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Show Notes
Guest: Scott Leese — Fractional CRO, 12 unicorns, 13 exits, six-time sales leader, five-time founder, three-time author, major LinkedIn community builder, newsletter publisher, and creator of multiple businesses.
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Early Days & First Hustles
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Grew up in a non-entrepreneurial household; sold baseball cards as a kid, had entrepreneurial “side hustles” in college.
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Spent much of his 20s battling and recovering from a life-threatening illness. Four years hospitalized, nine surgeries, struggled with painkiller addiction, read hundreds of books — which planted the seeds for future business curiosity.
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How He Got Into Sales & Startups
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First tech sales job at 27, encouraged by a friend who noticed Scott’s resilience, competitiveness, and leadership.
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Sales led to VP/CRO roles at high-growth startups, where Scott built and scaled revenue teams, eventually leading to multiple exits and unicorn valuations.
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Lessons on Sales as a Career
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Sales is a pure meritocracy: “If you produce, you get paid. If you don’t, you’re cut — just like athletics.”
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Outproducing others shouldn’t just lead to the same pay — sales rewards top performers more than most fields.
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Why Just Being a High-Paid Employee Isn’t Enough
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Even top execs at successful startups rarely see transformational wealth (example: after a $500M+ exit, the founder gets $20M+, a C-suite leader gets $500K).
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True wealth comes from moving from “employed” to “owner” — writing books, building communities, conferences, consulting, investing in real estate, launching multiple income streams.
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The Coming Disruption & Opportunity from AI
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The rise of AI means most entry-level sales/tech/white-collar jobs will disappear or change radically.
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The era of corporate security is ending; individuals must think entrepreneurially, diversify income, own their brand, and quickly adapt.
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Future sales: Only high-level, complex, relationship-driven roles will survive; all “boiler room”/transactional sales will be automated or handled by agents.
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As commerce increasingly digitizes, the most acute personal/professional needs will be (1) “inner work” (purpose, mental/spiritual health) and (2) experiences/community.
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Optimism & The New Wave
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Exponential growth in personalized medicine & health/longevity businesses (AI-powered diagnostics, genetic-driven treatment, biohacking).
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Massive new opportunities for anything that promotes genuine human connection or personal growth (retreats, mastermind events, experiential learning, spiritual/purpose-driven work).
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In an automated world, experiences and community will be more valuable (and defensible) than ever.
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Scott’s Personal Projects & Where to Connect
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