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

We ask ourselves a lot of questions during this episode. Jordan is looking at Carthook and seeing exciting changes but now he has to consider what comes next. Brian is still getting ProcessKit ready for users and has to ask himself who should the first group of users be? He also wants to step away from his sales role in Audience Ops but he is still trying to figure out how that will work. Brian also has some speaking engagements coming up he wants to mention. He will be at WP Elevation in June and CaboPress in September. There is a lot of sound boarding in this episode, so it’s great for somebody who is dealing with company growth and team dynamics in general. ” There is always a baseline of quality and confidence that you need in a given role. It is a huge bonus if the person has already been in the culture and proven to be a solid team member.” – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Brian’s upcoming speaking engagements.The video Brian created to promote ProcessKit.ProcessKit is the new Ops Calendar.Carthook’s profitability and what that means for the company.A change in hiring strategy.How to identify your company’s value proposition.The issues growth can present to a team.Brian’s future plans for Audience Ops.Why you shouldn’t feel guilty about outgrowing your original role. “I am waiting for that moment when we hit that profitability and I don’t feel the need to immediately extend ourselves again.” – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook ProcessKit Ops Calendar 2019 CaboPress WP Elevation As always, thanks for tuning in. Head here to leave a  review in iTunes.

We have had some major decisions to make lately. Brian is working on ProcessKit and his self-imposed deadline is just around the corner. Now, he has to decide if he wants to launch a semi-ready product to his users. We discuss when is the appropriate time to release a product and if you can go back and build it afterward, really. Jordan is exploring the world of financing. It has been an education, to say the least. He shares his discoveries and what perplexes him about the venture capital world. Jordan also talks about when to “play the CEO card” and get the projects you feel need to take priority higher on the list. “Don’t get me wrong, I’m as eager and urgent about this (ProcessKit) as anyone else listening… But, I know that if I were to use this product it’s missing just important things.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Jordan’s frustrating morning and when to play the CEO card.Brian’s update on ProcessKit.When releasing a product to users, when is it really ready?The pros and cons of the trial period pricing strategy.The lessons from MicroConf that helped Jordan decide on an offer.The concept of preferred shares, is this standard practice?The pros and cons of the venture capital option. “It (pricing) really feels like that’s where the leverage is that’s really where you can make the really big mistakes or do things that set you up for success. – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook MicroConf Mixergy – Hiten Shah: How loss of focus and a lawsuit brought about the slow growth and loss of momentum of KISSmetrics ProcessKit As always, thanks for tuning in. Head here to leave a  review in iTunes.

Hey! We are back from MicroConf and we’ve got some great takeaways from the experience. We discuss the speakers and the talks and how the experience changes for us year to year. We also have some updates for you. Brian is still working on ProcessKit and is trying to connect with the right customer base. He shares how he is doing it and what he hopes to accomplish it. He is also thinking about marketing the product. We discuss the benefits of hiring a marketer but we also look at the trickiness of finding someone you can work with effectively. Plus, if you know any good technical writers, send them Brian’s way. Jordan has some exciting milestones to share and a new way of thinking that he hopes will take things to a new level. The Carthook team has grown and the focus has shifted to on-boarding, We discuss the importance of onboarding and making sure your new hire is properly prepared for the job. Jordan also opens the door to a conversation about hiring personal assistance. There are a lot of things to consider when hiring a personal assistant. Jordan shares the process he went through to find his assistant and why he felt it was a necessary investment for him and Carthook. “I think a lot of us have come around to the idea of talking to customers early on during the validation phase but I think it’s better to continue that on a regular basis.”- Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Our MicroConf experience and takeaways.What are Tick Tock projects?Carthook’s Portland MastermindBrian’s update on ProcessKit.The common stumbling blocks founders find when looking for customer feedback.How Carthook is trying to improve its new hire onboarding process.Deciding what is valuable in your product and charging accordingly.Why Brian is considering hiring a marketing expert.Jordan’s personal assistant and what she does for him and the company.The hunt for a technical writer in Audience Ops.How to sell your company to a potential hire and still be realistic. “Marketing site envy is real. Everyone wants a beautiful site. It’s really hard to nail and it’s expensive or it can be really expensive.” – Jordan Powered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Basecamp Carthook MicroConf ProcessKit Worldwide 101 As always, thanks for tuning in. Head here to leave a  review in iTunes.

MicroConf is coming and we’re psyched! We take a glimpse at the schedule for this year’s event and we talk about what we’re looking forward too. Brian has an update on his pricing issue with ProcessKit and the conclusion he came too. Jordan is happy to announce that Carthook’s plateau is over! Brian tries to help him pinpoint the cause but the answer seems to be a combination of things. We also talk about customer service and when is it best to just redirect a customer to another service or product? What’s the best way to save everyone some time and manpower? On my mind right now with ProcessKit… is on-boarding, getting them to switch to it and getting them committed to it. I think that’s probably going to be the biggest challenge with selling this product. — Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Get ready for MicroConf!. What we look forward to during this year’s MicroConf. An update about ProcessKit. The two options Brian is considering for product pricing. The benefit of focusing on team product users. Carthook is finally past the plateau from the holiday season. The onboarding challenges of ProcessKit. Brian’s experience with on-boarding with ConvertKit. The introduction of Customer Engineers into Carthook’s support team. How to tactfully weed out “bad” customers. Brian’s contemplation about leaving the sales role in Audience Ops. I remember at the very beginning I wanted to learn more about how to get things started. Then I wanted to learn things about how to grow, and now I want to learn things about how to manage. — Jordan Powered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook MicroConf ProcessKit As always, thanks for tuning in. Head here to leave a review in iTunes.

MicroConf is just around the corner and we are ready for it! We share our excitement about the conference and encourage you the listeners to say hi if you plan to attend this year. Brian has an update about ProcessKit and he actually has a launch date! He also wants to bounce around some questions about pricing. If you have a suggestion for him let him know at MicroConf.. Jordan is reaching a new phase in Carthook. The team has started experimenting in customer account relations and vetting their customers for better quality in customer service and retention. He shares what they have learned from the process and what it means for current and future Carthook clients. Part of what you’re going to learn in early access is the response to pricing and you can just change it. — JordanPowered By the Tweet This PluginTweet This Here are today’s conversation points: Taking some time off and traveling with the family. Here comes MicroConf! Brian’s ProcessKit update. The 3 resources that Brian has found the most useful for ProcessKit. Carthook’s non-active account experiment. How customers are reacting to the experiment. Coping with zombie customers. ProcessKit’s launch date. The decision to vet Carthook customers and improve churn. The pros and cons of various pricing models. If there’s a value there to be had and you come to an agreement and they’re on board, they’re gonna sign up. — BrianPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook Codementor Go Rails Learn Vanilla JS MicroConf ProcessKit As always, thanks for tuning in. Head here to leave a review in iTunes.

We cover a subject that affects all bootstrappers today. Should you hire or not? This topic comes up because we both are looking to hire some new team members. Jordan has seven job openings and Brian is looking for a new writer for Audience Ops. We discuss how we go about hiring for these positions and why it isn’t always a smooth process. Brian also has some updates on ProcessKit and Productize. For the whole month of March, Productize will be open to new customers. Brian shares what he learned from last year’s open sessions and why he is doing it differently this year. I see nothing wrong with doing all the things to get it to a point to where it has customers… then I say, alright where are the pain points. – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Personal updates and upcoming plans.Brian is getting back into ProcessKit.Productize will be open all March!Brian’s process for finding a new writer for Audience Ops.Jordan’s hiring needs and why it is complicated.Jordan’s approach to hiring new team members.Why some people interview well but are hard to work with.The levers of business and how to use them in the hiring process.The benefits of being a solo founder.Hire to achieve goals, not vanity.Investing time vs. investing moneyCoping with distractions and getting back on track.The 4 lessons Jordan learned from a potential acquisition. There is a lot of social capital that is built up over time and it [acquisition] would have cost a lot of social capital in order to get my way. So, yes it’s my decision, but that’s not free. -JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook Productize ProcessKit As always, thanks for tuning in. Head here to leave a review in iTunes.

MicroConf is right around the corner! We are excited and really looking forward to this year’s event. Brian is jumping back into ProcessKit but he’s struggling to get back into the groove. We discuss why that happens and how we try to keep momentum during a project. We also discuss the role of salespeople and what is a fair incentive in a small team? Carthook is dealing with customers expectations and Jordan made some mistakes during the meeting. He reflects on those mistakes and shares what he decided moving forward when dealing with customer feedback. If something comes to my inbox, something probably went wrong.– BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Looking forward to MicroConf!Brian’s efforts to pick up ProcessKit.How to get back into a project when you’ve been away from it.The 3 mistakes Jordan made during a “What Our Customers are Saying” meeting.What he learned from those mistakes.How to balance quality control with customer expectations.Brian’s bad sales experience.Are salespeople worth the commission?Are shared commissions a good idea?Responding to Derrick Reimer’s tweet.Why you should consult with a customer and not demo. The design space on a company is blank. You can create whatever kind of company you want with whatever incentives. — JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: AudienceOps Carthook Derrick Reimer’s tweet MicroConf ProcessKit As always, thanks for tuning in. Head here to leave a  review in iTunes.

This week, Jordan has been very focused on sales. He and his company are considering hiring their first salespeople. Jordan shares he believes that they’ve gotten complacent and are starting to look at things in the wrong way – in aggregate instead of in detail. Brian went to Colorado last week with one big question: What is Sunrise KPI? Is it a side hustle? Is it a full-time business? Keep working on it or give it up? After assessing the numbers, he’s decided to wrap up his work on Sunrise KPI and focus on ProcessKit. He’s not shutting down Sunrise, just stepping back from adding on to it. Go broad to understand their world. — BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Big Snow Tiny ConfHiring sales people in Jordan’s companyMapping out the existing hiring processThe sales roles within Jordan’s companyThe problem with too many signupsWhat Jordan learned this week from two customer interactionsUnhealthy tension vs. healthy tensionDefining top-of-funnel rulesFuture plans for Sunrise KPIUpdate on current Sunrise KPI numbersShifting Sunrise KPI to a side projectValuing side projectsUpdate on ProcessKitRecording customer callsWhat to ask customers aboutWOCAS Lunches None of this is in stone, and no one tells you that you have to do something a certain way. — JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Big Snow Tiny Conf Sunrise KPI ProcessKit From Bubble to Bubble Gumroad As always, thanks for tuning in. Head here to leave a  review in iTunes.

Today we talk about something that affects all businesses, churn. No matter how successful your business is, everyone deals with customer churn. Jordan has decided to tackle Carthook’s churn problem head-on. He shares with Brian how he and his team have gone “on the offensive” to keep churn low and still bring new customers into the business. In return, Jordan helps Brian sort out what exactly is going with Sunrise KPI. Brian has been surprised by the response to Sunrise KPI. He is actively looking for feedback on the app and, he is trying to decide how far to take the development. He also gives the audience an update on ProcessKit and swears he will get back to it. And you Big Snow Tiny Conf fans will hear about how the Vermont session went. Whether you are interested in VC or not, it’s still a good idea to work on churn. — BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Big Snow Tiny Conf. Jordan’s move to “offensively” preventing churn in Carthook. The lessons Jordan has learned about business strategy. The new process he and his team came up to put those lessons into practice. The current state of SunriseKPI. A ProcessKit update. The meeting that changed Jordan’s view on churn. Always work to make processes and systems the best they can be. How we calculate our churn numbers. The way Jordan identified the right candidates for his new churn approach. The 2 types of customers he is targeting for this new process. As a CEO you want to know that a process is running,not that someone is hoping for things to work out. — JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Big Snow Tiny Conf Carthook ProcessKit Sunrise KPI As always, thanks for tuning in. Head here to leave a  review in iTunes.  

Welcome to 2019! This is our first episode of the year and we have a lot to say! Brian is planning a lot of travel these few months. That means that some of his projects are on the back burner. He gives an update on both ProcessKit and Sunrise KPI and explains his tentative plans for this year. Jordan is getting ready to visit the team in Slovenia and help them move offices. He also discusses some of the goals he has for 2019. These goals include being more transparent with his audience. We debate the pros and cons of that goal as well. Finally, we address the elephant in the room (or on Twitter.) The Drip controversy is fresh in our minds. For those outside of the situation, Drip has announced a price increase and it blew up in their face. We give our opinion on the situation and talk about what Drip did wrong and what their competitors did right. Here’s to an awesome 2019! It’s okay to brag sometimes. But Twitter is so boring when it’s just bragging. — JordanPowered By the Tweet This PluginTweet This Here are today’s conversation points: Brian’s travel plans for the next few months. The audience’s response to Sunrise KPI. A ProcessKit update and plans for 2019. Jordan’s upcoming trip to Slovenia. The culture challenges the Carthook team is dealing with right now. Jordan’s goal to be more honest and open with his audience. Carthook’s end of the year numbers. The lesson Drip can teach software startups. The price increase and the poor handling of the announcement. How Twitter blew up and sparked a debate about the announcement. Our thoughts on the backlash and mob response. How Drip’s competitors took advantage of the mob response. Our comparison of the competitors’ offers and tools. [Sunrise KPI] is a much simpler app,I feel like a lot of bootstrappers are taking too much time to ship code. –BrianPowered By the Tweet This PluginTweet This Resources Mentioned Today: Big Snow Tiny Conf Carthook MicroConf ProcessKit ReCharge NY Sunrise KPI As always, thanks for tuning in. Head here to leave a  review in iTunes.  

We are shying away from discussing goals or resolutions for the businesses this year. Instead, we reflect on how the bootstrapped world and business models have changed. A lot of approaches and marketing techniques have gone by the wayside in the last two years. We share our observations of how self-funding has changed as a strategy. We also talk about the big D-word (downturn) and the real possibility that 2019 might be a major game-changing year for the economy. I feel like..both businesses and consumers has changed a lot recently. People have become more savvy. — BrianPowered By the Tweet This PluginTweet This Today’s conversation points: Our holiday plans. A look back at Brian’s 2018. Sunrise KPI is live! Jordan’s summary of 2018. Why we are forgetting about goals and resolutions. How the bootstrapped world has changed since the beginning of this podcast. What works in self-funding now. The current realistic expectations of the bootstrapping model. How VC funding is going to change in 2019. The pending economic downturn and how to prepare for it. I will be joining TinySeed as a mentor, I’ll get that frontline view of how founders are thinking. — JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook ProcessKit Sunrise KPI TinySeed As always, thanks for tuning in. Head here to leave a  review in iTunes.

The holidays are here! The office parties are going on and Christmas music is everywhere! Today Jordan is celebrating the growth of Carthook by offering his employees stock options. He discusses the stickiness of the decision and the excitement and nervousness that comes with the big announcement.  He also tells a customer story that opened his eyes to user experience and how Carthook can step up their game and really deliver a great customer experience. Brian’s ProcessKit partnership has fallen through. But he’s not discouraged, he shares what it was like to have that difficult conversation and how he plans to move forward. He also announces his second product in a month! Sunrise KPI is Brian’s latest product and he is proud to offer a great tool to his customers. What matters is what’s being interacted with, not just how people are inside of our app, but the end result. — JordanPowered By the Tweet This PluginTweet This Here are today’s conversation points: Preparing for MicroConf Growth. An update on TinySeed. Brian’s new product Sunrise KPI. The customer meeting that changed Jordan’s perspective on his product. ProcessKit’s partnership update. Brian’s Plan B for ProcessKit. Jordan is announcing employee stock options and he’s nervous! I felt we (the partnership) were going to do good things for ProcessKit but I was not disappointed about it being a setback. — BrianPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Automation Guides Carthook Flywheel Hosting MicroConf Growth ProcessKit Tiny Seed Fund As always, thanks for tuning in. Head here to leave a  review in iTunes.    

With the year winding down we are feeling reflective during this episode of Bootstrapped Web. Jordan compares the state of Carthook from last year versus this year. A lot can change in a year! Brian is in a transition period right now and is currently trying to decide what is next in his product plans. We discuss the issues that arise with a large team of people and why Brian is actively seeking a smaller team.  We also celebrate a successful Black Friday and share what we learned from this season. The business is running, I’m freed up, but I still feel stressed because I don’t have a north star. – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Our Black Friday experiences. Automation Guides have been launched, now what? Brian’s goals for the upcoming year. The factors that affect a business team size. The discipline involved when hiring for a company. When you should aggressively grow and when you should not. Why soft skills are important. Ben Horowitz’s blog post. Moving into the new year with a clear goal. An update about ProcessKit. The benefits of free tools to software developers and their customers. How Brian’s coding lessons are paying off. Last year was stressful, chaotic, we weren’t prepared, we hoped for the best…this year was almost boring. – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Automation Guides Carthook ProcessKit Peacetime CEO/Wartime CEO by Ben Horowitz As always, thanks for tuning in. Head here to leave a  review in iTunes.

We are gearing up for the holiday season here at Bootstrapped Web. Jordan has a serious talk about self-care and knowing when to step back. Brian gives an update on ProcessKit and announces a new product. Automation Guides is launching later this month. Brian explains why he decided to create this new product and his personal goals for it. We also have a discussion about how we handle “high priority accounts” and how we like to be treated as a high priority account (VIP) by other companies. I think we get really good at ignoring stress. It just becomes normal to us. — JordanPowered By the Tweet This PluginTweet This Here are today’s conversation points: Hiccups in Jordan’s office move. ProcessKit update. Jordan’s frustrating day and knowing when to take a day off. Our holiday plans. The connection between good health practices and productivity. The launch of Automation Guides. What is Automation Guides? Why Brian is launching a new product now. Brian’s plans for Automation Guides. How Carthook deals with VIPs. Brian’s experience as a VIP and his preferences. Frankly I don’t want to talk to anyone, but I do have questions and I want them answered via email. — BrianPowered By the Tweet This PluginTweet This Resources Mentioned Today: ActiveCampaign Automation Guides Bootstrapped Web Carthook Drip MemberPress ProcessKit As always, thanks for tuning in. Head here to leave a  review in iTunes.

Ben Orenstein, is the co-host of The Art of Product podcast, a show where Brian recently appeared. Ben also tells us about his most recent project, Tuple, a tool for remote pair programming. We discuss where the idea for Tuple came from and the team who is bringing it to launch. Ben tells us about his time with ThoughtBot and what it taught him about customer relations. We also let Ben bounce some questions off of us and we give him our honest opinion of his approach and how we would personally handle it. We dive back into the discussion about funds. The latest fund to come out is Earnest Capital. Ben gives his own view on the option during our bootstrapped versus venture capital debate. I feel like this community has become really good at vetting and validating and doing things the right way. – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Welcome, Ben Orenstein. What is Tuple? The 3-man team who is designing Tuple. How Ben and his team are re-creating Screenhero. The pricing model Ben is currently using for the Tuple. What Ben learned during his time at ThoughtBot. How American business dynamic is different from an international business. Our marketing advice for Ben. The importance of relationship building in sales. Earnest Capital and what we think about it. I want to make our company more Israeli, because in Israel where I’m from argument is a form of conversation. – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Ben Orenstein’s website Ben Orenstein on Twitter Brian Casel’s website Carthook Pipedrive Salesforce ThoughtBot Tuple The Art of Product As always, thanks for tuning in. Head here to leave a review in iTunes.