Ben Orenstein Joins us to Talk Bootstrapping

Ben Orenstein Joins us to Talk Bootstrapping

 
 
00:00 / 00:52:40
 
1X
 

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
 
1X
 

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
 
1X
 

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
 
1X
 

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
 
1X
 

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.

What If We Ran Your Business (For the Fun of It)?

What If We Ran Your Business (For the Fun of It)?

 
 
00:00 / 00:48:23
 
1X
 

Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are starting with Andrew Culver’s SaaS product, Bullet Train.

We also give general updates on what is going with Carthook and Audience Ops. So tune in to hear about Brian’s new service and Jordan’s newfound ambition after having a rare full team meetup.

Here are today’s conversation points:

  • How having Rok and Ben around has energized Carthook’s team.
  • The presentations and social activities that helped Jordan’s team get better in step with each other.
  • Adjusting back to regular business after Rok and Ben left.
  • Brian’s new podcasting service.
  • The hiring process Brian is using to build his podcast service.
  • An update on the Productize Course and Brian’s closed cart approach.
  • Jordan’s upcoming conference projects.
  • The struggle of working during business travel.
  • The benefit of doing one-on-one discussions with your employees.
  • The first armchair quarterbacking session: Bullet Train.
  • Why agencies would be the best fit for Bullet Train.

Resources Mentioned Today:

Audience Ops

Bullet Train

Carthook

MicroConf.

Productize

Shopify Unite

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

The Carthook Team Talks Product Development Process

The Carthook Team Talks Product Development Process

 
 
00:00 / 00:53:46
 
1X
 

We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service.

Ben Fisher is the co-founder of Carthook and head of product.

Rok Knez is Carthook’s lead developer. He usually manages the company office over in Slovenia.

Both Ben and Rok were a part of the company since the very beginning. The guys share how they met and how the business has gone from 3 guys hanging out to the large-scale team that is today’s Carthook. We discuss the technical issues that have reared their ugly head the last few months and Ben explains how they coped with this inevitable part of the business.

Today the hood is being lifted on Carthook and we will learn about how Jordan and his team interact with each other and their clients. Buckle up for a very technical episode!

Here are today’s conversation points:

  • Introducing Ben and Rok.
  • How Ben and Rok met Jordan and got involved in Carthook.
  • How Rok hired the engineering team.
  • Who helps with product design?
  • The new style guide the team has recently adopted.
  • How Carthook’s tech stack has evolved.
  • The importance of not cutting corners.
  • The benefits of using Angular.
  • Carthook’s road-mapping process.
  • When do frameworks and processes matter?
  • The 3 questions the team ask themselves when making decisions.
  • How Hiten Shah has influenced Carthook’s process.
  • How Jordan and the original team have coped with working with a larger team.
  • What Jordan and his team have learned about their product.
  • The importance of choosing the right colleagues.

Resources Mentioned Today:

Carthook

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

Launching a Podcasting Service / Learning to Code / Partner Webinars

Launching a Podcasting Service / Learning to Code / Partner Webinars

 
 
00:00 / 00:55:37
 
1X
 

MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working properly and Jordan and his team are seeing some major cultural shifts in the business.

Brian has found himself with some downtime, so now he is thinking about new avenues for Audience Ops. Brian outlines his idea for a new service offered through Audience Ops. An done-for-you podcasting service. He gets Jordan’s feedback and really explores why he thinks podcasts are the next logical step for the business. He also drops a big announcement… Brian wants to learn to code.

We have some interesting conversation about alternative content on this episode and some really useful reflections on the founder’s role within his company.

Here are today’s conversation points:

  • Get ready for MicroConf.
  • Brian’s new service launch.
  • Considerations for future podcast topics.
  • Jordan’s March recap.
  • Why Brian wants to launch a new service.
  • The all-done-for-you podcast service breakdown.
  • Brian’s small beta group for the new service and the results.
  • The benefits of podcasting content.
  • The second version of Carthook update.
  • Jordan’s webinar experiment.
  • The benefits of webinars.
  • How to create pitch-hitter scenarios.
  • How Carthook uses paid ads.
  • The ad strategy Jordan used for the webinar.
  • Brian’s results from his Productize webinar.
  • Why Brian wants to learn to code.
  • How to be a full stack product person.
  • Jordan’s adjustment to a larger work team and changing the dynamic.

Resources Mentioned Today:

Audience Ops Podcasting Service

Bullet Train

CodeMentor.io

Carthook

Castos

MicroConf

Ops Calendar

Productize

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

Charging For Attention / Elusive Product-Market-Fit

Charging For Attention / Elusive Product-Market-Fit

 
 
00:00 / 28:44
 
1X
 

It has been a crazy couple of weeks for both of us. We took a break last week, but we are back and we’ve got some great topics!

Jordan spent all of last week fixing a product issue. It was hard, it was frustrating, and it showed him just how great his team could be. He explains what happened to Carthook and how the problem was resolved.

Brian is performing an experiment with his Productize course. He is reaching out to a cold audience. He shares why he felt this was the way to go and lays out how he plans to attract new customers as this experiment progresses.

Join us today as we discuss the reality of customer service. We talk about the importance of meeting customer expectations and doing it with a smile. We also dig into how to go about finding those customer expectations when they aren’t that obvious.

Here are today’s conversation points:

  • Brian’s webinar experiment.
  • Jordan’s frustrating week and how he and his team coped.
  • How price point affects a customer’s expectations.
  • The Productize webinar ad strategy.
  • How to make data work for you in an experiment.
  • Brian’s results thus far in his experiment.
  • How to cope with doubt in your service.
  • When to decide to push or pivot.
  • How to help customers find solutions.

Resources Mentioned Today:

Audience Ops

Carthook

Ops Calendar

Productize Course

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