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

  • 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...

  • Launching a New Service in 5 Days & Hitting Your Product Stride

    We have some big news coming up the following weeks. Brian discussed his recent experience with Facebook ads and the pros and cons of marketing on the platform. Jordan shares his found  his new found security in his business. We are really excited about t...

  • Updates Facebook Ads, Public Speaking, & Entrepreneurial Parenting

    Welcome back to Bootstrapped Web. On today’s episode we cover a lot of subjects that are both business and personal nature. We update you on Brian’s Calendar product and Jordan tells us about a talk he gave to his accelerator group. We also discuss Brian’...

  • Get-to-Launch Roadmap, Hiring (more) Developers, When to Work on Marketing

    We talk about Big Snow Tiny Conf and team growth today. Brian had a great time up at Vermont’s Big Snow Tiny Conf and has some awesome take-a-ways to share. Jordan is growing his team and is getting ready for a big marketing push. We both have some useful...

  • We’re back! Working Vacation, Too Much Transparency, & Product Updates

    Hello there! We are back at Bootstrapped Web after a month long hiatus. Brian spent some time overseas with his family. Jordan did the same state side. On today’s episode we talk about what is going on with our respective companies and how those developme...

  • 2016 Recap & 2017 Goals

    Well, 2016 is coming to an end. Today we’ll compare our goal lists from last year and reflect back on what went wrong  and what went right.   Carthook and Audience Ops have both grown and changed so let’s sit down and take a look at our 2016 results. We w...

  • Updates: Redesign, Marketing Multiple Products, & Selling Services

    Today’s Bootstrapped Web is going  to be an up-date episode. We both have a lot to talk  about with what we’re working at the moment. Audience Ops and Carthook have new products and we discuss what is working for our sales respectively. We talk about tran...

  • Family & Entrepreneurship

    Hey we’ve got a party episode with Rob and Sherry Walling from the podcast ZenFounder. We are going to discuss how to balance life with kids and entrepreneurship. We explore the common problems with living  with kids and keeping a business going. We also...

  • Launching 2nd Products w/ Ruben Gamez

    Welcome back to Bootstrapped Web. Our guest today is Ruben Gamez, the founder of Bidsketch.com. We are talking to Ruben today because Bidsketch is getting ready to launch a new product. Since we both are launching new products we thought it would be good...

  • Updates: Validating a Consulting Offer / Self-Funding a New SaaS

    Today’s episode is an update episode. Jordan tells us about finding his customer base for the funnel tool. Brian discusses how he is working with his developers on a new training product he is planning. We discuss when to allow custom jobs and when to say...

  • Taking a Big Shot vs. Lots of Little Shots

    On today’s episode, we welcome Craig Hewitt and Justin Jackson to the podcast. Jordan is having some time away. On today’s episode Craig, Justin, and Brian all discuss how to build and keep a company on track. We discuss what drives us and what we’re work...

  • Managing a Development Process w Rob Walling

    We welcome Rob Walling from Drip to the podcast today. Today we discuss how to navigate and manage the development process of a SaaS product. We all share our experiences with the excitement and frustrations of working with developers. Launching a new pro...

  • Pricing Questions / SaaS vs. Service

    We’ve got a party episode today. We welcome Rob Williams of Workshop and Folyo. Allan Branch joins us later on in the episode when we discuss his time with Less Accounting. Today’s topic was primarily pricing. How to price effectively, why to price at a c...

  • To Copy or Compete (or Both?)

    We find ourselves discussing competition and when you should copy a competitor’s model and when you should innovate a model. Many people get excited about a category, but are soon discouraged when they see the competition.  On today’s episode we dis...

  • Adding Service to Software / Marketing Pre-MVP

    Today’s episode is basically a therapy session for us both. We lay out our current issues and talk each other though the options. Jordan is dealing with customers and their personal expectations for the products. Brian is looking for balance in his develo...

  • Updates: Dev Process, MRR Milestones, Remote vs. Office

    Today is a basic update episode, but we have a special guest as well. Justin McGill is the co-founder of LeadFuze and co-host of the podcast Zero to Scale. He joins us on the update train today and gives us an idea of what the future holds for LeadFuze. J...

  • Going Global: Team Travel, Tiny Confs, & Remote Lifestyle

    We’re are having a “party” episode with some special guests today. We’ve got Dave Rodenbaugh, Craig Hewitt, and later on Brad Touesnard joining us. We are all involved with Big Snow Tiny Conf. Brian is head of the Vermont event, Dave is head of the West e...

  • Pre-selling and Planning to Build ‘Audience Ops Calendar’

    Today on Bootstrapped Web we talk about a new product from Audience Ops. Brian has developed a software product called Audience Ops Calendar. He has offered it to 12 clients and based his approach on a pre-sale model. During today’s episode Brian tell us...

  • Cofounders – w/ Rob Walling and Ben Fisher

    We welcome Rob Walling and Ben Fisher to the podcast today. We are going to discuss the topic of co-founders. Rob is the original founder of Drip, but has found a co-founder named Derek. Ben is Jordan’s co-founder in Carthook. Brian however is the solo fo...

  • New Products First Steps & Next Steps

    Well the launch for our new products are getting nearer. Today we give a general update on things and we talk about where we are on the new products. Brian is in the beginning of this process and Jordan is coming to the end of the process. Planning a new...

  • Pricing

    We welcome Ian Landsman back to the show to discuss the topic of deciding pricing. Pricing is an important tool for any founder. It can make or break your success. During today’s episode we talk about our pricing strategies and Ian tells us how he reached...

  • Planning vs. Execution

    On today’s episode we give an update on our businesses and how we move forward in our businesses. MicroConf. Is coming up over in Europe. Jordan will be leaving for the event soon and will be the first to speak. Today we talk about looking back on the yea...

  • Tools

    Today’s episode is about the various tools we use in our business and everyday lives. We will cover 9 areas of tools. Personal Tools Communication/Productivity Payments/Accounting/HR Customer Support Marketing Sales Production Design Podcasting Some of th...

  • The Bootstrapper’s Search For Meaning

    Today’s episode we give an update on our businesses and the on-going projects we have coming up. There is some travel on the horizon for Jordan and Brian both. Jordan is going for business and Brian for personal. Audience Ops has really honed in on sales...

  • Playing the Long Game

    We kick off our new format with Ian Landsman. Ian is the founder of Userscape and Helpspot. He has been working in the bootstrapped world since 2004. On today’s episode we discuss what it means to “play the long game.” We share our plans for Carthook and...

  • Growing The Product Line & Shifting Priorities

    Our episode today is just a basic update episode. A lot is going on in Audience Ops and Carthook and we are both just trying to keep up. We talk about the challenges we’re facing and how we plan to deal with them. Jordan is focusing more on the checkout p...

  • Questions on Pricing, Charging a Percentage, and Why Podcast?

    On today’s Bootstrapped Web we answer some listeners/readers questions. We also give you some updates on what’s going on in Carthook and AudienceOps. We discussed these topics today and answer these questions below: Updates on the personal front AudienceO...

  • [112] Do Entrepreneurs Get to Have Hobbies? And Other Updates…

    We have an update episode today. We start with the general updates about settling into a new house and keeping up with our newborn kids. We also touch on a subject that any entrepreneur can relate too, how your interests and hobbies get neglected when you...