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.

Episodes

January 9, 2025 39 mins

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.

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Mark as Played

2024 look-back and takeaways.  2025 goals.  Let's go!

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Mark as Played
December 6, 2024 67 mins

Bluesky takes.  Activation funnels.  Retention.  Delegating.  Demo videos.  Video marketing.  Sick vacations.

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Mark as Played
November 8, 2024 56 mins

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.

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Mark as Played
November 1, 2024 55 mins

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:

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Mark as Played
October 25, 2024 66 mins

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:

Jordan's stuff:

...
  • Mark as Played
    October 18, 2024 74 mins

    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).

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    Mark as Played
    October 11, 2024 54 mins

    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:

    Mark as Played
    September 27, 2024 61 mins

    Brian and Jordan's expert (lol) takes on WordPress-land.  Car shopping.  Netflix rec's.  Funnel tracking.  Customer observations.  Over-building.

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    If you're wondering "what's happening in WordPress?", our friend Matt Medieros published this excellent "just the facts" timeline.

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    Mark as Played
    September 20, 2024 55 mins

    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:

    Jordan's stuff:

    Mark as Played
    September 13, 2024 55 mins

    Q4 energy.  Signup funnels.  Self-serve vs. not.  Building assets vs. building cashflow.  Membership business models.  

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    Mark as Played
    August 30, 2024 50 mins

    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:

    Jor...

    Mark as Played
    August 22, 2024 55 mins

    Today on Bootstrapped Web:

    What if we bootstrapped?  Funnel projects.  Pricing experiments.  Software speed.  Tech-enabled services.  Listener conversations on Ripple.

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    Mark as Played
    August 16, 2024 42 mins

    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:

    Mark as Played
    August 9, 2024 69 mins

    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

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    Mark as Played
    August 2, 2024 44 mins

    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:

    Mark as Played
    July 18, 2024 47 mins

    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.

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    Mark as Played
    July 12, 2024 65 mins

    Brian's next product announcement.  Marketing first.  Small bets.  Private podcasting.  AI product development speed.  Summer vacations.

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    Mark as Played
    June 28, 2024 42 mins

    US Presidential debate analysis.  America.  Launch week.  First customers.  Perfect storm for a new product idea.  Questioning assumptions.  Seeking feedback.

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    Mark as Played
    June 21, 2024 62 mins

    Tailor-Made UI.  Knowing your customer.  Launch-week learnings.  Sales calls.  Cold outreach.  Margin & space.  Date night hangovers.  Summer camp.

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    Mark as Played

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