Episode 37 · With Cyrus · 12 Jun 2026 · 40 min

    What Makes a Traditional Business Worth Building On

    Modernising a traditional business is not about bolting AI onto it. It starts with the day in the life of the person doing the work.

    Featured guest

    Cyrus

    Investor, Shore Capital; formerly Open Ocean
    Cyrus was born in France and has spent the last twenty years in the UK. An engineer by training, he started his career at Salesforce before moving into venture capital, where at Open Ocean he backed what he calls AI-enabled services businesses, Coherent among them. He is now at Shore Capital, focused on the traditional economy, where he backs the acquirers rolling up and scaling small local businesses, primarily in the US.

    Show notes

    For the first time on the podcast, Jared sits down with a guest from outside the clinic: Cyrus, an investor who backs the people buying and building traditional, offline businesses. His thesis is that the unglamorous businesses underpinning daily life, from clinics to accountants to salons, are the least modernised part of the economy and the biggest opportunity in it.

    But value is not created top-down behind a spreadsheet or a deck; it comes from understanding the day in the life of the person doing the work. He argues a roll-up is really an integration game, won or lost on how well you align people rather than how cheaply you buy.

    On AI he is measured: the right question is never 'can this be automated' but 'what is the job to be done', and the answer usually lives in the details a ten-second pitch skips over.

    Key takeaways

    • The traditional economy is the opportunity: the unglamorous businesses that underpin daily life make up most of GDP and are the least modernised.
    • Value is built from the bottom up, not the top down; the work is to understand the day, week and month in the life of each role.
    • A roll-up is an integration game, not an acquisition game; the value comes from aligning people and systems afterwards.
    • Diligence starts with deceptively simple questions asked without assumptions.
    • AI is a 'job to be done' question, not a slogan.
    • It always comes back to the people on the other side of the table.
    “Either you take on the friction of discipline in the beginning, or the friction of regret at the end.”
    — Cyrus
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