guarantee the exchange rate".
i.e. 4% rent extraction for zero benefit to me and zero benefit to my customer.
Seeing how Stripe has changed over time kinda makes me sad.
4% "conversion fee" to "guarantee the exchange rate".
i.e. 4% rent extraction for zero benefit to me and zero benefit to my customer.
Seeing how Stripe has changed over time kinda makes me sad.
Sometimes I feel that my main task in running my company is acting as an extremely over-qualified router of emails.
Forward this, forward that, archive this, delete that.
Forward this, forward that, archive this, delete that.
October 21, 2025 at 8:17 AM
Sometimes I feel that my main task in running my company is acting as an extremely over-qualified router of emails.
Forward this, forward that, archive this, delete that.
Forward this, forward that, archive this, delete that.
When it comes to angry players, don’t fight fire with fire!
That's from my chat with CM and award-winning accessibility advocate @jarvdusa.bsky.social on the Community Lounge podcast.
Listen to the full episode: featureupvote.com/thecommunity...
That's from my chat with CM and award-winning accessibility advocate @jarvdusa.bsky.social on the Community Lounge podcast.
Listen to the full episode: featureupvote.com/thecommunity...
October 20, 2025 at 9:34 AM
When it comes to angry players, don’t fight fire with fire!
That's from my chat with CM and award-winning accessibility advocate @jarvdusa.bsky.social on the Community Lounge podcast.
Listen to the full episode: featureupvote.com/thecommunity...
That's from my chat with CM and award-winning accessibility advocate @jarvdusa.bsky.social on the Community Lounge podcast.
Listen to the full episode: featureupvote.com/thecommunity...
Making your software provide helpful error messages when something goes wrong is hard.
Example:
Example:
October 20, 2025 at 6:35 AM
Making your software provide helpful error messages when something goes wrong is hard.
Example:
Example:
I’ve read The Twits to my daughter multiple times.
Today we watched the new Netflix film The Twits.
Ah, what? This movie has almost nothing in common with the book. To say it is “loosely based” on the book is a biiiig stretch.
Today we watched the new Netflix film The Twits.
Ah, what? This movie has almost nothing in common with the book. To say it is “loosely based” on the book is a biiiig stretch.
October 19, 2025 at 4:24 PM
I’ve read The Twits to my daughter multiple times.
Today we watched the new Netflix film The Twits.
Ah, what? This movie has almost nothing in common with the book. To say it is “loosely based” on the book is a biiiig stretch.
Today we watched the new Netflix film The Twits.
Ah, what? This movie has almost nothing in common with the book. To say it is “loosely based” on the book is a biiiig stretch.
Wise words from Anil here.
What I find really annoying is people in camp # 2, if I’m not one of them, portraying me as being in camp #1.
What I find really annoying is people in camp # 2, if I’m not one of them, portraying me as being in camp #1.
I get the point that's trying to be made here, but it's actually inaccurate. The *MAJORITY* of actual practitioners in the tech industry have a position that is neither of these, it's merely getting drowned out by these two loud positions. The most common belief in the tech industry is simple:
There are basically only two positions in the debate about AI.
1. I’ve barely invested any time in learning how to use it effectively. AI sucks.
2. I’ve invested in learning how to use this tool. Holy cow, it’s transformational.
Position #1 has lower barriers to entry.
1. I’ve barely invested any time in learning how to use it effectively. AI sucks.
2. I’ve invested in learning how to use this tool. Holy cow, it’s transformational.
Position #1 has lower barriers to entry.
October 17, 2025 at 12:32 PM
Wise words from Anil here.
What I find really annoying is people in camp # 2, if I’m not one of them, portraying me as being in camp #1.
What I find really annoying is people in camp # 2, if I’m not one of them, portraying me as being in camp #1.