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 minEp. 281

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 minEp. 280

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 minEp. 279

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 minEp. 278

"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 minEp. 277

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 minEp. 276

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 minEp. 275

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 minEp. 274

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 minEp. 273

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 minEp. 272

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 minEp. 271

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 minEp. 270

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 minEp. 269

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 minEp. 268

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 minEp. 267

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 Jor...

Aug 02, 202444 minEp. 266

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...

Jul 18, 202447 minEp. 265

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...

Jul 12, 20241 hr 5 minEp. 264

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...

Jun 28, 202442 minEp. 263

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...

Jun 21, 20241 hr 2 minEp. 262

Hey, Rosie

Launching heyrosie.com. First demos. Twitter feeds. Productized consulting. Homepage rewrite. Summer camp. Concerts. Connect with Jordan: Jordan's company, Rosie 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: @brian.casel...

Jun 14, 20241 hr 10 minEp. 261

Prompt Engineering

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 on Threads: @jordangal...

Jun 07, 202459 minEp. 260

Build in public

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

May 31, 20241 hr 8 minEp. 259

Launch and learn

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: @jordangal Jordan on Threads: @jordangal...

May 24, 202456 minEp. 258

AI Products

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

May 17, 202459 minEp. 257

Product Hunting

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

May 10, 202457 minEp. 256

Startup Names

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: @brian.casel...

May 03, 202454 minEp. 255

Entrepreneurial Seasons

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

Apr 26, 202456 minEp. 254

Not Selling to SaaS

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

Apr 19, 202447 minEp. 253

Sell to SaaS?

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...

Apr 11, 202435 minEp. 252