Bootstrapped Web

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

It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks about the possibility of building a small team and the stigma around hiring a team full of contractors. Are you a freelancer looking for a little work? Are you a marketing specialist? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I’m in the middle of that thing that happens if you post a Twitter thread just at the right time. It’s fun. You have to remember to enjoy the fun days. This is one of those fun days.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Rally and RallyOn.comWhat does Rally do for customers?What does it mean to go headless?Definition of “Modern brands”What makes Rally different?Enjoying and being in the momentThe importance of elevator pitches and headlinesMultiple fits and building relationshipsThe next step and roadmap for RallyZipMessage updatesDoing everything yourself vs. building a small teamContractors and freelancers vs. employeesThe stigma behind hiring overseas Creating your perfect company culture Brian’s marketing talent wishlist:Technical marketer (Google analytics, SEO, etc.) Media producer (podcasting, interviews, etc.) “I’m already all in in terms of hours. But to really go all in, I need a team with me.” – Brian Powered By the Tweet This PluginTweet This Resources: Leave us a message here Rally On Josh Pigford’s Maybe company compensation model Sahil Lavingia on Gumroad’s team model 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 behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if this new project is worth it? How do you find people who are as excited about it as you are? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb. “I’m slowed down by the product and the bug-fixes.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Project and business updates: marketing, development, and not moving fast enoughTalking with partners and agencies versus potential customersTaking a position and what that means for a businessHow to decide whether a project or a product is worth the time?The Catch-22 of starting and growing a new businessHow to evaluate a “head-of-growth” expertPivotal moments in ZipMessage and secret projectsGrowth hacks for ZipMessage “My favorite thing (the thing that I’m good at) is articulating that future vision clearly.” – Jordan Powered By the Tweet This PluginTweet This Resources: 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 with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb. “We need to complement each other more. Because everyone asks for feedback, nobody asks for compliments.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Updates on Jordan’s secret productFeeling down and (surprising) external motivatorsWhat founders do and the meaning of being a founderThe importance of compliments and empathyUpdates, changes, and uses for ZipMessageFramework and patterns in successful niche SaaS productsThree-phase process: enter, lean-in, all-in “For founders, literally all we do is solve problems. What’s the next problem to solve? What’s the next thing that’s not working? Every single day.” – Brian Powered By the Tweet This PluginTweet This Resources ZipMessage New! zipmessage.com/bootstrappedweb Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, from exiting Baremetrics to starting his own company for modern financial planning & wealth management. How do you handle your professional persona? Are you an open book on your social media accounts? Are you strategic about what you post? Brian and Jordan discuss Josh’s strategic and surprisingly open discussions on Twitter and how they differ in their social media personas. “I did want to step in and reiterate some of my larger goals and priorities to the team on Audience Ops, about what makes Audience Ops great. Kat really did that well, but I want to make sure that the team really knows, ‘This is why things work so well here. Let’s keep this going.’” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: The roller coaster of ZipMessage onboardingFinalizing copy and launching landing pagesAudience Ops team changes and transitionsThe vision at Audience OpsExpectations, emotions, and performative reactions during Monday morning callsThe importance of understanding the “Why”Josh Pigford’s exit from Baremetrics and his professional trajectory…in publicAngel investing and asking for money “If you have an audience and you want to start a company, at this point, you can just ask for money. You can legally, publicly ask for money.” – Jordan Powered By the Tweet This PluginTweet This Resources Maybe.co Josh Pigford’s Twitter ZipMessage SunriseKPI Productize AudienceOps ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks about a couple podcasts he was a part of, fun holiday parties, and minimizing risks of wasting hours. They also go over some final thoughts about the holidays, and what they plan on doing on their vacation. [tweetthis]“What were all the things that I was wrong about? In the last year?” - Brian [/tweetthis] Here are today’s conversation points: Taking a break and the importance of stepping awayWhat is burnout?Macro versus micro expectations for ourselvesPodcasts that Jordan has been a part of lately (Greylock, Better Done Than Perfect)Looking back on 2020What happens in ‘21?ProcessKit updates: onboarding flow, new home pages, etc.Holiday parties (and possibly monthly happy hours) using GatherTownThe process for validating products [tweetthis]“I don’t do that many hours of intense work and writing and that sort of thing, but it is the constant thinking and worrying.” - Jordan [/tweetthis] Resources: Greylock (Greymatter): “Mike Duboe | The Rise of Headless Commerce” Better Done Than Perfect: Radical Onboarding Experiments with Jordan Gal Better Done Than Perfect: Launch Lessons & Product Surveys with Rand Fishkin Gather.town SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Vote for us on the SaaS Podcast Awards! Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about Jordan’s experience working with Shopify, Brian’s 2021 goals for consistency, as well as a surprise nomination, onboarding and conversion, marketing and tracking, and niche podcasting. [tweetthis]“If you keep hammering on a topic that resonates with people, stuff still sits on the internet and attracts people.” - Brian [/tweetthis] Here are today’s conversation points: Making quality contentFriday snapshots, Spotify Wrapped Year in ReviewBlack Friday and Cyber Monday wrap-upShopify checkouts, quirks, and limitationsNomination for bootstrapper podcastsProcessKit onboarding and the core of the productHow to change from conversion to paid?MarketingMarketing and tracking from two different sourcesPaypal, what?!Focusing your marketing efforts; niching downGoals for 2021: consistencyPodcasting in a niche versus having a wide audience [tweetthis]“When you’re selling in an app store but you have your own website, there is a big disconnect on tracking.” - Jordan [/tweetthis] Resources: Microconf: SaaS Podcast Awards SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

On this episode of Bootstrapped Web (dubbed the “anything but election talk” episode), Jordan and Brian go over Carthook’s exciting launch in the Shopify App Store and ProcessKit’s visual upgrade. Brian also has a couple of aces up his sleeve when it comes to high level changes as well as day-to-day uses for ProcessKit. Today the focus is all about what it means to satisfy customers: new and existing customers. How do you convert trial customers? How fast should you handle feature requests? How do you deal with the pressures put onto you by customers? How to show your constant level of progress but how do you filter customer feedback/expectations? [tweetthis]“Anytime you’re talking about visual user updates, especially if it affects the entire app (which this did) you get nervous. People don’t like change, even if it’s better change.” - Brian [/tweetthis] Here are today’s conversation points: The Carthook logo is in the Shopify App Store!Team moraleDepartments that need Jordan’s focusUpdates, expectations, and reviewsThe limitations of being both the designer and founder of a productProcessKit upgrades:To dashboard or not to dashboard?Email templates with liquid tags to increase the dynamic changes for these templatesThe pressure of “What’s next?” and prioritizationThe current competitive climate in SaaSPipeMainStreetVisualize Value [tweetthis]“I think we’ve spoken before about how I look at the company as like, ‘Where is the fire burning...the hottest?’ At any point in time it’s not like everything’s on fire or everything requires attention. There’s usually one part of your company where there’s more going on.” - Jordan [/tweetthis] Resources: Jason Lemkin’s post about Dashboards Pipe MainStreet Visualize Value SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Jordan and Brian are back after a few weeks. It is election week; that means a lot of stress and a lot of chaos. But before that stuff hits the fan, Jordan is launching a new Carthook product inside the Shopify app store and Brian has been redesigning the ProcessKit app to fix little frustrations. They’re also talking about structure, spreadsheets, and the importance of app store reviews [tweetthis]“As we started to add more and more features, the overall structure and experience (and I’m talking about very detailed things) hasn’t kept up and so I wanted to solve for all of these little frustrations in the app that have accumulated.” - Brian [/tweetthis] Here are today’s conversation points: New Carthook products inside the Shopify App StorePreparations and anticipating the launchSpreadsheets and scenariosThe Prisoner’s DilemmaDynamic pricing and price pointsProcessKit App redesignProgress in SaaS productsCommunity-based promotionsMarketing and funnelingBeing able to separate yourself from your businessThe importance of customer experience and app store reviewsJordan’s new obsession: Cohere [tweetthis]“It is a prisoner’s dilemma. You’re stuck, you don’t have all the information. What you do has a big impact on them, what they do has a big impact on you. But you’re not colluding.” - Jordan [/tweetthis] Resources: How to Price Your SaaS Product by Patrick Campbell Cohere.so Cohere.so/demo SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Today Brian and Jordan are talking about deadlines, Black Friday, and a little bit of introspection. They go over their love/hate relationship with mornings. They also take a deep dive into hopes, dreams, dedication, and hiring true believers. [tweetthis]“I still really believe in dedicating time to writing tests and for us that really means integration tests and feature tests.” - Brian [/tweetthis] Here are today’s conversation points: The Carthook deadlineHow the new ProcessKit developer stepped upTesting features, web integration expectationsDifferent ways of coping with stressThe importance of mornings:Brian’s morning routineJordan’s morning routineCan you change whether or not you can be a morning person?Hopes, dreams, and dedication“What is the worst case scenario here?”When it is okay to forgo delegating and doing things yourself?Freelancing versus Full-Time EmployeeMarketing projectsHiring a true believer [tweetthis]“When you make a decision, go harder at it.” - Jordan [/tweetthis] SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

On today’s episode of Bootstrapped Web, Brian and Jordan are joined by Ian Landsman from HelpSpot. Ian has made product after product over the years, from UserScape to HelpSpot to LaravelJobs and Thermostatio. You can find him on Twitter or you can learn more about him on his website. Brian, Jordan, and Ian are talking all about podcasts, business models, and privacy on the internet. They also go over the lessons they’ve all learned from previous products and projects they have been involved in. [tweetthis]“How many years, how many decades, can you keep pushing project management software when that space just gets so big and so competitive?” - Brian [/tweetthis] Here are today’s conversation points: Ian’s potential new podcast: structure or no structure?Hey, Clubhouse, and other email servicesThe hidden cost of privacy and complacency in a productPrevious products, projects, and the lessons learnedHow involved Ian, after being 15 years into HelpSpotWhat does feature development look like for Ian?Optimizing websites as supplementary platformsBusiness models: per user, paying per clientsAre demos worth it?Affiliate programs and consulting hang ups for ProcessKitThird party hosting and consulting companiesReal-time brainstorming about onboarding consultants [tweetthis]“Clubhouse jumped the shark from being exclusive to just being ‘annoyed that you couldn’t get in and now you’re resentful.’ And then, of course, I got an invite and a DM a minute later. [laughs]” - Jordan [/tweetthis] Ian Landsman Clubhouse Hey SellerFlows ClickFunnels SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re in a great mood on today here atf Bootstrapped Web. We’re talking about drive-in movies, apple picking, AirBnB’s, Twitter, and business updates. This episode is a bit of a topic potpourri is as we cover new features, hiring and interview processes, big picture visions, and building communities. [tweetthis]“Aside from the obvious goal of marketing (which is to grow traffic and leads and sales), I think the bigger goal should be to build community.” - Brian [/tweetthis] Here are today’s conversation points: ProcessKit fields and featuresWeb developer updatesCarthook’s newest app for ShopifyTheir new full-time, in-house product designerSwitching ProcessKit marketing site to a static site to WordpressStatic vs DynamicThe hiring and interviewing processThe importance of culture fit and temperamentLooking at the big picture and company design“What kind of company do I want to build?”Building an ideal community, and longevityBuilding relationshipsSnap Friday and current hobbies [tweetthis]“Our culture fit is a nice, optimistic, happy person. And that might sound really thin but it really matters. If you’re naturally optimistic and curious, it leads to happiness, even in times of stress.” - Jordan [/tweetthis] Resources: WeWorkRemotely Dynamite Jobs Notion SubStack 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 behind the (brand new) mics. They’re reminiscing about the beginning of the podcast, the fires in the west coast, and catching up on the latest news in the industry as well as their businesses. [tweetthis]“From a design standpoint, in the first year of an app, so many things change, like, in terms of the feature set and the scope.” - Brian [/tweetthis] Here are today’s conversation points: The tail end of the hiring processUsing the Silo strategy5 years in the business of podcasting and with our productsPersonnel shake-up in ProcessKitFinance topic: the launch of Long Term Stock ExchangeMaking progress in different stages of productsNew feature: Dynamic rolesCompetitionAudiences BuildingGetting enjoyment from personal and professional endeavors...or not“You are not a product.”The Billion Dollar BlogHow important is audience building? [tweetthis]“So much is determined by that initial burst of energy and that initial first year or two that sets you up on this trajectory.” - Jordan [/tweetthis] Resources: Mallowtech.com SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

It’s been a little while but Brian and Jordan are back behind the mics. On today’s episode, they’re talking about vacations, a long first week back, marketing, big news with Carthook, cold emails, and guest features. [tweetthis]“I wanted to get things moving and basically get things up and running, so I hired a marketer” - Brian [/tweetthis] Here are today’s conversation points: Carthook, Shopify, and working togetherHow Shopify worksWhat cold emailers get wrongConversion rates and automationInitial onboarding systems and portalsGuest featuresQuestioning ourselvesBenedict Deicke’s Tweet [tweetthis]“The wins don’t last very long. They just whiz by and then it’s just like, ‘Onto the next challenge, onto the next challenge, onto the next thing.” - Jordan [/tweetthis] Resources: LemList SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re back with “Boo-strapped Web”. We’re behind the mic talking about stress, marketing, executing decisions, and guilt over new hire experiences. Lastly, we’re going over the latest news in startup financing, which could blow everything out of the water: rolling funds. [tweetthis]“Saas is an ongoing chicken or egg problem and it happens more in the product side and maybe even more so on the marketing side.” - Brian [/tweetthis] Here are today’s conversation points: New Hire ExperiencesNew employee Slack introductionsPoweredBySearch’s great online course/training for new hiresSaaS = Chicken or Egg ProblemMarketingZapierRolling fundsSahil Lavingia (Gumroad)Exemption 506-B, 506-B, and SolicitationFunding per quarterBetter access to capital, on better termsTransparency will be key [tweetthis]“Audience is now a new form of power, it’s investing power. So if you have an audience and you take a stance and people believe in what you believe in, you can just raise your hand and now you’re a VC, yourself. If a fund can raise money this way, why can’t a startup?” - Jordan [/tweetthis] Resources: SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Today we’re talking about camping ratios, COVID and Black Friday, the eCommerce boom due to COVID, emotions versus moods, Twitter, and competitors. We go over some bold and unique marketing strategies with ProcessKit, how we’ve won Jordan over in the “Working-from-home” battle, and about hiring contractors and coaches. [tweetthis]“He found the reviews where they’re complaining about the competitors and we’re, like, featuring those. Not to just poke at them but to show, ‘If [the customers] complain about this, here’s how ProcessKit solves that.” - Brian [/tweetthis] Here are today’s conversation points: COVID trends and looking into the near futureCompetitor hype and making a dent in the market“Aggressive” marketing in ProcessKitPeople management and coachesHiring contractors for marketing strategiesEmbracing the working from home life [tweetthis]“Identify the difference between an emotion and a mood. A tweet from a competitor, that creates an emotion. But my mood is dictated by, like, my family and my wife and my amazing kids and our health. But how to separate those two out and not let an emotion ruin the mood, feels like a new skill.” - Jordan [/tweetthis] Resources: SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re back after a two-week break. More specifically, a camping and Niagra Falls break. Today we go over two kinds of VC: vacations and venture capital. Not to mention, we go over ProcessKit’s newest marketing news, Ali Mese’s article on Medium, and our thoughts on positioning. [tweetthis]“I’m trying to understand the type of person who discovers a SaaS product and starts emailing their support every single day for fourteen days straight, with multiple paragraphs.” - Brian [/tweetthis] Here are today’s conversation points: How do you know when you need a vacation?Brian’s new purchaseHow often do you contact support?MarketingPositioning and building for additional platform integrationsAli Mese’s article on MediumKeyword research and other marketing ideas for ProcessKitKnow who your best ideal customers areJordan’s lessons in venture capital [tweetthis]“I always have in my mind that I have to be having the right dream. So if you win, make sure you want that outcome.” - Jordan [/tweetthis] Resources: “To Build a Business Empire, Own an Opinion, Not a Marketing Budget” by Ali Mese (published on Medium) SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re back in the studio with a very special agenda… in that we don’t have an agenda today. So we turned to Twitter to ask listeners and followers what topics they would be interested in hearing about. If you have a question or a comment you’d like us to cover in a future episode, feel free to tweet it to us! Today we cover everything from product management to marketing to hobbies. [tweetthis]“To me the most important part of [product management] is the customer feedback.” - Brian [/tweetthis] Here are today’s conversation points: Product Management with ProcessKit and CarthookHiring and delegating in the early days of a product or businessMarketing these days is a puzzleTwitter addictionsManaging product requests from usersMarlo, the special guestHow much time and money do you spend on hobbies?COVID budgetingFamily and school plans for the futureTwitter conversations:Financing and FundingDay-to-day tasks: A Day in the Life of Jordan GalHow we feel about our businesses and progress [tweetthis]“It’s a muscle; that ability to trust other people with very very critical things. It’s not an easy thing to get over.” - Jordan, on delegating important tasks to someone else[/tweetthis] Resources: The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It, by Michael E. Gerber @PoweredBySearch Twitter Twitter: @JordanGal Twitter: @CasJam Sezzle Afterpay SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re back and we have so much to talk about. First off, we’d like to dedicate this episode to Ian Landsman and his twitter account. “Hey” seems to have taken Twitter by storm. We’ll talk about how we feel about that, and, of course, we’ll update you on what’s going on in our businesses as well. [tweetthis]"For an everyday email app, I need it to be as clean and simple as possible. But the experience and the functionality and the UI makes a lot of sense, I think." - Brian, on Hey from Basecamp [/tweetthis] Here are today’s conversation points: Hey (from Basecamp): the pros & cons, and the controversy with the Apple StoreHiring at CarthookRecruitersPeople Ops personCulture and trainingOnboarding updates at ProcessKitTo build or to market, that is the questionForms featuresMarketing tasks on my to-do list [tweetthis]“Now we have 8 completely new people we’ve never met, we probably won’t be able to see for, like, a year. How do we give them a good experience? How do we make sure they don’t feel isolated?” - Jordan, on hiring new team members during COVID [/tweetthis] Resources/Links: HEY - Email at its best, new from Basecamp Help Scout - Simple Customer Service Software and Education Dynamite Jobs Substack SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We’re back behind the mic today after a one-week hiatus. We had originally recorded an episode last week (which addressed current events) but decided not to publish it. Our hearts do go out to everyone in this time of chaos and uncertainty. This week, we’re back, talking about business, bad habits, and kindergarten graduation parades. We’re talking about ProcessKit’s onboarding updates and one of their newest customers. We’re also talking about Jordan’s big problem and his recruiting and hiring issues. [tweetthis]"He turned the tables on me and we bartered. So he’s a paying customer of ProcessKit and I gave him a pretty big ProcessKit plan in exchange for him writing three of these pages for ProcessKit." - Brian [/tweetthis] Here are today’s conversation points: Jordan’s big problem: putting off strategic tasks, but then having no energyBrian’s early morning exercise scheduleBrian’s ProcessKit’s onboarding updatesThe various levels of customersTools, widgets, checklists, and onboarding coursesWhat each customer needs in order to be successfulJordan’s recruiting and hiring processTheir first (in a long time) fully remote hireBrian’s newest customer experienceWhat to do with B2B SaaS these days?E-commerce platform issues [tweetthis]"The mistakes in hiring are more costly than any monetary mistake. Like, buying the wrong thing, using the wrong software, hiring the wrong consultant. I see those as monetary mistakes. When you making a hiring mistake, it hurts so much more.” - Jordan [/tweetthis] Resources/Links: SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

The world is in chaos but we’re still here. Today we’re talking about some of the trends and the future of podcasting after some big news with The Joe Rogan Experience. We’re also going over some updates with Carthook, ProcessKit, and Audience Ops. [tweetthis]"It does seem like there’s still that massive gap between the seed rounds and the Series A. Right? When you’ve grown to a certain level and you still need more firepower to grow." - Brian [/tweetthis] Here are today’s conversation points: The big debate over Joe Rogan’s Spotify dealJordan’s (who is not soliciting for investments, SCC) fears over investorsProcessKit’s onboarding course, not quite readyFunding: social media ads, marketing partnerships (affiliates and referrals)Jordan’s biggest deal ever...and he didn’t even talk to the prospectDifficult clients in Audience Ops [tweetthis]"You’ve been working on something for over five years. This is all you care about. You love it. You love the job, the company, the people. There’s so much involved in that. How are you supposed to find investors that are going to respect that?” - Jordan [/tweetthis] Resources/Links: Substack SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

In today’s episode we’re talking about socializing with family friends and work during the pandemic, as well as the latest news and questions on our minds about the current status of tech and the world. PokerStars, weekly stand-ups, Facebook, and what reopening might look like. The big question on everyone’s mind is: “How long is this going to last?” In business news, we’re talking about Brian’s new ProcessKit course, and Jordan’s views on hiring. [tweetthis]"You’re taking money off the table but you’re also taking off the table, the desire to sell when the first semi-big offer comes along and instead go super-big." - Brian [/tweetthis] Here are today’s conversation points: Facebook newsJordan’s most popular tweet everTaking on more money and the possibility of hitting zeroWhat is Clubhouse and why is it so big right now?Serendipitous audio conversations versus Twitter versus podcastingPrivate podcastsInteresting new platforms: SubstackUpdates on Brian’s new course about ProcessKitJordan’s views on hiringBrian’s work on the sales demos [tweetthis]"People watch how you treat people and then they put themselves in those shoes.” - Jordan [/tweetthis] Resources/Links: Clubhouse.io Substack SunriseKPI Productize Audience Ops ProcessKit Carthook

Welcome back! Brian and Jordan are back behind the mic. We’re talking about ProcessKit’s best month, and Brian’s excitement about moving forward and making progress. We’re also talking about Jordan’s experience with Carthook’s people coach and accidental faux pas with his leadership team. [tweetthis]"I am acting fast on a lot of the smaller requests. I only do it when I’ve heard it two or three times from different customers. Usually and hopefully I’m shipping something fast and notifying multiple customers that, ‘Hey, we just shipped that thing." - Brian [/tweetthis] Here are today’s conversation points: ProcessKit’s best month with conversionsJordan’s focus on hiring and salariesBrian’s focus for ProcessKit: onboardingBrian’s old blog postsSetting up SEOJordan’s humbling experience with the people coachAccidentally taking away authorityBrian’s support requests on ProcessKit [tweetthis]"What am I really doing though? I’m taking authority away from their manager. I’m not allowing that manager to be that person, resource, and that trust and that bond and… I’m messing with that and it’s not helpful." - Jordan [/tweetthis] Resources/Links: Ahrefs.com SunriseKPI Productize Audience Ops ProcessKit Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

On today’s episode, we discuss the real value of a business coach. Jordan has announced that he would like to try his hand at it and Brian shares his own experience with it. We compare the pros and cons of being a coach for other founders and we explore why it is a good revenue source. We also continue our Armchair Quarterbacking Sessions with Derrick Reimer’s project Level. Derrick has noticed some productivity issues with the platform, Slack. He is out to recreate an alternative that can be customized for the tech world, where distractions are project killers. We offer our impressions of the idea and analyze how Derrick is approaching his product development. [tweetthis]There are so many really talented, really smart, really motivated people, they just want to work remotely. - Brian[/tweetthis] Here are today’s conversation points: Getting ready for MicroConf. Brian’s update on the podcasting service. The only stumbling block Brian has encountered. Jordan’s plans to start coaching. Why he is interested in exploring coaching. Who would benefit from Jordan’s coaching? The value of a good business coach. The pros and cons of being a coach. Armchair Quarterbacking Session: Level. Building an alternative to Slack, and is it possible? Are there any benefits to being transparent? Jordan’s advice to Derrick. Brian’s impressions of Derrick’s idea. [tweetthis]If you are going to provide value, it's not just talking, it's work. - Jordan[/tweetthis] Resources Mentioned Today: Audience Ops Carthook Derrick Reimer’s Twitter Jordangal.com Jordan’s email Jordan’s Twitter Level Level on Twitter MicroConf Productize Slack As always, thanks for tuning in. Head here to leave a review on iTunes.

Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are starting with Andrew Culver’s SaaS product, Bullet Train. We also give general updates on what is going with Carthook and Audience Ops. So tune in to hear about Brian’s new service and Jordan’s newfound ambition after having a rare full team meetup. [tweetthis]We [founders] think in a certain way and maybe we don't remember what it is like to be an employee. - Jordan[/tweetthis] Here are today’s conversation points: How having Rok and Ben around has energized Carthook’s team. The presentations and social activities that helped Jordan’s team get better in step with each other. Adjusting back to regular business after Rok and Ben left. Brian’s new podcasting service. The hiring process Brian is using to build his podcast service. An update on the Productize Course and Brian’s closed cart approach. Jordan’s upcoming conference projects. The struggle of working during business travel. The benefit of doing one-on-one discussions with your employees. The first armchair quarterbacking session: Bullet Train. Why agencies would be the best fit for Bullet Train. [tweetthis]Nobody is going to get as fired up and keep pushing than the founder. - Brian[/tweetthis] Resources Mentioned Today: Audience Ops Bullet Train Carthook MicroConf. Productize Shopify Unite As always, thanks for tuning in. Head here to leave a review on iTunes.

We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service. Ben Fisher is the co-founder of Carthook and head of product. Rok Knez is Carthook’s lead developer. He usually manages the company office over in Slovenia. Both Ben and Rok were a part of the company since the very beginning. The guys share how they met and how the business has gone from 3 guys hanging out to the large-scale team that is today’s Carthook. We discuss the technical issues that have reared their ugly head the last few months and Ben explains how they coped with this inevitable part of the business. Today the hood is being lifted on Carthook and we will learn about how Jordan and his team interact with each other and their clients. Buckle up for a very technical episode! [tweetthis]For bootstrapping new software startups, choose a more mature framework, rather than the trendiest stuff. - Brian[/tweetthis] Here are today’s conversation points: Introducing Ben and Rok. How Ben and Rok met Jordan and got involved in Carthook. How Rok hired the engineering team. Who helps with product design? The new style guide the team has recently adopted. How Carthook’s tech stack has evolved. The importance of not cutting corners. The benefits of using Angular. Carthook’s road-mapping process. When do frameworks and processes matter? The 3 questions the team ask themselves when making decisions. How Hiten Shah has influenced Carthook’s process. How Jordan and the original team have coped with working with a larger team. What Jordan and his team have learned about their product. The importance of choosing the right colleagues. [tweetthis]Spend whatever we need to spend, and eventually they [Ben & Rok] took that advice and now I regret it a bit. - Jordan[/tweetthis] Resources Mentioned Today: Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working properly and Jordan and his team are seeing some major cultural shifts in the business. Brian has found himself with some downtime, so now he is thinking about new avenues for Audience Ops. Brian outlines his idea for a new service offered through Audience Ops. An done-for-you podcasting service. He gets Jordan’s feedback and really explores why he thinks podcasts are the next logical step for the business. He also drops a big announcement… Brian wants to learn to code. We have some interesting conversation about alternative content on this episode and some really useful reflections on the founder’s role within his company. [tweetthis]If somebody asked the most valuable thing you’ve learned the past months it would be related to our process. - Jordan[/tweetthis] Here are today’s conversation points: Get ready for MicroConf. Brian’s new service launch. Considerations for future podcast topics. Jordan’s March recap. Why Brian wants to launch a new service. The all-done-for-you podcast service breakdown. Brian’s small beta group for the new service and the results. The benefits of podcasting content. The second version of Carthook update. Jordan’s webinar experiment. The benefits of webinars. How to create pitch-hitter scenarios. How Carthook uses paid ads. The ad strategy Jordan used for the webinar. Brian’s results from his Productize webinar. Why Brian wants to learn to code. How to be a full stack product person. Jordan’s adjustment to a larger work team and changing the dynamic. [tweetthis]If you are a designer of web applications, you should have a full stack skillset. - Brian[/tweetthis] Resources Mentioned Today: Audience Ops Podcasting Service Bullet Train CodeMentor.io Carthook Castos MicroConf Ops Calendar Productize As always, thanks for tuning in. Head here to leave a review on iTunes.

2017 is coming to a close and Jordan and Brian are looking back on this explosive year. They also share their plans for 2018. Audience Ops and Carthook both saw tremendous amounts of growth this year. That growth has caused the guys to reflect on 2017 and the lessons they have taken away from the experience. Brian has seen an uptake in sign-ups and Audience Ops has ridden a roller coaster this year. Brian shares what he learned from the sudden stop and go growth of the business. 2018 looks to be a major year for Audience Ops, Ops Calendar, and Productize. Jordan has had a monster of a year. He is recuperating from a breakneck year with a well deserved slow down period. Jordan shares what this year taught him about team building and how he plans to fix some of the issues he noticed during Carthook’s major growth spurt. [tweetthis]Growth is great, but it will mask problems. - Jordan[/tweetthis] Here are today’s conversation points: The problems Jordan discovered when onboarding new team members. Brian’s surge in service sign-ups. Carthook’s Drip campaign disaster. Setting new goals and themes for 2018. The downside of sudden growth. Coping with wild growth and rapid plunge of business. Jordan’s tech issue in 2017 and how he plans to fix them. Productize’s new course launch in January. Jordan’s general observations about 2017 and 2018. Brian’s general observations about 2017 and 2018. [tweetthis]I actually have a lot of firepower to play with going into 2018 now. - Brian[/tweetthis] Resources Mentioned: Audience Ops CasJam Carthook Ops Calendar Productize As always, thanks for tuning in. Head here to leave a review on iTunes.

2017 has been a phenomenal year for Jordan and Brian. On today’s episode, they give the audience an update on the businesses and offer a glimpse into their plans for 2018. Brian is going to shift focus to Productize and relaunch a bigger and better product later. This means he will be closing enrollment in the course and beginning the maintenance phase of this upgrade. He shares how he reached this decision and why he is excited by the new possibilities it can bring. Jordan is adjusting to a growing business and finding ways to restructure his processes to make Carthook more efficient. He uses his previous experience over the last year to prepare Brian for his up-coming wild ride. The guys also share some new tools and resources that have found to make this new stage in their businesses a little easier. [tweetthis]This has been the biggest spike in revenue for Productize and way beyond expectations. - Brian [/tweetthis] Here are today’s conversation points: Brian’s shift to working on Productize during the month of December. Jordan’s look back over his year, from an investor’s point of view. Coping with a larger team and the issues that arise. Brian’s awesome Black Friday! Brian’s plans for relaunching Productize. Jordan’s new team members and the importance of good content writing. How Jordan is restructuring his processes. The trade-offs a team has to make for the sake of speed. How to build a great product without slowing down the project. [tweetthis]It's still a mindset and a process, if everything is a trade-off, where are you putting the emphasis? - Jordan [/tweetthis] Resources Mentioned Today: Appcues Audience Ops Beacon Carthook Drift Seeking Wisdom Podcast GoVideo Productize Course Ops Calendar Soapbox As always, thanks for tuning in. Head here to leave a review on iTunes.

Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move the business to the next stage. Carthook is also growing their team and there have been some growing pains in the communication process. There have been some hard lessons in the process that Jordan hints at that could help business owners build their systems more effectively. Brian has been putting a lot of energy and time into Ops Calendar. He is getting a lot of interest in the service and the product. This new interest has given him a reason to ask the question if freemium is a viable option for Audience Ops. There is some really useful and thoughtful discussion in today’s episode, so tune in to join the conversation. [tweetthis]I feel freemium is one of these things that a lot of bootstrappers have not given a fair shake as a strategy. - Brian[/tweetthis] Here are today’s conversation points: The “fattening up” process of Carthook. The struggles of building an effective team. Audience Ops and Ops Calendar progress reports. Ops Calendar’s features and fixing the unexpected bugs. The usefulness of Slack. The benefits of letting people “win.” Working with freelancers and building a positive business culture around them. Jordan’s marketing experiments and the results. The pros and cons of freemium. [tweetthis]I admire people who are super product focused because I think it's fun. It's so creative and interesting. - Jordan[/tweetthis] Resources Mentioned Today: Audience Ops Calendar Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

We have both reached a turning point in our marketing campaigns. Jordan has launched a new marketing funnel for Carthook’s Shopify tool. Brian has been running a new marketing campaign for Ops Calendar. We share how the campaigns are working for us and offer each other advice on how to improve our strategies. We also discuss how we keep our team culture positive when we ourselves are super busy and can’t give our undivided attention to individual projects. Our teams are growing and changing and we explore how we are coping with these mostly positive developments. It’s a good time for both Ops Calendar and Carthook! [tweetthis]These calls are dripping in, inbound, organically...these just feel like good signs to me. - Brian [/tweetthis] Here are today’s conversation points: Carthook’s new paid marketing campaign. Ops Calendar is finding a new audience and why Brian is excited by this. How Brian uses and makes sense of Audience Ops’ analytics and metrics. How Jordan set up his marketing campaign. Jordan’s 3 blog post marketing strategy. Other insights into email and ad marketing. How we differ in our methods of team building and encouraging positive company culture. [tweetthis]I tell people on my team think like an owner, think what do I need to fix this - Jordan[/tweetthis] Resources Mentioned Today: Audience Ops Carthook Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.

Today on Bootstrapped Web Jordan and Brian discuss what’s going on in their individual businesses. Brian is setting up Ops Calendar and takes today’s episode as a chance to get Jordan’s feedback from the customer’s point of view. Listeners who are interested in Ops Calendar can get excited because Brian gives a detailed description of what his service offers. Jordan has had some problems with retaining new team members. He shares what he has learned about the hiring process and how he keeps company morale high. He also shares a new service he has found for businesses who hire team members in different states and he is psyched by his results. [tweetthis]All your employees, there is a level of trust... it's better for everyone to be honest. - Jordan[/tweetthis] Here are today’s conversation points: The benefits of providing hardware and tools to your remote team members. The role trust plays in working with a remote team. Ops Calendar is going live! Jordan’s advice to Brian regarding Ops Calendar’s structure. What Ops Calendar can do for each tier. Why a business should always be recruiting. The importance of staying positive when business isn’t going as expected. How much transparency is too much? Why the service Officeengine is awesome! [tweetthis]Having full-time employees, especially in different states, adds a massive layer of complexity. - Brian [/tweetthis] Resources Mentioned Today: Carthook Ops Calendar Officeengine As always, thanks for tuning in. Head here to leave a review in iTunes.

We cover a lot in this episode of Bootstrapped Web. We give our listeners an update on both companies’ progress and we discuss some exciting news in the startup world. Brian shares some of the goals he has for Audience Ops in the near future. Jordan has an awesome story to share about his new VIP client. We compare our business needs and consider the unexpected problems that come with growth. We also discuss two really insightful articles that just came out, Amazon’s New Customer, by Ben Thompson and Why I Bought Your Software by Justin Jackson. Both articles are great reads and we have some good takeaways from them. [tweetthis]If it's not 100% core to what we do, first option will be to integrate with the big player in the field. - Jordan[/tweetthis] Here are today’s conversation points: Jordan's new VIP customer. Ben Thompson’s latest article. The Amazon and Whole Foods merger. Why the merger is a good thing. Lessons Jordan has learned from his new hire. The benefits of mastermind groups. The biggest expense for any growing company. How do you know when you’ve reached “feature completeness?” Brian’s Ops Calendar update. Justin Jackson’s latest article. Seeking Wisdom with David Cancel. [tweetthis]I feel like, if you're not in such a cut-throat, competitive space, you can get by with a slower road map. - Brian[/tweetthis] Resources Mentioned Today: Amazon’s New Customer, by Ben Thompson Audience Ops Carthook Drift Front App Intercom Ops Calendar Seeking Wisdom Why I Bought Your Software, by Justin Jackson As always, thanks for tuning in. Head here to leave a review in iTunes.

Happily, our client loads are increasing, but our staffs are starting to feel the increased workload. So, we need to hire more people to keep up. It’s a good problem to have. On today’s episode, we compare our staffing needs and discuss how we are trying to build a process that frees us both up for “CEO tasks.” As our businesses grow, our roles change. Brian shares his plans to cope with a couple of team members exiting the company. While Jordan recently spent some time away with his family. He shares how that trip changed how he looks at his team and responsibilities to the company. [tweetthis]I have to perform better as a CEO...the interference portion of my equation is just preposterous. - Jordan[/tweetthis] Here are today’s conversation points: The uptake in business for Audience Ops. Brian’s plan to cope with the increased workload. Filling team positions for growth at Audience Ops. The ups and downs of working with a remote team. Jordan’s recent trip to New York. The “performance equation:” performance= potential - interference. How the performance equation has helped Jordan look at Carthook’s growth differently. How difficult it can be to transition into the “CEO role.” [tweetthis]Forget limiting the headcount, let’s get more than enough people on board and spread the work around. - Brian [/tweetthis] Resources Mentioned Today: Audience Ops Carthook Productize As always, thanks for tuning in. Head here to leave a review in iTunes.

Today Brian and Jordan discuss growth. In Jordan’s case he is dealing with sudden growth, and in Brian’s case, he is planning for growth. Both share how they are handling this wonderful problem. Jordan has been focused on getting Carthook’s marketing up and running again, but it has become clear that his team needs him to focus on improving the customer support. It has been a struggle to really pinpoint what the team needs. Jordan calls it “customer success,” but Brian isn’t so sure that’s the best title for the position. Brian is working on his KPI (Key Performance Indicators.) While making the dashboard for these KPI, he learned that sometimes you need to just hire someone. Brian is also planning to do some hiring, he needs two project managers and a writer. He caps off today’s topics with an article from the website Baremetrics. [tweetthis]I'm now in this mindset with this business, it is all about growth. - Brian[/tweetthis] Here are the conversation points: Brian’s four major categories for his KPI. When to know you need to hire someone. Jordan’s ever-growing stress. Jordan’s undefinable job description. What does “customer success” mean? What Jordan needs for this new position. The importance of taking care of “home base.” Brian’s hiring needs. Josh Pigford’s blog post. [tweetthis]What we need to do is work harder and smarter on making sure existing customers are satisfied and happy. - Jordan[/tweetthis] Resources Mentioned Today: Being a Solo Founder: Pros, Cons, Tips, and Tricks, by Josh Pigford Audience Ops Carthook Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.