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

  • What We’d Build (If Not This)

    Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet?  How do you navigate the Catch-22 that is operations versus growth?...

  • Work-Life (Hour-by-Hour), Explained

    What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team? Today, Brian and Jordan are talki...

  • Research, Roadmaps, People, and Product

    How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals? After a short but busy couple of weeks, Brian and Jordan are back to talk about updates i...

  • Company as a Product

    How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features? There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environmen...

  • Product vs. Pipeline

    What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat? It’s the middle of the sum...

  • Talking to Customers

    How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products? It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage....

  • Marketing in 2022

    Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s fi...

  • CartHook Acquired!

    What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur? After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what det...

  • Traction… Then what?

    How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path?  As Brian comes back from a vacation and conference (and bef...

  • Everything Must Go

    We have some big news to share before we go on a (much needed) two-week hiatus.  Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s c...

  • Tokenizing

    How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology? Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and to...

  • So Meta

    Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far future.  In today’s unscripted and random episode, Brian and Jordan give us some great news in terms of...

  • Wheels Are Turning

    Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage.  Today’s epi...

  • 2021/2022 New Year reflections

    Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th 🚀 Your comments and feedback on Product Hunt would go a long way today 🙂 To kick off the new year, Brian and Jordan share their 2021 refl...

  • Define Traction

    What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updat...

  • The Chaos

    Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootst...

  • Chicken or Egg Development

    When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities? Brian and Jordan talk all about the newe...

  • How to Fund a Startup

    Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which fundi...

  • Go to Market vs. Marketing

    What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, cont...

  • Should We Rename the Podcast?

    Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses,...

  • Audience Ops Changes Hands

    Some news!  Brian has sold his business, Audience Ops, to JD Graffam!  And what better way to announce this transition than to bring JD on the show!   Jordan leads the way as Brian and JD talk through how this deal came toget...

  • Marketing ideas

    Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendou...

  • Back and Running

    After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “c...

  • Metrics & Hiring Funnels

    Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavor...

  • Hiring Media Creators

    Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bi...