Episodios

  • The Advantages of Serving the Little Guys with Andrew Stern
    Mar 31 2026

    Today, we’re joined by Andrew Stern, CEO of Quilt Software – not a fabric company, but a software company powering 20K+ specialty retailers across North America. We talk about:

    • The advantages of serving thousands of smaller customers, such as predictability
    • Providing users with actionable intelligence
    • Serving a highly varied client base
    • Bringing best-of-breed solutions to small market segments
    • Why the little guys are chronically underserved


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    30 m
  • The Possibilities & Threats of AI Agents with Evan Powell
    Mar 17 2026

    Today, we’re joined by Evan Powell, Founding CEO of DeepTempo, a pioneer in behavioral threat detection powered by deep learning. We talk about:

    • The cybersecurity problems – and solutions– resulting from AI
    • Possible continued existence of huge software companies generating high revenues
    • The source of SaaS value: The AI model or the software/code?
    • How to price SaaS apps when most users are AI agents
    • The proliferation of custom, homegrown software in enterprises


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    36 m
  • SaaS Revenue, Labor Substitution, & Durable Job Functions in the AI Era with Pete Hunt
    Mar 3 2026

    Today, we’re joined by Pete Hunt, CEO at Dagster Labs, building out Dagster, the data orchestration platform built for productivity. We talk about:

    • Challenges of determining software pricing with AI workers using apps
    • How barriers to AI adoption are similar to what we've known in SaaS for a million years
    • AI-driven shifts in the workplace [Many disciplines will look a lot more like engineering]
    • How outside sales is among the most durable job functions in the AI era
    • Advice for new college grads


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    35 m
  • Taking Small Saas Companies to The Next Level While Preserving What’s Good with Tim Schumacher
    Feb 17 2026

    Today, we’re joined by Tim Schumacher, Co-Founder of saas.group, a conglomerate of independent SaaS businesses founded by experienced industry veterans with proven entrepreneurial, investing, and product backgrounds. We talk about:

    • The new exit options saas.group brings to startups
    • Growing small SaaS companies while preserving what’s good & made them strong
    • Characteristics of successful startups, including lean companies with a very clear focus
    • Advice for SaaS founders – to sell or not to sell?
    • The SaaS market in Europe


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    36 m
  • Secure Virtual Access & How AI is Like Splitting the Atom with Jared Shepard
    Feb 3 2026

    Today, we’re joined by Jared Shepard, Chief Executive Officer at Hypori, a mobile access platform enabling secure virtual access to enterprise apps and data from any mobile device with total personal privacy. We talk about:

    • Jared’s journey from homeless high school dropout to tech founder
    • Solving hard problems, like edge compute in the military
    • The value of hybrid compute solutions, incorporating cloud and edge devices
    • Applying the elasticity of the cloud to mobile device use


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    31 m
  • The Premium Human Experience, with Anders Jones
    Jan 13 2026

    Today, we’re joined by Anders Jones, CEO and Co-founder of Facet, provider of impartial and valuable financial advice and services at an affordable membership fee. We talk about:

    

    • The future role of AI in financial advice
    • Decreasing headcount & SaaS spend due to building AI automation tools
    • The changing value proposition of software
    • The processes required for an AI agent to function effectively
    • Why building an AI wrapper on top of a platform is not a sustainable business model


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    31 m
  • Workforce Trends and Chasing the Shiny Object of AI with Doug Leeby
    Dec 16 2025

    Today, we’re joined by Doug Leeby, president and CEO of Beeline, the leading technology solution provider for managing the global extended workforce. We talk about:

    

    • What's happening with the extended workforce industry
    • The dearth of talent in cutting edge tech that plagues all of us
    • Rogue spending on talent in the enterprise
    • Building trust in autonomous digital AI agents
    • Tracking AI agents and assessing their output versus humans


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    31 m
  • Coping with the Discomfort of Hypergrowth with Adam Markowitz
    Dec 9 2025

    Today, we’re joined by Adam Markowitz, Co-Founder & CEO at Drata, the leader in AI-native trust management. We talk about:

    • The good problems that come with hypergrowth
    • The most critical decision that drives success
    • Being intentional about culture
    • The amplification effects of AI – and the risk that presents
    • Fostering a culture to support the discomfort of rapid growth


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    32 m