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Bootstrapped

Ian Landsmanbootstrapped.fm
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.
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Episodes

#243: The End

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.

Nov 11, 20252 minEp. 243

#242: Boredeom

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 p...

Jul 16, 202512 minEp. 242

#241: Podcasting

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 product The Community Lounge , the podcast I'm creating as a business tool...

May 14, 202516 minEp. 241

#240: Why I repositioned Feature Upvote to the video game industry

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 .

Apr 21, 202518 minEp. 240

#239: Our Business Heroes with The Gross Profit Podcast

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 podcast Feature Upvote , my B2B SaaS My B2B SaaS coaching services...

Mar 01, 202439 minEp. 239

#238: B2B SaaS design with Nathan Powell

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/

Jun 23, 202334 minEp. 238

#237: Michael Koper, founder of Nusii

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, Nusii Michael on Twitter .

Mar 12, 202326 minEp. 237

#236: Steve McLeod, founder of Feature Upvote

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 Upv...

Dec 02, 202234 minEp. 236

#235: Maeva Cifuentes, founder of Flying Cat Marketing

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 Marketing Maeva on LinkedIn Product-led SEO by Eli Schwartz...

Nov 18, 202232 minEp. 235

#234: Ed's marketing catchup

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 Upvote Ed’s company, OpenCage Geomob website April Dunford's "Toilet talk" Ed's newly published Geocoding Buyer's Guide...

Oct 28, 202233 minEp. 234

#233: Running a lifestyle business and proud of it

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.com Andy's products: Easy Data Transform , PerfectTable...

Oct 14, 202229 minEp. 233

#232: Running a WordPress agency, with Marc Jenkins of 16by9

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, 16by9 Marc's Unoffice Hours Steve’s company, Feature Upvote The Bootstrapped website , designed and created by 16by9...

Sep 30, 202229 minEp. 232

#231: Bad support loses customers, and payment failures

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 Upvote Ed’s company, OpenCage

Sep 16, 202234 minEp. 231

#230: Introducing Pushing to Production

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 podcast Ed’s company, OpenCage Bootstrapped #228 , where I explain why this show will end with episode #250....

Aug 19, 202233 minEp. 230

#229: Saying no to a generous acquisition offer, with Simon Bennett of SnapShooter

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, SnapShooter Simon's new podcast for SaaS founders, Ship SaaS Faster SnapShooter's podcast, Pushing to Production Versoly My company, Feature Upvote Simon on Twitter...

Aug 05, 202231 minEp. 229

#228: How to get backlinks (without feeling dirty)

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 Upvote Tooltester's email deliverability report Rand Fishkin's company, SparkToro Posts I got on the blogs of Postmark , Cloudinary , and ChartMogul My guest post on Andy Brice's Successful Software blog My guest post on HelpSpot's blog Ou...

Jul 15, 202223 minEp. 228

#227: Joining TinySeed with Nick Swan of SEOTesting.com

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.com Nick's previous appearance on Bootstrapped #177 Nick's investor, TinySeed Nick on Twitter Steve's com...

Jul 01, 202236 minEp. 227

#226: Sponsoring events, podcasts, and newsletters with Peldi @ Balsamiq

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 Upvote Ed's company, OpenCage Steve on Twitter Email: steve@bootstrapped.fm...

Jun 17, 202233 minEp. 226

#225: BoS Europe 2022 retrospective

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 website Business of Software podcast Joe Leech's website Joe on Twitter: https://twitter.com/mrjoe Steve’s co...

Jun 03, 202228 minEp. 225

#224: Recalibrating prices, and Postmark got acquired

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, g...

May 20, 202231 minEp. 224

#223: When customer payments fail

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 Ephemeris Business of Software conference Ed's company, OpenCage . Steve's company, Feature Upvote ....

May 06, 202231 minEp. 223

#222: Pierre de Wulf, co-founder of ScrapingBee

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

Apr 22, 202235 minEp. 222

#221: Brian Sierakowski of Baremetrics

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.

Apr 15, 202232 minEp. 221

#220: Adventures in Abandonware and WordPress

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.

Apr 08, 202231 minEp. 220

#219: Leaving bootstrapper life to be an employee again, with John Ndege

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...

Apr 01, 202229 minEp. 219

#218: London, in-person events, crowded pubs

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 steve@bootstrapped.fm...

Mar 25, 202226 minEp. 218

#217: Brian Casel of ZipMessage

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 ge...

Mar 18, 202230 minEp. 217

#216: Trademarking your bootstrapped business

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 .

Mar 11, 202227 minEp. 216

#214: I hired a marketer

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.

Feb 25, 202231 minEp. 214
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