Bootstrapped Web

On today's episode: When does shipping product lead to growth? Muddy Metrics Sports, exercise, health, eating, and drinking habits Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal

On today's episode: How we work with coaches & consultants to guide strategy & implementation UX hangover on shipped features Selling software "once" Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel

On today's episode: How we onboard and activate after a sales call Strategic pricing and show vs. don't show How to think about hiring a sales person Context switching between product work and marketing work as a solo founder. Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal

On today's episode: Building in public. Why and how? Learning sales. Process, strategy, tactics. How we learn and implement. A solo founder's dillemma Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel

On today's episode: How do we think about runway and profitability? What's an appropriate level of mud throwing? Should founders spend time on personal brand? Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Threads: @brian.casel Brian on Twitter: @casjam Jordan's company, Rally Jordan on Threads: @jordangal Jordan on Twitter: @jordangal

On today's episode: Brian's back from Asia (did he stop working?) Launching the Clarityflow app on iOS and Android (check the video) Jordan's shifting the sales process & sequence What it takes to close larger deals Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Yo! We're on Threads too!

On today's episode: The value of in-person relationship building The murky side of MRR growth Transparency with our teams PGA & LIV, Apple Vision Pro and other sidetracks! Connect with Brian and Jordan: Brian's company, Clarityflow Jordan's company, Rally Brian on Twitter: @casjam Jordan on Twitter: @jordangal

What (and when) is a SaaS "feature complete"? How do we sell and negotiate mid-market contracts? How to please customers (and which ones are worth pleasing)? ...And other tricky questions we're thinking about this week. Connect with Brian and Jordan: Brian's company, Clarityflow Jordan's company, Rally Brian on Twitter: @casjam Jordan on Twitter: @jordangal

Founder shadowing (make it a thing?) chatGPT vs. hiring a writer Go to market strategy Dialing in ICP What is marketing, really? Follow Brian and Jordan: Jordan's company, Rally Brian's company, Clarityflow Jordan on Twitter Brian on Twitter

Brian and Jordan give their takes on the question of whether to start up your first business earlier vs. later in life. Plus: Board meeting takeaways, MRR growth, sales demos, enterprise vs. mid-market, and BBQ smokers. Brian's business: Clarityflow (formerly ZipMessage ) Jordan's business: Rally Follow us on the Twitters: @jordangal & @casjam

What would we have done differently if we started Rally or Clarityflow over again? We get into that and other questions from Twitter. Keep em coming!Brian's business: Clarityflow (formerly ZipMessage) Jordan's business: Rally Follow us on the Twitters: @jordangal & @casjam

Brian's taming the chaos of inbound customer growth mixed with urgency to ship. Jordan's experimenting with 2 go-to-market strategies, one for enterprise, one with partners.Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage)

Jordan announces Rally's Series A and we unpack the whirlwind road that it took to get there. Brian launched a pricing increase, which coincided with a competitor's unexpected shut down. It's been a wild few weeks while we've been off, but we're back! Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage )

Random thoughts on what's happening in AI and startups. Jordan and co move to self-signups. Brian and co work on marketing projects. Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage)

Both Jordan and Brian are in the thick of redesigning their SaaS websites. Plus some tax talk. Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage) Learn about Section 174 tax issue for software businesses and join in the effort to repeal at ssballiance.org

Brian shares the news rebranding ZipMessage to a new name and the transition roadmap ahead... And the new name is...Jordan and team step away to a conference while go-to-market heats up.Oh yeah, and recorded on the day the Silicon Valley Bank saga unfolded in realtime... So that was a (and scary) discussion. Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage)

Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those hours. Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage)

Another week in the chaos that is startup land for Brian and Jordan. Topics include: Starting and finishing our day Managing focus through daily distractions Delegating strategy and teeing up for results And other rants… You know the drill Hit us on Twitter @casjam @jordangal with feedback on what we should talk about next week! Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

The episode streak continues! Brian’s product design process, Jordan’s annual budget meeting (and takeaways), outbound vs. inbound marketing, and an interesting discussion around the usefulness of projections. Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

This week, Brian and Jordan yap about: – Strategic partnerships – Pricing on transactions – Communicating company direction (internally) – Developer-focused content – …Creatine pills? We’re running out of ideas! Hit us up on Twitter (@casjam, @jordangal) and tell us what we should talk about. Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in ZipMessage – Jordan’s hiring an SDR – Learning from strategic decisions that went wrong – Product insights with vs without a product in market Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ecom becoming “a thing” – ChatGPT is firmly in Brian’s coding workflow Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking with us another year on Bootstrapped Web. “Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This PluginTweet This Talking Points: Viruses, holiday cards, and coming back from vacation 2022 for ZipMessage and Rally Lack of product-market fit Tim Ferriss’ Fear Setting The Ten-Year Business Staying “based” and staying true to your vision Themes and goals for 2023 Building features specifically for specific markets “The first year [for Zipmessage] was a dream and the second year was more bumpy and challenging.” – 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.

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.

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 tuning in. Head here to leave a review on iTunes.

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.

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 Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

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 iTunes.

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 Resources: Jordan’s response to Moiz’ Shopify Tweet Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

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 ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

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 iTunes.

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 Resources: Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

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 “The Cold Start Problem: How to Start and Scale Network Effects” by Andrew Chen Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer milestone. Today’s episode is all about the different ways you can build traction but also the different ways you can define traction. “If you can work directly with your audience to monetize the people who are crazy about you, you can make more money in a different model, and everyone is the most happy.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Marketing site changes at RallyGetting credit for speed and momentumNFT Projects for marketingZipMessage website updatesPersonalization for customers Creating a WordPress pluginPremium enrollment/Private or public conversationsPhases of Product/market FitWhat does traction feel like?Are customers willing to adapt for your product? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “We did things a certain way and, if they didn’t like that, either they didn’t become a customer or they adapted. And we had plenty of customers who adapted.” – 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.

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.