Bootstrapped

Bootstrapped episodes:

• 06.23.2023

  #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.

  
• 03.12.2023

  #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.

  
• 12.02.2022

  #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...

  
• 11.18.2022

  #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...

  
• 10.28.2022

  #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.

  
• 10.14.2022

  #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....

  
• 09.30.2022

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

  Marc Jenkins runs 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...

  
• 09.16.2022

  #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...

  
• 08.19.2022

  #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...

  
• 08.05.2022

  #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,...

  
• 07.15.2022

  #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.

  
• 07.01.2022

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

  Nick Swan from SEOTesting.com discusses how he took on a co-founder for his already-established business, why he decided to no longer be a 1-person show, and most importantly how he sold a small part of his company in order to...

  
• 06.17.2022

  #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...

  
• 06.03.2022

  #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...

  
• 05.20.2022

  #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...

  
• 05.06.2022

  #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.

  
• 04.22.2022

  #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.

  
• 04.15.2022

  #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...

  
• 04.08.2022

  #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...

  
• 04.01.2022

  #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 was a bootstrapper, he launched and grew a product, and he ultimately sold it. Afterwards, he went back to being an...

  
• 03.25.2022

  #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.

  
• 03.18.2022

  #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...

  
• 03.11.2022

  #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.

  
• 03.04.2022

  #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.

  
• 02.25.2022

  #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.

  
• 02.18.2022

  #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...

  
• 02.11.2022

  #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...

  
• 02.04.2022

  #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...

  
• 01.28.2022

  #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.

  
• 01.21.2022

  #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...

  
• 01.14.2022

  #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...

  
• 12.24.2021

  #207: Our goals for 2022

  Ed and I discuss the goals we'd like to achieve in 2022.

  
• 12.17.2021

  #206: Looking back at our goals for 2021

  Back in episode 163, Ed and I set our goals for 2021. In this episode, 206, we look back at those goals and we ask ourselves, how well did we do in achieving them?

  
• 12.10.2021

  #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!

  
• 12.03.2021

  #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.

  
• 11.26.2021

  #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...

  
• 11.19.2021

  #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...

  
• 11.12.2021

  #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.

  
• 11.05.2021

  #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.

  
• 10.22.2021

  #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...

  
• 10.15.2021

  #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 * why Simon charged his first customer just $2/month - and quickly learned to charge much more * how the pandemic pushed him...

  
• 10.01.2021

  #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...

  
• 09.24.2021

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

  Three-time guest Robin Warren 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...

  
• 09.17.2021

  #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.

  
• 09.10.2021

  #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.

  
• 09.03.2021

  #193: The fine details of the Saber Feedback acquisition

  If you've ever thought of selling your business, or acquiring one, you'll enjoy this episode. Matt Zeunert, founder of DebugBear, was curious about the details of my acquisition of Saber Feedback. So we switch roles for this episode, and the...

  
• 08.27.2021

  #192: How the pandemic overturned my business, with Mark Littlewood of Business of Software

  Mark Littlewood runs the Business of Software, a series of annual conferences to help us run our software companies better. Mark very openly shares how the pandemic has hit his business, and his need to adapt almost overnight. We talk about...

  
• 08.23.2021

  #191: On quietly successful SaaS businesses, and saying goodbye to our forum

  In this solo episode, I talk about successful yet quiet SaaS business all around us. I also tell the full story of why our forum has been closed and put permanently into archive mode.

  
• 08.13.2021

  #190: Resellers and product-based podcasts, with Peldi of Balsamiq

  Peldi, founder of Balsamiq, drops by. We discuss two unrelated topics. First, resellers - why they exist and how to accommodate them. Second, the challenges and benefits of having a podcast for your product.

  
• 08.06.2021

  #189: The agony of the enterprise sale process, with Ed Freyfogle

  Ed and Steve go in deep on some enterprise sales work they've both been doing lately for their bootstrapped, mostly self-service SaaS products.