Bootstrapped Web

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.

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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 money
• Coping with distractions and getting back on track.
• The 4 lessons Jordan learned from a potential acquisition.

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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.

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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.

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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.

Here are today’s conversation points:

• Big Snow Tiny Conf
• Hiring sales people in Jordan’s company
• Mapping out the existing hiring process
• The sales roles within Jordan’s company
• The problem with too many signups
• What Jordan learned this week from two customer interactions
• Unhealthy tension vs. healthy tension
• Defining top-of-funnel rules
• Future plans for Sunrise KPI
• Update on current Sunrise KPI numbers
• Shifting Sunrise KPI to a side project
• Valuing side projects
• Update on ProcessKit
• Recording customer calls
• What to ask customers about
• WOCAS Lunches

Resources Mentioned Today:

Big Snow Tiny Conf

Sunrise KPI

ProcessKit

From Bubble to Bubble

Gumroad

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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.

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.

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!

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.

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.

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.

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.

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!

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.

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.

Resources Mentioned Today:

Automation Guides

Carthook

ProcessKit

Peacetime CEO/Wartime CEO by Ben Horowitz

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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.

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.

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.

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.

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.