More Questions Than Answers in 2019

More Questions Than Answers in 2019

 
 
00:00 / 00:47:44
 
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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.

Team Equity / A New App / The Next App

Team Equity / A New App / The Next App

 
 
00:00 / 00:38:33
 
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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.

 

 

Surviving & Thriving Through Black Friday / Building an App in a Week

Surviving & Thriving Through Black Friday / Building an App in a Week

 
 
00:00 / 00:39:45
 
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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

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

Launching a New Product in a Month / VIP Customer Sales

Launching a New Product in a Month / VIP Customer Sales

 
 
00:00 / 00:49:55
 
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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 Joins us to Talk Bootstrapping

Ben Orenstein Joins us to Talk Bootstrapping

 
 
00:00 / 00:52:40
 
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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.

Building in Public / Case Study Marketing / TinySeed

Building in Public / Case Study Marketing / TinySeed

 
 
00:00 / 00:45:30
 
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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.

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.

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.

Bootstrapping Reality / Technical cofounders / New Management

Bootstrapping Reality / Technical cofounders / New Management

 
 
00:00 / 00:53:48
 
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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.

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.

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.

ProcessKit Early Access / Celebrating Growth / CTO Questions

ProcessKit Early Access / Celebrating Growth / CTO Questions

 
 
00:00 / 00:57:01
 
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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.

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.

Resources Mentioned Today:

Carthook

CaboPress

Lambda School

Ops Calendar

ProcessKit

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

Conference Hopping / Hiring Mistakes / Busting Growth Plateaus

Conference Hopping / Hiring Mistakes / Busting Growth Plateaus

 
 
00:00 / 00:41:17
 
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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!

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.

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.

 

 

Value of a Coach / Hiring Spree / Launching in Public

Value of a Coach / Hiring Spree / Launching in Public

 
 
00:00 / 00:51:56
 
1X
 

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.

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.

Resources Mentioned Today:

Audience Ops

Carthook

Derrick Reimer’s Twitter

Jordangal.com

Jordan’s email

Jordan’s Twitter

Level

Level on Twitter

MicroConf

Productize

Slack

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