Bootstrapped Web

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.

I feel like..both businesses and consumers has changed a lot recently. People have become more savvy. — Brian

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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.

I will be joining TinySeed as a mentor, I’ll get that frontline view of how founders are thinking. — Jordan

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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.

What matters is what’s being interacted with, not just how people are inside of our app, but the end result. — Jordan

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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!

I felt we (the partnership) were going to do good things for ProcessKit but I was not disappointed about it being a setback. — Brian

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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.

The business is running, I’m freed up, but I still feel stressed because I don’t have a north star. – Brian

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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.

Last year was stressful, chaotic, we weren’t prepared, we hoped for the best…this year was almost boring. – Jordan

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Resources Mentioned Today:

Automation Guides

Carthook

ProcessKit

Peacetime CEO/Wartime CEO by Ben Horowitz

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

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.

I think we get really good at ignoring stress. It just becomes normal to us. — Jordan

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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.

Frankly I don’t want to talk to anyone, but I do have questions and I want them answered via email. — Brian

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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.

I feel like this community has become really good at vetting and validating and doing things the right way. – Brian

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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.

I want to make our company more Israeli, because in Israel where I’m from argument is a form of conversation. – Jordan

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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.

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. – Brian

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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 – Jordan

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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. – Brian

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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. – Jordan

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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

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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

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Resources Mentioned Today:

Carthook

CaboPress

Lambda School

Ops Calendar

ProcessKit

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