Bootstrapped Web

Bootstrapped Web

Business EN ↓ 172 episodes

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.

Author

Bootstrapped Web

Category

Business

Podcast website

bootstrappedweb.com

Latest episode

May 30, 2026

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Episodes

KPI Dashboards, Hiring Sales vs. Customer Success, & Solo Founders 22.06.2017

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 pi...

Customer Overwhelm, Hiring & Firing Teammates 08.06.2017

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 th...

YouTube Content, Creating Webinars, Team Retreats 25.05.2017

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 a...

Back from MicroConf! More Signups! Facebook Ads Funnels! 11.05.2017

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...

Onboarding First SaaS Customers 30.03.2017

Today we discuss how our respective businesses have begun on-boarding customers to our new products. The Shopify checkout app is growing and Jordan and his team are learning what makes the app successful. Brian has begun on-boarding clients on to the Audience Ops Calendar. We discuss what we’re learning from these processes and how that will change how we move forward. Microconf Vegas is just arou...

Launching a New Service in 5 Days & Hitting Your Product Stride 09.03.2017

We have some big news coming up the following weeks. Brian discussed his recent experience with Facebook ads and the pros and cons of marketing on the platform. Jordan shares his found  his new found security in his business. We are really excited about the new rewrites and product launches and we talk about it all! [tweetthis]Marketing needs to make that promise and then the product needs to deli...

Updates Facebook Ads, Public Speaking, & Entrepreneurial Parenting 23.02.2017

Welcome back to Bootstrapped Web. On today’s episode we cover a lot of subjects that are both business and personal nature. We update you on Brian’s Calendar product and Jordan tells us about a talk he gave to his accelerator group. We also discuss Brian’s experience with Facebook ads and how Facebook is helping him get the word out about Audience Ops. He shares some tools he has found useful  whi...

Get-to-Launch Roadmap, Hiring (more) Developers, When to Work on Marketing 16.02.2017

We talk about Big Snow Tiny Conf and team growth today. Brian had a great time up at Vermont’s Big Snow Tiny Conf and has some awesome take-a-ways to share. Jordan is growing his team and is getting ready for a big marketing push. We both have some useful insights into team management and creating a successful product funnel. This is a good episode to see what goes into a product launch and how a...

2016 Recap & 2017 Goals 22.12.2016

Well, 2016 is coming to an end. Today we’ll compare our goal lists from last year and reflect back on what went wrong  and what went right.   Carthook and Audience Ops have both grown and changed so let’s sit down and take a look at our 2016 results. We will also discuss our goals for 2017 and how we plan to make them happen. This will be our last episode for 2016, and we’ll pick up next year. [tw...

Updates: Redesign, Marketing Multiple Products, & Selling Services 15.12.2016

Today’s Bootstrapped Web is going  to be an up-date episode. We both have a lot to talk  about with what we’re working at the moment. Audience Ops and Carthook have new products and we discuss what is working for our sales respectively. We talk about transparency and some resources that will help you improve your sales game.  So tune in for the latest developments in Carthook and Audience Ops and...

Family & Entrepreneurship 08.12.2016

Hey we’ve got a party episode with Rob and Sherry Walling from the podcast ZenFounder. We are going to discuss how to balance life with kids and entrepreneurship. We explore the common problems with living  with kids and keeping a business going. We also discuss how entrepreneurship affects marriage. Rob and Sherry share how they are able to keep their communication open. We also discuss how we ou...

Launching 2nd Products w/ Ruben Gamez 24.11.2016

Welcome back to Bootstrapped Web. Our guest today is Ruben Gamez, the founder of Bidsketch.com. We are talking to Ruben today because Bidsketch is getting ready to launch a new product. Since we both are launching new products we thought it would be good to compare notes. Bidsketch’s main product has been a proposal tool. Now they want to add a signature app to their brand. Today we discuss how to...

Updates: Validating a Consulting Offer / Self-Funding a New SaaS 17.11.2016

Today’s episode is an update episode. Jordan tells us about finding his customer base for the funnel tool. Brian discusses how he is working with his developers on a new training product he is planning. We discuss when to allow custom jobs and when to say no. We also discuss what challenges a young bootstrapped company needs to expect. Building your company is so much harder, than it sounds. If yo...

Taking a Big Shot vs. Lots of Little Shots 10.11.2016

On today’s episode, we welcome Craig Hewitt and Justin Jackson to the podcast. Jordan is having some time away. On today’s episode Craig, Justin, and Brian all discuss how to build and keep a company on track. We discuss what drives us and what we’re working on at the moment. If you want to know how to plan a product or just try to set a trajectory for your business, this is the episode for you! C...

Pricing Questions / SaaS vs. Service 27.10.2016

We’ve got a party episode today. We welcome Rob Williams of Workshop and Folyo. Allan Branch joins us later on in the episode when we discuss his time with Less Accounting. [tweetthis]There are pros and cons to both the service and the software side of things. - Brian[/tweetthis] Today’s topic was primarily pricing. How to price effectively, why to price at a certain level, and what pricing can do...

Adding Service to Software / Marketing Pre-MVP 13.10.2016

Today’s episode is basically a therapy session for us both. We lay out our current issues and talk each other though the options. Jordan is dealing with customers and their personal expectations for the products. Brian is looking for balance in his development stage on the calendar product. We try our best to see our situations from all angles and possibilities. [tweetthis]The first step is decidi...

Updates: Dev Process, MRR Milestones, Remote vs. Office 06.10.2016

Today is a basic update episode, but we have a special guest as well. Justin McGill is the co-founder of LeadFuze and co-host of the podcast Zero to Scale . He joins us on the update train today and gives us an idea of what the future holds for LeadFuze. Jordan tells us how his team meetup is going and Brian fills us in on what is going on with Audience Ops. [tweetthis]Finding talent is so hard &a...

Going Global: Team Travel, Tiny Confs, & Remote Lifestyle 29.09.2016

We’re are having a “party” episode with some special guests today. We’ve got Dave Rodenbaugh, Craig Hewitt, and later on Brad Touesnard joining us. We are all involved with Big Snow Tiny Conf. Brian is head of the Vermont event, Dave is head of the West event (Colorado.) Craig is taking care of our European event in France. Today we talk about the conference and why we love it. [tweetthis]It's [Bi...

Going Global: Team Travel, Tiny Confs, & Remote Lifestyle 29.09.2016
Pre-selling and Planning to Build 'Audience Ops Calendar' 22.09.2016

Today on Bootstrapped Web we talk about a new product from Audience Ops. Brian has developed a software product called Audience Ops Calendar. He has offered it to 12 clients and based his approach on a pre-sale model. During today’s episode Brian tell us how he has developed the product. He answers why he chose  to develop a calendar, how to use his software, and how he plans to market it. If you’...

Cofounders - w/ Rob Walling and Ben Fisher 01.09.2016

We welcome Rob Walling and Ben Fisher to the podcast today. We are going to discuss the topic of co-founders. Rob is the original founder of Drip, but has found a co-founder named Derek. Ben is Jordan’s co-founder in Carthook. Brian however is the solo founder prospective in today’s conversation. Brian has had co-founders, but Audience Ops is all him. On today’s episode Jordan and Ben talk about h...

New Products First Steps & Next Steps 25.08.2016

Well the launch for our new products are getting nearer. Today we give a general update on things and we talk about where we are on the new products. Brian is in the beginning of this process and Jordan is coming to the end of the process. Planning a new product is stressful. We discuss that stress and how we have personally dealt with it. There are tons of decisions that have to be made and there...

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