Investor Deep Dive

Investor Deep Dive
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Investor Deep Dive, hosted by Sarah Sterling and Alex Mercer, explores how early-stage decisions are actually made before outcomes are clear. Each episode breaks down execution choices, constraints, and readiness signals behind notable companies and operators — without pitch tactics or hindsight bias. Founders gain clarity on what investors really assess, Investors sharpen pattern recognition, and Accelerators see what truly moves readiness. Grounded in execution reality, not hype.

Episodes

  1. 3 DAYS AGO

    Turn Your Toughest Rejection Into a Billion-Dollar Success 🚀

    In this masterclass on strategic authenticity, we break down the incredible journey of Jamie Kern Lima, the founder of IT Cosmetics. 💄 Imagine being told by a major investor that nobody would buy makeup from someone who looks like you. Jamie didn't let that crushing rejection stop her. Instead, she used her struggle with rosacea to expose a massive hole in the beauty industry. 🚩 The Power of Vulnerability: How Jamie’s 10-minute live gamble on QVC shattered the "perfection" myth of the beauty world. Building a Trust Moat: Why a brand built on truth is more valuable than one built on fantasy. Strategic Authenticity: How to turn your perceived weaknesses into your greatest competitive assets. Jamie’s story culminated in a $1.2 billion sale to L'Oréal, proving that when you show the world your unvarnished reality, you don't just find a niche—you build an empire. 📈 Listen now on Spotify to discover how to flip the script on your own setbacks! 🎧

    11 min

  2. 27 JAN

    Calendly & The $3 Billion Secret of "Inherent Virality"

    "Can you do Tuesday at 2 PM?" 📧 We’ve all been stuck in that email scheduling nightmare. On this episode of The Deep Dive, join hosts Sarah Sterling and Alex Mercer as they decode the massive success of Calendly. How did a simple scheduling link turn into a company with a $3 billion valuation—without a massive marketing budget? The answer lies in "Inherent Virality." Sarah and Alex unpack the story of founder Tope Awotona, who risked his life savings to prove that the product itself should be the marketing. We break down the "Single-to-Multiplayer" formula, why Product-Led Growth (PLG) beats traditional sales, and how you can engineer a viral loop into your own business. Tune in to learn how to stop chasing leads and start building a product that sells itself.

    10 min

  3. 22 JAN

    Chobani’s high-stakes demand to secure space in the grocery store main aisle

    Welcome to the Investor Deep Dive Podcast, hosted by Sarah Sterling and Alex Mercer—where founders, investors, and operators unpack the real decisions behind category-defining companies. In this episode, we dive into Chobani’s high-stakes demand to secure space in the grocery store main aisle—a bold move that highlights the power dynamics between fast-growing consumer brands and established retail incumbents. We explore what this moment reveals about brand leverage, distribution strategy, and negotiating power, and why shelf placement can be just as critical as product quality or marketing spend. From founder conviction to retailer risk, this discussion breaks down the strategic trade-offs that matter to investors and operators alike. Whether you’re building a consumer brand, investing in CPG, or evaluating how scale shifts negotiating power, this episode offers sharp insights into how companies push for growth—and what happens when they challenge the status quo. 🎧 Tune in as we unpack the strategy, risks, and lessons behind one of the most talked-about retail power plays in modern CPG.

    8 min

  4. 13 JAN

    Judy Faulkner & Epic Systems: How a Founder Built a Healthcare Software Giant Without VC

    How did Judy Faulkner build Epic Systems into one of the largest healthcare software companies in the world—without venture capital or Silicon Valley influence? In this episode, we break down the extraordinary founder story of Judy Faulkner, CEO and founder of Epic Systems, the dominant electronic health records (EHR) platform used by leading hospitals worldwide. This podcast explores how Epic grew into a multi-billion-dollar healthcare technology company by rejecting VC funding, prioritizing long-term thinking, and maintaining founder-led control. You’ll learn how Judy Faulkner’s leadership philosophy, product-first mindset, and disciplined approach to scaling allowed Epic Systems to outperform competitors in health tech, enterprise software, and medical software markets—while remaining privately owned. This episode is essential listening for startup founders, SaaS operators, healthcare technology professionals, investors, and accelerators interested in alternative startup models, sustainable growth, and founder-led companies. In this episode, we cover: Judy Faulkner’s founder journey and leadership style How Epic Systems became a healthcare software leader Why Epic rejected Silicon Valley and venture capital Scaling enterprise SaaS without external funding Lessons for founders building durable, profitable companies 🎧 If you’re interested in startup podcasts, founder stories, SaaS growth, healthcare IT, electronic health records, or Epic Systems, this episode offers a powerful and practical case study.

    12 min
  5. The Investor Deep Dive Podcast

    7 JAN

    The Investor Deep Dive Podcast

    Episode 1 - Flawless UI - an Investor Red Flag I’m Sarah Sterling, and I’m joined by my co-host, Alex Mercer. Together, we’re peeling back the layers of the startup world to reveal what truly drives investment decisions. In this episode, we’re tackling a seductive trap that catches countless founders and even seasoned product teams: "Polishing the Turret." We’ve all seen it—the pitch deck with stunning UI, the app that explodes with beautiful confetti, and the frictionless onboarding that feels like magic. But what happens when that flawless exterior is hiding a business with zero market demand? Alex and I dissect a recent pitch that had everything going for it visually—museum-quality design, buttery smooth interactions—yet failed to secure a single dollar of funding. We explore why technical elegance often masquerades as viability, and why the most valuable signal for an investor isn’t a slick app, but an ugly spreadsheet proving customers are desperate for a solution. If you’re a founder agonizing over pixel-perfect buttons, or an investor trying to spot the difference between a real business and a "pretty trap," this conversation is for you. We’re going beyond the pitch deck to discuss: Why viability always trumps feasibility. How to build a "de-risked hypothesis" before writing a line of code. The counter-intuitive power of the Concierge MVP (and why doing things manually is your secret weapon). So, stop coding, step away from Figma, and join us as we uncover why the ugliest evidence is often the most beautiful thing an investor can see. Let’s dive in.

    15 min
  • 5 Episodes

About

Investor Deep Dive, hosted by Sarah Sterling and Alex Mercer, explores how early-stage decisions are actually made before outcomes are clear. Each episode breaks down execution choices, constraints, and readiness signals behind notable companies and operators — without pitch tactics or hindsight bias. Founders gain clarity on what investors really assess, Investors sharpen pattern recognition, and Accelerators see what truly moves readiness. Grounded in execution reality, not hype.

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  • Creator
    Investor Deep Dive
  • Years Active
    2K
  • Episodes
    5
  • Rating
    Clean
  • Copyright
    © Investor Deep Dive
  • Show Website
    Investor Deep Dive