Show Notes
What happens when you reach the top of the mountain you spent your whole life climbing, and you still feel empty? That is the question at the heart of this conversation with Robby Jones.
Robby is VP of Sales at SAP, running a $200 million ARR enterprise business with a $60 million ACV quota at just 32 years old. He is a member of our seven-figure club, and last year he closed one of the largest deals in SAP's history — a nine-figure deal. By every external measure, he has made it. But Robby's story did not start anywhere near the top. He grew up in Vancouver with parents who divorced when he was a baby, a mom who raised him in Canada, and a household shaped by addiction and scarcity for most of his childhood and adolescence. No money for basketball shoes. No vacations. A two-bedroom, one-bathroom ground-level suite with no stairs. He remembers as a kid thinking: when I get older, I am going to have a place with stairs. Grand ones. He followed his stepfather into the trades. Got a plumbing apprenticeship. Got laid off on his birthday. Then, inspired by a conversation with his grandfather over coffee, he applied to 50 sales jobs on Craigslist, got into door-to-door sales knocking on residential doors for a Telus contractor, and did it for two years. On the van rides to the territory every morning, they played Jim Rohn, Tony Robbins, Zig Ziglar, and Brian Tracy. He had never heard any of it before. It rewired him. That rocket fuel drove him from door-to-door to tech sales to SAP, where over nine years he built a career that most sellers only dream about.
And then he closed the biggest deal of his life, hung up the phone, and thought: is that it? This episode is about what happens when achievement stops being enough, and what the real work actually looks like.
Here is what we covered: Growing up with scarcity, addiction in the family, and how those have-nots became a relentless drive to succeed The birthday he got laid off from his plumbing apprenticeship and why it was the best day of his life Two years of door-to-door sales and the positive brainwashing that changed his mindset forever The inward to outward shift: how moving from "what can I get" to "how can I help" unlocked his biggest results How Robby became so embedded with one enterprise customer that he had a badge, walked the halls, and built relationships that still greet him with hugs at conferences today Closing a nine-figure deal and feeling nothing after: the commission hangover nobody talks about The dark side of achievement-driven identity: addiction, inability to be present, and projecting onto the people closest to you How taking his mom to Italy two years ago was the most sober and present he had ever seen her Breaking a generational cycle of addiction before his first child arrives in October His north star coming out of coaching and therapy: not fulfillment, not success. Freedom.
Robby's story is proof that you can come from nothing and reach the very top. It is also a reminder that the inner work does not stop when the commission check clears. The goal was never just the deal.
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