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Bootstrapped Web

Bootstrapped Web

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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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Bootstrapped Unicorns: Entrepreneurship with Josh Pies About the Podcast Bootstrapped Unicorns is dedicated to Examining the Journey of Entrepreneurship. Interviews of entrepreneurs – finding out their back story, how they discovered their business, and how they overcame the challenges they faced, will help you – our viewers, friends, and peers – move forward with confidence. Josh Pies (Host), serial entrepreneur and guy who has hit both good and hard times, never gives up. What has fueled h ...
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Bootstrapped: In The Trenches

Michael Lee Rolland

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We’ve been in the food delivery industry since 2005 and have bootstrapped the entire way. While we compete with VC backed behemoths, this podcast gives listeners an idea about day to day life as an entrepreneur behind closed doors.
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Bootstrapped Growth

Bootstrapped Growth

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Welcome to Bootstrapped Growth where you will get actionable, tactical steps you can implement immediately to get results. No latest tips or tactics. No mindset training or feelings. Myself and the guests I bring on are going to share with you the most effective sales, marketing and business skills, strategies, and frameworks so you can repeatedly build a business in any economy.
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Welcome to the ultimate podcast for exploring *how to make money online*, *build a business on a budget*, and *leverage the best tools and resources* available in the digital marketplace! This show is your guide to understanding a variety of *online income streams*, including *affiliate marketing*, *eCommerce*, *freelancing*, *digital products*, and *passive income generation*. If you’re looking to start a side hustle, grow an entrepreneurial idea, or learn *proven strategies to boost your r ...
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My Bootstrapped SaaS

Tyler Lacy

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This podcast will follow my journey as I create https://www.reviewiply.com my latest bootsrapped SaaS. I will keep you updated on everything that goes on. How many customers, how many free trials, what is the MRR? All of the details you could want about my latest SaaS product.
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Backstage Capital is venture investment fund that backs underrepresented tech startup founders. Since inception in September 2015, Backstage has deployed nearly $2m into 40+ startups around the U.S. that are led by women, POC, and LGBT founders. This podcast takes you behind the scenes to show you what it's like to build a fund from scratch and give you deep insights into what investors are REALLY looking for. You'll laugh. You'll cry. You might steal a donut. But that'll have nothing to do ...
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The Power of Positive News: Community Journalism Entrepreneurship With Debbie Gunter | The Bootstrapped Unicorns Podcast Link to video podcast episode: https://youtu.be/V7hEBcHPOmc Welcome to the Bootstrapped Unicorns Podcast! In this episode, host Josh Pies welcomes Debbie Gunter, owner of a community newspaper based in College Park, Orlando. Debb…
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Coding with AI changes everything. It changes how we design, test, and improve our software projects. Today, I’m talking to generative AI expert James Phoenix. He’s written the book on prompt engineering and shares his hard-earned AI insights freely on the show — including a crash course in developing effectively with the Cursor IDE. Are developers…
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Arielle Nissenblatt, founder of the Earbuds Podcast Collective, shares her extensive experience in the podcasting and newsletter space, shedding light on the intersection of these two mediums. Starting her journey in 2017 with a podcast recommendation newsletter, Arielle initially aimed to help others discover quality content without the intention …
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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 …
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YouTube is both the best and the worst source of information — because we can watch it all, but no one will tell us what's REALLY worth watching. Here's how the gatekeepers have vanished, and what has taken their place. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what mat…
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From Family Ties to Team Trust: Building a Legacy In HVAC with AJ Munson | The Bootstrapped Unicorns Podcast | Episode 34 Link to video podcast episode: https://youtu.be/toqRh5SZZbk Welcome to the Bootstrapped Unicorns Podcast! Join host Josh Pies on this episode of Bootstrapped Unicorns as he dives into the world of family-owned businesses with hi…
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Bootstrapped Unicorns Podcast | EP 33 | Harnessing the "WE": Transforming Leadership and Business Culture with Kyle McDowell Original Publish Date: November 7, 2024 Link to video podcast episode: https://youtu.be/gWE1trRb6gA Welcome back to the Bootstrapped Unicorns Podcast! In this episode of Bootstrapped Unicorns, host Josh Pies of C47 Digital St…
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Bootstrapped Unicorns Podcast | EP 32 | Blueprint for Business Growth: Innovative Architecture, Entrepreneurship, and Empathy with Nathan Aleskovsky and Frank Davi, Jr Original publish date: July 2024 Link to video podcast episode: https://youtu.be/3tsdvxxXI6Y Thanks for tuning in to the Bootstrapped Unicorns Podcast! Welcome! Join us in this compe…
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Bootstrapped Unicorns Podcast | EP 31 | Entrepreneur's Edge: How Coach Pete's Playbook Elevates Small Businesses Original publish date: June 2024 Link to video podcast episode: https://youtu.be/C1JiyVNUNtU Welcome to the Bootstrapped Unicorns Podcast! In this episode of Bootstrapped Unicorns, host Josh Pies talks with business and performance coach…
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The problem with having no boss is that there's no one to stop you from procrastinating. I'm challenged by this daily, and I have found a few ways to stay accountable. I'll share those with you today. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them ou…
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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 c…
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I want new prospects to receive the maximum possible value the moment they register for Podscan, so I treat them as customers before they even come to the page for the very first time. Here's the Podscan Dream Customer strategy — from idea to execution. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works fo…
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Bootstrapped Unicorns Podcast | EP 30 | Barry Botwin's Altitude Adjustment: From Flights to Home Financing Original publish date: June 2024 Link to video podcast episode: https://youtu.be/SDIeml9K3pU Welcome to the Bootstrapped Unicorns Podcast! In this episode of Bootstrapped Unicorns, host Josh Pies interviews his friend Barry Botwin, a former co…
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Bootstrapped Unicorns Podcast | Episode 29 | A Life of Serial Entrepreneurship With Carey Sobel Original publish date: June 2024 Link to video podcast episode: https://youtu.be/2VB0GgVVtZo Welcome back to the Bootstrapped Unicorns Podcast! Join host Josh Pies as he explores the world of serial entrepreneurship with Carey Sobel, a dynamic guest -- w…
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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 B…
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Yesterday, I shrunk the size of my production database from four terabytes to just under one terabyte. Something interesting happened last weekend that made me realize I needed to change how I think about scale. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, ch…
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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 Jo…
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When a Podscan user got a bit "too general" with their keywords, all of a sudden, my email provider stopped sending emails. Whoops. Let's talk user error and founder foresight. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https:…
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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 "On…
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SaaS founders are simultaneously tenants and landlords, renting the tools we need while offering our own services for subscription. It's a world where true ownership seems increasingly elusive, yet understanding its nature is crucial for building lasting value. This episode is sponsored by Paddle.com — if you're looking for a payment platform that …
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Join Sarah St John and Nick Nahlbach as they dive into the transformative role of AI in the podcasting world, highlighting how tools like ChatGPT and Perplexity AI can significantly enhance content creation for podcasters. Nick shares his journey of exploring AI tools before the rise of ChatGPT, revealing how he and his partner recognized the poten…
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LINK TO YOUTUBE: https://youtu.be/lnYoAp9VHdY YOUTUBE CHANNEL: https://www.youtube.com/@BootstrappedUnicornsPodcast ORIGINAL RELEASE DATE: May 2024 RELEASE DATE: October 2024 EPISODE: 28 SHOW NOTES: Bootstrapped Unicorns Podcast Episode 28 | Designing An Ideal Life: Blueprints for a New Beginning with guest Jeanne Collins This episode of Bootstrapp…
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LINK TO YOUTUBE: https://youtu.be/PdAeEbiyybQ YOUTUBE CHANNEL: https://www.youtube.com/@BootstrappedUnicornsPodcast ORIGINAL RELEASE DATE: April 2024 RELEASE DATE: October 2024 EPISODE: 27 SHOW NOTES: Bootstrapped Unicorns Podcast Episode 27 | Crafting Your Exit: For Business Owners Looking Ahead with guest Laurie Barkman Ever wondered what it take…
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LINK TO YOUTUBE: https://youtu.be/aeLqPKlmACQ YOUTUBE CHANNEL: https://www.youtube.com/@BootstrappedUnicornsPodcast ORIGINAL RELEASE DATE: April 2024 RELEASE DATE: October 2024 EPISODE: 26 SHOW NOTES: The Bootstrapped Unicorns Podcast Episode 26 | The Cure Within: Finding Your Unique Remedy for Success and Fulfillment with guest Markus Kaulius Join…
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Bootstrapping is all about dealing with constraints: no money, the day job, lack of experience, and having no distribution. If you want to know how I tackle the restricted resources I am building Podscan on, this one's for you. Today, we'll dive into what drives my priorities and how they find their way into a complex platform that juggles a lot of…
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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: Jo…
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“I didn’t see it coming.” I had to admit that to myself a few times recently. Over the last couple of weeks, I've been experiencing several issues with Podscan that only came to pass because I didn't really have any observability on my system. At least that’s what I know now. Today, let me share my early-stage learnings about system observability i…
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ℹ️ Introduction Welcome to another insightful episode of *Frugalpreneur* with your host, Sarah St. John. Today, we're excited to have Liz Wilcox back with us. Liz, known for her prowess in email marketing and her dramatic survival on *Survivor*, where she placed 4th, brings a unique blend of reality TV insights and business acumen. We dive into her…
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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, Ro…
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AI is revolutionizing the way I work as a solopreneur. So why not share exactly how I use it? You'll hear how I use AI tools for everything from coding to marketing, and how they've become my secret weapon for punching above my weight. I also get into the nitty-gritty of the challenges and limitations of AI, and how I navigate them. If you're curio…
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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, Clarityflo…
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It started with a minor refactoring. It ended with an avalanche that almost caused an infrastructure explosion. From code to collapse — and a few weeks of frantic restoration. That's what Podscan was for the last 2 weeks. Here's why dealing with external data and its scale can be very dangerous for indie founders. This episode is sponsored by Podsc…
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Welcome back to another episode of Frugalpreneur, where we delve into the best tools and strategies for running a business on a tight budget. In this episode, we explore Captivate FM, a podcast platform designed to streamline your workflow and help you grow and monetize your show. Whether you're a podcasting novice or a seasoned pro, Captivate FM o…
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💡 Guest bio Joe Casabona, a software engineer by training and a natural extrovert, has found his true calling in podcasting. With a mind that operates like a computer, Joe harnessed his unique skill set to carve out a niche in the podcasting world. The pivotal moment came during the pandemic when Joe, who then had one small child and a wife working…
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LINK TO YOUTUBE: https://youtu.be/gQAjzYiil-A YOUTUBE CHANNEL: https://www.youtube.com/@BootstrappedUnicornsPodcast ORIGINAL RELEASE DATE: April 2024 RELEASE DATE: September 2024 EPISODE: 25 SHOW NOTES: Welcome to the Bootstrapped Unicorns Podcast! In this episode, host Josh Pies sits down with Scott Rammage, the founder of HireVP. They dive deep i…
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Welcome to the weird world of web scraping in the AI age, where founders have to protect their data from hungry AI companies but also need to collect information from all kinds of (not so) public APIs. Today, I dive into a particularly confusing situation I am in with Podscan when it comes to scraping and keeping the web free and open. This episode…
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LINK TO YOUTUBE: https://youtu.be/N6HiV1tauGA YOUTUBE CHANNEL: https://www.youtube.com/@BootstrappedUnicornsPodcast ORIGINAL RELEASE DATE: April 2024 RELEASE DATE: September 2024 EPISODE: 24 SHOW NOTES: Welcome back to the Bootstrapped Unicorns Podcast! We are thrilled this time around to welcome James Keyes to the show. He is a bona fide celebrity…
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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 Bri…
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Andrew Davies (@andjdavies) runs marketing for Paddle, the payment provider that powers several of my businesses. They also recently ran an AI launchpad accelerator, which massively impacted the trajectory of my business, Podscan. It's about time we chat more about money on the pod. Today, I get to talk to Andrew about all things payment, why a Mer…
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This week, instead of writing code, I delegated it — to AI. I've been doing this a lot lately. But does that mean I am losing my ability to code? And what about people learning how to code? Is AI serving them, or does it block them from learning the real thing? Here's what's happening in software development, if it's even worth bothering with, and …
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I gave up going to tech conferences. But that probably is an outdated opinion, particularly since as an entrepreneur, I benefit much more from hanging out with my peers. Here's what changed and why you should really consider going to these events if you're an indie founder. This episode is sponsored by Podscan.fm The blog post: https://thebootstrap…
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