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

  • 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...

  • Speaking Our Minds in 2019 / How Not to Increase Prices

    Welcome to 2019! This is our first episode of the year and we have a lot to say! Brian is planning a lot of travel these few months. That means that some of his projects are on the back burner. He gives an update on both ProcessKit and Sunrise KPI and exp...

  • More Questions Than Answers in 2019

    We are shying away from discussing goals or resolutions for the businesses this year. Instead, we reflect on how the bootstrapped world and business models have changed. A lot of approaches and marketing techniques have gone by the wayside in the last two...

  • Team Equity / A New App / The Next App

    The holidays are here! The office parties are going on and Christmas music is everywhere! Today Jordan is celebrating the growth of Carthook by offering his employees stock options. He discusses the stickiness of the decision and the excitement and nervou...

  • Surviving & Thriving Through Black Friday / Building an App in a Week

    With the year winding down we are feeling reflective during this episode of Bootstrapped Web. Jordan compares the state of Carthook from last year versus this year. A lot can change in a year! Brian is in a transition period right now and is currently try...

  • Launching a New Product in a Month / VIP Customer Sales

    We are gearing up for the holiday season here at Bootstrapped Web. Jordan has a serious talk about self-care and knowing when to step back. Brian gives an update on ProcessKit and announces a new product. Automation Guides is launching later this month. B...

  • Ben Orenstein Joins us to Talk Bootstrapping

    Ben Orenstein, is the co-host of The Art of Product podcast, a show where Brian recently appeared. Ben also tells us about his most recent project, Tuple, a tool for remote pair programming. We discuss where the idea for Tuple came from and the team who i...

  • Building in Public / Case Study Marketing / TinySeed

    We have some exciting updates to share and we give our reaction to Rob Walling and Einar Vollset’s big announcement of the TinySeed Fund. Jordan and his team are preparing to move offices in Slovenia. He also sings the praises of case studies. Carthook ha...

  • Bootstrapping Reality / Technical cofounders / New Management

    Today’s episode is a straightforward update episode for us. Brian is moving forward with ProcessKit and reflects on his goals for the project. Jordan celebrates the awesome team he has built over at Carthook and shares what it is like to step back and see...

  • ProcessKit Early Access / Celebrating Growth / CTO Questions

    We are back to tell you about some exciting news and developments. Jordan is enjoying a high mark in Carthook’s business and he found a building so he can move his Portland team. He also discusses the marketing strategies and changes that are making Carth...

  • Learning Rails vs. Laravel / Branding / Education Marketing

    Summer is in full swing and we are back from our individual vacations. We discuss our businesses and our personal roadmaps for Carthook and Audience Ops. We vent about developing frustrations and we do an armchair quarterbacking session for ConvertKit’s n...

  • Winning Time Back / (Not) Moving Offices / Learning to Code

    It is summertime! We have some great travel plans in the works, but before we pack our bags we want to celebrate the small victories we have seen in our businesses. Audience Ops podcasting is really starting to take off. Brian rehashes the road he took to...

  • Conference Hopping / Hiring Mistakes / Busting Growth Plateaus

    It has been three weeks of constant travel for us. We have been jetting around to tons of industry conferences. It has been a hectic and educational time for both of us. We share some of our takeaways from the conferences and really debate the value of a...

  • Value of a Coach / Hiring Spree / Launching in Public

    On today’s episode, we discuss the real value of a business coach. Jordan has announced that he would like to try his hand at it and Brian shares his own experience with it. We compare the pros and cons of being a coach for other founders and we explore w...

  • What If We Ran Your Business (For the Fun of It)?

    Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are sta...

  • The Carthook Team Talks Product Development Process

    We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service. Ben Fisher is the co-founder of Carthook and head of product. Rok Knez is Carthook’s lead...

  • Launching a Podcasting Service / Learning to Code / Partner Webinars

    MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working proper...

  • Charging For Attention / Elusive Product-Market-Fit

    It has been a crazy couple of weeks for both of us. We took a break last week, but we are back and we’ve got some great topics! Jordan spent all of last week fixing a product issue. It was hard, it was frustrating, and it showed him just how great his tea...

  • Conference Strategy, Webinar Funnels, & Lead Developers

    We are back to discuss the exciting and frustrating things going on with our businesses. Jordan has a lot on his plate including launching 15-20 new features and a few industry conferences; he will be attending the Traffic and Conversion Summit in San Die...

  • Sherry Walling Helps Us Keep Our Sh*t Together

    Our guest today is Sherry Walling. Sherry is a clinical psychologist and the author of the soon to be released book, The Entrepreneur’s Guide to Keeping Your S**t Together. Sherry is also the co-host of the Zen Founder podcast with her husband Rob W...

  • Holiday Hustle vs. Rest And Community Marketing

    Today we discuss a really heated topic that popped up on Twitter over the holiday break. A Twitter flame war was started by a post chastising business owners for not working through the holidays. We have some thoughts on the subject and we discuss the cha...

  • Our 2017 Review & 2018 Preview

    2017 is coming to a close and Jordan and Brian are looking back on this explosive year. They also share their plans for 2018. Audience Ops and Carthook both saw tremendous amounts of growth this year. That growth has caused the guys to reflect on 2017 and...