Bootstrapped Web

Bootstrapped Web

Business EN ↓ 172 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.

Author

Bootstrapped Web

Category

Business

Podcast website

bootstrappedweb.com

Latest episode

May 30, 2026

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Episodes

Prompt Engineering 07.06.2024

Launch week.  AI demos.  Prompt engineering.  Help docs.  Product marketing.  New feature prep.  B2B vs. B2C strategies.  Coastal living.  Mainstream AI. Connect with Brian: Brian's Product Consultancy:   Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan o...

Build in public 31.05.2024

Troubleshooting back pain.  "Early access" vs. "Sign up".  Build (or brag) in public.  Bootstrapping via consulting.  Starter app templates.  The AI voice space.  No-BS marketing.  Working outside. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's consultancy:  Instrumental Products Brian's SaaS,  Clarityflow   B...

Launch and learn 24.05.2024

Shady domain brokers.  Cooling off on product ideas.  Pricing questions.  High vs. low volume funnels.  Launch and learn.  Conflicting realities.  Deadlifts.  Summer travel. Connect with Brian: Brian's Product Consultancy:   Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally Jordan on Twitter: ...

AI Products 17.05.2024

GPT-4o.  Sleepless nights.  Product idea excitement.  Self-serve funnels.  Keeping calm before the storm.  Selling to small business.  Knicks in 6? The David Park Tweet that Jordan referenced. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's consultancy:  Instrumental Products Brian's SaaS,  Clarityflow   Brian...

Product Hunting 10.05.2024

No, we're not talking about Product Hunt (the website) today.  This one's about: Hunting for new product ideas.  Categories in AI.  Finding a partner.  Divesting in audience.  Hobbies. Attention diets.  Mothers day. Connect with Brian: Brian's Product Consultancy:   Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jo...

Startup Names 03.05.2024

Choosing a name. YouTube experiments. SEO. Reaching a foreign industry. Branding exercise. The New York Knicks. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's consultancy:  Instrumental Products Brian's YouTube channel: @briancasel Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @bri...

Entrepreneurial Seasons 26.04.2024

Protyping with AI.  Burnout aftermath.  Validation theories that need retiring.  Go-to-market.  MVP speed.  SaaS UI components as a service.  Kitchen Reno.  Passover.  Knicks Games. Connect with Brian: Brian's Product Studio:   Instrumental Products Brian's YouTube channel:  @briancasel Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jor...

Not Selling to SaaS 19.04.2024

Email for SaaS.  Selling to Main Street.  AI in the real world.  Offloading customer support.  UI/UX consultancy pricing.  YouTube experimentation.  Vacation guilt.  Kitchen renovations. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's consultancy:  Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twi...

Sell to SaaS? 11.04.2024

Exploring products that sell to SaaS.  Flights.  Credit card points.  Passover.  Elections.  Twitter.  Validation.  No-kids vacations. Connect with Brian: Brian's Product Studio:   Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal

Make it Rough 05.04.2024

Idea hunting.  Competitors.  Levels.  Portfolios.  Rough products.  Customer success.  Weekly pricing.  Productized services.  Earthquakes.  Supplements. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's consultancy:  Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads: ...

Creating Content & New Product Ideas 29.03.2024

Brian's first LinkedIn post.  YouTube.  Texas.  Northeast.  Inbound vs. outbound.  New product ideas.  AI.  Ecommerce.  Customer Success.  Tapping demand. Connect with Brian: Brian's Product Studio:   Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Th...

Ideas & Tech Stacks 15.03.2024

Exploring new ideas via conferences.  Building in Laravel vs. Rails.  Training customer success.  Leveraging audience as an employee vs. founder.  Travel energy. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's new consultancy:  Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian...

The internet is a confusing place 08.03.2024

SaaS trends. Product studio.  Pivots.  Personal energy.  Business energy.  Ecommerce Space.  Bootstrapping.  First principles.  Product idea mining.  Platform risk.  Elementary school talent shows. Connect with Brian: Brian's Product Studio:  Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally J...

Charging for Onboarding 23.02.2024

Launching a consultancy.  Generating pipeline.  Breaking limiting mindsets.  Outsource vs. in-house SDRs.  Paid customer onboarding.  Daddy-daughter dancing. Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's new consultancy: Instrumental Products Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Th...

New Directions 16.02.2024

AI everywhere.  Zuck's shots fired.  Committing to the new direction.  Customer success.  "Starter for hire" consultancy concept.  Skiing.  Birthdays. Connect with Brian: Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal

2024 Calculus 02.02.2024

Homepage experiments.  Marketing is too expensive.  Product-led growth.  VC game.  Bootstrapper game.  Cold outreach.  Over-correcting.  Shingles.  Vienna.  Snowboarding.   Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's new content:   fullstackfounder.co   Brian's SaaS,  Clarityflow   Brian on Twitter:  @casja...

Enough Time 19.01.2024

Customer Success.  Offers product. Consulting aint so bad.  Hiring a video editor.  Redefining success.  Not enough time.  Ski trips with kids.  Ski trips with adults.  Selling before launching.  Alarms. Connect with Brian: Brian's new business:   fullstackfounder.co   Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Connect with Jordan: Jordan's company,  Ra...

Pipeline Energy 12.01.2024

  Energizing the pipeline, energizing customer success, shipping a marketing site, unrealistic time estimations, getting snowed in, too much coffee (or not enough?)...  Connect with Jordan: Jordan's company,  Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal Connect with Brian: Brian's new business:   fullstackfounder.co   Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam B...

Blank Canvas 05.01.2024

New Year, new start, a blank canvas...  Working more (or less).  Clarityflow Commerce.  New brand name.  YouTube.  Growing pipeline.  Selling a product two ways.  Runway pressure.  Just another year :) Connect with Brian and Jordan: Brian's building:  fullstackfounder.co  (site is coming a few days after this episode publishes!) Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Thre...

What would a young Jordan and Brian say? 15.12.2023

In our final show of 2023, we're going deep... What would our younger selves think?  What were our biggest milestones to date?  Hardest challenges?  What's our favorite "cheat code"?   Connect with Brian and Jordan: Brian's building:   InstrumentalProducts.com Brian's SaaS,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Jordan's company,  Rally Jordan on Twitter:  @jorda...

Winning Partnerships 08.12.2023

Creator businesses.  Self-serve demos.  Partnership Gold.  Stair-stepping.  Sales process.  Economy and SaaS.  YouTube.  Marketing in 2024.  Audience.  What else?  We'll see... 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 Bri...

Operating a Media Company 01.12.2023

Black Friday fun. Cold email. Sales teams. Product market fit. Website redesign. Media company operations. Audience funnels. 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

News Diets & Work Balance 17.11.2023

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: ...

FOMO, Focus, and AI 10.11.2023

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 T...

Compensation, Content, & Speed 03.11.2023

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 Jo...

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