Bootstrapped Web

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

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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.

I talk about all these things that are really common themes in struggles that a lot of entrepreneurs face. – Sherry

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Resources Mentioned Today:

Big Snow Tiny Conf.

Drip

The Entrepreneur’s Guide to Keeping Your S**t Together

Zen Founder

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

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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.

The timeline of building anything is longer than it seems, it’s messier and that’s the core of frustration. – Brian

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Resources Mentioned Today:

Audience Ops

Carthook.com

Casjam.com

Growth Hacking is Manipulation by Josh Pigford

Lifterlms

Ops Calendar

Productize Course

Productizeandscale.com

Restrict Content Pro

Salesmachine

The Greatest Sales Pitch I’ve Seen All Year by Andy Raskin

As always, thanks for tuning in. Head here to leave a  review on iTunes.

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

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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

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Resources Mentioned:

Audience Ops

CasJam

Carthook

Ops Calendar

Productize

As always, thanks for tuning in. Head here to leave a  review on iTunes.

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

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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

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Resources Mentioned Today:

Appcues

Audience Ops

Beacon

Carthook

Drift Seeking Wisdom Podcast

GoVideo

Productize Course

Ops Calendar

Soapbox

As always, thanks for tuning in. Head here to leave a review on iTunes.

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

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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

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Resources Mentioned Today:

Audience Ops Calendar

Carthook

As always, thanks for tuning in. Head here to leave a review on iTunes.

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

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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

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Resources Mentioned Today:

Audience Ops

Carthook

Ops Calendar

As always, thanks for tuning in. Head here to leave a  review in iTunes.

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

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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

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Resources Mentioned Today:

Audience Ops

Big Snow Tiny Conf

Carthook

Ops Calendar

Runway

As always, thanks for tuning in. Head here to leave a review in iTunes.

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

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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 by with a slower road map. – Brian

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Resources Mentioned Today:

Amazon’s New Customer, by Ben Thompson

Audience Ops

Carthook

Drift

Front App

Intercom

Ops Calendar

Seeking Wisdom

Why I Bought Your Software, by Justin Jackson

As always, thanks for tuning in. Head here to leave a  review in iTunes.

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

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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

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Resources Mentioned Today:

Audience Ops

Carthook

Productize

As always, thanks for tuning in. Head here to leave a  review in iTunes.