S3E2 In Pursuit of Freedom
Resources mentioned:
About this episode
Chris grew up following the same playbook most of us are handed. Get good grades. Get a stable job. Climb the ladder. By his late 20s, something didn't sit right. He started questioning the rules, not to rebel but because they didn't make sense to him. He'd work from home when it wasn't allowed. He'd show up to job interviews without a suit. He calls it thinking for yourself.
In 2019, after being pushed out of a startup, he started Refine Labs from his couch with $3,000 in the bank and $62,000 in student loan debt. He sold his car to extend his runway, got a roommate, and started picking up consulting clients. Within months he was earning more working 20 hours a week than he ever had in corporate, with time to explore photography, yoga, and his health.
Then the business took off. Revenue went from $600K to over $20 million in about three years. But as the numbers grew, so did the cost. Chris describes a repeating cycle he calls the success game: learn, grind, achieve, optimize, burn out, repeat. He was stuck in it without realizing it. He couldn't sleep. He couldn't take a vacation without guilt. He felt obligated to spend time with people he didn't want to be around. He rated himself a 2 out of 10 on both mental and time freedom while the business was thriving.
He also opens up about carrying self-doubt for 33 years while being one of the most confident public voices in B2B marketing. His breakthrough was realizing that anxiety and self-doubt aren't personality traits. They're symptoms of unexamined beliefs. Once he started questioning the beliefs instead of managing the symptoms, everything shifted.
On money, Chris says the freest he ever felt was making $20K a month with three happy clients and no employees. As revenue scaled, he kept chasing more without understanding why. He was on the hamster wheel until 2023, believing $100 million would finally be enough. “It’s never enough.” He says, “When you outsource your self-worth to external outcomes.”
His exit decisions reflect the shift. He sold his Refine Labs equity at a fraction what it was worth because his freedom mattered more than maximizing the number. He sold his shares in his other software company, Passetto, for almost nothing because the people building it every day deserved to own it. These weren't spreadsheet decisions. They were integrity decisions.
Chris now runs ENCODED, an AI-powered frequency training system that helps founders and high performers upgrade their identity, beliefs, and intentions through a structured daily journaling practice and companion app. His mission is to help people stop chasing success externally and start training freedom internally.
We close on his 10 Dimensions of Freedom framework: time, social, creative, financial, health, location, purpose & mission, relationship, mental, and spiritual. Chris says he never makes a decision that raises one dimension while collapsing another. When I said "isn't life about trade-offs?" he responded: that's programming.
Key Timestamps
(01:08) What success looked like in Chris's corporate years
(04:32) Starting Refine Labs with $3,000 and $62K in student debt
(06:30) The freest he ever felt
(07:42) When passion turned into proving he was smarter than everyone
(09:32) The Success Game: the six-step hamster wheel
(14:00) Why believing success requires suffering creates it
(17:14) A 2 out of 10 on mental and time freedom
(18:35) Realizing $100M in B2B marketing was purposeless
(20:42) "This is just who I am"
(22:11) The biggest breakthrough of his life
(27:30) How self-doubt and public confidence coexist
(28:30) Frequency: identity, beliefs, and intentions
(31:55) Money as the goal vs. the byproduct
(34:30) Why $100 million would never be enough
(39:00) Selling Refine Labs equity at 20% of its worth
(40:38) Selling his Passetto shares for $18
(43:12) The mission behind ENCODED
(45:30) Frequency training as a daily practice
(47:50) The 10 Dimensions of Freedom
(49:42) "Isn't life about trade-offs?"
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About ProfitLed
Most startup advice is built around venture capital, hypergrowth, and unicorn exits. ProfitLed is for the rest of us. Hosted by Melissa Kwan, 3x bootstrapped founder and CEO of eWebinar, ProfitLed explores what it's really like to build a company on your own terms, without an abundance of resources and friends in high places.
Season Three goes beyond strategy as we explore the intersection of Passion, Profit, and Purpose and what happens when founders evolve and come into financial success.If you're building something real, this one's for you.
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