50 episodes

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.

Bootstrapped Web Bootstrapped Web

    • Business
    • 4.9 • 55 Ratings

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.

    News Diets & Work Balance

    News Diets & Work Balance

    On today's episode:

    Our news diets and managing stress with world events
    New onboarding flows & outreach wins
    Board meeting dynamics
    SaaS viability in 2024

    Connect with Brian and Jordan:

    Brian's new thing:  InstrumentalProducts.com
    Brian's SaaS, Clarityflow 
    Brian on Twitter: @casjam
    Brian on Threads: @brian.casel
    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal

    • 50 min
    FOMO, Focus, and AI

    FOMO, Focus, and AI

    On today's episode:

    Brian goes public with his new thing for 2024...
    Jordan onboards & optimizes the new sales team
    Discovery channels vs. relationship channels
    Spicy takes on AI startup land...

    Connect with Brian and Jordan:

    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal
    Brian's new thing:  InstrumentalProducts.com
    Brian's SaaS, Clarityflow 
    Brian on Twitter: @casjam
    Brian on Threads: @brian.casel

    • 55 min
    Compensation, Content, & Speed

    Compensation, Content, & Speed

    On today's episode:

    Sharing our real time stories publicly & transparently
    Compensation for sales teams vs. product teams
    Developing the content muscle
    Self-serve & async demos and onboarding
    Exploring a coaching offer around product strategy

    Connect with Brian and Jordan:

    Brian's company, Clarityflow 
    Brian on Twitter: @casjam
    Brian on Threads: @brian.casel
    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal

    • 57 min
    Staring Reality In The Face

    Staring Reality In The Face

    On today's episode:

    A few words on world events
    Brian's runway and strategic planning for 2024
    Jordan's reallocating of resources and investment
    Brian's firing himself from sales
    Jordan's hiring for sales

    Connect with Brian and Jordan:

    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal
    Brian's company, Clarityflow 
    Brian on Twitter: @casjam
    Brian on Threads: @brian.casel

    • 44 min
    Product Growth Levers

    Product Growth Levers

    On today's episode:

    When does shipping product lead to growth?
    Muddy Metrics
    Sports, exercise, health, eating, and drinking habits

    Connect with Brian and Jordan:

    Brian's company, Clarityflow 
    Brian on Twitter: @casjam
    Brian on Threads: @brian.casel
    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal

    • 55 min
    Getting Outside Help

    Getting Outside Help

    On today's episode:

    How we work with coaches & consultants to guide strategy & implementation
    UX hangover on shipped features
    Selling software "once"

    Connect with Brian and Jordan:

    Jordan's company, Rally
    Jordan on Twitter: @jordangal
    Jordan on Threads: @jordangal


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

    • 1 hr 9 min

Customer Reviews

4.9 out of 5
55 Ratings

55 Ratings

ItsDanWu ,

Great insight into a founders psyche!

Love how Jordan and Brian are taking us with them on their founder journey. You don’t get insight into a founders psyche and day-to-day in any other podcast in my opinion. Rooting for you guys!

J. Barshop ,

Awesome show, highly recommend!

Brian, Jordan and their guests provide some incredibly actionable and compelling content, spotlighting incredible founder stories that are guaranteed to teach you something new.

Highly recommend listening and subscribing to Bootstrapped Web if you want the knowledge AND mindsets to effectively grow your business (and reach all of your overall goals as a result)!

Just for the culture ,

The most insightful podcast you'll find

Finally you get the chance to know about the struggles of growing a business as they're happening.

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