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

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 … Continue reading Talkin shop with Ian Landsman

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. Here are today’s conversation points: ProcessKit fields … Continue reading Company Design

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. Here are today’s conversation points: The tail end of the hiring process Using the Silo strategy … Continue reading Should You Audience?

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. Here are today’s conversation points: Carthook, Shopify, and working together How Shopify works What cold emailers get wrong Conversion … Continue reading The Next Chapter in the Product

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. Here are today’s conversation points: New Hire Experiences New employee Slack introductions PoweredBySearch’s great … Continue reading Chicken or Egg or Fundraise

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. Here are today’s conversation points: COVID trends … Continue reading Hello Competitors

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. Here are today’s conversation points: How do you know … Continue reading What does VC really mean? And marketing.

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 … Continue reading What Should We Talk About?

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 … Continue reading Heyyy + People-ing, Building & Marketing

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. … Continue reading SaaS Onboarding & Recruiting at Scale