PODCAST · business
Bootstrapped Web
by 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
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Just another Friday on the mics
We're cross-posting this week's episode of The Panel here in the Bootstrapped Web feed. While Justin's traveling, Jordan and Brian do a updates episode. Workout routines. Mindsets. North Stars. AI Agents. New York Knicks. Jordan, Brian, and Justin have been publishing weekly over on The Panel...
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We're back!
Jordan and I are back on the mics together! But it's not Bootstrapped Web. Jordan is joining Justin Jackson and me as the 3rd permanent co-host of The Panel Podcast. Be sure to subscribe to The Panel Podcast feed to receive future episodes. Subscribe to The Panel Podcast in your podcast player....
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2025 recap & 2026 outlook
Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook. What Jordan's up to: Rosie Offiste Podcast Jordan on X What Brian's up to: Builder Methods YouTube Agent OS & Design OS Panel Podcast Brian on X
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2025 Mid-Year Update
We're back for a mid-year update! The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year? What we're working on: Jordan's in rocket ship mode on Rosie. Brian's building Builder Methods and YouTubing. Don't be a stranger! Jordan on X…
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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...
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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
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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…
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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"...
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"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...
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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!...
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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...
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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.…
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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…
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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...
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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:...
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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...
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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…
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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…
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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:...
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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...
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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…
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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:...
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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…
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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:...
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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…
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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…
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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...
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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…
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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…
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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,...
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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...
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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,...
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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...
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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:...
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Make it Rough
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:...
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Creating Content & New Product Ideas
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...
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Ideas & Tech Stacks
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...
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The internet is a confusing place
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…
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Charging for Onboarding
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...
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New Directions
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…
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2024 Calculus
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…
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Enough Time
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...
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Pipeline Energy
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…
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Blank Canvas
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...
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What would a young Jordan and Brian say?
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:...
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Winning Partnerships
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...
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Operating a Media Company
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,...
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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...
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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…
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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,...
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ABOUT THIS SHOW
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.
HOSTED BY
Bootstrapped Web
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Frequently Asked Questions
How many episodes does Bootstrapped Web have?
Bootstrapped Web currently has 284 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Bootstrapped Web about?
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...
How often does Bootstrapped Web release new episodes?
Bootstrapped Web publishes regularly with 284 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Bootstrapped Web?
You can listen to Bootstrapped Web on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Bootstrapped Web?
Bootstrapped Web is created and hosted by Bootstrapped Web.
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