
Advertise on podcast: Bootstrapped Web
Rating
4.9from
This podcast has
170 episodes
Language
EnglishPublisher
Bootstrapped WebExplicit
No
Date created
2013/06/01
Latest episode
2025/12/17
Average duration
60 min.
Release period
35 days
Description
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.
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Check latest episodes from Bootstrapped Web podcast
2025 recap & 2026 outlook
2025/12/17
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:
RosieOffiste PodcastJordan on XWhat Brian's up to:
Builder MethodsYouTubeAgent OS & Design OSPanel PodcastBrian on X
2025 Mid-Year Update
2025/08/21
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: @jordangalBrian on X: @casjamWe're still podcasting here:
Jordan's: OffsiteBrian's: The Panel...
Keep your Bootstrapped Web feed! We'll pop back in here again soon(ish).
Our final episode (for now)
2025/01/09
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 Rails
Clarityflow
Subscribe to Brian's new podcast with Justin Jackson: The Panel
Year-end takeaways & goals
2024/12/13
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
Bluesky.
2024/12/06
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
Building out of a job
2024/11/08
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
"Thank you for solving my problem."
2024/11/01
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
Clarityflow
Probably fine
2024/10/25
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
Funnels & Moonshots
2024/10/18
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: @casjam
Products For Builders
2024/10/11
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
Pressing Questions
2024/09/27
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, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Onboarding Funnels
2024/09/20
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
What Customers Want
2024/09/13
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
Why is SaaS hard?
2024/08/30
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: @jordangal
If we bootstrapped
2024/08/22
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
Podcast reviews
Read Bootstrapped Web podcast reviews
ItsDanWu 2020/07/25
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 p...
J. Barshop 2018/02/14
Awesome show, highly recommend!
Brian, Jordan and their guests provide some incredibly actionable and compelling content, spotlighting incredible founder stories that are guaranteed ...
BecomingJimmy 2017/07/08
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.
Zeeeman123 2017/06/25
Fantastic
Love the dialogue these guys have discussing their common problems, tactics, etc. Extremely helpful and easy to follow. Gives me a lot more confiden...
Kiriath13 2016/04/01
Fly on the wall of a 1:1 mastermind
One of my favorite business podcasts. What's cool about it is that we get to hear in real time how Jordan and Brian are building their businesses. It'...
TheStove2 2016/03/11
An honest look at small tech businesses
Brian and Jordan don’t have all of the answers, and they don’t pretend to. What they do have is a pragmatic, analytical mindset they use to approach b...
Justin_MW 2015/10/02
Fantastic insights into bootstrapped startups
These guys are fantastic. Their show is a back and forth sharing their successes and struggles with productized and services businesses. A must listen...
Brendan at Kiinetics 2015/09/24
Great, practical, usable start-up advice and insight
A really useful weekly podcast on essentially every aspect of a small business start-up. Each week tends to get really specific, and Brian and Jordan ...
PaulHalagan 2015/08/10
Content Marketing Gold
I’ve been a long time listener and Brian and Jordan continue to dish up valuable insights from their experience as product developers. This episode cr...
JamesJosephFinn 2015/05/29
Worth it’s weight in gold
Are you trying to make a living online by developing a web-based service? Then stop right now and subscribe. These two accomplished tech entrepreneurs...