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

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 … Continue reading Tools & People

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

Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet?  How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or … Continue reading What We’d Build (If Not This)

Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet?  How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or industry right now, what business would you start? Brian and Jordan are answering some of your questions and topics submitted through Twitter.  If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “Every business that I’ve ever had, has been a reaction to the previous business.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation Points:  Operations versus growth In SaaS versus as a freelancerWhat you need to do in order to not interrupt the forward momentumInvite-only feature launch with ZipMessageDoes funding really help extend your roadmap?The Catch-22 of growth and operationsNew and different niches and industriesTime away for researchAI-driven techMedia businesses in the modern webYouTube, TikTok, OnlyFans, etc.Different use cases for almost anythingSeparating passion from a career?The formatting of new podcastsTypes of tweets and content on Twitter “Having millions of dollars in the bank doesn’t help.” – Jordan Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tunin

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

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 … Continue reading Work-Life (Hour-by-Hour), Explained

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 … Continue reading Research, Roadmaps, People, and Product

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

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 … Continue reading Company as a Product

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:

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 … Continue reading Product vs. Pipeline

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 Plugin

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 … Continue reading Talking to Customers

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

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 on publicly talking about how they will be spending that money. Brian and Jordan give their take on Aaron’s content marketing technique. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “You can make it happen, but not really. Your customers make it happen.” – Jordan Powered By the Tweet This PluginTweet This Talking Points: The timeline for Jordan’s big moveWhat’s it like to sell and buy a house in this marketZipMessage updatesChanges on the websiteSurveys after signing upCoining “ZM”Perfect uses for ZipMessageHiring strategists for SEO researchTraction with RallyConversations with investorsThe importance of honesty and “when” to be honestLooking for marketersTuple’s marketing campaign Aaron Francis as Tuple’s first marketerAaron’s tweet about their $200,000 loan from Stripe “When a customer explains the whole value prop, it gives me so much more energy.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage