We did it! 100 Episodes and we’re just getting started. In this very special episode, Rob reflects on the origins of the show, how it evolved, and what he’s learned along the way. As a show that spent its early days interviewing Dyrdek Machine portfolio founders, it soon began leaning into advice for aspiring entrepreneurs. But as Rob continued honing his life philosophy, working on a book, designing software, it became clear where the show needed to go moving forward. As it turned into the show you’ve enjoyed and learned from over the past year, everything seems to be aligning. Rob will also take us through five of the most resonant moments on the journey so far, and provide even greater insight for each.

If you create simplicity and measurability in several areas of your life, you will then be able to strategize how to achieve those goals, resulting in happiness upon completing those goals. Then you’re able to set new, simple goals, measure success, and create even more happiness. It’s a process Rob calls Quantified Joy. In this episode, Rob takes us through his process of creating measurable outcomes and then allowing the numbers to inform the strategy and track the progress. The more you make incremental progress toward those goals, which you can only track if they are quantifiable, the more motivated you become, and the faster you achieve them. The output: Joy. The more you implement this practice in various parts of your life, the more joy you will experience through achievement, and thus the happier your life will become.

Have you ever wondered how much you really make per hour of work? It’s a bit more complicated than dividing your salary by 40 hours per week. First of all, there’s the obligatory taxes we all pay, so subtract those–that money goes straight into Uncle Sam’s sizable pockets. Next, you have to account not just for said supposed 40 hour work week, but also the actual amount of time and energy you spend thinking about work, preparing, networking, training, and everything else that contributes to your ability to generate income. Why would Rob spend an entire episode talking about this? Because at the center of his philosophy is Financial Harmony. This means designing your financial life in a way that allows you to maximize your time and energy to spend on things you most enjoy while still generating wealth. In this episode, Rob shares his secrets to creating financial harmony, and provides his playbook to work hard and save harder.