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Growing Pains

Growing Pains

Written by: Sean Languedoc
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About this listen

Welcome to “Growing Pains,” the podcast that cuts through the tech hype and gets real about what it takes to “grow up” with Venture and PE backing. Candid conversations, practical solutions, and a lot of “tell it like it is”.

This Podcast prepares you for the changes from new, professional investors. The good the bad and the very ugly.

Guests include CEOs, GTM experts, Operators, and Investors who talk about rapid scaling, changing leadership, ripping apart the tech that got you there, while not missing a beat to keep customers happy, disciplined reporting and forecasting with stories and anecdotes that make it real.

We’ll chat with experts who’ve crossed the scaling chasm and experts in PE and VC who about what they’ve seen post-investment and what they look for based on that experience.

So, if you’re ready for some honest, no-nonsense insights and maybe a chuckle or two, join us!

This is “Growing Pains” by Outforce, subscribe today, and let’s get started.

© 2025 Growing Pains
Economics Leadership Management Management & Leadership
Episodes
  • DAVID HORNIK, Lobby Capital and his 5x Billion dollar picks
    Jun 17 2025

    Meet David Hornik, the Silicon Valley legend who turned 5 companies into billion-dollar powerhouses—including Splunk's $28B exit to Cisco

    What You'll Learn:From Courtroom to Cap Table: How a lawyer pivoted into one of tech's most successful investors (and why his legal training became his secret weapon) • The People-First Formula: Why Hornik backs entrepreneurs, not just business plans—and how this philosophy created billions in value • AI Revolution Insights: What the investor who spotted enterprise software gold early thinks about the current AI boom • Work-Life Integration: How a top-tier VC actually manages to be present for his family (spoiler: it's not what you think) • Raising Creative Kids: The unconventional parenting strategies of someone who spots innovation for a living • Diversity = Dollars: Why inclusion isn't just nice to have—it's a competitive advantage that drives returns

    The Bottom Line: David doesn't just invest in companies; he invests in people solving problems that matter. After 25+ years in the game, his track record speaks for itself: Splunk ($28B to Cisco), GitLab ($15B peak), Bill.com ($5B), and counting.

    Perfect for: Entrepreneurs, investors, and anyone curious about what it really takes to build game-changing companies in Silicon Valley.

    Warning: Contains zero startup clichés and 100% authentic insights from someone who's actually done it.

    Chapters

    00:00 Intro and Beginnings with Yahoo

    01:52 Missing Uber

    03:48 Other Bets, Splunk, Bill.com, Faros.ai

    09:28 How David assesses the Entrepreneur and the Biz

    10:50 How AI changes the pitch

    12:59 Data + AI = Moat

    19:14 Lobby Conference

    21:26 DEI today

    22:25 From 2000-2025 what's old is new again

    25:08 Humans and Ai

    27:56 David and the Arts

    31:04 Life Lessons on Balance and attention to life


    For more insights from Sean, visit OUTFORCE.AI

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    36 mins
  • Chris Hood: AI Hype vs Reality
    Jun 10 2025

    Summary

    Would you want a human brain surgeon or the latest AI robotic surgeon to perform surgery?

    In this episode of Growing Pains, Chris Hood former director of innovation at Google, author of Inf-AI-lable , talks about AI's implications for businesses, particularly in customer-centric approaches. Chris presents a contrarian view that while AI has made significant strides, it is not near where the hype claims it to be. Chris argues that what has really changed is distribution to consumers - but not the science.

    He talks about the ethical considerations surrounding its use in critical fields like law and medicine and the importance of self-knowledge in navigating its future implications.



    Takeaways

    AI has been around for over 60 years, but its accessibility has changed recently.
    The hype around AI (promoted by investors and AI companies) often overshadows its actual capabilities.

    Starting with technology (often thin wrappers) rather than customer needs and deep domain knowledge can lead to failure.

    Companies should provide options for customer interactions, balancing AI and human support.

    Understanding the limitations of AI is crucial for businesses. Context sharing in AI interactions is crucial.

    Rapid AI advancements outpace regulatory measures.

    Bias in AI tools can affect decision-making. Diverse AI perspectives can enhance creativity.

    Self-knowledge is vital in understanding AI's impact.

    For more information visit

    Chrishood.com

    Outforce.ai



    For more insights from Sean, visit OUTFORCE.AI

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    48 mins
  • David Rowley Diversis Capital; The first 100 days and (Tech Team) Due Diligence
    May 27 2025

    David Rowley, Operating Partner with Diversis Capital (Diversis.com) discusses the intricacies of private equity, focusing on growth equity and the role of technology in investment decisions.

    He emphasizes the importance of understanding a company's technical leadership and team dynamics during the due diligence process.

    David also outlines the critical first hundred days post-acquisition, highlighting the need for a transformation plan and the impact of AI on investment strategies.

    Key Takeaways

    • Private equity firms have unique approaches to investment.
    • Technology can be an asset or a liability in acquisitions.
    • Understanding a company's history is crucial for future growth.
    • Leadership assessment is key during due diligence.
    • The first hundred days post-acquisition are critical for success.
    • AI is becoming integral to investment strategies.
    • Diversity in teams can enhance adaptability to change.
    • Effective communication between engineering and product is essential.
    • Evaluating technical leadership helps in understanding team dynamics.
    • Investment decisions are influenced by market dynamics and company performance.

    Chapters

    • 00:00 Introduction to Private Equity and Technology
    • 02:54 Understanding the Due Diligence Process
    • 05:36 Market Dynamics and Acquisition Strategies
    • 08:15 Evaluating Technology and Team Dynamics
    • 10:47 The Importance of Technical Storytelling
    • 13:34 Assessing Team Capabilities and Leadership
    • 16:06 Navigating the First Hundred Days Post-Acquisition
    • 18:44 Organizational Design and Conway's Law
    • 23:53 Understanding Conway's Law and Architectural Bias
    • 24:59 The Importance of Diversity in Engineering Teams
    • 26:37 Navigating the First Hundred Days Post-Acquisition
    • 35:27 The Role of AI in Due Diligence and Investment Strategies
    • 39:44 The Future of SaaS in an AI-Driven World

    Diversis.com Partners with technology companies to accelerate growth

    For more insights from Sean, visit OUTFORCE.AI

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    43 mins
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