#515 Zack Tomlin: Why most business advice fails you?

Zack Tomlin is a former founder who spent 12 years building and exiting a business, and we spoke about why most business advice doesn’t actually work for individual leaders. He’s also the author of Craft: The Expedition of Business, a book he repeatedly referenced throughout the conversation as a practical guide to mastering decision-making, leadership, and the craft of business. His core argument is simple: most advice is built for an “average business,” but “most businesses aren’t your average business” because they’re shaped by unique leaders, teams, and markets.The turning point in his journey came from realizing that copying others only gets you so far. He describes leadership growth as a climb—from mimicry, to heuristics, to frameworks, and finally to first principles. As he puts it, “the best business advice is one that is built on principles that are true for all business,” but it’s the leader’s job to translate those into decisions that actually fit their reality. He also reframes scaling: instead of treating a company like a machine that “erodes and rust[s] and breaks down,” he advocates designing it as an environment—an ecosystem where the right behaviors emerge naturally.Practically, Zack breaks business into four parts: destination (clarity and beliefs), crew (who you hire), leader (your mindset shift), and expedition (systems that run without you). He highlights that growth pain often hits between 10–200 employees, when communication breaks down and leaders must transition from doing the work to enabling others. Constraints—competition, time, money, and human limits—aren’t obstacles but tools, because they force better decisions in the real world.Ultimately, his “why” is grounded in life quality: “one’s quality of life is directly correlated to how well their work situation goes.” By building businesses on clear principles and designed environments, leaders gain time, clarity, and better outcomes—not just financially, but for their teams and families as well.Key takeaways Generic advice fits “average” businesses, not your unique reality  Move from mimicry to first-principles decision making  Design your company as an ecosystem, not a machine  Align destination, crew, leader, and systems holistically  Use constraints to make better, realistic decisions  Scale requires shifting from doing work to enabling others