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.

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 Rails Clarityflow Subscribe to Brian's new podcast with Justin Jackson: The Panel

01-09
39:32

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

12-13
01:06:33

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 

12-06
01:07:16

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

11-08
56:45

"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   

11-01
55:08

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

10-25
01:06:47

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: @casjam

10-18
01:14:19

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

10-11
54:17

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, Clarityflow  Brian on Twitter: @casjam Brian on Threads: @brian.casel

09-27
01:01:26

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

09-20
55:55

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

09-13
55:11

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: @jordangal

08-30
50:51

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

08-22
55:08

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 on Twitter: @jordangal Jordan on Threads: @jordangal

08-16
42:39

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.casel

08-09
01:09:30

Pricing 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

08-02
44:17

Era 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

07-18
47:27

What's Next?

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

07-12
01:05:27

The Morning After

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

06-28
42:27

Dialing In

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

06-21
01:02:05

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