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Bootstrapped Web

Bootstrapped Webbootstrappedweb.com
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

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 bu...

May 28, 202042 minEp. 161

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 multip...

May 21, 202044 minEp. 160

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 cu...

Apr 26, 201852 minEp. 158

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...

Apr 19, 201848 minEp. 156

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 t...

Apr 12, 201854 minEp. 154

Launching a Podcasting Service / Learning to Code / Partner Webinars

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 Aud...

Apr 05, 201856 minEp. 152

Our 2017 Review & 2018 Preview

2017 is coming to a close and Jordan and Brian are looking back on this explosive year. They also share their plans for 2018. Audience Ops and Carthook both saw tremendous amounts of growth this year. That growth has caused the guys to reflect on 2017 and the lessons they have taken away from the experience. Brian has seen an uptake in sign-ups and Audience Ops has ridden a roller coaster this year. Brian shares what he learned from the sudden stop and go growth of the business. 2018 looks to be...

Dec 21, 201744 minEp. 146

Running a Black Friday Sale / Development Process

2017 has been a phenomenal year for Jordan and Brian. On today’s episode, they give the audience an update on the businesses and offer a glimpse into their plans for 2018. Brian is going to shift focus to Productize and relaunch a bigger and better product later. This means he will be closing enrollment in the course and beginning the maintenance phase of this upgrade. He shares how he reached this decision and why he is excited by the new possibilities it can bring. Jordan is adjusting to a gro...

Dec 07, 201747 minEp. 144

"Fattening" Your Company and... Freemium?

Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move the business to the next stage. Carthook is also growing their team and there have been some growing pains in the communication process. There have been some hard lessons in the process that Jordan hints at that could help business owners build...

Nov 16, 201755 minEp. 142

First Customer Demos, Paid Marketing Funnels, Team Communication

We have both reached a turning point in our marketing campaigns. Jordan has launched a new marketing funnel for Carthook’s Shopify tool. Brian has been running a new marketing campaign for Ops Calendar. We share how the campaigns are working for us and offer each other advice on how to improve our strategies. We also discuss how we keep our team culture positive when we ourselves are super busy and can’t give our undivided attention to individual projects. Our teams are growing and changing and ...

Oct 05, 201753 minEp. 140

Pricing Page Teardown, Employee Onboarding, Company Transparency

Today on Bootstrapped Web Jordan and Brian discuss what’s going on in their individual businesses. Brian is setting up Ops Calendar and takes today’s episode as a chance to get Jordan’s feedback from the customer’s point of view. Listeners who are interested in Ops Calendar can get excited because Brian gives a detailed description of what his service offers. Jordan has had some problems with retaining new team members. He shares what he has learned about the hiring process and how he keeps comp...

Sep 21, 201748 minEp. 138

SaaS Momentum, Servicing Demand, & Why Amazon Bought WholeFoods

We cover a lot in this episode of Bootstrapped Web. We give our listeners an update on both companies’ progress and we discuss some exciting news in the startup world. Brian shares some of the goals he has for Audience Ops in the near future. Jordan has an awesome story to share about his new VIP client. We compare our business needs and consider the unexpected problems that come with growth. We also discuss two really insightful articles that just came out, Amazon’s New Customer , by Ben Thomps...

Jul 27, 201745 minEp. 137

A Formula for Individual Success Metrics + Building a Hiring Engine

Happily, our client loads are increasing, but our staffs are starting to feel the increased workload. So, we need to hire more people to keep up. It’s a good problem to have. On today’s episode, we compare our staffing needs and discuss how we are trying to build a process that frees us both up for “CEO tasks.” As our businesses grow, our roles change. Brian shares his plans to cope with a couple of team members exiting the company. While Jordan recently spent some time away with his family. He ...

Jul 06, 201738 minEp. 136

KPI Dashboards, Hiring Sales vs. Customer Success, & Solo Founders

Today Brian and Jordan discuss growth. In Jordan’s case he is dealing with sudden growth, and in Brian’s case, he is planning for growth. Both share how they are handling this wonderful problem. Jordan has been focused on getting Carthook’s marketing up and running again, but it has become clear that his team needs him to focus on improving the customer support. It has been a struggle to really pinpoint what the team needs. Jordan calls it “customer success,” but Brian isn’t so sure that’s the b...

Jun 22, 201738 minEp. 135

Customer Overwhelm, Hiring & Firing Teammates

We are both hitting some major growth right now in our businesses, and that means a lot of excitement and a lot of restructuring. We talk about project managing, hiring the right people, and the efforts we are putting into our marketing and lead generation. Jordan recently went to Europe and met up with his team. He tells us how the trip went and the exciting milestone he saw while working with the Carthook team in Europe. Jordan has also had some people leave the company. He explains why they h...

Jun 08, 20171 hr 1 minEp. 134

YouTube Content, Creating Webinars, Team Retreats

We are back discussing our businesses and the progress that we have been making. On the personal front Jordan is heading off to Europe and Slovenia to work and hit the beach. Brian has been getting healthier with the BulletProof diet. Brian has been recording new episodes for his Productized podcast. He is hiring one person to take care of the editing, shownotes, social stuff, and posting. He is also trying to make two videos a week. He is also launching the Sell to Strangers webinar for his fun...

May 25, 201745 minEp. 133

Back from MicroConf! More Signups! Facebook Ads Funnels!

We are back from MicroConf and on this episode we share our takeaways and also update the important things going on in our businesses. Jordan shares how Russ Henneberry’s MicroConf talk encouraged him to look at his business differently. After this episode you may not look at funnels the same way again. Brian explains how MicroConf often helps him refocus his priorities. He has plans to reconnect with his personal brand and create some new engaging content. We discuss how he can do that. MicroCo...

May 11, 201759 minEp. 132