Bootstrapped Web | For Entrepreneurs Bootstrapping Web Startups | Interviews & Business Case Studies

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 … Continue reading Marketing in 2022

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’re also talking about how to best judge our own traction, and how to decide which feature to work on first. “All the best paying customers are usually pretty quiet. ” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Staying unplugged during a vacationRecognizing milestones and gauging progress Updates on ZipMessage and RallyDealing with big competitors head-onFuture plansBeing a SaaS business owner and a SaaS customerIntegration partnerships: the approaches, the benefits, and the selection processDeciding how to move forward: short term decisions versus long term/strategic decisions If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I highly recommend working with a lawyer that you both trust and like, because there’s some moments out there…” – Jordan Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on

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 marketing. “The relationship built through audio is so much more powerful. It’s really hard to do that with copywriting, with a website, with ads. It’s just much harder to do.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Taking a break and staying away from the computer while on vacationMoiz Ali’s tweet about Shopify’s problemsThe problems that they need to solveMarketing and speaking your mindThe sale of the Productize brand (and everything else)Networking through podcasting Connecting with people through audioCompetitors and marketing If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “I would focus on one thing at a time, but (in my experience) it’s not the end of the world to have a few different things going and learn and hone different types of chops and skillsets and meet different people.” – Brian Powered By the Tweet This PluginTweet This

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 … Continue reading CartHook Acquired!

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 talk about the upcoming MicroConf and what conferences can do for you. After all, they’re not just about networking, there are a lot of things gained when meeting with colleagues, competitors …and podcast listeners. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “The thing that I want out of a conference is a huge boost of confidence.” – Jordan Powered By the Tweet This PluginTweet This Talking Points: Carthook officially acquiredShutting down and selling the supported Shopify appA mixture of emotions after a crazy journeyUnwinding after the stress of a tripWhat conferences can do to your mindsetThe energizing effect of conferencesMeeting podcast listenersHow it feels to be an anonymous company in a space with huge companiesCompetitors on Twitter: To Mute or Not To MuteHow many people do you need for a startup?Access the gratitude “Since Day 1, we’ve had a fundamental difference of what ZipMessage is and that’s the intake ability.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter

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 … Continue reading Traction… Then what?

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, … Continue reading Everything Must Go

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 happening right now. “I would aim for zero commercial partnership: no rev share either way. Those are the best partnerships.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Dealing with bad days, finding additional sources of joyBig Snow Tiny Conf (East)Marketing: calming down after product launch and initial promotionIntegrations and examples ofWriting and promotionFundraising and tokenizingAdopting web3 technologyTransitioning between developers during “The Great Resignation” If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I’m so excited to be a part of this podcast now. I feel like I get a front row seat and I’m slowly starting to see how Web3 actually starts to change things.” – Brian Powered By the Tweet This PluginTweet This Resources: Big Snow Tiny Conf Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on

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 happening right … Continue reading Tokenizing

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 SaaS company. Not to mention, a deep dive into the metaverse: what does the future look like with Web3? “What shoe will need to drop in order for Web3 solutions or applications or products or services or platforms to spill over into the wider market?” – Brian Casel Powered By the Tweet This PluginTweet This Here are today’s conversation points: That wonderful feeling when things are starting, building, and rollingHow to keep the momentum goingSaaS issues: the discomfort of having most of your market be anonymous to youForeshadowing of why we should take the metaverse seriouslyWill Web3 be corporate-owned or user-owned?Monetization through advertising and other types of modelsTinyConf, Disney, and other events in the near future If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “No one is going to get to zero. But you do need to remain underneath the line of ‘too frustrating.’ And that line has not been determined yet.” – Jordan Gal Powered By the Tweet This PluginTweet This

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 … Continue reading So Meta

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 check out ZipMessage on … Continue reading Wheels Are Turning

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 check out ZipMessage on ProductHunt! “I prioritize [the reliability of recording and playback] over shipping a brand new feature.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: The sale of ProcessKitChicago, look out for JordanZipMessage on Product HuntIs Rally ready to go to market?Marketing funnels and sales funnelsPrioritization at ZipMessageZIpMessage conversion emails If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “What helps me is knowing what the journey looks like.” – Jordan Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th

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 difficulties with his leadership team. Meanwhile, Brian is continuing to navigate the challenges of starting a new business with a niche target market. Is podcasting the answer? They also go over some interesting tools for searching for the perfect podcast, marketing to specific groups, as well as their excitement for Andrew Chen’s newest book, “The Cold Start Problem.” “I’m very much a middle sibling when it comes to management at the leadership level. It’s very collaborative.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: A new ZipMessage websiteHiring generalists or specialistsChallenging leadership team conversationsMarketing and and outreach for the podcasting communityInfluencer outreachSEO plays and search demandsAndrew Chen’s newest book release If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I’m getting these things dialed in. It’s difficult but I think it’s finally starting to come together.” – Brian Powered By the Tweet This PluginTweet This Resources: SparkToro Podseeker