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Bootstrapped

by Ian Landsman

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

  1. #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...

  2. #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…

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  3. #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…

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  4. #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...

  5. #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...

  6. #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:...

  7. #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.

  8. #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...

  9. #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,...

  10. #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…

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  11. #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,...

  12. #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...

  13. #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...

  14. #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...

  15. #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…

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  16. #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...

  17. #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...

  18. #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,...

  19. #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...

  20. #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…

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  21. #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....

  22. #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

  23. #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...

  24. #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...

  25. #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...

  26. #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...

  27. #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...

  28. #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...

  29. #215: The domain name change that didn't go as planned, with Robert Brandl of ToolTester.com

    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.

  30. #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.

  31. #213: Charles Perry, founder of RelaNet

    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....

  32. #212: When, if ever, should we refuse a customer?

    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...

  33. #211: Strengthening company culture in a remote team with Peldi of Balsamiq

    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...

  34. #210: 50 tips for running a stress-free SaaS part 2

    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.

  35. #209: 50 tips for running a stress-free SaaS part 1

    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...

  36. #208: The dismal deeds of a desperate competitor

    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.

  37. #207: Our goals for 2022

    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…

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  38. #206: Looking back at our goals for 2021

    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.

  39. #205: A rapid Saber Feedback update

    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...

  40. #204: Ed can speak again

    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.

  41. #203: A recap of the interview mini-season

    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...

  42. #202: Bridget Harris, co-founder of YouCanBookMe

    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...

  43. #201: Running an email newsletter business, with Peter Cooper of Cooperpress

    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: Cooperpress Peter on Twitter

  44. #200: Positioning for bootstrappers with April Dunford

    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 website April's book, Obviously Awesome April on Twitter

  45. #199: Creating a successful podcast with Jane Portman of UI Breakfast

    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.…

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  46. #198: Backing up 170 Petabytes of customer data, with Simon Bennett of SnapShooter

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

  47. #197: Life is unpredictable, and a pricing experiment

    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...

  48. #196: Our Mental Wellbeing as Bootstrappers, with Robin Warren

    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:...

  49. #195: Back to School

    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.

  50. #194: We talk about our vacations

    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.

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ABOUT THIS SHOW

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.

HOSTED BY

Ian Landsman

CATEGORIES

business technology

Frequently Asked Questions

How many episodes does Bootstrapped have?

Bootstrapped currently has 243 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Bootstrapped about?

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...

How often does Bootstrapped release new episodes?

Bootstrapped publishes regularly with 243 episodes available. Check the episode list for the typical release schedule.

Where can I listen to Bootstrapped?

You can listen to Bootstrapped on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Bootstrapped?

Bootstrapped is created and hosted by Ian Landsman.
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