Bootstrapped Web
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys.
Bootstrapped Web · Brian Casel, Jordan Gal
Show overview
Bootstrapped Web has been publishing since 2016, and across the 10 years since has built a catalogue of 171 episodes. That works out to roughly 140 hours of audio in total. Releases follow a monthly cadence.
Episodes typically run thirty-five to sixty minutes — most land between 44 min and 56 min — and the run-time is fairly consistent across the catalogue. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-US-language Business show.
The show is still active — the most recent episode landed 3 months ago, though releases have slowed compared with earlier in the run. The busiest year was 2024, with 39 episodes published. Published by Brian Casel, Jordan Gal.
From the publisher
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.
Latest Episodes
View all 171 episodesEp 284We're back!
Jordan and I are back on the mics together! But it's not Bootstrapped Web.Jordan is joining Justin Jackson and me as the 3rd permanent co-host of The Panel Podcast.Be sure to subscribe to The Panel Podcast feed to receive future episodes.Subscribe to The Panel Podcast in your podcast player.Subscribe to The Panel Podcast on YouTubeFollow us on Twitter & Blusky, where we post the link to join us for our live recordings & chat every Friday:Follow Brian: Twitter / BlueskyFollow Jordan: Twitter / BlueskyFollow Justin: Twitter / Bluesky
Ep 2832025 recap & 2026 outlook
Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook.What Jordan's up to:RosieOffiste PodcastJordan on XWhat Brian's up to:Builder MethodsYouTubeAgent OS & Design OSPanel PodcastBrian on X
Ep 2822025 Mid-Year Update
We're back for a mid-year update!The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year?What we're working on:Jordan's in rocket ship mode on Rosie.Brian's building Builder Methods and YouTubing.Don't be a stranger!Jordan on X: @jordangalBrian on X: @casjamWe're still podcasting here:Jordan's: OffsiteBrian's: The Panel...Keep your Bootstrapped Web feed! We'll pop back in here again soon(ish).
Ep 281Our final episode (for now)
It's true. We're calling this a final episode—for now—but don't unsubscribe! We promise to pop into the feed every few months to catch up :) But for now, we're taking a breather and staying focused on executing our businesses in 2025: Jordan's crankin on Rosie, Brian's building Instrumental Products. Don't be a stranger! Connect with Jordan: Follow Jordan on Bluesky / Twitter Rosie Connect with Brian: Follow Brian on Bluesky / Twitter Instrumental Products Instrumental.dev - Components for Rails Clarityflow Subscribe to Brian's new podcast with Justin Jackson: The Panel
Ep 280Year-end takeaways & goals
2024 look-back and takeaways. 2025 goals. Let's go! Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instrumental.dev Instrumental Products Clarityflow Connect with Jordan: Follow Jordan on Bluesky / Twitter Jordan's company, Rosie
Ep 279Bluesky.
Bluesky takes. Activation funnels. Retention. Delegating. Demo videos. Video marketing. Sick vacations. Connect with Jordan: Follow Jordan on Bluesky / Twitter Jordan's company, Rosie Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instrumental.dev "One Month MVP" service Clarityflow
Ep 278Building out of a job
Putting in more hours to put in less. Building systems for delivering software. Deploying demo video(s). Listening to customers. Using a business to deepen your craft. News detox. Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instrumental.dev "One Month MVP" service Clarityflow Connect with Jordan: Follow Jordan on Bluesky / Twitter Jordan's company, Rosie
Ep 277"Thank you for solving my problem."
Bluesky is having a moment. Halloween. Customers telling us their problems are solved. Essential onboarding. Calm before the (hiring) storm. Projects are waiting. The podcasting election. Bluesky starter packs to follow: Founders & Bootstrappers Podcasters Ruby on Rails People Laravel Friends Connect with Jordan: Follow Jordan on Twitter Jordan's company, Rosie Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instrumental.dev "One Month MVP" service Clarityflow
Ep 276Probably fine
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Political noise. Removing features. Positioning. Products for developers. Idea wireframes (as a service). Hiring a video editor. Retainer-based hiring. Frequent flyer miles. Apple picking. Brian's stuff: Brian's products: New! Instrumental.dev "One Month MVP" service Clarityflow Brian on Twitter: @casjam Jordan's stuff: Jordan's product, Rosie Jordan on Twitter: @jordangal
Ep 275Funnels & Moonshots
Hey we didn't talk about WordPress this week! But we did talk about Elon... Also: Brian's working on a components product (instrumental.dev), Jordan's figuring out onboarding (heyrosie.com), and Brian's starting to scale consulting (onemonth.app). Join our free community for Bootstrapped Web listeners Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Connect with Brian: Brian's products: New! Instrumental.dev "One Month MVP" service Clarityflow Brian on Twitter: @casjam
Ep 274Products For Builders
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Brian's new product (Instrumental.dev). Comparing the open-source leadership styles of Matt, DHH, and Taylor. Building products for builders. Components. Tightening the team. Scaling consulting from 1 to...? Let's Go Mets. Brian's stuff: Brian's products: New! Instrumental.dev "One Month MVP" service Clarityflow Brian on Twitter: @casjam Jordan's stuff: Jordan's product, Rosie Jordan on Twitter: @jordangal
Ep 273Pressing Questions
Brian and Jordan's expert (lol) takes on WordPress-land. Car shopping. Netflix rec's. Funnel tracking. Customer observations. Over-building. Join our free community for Bootstrapped Web listeners If you're wondering "what's happening in WordPress?", our friend Matt Medieros published this excellent "just the facts" timeline. Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's MVP serice OneMonth.app Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel
Ep 272Onboarding Funnels
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Optimizing our onboarding funnels. Calls to action. Lead ads. ARPU. API plans. Pearl Jam. Sleep (or lack thereof). Brian's stuff: Brian's "One Month MVP" service Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's stuff: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal
Ep 271What Customers Want
Q4 energy. Signup funnels. Self-serve vs. not. Building assets vs. building cashflow. Membership business models. Join our free community for Bootstrapped Web listeners Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's MVP serice OneMonth.app Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel
Ep 270Why is SaaS hard?
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Why makes SaaS more difficult than other business models? Rosie first customers! Brian's pricing experiment update. Training businesses. AI waves. Profitability at $1-2m. College Football. US Open Tennis. Brian's stuff: Brian's "One Month MVP" service Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's stuff: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal
Ep 269If we bootstrapped
Today on Bootstrapped Web: What if we bootstrapped? Funnel projects. Pricing experiments. Software speed. Tech-enabled services. Listener conversations on Ripple. Join our free community for Bootstrapped Web listeners Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's MVP serice OneMonth.app Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel
Ep 268Funnels & Websites
Connect with Brian, Jordan and fellow listeners in the Bootstrapped Web community on Ripple.fm Today: Asking the hard-hitting questions like... Coconut pastries... for or against? Is anyone actually able to log into the black hole that is Meta ads? Publishing a 1-page HTML landing page shouldn't be difficult. Should it? Brian's stuff: Brian's "One Month MVP" service Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's stuff: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal
Ep 267Networks & Audiences
Ripple.fm is live and open. Rosie is live for self serve signups. Niche social networking. Advertising using video. Cold outreach playbooks. And a special guest joins the show Join our free community for Bootstrapped Web listeners Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's Consulting services: OneMonth.app & Tailor-Made UI Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel
Ep 266Pricing Experiments
Brian launches built and launched something new. 2 things actually. Jordan changes pricing strategy for Rosie. Brian also changes pricing strategy for Clarityflow. And all find our AI hardware "friend". Connect with Brian, Jordan and fellow listeners in the Bootstrapped Web community on Ripple.fm Brian's stuff: Brian launched Ripple.fm Brian's new "One Month MVP" service Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's stuff: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal
Ep 265Era of Trying Stuff
Yet another new product announcement from Brian. Jordan launches to first customers. The era of hacking on new ideas. Summer speed ups. Professional standards. Vacations. Special guest joins us to tell us it's time to stop. Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's newest thing: Ripple.fm Brian's Service: Tailor-Made UI Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel