Bootstrapped Web

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 daunting tasks, important decisions, and possible mistakes. “What we’re about to do is, we’re about to scramble people’s priorities in a challenging way.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: New activity with ZipMessageOnboarding first merchants with RallyRemembering the excitement and joy that comes from sales demosExperimenting with a free plan on ZipMessageThe differences between the free and paid planRally’s all-hands to mentally prepare for a different challenge: new prioritiesZipMessage’s website redesignThe daunting task of revamping landing pages If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “Nothing like having real customers to really drive what’s really important.” – Brian 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.

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 his plans for ‘going to market.’ They also talk about how uncomfortable and rewarding the process can be. ‘Going to market’ is humbling and requires authenticity after all. “There’s a lot going on inside the company and inside the product. And ‘go to market’ is one element of that but you can’t just focus on that because there’s a lot of other things going on that we have to get right.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The difference between going to market and marketingWhat is involved when you go to marketMarketing techniques and content creatorsDifferent versions of networking If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “It’s this idea (especially in the first year) where you’ve got to be doing activities that are introducing the product to more and more new people.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  Rally ZipMessage As always, thanks for tuning in. Head here to leave a review on iTunes. 

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. “What we did was, we only worked with seed funds, because I wanted everyone to be focused on success at the seed stage.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Rally funding announcementsPlanning for funding and growth for RallyStrategic funding approaches and plansComparison/competitor pagesWebsite redesignsSEO content opportunities for ZipMessageHow to get the right response and the right person for the job If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “In this early stage, there is an element of creativity and strategy. I have to bring that knowledge to the project. I can’t just hand that off to someone else.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally Website As always, thanks for tuning in. Head here to leave a review on iTunes.

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 Audience Ops and taking funding for ZipMessage. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “I love this [angel funding] ecosystem and how it’s been evolving.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Jordan’s “coming out” strategy for RallyBrian takes funding from Calm Fund (formerly Earnest Capital) “I have been sitting on so many secrets, it’s not healthy. It’s not healthy to be quiet and fearful. It’s not my natural state.” – Jordan Powered By the Tweet This PluginTweet This Resources Rally Blog “Your Startup is a Movement” by David Sacks Calm Fund  Brian on Twitter Jordan on Twitter  ZipMessage As always, thanks for tuning in. Head here to leave a review on iTunes. 

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 helpful. You can read Brian’s blog post that dives deeper into the deal and thought processes that led up to the exit. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here Mentioned on today’s episode: Audience Ops JD Graffam on Twitter JD’s article, Fourteen Things That Will Keep Me from Buying Your App As always, thanks for tuning in. Head here to leave a review on iTunes. 

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, or topic ideas for Bootstrapped Web, leave us a message here “Something didn’t sit right. It wasn’t ambitious enough. We need to challenge ourselves more.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Forming a new corporation with ZipMessageThe need for full-service accounting/adminOur “professional” podcasting processListening back on episodes to help sharpen your gutRally’s current markersDo we have what we need to raise money?Working backwards from and mapping out the goal and markersHow to project numbers at this stageCreating a safe space to make mistakes, changing your mind, and getting appropriate push-back Marketing ideas and promotionThe Shipped Podcast (using ZipMessage)Testing audiences and different marketing platformsPodcast sponsorships: targeting small podcastsYouTube advertisingAlternative free trial program “Let’s not think of the worst case scenario but the realistic scenario.” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Office Engine Gusto Leave us a message here Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   As always, thanks for tuning in. Head here to leave a review on iTunes. 

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 if you’re not shooting for profitability and you’re shooting for milestones.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The relationship between founder and VCHeadcount versus profitability as growthHiring a recruiterZipMessage goalsPrioritizing requestsSetting up new featuresOpening it up to the publicThe Shipped podcastBrian’s new technical marketerIntroduction of technology to othersNiche toolsSummit, whiteboards that do math. The easiest way to create, test, and present your logic.Taming the chaos “If profitability isn’t the goal on this path (which makes sense), what are the metrics that you’re looking at for the next 12 months or 18 months?” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Leave us a message here Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   As always, thanks for tuning in. Head here to leave a review on iTunes. 

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 Web, leave us a message here.  “I saw a ZipMessage pop up in my Slack the other day. I love seeing it organically used because that’s the tool that fits.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Matt Medeiros and the media creator roleThe technical side of ZipMessageReading stats and getting feedbackGetting out of a funkCompleting tasks, self-induced stress, and forgivenessFiguring out the right workflow and the right peopleHiring funnels, hurdles, testimonials, and role-specific adjustments “People get value from it and they don’t tell you they’re getting value from it. It’s just happening and you don’t see it right in front of you. You have to see the stats.” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Matt Medeiros’ Twitter Thread on the media creator role ChartMogul DynamiteJobs Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   Brian’s 2 positions open for applications: Media Creator Technical Marketer Leave us a message here As always, thanks for tuning in. Head here to leave a review on iTunes. 

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, and coming up with creative new ideas. He is also looking for a technical marketer who will work on distribution and optimizing channels and SaaS funnels. If you are interested in either job position, use the links below to apply. Media Creator   Technical Marketer If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message here “You want the authentic version of the media and the audience and value, and then allowing for a bridge from there, over to the product.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: ZipMessage Updates:Growth and skepticism Job openings:Media creatorTechnical marketerCreating a communityThe Bloomberg ModelAxiosConversations and conveying the Rally messageWhat to lead withHow to make your message resonateShopify opinionsBrian is hiring for 2 roles: Media Creator   Technical Marketer “If you want an engaged community where they interact with each other, the audience has to come first.” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Axios Today Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   Leave us a message here As always, thanks for tuning in. Head here to leave a review on iTunes. 

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 teams who work remotely? If you have any questions, comments, or topic ideas for Brian or Jordan, leave a message here. “When you start to talk about a bunch of people, all in coordination, all in different time zones, all on different things, that stuff is just magic to me.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The next step for RallyThe many uses for ZipMessageCombining live Zoom calls with asynchronous follow-upsDirect Slack integrationsThe ZipMessage roadmapLeading a tech teamRequirements for leadershipThe importance of communicationDifferent strategies for marketing “The way that I think about integrations generally is, it’s more about, ‘Does it solve a customer problem and customer conversion?’” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Patrick Campbell’s tweet about building a media brand, monetizing with software Unthinkable podcast by Jay Acunzo Our stuff: Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook Leave us a message here