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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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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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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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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 salient point of this podcast episode revolves around the profound significance of differentiation in business, articulated through the lens of the X Factor Effect methodology, co-created by our esteemed guest, Daniel Den. He elucidates how this methodology has empowered over 20,000 clients and students to elevate their entrepreneurial ventures…
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Surviving to Thriving: How Early Trauma Can Shape Successful Leadership | Bootstrapped Unicorns Podcast | Episode 46 Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring stories and actionable tips aimed at making you…
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When I started Podscan, I wanted to go full local AI. Self-hosted, self-managed, self-serving. But that tune has changed. Here's what to think about when contemplating a local AI strategy. The blog post: https://thebootstrappedfounder.com/when-to-choose-local-llms-vs-apis-a-founders-real-world-guide/ The podcast episode: https://tbf.fm/episodes/390…
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In this episode, I talk about how I'm using podcasting as a business tool. Not as a guest, not to promote my product, not as an advertiser, but as a way to build up and strengthen my network amongst my "Ideal Customer Profile" in the video games industry. Mentioned in this episode: Feature Upvote, my SaaS product The Community Lounge, the podcast I…
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[00:00:36] Intro: ChatGPT as a traffic driver and Chirag’s early insight [00:01:48] Revenue Numbers and Profitability of Taco [00:02:24] Personal investment strategy and non-AI assets [00:03:36] How Chirag uses AI agents to replace writers and boost efficiency [00:05:42] What makes Taco a true AI-powered agency [00:07:03] Tracking brand rankings in…
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This podcast episode elucidates the transformative power of writing and publishing a book, particularly for coaches and business owners seeking to establish their authority and expand their reach. Our esteemed guest, Meg Calvin, shares her extensive experience in assisting individuals to craft, market, and sell their Amazon bestselling books, shedd…
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It's time. Solopreneurship works for a while, but it can't last forever. Not for me, not for Podscan. We need help. The blog post: https://thebootstrappedfounder.com/the-founders-first-hire-when-to-let-go-of-your-weaknesses/ The podcast episode: https://tbf.fm/episodes/389-the-founders-first-hire-when-to-let-go-of-your-weaknesses Check out Podscan,…
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In this podcast episode, we engage in a profound discourse with Keri Lynn, a multifaceted podcaster and energetic coach, who elucidates the necessity of cultivating a holistic approach to personal development. Central to our discussion is the concept of the "five bodies," encompassing the energetic, physical, mental, emotional, and spiritual aspect…
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PMF is MIA without JTBD. Make sense? :D The "job to be done" sits at the core of my customer's use of my product. I need to understand it to understand them. To fathom their needs. This week, I'll share how I approach that — and why it's taken me years to get here. The blog post: https://thebootstrappedfounder.com/the-job-to-be-done-understanding-c…
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[00:00:00] Quick Montage (Growth, Grit, Vision, Revenue, Meaning of 1440) [00:00:36] Intro: Why 1440 is Different [00:01:48] Revenue Numbers and Profitability [00:02:24] How They Funded Without Venture Capital [00:04:48] How Big Can an Email Newsletter Get? [00:05:15] Why They Ignored Advice to “Go Niche” [00:06:09] 1440’s Thesis: Inch-Deep, Mile-W…
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The salient point of today’s discourse revolves around the assertion that there exists no unfavorable time to invest in real estate; rather, it is the strategy employed that dictates success amidst varying economic climates. In our conversation, I was privileged to host Patrick Francey, a distinguished figure in the real estate investment realm and…
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API docs used to be by and for developers. Now, non-technical people use AI tools to build integrations into our SaaS products. We need to rethink how we communicate with them (and the AI agents that write their code). The blog post: https://thebootstrappedfounder.com/your-api-documentation-is-not-for-developers-anymore/ The podcast episode: https:…
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Reinvention, Empowerment, & Bold Steps | Bootstrapped Unicorns Podcast | Episode 45 with Leigh Burgess Link to video podcast episode: https://youtu.be/jtU6jZPy8hw Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring s…
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I want to tell you what's happening with my product, Feature Upvote, over the last year or so. I've dramatically changed the positioning, to be a feedback management platform for the video games industry. Here's the story of why I repositioned - and how I did it. Check out the new "video games industry"-focused Feature Upvote home page.…
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In this enlightening discourse, we delve into the transformative journey of Teresa McBratney, a seasoned entrepreneur and spiritual business mentor, who underscores the paramount importance of authenticity in entrepreneurship. Teresa elucidates her evolution from a successful venture in the housing industry, which faced insurmountable challenges du…
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This week, I'm sharing behind-the-scenes choices that allowed Podscan's growth from a small experiment to a thriving business. I'll delve into the choices I've made and how some have worked better than others. I'll explore the key decisions that have driven our success, such as selecting the right tools and technology, and utilizing AI to enhance t…
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What Is Hippie Capitalism? | Bootstrapped Unicorns Podcast | Episode 44 with Kay Rawlins Link to video podcast episode: https://youtu.be/yh3caQPlKT0 Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring stories and act…
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The point of our discussion revolves around the evolution of Fanlist, previously known as Pod Inbox, and the strategic decisions that informed its transformation into a comprehensive platform for creators. In our dialogue, I had the distinct pleasure of engaging with Pat Cheung, the founder and CEO of Fanlist, who shared his journey from a successf…
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Just how much of your service should a trial user be allowed to "try"? When it costs you real money to supply your product, when and how do you apply limits so that people have to upgrade? That's my challenge this week, and I'll share a concrete example from my journey with Podscan. The blog post: https://thebootstrappedfounder.com/the-balancing-ac…
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In this podcast, we engage in a profound discourse with William Holsten, an accomplished inventor and entrepreneur, who elucidates the pivotal lessons encapsulated in his book, "Uh Oh: Avoid Unintentional Blunders That Derail Entrepreneurial Success and Goof-Proof Your Business." The central tenet of our conversation revolves around the concept of …
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Podscan is profitable. Wild. A great success, a year after starting the business, and a fun opportunity to look at the options that lay before me. What will be my next milestone? What's the ultimate goal here? Well, you'll hear all about it today. The blog post: https://thebootstrappedfounder.com/podscans-profitability-milestone-whats-next/ The pod…
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Last week, in my hotel room just after MicroConf, I got excited about repositioning. I have had some time to think about the steps forward since then, and here's what I've come up with. This week, I dive into what I have already done, what needs to be done next, and where this is going. The blog post: https://tbf.fm/episodes/383-repositioning-podsc…
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How I Started a Pro Soccer Team | Bootstrapped Unicorns Podcast | Ep. 43 with guest Kay Rawlins link to video podcast episode: https://youtu.be/lQSz4kKanEA Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring stories …
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And I have a few things to say. In one of my rare directly-from-the-hotel-room-to-you episodes, I'll dive right into the many wonderful experiences of this uniquely amazing conference, and I'll share my biggest learnings with you right here. The blog post: https://thebootstrappedfounder.com/i-went-to-microconf-in-new-orleans/ The podcast episode: h…
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The rise of AI is fundamentally changing and challenging the classic laws and principles of software development and entrepreneurship. Drawing from my experience building Podscan.fm with AI assistance, I dive into how laws like Conway's Law, Brooks' Law, and Postel's Law are being transformed in this new era of AI-assisted development, while sharin…
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How to Find Startup Investment Funds with Markus Kaulius | Bootstrapped Unicorns Podcast | Episode 42 Link to video podcast episode: https://youtu.be/BeZ0s4atocI Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring st…
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[00:00:00] Introduction [00:00:45] Early Adoption of Generative AI & GitHub Copilot [00:01:30] Discovering How Code Comments Improve AI Suggestions [00:02:33] Skepticism About AI Hype & Fear of Being Left Behind [00:04:03] Seeing a YouTube Tutorial That Unlocked Building a RAG Agent [00:05:06] Building His First Agent in One Week (and Feeling “Bad …
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When I talked to Anne-Laure Le Cunff earlier this week, we get into experiments and how to run them effectively. That made me think that I've been running quite a few of those recently, and here's how that has worked out for me. The blog post: https://thebootstrappedfounder.com/experiment-report-trying-new-things/ The podcast episode: https://tbf.f…
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Anne-Laure Le Cunff (@neuranne) is a neuroscientist and author of the book Tiny Experiments, where she shines a scientific light on how we set goals, what experiments we should think about, and how we can deal with uncertainty in a high-stress world. We chat about goals, reprogramming your own subconscious, and how learning in public can benefit an…
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[00:00:00] Intro & Evolving Work Relationship [00:01:03] Balancing Andrew’s Creative Side vs. Business Demands [00:02:06] Integrating Different Approaches from Teammates [00:02:33] Identifying and Staying in Your “Zone of Genius” [00:04:03] Tasks That Energize vs. Tasks That Drain [00:05:06] Struggle With First Drafts & Delegation [00:06:09] Commit…
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I'm not usually trying to create FOMO in other founders — I know all too well that we're busy enough with what we're building. But if you're not using chat-based AI to collaborate with (both in your business and outside of it), you're playing the game on hard mode. I'll share a few stories today of why this particular kind of virtual collaborator h…
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The most insidious consequence of chasing virality isn't that it makes you look foolish; it's that you're actively poisoning your precious audience. Here's what "playing the algorithm" might do to (instead of for) your personal and professional brand. The blog post: https://thebootstrappedfounder.com/virality-is-poisonous/ The podcast episode: http…
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Justin Moore (@justinmooretfam) knows a thing or two about sponsors. He's responsible for dozens of episodes of this very podcast to be sponsored! And what he taught me, he'll teach you. I was VERY hesitant when I started looking at sponsors. I thought that would dilute my brand. Make me a sellout. But that's a self-limiting belief — and Justin wil…
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When notifications prevent you from focusing on your actual work, you know you're in trouble. Here's how I approach the balance between keeping an eye on the critical parts of the business and focusing on the deep work that needs to get done. The blog post: https://thebootstrappedfounder.com/mute-those-dings/ The podcast episode: https://tbf.fm/epi…
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Databases are hard. Making the right choices early and keeping things running smoothly even when budget pressures and customer requests start piling on — that's the hard part that many solopreneurs and indie founders struggle with. I certainly do. So here's a journey through my learnings and experiences from running SaaS offerings with sizeable —ta…
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From the Classroom to Contracts with Nicole Cooper of Gem Hunter Property Solutions | Bootstrapped Unicorns Podcast | Episode 41 Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring stories and actionable tips aimed a…
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Sometimes, less is more. Here's how I pruned my feature backlog from 120 to 15 items. I'll share my decision-making framework; every single rule comes with examples. Time to cut down on the mental load that is having too many "ideas" in your backlog. The blog post: https://thebootstrappedfounder.com/deleting-your-backlog-a-founders-guide-to-feature…
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Sweet Dreams Come True with Ashley and Israel of Phat Ash Bakes | The Boostrapped Unicorns Podcast | Episode 40 Link to video podcast episode: https://youtu.be/G-dDb0d4hOY Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with in…
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One day, we'll all meld our minds into one, sharing our thoughts like the Borg on Star Trek. But before that, we have a few things to get done. And for us founders, that's dealing with the ever-increasing speed of technological advancement. The blog post: https://thebootstrappedfounder.com/indie-hacking-the-singularity/ The podcast episode: https:/…
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Brian Sierakowski (@bsierakowski) has been busy over the last year: he started working on ChangeBot and TRMNL, and both projects are taking off. If you ever wondered what a good changelog looks like or why you might need one, this episode is for you. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for y…
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This week, I was super sick — to the point where all I could do was rest in bed. The businesses needed to keep running, though. And fortunately, I set them up to do just that. The blog post: https://thebootstrappedfounder.com/building-systems-that-work-while-you-dont/ The podcast episode: https://tbf.fm/episodes/370-building-systems-that-work-while…
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Expectations around AI tooling are changing, and software founders will be the first to either provide what people want — or perish. 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://thebootstrappedfounder.com/expect-ai-tions…
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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…
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Johannes Jäschke is a pioneer in the intersection of technology and mental health. From a college seminar to the forefront of digital well-being, Johannes developed Hypnu, a hypnosis app that gained significant traction during the pandemic. His innovative approach offered an alternative to traditional methods, addressing insomnia and anxiety withou…
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Find Your Strategy: Mastering Sales with Jon Alwinson | The Bootstrapped Unicorns Podcast Link to video podcast episode: https://youtu.be/CdmNArSyMAY Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies of C47 Digital Studios, and join the conversations filled with inspiring stories and ac…
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