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.
Author
Bootstrapped Web
Category
Podcast website
Latest episode
May 30, 2026
Where to listen?
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Episodes
Just another Friday on the mics 30.05.2026 1:11:08
We're cross-posting this week's episode of The Panel here in the Bootstrapped Web feed. While Justin's traveling, Jordan and Brian do a updates episode. Workout routines. Mindsets. North Stars. AI Agents. New York Knicks. Jordan, Brian, and Justin have been publishing weekly over on The Panel Podcast. Get sub'd! https://panelpodcast.com/
We're back! 21.02.2026 54:33
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 YouTube Follow us on Twitter & Blusky, where we post the link to...
2025 recap & 2026 outlook 17.12.2025 1:02:58
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: Rosie Offiste Podcast Jordan on X What Brian's up to: Builder Methods YouTube Agent OS & Design OS Panel Podcast Brian on X
2025 Mid-Year Update 21.08.2025 1:09:53
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: @jordangal Brian on X: @casjam We're still podcasting here: Jordan's: Offsite Brian's: The Panel ... Keep...
Our final episode (for now) 09.01.2025 39:32
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 Connec...
Year-end takeaways & goals 13.12.2024 1:06:33
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
Bluesky. 06.12.2024 1:07:16
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
Building out of a job 08.11.2024 56:45
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,...
"Thank you for solving my problem." 01.11.2024 55:08
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...
Probably fine 25.10.2024 1:06:47
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 stu...
Funnels & Moonshots 18.10.2024 1:14:19
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 wi...
Products For Builders 11.10.2024 54:17
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...
Pressing Questions 27.09.2024 1:01:26
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: @...
Onboarding Funnels 20.09.2024 55:55
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 J...
What Customers Want 13.09.2024 55:11
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...
Why is SaaS hard? 30.08.2024 50:51
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 Threa...
If we bootstrapped 22.08.2024 55:08
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, C...
Funnels & Websites 16.08.2024 42:39
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...
Networks & Audiences 09.08.2024 1:09:30
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: OneMont...
Pricing Experiments 02.08.2024 44:17
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, Clarit...
Era of Trying Stuff 18.07.2024 47:27
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 Se...
What's Next? 12.07.2024 1:05:27
Brian's next product announcement. Marketing first. Small bets. Private podcasting. AI product development speed. Summer vacations. Connect with Brian: Brian's next product landing page Brian's Service: Tailor-Made UI Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on...
The Morning After 28.06.2024 42:27
US Presidential debate analysis. America. Launch week. First customers. Perfect storm for a new product idea. Questioning assumptions. Seeking feedback. Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's consultancy: Tailor-Made UI Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @...
Dialing In 21.06.2024 1:02:05
Tailor-Made UI. Knowing your customer. Launch-week learnings. Sales calls. Cold outreach. Margin & space. Date night hangovers. Summer camp. Connect with Brian: Brian's Service: Tailor-Made UI Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal
Hey, Rosie 14.06.2024 1:09:38
Launching heyrosie.com. First demos. Twitter feeds. Productized consulting. Homepage rewrite. Summer camp. Concerts. Connect with Jordan: Jordan's company, Rosie Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's consultancy: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel
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