Bootstrapped Web - podcast cover

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

Our 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 Rai...

Jan 09, 202540 minTranscript available on Metacast

Our 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 Rai...

Jan 09, 202540 minTranscript available on Metacast

Year-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...

Dec 13, 20241 hr 7 minTranscript available on Metacast

Year-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...

Dec 13, 20241 hr 7 minTranscript available on Metacast

Bluesky.

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...

Dec 06, 20241 hr 7 minTranscript available on Metacast

Bluesky.

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...

Dec 06, 20241 hr 7 minTranscript available on Metacast

Building 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...

Nov 08, 202457 minTranscript available on Metacast

Building 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...

Nov 08, 202457 minTranscript available on Metacast

"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 Clarityfl...

Nov 01, 202455 minTranscript available on Metacast

"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 Clarityfl...

Nov 01, 202455 minTranscript available on Metacast

Probably 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...

Oct 25, 20241 hr 7 minTranscript available on Metacast

Probably 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...

Oct 25, 20241 hr 7 minTranscript available on Metacast

Funnels & 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: @c...

Oct 18, 20241 hr 14 minTranscript available on Metacast

Funnels & 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: @c...

Oct 18, 20241 hr 14 minTranscript available on Metacast

Products 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...

Oct 11, 202454 minTranscript available on Metacast

Products 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...

Oct 11, 202454 minTranscript available on Metacast

Pressing 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, C...

Sep 27, 20241 hr 1 minTranscript available on Metacast

Pressing 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, C...

Sep 27, 20241 hr 1 minTranscript available on Metacast

Onboarding 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...

Sep 20, 202456 minTranscript available on Metacast

Onboarding 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...

Sep 20, 202456 minTranscript available on Metacast

What 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...

Sep 13, 202455 minTranscript available on Metacast

What 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...

Sep 13, 202455 minTranscript available on Metacast

Why 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: @jordan...

Aug 30, 202451 minTranscript available on Metacast

Why 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: @jordan...

Aug 30, 202451 minTranscript available on Metacast

If 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...

Aug 22, 202455 minTranscript available on Metacast

If 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...

Aug 22, 202455 minTranscript available on Metacast

Funnels & 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 o...

Aug 16, 202443 minTranscript available on Metacast

Funnels & 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 o...

Aug 16, 202443 minTranscript available on Metacast

Networks & 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.case...

Aug 09, 20241 hr 10 minTranscript available on Metacast

Networks & 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.case...

Aug 09, 20241 hr 9 minTranscript available on Metacast