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 gave me this podcast to take over, and thank you to Ed Freyfogle for co-hosting many episodes.So long, farewell, adios.

When you run your own little software company, be it a SaaS or old school downloadable software, and you've been doing it for several years, and you've got through the major initial challenges that were interesting and fun and rewarding to conquer in the first few years, and you've now got to that point where your product revenue is stable, and your product is pretty much feature complete, it becomes boring.Here's 3 projects I've been working on to alleviate my bootstrapper boredom, while not putting my company in peril.Mentioned in this episode:My coaching: https://steveofmcleod.com/My book-in-progress: https://killthehippo.com/My public speaking, as recorded at Business of Software Europe in April 2025: https://businessofsoftware.org/playlists/playlist-europe-2025/#SM

In this episode, I talk about how I'm using podcasting as a business tool. Not as a guest, not to promote my product, not as an advertiser, but as a way to build up and strengthen my network amongst my "Ideal Customer Profile" in the video games industry.Mentioned in this episode:Feature Upvote, my SaaS productThe Community Lounge, the podcast I'm creating as a business tool

I want to tell you what's happening with my product, Feature Upvote, over the last year or so. I've dramatically changed the positioning, to be a feedback management platform for the video games industry.Here's the story of why I repositioned - and how I did it.Check out the new "video games industry"-focused Feature Upvote home page.

I was recently a guest on The Gross Profit podcast, hosted by James Kennedy. In that interview, James and I talked about our business heros, and well, it seemed to me that the conversation was a perfect fit for this podcast too.So, with James's permission, I'm sharing with you here the entire episode of The Gross Profit podcast in which I was interviewed.The Gross Profit podcastFeature Upvote, my B2B SaaSMy B2B SaaS coaching services

I chat with Nathan Powell, freelance product designer whose work these days is mainly with B2B SaaS. We chat about how developer founders can go about improving their app's UX and general design.Mentioned in this episode:Nathan's website: https://nathanjpowell.com/Descript: https://www.descript.com/

I chat with Michael Koper, founder of Nusii. We talk about what it's like when your product spends several years at a revenue plateau.Mentioned in this episode:Michael's company, NusiiMichael on Twitter.

I'm the guest on my own podcast! A year ago, Ben Pages joined my company, Feature Upvote, to be our marketing manager. Ben had questions about the early days of Feature Upvote, and how this product came to be. He also wanted to know the origin of my low-stress approach to running a business. We thought, why keep this conversation to ourselves? Why not record it as a podcast interview, and share it with you? And that is exactly what we did for this episode.Mentioned in this episode:Feature UpvoteA blog post we mentioned: What I learnt in 2018 while running Feature Upvote.The Bob Dylan quote I mis-remembered in this episode is:A man is a success if he gets up in the morning and goes to bed at night and in between does what he wants to do.

I chat with Maeva Cifuentes, founder and CEO of Flying Cat Marketing, an SEO and content marketing agency. We discuss Maeva's journey from freelance translator to CEO of a successful marketing agency. Maeva also shares with us some practical SEO tips.Mentioned in this episode:Maeva's company, Flying Cat MarketingMaeva on LinkedInProduct-led SEO by Eli Schwartz

My frequent guest co-host Ed Freyfogle tells us about his recent marketing endeavours, including one that was inspired by April Dunford's "toilet talk". Toilet talk, you ask? All will be revealing during this episode.Mentioned in this episode:Steve’s company, Feature UpvoteEd’s company, OpenCageGeomob websiteApril Dunford's "Toilet talk"Ed's newly published Geocoding Buyer's Guide

We have two guests interviewing each other! I invited two friends of the podcast, Andy Brice, and Robin Warren, to chat with each other about what it's like running a lifestyle business in 2022 compared to, say, 10 years ago. Although both Andy and Robin run what they call lifestyle businesses, they've taken different approaches, based on what they want to get out of their business.Mentioned in this episode:Robin's company: bluecatreports.comAndy's products: Easy Data Transform, PerfectTablePlan, Hyper PlanAndy on Twitter: @successfulswAndy's blog: Successful SoftwareRobin on Twitter: @robinwarren

I chat with Marc Jenkins, founder of 16by9, a small web studio that focuses on building WordPress sites. Marc and I talk about what its like to start and build up this type of company, and how, with some careful thinking, you can avoid letting your business become something you never wanted it to be.Mentioned in this episode:Marc's web studio, 16by9Marc's Unoffice HoursSteve’s company, Feature UpvoteThe Bootstrapped website, designed and created by 16by9

I catch up with my frequent co-host, Ed Freyfogle, after a long summer break. Amongst other topics, we discuss how bad customer support will lose you customers. We also talk about yet more payment problems - a common theme on this podcast, and for SaaS businesses in general.Mentioned in this episode:Steve’s company, Feature UpvoteEd’s company, OpenCage

Something a bit different in this episode: we're playing an episode of the new Pushing to Production podcast, where Ed Freyfogle was the guest. It's a conversation about the technical stack Ed's product runs on. Lots of insightful discussion of the tech decisions you need to make in an API-based business.Mentioned in this episode:Pushing to Production podcastEd’s company, OpenCageBootstrapped #228, where I explain why this show will end with episode #250.

Simon Bennett, founder of SnapShooter, returns to the show. We chat about a generous acquisition offer Simon recently received for his company - and why he ultimately decided to not to be acquired. We also chat about Simon's new podcast, Ship SaaS Faster.Mentioned in this episode:Simon's company, SnapShooterSimon's new podcast for SaaS founders, Ship SaaS FasterSnapShooter's podcast, Pushing to ProductionVersolyMy company, Feature UpvoteSimon on Twitter

An effective content strategy for your product requires getting backlinks. In this episode, I share 9 strategies I use for getting backlinks for my product's website - without doing things that make me feel dirty.Mentioned in this episode:My company, Feature UpvoteTooltester's email deliverability reportRand Fishkin's company, SparkToroPosts I got on the blogs of Postmark, Cloudinary, and ChartMogulMy guest post on Andy Brice's Successful Software blogMy guest post on HelpSpot's blogOut of Beta podcastJavalin Java web frameworkSteve on Twitter

I chat with Nick Swan from SEOTesting.com. We discuss how Nick took on a co-founder for his already-established business, why Nick decided to no longer be a 1-person show, and most importantly how Nick sold a small part of his company in order to join TinySeed, a startup accelerator designed for founders who would traditionally bootstrap.Mentioned in this episode:Nick's company, SEOTesting.comNick's previous appearance on Bootstrapped #177Nick's investor, TinySeedNick on TwitterSteve's company, Feature Upvote

We are joined by a good friend of the podcast, Peldi Guilizzoni, to discuss how to go about sponsoring events, newsletters, and podcasts to promote your product. In particular we talk about creative approaches that make your sponsorship stand out.Mentioned in this episode:Peldi's company, Balsamiq, a low-fidelity wireframing tool.Steve's company, Feature UpvoteEd's company, OpenCageSteve on TwitterEmail: [email protected]

I first recorded this episode for the Business of Software podcast. I chat about the experience of attending the recent Business of Software Europe in-person event, together with Joe Leech, who was a speaker at the event.Joe and I shared our thoughts on the event, Joe from the point of view of a speaker at the event, and me as an attendee.Mentioned in this episode:Business of Software websiteBusiness of Software podcastJoe Leech's websiteJoe on Twitter: https://twitter.com/mrjoeSteve’s company, Feature UpvoteSteve on Twitter: https://twitter.com/steveofmcleod

Ed and I talk about how currency fluctuations are affecting our pricing. And we give our opinion on the recent acquisition of Postmark, a bootstrapping success story, by ActiveCampaign.A brief note about an error in this episode: At one point I complain about a customer support problem I once had when trying to sign up for ActiveCampaign. After recording, I realised I had confused ActiveCampaign with CampaignMonitor. Let the record show that I've never had any experience with ActiveCampaign, good or bad! Apologies for my confusion.Mentioned in this episode:Postmark's acquisition announcementSteve's company, Feature UpvoteEd's company, OpenCage

We talk about why we are switching the podcast from weekly to fortnightly for a while. We also discuss headaches when customer payments fail and what we can do to address the problem.Mentioned in this episode:The Photographer's EphemerisBusiness of Software conferenceEd's company, OpenCage.Steve's company, Feature Upvote.

Ed chats with Pierre de Wulf, co-founder of ScrapingBee. Pierre tells us about the time his company almost got acquired - and how the deal fell apart at the final stage.Links:Pierre's company, Scraping Bee.Pierre on Twitter

My co-host Ed Freyfogle chats with Brian Sierakowski, general manager of Baremetrics. Brian stepped in to manage Baremetrics after it was acquired a year or so ago from the founder.Ed and Brian discuss the challenges of taking over a complicated business, Brian's trajectory from SaaS founder himself to running someone else's business, and how changing prices inadvertently gave him the chance to get valuable customer feedback.

Ed and Steve talk about a dilemma Steve is facing. An open source component heavily used by Feature Upvote has become abandoned by the maintainer, and Steve has to make a hard decision about how to deal with this.We also talk about why and how Steve recently moved Feature Upvote's website from Jekyll to Wordpress. Yes, really, Wordpress.

Ed chats with John Ndege, a former bootstrapper, about how it feels no longer being one's own boss. John launched and grew a product, and he ultimately sold it. Afterwards, he went back to being an employee, working for a large corporation. Ed and John discuss the advantages and frustrations you might experience when you choose the path of going back to work for someone else.Links:John's website: https://www.johnndege.com/John on Twitter: https://twitter.com/johnndege

Ed and I chat about Ed's recent trip to London, my upcoming trip to London, the return of in-person events, and getting exposed to ideas and concepts outside of our normal channels.We mentioned Geomob and Business of Software.In or near London? And interested in joining me for a Bootstrapped mini-meetup in central London on the evening of April 6th or 7th? Let me know at [email protected]

I talk with Brian Casel, founder of ZipMessage, an asynchronous video messaging tool.Brian has created several successful products in the past, and sometimes ran them in parallel. But he recently sold his entire portfolio of products to focus on ZipMessage. Brian explains why he made this decision. He also talks about why sometimes you need to shut something down, even if it does seem to be kind of, sort of working.And we talk about the feeling when you realise that a new product is really getting traction.Links:zipmessage.comBrian's podcast, Bootstrapped WebBrian on Twitter

Ed tells me why and how he obtained a trademark for his business. We discuss when it is worthwhile to do this. We then talk about the trouble with having competitors clone your product or website content.Ed mentioned how we got the EU to refund most of the costs of obtaining a trademark. Learn about the EU's "Ideas Powered for business SME Fund" here.

I chat with Robert Brandl, founder of ToolTester.com. We talk about Robert's recent experience changing the domain name of his website. It was an expensive experience, and one that, for a while, did not go to plan.

Ed and I chat about my recent experience hiring a marketing manager for Feature Upvote. Amongst other topics, we discuss how I went about finding the right person.

Ed interviews Charles Perry, founder of RelaNet. Charles was the co-host of Release Notes, a long-running podcast that Charles and his co-host recently ended.It's a great conversation, addressing how, over the years, we change, our industries change, and how sometimes things do come to an end.Charles on TwitterThe Release Notes podcast's back catalog of 450 episodes

We talk about Ed's launch of his new product line.That leads into a meandering conversation about ethics and personal beliefs and values. In particular, when a customer signs up for our product and then we discover that customer is in a business that clashes with our own beliefs and values, what should we do and what can we do?When is it right, ethically or legally, to refuse a customer?

Frequent guest Peldi, founder of Balsamiq, makes another welcome appearance.We talk about some ways to strengthen company culture in a fully-remote team, we discuss advice that Peldi often gives to first-time entrepreneurs, and Peldi tells me why he might finally start with traditional product marketing - 14 years after he launched his product.Find out more about Balsamiq's Office Hours.

Part 2 of Ed Freyfogle's 50 tips for running a stress-free SaaS.There was a lot of good content in this recording and we recorded for much longer than usual. So we have split this recording over two episodes. Part 1 is here.

Ed Freyfogle shares with us his 50 tips for running a stress-free SaaS. This is based on Ed's talk he prepared for MicroConf late last year, but was unable to deliver due to misfortune.There was a lot of good content in this recording and we recorded for much longer than usual. So we have split this recording over two episodes.

This week I go solo and rant about the dismal deeds of a desperate competitor. I also talk about the freedom that bootstrapping gives us to change our approach, our style, our audience while staying true to the nature of what we do.

Ed and I discuss the goals we'd like to achieve in 2022.While we were recording this episode, we had some problems with our recording software. Now I was able to rescue the recording, but you will hear a few audio glitches.In this episode, I mentioned that I'm hiring a part-time digital marketing expert for Feature Upvote. If you know someone who suits the position, please let them know.

Back in episode 163, Ed and I set our goals for 2021. In this episode we look back at those goals and we ask ourselves, how well did we do in achieving them?Steve mentioned the Catalan Christmas tradition of Caga Tió. Here's what Wikipedia has to say about Caga Tió.

I give Ed an update on what I've achieved on Saber Feedback in recent months.A new app design, ripping out the SPA architecture, replacing our payment processor with Paddle, and hiring a marketing assistant. It's been busy!If you have a friend or colleague or acquaintance who you think would enjoy this episode, please let them know about it!

Ed tells us about his accident he had, and the impact it had on his life and business. He also talks about how it got him reflecting about his business.

I conclude the mini season of interviews with a brief summary of the five interviews I conducted. A few weeks ago, my cohost had a cycling that student that broke his jaw. As a result he had to take a break from the podcast while he was recovering. In the meantime, I invited a few people to come onto the podcast and talk about their businesses, their work and themselves.The episodes:#198: Simon Bennett of SnapShooter#199: Jane Portman of UI Breakfast#200: Positioning for bootstrappers with April Dunford#201: Peter Cooper of Cooperpress#202: Bridget Harris, co-founder of YouCanBook.Me

Bridget is co-founder and CEO of YouCanBook.me, an online scheduling tool. I chat with Bridget Harris about the 10-year journey of starting and growing her company as a bootstrapped SaaS. Amongst other things we discuss the financial sacrifices bootstrappers have to make in a rapidly growing business.Links:Bridget's scheduling tool, YouCanBook.me Bridget's email: [email protected] on Twitter

I chat with Peter Cooper, who runs several email newsletters, including JavaScript Weekly, Ruby Weekly, React Status, and Postgres Weekly. These all live under the collective banner of Cooperpress.Links:CooperpressPeter on Twitter

April Dunford has a well-deserved reputation as the expert in product positioning within the tech industry. April and I discussed how bootstrappers can go about product positioning.Links:April's websiteApril's book, Obviously AwesomeApril on Twitter

Jane Portman is the host of UI Breakfast, a podcast covering UI/UX design, products, marketing. Jane recently crossed the 2 million downloads milestone. Jane and I discussed the journey from the first episodes, with almost no listeners, to where she is today.Jane is also co-founder of Userlist. We discuss how Jane's podcasting experience helps with Userlist.Links:The UI Breakfast podcast How to sponsor Jane's podcastUserlistBetter Done Than Perfect podcast

Simon runs SnapShooter, a service that performs scheduled server backups. We discuss:why backups is NOT a dull businesshow the pandemic pushed him to make the jump to full-timecharging his first customer just $2/month - and quickly learning to charge much morea "I did a rm -rf on the wrong server" storyLinks: SnapShooterSimon on Twitter

Ed is recovering from an accident, so Steve goes solo in this episode. Ed's accident gets Steve musing on the unpredictability of life, and what we can do to partly prepare ourselves and our businesses for this.Steve then abruptly changes topic and challenges all listeners to make a bold pricing experiment.Email Steve at steve @ barbarysoftware dot comSteve on Twitter: https://twitter.com/steveofmcleod

Three-time guest Robin Warren, founder of Corrello, achieves "very infrequent guest co-host" status. We chat about a number of aspects of mental wellbeing for bootstrappers - getting out of the house, taking breaks, dealing with boredom, and making your business less dependent on you.Show links:Robin on TwitterBlue Cat Reports websiteBlue Cat Reports on Trello

Ed and Steve talk about the challenge of continuing to learn how to run our businesses better, and the challenges we encounter in ongoing learning.

It's good to take a break!In this episode Ed and I get self-indulgent and talk about our vacations. From time to time we make a tenuous link between our vacations and our bootstrapped businesses.