Zig When They Zag... Zag When They Zig

Ryan Levesque is the Founder of The ASK Method® Company, which helps companies understand their customers' needs through strategic questioning techniques. He is a seven-time Inc. 5000 CEO and founder and a two-time national best-selling author, with his book Ask named the #1 Marketing Book of the Year by Inc. Magazine. Ryan also Co-founded Bucket.io®, a leading marketing automation platform used by over 80 million people globally. His work has been featured in major outlets like the Wall Street Journal, Harvard Business Review, Forbes, Entrepreneur, and NBC News. In this episode… Have you ever followed the so-called “perfect” business playbook — only to watch your biggest deal fall apart? What happens when your vision of success doesn’t go according to plan, and the result forces you to question everything you thought you wanted? What if the solution isn’t to double down, but to step away and ask entirely different questions? Ryan Levesque, author and expert in direct response marketing, shares the deeply personal story of a failed $70 million deal and how it led him to radically rethink his life and business. Ryan offers powerful, reflective questions designed to uncover blind spots, shift perspective, and inspire change. He explains how doing the opposite of your market, identifying underused marketing channels, and re-engaging with the physical world can unlock new opportunities for personal fulfillment and business growth. In this episode of the Timeless Marketing Podcast, Brian Kurtz hosts Ryan Levesque, Founder of The ASK Method® Company, about redefining success and embracing a contrarian path in life and business. Ryan explores the value of self-inquiry, the marketing opportunity in audio and analog, and the unexpected lessons learned from starting a farm. He also discusses audience intimacy, market saturation, and the future of digital platforms.