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
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:
What Brian's up to:
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: @jordangal
- Brian on X: @casjam
We're still podcasting here:
...
Keep your Bootstra...
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:
Connect with Brian:
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:
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:
Connect with Jordan:
Connect with...
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:
- Brian on Twitter: @casjam
Jordan's stuff:
...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:
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:
- Brian on Twitter: @...
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 Thre...
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: ...
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....
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
Jor...
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
- Bri...
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: @cas...
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 &...
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...
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 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: @jordang...
Popular Podcasts
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.