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 if we take some off the table?

    In today’s episode we’re talking about socializing with family friends and work during the pandemic, as well as the latest news and questions on our minds about the current status of tech and the world. PokerStars, weekly stand-ups, Facebook, and what reo...

  • Managing Customers & Managing Teams

    Welcome back! Brian and Jordan are back behind the mic. We’re talking about ProcessKit’s best month, and Brian’s excitement about moving forward and making progress. We’re also talking about Jordan’s experience with Carthook’s people coach and accidental...

  • Remotely Working on Working Remotely

    We’re back for another episode of Bootstrapped Web. This episode is all about our thoughts on quarantine hair, having our kids at home, and working from home challenges. We’re talking about how to make working-from-home better, happier, and more productiv...

  • Trailer: The Productize Podcast returns in 2020

    Brian shares a quick announcement for his other podcast, The Productize Podcast. That’s an interview show where Brian invites business owners who are scaling with systems, processes, and teams — Primarily those in productized services, but he also s...

  • Raising Our Game

    We’re back behind the mic and keeping the streak going during the quarantine. Today we’re updating each other on our energy levels on Day # Who-Knows-What of “quarantine life”, catching up on the latest news in our businesses, how we put pressure on ourse...

  • People and Process

    Most of us are hovering around week 5 of the quarantine. How are you holding up? Today we’re talking about the lack of barbers and salons, the state of the economy, trends in our businesses and what we’ve seen in the market, the latest news on Carta, and...

  • Scrambled

    This is four weeks in a row now. Quarantine life is conducive to podcasting. Coronavirus has put people into precarious positions right now. What should be on our priority lists? How do you handle traumatic or dramatic events during a global crisis like C...

  • Day by Day

    It turns out when we work from home and we’re under quarantine, we can upload pretty consistently. Welcome back to the podcast, everyone. Things are still weird out there with COVID-19 and we’re just trying to take things day-by-day. Everything is so unst...

  • Compartmentalizing

    Brian and Jordan here! Like most of the US, we’re settling into the second week of quarantine life. As time goes on, it feels like this whole thing is going to last even longer than we imagined. Today we’re talking about COVID-19 and how it has affected u...

  • What Now?

    Brian and Jordan are holed up in their houses, podcasting in the time of Corona. There were pre-Corona episodes, and now our first post-Corona episode. Having heard some of our colleagues’ podcasts, it is apparent when these episodes were recorded: pre-Co...

  • What is Marketing?

    Two weeks in a row! How much can happen in a week? We’re back behind the mic today and we’re talking all about marketing and company culture. We talk about how straight forward the eCommerce marketing pitch used to be and about word-of-mouth marketing and...

  • Viruses and Positioning

    Brian and Jordan are back and feeling a little better from last week. We’re touching on the coronavirus and how it pertains to the economy and how it affects our businesses and conferences in the near future. We’re also talking about the stories in our he...

  • Sales and Therapy

    We’re are both back after a couple weeks off the mic. Today we’re talking about therapy sessions, the amount of stress and pain in entrepreneurial careers, business trips, leaks and waiting times, solving puzzles, and sales. When is a good time to start r...

  • Culture & Onboarding

    Brian and Jordan are back for the third week in a row. We talk about their plans for the next couple of weeks (Slovania and BigSnowTinyConf). We also go through a few current and upcoming updates. We pose a few questions including, when you have a new pro...

  • Positioning and Profitability

    We’re back! We’re excited about some winter weather activities and all of our 2020 ideas. We talk about brainstorming, questions, nomenclature, tiny conferences, and profitability. Here are today’s conversation points: Looking back one last time on 2019 J...

  • Back At It

    Today we’re talking about getting back to work after the holiday “festivities”, the inability to unplug, slowing down in December, the themes that ran through 2019, and what our themes for 2020 will be. Here are today’s conversation points: What to do whe...

  • Marketing Plans for 2020

    Brian and Jordan are back! We talk about holiday plans, the work-from-home life and coworking spaces, seeing and working with other human beings, spending all of our money at Starbucks, and the latest in marketing techniques. We talk about our past market...

  • Marketing Loose Ends & Funding Gaps

    Jordan and Brian are back behind the mic before Thanksgiving. Jordan talks about how great it feels to be unnecessary (at work) and various B-to-B and B-to-C marketing techniques. Brian talks about kits, his “new trialers”, and Processkit updates. They al...

  • Post-Launch & Code Freezes

    Today we’re live and in a rush since Jordan has to take his kids to lunch on their off-day!  We talk about post-Halloween shenanigans, Brian’s 37th birthday (at least, he’s not 40), the stats and news from Process Kit’s launch, capturing the creative...

  • Product Brain vs Marketing Brain

    Brian and (a sick) Jordan are back talking about upcoming Halloween festivities, what they missed out on by missing MicroConf (in Croatia), their thoughts on SEO, product vs. marketing, new podcasting ideas, and the new ProcessKit website. Here are today’...

  • So Much for That Plan

    Jordan and Brian are back with updates (even if they’re not so great). Brain updates us on the developments (or lack thereof) with his developer and how communication issues have played a part in the lack of progress. He also talks about how to move forwa...

  • Continuous Adjustments

    Jordan and Brian are back in the studio. Today the main focus is on the continuous adjustments needed in the software industry. They also quickly cover the trend of SaaS companies doing conferences and community-based marketing. Jordan talks about how gre...

  • Never Enough MRR

    Jordan and Brian are back to a regular podcasting schedule. Brian spent the weekend at a retreat/mastermind group at Martha’s Vineyard. Meanwhile, Jordan was at the Striped Conference. After a quick update, Jordan and Brian talk about the latest episode o...

  • Rabbit Holes Within Rabbit Holes

    It’s September, which means we’re talking about the changing of the seasons: kids are back in school, we’re gearing up for Black Friday, updating websites, and checking our numbers. Brian talks about his email marketing, hiring developers, and changing we...

  • Move It up and Accelerate the Plan

    Jordan is back! We talk about what we’ve been up to: family trips to Cape Cod, productivity and the stress before vacations, Michigan in the summer, and buying houses, Brian’s assistant. After catching up, we jump right into updates, price changes, dual-t...