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

We have some exciting updates to share and we give our reaction to Rob Walling and Einar Vollset’s big announcement of the TinySeed Fund. Jordan and his team are preparing to move offices in Slovenia. He also sings the praises of case studies. Carthook has been working with Case Study Buddy and Jordan is very pleased with the results. He shares some of those strategies and explains how they are working for the company. Brian is publically building ProcessKit but he’s hit a lull in his information sharing. We talk about the pros and cons of building in public and how it is hard to know what is worth sharing with your mailing list. Brian has also written a how-to article about tiny confs, he explains why he wrote it and the response he’s had from it. We wrap up today’s episode with TinySeed Fund. We explore who would benefit from this fund and why it is so exciting for the bootstrapping community. It is a wonderful idea with potential and we discuss that potential. I think most bootstrappers aren’t going for a lifestyle business. – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Brian’s CaboPress trip. How to organize a tiny conf. Building ProcessKit and how Brian is interacting with his mailing list. Finding the right balance between marketing and product design. When to go on defense or offense. How case studies are working for Carthook’s growth. How authenticity and quality draw an audience. TinySeed Fund and what it means for the bootstrapping community. Don’t wait to find someone before making progress. The more progress the better, always – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops CaboPress Carthook Case Study Buddy How to Host or Attend a “Tiny” Conference Know Your Company ProcessKit The Art of Podcast 58: Evolving Roles as a Startup Founder TinySeed Fund As always, thanks for tuning in. Head here to leave a  review in iTunes.

Today’s episode is a straightforward update episode for us. Brian is moving forward with ProcessKit and reflects on his goals for the project. Jordan celebrates the awesome team he has built over at Carthook and shares what it is like to step back and see the machine run. We have been traveling for various reasons. Brian has just came back from Martha’s Vineyard and he shares some of the takeaways he took away from that conference. Jordan visited his Slovenia team recently and has some exciting growth to share.  We discuss the benefits of conferences and why we enjoy them. Brian has some experience with Big Snow Tiny Conf, so he weighs in on it from the organizer’s prospective. We talk about the work of Justin Jackson and all the good he is doing for the bootstrapped community. Owning your own business is tough and it isn’t glamorous. We talk about how bootstrapping has changed and how parts of it will always stay the same. I still believe that bootstrapping and self-funding and stair-stepping is very much still possible. – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Our latest travel stories. Brian’s time in Martha’s Vineyard. What it is like to plan mini-conferences. An update on ProcessKit. What Brian is looking for in a business partner. The decisions Brian made during Martha’s Vineyard. Jordan’s trip to Slovenia. Carthook’s success. How Carthook’s new development system is building a roadmap for customers. Justin Jackson’s work and what it is doing for the bootstrapped community. The romanticizing of bootstrapping and venture capital avenues. The ups and downs of owning a business. I’ve caught myself in moments of reflection, with a smile on my face, I’m like, you need to enjoy this. – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Big Snow Tiny Conf. CaboPress Carthook MicroConf ProcessKit TMBA 460: Are We Being Honest About the True Cost of Bootstrapping a Business? As always, thanks for tuning in. Head here to leave a  review in iTunes.

We are back to tell you about some exciting news and developments. Jordan is enjoying a high mark in Carthook’s business and he found a building so he can move his Portland team. He also discusses the marketing strategies and changes that are making Carthook just soar. Brian is announcing his new product, ProcessKit. It is the next evolution of Ops Calendar and is designed to help business teams keep all their SOPs, workflow, and schedule all in one place. The hope is to increase efficiency and offer a process innovation tool. Brian also dives into the change of approach he is taking with ProcessKit. When Ops Calendar was launched there were a lot of things that taught Brian how to do it better. On today’s episode, he explores those lessons. It’s not ‘build it, they will come,’ it’s if you build it well, they will find out about you. – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Welcome back to Bootstrapped Web! Jordan’s long distance traveling and plans for more travel. Introducing ProcessKit What ProcessKit does and the problem it fixes. Carthook has grown by 75%. What makes Carthook version 2 different? How Jordan plans to unlock more growth. Lessons learned from the Ops Calendar launch. The type of people responding to Brian’s new approach. Jordan’s change in content and marketing strategy. How feedback is helping Brian “get out of his own head.” The end of Jordan’s office space search. Austin Alred’s new startup that has Jordan really excited. Teams don’t think twice about paying for tools if it helps them be productive. – Brian Powered By the Tweet This PluginTweet This Resources Mentioned Today: Carthook CaboPress Lambda School Ops Calendar ProcessKit As always, thanks for tuning in. Head here to leave a  review in iTunes.

Summer is in full swing and we are back from our individual vacations. We discuss our businesses and our personal roadmaps for Carthook and Audience Ops. We vent about developing frustrations and we do an armchair quarterbacking session for ConvertKit’s new branding strategy. Brian updates the audience on his coding education adventure. Jordan shares his experience with Stripe and their partner program. He also discusses a new website and funnel design he is exploring the Carthook team. Tune in for today’s episode about coding, branding, and moving in new directions. Processing revenue gives you power. If I were ConvertKit, that’s the direction I’d go. – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Why Brian hasn’t set any goals for this year. Jordan’s frustrations about feature development. The new roadmap for Ops Calendar. Brian’s coding lessons and what he has learned. The difference between Rails and Laravel. Why Brian switched back to Rails. PHP vs. Rails and what it tells you about the business. Jordan’s feedback for Stripe. Armchair quarterbacking for Nathan Berry’s Seva. Carthook’s new branding strategy. Our mutual need for an educational product. I found that Rails is just easier for me to learn and easier and faster to get an app up and running. – Brian Powered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Carthook ConvertKit Laravel Productize & Scale Practicing Rails by Justin Weiss One Month Stripe As always, thanks for tuning in. Head here to leave a  review in iTunes.

It is summertime! We have some great travel plans in the works, but before we pack our bags we want to celebrate the small victories we have seen in our businesses. Audience Ops podcasting is really starting to take off. Brian rehashes the road he took to get to this point and where he hopes it will to in future. He also updates the audience on Productize and shares some feedback he is putting to good use. Jordan is experiencing some wild growth and is ready to ride this wave to wherever it might go. He shares a lesson about opening up decisions to the whole office and why it isn’t always a good idea. It’s going to be a great summer! Tune in and join us! It used to be that the development was our bottleneck, we fixed that to such a degree that it’s humming. – JordanPowered By the Tweet This PluginTweet This Here are today’s conversation points: Jordan and Brian discuss their summer travel plans. Travel tips Brian learned from a guest on his podcast. Jordan’s disappointing decision and why he decided the way he did. An update on the Audience Ops podcasting service. The difference between the blogging service and the podcasting service. Carthook’s recent boost in activity. Why Jordan’s new process is so successful and there is a boost. What a great designer does for your product. The feedback Brian is getting regarding his Productize funnel and how it has improved. Why Brian doesn’t offer a payment plan. Jordan’s coaching update. Our struggles with diet and fitness. Brian’s Laravel update. Audience Ops, in general, is still really stable. It feels good this year. – BrianPowered By the Tweet This PluginTweet This Resources Mentioned Today: Audience Ops Audience Ops Podcasting Service Carthook LaraCast Productize Productize Podcast As always, thanks for tuning in. Head here to leave a  review in iTunes.

It has been three weeks of constant travel for us. We have been jetting around to tons of industry conferences. It has been a hectic and educational time for both of us. We share some of our takeaways from the conferences and really debate the value of a business conference. What gives a conference its value? We also  give some personal updates. Brian talks about his fitness routine a bit and Jordan is starting to notice changes in his company’s efficiency. Brian updates the audience on the new podcast service and some of the growing pains coming out of it. All and all there is a lot going on right now in Carthook and Audience Ops! When you are scaling a service, you’ve got to have processes so bulletproof, that they won’t break down. – BrianPowered By the Tweet This PluginTweet This Here are today’s conversation points: Why small conferences are more valuable than larger ones. Why go to MicroConf? Getting ready for more upcoming conferences. How Jordan and Brian get value out of a conference. Brian’s daily exercise routine. Jordan’s first coaching client. Managing by walking around, what is it? The Owner’s Word Weighs a Ton, by Jason Fried. Communicating effectively with a team. Jordan’s lessons from MicroConf. Brian’s podcast service update. The challenges of hiring the right person. How to combat lack of interest in a team. I ignore trying to pull value from a conference. Insight I get from where everyone is, that’s the value. – JordanPowered By the Tweet This PluginTweet This Resources Mentioned Today: The Owner’s Word Weighs a Ton, by Jason Fried. MicroConf Big Snow Tiny Conf CaboPress Unite 2018 Consensus 2018 Audience Ops Carthook As always, thanks for tuning in. Head here to leave a  review on iTunes.    

On today’s episode, we discuss the real value of a business coach. Jordan has announced that he would like to try his hand at it and Brian shares his own experience with it. We compare the pros and cons of being a coach for other founders and we explore why it is a good revenue source. We also continue our Armchair Quarterbacking Sessions with Derrick Reimer’s project Level. Derrick has noticed some productivity issues with the platform, Slack. He is out to recreate an alternative that can be customized for the tech world, where distractions are project killers. We offer our impressions of the idea and analyze how Derrick is approaching his product development. There are so many really talented, really smart, really motivated people, they just want to work remotely. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Getting ready for MicroConf. Brian’s update on the podcasting service. The only stumbling block Brian has encountered. Jordan’s plans to start coaching. Why he is interested in exploring coaching. Who would benefit from Jordan’s coaching? The value of a good business coach. The pros and cons of being a coach. Armchair Quarterbacking Session: Level. Building an alternative to Slack, and is it possible? Are there any benefits to being transparent? Jordan’s advice to Derrick. Brian’s impressions of Derrick’s idea. If you are going to provide value, it’s not just talking, it’s work. –

Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are starting with Andrew Culver’s SaaS product, Bullet Train. We also give general updates on what is going with Carthook and Audience Ops. So tune in to hear about Brian’s new service and Jordan’s newfound ambition after having a rare full team meetup. We [founders] think in a certain way and maybe we don’t remember what it is like to be an employee. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: How having Rok and Ben around has energized Carthook’s team. The presentations and social activities that helped Jordan’s team get better in step with each other. Adjusting back to regular business after Rok and Ben left. Brian’s new podcasting service. The hiring process Brian is using to build his podcast service. An update on the Productize Course and Brian’s closed cart approach. Jordan’s upcoming conference projects. The struggle of working during business travel. The benefit of doing one-on-one discussions with your employees. The first armchair quarterbacking session: Bullet Train. Why agencies would be the best fit for Bullet Train. Nobody is going to get as fired up and keep pushing than the founder. – Brian Powered By the Tweet This Plugin

We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service. Ben Fisher is the co-founder of Carthook and head of product. Rok Knez is Carthook’s lead developer. He usually manages the company office over in Slovenia. Both Ben and Rok were a part of the company since the very beginning. The guys share how they met and how the business has gone from 3 guys hanging out to the large-scale team that is today’s Carthook. We discuss the technical issues that have reared their ugly head the last few months and Ben explains how they coped with this inevitable part of the business. Today the hood is being lifted on Carthook and we will learn about how Jordan and his team interact with each other and their clients. Buckle up for a very technical episode! For bootstrapping new software startups, choose a more mature framework, rather than the trendiest stuff. – Brian Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Introducing Ben and Rok. How Ben and Rok met Jordan and got involved in Carthook. How Rok hired the engineering team. Who helps with product design? The new style guide the team has recently adopted. How Carthook’s tech stack has evolved. The importance of not cutting corners. The benefits of using Angular. Carthook’s road-mapping process. When do frameworks and processes matter? The 3 questions the team ask themselves when making decisions. How Hiten Shah has influenced Carthook’s process. How Jordan and the original team have coped with working with a larger team. W

MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working properly and Jordan and his team are seeing some major cultural shifts in the business. Brian has found himself with some downtime, so now he is thinking about new avenues for Audience Ops. Brian outlines his idea for a new service offered through Audience Ops. An done-for-you podcasting service. He gets Jordan’s feedback and really explores why he thinks podcasts are the next logical step for the business. He also drops a big announcement… Brian wants to learn to code. We have some interesting conversation about alternative content on this episode and some really useful reflections on the founder’s role within his company. If somebody asked the most valuable thing you’ve learned the past months it would be related to our process. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Get ready for MicroConf. Brian’s new service launch. Considerations for future podcast topics. Jordan’s March recap. Why Brian wants to launch a new service. The all-done-for-you podcast service breakdown. Brian’s small beta group for the new service and the results. The benefits of podcasting content. The second version of Carthook update. Jordan’s webinar experiment. The benefits of webinars. How to create pitch-hitter scenarios. How Carthook uses paid ads. The ad strategy Jordan used for the webinar.

It has been a crazy couple of weeks for both of us. We took a break last week, but we are back and we’ve got some great topics! Jordan spent all of last week fixing a product issue. It was hard, it was frustrating, and it showed him just how great his team could be. He explains what happened to Carthook and how the problem was resolved. Brian is performing an experiment with his Productize course. He is reaching out to a cold audience. He shares why he felt this was the way to go and lays out how he plans to attract new customers as this experiment progresses. Join us today as we discuss the reality of customer service. We talk about the importance of meeting customer expectations and doing it with a smile. We also dig into how to go about finding those customer expectations when they aren’t that obvious. Once some people are successful, it feels like everything they do is successful because of the build up. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Brian’s webinar experiment. Jordan’s frustrating week and how he and his team coped. How price point affects a customer’s expectations. The Productize webinar ad strategy. How to make data work for you in an experiment. Brian’s results thus far in his experiment. How to cope with doubt in your service. When to decide to push or pivot. How to help customers find solutions. It’s not always the grass is greener for those looking to transition from one model to a different model. – Brian Powered By the

We are back to discuss the exciting and frustrating things going on with our businesses. Jordan has a lot on his plate including launching 15-20 new features and a few industry conferences; he will be attending the Traffic and Conversion Summit in San Diego, as well as, speaking at MicroConf Growth in Las Vegas. Brian of course also has a lot coming down the pipeline. He gives the audience an update on his new direction for the Productize course and the webinars he is producing on his site. The theme for today’s episode is customer outreach. We both compare our styles of marketing and networking and share what has worked well in the past. We also discuss the upcoming challenges we see in our companies and talk about proactive steps we can take to make the process smoother. I’m starting to see the daily benefits of having an active Slack group of members…It pays off… — Brian Casel Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Jordan’s preparation for the Traffic and Conversion Summit. Traveling for business and keeping up. Carthook’s upcoming new features and how to announce it. Tips for smart networking at conferences. Jordan’s invitation to speak at MicroConf. Brian’s laser focus on Productize. Recent feedback about Ops Calendar and how that is changing Brian’s plans. The process Jordan and his team have developed for updating Carthook’s features. The best examples of marketing a large scale update. The journey to building an online community around your product. How transparent should a business be with these communities? Brian’s yearly plan for Productize and Scale (the new name of CasJam.) The live webinar Brian is offe

Our guest today is Sherry Walling. Sherry is a clinical psychologist and the author of the soon to be released book, The Entrepreneur’s Guide to Keeping Your S**t Together. Sherry is also the co-host of the Zen Founder podcast with her husband Rob Walling, the founder of Drip. Her time with the podcast has given her an insight into the fears and concerns every entrepreneur experiences. She gives us her observation of the entrepreneurial journey and her advice to navigate it. Sherry’s book will be available February 21, 2018. Join us for this free therapy session for any stressed out bootstrapper! All of us are afraid that we’re crazy, or we’re fooling ourselves. We live in our own isolated mind. – Sherry Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: Jordan’s recent “world tour.” Brian’s time at Big Snow Tiny Conf. Welcome, Sherry Walling! Sherry’s upcoming book, The Entrepreneur’s Guide to Keeping Your S**t Together. Her professional background and marriage with Rob Walling. Why Sherry decided to write the book. The cycle of the entrepreneurial journey. How business owners build resilience. The common issues entrepreneurs share. The role of “gallows humor” in business. How to combat the negativity many entrepreneurs face. The importance of meeting other entrepreneurs. Sherry’s tips for bootstrappers to stay healthy.

Today we discuss a really heated topic that popped up on Twitter over the holiday break. A Twitter flame war was started by a post chastising business owners for not working through the holidays. We have some thoughts on the subject and we discuss the changing world social media has ushered in for bootstrapped companies. Jordan discusses some growing pains he has been experiencing with the new Carthook team. He shares some lessons he has taken away from the experience and how he is trying to find the company’s footing and optimal path for 2018. He also has some exciting news… Carthook has reached the 100 million dollar threshold! Brian is facing a major shift of focus in his company. He will now be putting his energy into the Productize Course. The course will be his flagship product. He even has plans to change his branding. He will change CasJam to Productize and Scale. He is really excited about this change and is looking forward to a new start in 2018. If you are that busy and that crazy, you’re not prioritizing well and not focusing on the right things. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s topics: The Twitter flame war over the break. How Jordan and Brian find balance in their business and personal life. Why “work guilt” is unhealthy. Jordan’s new marketing coach and what he has taught him. The cryptocurrency fad.and what it could mean for bootstrappers. What Jordan has learned from using Salesmachine. Brian’s plan for test driven development. CasJam.com will soon be Productizeandscale.com, and why Brian is making the change. Why Brian wants to build a company community in 2018. Andy Raskin’s Drift post. Josh Pigford’s latest blog post. How social media has totally changed marketing and research and development.

2017 is coming to a close and Jordan and Brian are looking back on this explosive year. They also share their plans for 2018. Audience Ops and Carthook both saw tremendous amounts of growth this year. That growth has caused the guys to reflect on 2017 and the lessons they have taken away from the experience. Brian has seen an uptake in sign-ups and Audience Ops has ridden a roller coaster this year. Brian shares what he learned from the sudden stop and go growth of the business. 2018 looks to be a major year for Audience Ops, Ops Calendar, and Productize. Jordan has had a monster of a year. He is recuperating from a breakneck year with a well deserved slow down period. Jordan shares what this year taught him about team building and how he plans to fix some of the issues he noticed during Carthook’s major growth spurt. Growth is great, but it will mask problems. – Jordan Powered By the Tweet This Plugin Tweet This Here are today’s conversation points: The problems Jordan discovered when onboarding new team members. Brian’s surge in service sign-ups. Carthook’s Drip campaign disaster. Setting new goals and themes for 2018. The downside of sudden growth. Coping with wild growth and rapid plunge of business. Jordan’s tech issue in 2017 and how he plans to fix them. Productize’s new course launch in January. Jordan’s general observations about 2017 and 2018. Brian’s general observations about 2017 and 2018. I actually have a lot of firepower to play with going into 2018 now. – Brian Powered By the Tweet This Plugin