Bootstrapped Web

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 this change our product? Does this change things significantly enough that we should come off our roadmap?” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The future of AI and creators Q4 spreadsheets and budgeting Updates in Rally and ZipMessage SEO content Marketing and sales Product-led content “If we’re not working on those growth graphs, I don’t feel comfortable. But, at the same time, I need to work more on the product” – 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. 

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 “The more Twitter is in everyone’s everyday lives, the more leverage Twitter and Elon have to start taking marketshare in these parts of life.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: The conclusion of Jordan’s moving sagaThe new era of TwitterVerificationTwitter as a productBuilding in publicTeam retreats and all-hands meetingsZipMessage updatesSEO: quantity, speed, and AI toolsBoard meetings and keeping recordsGrowth Targets “I would love to build a culture where anyone in the company can say, ‘I think we’re focusing on this thing when we shouldn’t’ or ‘I think we’re missing this entirely.’” – 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. 

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 This PluginTweet This Here are today’s conversation points: NoSnowTinyConf RecapResidual issues that arise after raising fundsRally updatesLaunch of Coach Club and Coach Club DigestTreating marketing as a productTeam updates, accountability, and weekly stand-ups “[I love] approaching marketing like its a product in itself.” – Brian Powered By the Tweet This PluginTweet This Resources: Coach Club Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes. 

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, comments, or topic ideas for Bootstrapped Web, leave us a message here. “It’s interesting the way we think of tools and how we sell tools to other companies.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation Points:  NoSnow TinyConfTools that we use: Techstack (Laravel, Angular, React, Ruby on Rails, PHP, Tailwind)Project Management (Github, Notion, MixPanel, Confluence, Jira)Marketing Changelog Sales, Marketing, and Support (Pipedrive, Asana, Hubspot, Salesforce, Intercom, Customer.io, HelpSpace, HelpScout)Metrics and Internal Tracking (Grafana, Profitwell, ChartMogul, MixPanel, Amplitude, Google Analytics, Fathom Analytics, Plausible Analytics)Communication (Slack) Hiring when you’re bootstrapped, versus when you’re fundedWho to hire firstWho they are hiring now “If you can market and get your tool into their hands sometime during that first year of the company, you have such a higher likelihood of getting in. Some of these tools are so sticky.” – 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. 

In this episode, Brian and Jordan discuss the challenges of operations vs growth in various types of businesses. They also explore the potential of AI-driven technology, building a company for media businesses, and opportunities in the food and music industries. Additionally, they emphasize the importance of being authentic online and engaging in meaningful conversations.

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, exercise, and with team members that are scattered all around the globe. They share different time-saving tricks, apps that help hold them accountable to staying healthy, and their opinions on morning productivity and pulling all-nighters. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I have some real issues with the morning. I’m not very productive in the morning.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation Points:  Rocks, pebbles, and boulders (and hair and sand)Daily routines and how to optimize your dayPersonal lifeProfessional lifeMorning productivity versus night owl hoursThe ultimate productivity app: a notepad and a penProductivity hours when your team members live in different time zonesSeparating professional and personal life “I”m very much a morning person. I like waking up relatively early but these people with the 5AM and 4AM wake-ups seem just a little bit extreme to me.” – 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. 

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 with some interesting revelations. Meanwhile, Brian has also come up with some interesting revelations after listening to and analyzing customer feedback. This has all resulted in a surprising new waypoint on their roadmap. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “That’s the thing that keeps me unemployable, really, is that I own my own business and what I’m building here is an asset that will result in a much bigger win down the road.” – Brian Powered By the Tweet This PluginTweet This Talking Points:  Jordan’s big move to ChicagoHappiness in comparison to other people and the struggles of finding your own pathThe next iteration of ZipMessageCoaching Building more features and adapting what we haveHiring, resignations, building up teams and the organizationNoCode consultants and solutions businesses “The environment has a big impact on the conversation that I’m having in my head about ambition, money, business, and that soup.” – 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. 

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 they do to stay productive, how their teams are forming and evolving, and what sales in 2022 looks like. What else should we talk about? What are you hearing (or not hearing from us) that you’d like to know about? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “The economy is going to do what it’s going to do. There’s not much we can do about that except work on the things we can control.” – Brian Powered By the Tweet This PluginTweet This Talking Points:  Productivity during tumultuous/chaotic personal livesTreating your company like a productUpdates with ZipMessageCreating a culture for a teamReplacing SEO Asynchronous updates Building our own communityAnnouncing featuresRally updatesBuilding company culture when you feel too absentSaaS sales in 2022Building teams and laying out playbooks “The market shifted but it didn’t implode. It’s not like everything is over. Everything feels a little more serious right now.” – 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. 

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 family vacations, COVID, and cancelled flights. Today, Brian dives deep into repositioning and how ZipMessage has refocused in the past couple weeks. Meanwhile, Jordan talks about the biggest mistake he has made with Rally so far. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “It went from, everyone’s growing and there’s plenty of money to fund what you want to do to, all of a sudden, the water went back out and it turns out a lot of people don’t have pants on.” – Jordan Powered By the Tweet This PluginTweet This Talking Points:  ZipMessage and Rally updatesThe changes in the venture funding and the bootstrapped entrepreneur worldRepositioning and refocusing at ZipMessageDifferent pipelines: influencers, coaches, consultants, etc.Building CRMs (Airtable, Pipedrive)Learning from mistakesBeing led by productHow Jordan built a stronger working relationship with his teamLearning from an existential crisisThe truth behind SaaS companies “It doesn’t make sense to focus on product unless we have a daily pipeline that is ready to present that product too.” – 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. 

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 what he has learned through that process.  If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “It went from, ‘This is going to be a piece of cake’ to… ‘That’s not what’s going on in the market.’” – Jordan Powered By the Tweet This PluginTweet This Talking Points: Trends in the industry and the economyCan you avoid consistent churn numbers in new products?Jordan’s fundraising effortsInvestor behaviorsAre people driven by FOMOThe various stages in the funnelBrian’s research project The lessons that Brian learnedWhat motivates customers and what makes them think?Shifting product features based on the marketLearning from other competitors and their customers “When you actually talk to [a customer], you not only learn a ton, it also helps me emotionally and mentally” – Brian Powered By the Tweet This PluginTweet This Resources: Brian’s Twitter thread documenting his customer research project Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.