Episodios

  • #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
    Oct 17 2025
    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 m
  • #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
    Oct 10 2025
    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 h y 2 m
  • #164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta

    #164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta
    Oct 3 2025
    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 m
  • #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
    Sep 26 2025
    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 h y 13 m
  • #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
    Sep 19 2025
    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 h y 1 m
  • #161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones

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

    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 m
  • #160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik

    #160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik
    Sep 5 2025

    Yuval Selik is co-founder and CEO of Promomash, a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who encountered the expensive, complex, and crucial process of managing trade promotions with stores and distributors.

    Promomash launched in 2015 to serve mid-sized CPG companies that don’t have custom software and their own teams to manage promotion spend and budget compliance with retailers. With 125 employees, they now serve over 500 customers with their software and optional analysts who can perform complex sell-through reconciliation and spend analysis.

    Yuval and his co-founder raised under $1 million from angel investors to get started, and the company is now profitable and growing steadily. Yuval also hosts The 7 Hats Podcast, which helps entrepreneurs master the seven key areas of their lives, ensuring both success and fulfillment.

    Quote from Yuval Selik, the founder and CEO of Promomash

    “That's really the reason why we did not raise funds from big investors, because I don't want to have the pressures of somebody on my board telling me that I have to grow 50%, 80%, or 100% year over year.

    “Sometimes you need to pull back in order to fix your product. Sometimes you need to push forward and step on the gas a little bit. But that decision needs to be my decision, not a VC investor’s decision.

    “Others in our market that raised big VC funding, in our competitive landscape. They are not run by their founders; they're run by their investors”

    Links

    • Yuval Selik on LinkedIn
    • Promomash on LinkedIn
    • Promomash website
    • The 7 Hats Podcast

    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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    1 h y 8 m
  • #159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield

    #159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield
    Aug 29 2025

    Vince Mayfield is cofounder and CEO of TalkingParents, a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who recognized the need for a secure, unalterable communication record to improve co-parenting and family harmony.

    He pitched a development company owned by Vince and Louis Erickson to build the first app. They came together to cofound TalkingParents in 2012. Stephen worked with judges, courts, and lawyers to build awareness and get their first customers. The app records and stores all communications between co-parents, including chats, message, phone calls, and calendars. The company started growing and eventually became profitable as word spread, they charged more for the product, and the app improved.

    TalkingParents is now a profitable and growing company with well over $10 million in revenue, 65 employees, 100,000 paying customers, and 500,000 people using the app. They are self-funded with no outside funding.

    Quote from Vince Mayfield, cofounder and CEO of TalkingParents

    “The company you are when you have 5 million in revenue and maybe 40 people, it's not the same company you are when you've got 20 million in revenue and say 80 people. It's not. You've got to iterate and change.

    “And you've got to have the stamina for that. You've got to be willing to put in the effort and do that. Yeah, exactly. There's no shortcuts to this.

    “I love it when people tell me, I've got an idea and I'm going to start up and it's going to go viral overnight. And my first thought is bulls--t. It's not going to happen that way.

    “It's much harder than everybody thinks. You hear about the overnight success, but what you don't see is the 10-year grind that it took to get there. And the sacrifice and delayed gratification that goes along.”

    Links

    • Vince Mayfield on LinkedIn
    • TalkingParents on LinkedIn
    • TalkingParent website

    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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    1 h y 4 m