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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.
 
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
 
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Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in ZipMessage – Jordan’s hiring an SDR – Learning from strategic decisions that went wrong – Product insights with vs without a product in market Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for …
 
Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in ZipMessage – Jordan’s hiring an SDR – Learning from strategic decisions that went wrong – Product insights with vs without a product in market Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for …
 
We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ecom becoming “a thing” – ChatGPT is firmly in Brian’s coding workflow Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.…
 
We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ecom becoming “a thing” – ChatGPT is firmly in Brian’s coding workflow Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.…
 
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking with us another year on Bootstrapped Web. “Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This Plugin Tweet This Talking Points: Viruses, holiday cards, and coming …
 
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking with us another year on Bootstrapped Web. “Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This Plugin Tweet This Talking Points: Viruses, holiday cards, and coming …
 
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “What can this do? How does th…
 
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “What can this do? How does th…
 
Our obligatory take on Twitter in the Elon era. Also: SEO, board meetings, and growth targets. What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “…
 
Our obligatory take on Twitter in the Elon era. Also: SEO, board meetings, and growth targets. What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “…
 
Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “The single, most important element was… record your demos.” – Jordan Powered By the Tweet…
 
Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “The single, most important element was… record your demos.” – Jordan Powered By the Tweet…
 
What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrapped company? Brian and Jordan asked for your questions and Twitter delivered. Today, they are answering Twitter’s questions about what tools they use, and who to hire, and when. If you have any questions,…
 
What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrapped company? Brian and Jordan asked for your questions and Twitter delivered. Today, they are answering Twitter’s questions about what tools they use, and who to hire, and when. If you have any questions,…
 
Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet? How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or industry right now, what business would you …
 
Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet? How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or industry right now, what business would you …
 
What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team? Today, Brian and Jordan are talking about their daily routines and how they plan their days around work, their personal life, ex…
 
What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team? Today, Brian and Jordan are talking about their daily routines and how they plan their days around work, their personal life, ex…
 
How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals? After a short but busy couple of weeks, Brian and Jordan are back to talk about updates in their businesses and their lives. Jordan is starting to settle into Chicago and has come up w…
 
How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals? After a short but busy couple of weeks, Brian and Jordan are back to talk about updates in their businesses and their lives. Jordan is starting to settle into Chicago and has come up w…
 
How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features? There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environments, changing energies, and changing up routines. Today, Brian and Jordan are talking about what…
 
How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features? There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environments, changing energies, and changing up routines. Today, Brian and Jordan are talking about what…
 
What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat? It’s the middle of the summer edition of Bootstrapped Web. Brian and Jordan are back behind the mic after surviving famil…
 
What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat? It’s the middle of the summer edition of Bootstrapped Web. Brian and Jordan are back behind the mic after surviving famil…
 
How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products? It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage. Jordan talks about his fundraising efforts. Brian talks about his customer research project and…
 
How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products? It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage. Jordan talks about his fundraising efforts. Brian talks about his customer research project and…
 
Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s first marketer) talked about their $200,000 loan from Stripe and how he plans on publicly talking…
 
Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s first marketer) talked about their $200,000 loan from Stripe and how he plans on publicly talking…
 
What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur? After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what details he can about the acquisition as well as the process and journey of the company. They also …
 
What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur? After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what details he can about the acquisition as well as the process and journey of the company. They also …
 
How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path? As Brian comes back from a vacation and conference (and before Jordan leaves for his own), we’re catching up on the latest updates on ZipMessage and Rally. We’r…
 
How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path? As Brian comes back from a vacation and conference (and before Jordan leaves for his own), we’re catching up on the latest updates on ZipMessage and Rally. We’r…
 
We have some big news to share before we go on a (much needed) two-week hiatus. Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s criticisms of Shopify. We also talk about the power of audio, networking through podcasting, and marke…
 
We have some big news to share before we go on a (much needed) two-week hiatus. Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s criticisms of Shopify. We also talk about the power of audio, networking through podcasting, and marke…
 
How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology? Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and tokenizing. Token-based economics is the future of SaaS. Web3 tech isn’t just in the future, it’s…
 
How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology? Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and tokenizing. Token-based economics is the future of SaaS. Web3 tech isn’t just in the future, it’s…
 
Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far future. In today’s unscripted and random episode, Brian and Jordan give us some great news in terms of business updates. They also talk about one of the bigger customer issues when it comes to running a S…
 
Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage. Today’s episode is filled with business updates, optimism, and great outlooks for 2022. Don’t forget to che…
 
Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage. Today’s episode is filled with business updates, optimism, and great outlooks for 2022. Don’t forget to che…
 
Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th Your comments and feedback on Product Hunt would go a long way today To kick off the new year, Brian and Jordan share their 2021 reflections and 2022 goals (or whatever you want to call these ramblings). From moving across the country to …
 
Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th Your comments and feedback on Product Hunt would go a long way today To kick off the new year, Brian and Jordan share their 2021 reflections and 2022 goals (or whatever you want to call these ramblings). From moving across the country to …
 
What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer mile…
 
What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer mile…
 
Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootstrapped Web. Jordan talks about his hangups and why his need for idea exploration is causing dif…
 
When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities? Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free plans, website redesigns, an…
 
When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities? Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free plans, website redesigns, an…
 
Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to lead a round? Meanwhile, Brian gives u…
 
Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to lead a round? Meanwhile, Brian gives u…
 
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