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

2017 has been a phenomenal year for Jordan and Brian. On today’s episode, they give the audience an update on the businesses and offer a glimpse into their plans for 2018. Brian is going to shift focus to Productize and relaunch a bigger and better product later. This means he will be closing enrollment in the course and beginning the maintenance phase of this upgrade. He shares how he reached this decision and why he is excited by the new possibilities it can bring. Jordan is adjusting to a growing business and finding ways to restructure his processes to make Carthook more efficient. He uses his previous experience over the last year to prepare Brian for his up-coming wild ride. The guys also share some new tools and resources that have found to make this new stage in their businesses a little easier. This has been the biggest spike in revenue for Productize and way beyond expectations. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Brian’s shift to working on Productize during the month of December. Jordan’s look back over his year, from an investor’s point of view. Coping with a larger team and the issues that arise. Brian’s awesome Black Friday! Brian’s plans for relaunching Productize. Jordan’s new team members and the importance of good content writing. How Jordan is restructuring his processes. The trade-offs a team has to make for the sake of speed. How to build a great product without slowing down the project. It’s still a mindset and a process, if everything is a trade-off, where are you putting the emphasis? – Jordan Powered By the

Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move the business to the next stage. Carthook is also growing their team and there have been some growing pains in the communication process. There have been some hard lessons in the process that Jordan hints at that could help business owners build their systems more effectively. Brian has been putting a lot of energy and time into Ops Calendar. He is getting a lot of interest in the service and the product. This new interest has given him a reason to ask the question if freemium is a viable option for Audience Ops. There is some really useful and thoughtful discussion in today’s episode, so tune in to join the conversation. I feel freemium is one of these things that a lot of bootstrappers have not given a fair shake as a strategy. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: The “fattening up” process of Carthook. The struggles of building an effective team. Audience Ops and Ops Calendar progress reports. Ops Calendar’s features and fixing the unexpected bugs. The usefulness of Slack. The benefits of letting  people “win.” Working with freelancers and building a positive business culture around them. Jordan’s marketing experiments and the results. The pros and cons of freemium. I admire people who are super product focused because I think it’s fun. It’s so creative and interesting. – Jordan

We have both reached a turning point in our marketing campaigns. Jordan has launched a new marketing funnel for Carthook’s Shopify tool. Brian has been running a new marketing campaign for Ops Calendar. We share how the campaigns are working for us and offer each other advice on how to improve our strategies. We also discuss how we keep our team culture positive when we ourselves are super busy and can’t give our undivided attention to individual projects. Our teams are growing and changing and we explore how we are coping with these mostly positive developments. It’s a good time for both Ops Calendar and Carthook! These calls are dripping in, inbound, organically…these just feel like good signs to me. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Carthook’s new paid marketing campaign. Ops Calendar is finding a new audience and why Brian is excited by this. How Brian uses and makes sense of Audience Ops’ analytics and metrics. How Jordan set up his marketing campaign. Jordan’s 3 blog post marketing strategy. Other insights into email and ad marketing. How we differ in our methods of team building and encouraging positive company culture. I tell people on my team think like an owner, think what do I need to fix this – Jordan Powered By the Tweet This Plugin Tweet

Today on Bootstrapped Web Jordan and Brian discuss what’s going on in their individual businesses. Brian is setting up Ops Calendar and takes today’s episode as a chance to get Jordan’s feedback from the customer’s point of view. Listeners who are interested in Ops Calendar can get excited because Brian gives a detailed description of what his service offers. Jordan has had some problems with retaining new team members. He shares what he has learned about the hiring process and how he keeps company morale high. He also shares a new service he has found for businesses who hire team members in different states and he is psyched by his results. All your employees, there is a level of trust… it’s better for everyone to be honest. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: The benefits of providing hardware and tools to your remote team members. The role trust plays in working with a remote team. Ops Calendar is going live! Jordan’s advice to Brian regarding Ops Calendar’s structure. What Ops Calendar can do for each tier. Why a business should always be recruiting. The importance of staying positive when business isn’t going as expected. How much transparency is too much? Why the service Officeengine is awesome! Having full-time employees, especially in different states, adds a massive layer of complexity. – Brian Powered By the Tweet This Plugin

Welcome back to Bootstrapped Web! We took a bit of hiatus this summer but we have some great updates and insights to share from our time away. Jordan has grown his team from 4 to 11 people. He shares how the change has impacted how they do business and work internally. Brian has finally taken a full step back from Audience Ops and can now focus on Ops Calendar. He gives the audience an update on his progress and why he thinks he should have backed off sooner. We also discuss Big Snow Tiny Conf and the changes the startup world has had to adjust to with the current state of the financial sector. We have some really deep conversation about what it means to run a SaaS business during this episode, so tune in. It’s great to be back!   The whole concept of bootstrapping is you have to make this product sustainable over time. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Our vacation times. Big Snow Tiny Conf. Jordan’s bigger and better team. The benefits of having a “marketing manager.” Brian’s step back from Audience Ops, and why he wishes he did it sooner. The update on Ops Calendar. The reality of running a SaaS business. How the financial choices for startups have gotten a lot grayer over time. If you are interested in Big Snow Tiny Conf, there is a link below. As usually there will be two events in 2018. The Sugarbush Mountain, Vermont conference will be January 22-25 and the Beaver Creek, Colorado conference will February 5-8. To get tickets to these events you need to be a part of the email list so check out the link to get your name on our list. We’re feeling the effects of the number of people on the team. Now each person’s plate isn’t overflowing. – Jordan

We cover a lot in this episode of Bootstrapped Web. We give our listeners an update on both companies’ progress and we discuss some exciting news in the startup world. Brian shares some of the goals he has for Audience Ops in the near future. Jordan has an awesome story to share about his new VIP client.  We compare our business needs and consider the unexpected problems that come with growth. We also discuss two really insightful articles that just came out, Amazon’s New Customer, by Ben Thompson and Why I Bought Your Software by Justin Jackson. Both articles are great reads and we have some good takeaways from them. If it’s not 100% core to what we do, first option will be to integrate with the big player in the field. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Jordan’s new VIP customer. Ben Thompson’s latest article. The Amazon and Whole Foods merger. Why the merger is a good thing. Lessons Jordan has learned from his new hire. The benefits of mastermind groups. The biggest expense for any growing company. How do you know when you’ve reached “feature completeness?” Brian’s Ops Calendar update. Justin Jackson’s latest article. Seeking Wisdom with David Cancel. I feel like, if you’re not in such a cut-throat, competitive space, you can get

Happily, our client loads are increasing, but our staffs are starting to feel the increased workload. So, we need to hire more people to keep up. It’s a good problem to have. On today’s episode, we compare our staffing needs and discuss how we are trying to build a process that frees us both up for “CEO tasks.”  As our businesses grow, our roles change. Brian shares his plans to cope with a couple of team members exiting the company. While Jordan recently spent some time away with his family. He shares how that trip changed how he looks at his team and responsibilities to the company. I have to perform better as a CEO…the interference portion of my equation is just preposterous. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: The uptake in business for Audience Ops. Brian’s plan to cope with the increased workload. Filling team positions for growth at Audience Ops. The ups and downs of working with a remote team. Jordan’s recent trip to New York. The “performance equation:” performance= potential – interference. How the performance equation has helped Jordan look at Carthook’s growth differently. How difficult it can be to transition into the “CEO role.” Forget limiting the headcount, let’s get more than enough people on board and spread the work around. – Brian Powered By the Tweet This Plugin

Today Brian and Jordan discuss growth. In Jordan’s case he is dealing with sudden growth, and in Brian’s case, he is planning for growth. Both share how they are handling this wonderful problem. Jordan has been focused on getting Carthook’s marketing up and running again, but it has become clear that his team needs him to focus on improving the customer support. It has been a struggle to really pinpoint what the team needs. Jordan calls it “customer success,”  but Brian isn’t so sure that’s the best title for the position. Brian is working on his KPI (Key Performance Indicators.) While making the dashboard for these KPI, he learned that sometimes you need to just hire someone. Brian is also planning to do some hiring, he needs two project managers and a writer. He caps off today’s topics with an article from the website Baremetrics. I’m now in this mindset with this business, it is all about growth. – Brian Powered By the Tweet This Plugin Tweet This Here are the conversation points: Brian’s four major categories for his KPI. When to know you need to hire someone. Jordan’s ever-growing stress. Jordan’s undefinable job description. What does “customer success” mean? What Jordan needs for this new position. The importance of taking care of “home base.” Brian’s hiring needs. Josh Pigford’s blog post. What we need to do is work harder and smarter on making sure existing customers are satisfied and happy. – Jordan Powered By the Tweet This Plugin

We are both hitting some major growth right now in our businesses, and that means a lot of excitement and a lot of restructuring. We talk about project managing, hiring the right people, and the efforts we are putting into our marketing and lead generation. Jordan recently went to Europe and met up with his team. He tells us how the trip went and the exciting milestone he saw while working with the Carthook team in Europe.  Jordan has also had some people leave the company. He explains why they had to go and how he plans to bounce back. Carthook’s marketing has stalled because of a sudden flux of customers, Jordan discusses his concerns and how he plans to fix the problem. Brian has really sunk into his Facebook ad campaign. He is working to generate leads for Audience Ops and filter people into a funnel that will lead potential clients to a consultation. He explains the 3 step ad campaign and shares how it is working for him. Brian is also hiring some new people and offers some advice for Jordan regarding his marketing problems. We only have a certain number of bullets to fire, in terms of people we can have inside the company. – Jordan Powered By the Tweet This Plugin Tweet This Here are our conversation points: Jordan’s trip to Europe. Brian’s Facebook ad campaign. Brian’s current hiring needs. How to create evergreen content for lead generation. Jordan’s concern about customer support quality. The “2 worlds” of Carthook. Why Trello isn’t working for Jordan and his team. How to discern what is urgent in your business. What are the expectations of a Project Manager? The difficulties of firing team members. Brian’s podcast relaunch. The 3 phases of online software. How to build a brand online.

We are back discussing our businesses and the progress that we have been making. On the personal front Jordan is heading off to Europe and Slovenia to work and hit the beach. Brian has been getting healthier with the BulletProof diet. Brian has been recording new episodes for his Productized podcast. He is hiring one person to take care of the editing, shownotes, social stuff, and posting. He is also trying to make two videos a week. He is also launching the Sell to Strangers webinar for his funnel. Jordan plans to get a lot of work done in Slovenia including writing a script for a webinar. He also wants to finish up the documentation for product including video. Jordan feels that he needs to go a little harder on his marketing and create more desire. If you want to grow your business, you have to sell to strangers. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Brians Productized podcast and his video progress. Jordans list of things he wants to do for his business while in Slovenia. Writing scripts for webinars. Making a public calendar or roadmap to help hold yourself accountable. Education for products has two parts – how to use the product, and how to get the most out of using it. Using webinars for funnel content. How Click Funnels grew off the back of one webinar Steal My $17,000 a Day Funnel. Case studies and client interviews and the wins possible. Marketing to marketers for Jordan’s business. The project manager side of Audience Ops. Breaking down processes and putting the right people in the right positions.

We are back from MicroConf and on this episode we share our takeaways and also update the important things going on in our businesses. Jordan shares how Russ Henneberry’s MicroConf talk encouraged him to look at his business differently. After this episode you may not look at funnels the same way again. Brian explains how MicroConf often helps him refocus his priorities. He has plans to reconnect with his personal brand and create some new engaging content. We discuss how he can do that. MicroConf has been an educational experience for both of us and we have some really good take aways that we discuss today. We also have some general updates about our businesses. Surprisingly, we both are having issues with our marketing. We compare situations and see if we have something that could be helpful to the other person. It’s been very helpful for the team to see me very freely admit shortcomings. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: How MicroConf changed Jordan’s approach to funnels. Content marketing updates. Why you should know why your customers use your product. Brian’s update about Audience Ops and Casjam. Jordan’s new hires. The importance of improving SOPs. The natural progress toward corporate structuring. Why it is inevitable. Our marketing successes and woes. It’s more about really understanding the underlying ‘why’ of that problem in your customers’ minds. – Brian Powered By the Tweet This Plugin

Today we discuss how our respective businesses have begun on-boarding customers to our new products. The Shopify checkout app is growing and Jordan and his team are learning what makes the app successful. Brian has begun on-boarding clients on to the Audience Ops Calendar. We discuss what we’re learning from these processes and how that will change how we move forward. Microconf Vegas is just around the corner. Jordan will be giving a talk to the event. He shares what has inspired his talk. Even if I know what I’m focused on this quarter, things tend to change when I leave MicroConf. – Brian Powered By the Tweet This Plugin Tweet This   Some of the other things we discussed in today’s episode are: Lessons Jordan’s team has learned from Hiten Shah’s course. Should a customer support employee be full time? Why SaaS is so competitive. Why you can’t please everybody. The upcoming Microconf Vegas. Why Brian shut down Audience Ops Express. You need like a north star of what your product does or it’s easy to get pulled in different directions. – Jordan Powered By the Tweet This Plugin Tweet This Resources Mentioned Today:

We have some big news coming up the following weeks. Brian discussed his recent experience with Facebook ads and the pros and cons of marketing on the platform. Jordan shares his found  his new found security in his business. We are really excited about the new rewrites and product launches and we talk about it all! Marketing needs to make that promise and then the product needs to deliver on that promise. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Brian’s Facebook ads and the results. Jordan’s new confidence in Carthook. Tweaking the Calendar app for beta testers. Brian’s new service Audience Ops Express. The reasons people leave Audience Ops. How Audience Ops Express would change those reasons. Carthook’s new release. How to move into a self serve business model. Audience Op’s Calendar gets a new name. Gearing up for Microconf. Las Vegas. We’ll do all the extra leg work to get it proofread, polished… whatever needs to happen. – Brian Powered By the Tweet This Plugin Tweet This

Welcome back to Bootstrapped Web. On today’s episode we cover a lot of subjects that are both business and personal nature. We update you on Brian’s Calendar product and Jordan tells us about a talk he gave to his accelerator group. We also discuss Brian’s experience with Facebook ads and how Facebook is helping him get the word out about Audience Ops. He shares some tools he has found useful  while creating these ads. If you are looking for some easy to use tools for your ads you might find this episode interesting. For now the goal is to drive more leads through a funnel for the content service and keep that engine turning.- Brian Powered By the Tweet This Plugin Tweet This Here are our conversation points: Jordan’s talk with Portland’s Starve Ups. How Brian uses Facebook ads to promote Audience Ops. What is a Facebook lead ad? Creating ad campaigns with Facebook. Jordan’s problems with Facebook Pixel. Our discussion about public school and it’s lack of individuality. Brian’s update on the calendar project. Why working with people in person is useful. We have become the default recovery app for subscription businesses. We own that market. – Jordan Powered By the Tweet This Plugin

We talk about Big Snow Tiny Conf and team growth today. Brian had a great time up at Vermont’s Big Snow Tiny Conf and has some awesome take-a-ways to share. Jordan is growing his team and is getting ready for a big marketing push. We both have some useful insights into team management and creating a successful product funnel. This is a good episode to see what goes into a product launch and how a project has several launches. It’s amazing that something that you hate and weighs on you, just get it done and everything feels better. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Big Snow Tiny Conf Kara Swisher on Tim Ferriss’ podcast. Tax season for Startups. Jordan’s new developer. Ways to structure team management. Josh Pigford’s latest blog post. Why we stopped consuming business advice. When we consume new business advice. Brian’s new developer. The benefits of hiring new team members. Brian’s advice for marketing to Jordan. Jordan’s Stave Ups talk. Frankly, I don’t think there are enough podcasts that are using the model we’re using here. – Brian Powered By the Tweet This Plugin