The Dan Barrett Show

Dan Barrett

Join Dan Barrett—serial entrepreneur, business coach, and renaissance man—as he explores the intersection of business growth and personal fulfillment. This isn't just another business podcast; it's a journey into the art and science of building a life that's as profitable as it is purposeful. Drawing from his experience of growing a 7-figure marketing agency while pursuing diverse passions—from hypnotherapy to performing with critically acclaimed musical projects—Dan offers a unique perspective on entrepreneurial success. Each episode blends creative exploration with rigorous systems thinking, delivering insights that are both innovative and immediately applicable

  1. 21 AGO

    Transforming and Selling Businesses with Alexis Sikorsky, Part 2

    This week, Dan picks up with Alexis Sikorsky—entrepreneur, investor, and founder of Knight Scale Partners—for the tactical follow-through: what great private equity actually brings, how to replace yourself post-acquisition (“please chairman me”), why agility beats prediction in a world of Black Swans/“Black Dragons,” and how agencies can still win as AI re-sorts the field. If you’re navigating uncertainty, planning pivots, or gearing up for an exit, this continuation is packed with clear plays and hard-won context. Show Highlights What great PE actually brings: cost discipline, better people, and world-class sales—why the dream target has a weak or no sales team. [00:00:49] “Please chairman me”—why Alexis replaced himself as CEO and why being chairman can be the best job in the world. [00:02:07] Exit math that stuns: sold remaining shares for an undisclosed nine figures; two years later buyers resold for +60%, ~16× cash multiple. [00:02:36] [00:03:03] Retired, then Oxford: why he went back to school, started advising (even pro bono), and turned mistakes into a playbook. [00:03:52] Two superpowers: leadership (not management) and turning complexity into five actionable steps. [00:06:44] Triple headwind case study: clients dying, business model dying, channel dying—plus “Google is in panic.” [00:11:06] Pivot playbook: keep your domain (e.g., real estate), expand geographies, diversify inbound (podcasts/LinkedIn), and add warm outbound. [00:13:28] [00:14:41] AI won’t erase agencies—it will empower fewer winners (think 6,000 → 600); VCs shifting to AI-enabled efficiency. [00:15:28] Black Swans (“Black Dragons”): don’t time them—build agility and expect a crisis about every decade; a leveraged-forex cautionary tale. [00:17:36] [00:18:38] War-chest rule: keep ~9 months of burn so shocks don’t kill you. [00:20:14] Sci-fi as systems training: Asimov and a love letter to The Three-Body Problem (especially the brutal Book 3). [00:21:58] [00:23:33] Cashing Out: a simple method to go from small to less small—and how to speak private equity. [00:24:54] Where to find him: Knight Scale Partners (with a K), LinkedIn, and Instagram—unique name makes him easy to find. [00:26:56]   For more updates and my weekly newsletter, hop over to https://betterquestions.co/ To learn more about Alexis Sikorsky, check out the websites below:  https://www.knightscalepartners.com/  https://www.linkedin.com/in/alexis-sikorsky-consulting/?originalSubdomain=uk

    29 min
  2. 13 AGO

    Transforming and Selling Businesses with Alexis Sikorsky

    This week, Dan sits down with Alexis Sikorsky, founder of Knight Scale Partners, to unpack how to build, transform, and exit companies the smart way. Alexis shares the strategy behind “moving like a knight,” a crisp 3–4 year planning window with one-month reaction time, the metrics he watches, and the story behind selling his banking software company, why he took 85% cash / 15% earn-out, and how the earn-out ended up paying more. If you want a practical playbook for scaling value without losing your mind (or your house during a crisis), this is it. Show Highlights: Why the knight? Strategy behind Knight Scale Partners—anticipate, “play with the whites,” and win by moving differently. [00:03:02] The planning horizon that actually works: 3–4 years…with a one-month reaction time for pivots. [00:06:12] What to measure: start with TAM, then track LTV/CAC monthly—keep the dashboard simple. [00:11:05] Start with the founder’s goal: the surprisingly universal number is $40M and why. [00:17:23] (derived from the transcript section referencing “40 million”) 2008 hits: lost 75% of revenue in a day—and the seven-year grind back. [00:26:23] The deal that changed everything: 85% cash / 15% earn-out up front… [00:30:44] …and why the earn-out paid more than the cash. [00:31:10] What great PE actually brings: cost discipline and world-class sales; why “no sales team” is a PE dream. [00:32:02] Alexis’ two superpowers: leadership and turning complexity into five actionable steps. [00:56:27] “Black Dragons” (a.k.a. Black Swans): build 9 months of war chest and design for agility. [00:49:56] What Alexis reads for complex thinking: The Three-Body Problem (and The Dark Forest). [00:56:49] Cashing Out: Alexis’ simple method to go from ~$10M to $100M valuation; audiobook now available. [00:56:58] The Virtual C-Suite: fractional, high-caliber execs as an unfair advantage; early traction & LTV/CAC math. [01:07:03] For more updates and my weekly newsletter, hop over to https://betterquestions.co/ To learn more about Alexis Sikorsky, check out the websites below:  https://www.knightscalepartners.com/  https://www.linkedin.com/in/alexis-sikorsky-consulting/?originalSubdomain=uk

    32 min
  3. 25 JUN

    Connection Is the New Currency with Jason Yeh, Part 2

    This week, Dan picks up right where he left off with Jason Yeh, founder of Scaling Freedom, for a rapid-fire dive into the real-world side of AI. Jason shares battle-tested frameworks for deciding when to use AI (and when a simple script is smarter), explains why human connection will matter even more as automation spreads, and gets personal about parenting, education, and staying nimble in a market that changes every week. If you’re wondering how to weave clarity, technology, and meaning together—without losing the human spark—this conversation is for you.   Show Highlights Treat AI like a smart “drunk intern”—speak out loud, let it interview you, and watch the prompts improve [00:00:31] Build a custom GPT that turns raw thoughts into perfectly engineered prompts [00:02:37] “AI on a bad system just scales the mess”—why process always comes before tooling [00:04:36] The hidden gold mine of manual data entry and how scraping invoices unlocks insights [00:06:51] Jason’s 4-point litmus test for any AI project: Painful · Existing process · High impact · Strong data [00:09:56] Planner vs. Solver: use one “conductor” agent plus narrow specialists for higher accuracy [00:17:13]  Klarna’s chatbot fiasco & the lesson: some moments demand a human, not a bot [00:18:28] “Connection is the new currency”—brands that stay human will win customer loyalty [00:23:09] Staying nimble: why Jason refuses to ossify into a single product in a hype-driven market [00:24:45] The next frontier: AI-personalized education and raising kids who still think critically [00:28:12] Using Perplexity for curiosity walks and co-creating bedtime stories with your kids [00:32:37] For more updates and my weekly newsletter, hop over to https://betterquestions.co/ To learn more about Jason Yeh, check out the websites below:  https://scalingfreedom.ai/ https://www.linkedin.com/in/jasonjyeh/

    39 min
  4. 17 JUN

    Connection Is the New Currency with Jason Yeh, Part 1

    This week, Dan sits down with Jason Yeh, founder of Scaling Freedom, to talk about identity, resilience, and rediscovering purpose through AI. Jason opens up about going against expectations, getting laid off (again), and why community has become the most vital part of his entrepreneurial path. This is a personal and practical conversation on how Jason helps business owners bring AI into their work in ways that are human, useful, and deeply thoughtful — including a clear “Three A’s” framework you won’t want to miss. Don’t miss this if you’ve ever wondered how to connect clarity, technology, and meaning — especially in times of uncertainty. Show Highlights: Why Jason asks “What do you like to do?” instead of “What do you do?” [02:25] Growing up under pressure — and choosing his own way anyway [06:00] The defining moment: delaying graduation for a surprise study abroad [13:07] How getting laid off (again) led Jason to AI and entrepreneurship [17:24] The power of hiking, reflection, and reconnecting with community [20:13] Jason’s clear and useful “3 A’s” framework for AI: Automation, Answers, Advice [30:00] His #1 tip to beat prompt paralysis — “Have AI interview you” [34:14] Why connection is core to Jason’s business philosophy [27:22] For more updates and my weekly newsletter, hop over to https://betterquestions.co/ To learn more about Jason Yeh, check out the websites below:  https://scalingfreedom.ai/ https://www.linkedin.com/in/jasonjyeh/

    37 min

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Join Dan Barrett—serial entrepreneur, business coach, and renaissance man—as he explores the intersection of business growth and personal fulfillment. This isn't just another business podcast; it's a journey into the art and science of building a life that's as profitable as it is purposeful. Drawing from his experience of growing a 7-figure marketing agency while pursuing diverse passions—from hypnotherapy to performing with critically acclaimed musical projects—Dan offers a unique perspective on entrepreneurial success. Each episode blends creative exploration with rigorous systems thinking, delivering insights that are both innovative and immediately applicable

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