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