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

We’re back! We’re excited about some winter weather activities and all of our 2020 ideas. We talk about brainstorming, questions, nomenclature, tiny conferences, and profitability. Here are today’s conversation points: Looking back one last time on 2019 Jordan is shifting from a direct-response mindset to a brand awareness mindset Brian’s contemplative train ride and mini-retreat … Continue reading Positioning and Profitability

Today we’re talking about getting back to work after the holiday “festivities”, the inability to unplug, slowing down in December, the themes that ran through 2019, and what our themes for 2020 will be. Here are today’s conversation points: What to do when you can’t unplug your brain Slumps around the holidays 2019 was a … Continue reading Back At It

Brian and Jordan are back! We talk about holiday plans, the work-from-home life and coworking spaces, seeing and working with other human beings, spending all of our money at Starbucks, and the latest in marketing techniques. We talk about our past marketing mistakes and what went well, as well as what we plan on doing … Continue reading Marketing Plans for 2020

Jordan and Brian are back behind the mic before Thanksgiving. Jordan talks about how great it feels to be unnecessary (at work) and various B-to-B and B-to-C marketing techniques. Brian talks about kits, his “new trialers”, and Processkit updates. They also talk about one of DHH’s Tweet-rants and what they’re grateful for. Here are today’s … Continue reading Marketing Loose Ends & Funding Gaps

Today we’re live and in a rush since Jordan has to take his kids to lunch on their off-day!  We talk about post-Halloween shenanigans, Brian’s 37th birthday (at least, he’s not 40), the stats and news from Process Kit’s launch, capturing the creative process, and Jordan’s code freeze.  We also talk about how to capture … Continue reading Post-Launch & Code Freezes

Brian and (a sick) Jordan are back talking about upcoming Halloween festivities, what they missed out on by missing MicroConf (in Croatia), their thoughts on SEO, product vs. marketing, new podcasting ideas, and the new ProcessKit website. Here are today’s conversation points: MicroConf in Croatia The importance of SEO Brian’s marketing push and Launch Workshop … Continue reading Product Brain vs Marketing Brain

Jordan and Brian are back with updates (even if they’re not so great). Brain updates us on the developments (or lack thereof) with his developer and how communication issues have played a part in the lack of progress. He also talks about how to move forward from these issues and how he has learned from … Continue reading So Much for That Plan

Jordan and Brian are back in the studio. Today the main focus is on the continuous adjustments needed in the software industry. They also quickly cover the trend of SaaS companies doing conferences and community-based marketing. Jordan talks about how great Carthook is doing, productivity challenges, goals for the future, some exciting, secret news for … Continue reading Continuous Adjustments

Jordan and Brian are back to a regular podcasting schedule. Brian spent the weekend at a retreat/mastermind group at Martha’s Vineyard. Meanwhile, Jordan was at the Striped Conference. After a quick update, Jordan and Brian talk about the latest episode of a great podcast, MRR, and the latest news on both of their businesses. Here … Continue reading Never Enough MRR

It’s September, which means we’re talking about the changing of the seasons: kids are back in school, we’re gearing up for Black Friday, updating websites, and checking our numbers. Brian talks about his email marketing, hiring developers, and changing website hosts. Jordan talks about what’s new with CartHook and the future of podcasting. Here are … Continue reading Rabbit Holes Within Rabbit Holes

Jordan is back! We talk about what we’ve been up to: family trips to Cape Cod, productivity and the stress before vacations, Michigan in the summer, and buying houses, Brian’s assistant. After catching up, we jump right into updates, price changes, dual-track development, and outsourcing. Here are today’s conversation points: An update to the sales … Continue reading Move It up and Accelerate the Plan

With Jordan out of the studio, today our guest is Ben Orenstein. He is the host of the Art of Product podcast as well as Co-founder of the online tool, Tuple, which was built for remote pair programming on Macs (screenshare with audio). We talk about what makes an effective and splashy launch, hiring freelancers, … Continue reading What Is a “Launch”, Really? w/ Ben Orenstein

Two weeks in a row, and still plenty of topics and updates to discuss! Jordan wants to talk about how startups fail when they take on more opportunities than they can handle. If he decides to pursue any of the big opportunities that popped up recently, what does that mean for Carthook and its employees?  Brian remains focused on prioritizing ProcessKit tasks. Everything feels urgent, and it’s impossible to have patience. There are so many things that he wants to happen, that need to happen, but they won’t get done anytime soon. Also, he shares his thoughts and ideas about case studies/testimonials package for Audience Ops.  “Startups more often die from indigestion than starvation because they’re trying to do too much.” — Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Brian’s in-depth video about ProcessKit’s marketing site progress. Jordan worries about overextending his team’s capacity, creating problems and pain.Brian sets up Help Scout for ProcessKit’s knowledge base docs and live chat.Ridiculous or necessary? Jordan hired ‘people consultant’ to help define job titles and compensation. Brian’s push for case studies content due to decline in new leads for Audience Ops. Carthook’s employment agreements are changing to navigate non-compete issues,  allow side projects, and encourage entrepreneurship.ProcessKit’s paying customer account continues to increase slowly, but Brian still needs to build essential features from archiving projects to restricting permissions.Why Jordan has doubts about Slack and its central impact on team communication.Brian changed ProcessKit’s sign-up process to requiring a call with him to share your questions and objections to get a formal invite. “There’s still so much that I just don’t have in hand to give to people yet. I built the core…there is plenty in the roadmap.” — Brian Powered By the Tweet This PluginTweet This Resources Mentioned Today: Carthook ProcessKit Copywriting for the marketing site for ProcessKit Audience Ops Help Scout Slack Derrick Reimer ConvertKit HubSpot Front Alex Turnbull of Groove on Twitter Hiten Shah on Twitter Crazy Egg Jason Fried on Twitter Shopify Ian Landsman on Twitter Laravel As always, thanks for tuning in. Head here to leave a  review on iTunes.

We are back from a lengthy hiatus and we have plenty to discuss for today’s episode! Brian updates our listeners about ProcessKit and what he is learning from the process. Jordan wants to discuss the price increases coming to Carthook. He also dives into how the price change has affected how his team looks at problems. Brian has his problems with ProcessKit that he is exploring and hopes to address in due time. “All these things that we’re talking about are priorities. They all need to get done today, yesterday, the question is which one am I going to work on today?” — Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Carthook’s price increase and why Jordan thinks it took too long.How Carthook is approaching existing customers.How the price change is making Carthook a healthy company.Lincoln Murphy’s latest article.Why Brian is favoring a slow launch approach with ProcessKit.The benefits of creating a visual pipeline system.The reasons to tell a client no and the possible fallout.The problems and changes Jordan and his team have addressed with Carthook.Wes Bush’s helpful book. “This makes us astronomically more expensive than the competitors and we are okay with that. The bigger thing is not the pricing change, the bigger thing is the process change.” — Jordan Powered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook ProcessKit Product-Led Growth: How to Build a Product That Sells Itself by Wes Bush As always, thanks for tuning in. Head here to leave a  review on iTunes.

Hey, we’re back and we’ve got some lessons and updates to share with you! Both of us have plans to travel over the next few weeks. Jordan will be visiting his Slovenia team and Brian will be attending WP Elevation. Carthook and ProcessKit are both at a pivotal stage of growth and we try to encourage each other during this episode to keep pushing forward and learn from our mistakes. Brian also has a couple announcements. Productize will be opening up to new users on June 7, 2019, it will last for about a week. Also, he will be hosting a live Q&A session for his users and potential users on July 11th. So, if Productize sounds like something you could use in your business, keep an eye out for these events. “This week I had a few calls with people who started using (ProcessKit) and about three people have said, ‘yeah I plan on converting to a paying customer on this.”- Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Jordan’s team has grown and creating a fun and diverse culture.The tweet that went viral and haunts Brian.How Jordan and his team are responding to a security issue.The first and second rounds of invites to ProcessKit, how’s it going?Brian’s expectations for the early stages of ProcessKit.Why Brian has gone ahead and set up a billing system in ProcessKit.Mistakes Carthook made while trying to overhaul analytics and what they learned.Jordan’s plans to build an app and make Carthook a platform.Update on Brian’s new marketing page for Productize. “I’m convinced that the ideal is getting the prospect to buy into your strategy, and then the product that goes along with the strategy.” -Jordan Powered By the Tweet This PluginTweet This Resources Mentioned Today: Carthook Productize ProcessKit WP Elevation As always, thanks for tuning in. Head here to leave a  review in iTunes.