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Bootstrapped Web is for entrepreneurs bootstrapping their startups, who believe that the best way to get to where we're going is to learn by doing. Conversations, case studies, and interviews with entrepreneurs who are building profitable businesses online. Let's do this.
 
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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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…
 
What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and ZipMessage. Jordan talks ab…
 
What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and ZipMessage. Jordan talks ab…
 
Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market. Brian takes funding from Calm Fun…
 
Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market. Brian takes funding from Calm Fun…
 
Some news! Brian has sold his business, Audience Ops, to JD Graffam! And what better way to announce this transition than to bring JD on the show! Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now underway. If you’re thinking…
 
Some news! Brian has sold his business, Audience Ops, to JD Graffam! And what better way to announce this transition than to bring JD on the show! Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now underway. If you’re thinking…
 
Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, their…
 
Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, their…
 
After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community. If you have any questions, comm…
 
After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community. If you have any questions, comm…
 
Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavors. They talk about the progress on the search for a media creator for both Rally and ZipMessage, hiri…
 
Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavors. They talk about the progress on the search for a media creator for both Rally and ZipMessage, hiri…
 
Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bit of everything today. Brian shares a couple of interesting job openings based on ZipMessage: a…
 
Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bit of everything today. Brian shares a couple of interesting job openings based on ZipMessage: a…
 
Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it is marketed and sold. What are your thoughts on SaaS marketing strategies? Do you prefer leadin…
 
Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it is marketed and sold. What are your thoughts on SaaS marketing strategies? Do you prefer leadin…
 
It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks about the possibility of building a small te…
 
It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks about the possibility of building a small te…
 
Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if this new project is worth it? How do you find people w…
 
Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if this new project is worth it? How do you find people w…
 
Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas for Bootstrapp…
 
Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas for Bootstrapp…
 
Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, fro…
 
Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, fro…
 
Will this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’s secret project? They also talk indepth about discipline and productivity. Do working sessions…
 
Will this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’s secret project? They also talk indepth about discipline and productivity. Do working sessions…
 
This is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for both Brian and Jordan when it comes to business news. They also successfully avoid having Jordan …
 
This is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for both Brian and Jordan when it comes to business news. They also successfully avoid having Jordan …
 
Officially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year. On the business front, things are moving (slow and steady) for Brian. ProcessKit has accumulated a decent amount of data which m…
 
Officially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year. On the business front, things are moving (slow and steady) for Brian. ProcessKit has accumulated a decent amount of data which m…
 
Today, Brian and Jordan are talking about what it’s like in no man’s land and their struggles with imposter’s syndrome. Brian shares more details about his newest venture. Jordan talks about his need for structure. They do a deep dive into the launch process and various launch strategies as well as updates on their various projects, their opinions …
 
Today, Brian and Jordan are talking about what it’s like in no man’s land and their struggles with imposter’s syndrome. Brian shares more details about his newest venture. Jordan talks about his need for structure. They do a deep dive into the launch process and various launch strategies as well as updates on their various projects, their opinions …
 
Brian and Jordan are back after a short break. Today’s topics involve new developments with Brian, Twitter conversations, and market research for new and current projects. Brian gives us a sneak peak into a new project. Jordan brings his opinions on Twitter and how companies are using their social media profiles for marketing. They briefly talk abo…
 
Brian and Jordan are back after a short break. Today’s topics involve new developments with Brian, Twitter conversations, and market research for new and current projects. Brian gives us a sneak peak into a new project. Jordan brings his opinions on Twitter and how companies are using their social media profiles for marketing. They briefly talk abo…
 
Brian and Jordan are back after a bit of a hiatus. Today they’re trying a different format change as each takes center stage for half of the show so they can better update everyone on their progress since the new year started. And what a new year it’s been so far: finishing off some old chapters and starting new ones, and the journey in between. “M…
 
Brian and Jordan are back after a bit of a hiatus. Today they’re trying a different format change as each takes center stage for half of the show so they can better update everyone on their progress since the new year started. And what a new year it’s been so far: finishing off some old chapters and starting new ones, and the journey in between. “M…
 
Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks about a couple podcasts he was a part of, fun holiday parties, and minimizing risks of wasting hour…
 
Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks about a couple podcasts he was a part of, fun holiday parties, and minimizing risks of wasting hour…
 
Vote for us on the SaaS Podcast Awards! Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about Jordan’s experience working with Shopify, Brian’s 2021 goals for consistency, as well as a surpr…
 
Vote for us on the SaaS Podcast Awards! Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about Jordan’s experience working with Shopify, Brian’s 2021 goals for consistency, as well as a surpr…
 
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