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

  • 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...

  • Raising The Bar

    Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it...

  • Rally On

    It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also g...

  • Bugs vs. Customers

    Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch...

  • Staying positive

    Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typic...

  • Never Fast Enough

    Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and co...

  • Know Thyself

    Will this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’...

  • How is it different?

    This is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for bo...

  • Bootstrapped to VC

    Officially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year. On the business front, things are...

  • Launching from no man’s land

    Today, Brian and Jordan are talking about what it’s like in no man’s land and their struggles with imposter’s syndrome. Brian shares more details about his newest venture. Jordan talks about his need for structure. They do a deep dive into the launch proc...

  • Who is the customer for this SaaS?

    Brian and Jordan are back after a short break. Today’s topics involve new developments with Brian, Twitter conversations, and market research for new and current projects. Brian gives us a sneak peak into a new project. Jordan brings his opinions on Twitt...

  • New year, new directions

    Brian and Jordan are back after a bit of a hiatus. Today they’re trying a different format change as each takes center stage for half of the show so they can better update everyone on their progress since the new year started. And what a new year it’s bee...

  • Let’s Be Less Wrong in 2021

    Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks abou...

  • All the Things

    Vote for us on the SaaS Podcast Awards! Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about J...

  • Satisfying Customers

    On this episode of Bootstrapped Web (dubbed the “anything but election talk” episode), Jordan and Brian go over Carthook’s exciting launch in the Shopify App Store and ProcessKit’s visual upgrade. Brian also has a couple of aces up his sleeve when it come...

  • Calm Before the Storm

    Jordan and Brian are back after a few weeks. It is election week; that means a lot of stress and a lot of chaos. But before that stuff hits the fan, Jordan is launching a new Carthook product inside the Shopify app store and Brian has been redesigning the...

  • Good morning

    Today Brian and Jordan are talking about deadlines, Black Friday, and a little bit of introspection. They go over their love/hate relationship with mornings. They also take a deep dive into hopes, dreams, dedication, and hiring true believers. Here are to...

  • Talkin shop with Ian Landsman

    On today’s episode of Bootstrapped Web, Brian and Jordan are joined by Ian Landsman from HelpSpot. Ian has made product after product over the years, from UserScape to HelpSpot to LaravelJobs and Thermostatio. You can find him on Twitter or you can learn...

  • Company Design

    We’re in a great mood on today here atf Bootstrapped Web. We’re talking about drive-in movies, apple picking, AirBnB’s, Twitter, and business updates. This episode is a bit of a topic potpourri is as we cover new features, hiring and interview processes,...

  • Should You Audience?

    Brian and Jordan are back behind the (brand new) mics. They’re reminiscing about the beginning of the podcast, the fires in the west coast, and catching up on the latest news in the industry as well as their businesses. Here are today’s conversation point...

  • The Next Chapter in the Product

    It’s been a little while but Brian and Jordan are back behind the mics. On today’s episode, they’re talking about vacations, a long first week back, marketing, big news with Carthook, cold emails, and guest features. Here are today’s conversation points:...

  • Chicken or Egg or Fundraise

    We’re back with “Boo-strapped Web”. We’re behind the mic talking about stress, marketing, executing decisions, and guilt over new hire experiences. Lastly, we’re going over the latest news in startup financing, which could blow everything out of the water...

  • Hello Competitors

    Today we’re talking about camping ratios, COVID and Black Friday, the eCommerce boom due to COVID, emotions versus moods, Twitter, and competitors. We go over some bold and unique marketing strategies with ProcessKit, how we’ve won Jordan over in the “Wor...

  • What does VC really mean? And marketing.

    We’re back after a two-week break. More specifically, a camping and Niagra Falls break. Today we go over two kinds of VC: vacations and venture capital. Not to mention, we go over ProcessKit’s newest marketing news, Ali Mese’s article on Medium, and our t...