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Practical Founders Podcast

Practical Founders Podcast

Written by: Greg Head
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 Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.2025 Scaling Point LLC Economics Leadership Management & Leadership
Episodes
  • #184: Fixing The Software Development Mess For Non-Technical Founders - Keith Shields

    #184: Fixing The Software Development Mess For Non-Technical Founders - Keith Shields
    Feb 20 2026
    Keith Shields is co-founder and CEO of Designli, a custom software development company that's helped non-technical founders build over 200 digital products in 13 years. After struggling to build apps through unreliable agencies in his own early startup, Keith focused on fixing the many painful experiences most founders have when hiring software development teams. Designli operates as a complete outsourced engineering department for practical software founders building SaaS and AI products, mobile apps, and web applications. Their SolutionLab program means founders invest $13,800 in a 2-week design sprint of prototyping and product planning before committing to full development, reducing the risk of expensive failures that plague most custom dev projects. The company focuses primarily on vertical SaaS founders who understand their industry problems intimately but lack technical expertise. Keith recommends velocity to first revenue over perfect features, outside audits for struggling teams, and getting gut checks on your development situation, which is far less risky than making huge changes blindly when you feel stuck. Key Takeaways Black Box Risk: Most agencies operate in the dark, leaving founders guessing what's being built, why it's late, and whether progress matches expectations.Dedicated Teams Win: Full-time focused developers outperform fractional freelancers because context, ownership, and velocity compound over long projects.Get Clarity Fast: Structured upfront design sprints align founders and teams on scope, timelines, and priorities before heavy coding begins.Audit Early: A quick external code and process audit can reveal hidden problems before they turn into year-long setbacks.Trust Your Gut: If a development relationship feels wrong, get an outside perspective and fix it before making risky, large changes. Quote from Keith Shields, CEO and Co-Founder of Designli "My advice for non-technical founders that already have a product is to trust your gut when you ask, Are we getting the value out of our development team in this situation? "If you already have a product and your dev team isn't working, get an outside perspective. It's not that hard to go and get what you're doing audited by people, sometimes for free, like us, or you pay for it. You send off a copy of your code in a zip file. It doesn't even have to be the living, breathing version and say, Can you audit this and give me a gut check? "Getting an outside review of your code doesn't happen that often, surprisingly. People feel stuck in their frustrating situation until they make a huge change, and then it's a risky, huge change. So get some outside perspective early and often." Links Keith Shields on LinkedInDesignli on LinkedInDesignli 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 hr and 4 mins
  • #183: Selling to the Gorilla: Snap's Strategic Exit to ICE Mortgage Tech - Will Caldwell

    #183: Selling to the Gorilla: Snap's Strategic Exit to ICE Mortgage Tech - Will Caldwell
    Feb 13 2026
    Will Caldwell started Snap after his first real estate software startup fizzled, pivoting from agent tools to regulated compliance data. He discovered lenders were required to buy hazard and flood certifications, and realized this was a "painkiller" product. He built Snap as a data and analytics platform for real estate and mortgage underwriting. Snap grew from a single California compliance product into a national flood data business, reaching $5M in revenue and 30 employees. The company charged per-loan transaction fees and embedded via API into mortgage software systems. With double-digit market share, Snap focused on customer experience, automation, and expanding wallet share inside lenders' workflows. In October 2024, Snap sold 51% of the company to Intercontinental Exchange, parent of ICE Mortgage Technology, at a double-digit revenue multiple. Will stayed on to scale the platform inside a much larger ecosystem. His key lesson: dominate a narrow niche, build a required product, and let strategic buyers find you. Key Takeaways Required Beats Optional – Legal compliance products create urgency and retention because customers must buy to complete revenue-generating transactions.Micro-Niche Entry – Starting in a narrow regulated segment let Snap win trust, then expand into much larger adjacent markets.API = Distribution – Embedding inside legacy systems turned Snap into a one-click button that scaled through partners' existing sales teams.Customer Experience Wins – In commodity data markets, faster, cheaper, simpler delivery became Snap's main competitive weapon. Quote from Will Caldwell, CEO and Co-Founder of Snap "You don't need to build a huge business to get a huge, life-changing exit. Just stay laser-focused. Don't chase shiny objects. I see many founders trying to boil the ocean. It is about staying focused on a single niche. "I think vertical SaaS has many great niches, and horizontal software is challenging. You need a lot of money to go after horizontal solutions across industries. However, with vertical SaaS products and niches, there is a lot of overlooked opportunity; the real estate vertical is one prime example." Links Will Caldwell on LinkedInSnap on LinkedInSnap website Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned. If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system. Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools. Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan. 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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    52 mins
  • #182: Why Focus Beats Funding in Crowded SaaS Markets - Luigi Mallardo

    #182: Why Focus Beats Funding in Crowded SaaS Markets - Luigi Mallardo
    Feb 6 2026
    Luigi Mallardo joined Woffu as an early angel investor and later became CRO, helping founder Miguel Fresneda shape a practical SaaS growth path. Based in Barcelona, Spain, Woffu has built a modern cloud-based time and attendance platform for SMEs and mid-market companies, replacing legacy tools and spreadsheets with a focused, mobile-first workforce solution. Starting from just €2K MRR, Luigi led growth first through inbound, then outbound, and partner channels, increasing average revenue per account five to seven times. By 2025, the company reached nearly €500K in monthly recurring revenue, or about €6M ARR, with more than 50 employees and profitable, efficient growth across Spain. Woffu sold to Visma in 2022 following a multi-year, proactive exit strategy, with a total reported value of €20–30M including the 3-year earnout. Luigi shares how early focus, diversified revenue, and optionality shaped every decision. His biggest lesson: clarity about your endgame determines your strategy early on, including your growth model and many other important decisions. Key Takeaways Strategic Focus - Choosing one clear use case and market unlocked faster growth than chasing horizontal HR suite ambitions across Europe.Optionality First - Designing for multiple future paths gave founders leverage rather than forcing a sale based solely on valuation.Revenue - Layers Inbound, outbound, and partners created resilience while steadily raising average contract value and predictability.Exit Readiness - Warming buyers years early turned selling into a strategic process rather than a rushed financial event.Customer Success - Investing deeply in retention created low churn and made Woffu more attractive to long-term acquirers.Builder Mindset - Great CROs zoom in and out, connecting go-to-market execution with strategy, culture, and long-term outcomes. Quote from Luigi Mallardo, Chief Revenue Officer at Woffu "We chose our focus of ICP and focus of use case, to reduce the space of market optionality to get more business optionality. You see what I mean? "The advice I give most often is to focus, which doesn't mean to close off the option of having more verticals forever, but you need 75% or 80 % of your pipeline on where you are already monetizing and building traction. And then you leave that 20 % of pipeline to do experimentations in a new vertical. "It's one of the historical challenges, especially with young founders: the feeling of losing opportunities if they decide and don't do everything. But you are losing opportunities if you go too wide and you don't focus. Just be patient, postpone, and focus on what works." Links Luigi Mallardo on LinkedInWoffu on LinkedInWoffu website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors. Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals. 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 hr and 3 mins
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