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Bootstrapped Web

Bootstrapped Web
Author: Bootstrapped Web
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© 2025 Bootstrapped Web
Description
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.
169 Episodes
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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).
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 Threads: @jordangal
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: @brian.casel