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  • #168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head

    #168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head
    2025/10/31
    In this episode, the founder of Practical Founders, Greg Head, shares the most powerful insights from over 165 podcast interviews and working with 40+ bootstrapped SaaS founders in his peer groups. Greg breaks down the common but less obvious traits he sees in practical founders who are quietly building valuable software companies without big VC funding. Greg shares how frugality and managed risk-taking coexist to create compounding steady growth, creating massive long-term value fpr practical founders. And independence and doing it your way are not just luxuries but real superpowers that fuel growth. These patterns have emerged across hundreds of founders he's worked with, representing over $10 billion in founder equity value created. For SaaS founders skeptical of VC templates and PE playbooks Greg shares what all practical founders do to grow from $1M to $10M ARR without betting it all. Are you wired like a Practical Founder? Key Takeaways Frugal yet bold – Practical founders are unusually frugal in life but make well-timed bold bets inside their companies.Managed risk – They avoid betting the whole company, instead making small bets that can compound into larger wins.Compounding focus – Long-term, steady 20–30% growth creates exponential outcomes in SaaS over 10–15 years.Independence premium – Protecting their ability to do it their way is treated as a strategic advantage.Optionality matters – Practical founders value flexibility to sell, go long, or change direction without outside control. This Interview Is Perfect For Founders building SaaS without VC fundingCEOs who value control and sustainable growthEntrepreneurs exploring long-term leverage vs. quick winsAnyone who wants to understand the practical founder mindset Quote from Greg Head, founder of Practical Founders "The simple math of a $1 million ARR recurring revenue business that grows at 30% a year, will become very valuable if it keeps growing. ? Not crazy growth, a reasonable pace. This is the fundamental principle of recurring revenue businesses, that it's a compounding machine. "If you grow at 30% for nine years, you'll have a $10 million business. And if you do that for another nine years, you will have a $100 million business. That's probably worth a billion dollars by that time. That sounds simple and not everybody gets there, of course, but practical founders think in this way. Steady, healthy compounding. "We know that in the long run, the 10 years, the 20 years, compounding makes the difference. It's a healthier approach. We actually like this approach, generally speaking. We understand the math and yes, we're doing it. Most people don't really sign up for this kind of thing." Links Greg Head on LinkedInPractical Founders on LinkedInPractical Founders website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    53 分
  • #167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl

    #167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl
    2025/10/24
    Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, Darryl started the company more than 20 years ago after careers at Fred Hutchinson Cancer Research Center. They built DFnet around long-term client relationships in global health and clinical research. The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical studies worldwide. With offices in the U.S., Canada, and South Africa, DFnet has grown to more than 50 employees and is approaching $10M in revenue. Clients range from the U.S. Department of Veterans Affairs to nonprofits like PATH and major universities. Still independent and bootstrapped, DFnet has made key moves to prepare for the future—such as bringing in a growth-focused CEO, diversifying beyond single-client risk, and shifting legacy software to SaaS and services. Darryl shares the lessons from running conservatively under debt, buying rather than building, and building a global company rooted in relationships and practical execution. Key Takeaways Stability First Growth – Carrying a 10-year SBA loan forced conservative growth and taught the discipline of stability over risky expansion.Buying Not Building – Acquiring DataFax brought 35+ new clients overnight and proved that buying legacy software can be smarter than reinventing.Services Plus Software – Unlike pure SaaS, DFnet thrives by combining consulting, hosting, and software in a regulated field.Spouse Founders Structure – Their 51/49 ownership split avoided deadlocks and kept marriage and business aligned. This Interview Is Perfect For SaaS founders balancing growth and controlFounders considering succession or saleBootstrapped entrepreneurs in niche B2B marketsAnyone curious about global health data and impact-driven tech Quote from Darryl Pahl, co-founder of DFnet "The best position to be in is to say that in three to five years, we would be crazy to sell this company. It's doing so well. That would be the perfect thing. And what we're not looking for is a giant payout. We have a very modest lifestyle. "But is an asset, it is a business, and there's a business aspect. It would have to be the right type of buyer. It has to be the right fit. It has to be the right person or group that is respectful to our clients, our employees, and us as owners. "So the ideal would be to have the luxury of either not selling or being more selective rather than responding to random emails from some financial buyer or search funder." Links Darryl Paul on LinkedInDFnet on LinkedInDFnet website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    1 時間 11 分
  • #166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico

    #166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico
    2025/10/17
    Vincent Serpico, veteran CTO and founder of Founders Workshop, is on the front lines of the AI revolution in 2025, reshaping software development and business operations. With more than 30 years of experience building software apps, Vincent is now dedicating himself full-time to AI coaching and workshops for teams and companies to create high-leverage impact quickly. Vincent shares how practical SaaS founders are leveraging agents, vibe coding, and tools like OpenAI's Agent Kit to multiply output without adding headcount. He sees the shift from SEO to GEO, the rise of ChatGPT apps, and why domain expertise is the ultimate competitive moat for SaaS founders navigating this new economy. Now leading Serpico.ai, Vincent describes how entire applications can be built without writing code, using natural language and iterative management. He stresses that daily AI use, human-in-the-loop workflows, and focusing on domain-driven innovation will give practical founders the edge in this seismic shift. Key Takeaways Agents As Labor – AI agents perform multi-step workflows like employees, delivering productivity gains with human-in-the-loop oversight.Domain Expertise Moat – Deep customer and industry knowledge matters more than raw coding speed in the AI economy.Vibe Coding Skills – Non-coders can now build apps with natural language prompts, managing AI like junior employees.Practical AI Adoption – Founders should start with small use cases, building workflows before tackling complex projects.Great Arbitrage Period – Founders who embrace AI now gain massive leverage over competitors who resist change. This Interview Is Perfect For SaaS founders ready to apply AI beyond experimentsProduct leaders exploring AI-driven workflowsDevelopers curious about vibe coding and agentic designFounders building lean, AI-powered teams Quote from Vincent Serpico, founder of Serpico.ai "If you're not an expert in something, AI will probably make you two to three times better than you currently are. But if you are an expert in something, AI will make you 10x better. "If you're already a domain expert, using AI will make you 10x better. Those are the ones that you should be hiring and paying outpaced salaries to, and build your tiny team—domain experts who are great at AI. "If I want to use AI in real estate, I could do it, but a guy who's been a real estate agent for 30 years will do much better if he understands AI skills like how to prompt and context engineer. "So we'll see hiring domain experts and paying them outsized salaries because they're utilizing AI and producing five, six times more than they could without it." Links Vincent Serpico on LinkedInSerpico AI website Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    59 分
  • #165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland

    #165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland
    2025/10/10
    Brett Gilliland, founder of Elite Entrepreneurs, joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations. He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong hiring practices, Elite Entrepreneurs has helped hundreds of founders become happy CEOs and build companies that run without constant founder involvement. Brett reveals the personal transformation required for founders to evolve into true CEOs who can enjoy their business more as it grows. You can reduce chaos, scale your teams, and rediscover the fun of running your business once you shift focus from "I" to "we." Key Takeaways Growth Brings Freedom: Founders who learn let go in the right way often rediscover fun, profit, and time.Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team. Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned.CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated.Hiring as Marketing: Culture-fueled job postings act like a "bat signal" for the right candidates. This Interview Is Perfect For SaaS founders at $1–5M in ARRBusiness owners feeling "stuck" at their current stageCEOs ready to build their first real leadership teamEntrepreneurs who want growth and a life Quote from Brett Gilliland, founder of Elite Entrepreneurs "All of us get stuck in some way. We know there's a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn't know what to do. "You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to 10 million. Here are the things that you do. It's proven, it's practical. "Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we're talking about, they start stacking wins. "Then all of a sudden, 18, 24 months later, we're at a place where we've tripled in revenue, we've doubled in team, it's fun, I've got some time back in my life. It does take time, but it's totally doable. I've seen it over and over and over again. Links Brett Gilliland on LInkedInElite Entrepreneurs on LinkedInElite Entrepreneurs website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    1 時間 2 分
  • #164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta

    #164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta
    2025/10/03
    Praveen Ghanta, founder of Fraction and former CEO of HiddenLevers, shares how he turned his experience scaling a bootstrapped SaaS company into a fast-growing fractional talent marketplace. After HiddenLevers reached $8M in ARR and sold for over $100M, he realized that senior fractional engineers were the secret to delivering efficiently without expensive full-time hires. Fraction now serves over 100 SaaS clients with a vetted pool of 500 senior U.S.-based engineers and CTOs. Typical engagements run 10–30 hours a week, helping founders tackle scaling challenges in vertical SaaS, AI engineering, DevOps, and legacy system conversions. The company has reached $10M ARR in just three years while keeping half its own team fractional. Praveen explains how clients use Fraction to save costs, speed development, and even prepare for M&A due diligence with fractional CTOs. He also highlights how AI has boosted senior developer productivity by 4x, why U.S.-only context matters, and how fractional-to-full-time hiring often becomes a win-win path. This interview is perfect for SaaS founders at $1M–10M ARR, hitting scaling issues, vertical SaaS leaders needing senior engineers without VC funding, and founders considering AI-powered product features and engineering talent. Key Takeaways Fractional Individual Contributors: Not just execs—senior engineers deliver hands-on code, marketing, and DevOps part-time.AI Productivity Boost: Senior developers using AI tools are delivering 2–4x more than peers without them.Cost Advantage: Starting at $5K/month, founders access senior dev talent without $200K+ full-time salaries.Best ICP Fit: Vertical SaaS companies at $1–10M ARR facing scaling issues or legacy migrations.Developer Productivity: Fraction leveraged its experience with over 100 clients to build DevHawk.ai, a tool that manages fractional talent and delivers results even more efficiently. This Interview Is Perfect For SaaS founders stuck at scaling challenges without a budget for big teamsBootstrappers and practical founders looking for senior engineering firepowerFounders facing legacy code, scaling issues, or AI feature rolloutsNon-technical founders struggling to manage offshore or junior dev teams Quote from Praveen Ghanta, founder of Fraction "There are a lot of very experienced engineers who get into a senior developer role, but if they're not going to become the manager of the team, there's not a really good and obvious career path for them. "They start to get bored because they know their job inside and out and it's relatively easy for them to keep delivering. "So working on a startup on the side is actually a way for both for them to sort of enrich their career and see new things and have that creative satisfaction, but at the same time, not take the risk. There are plenty of folks that want to be full-time at the startup, but there's risk in being at a startup." Links Praveen Ghanta on LinkedInFraction on LinkedInFraction website (fraction.work)DevHawk website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    57 分
  • #163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning

    #163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning
    2025/09/26
    Anthony Pierri and Rob Kaminski are the co-founders of Fletch, a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win. Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies. Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design. In our practical discussion, they help founders see that positioning is a business strategy, not copywriting, which forces clarity and tradeoffs to improve execution. They share why founders must (eventually) choose one clear path to scale efficiently and why bootstrapped SaaS leaders often make sharper bets than VC-backed peers. Key Takeaways Positioning = Strategy: Positioning is a founder/CEO choice, not copywriting or branding.Almost Universal Problem: Most B2B SaaS founders struggle with positioning clarity.Anchors Drive Focus: Use category, use case, or alternative as clear positioning anchors.Bootstrappers Move Faster: Limited capital forces clarity that VC-backed companies delay.Execution Takes Time: Positioning decisions are quick, but discipline drives results.Homepage Test: Your homepage clearly reveals whether positioning is working or not. This Interview Is Perfect For SaaS founders stuck at $1M–$10M ARR growth plateausBootstrapped operators needing sharper messaging to scaleFounders unclear about marketing vs positioning strategyB2B SaaS CEOs rethinking go-to-market focus Quote from Dave Yuan, founder of Tidemark Capital "There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company. "I don't care how narrow you get, the world's a big place. So even with a hyper-focused, verticalized niche, or use case play, there's plenty of money if you do it well and that's very appealing to bootstrappers. "Most VC-funded founders don't focus as well, which creates problems. But the founders who truly understand positioning and the idea that it can evolve over time, whether they're venture backed or not, they start with a very narrow practice to start and succeed as a leader. " Links Anthony Pierri on LinkedInRob Kaminski on LinkedInFletch Website Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    1 時間 13 分
  • #162: Practical Investor - What’s Working Now in AI-Driven SaaS Growth - Dave Yuan

    #162: Practical Investor - What’s Working Now in AI-Driven SaaS Growth - Dave Yuan
    2025/09/19
    Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful vertical software companies like Toast, ServiceTitan, Jane, and CCC. Tidemark hosts its annual VSaaS Collective Live Event, featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed. Dave also shares: Why software companies are getting real results with AI and are not waiting for the AI revolution--it’s here now.How AI-powered “systems of action” have undue influence with important users and can potentially displace entrenched systems of record software.How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion. Quote from Dave Yuan, founder of Tidemark Capital “There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue. “And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly. “To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing.“ Links Dave Yuan on LinkedInTidemark on LinkedInTidemark websiteVSaaS Collective Live event Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
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    1 時間 1 分
  • #161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones

    #161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones
    2025/09/12

    Dr. Matthew Jones is a licensed clinical psychologist who specializes in working with co-founders to help manage critical conflicts that threaten their success. He is the author of the book, "The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success."

    Matt has worked with hundreds of bootstrapped and VC-funded co-founder teams to help them repair and manage their relationships in the context of their growing business. In this episode, we discuss a wide range of co-founder relationship topics, including:

    • Why co-founder alignment sets the floor and ceiling for entire company culture and employee performance.
    • How most co-founder conflicts aren't about surface issues but deeper psychological needs for recognition and power.
    • Why research shows companies founded by friends are more unstable than those started by strangers.
    • The three communication languages of cofounders: operational (business), psychological (feelings), and archetypal (the vibe).

    Quote from Dr. Matthew Jones, a clinical psychologist

    "And those differences can start off and be quite positive. If we can manage that tension effectively. That's the magic of co-founders, right? Is the complementary skills and ways of operating that allows you to land somewhere even more effective than you could have individually.

    "But those same differences that give you that magic sauce also can be sources of friction, like an arthritic knee that just aches every now and then, and sometimes gets worse and worse, right? And so that's where the tensions really have to be managed. And so that's why I advocate for making those differences as conscious and explicit as possible."

    Links

    • Dr. Matthew Jones on LinkedIn
    • Cofounder Clarity website
    • Book: "The Cofounder Effect: How to Diagnose Fix and Scale Healthy Communication for Startup Success"

    The Practical Founders Podcast

    Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

    Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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    54 分