Bootstrapped Web

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.