

Bootstrapped Web
Bootstrapped Web
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
Episodes
Mentioned books

Jun 4, 2020 • 45min
Navigating Stress & Distractions
The world is in chaos but we’re still here. Today we’re talking about some of the trends and the future of podcasting after some big news with The Joe Rogan Experience. We’re also going over some updates with Carthook, ProcessKit, and Audience Ops.
[tweetthis]"It does seem like there’s still that massive gap between the seed rounds and the Series A. Right? When you’ve grown to a certain level and you still need more firepower to grow." - Brian [/tweetthis]
Here are today’s conversation points:
The big debate over Joe Rogan’s Spotify dealJordan’s (who is not soliciting for investments, SCC) fears over investorsProcessKit’s onboarding course, not quite readyFunding: social media ads, marketing partnerships (affiliates and referrals)Jordan’s biggest deal ever...and he didn’t even talk to the prospectDifficult clients in Audience Ops
[tweetthis]"You’ve been working on something for over five years. This is all you care about. You love it. You love the job, the company, the people. There’s so much involved in that. How are you supposed to find investors that are going to respect that?” - Jordan [/tweetthis]
Resources/Links:
Substack
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.

May 28, 2020 • 42min
What if we take some off the table?
In today’s episode we’re talking about socializing with family friends and work during the pandemic, as well as the latest news and questions on our minds about the current status of tech and the world. PokerStars, weekly stand-ups, Facebook, and what reopening might look like. The big question on everyone’s mind is: “How long is this going to last?” In business news, we’re talking about Brian’s new ProcessKit course, and Jordan’s views on hiring.
[tweetthis]"You’re taking money off the table but you’re also taking off the table, the desire to sell when the first semi-big offer comes along and instead go super-big." - Brian [/tweetthis]
Here are today’s conversation points:
Facebook newsJordan’s most popular tweet everTaking on more money and the possibility of hitting zeroWhat is Clubhouse and why is it so big right now?Serendipitous audio conversations versus Twitter versus podcastingPrivate podcastsInteresting new platforms: SubstackUpdates on Brian’s new course about ProcessKitJordan’s views on hiringBrian’s work on the sales demos
[tweetthis]"People watch how you treat people and then they put themselves in those shoes.” - Jordan [/tweetthis]
Resources/Links:
Clubhouse.io
Substack
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook

May 21, 2020 • 44min
Managing Customers & Managing Teams
Welcome back! Brian and Jordan are back behind the mic. We’re talking about ProcessKit’s best month, and Brian’s excitement about moving forward and making progress. We’re also talking about Jordan’s experience with Carthook’s people coach and accidental faux pas with his leadership team.
[tweetthis]"I am acting fast on a lot of the smaller requests. I only do it when I’ve heard it two or three times from different customers. Usually and hopefully I’m shipping something fast and notifying multiple customers that, ‘Hey, we just shipped that thing." - Brian [/tweetthis]
Here are today’s conversation points:
ProcessKit’s best month with conversionsJordan’s focus on hiring and salariesBrian’s focus for ProcessKit: onboardingBrian’s old blog postsSetting up SEOJordan’s humbling experience with the people coachAccidentally taking away authorityBrian’s support requests on ProcessKit
[tweetthis]"What am I really doing though? I’m taking authority away from their manager. I’m not allowing that manager to be that person, resource, and that trust and that bond and… I’m messing with that and it’s not helpful." - Jordan [/tweetthis]
Resources/Links:
Ahrefs.com
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.

Apr 26, 2018 • 52min
Value of a Coach / Hiring Spree / Launching in Public
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.
[tweetthis]There are so many really talented, really smart, really motivated people, they just want to work remotely. - Brian[/tweetthis]
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.
[tweetthis]If you are going to provide value, it's not just talking, it's work. - Jordan[/tweetthis]
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.

Apr 26, 2018 • 52min
Value of a Coach / Hiring Spree / Launching in Public

Apr 19, 2018 • 48min
What If We Ran Your Business (For the Fun of It)?
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.
[tweetthis]We [founders] think in a certain way and maybe we don't remember what it is like to be an employee. - Jordan[/tweetthis]
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.
[tweetthis]Nobody is going to get as fired up and keep pushing than the founder. - Brian[/tweetthis]
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.

Apr 19, 2018 • 48min
What If We Ran Your Business (For the Fun of It)?

Apr 12, 2018 • 54min
The Carthook Team Talks Product Development Process
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!
[tweetthis]For bootstrapping new software startups, choose a more mature framework, rather than the trendiest stuff. - Brian[/tweetthis]
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.
[tweetthis]Spend whatever we need to spend, and eventually they [Ben & Rok] took that advice and now I regret it a bit. - Jordan[/tweetthis]
Resources Mentioned Today:
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.

Apr 12, 2018 • 54min
The Carthook Team Talks Product Development Process

Apr 5, 2018 • 56min