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, and preparing themselves for an influx of activity, there is a lot going on behind the scenes. Exciting things are happening but with excitement come da...
Dec 08, 2021•31 min•Transcript available on Metacast 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, and preparing themselves for an influx of activity, there is a lot going on behind the scenes. Exciting things are happening but with excitement come da...
Dec 08, 2021•31 min•Transcript available on Metacast 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 about Rally’s methodical blog posts , which will be released slowly over the next few months. Brian shares some of the new features on ZipMessage and hi...
Nov 09, 2021•38 min•Transcript available on Metacast 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 about Rally’s methodical blog posts , which will be released slowly over the next few months. Brian shares some of the new features on ZipMessage and hi...
Nov 09, 2021•38 min•Transcript available on Metacast 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 updates on ZipMessage including marketing projects (comparison/competitor pages), hiring designers for website redesigns, and falling behind on content...
Nov 09, 2021•49 min•Transcript available on Metacast 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 updates on ZipMessage including marketing projects (comparison/competitor pages), hiring designers for website redesigns, and falling behind on content...
Nov 09, 2021•49 min•Transcript available on Metacast 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 Fund (formerly Earnest Capital), which has been a month in the making. He talks about the different decisions and considerations to be made when exiting...
Oct 27, 2021•42 min•Transcript available on Metacast 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 Fund (formerly Earnest Capital), which has been a month in the making. He talks about the different decisions and considerations to be made when exiting...
Oct 27, 2021•42 min•Transcript available on Metacast 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 about pursuing an exit from your business or thinking about acquiring one, we hope you’ll find some of our real-world experience from this deal hel...
Sep 23, 2021•57 min•Transcript available on Metacast 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 about pursuing an exit from your business or thinking about acquiring one, we hope you’ll find some of our real-world experience from this deal hel...
Sep 23, 2021•57 min•Transcript available on Metacast 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 very professional podcasting process, Rally’s current markers and goals, and Brian’s exciting marketing ideas. If you have any questions, comments, o...
Aug 19, 2021•38 min•Transcript available on Metacast 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 very professional podcasting process, Rally’s current markers and goals, and Brian’s exciting marketing ideas. If you have any questions, comments, o...
Aug 19, 2021•38 min•Transcript available on Metacast 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, comments, or topic ideas for Bootstrapped Web, leave us a message here . “Growth as headcount as an acceptable growth metric. And the reason for that is i...
Aug 05, 2021•39 min•Transcript available on Metacast 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, comments, or topic ideas for Bootstrapped Web, leave us a message here . “Growth as headcount as an acceptable growth metric. And the reason for that is i...
Aug 05, 2021•39 min•Transcript available on Metacast 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, hiring funnels and hiring hurdles, getting feedback, and ways to get out of a funk. If you have any questions, comments, or topic ideas for Bootstrapped W...
Jun 24, 2021•45 min•Transcript available on Metacast 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, hiring funnels and hiring hurdles, getting feedback, and ways to get out of a funk. If you have any questions, comments, or topic ideas for Bootstrapped W...
Jun 24, 2021•45 min•Transcript available on Metacast 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 media creator and a technical marketer. Check out the job opening for media creator if you love to create content, are comfortable telling stories, a...
Jun 17, 2021•34 min•Transcript available on Metacast 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 media creator and a technical marketer. Check out the job opening for media creator if you love to create content, are comfortable telling stories, a...
Jun 17, 2021•34 min•Transcript available on Metacast 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 leading a large tech team or would you rather keep your team small and easily manageable? What are your thoughts on the importance of communication for team...
Jun 03, 2021•40 min•Transcript available on Metacast 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 leading a large tech team or would you rather keep your team small and easily manageable? What are your thoughts on the importance of communication for team...
Jun 03, 2021•40 min•Transcript available on Metacast 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 team and the stigma around hiring a team full of contractors. Are you a freelancer looking for a little work? Are you a marketing specialist? If you hav...
May 20, 2021•59 min•Transcript available on Metacast 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 team and the stigma around hiring a team full of contractors. Are you a freelancer looking for a little work? Are you a marketing specialist? If you hav...
May 20, 2021•59 min•Transcript available on Metacast 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 who are as excited about it as you are? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan ...
May 06, 2021•35 min•Transcript available on Metacast 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 who are as excited about it as you are? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan ...
May 06, 2021•35 min•Transcript available on Metacast 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 Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb . “We need to complement each other...
Apr 29, 2021•47 min•Transcript available on Metacast 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 Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb . “We need to complement each other...
Apr 29, 2021•47 min•Transcript available on Metacast 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, from exiting Baremetrics to starting his own company for modern financial planning & wealth management. How do you handle your professional persona? ...
Apr 15, 2021•42 min•Transcript available on Metacast 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, from exiting Baremetrics to starting his own company for modern financial planning & wealth management. How do you handle your professional persona? ...
Apr 15, 2021•42 min•Transcript available on Metacast 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 hours. They also go over some final thoughts about the holidays, and what they plan on doing on their vacation. [tweetthis]“What were all the things that ...
Dec 24, 2020•36 min•Transcript available on Metacast 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 hours. They also go over some final thoughts about the holidays, and what they plan on doing on their vacation. [tweetthis]“What were all the things that ...
Dec 24, 2020•35 min•Transcript available on Metacast 
