In this episode of Strap On Your Boots, I answer one of the questions I get asked most often How do you decide what to work on next Looking back on a career that spans startups, AI, filmmaking, music, writing, and entrepreneurship, I share the framework that naturally emerged over the years. I discuss why I rotate between creative and technical projects, how curiosity shapes my decisions, why timing matters just as much as the idea itself, and how AI has become an invaluable tool for challenging assumptions before I commit to building something new.

In this episode of Zero to CEO, I speak with Founder and CEO Allan Khazak about why most high-ticket teams don’t have a lead problem — they have a broken conversion process. Allan breaks down the exact system he uses to help insurance producers, advisors, and service-based businesses increase show rates, reduce no-shows, qualify faster, and close based on economic outcomes instead of product pitches. We dive into building an owned, compliant pipeline that works remotely and drives consistent, scalable revenue — without relying on purchased leads or massive recruiting teams. If you sell high-ticket services and want predictable booked appointments that actually convert, this episode is for you.

In this episode of Strap On Your Boots, I reflect on how startup culture shaped my view of entrepreneurship and why I recently found myself questioning one of my own assumptions. After learning about entrepreneurs who buy existing businesses instead of building companies from scratch, I began wondering whether we’ve become too attached to a single version of what entrepreneurship is supposed to look like. I share lessons from my own journey building startups and explore why sustainability, execution, and long-term value creation may deserve just as much attention as innovation and growth.