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

  • 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...

  • What Should We Talk About?

    We’re back in the studio with a very special agenda… in that we don’t have an agenda today. So we turned to Twitter to ask listeners and followers what topics they would be interested in hearing about. If you have a question or a comment you’d like us to...

  • Heyyy + People-ing, Building & Marketing

    We’re back and we have so much to talk about. First off, we’d like to dedicate this episode to Ian Landsman and his twitter account. “Hey” seems to have taken Twitter by storm. We’ll talk about how we feel about that, and, of course, we’ll update you on w...

  • SaaS Onboarding & Recruiting at Scale

    We’re back behind the mic today after a one-week hiatus. We had originally recorded an episode last week (which addressed current events) but decided not to publish it. Our hearts do go out to everyone in this time of chaos and uncertainty. This week, we’...

  • Navigating Stress & Distractions

    The world is in chaos but we’re still here. Today we’re talking about some of the trends and the future of podcasting after some big news with The Joe Rogan Experience. We’re also going over some updates with Carthook, ProcessKit, and Audience Ops. Here a...

  • 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...