Podcast: Bootstrapped Web | For Entrepreneurs Bootstrapping Web Startups


Bootstrapped Web is for entrepreneurs who are bootstrapping web startups and believe in order to achieve success, we must learn by doing. Interviews with bootstrapped entrepreneurs and case studies in building profitable businesses.

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Recent Episodes

  • Culture & Onboarding

    Brian and Jordan are back for the third week in a row. We talk about their plans for the next couple of weeks (Slovania and BigSnowTinyConf). We also go through a few current and upcoming updates. We pose a few questions including, when you have a new pro...

  • Positioning and Profitability

    We’re back! We’re excited about some winter weather activities and all of our 2020 ideas. We talk about brainstorming, questions, nomenclature, tiny conferences, and profitability. Here are today’s conversation points: Looking back one last time on 2019 J...

  • Back At It

    Today we’re talking about getting back to work after the holiday “festivities”, the inability to unplug, slowing down in December, the themes that ran through 2019, and what our themes for 2020 will be. Here are today’s conversation points: What to do whe...

  • Marketing Plans for 2020

    Brian and Jordan are back! We talk about holiday plans, the work-from-home life and coworking spaces, seeing and working with other human beings, spending all of our money at Starbucks, and the latest in marketing techniques. We talk about our past market...

  • Marketing Loose Ends & Funding Gaps

    Jordan and Brian are back behind the mic before Thanksgiving. Jordan talks about how great it feels to be unnecessary (at work) and various B-to-B and B-to-C marketing techniques. Brian talks about kits, his “new trialers”, and Processkit updates. They al...

  • Post-Launch & Code Freezes

    Today we’re live and in a rush since Jordan has to take his kids to lunch on their off-day!  We talk about post-Halloween shenanigans, Brian’s 37th birthday (at least, he’s not 40), the stats and news from Process Kit’s launch, capturing the creative...

  • Product Brain vs Marketing Brain

    Brian and (a sick) Jordan are back talking about upcoming Halloween festivities, what they missed out on by missing MicroConf (in Croatia), their thoughts on SEO, product vs. marketing, new podcasting ideas, and the new ProcessKit website. Here are today’...

  • So Much for That Plan

    Jordan and Brian are back with updates (even if they’re not so great). Brain updates us on the developments (or lack thereof) with his developer and how communication issues have played a part in the lack of progress. He also talks about how to move forwa...

  • Continuous Adjustments

    Jordan and Brian are back in the studio. Today the main focus is on the continuous adjustments needed in the software industry. They also quickly cover the trend of SaaS companies doing conferences and community-based marketing. Jordan talks about how gre...

  • Never Enough MRR

    Jordan and Brian are back to a regular podcasting schedule. Brian spent the weekend at a retreat/mastermind group at Martha’s Vineyard. Meanwhile, Jordan was at the Striped Conference. After a quick update, Jordan and Brian talk about the latest episode o...

  • Rabbit Holes Within Rabbit Holes

    It’s September, which means we’re talking about the changing of the seasons: kids are back in school, we’re gearing up for Black Friday, updating websites, and checking our numbers. Brian talks about his email marketing, hiring developers, and changing we...

  • Move It up and Accelerate the Plan

    Jordan is back! We talk about what we’ve been up to: family trips to Cape Cod, productivity and the stress before vacations, Michigan in the summer, and buying houses, Brian’s assistant. After catching up, we jump right into updates, price changes, dual-t...

  • What Is a “Launch”, Really? w/ Ben Orenstein

    With Jordan out of the studio, today our guest is Ben Orenstein. He is the host of the Art of Product podcast as well as Co-founder of the online tool, Tuple, which was built for remote pair programming on Macs (screenshare with audio). We talk about what...

  • Starvation or Indigestion?

    Two weeks in a row, and still plenty of topics and updates to discuss! Jordan wants to talk about how startups fail when they take on more opportunities than they can handle. If he decides to pursue any of the big opportunities that popped up recently, wh...

  • Navigating First Customers / Making a Big Price Change

    We are back from a lengthy hiatus and we have plenty to discuss for today’s episode! Brian updates our listeners about ProcessKit and what he is learning from the process. Jordan wants to discuss the price increases coming to Carthook. He also dives into...

  • Inviting First Customers / App Stores

    Hey, we’re back and we’ve got some lessons and updates to share with you! Both of us have plans to travel over the next few weeks. Jordan will be visiting his Slovenia team and Brian will be attending WP Elevation. Carthook and ProcessKit are both at a pi...

  • Inviting First Users & Profitable Team Growth

    We ask ourselves a lot of questions during this episode. Jordan is looking at Carthook and seeing exciting changes but now he has to consider what comes next. Brian is still getting ProcessKit ready for users and has to ask himself who should the first gr...

  • The “Strings” Attached to VC

    We have had some major decisions to make lately. Brian is working on ProcessKit and his self-imposed deadline is just around the corner. Now, he has to decide if he wants to launch a semi-ready product to his users. We discuss when is the appropriate time...

  • Selling to Teams & Hiring an Assistant

    Hey! We are back from MicroConf and we’ve got some great takeaways from the experience. We discuss the speakers and the talks and how the experience changes for us year to year. We also have some updates for you. Brian is still working on ProcessKit and i...

  • When Customer Support Does & Doesn’t Pay

    MicroConf is coming and we’re psyched! We take a glimpse at the schedule for this year’s event and we talk about what we’re looking forward too. Brian has an update on his pricing issue with ProcessKit and the conclusion he came too. Jordan is happy to an...

  • Pricing Per User or…?

    MicroConf is just around the corner and we are ready for it! We share our excitement about the conference and encourage you the listeners to say hi if you plan to attend this year. Brian has an update about ProcessKit and he actually has a launch date! He...

  • Hiring (or not?)

    We cover a subject that affects all bootstrappers today. Should you hire or not? This topic comes up because we both are looking to hire some new team members. Jordan has seven job openings and Brian is looking for a new writer for Audience Ops. We discus...

  • Who Is Selling the Product?

    MicroConf is right around the corner! We are excited and really looking forward to this year’s event.

  • Sales to Onboarding Process / Profitable Side Projects

    This week, Jordan has been very focused on sales. He and his company are considering hiring their first salespeople. Jordan shares he believes that they’ve gotten complacent and are starting to look at things in the wrong way – in aggregate instead of in...

  • Churn and Onboarding. Onboarding and Churn.

    Today we talk about something that affects all businesses, churn. No matter how successful your business is, everyone deals with customer churn. Jordan has decided to tackle Carthook’s churn problem head-on. He shares with Brian how he and his team have g...