Bootstrapped Web

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 u...

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, a...

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...

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...

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 con...

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 hav...

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 th...

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...

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...

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, marketi...

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 exist...

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 [tweetthi...

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 [/tweetthi...

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...

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...

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 co...

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,...

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 mark...

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 competitor...

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 ev...

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...

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 experie...

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...

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...

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 n...