Bootstrapped Web

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 today’s conversation points:

• Email and newsletter issues (Convert Kit, MailChimp, Priority sorting via Gmail)
• Hosting options for a static site or marketing sites
• Web design and developing rabbit holes
• Calculating successes
• Updates with the CartHook app store
• Various hiring options for developers
• Brian’s new developer
• Podcasting subscriptions
• What we’d like to see in podcasts

Resources Mentioned:

Process Kit

Carthook.com 

Convert Kit

MailChimp 

WordPress

Jekyll

Gatsby

Hugo

Netlify

Upwork

We Work Remotely

Blue Coding

Andrew Wilkinson on Twitter

Metalab

Productize Podcast

How I Built This Podcast

The Art of Product Podcast

Build Your SaaS Podcast

Slow and Steady Podcast

Out of Beta Podcast

The SaaS Reality Podcast

Business Time Podcast

Rogue Startups Podcast

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

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 process (removing the self-serve free trials and requiring demos instead) which forced us to reprioritizing features
• ProcessKit’s new custom fields and how that got everyone’s attention
• The mental/emotional roller coaster of price changes
• Timing and focus on multiple projects
• The Sunrise vision
• When should you grandfather someone in?
• The benefit of the dual-track development & outsourcing
• The sunk cost fallacy
• An update on Brian’s search for a developer

Resources Mentioned:

Process Kit

Sunrise KPI 

Carthook.com 

Product Hunt 

Shape Up 

Goodreads: Shape Up 

Basecamp 

Codementor 

Upwork 

Audience Ops 

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

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, and what I’m looking for in a web designer.

Here are today’s conversation points:

• The future of the podcast, and the regularity of posts
• How podcasting helps people stay in touch
• What is Tuple, who is it for, and what’s next for Tuple?
• What does it mean to launch? What is the value of the beta phase?
• Is a manifesto site like a launch? How you can have a “splashy” launch
• We talk about how to use ProductHunt well and if it really works
• We debate on how a website can keep up with the changes with a product launch
• I talk about a web developer and if it’ll help bust through road blocks, my ideal picture, and the worry with outsourcing tasks
• What I’m looking for in a web developer
• Ben talks about the best way to get better at programming
• What is the strategy for Tuple and ProcessKit, post-launch

Resources Mentioned Today:

Ben Orenstein

The Art of Product Podcast

Tuple

Product Hunt

ProcessKit Roadmap

Codementor

Audience Ops

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

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. 

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.

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.

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.

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.

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.

Resources Mentioned Today:

Carthook

Productize

ProcessKit

WP Elevation

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

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.

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.

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.

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.

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

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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.

Here are today’s conversation points:

• Our MicroConf experience and takeaways.
• What are Tick Tock projects?
• Carthook’s Portland Mastermind
• Brian’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.

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?

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

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Resources Mentioned Today:


Audience Ops

Carthook

MicroConf

ProcessKit


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