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

  • 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...

  • Running a Black Friday Sale / Development Process

    2017 has been a phenomenal year for Jordan and Brian. On today’s episode, they give the audience an update on the businesses and offer a glimpse into their plans for 2018. Brian is going to shift focus to Productize and relaunch a bigger and better produc...

  • “Fattening” Your Company and… Freemium?

    Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move...

  • First Customer Demos, Paid Marketing Funnels, Team Communication

    We have both reached a turning point in our marketing campaigns. Jordan has launched a new marketing funnel for Carthook’s Shopify tool. Brian has been running a new marketing campaign for Ops Calendar. We share how the campaigns are working for us and of...

  • Pricing Page Teardown, Employee Onboarding, Company Transparency

    Today on Bootstrapped Web Jordan and Brian discuss what’s going on in their individual businesses. Brian is setting up Ops Calendar and takes today’s episode as a chance to get Jordan’s feedback from the customer’s point of view. Listeners who are interes...

  • Catching up! Managing Runway, Marketing Assets & Team Growth

    Welcome back to Bootstrapped Web! We took a bit of hiatus this summer but we have some great updates and insights to share from our time away. Jordan has grown his team from 4 to 11 people. He shares how the change has impacted how they do business and wo...

  • SaaS Momentum, Servicing Demand, & Why Amazon Bought WholeFoods

    We cover a lot in this episode of Bootstrapped Web. We give our listeners an update on both companies’ progress and we discuss some exciting news in the startup world. Brian shares some of the goals he has for Audience Ops in the near future. Jordan has a...

  • A Formula for Individual Success Metrics + Building a Hiring Engine

    Happily, our client loads are increasing, but our staffs are starting to feel the increased workload. So, we need to hire more people to keep up. It’s a good problem to have. On today’s episode, we compare our staffing needs and discuss how we are trying...

  • KPI Dashboards, Hiring Sales vs. Customer Success, & Solo Founders

    Today Brian and Jordan discuss growth. In Jordan’s case he is dealing with sudden growth, and in Brian’s case, he is planning for growth. Both share how they are handling this wonderful problem. Jordan has been focused on getting Carthook’s marketing up a...

  • Customer Overwhelm, Hiring & Firing Teammates

    We are both hitting some major growth right now in our businesses, and that means a lot of excitement and a lot of restructuring. We talk about project managing, hiring the right people, and the efforts we are putting into our marketing and lead generatio...

  • YouTube Content, Creating Webinars, Team Retreats

    We are back discussing our businesses and the progress that we have been making. On the personal front Jordan is heading off to Europe and Slovenia to work and hit the beach. Brian has been getting healthier with the BulletProof diet. Brian has been recor...

  • Back from MicroConf! More Signups! Facebook Ads Funnels!

    We are back from MicroConf and on this episode we share our takeaways and also update the important things going on in our businesses. Jordan shares how Russ Henneberry’s MicroConf talk encouraged him to look at his business differently. After this episod...

  • Onboarding First SaaS Customers

    Today we discuss how our respective businesses have begun on-boarding customers to our new products. The Shopify checkout app is growing and Jordan and his team are learning what makes the app successful. Brian has begun on-boarding clients on to the Audi...