The Work Beneath the Work: From Fear to Joy
He moved countries four times without anxiety. Then he tried to move fifteen miles — with a Ferrari in the driveway and fifty trophies on the shelf — and couldn't breathe. That moment cracked something open. "The more stuff I own," he realized, "the more it owns me." Within four weeks, everything was sold. He moved in three boxes and his clothes. That was enough.
Rudy Karsan is not the kind of person you expect to find in this space. He took a company from $5,000 in credit card debt to a public exit — twenty countries, two thousand employees, a unicorn. He was bankrupt three times along the way. He wrote a New York Times bestseller. He drove the Ferrari. He refused the alumni award — told the university to melt it and make next year's.
Now he convenes forty to fifty intimate conversations a week on topics like "building connection through intimacy and vulnerability," "how to be ruthlessly compassionate," and "where is the joy in lingering?" He calls them FunCons — not because they're light, but because he has learned that depth and delight aren't opposites. That's the discovery at the heart of this conversation.
Rudy grew up in the Ismaili tradition in Mombasa, Kenya — a faith, he says, that emphasizes the batan (the inner, the spiritual) over the zaher (rites and rituals on the outside). He was meditating and praying from the age of five.
"It's not the other. It's not a practice. It's a state of being."
Three ethics formed his core: the intellectual ethic, the service ethic, and the spiritual ethic. These weren't frameworks he adopted later — they were woven into how he talked, how he moved, how he made decisions under pressure. When he eventually lost everything after selling his company, it was this foundation that kept him from a free fall with no bottom.
Fear brought Rudy to entrepreneurship. He landed in England at fifteen — not yet sixteen — and knocked on doors within forty-eight hours, needing work. Fear of poverty drove him to become an actuary (the best-paid profession he could find in the 1970s). Fear of being controlled drove him out of employment and into his own companies. Fear and ambition braided together into something that looked, from the outside, like extraordinary drive.
But he also learned — through three bankruptcies — the cost of following what he calls "the glitter."
"Every time I followed the glitter, you get the short-term high and the long-term pain."
The antidote wasn't willpower. It was learning to embrace the parts of himself that chased the glitter in the first place — what therapist Richard Schwartz calls No Bad Parts — understanding that those anxious, grasping parts were created in moments of vulnerability, trying to protect him. Metabolizing them, rather than fighting them, became the real work.
After a twenty-five-year journey — failures, bankruptcies, scaling, going public — Rudy sold Kenexa to IBM. He took a picture of the check. He called his banker.
He felt nothing.
"I thought that was my private celebratory moment, and it never happened."
Then the sadness crept in. He cried himself to sleep for three weeks. Not because the deal was wrong — but because three fears, long submerged, suddenly had no more distractions to hide behind: the fear of death (the brand died, everything died), the fear of suffering (I have nothing), and the fear of not belonging (I no longer belong). Each one had to be acknowledged, felt in the body, and metabolized.
What he describes is not a clean narrative arc. It's crawling, then holding onto a chair, then falling, then walking again. He says the speed of emergence isn't what matters. What matters is acknowledging your helplessness and your loss.
"The quicker you can get to embracing it, the quicker the truth arrives."
After the exit, Rudy stripped things down. Cars sold. Trophies thrown away. He moved into a condo in the city with three boxes and discovered something that surprised him: lightness. Not loss.
He keeps one principle sharp: he will always accept love, but never adulation.
"The minute you say you're great because you got that — it's a really slippery slope."
This is the discipline behind refusing the alumni award. Behind downsizing not as renunciation but as clarity. The ego, he has learned, is extraordinarily good at disguising adulation as love. The practice is learning to feel the difference.
He applies the same scrutiny to what moves inside him. Anger, he says, he has figured out — convinced himself it serves no purpose, just a waste of energy — and so it moves through his system and clears. But greed is harder. Greed is the live edge.
He notices he is greedy for knowledge, greedy for exploration. He can relabel that as curiosity. And curiosity, he reasons, comes from love rather than fear. But then the question arrives and he doesn't flinch from it:
"Am I fooling myself into believing that being greedy for knowledge is the same as curiosity?"
He doesn't know. What he does know is that the physical being is driven by fear, and the eternal being by love — and he is still, undeniably, in a physical being. Is there a knife-edge between the two, and can you walk it without slicing yourself? Or is it less a knife-edge than a bridge? He is still finding out. That willingness to sit in the not-knowing, to keep asking the question without rushing toward an answer — that, too, is inner play.
Rudy now backs entrepreneurs through Karlani Capital — but with a different set of masters than the ones that governed his Kenexa years. His companies are privately held and structured around three returns: return on capital, return on compassion, and return on community.
"The only master isn't capital."
He also listens for something unmeasurable when meeting founders: vibrational information. The who, he says, matters more than the what — especially at early stage. He asks unexpected questions, including one no one has ever asked him before in any interview: What is your perception of death? Not morbidly. As a way of following an energy trail toward the person's deepest ground.
His own answer: death is a transition, a release of an ill-fitting suit. When a recent bout of severe vertigo left him unable to stand, he found himself accepting it and falling asleep with a smile. "I'm ready," he thought. That, too, surprised him.
Toward the end of the conversation, Rudy described his practice: prayer, meditation, contemplation, self-exploration. Then host Cynthia Li offered him a word he hadn't used: inner play.
He stopped.
"Inner play is a lot better than inner work. Because you're dancing. When you're doing it, you're dancing in joy."
This is what FunCon tries to hold: the serious depths of human experience — grief, fear, greed, love, death — approached not with grimness but with the lightness of genuine inquiry. Laughter isn't a distraction from the inner life. It is, for Rudy, evidence that the pipe is open — that you're allowing yourself to actually feel what's present.
The evolution he describes, again and again, goes: blame others → blame self → blame the environment → blame God → start laughing. The laugh is not escape. It's arrival.
Asked how the Awakin community could support his work, Rudy offered three invitations — simple, earnest, and oddly demanding:
Laugh twice as much as you currently do. If you laugh six times a day, make it twelve.
Play for at least an hour a day. The gods want us to play. We were created for it.
Find your path to stillness. Prayer, meditation, contemplation — whatever your journey is. Discover it.
"If you do those three things, the world will be a better place. Laugh. Play. Stillness."
To spend time with this full conversation — with its warmth, its digressions, its moments of genuine surprise — is to receive something that resists summary. What Birju Pandya called "the feeling of I don't know." What it feels like to laugh. The wish to be in those spaces, in relationship.
You can find the full Awakin Call with Rudy Karsan at [awakin.org].
Awakin Calls is an initiative of ServiceSpace, a distributed global community run entirely by volunteers.
Listen to the complete conversation with Rudy Karsan.