Khe was shy. “Nerdy.” Very insecure.
The constantly running tape in his head during his teenage and college years?
I'm not cool.
He felt exposed and yet invisible.
“I don't like who I am right now,” he thought. But instead of learning to like himself, he turned his attention outward. He focused on something that seemed easier – being seen. Recognized.
What did the world recognize as success?
Maybe that would cure his insecurities? “I didn't really know any other way to become cool other than to try to become very successful.”
He felt exposed and yet invisible.
Khe pursued a career on Wall Street. He made a lot of money. And he felt less insecure.
For a little while.
You'd get this bonus…go out to dinner and get a nice bottle of wine, buy a new pair of shoes, and maybe upgrade your hotel room for your next vacation.
And then four weeks go by and you feel whatever that existential yearning was, or that hole in your soul. It'd be like, ‘Knock, knock. You thought that bonus is going to make me go away. I'm back.’
But every time Khe would think about changing his career, he’d get another bonus, and the cycle would repeat.
For 14 years.
“I'm in the wrong business.”
Everything changed for Khe when his first child was born.
The last-minute Saturday morning meetings didn’t seem so important when they meant missing his kid’s birthday.
There's got to be a different way. That 10:00 AM Saturday meeting is not that important. And if it is, then I'm in the wrong business.
Khe wanted to be a creator.
As he got older, it was the creatives whom he admired most. He wanted to be like them. He wanted to make something out of nothing – not just money out of money.
On his off time and sparse vacations, he’d spend hours reading everything he could find online about being a creator, like a Keith Rabois interview on how to start a startup and Reid Hoffman’s thoughts on the 10,000 hours theory.
He was fascinated by what he was learning about being a creator – it was such a different mindset than the finance one he was living in – and he couldn’t keep it to himself.
On a whim, during a vacation in 2015, he wrote an email to 36 friends, linking all his favorite articles along with short descriptions of what he loved about each one. “And that was it.”
It was only supposed to be one email.
But his friends wanted more.
And he loved the spark of creating something and sharing it with friends.
And he was going to keep up his reading habit anyway, so why not?
He sent another email. For fun.
He didn’t know then he was starting something that would change his life. Something that would still be going five years later. Something that would spark him to finally act on the idea he’d been stewing on for years.
“Achievement is like a piece of tape.”
Khe had been talking about quitting his job…for two years.
But, that was normal: “On Wall Street everyone talks about [quitting] because people are generally not happy and the only reason they're there is for the money.”
He didn’t think he’d actually do it.
Who would he be without the money, status, power?
The fear was too great. So he kept putting it off.
But as he kept avoiding the instinct to change his life, something else changed.
I started to mentally check out.
I'm the type of person who could do 90% of effort for a couple of weeks, but then I have so much guilt and almost like internal shame that I'm like, ‘I just can't take it; I have to quit.’
Because it's the worst feeling to show up as 90% of yourself.
He had a life coach then – something he saw his successful friends doing – and he talked to her about the shame, the fears he had about quitting, about seeing his bank account dwindle – every month.
Who would he be without the money, status, power?
All he could see were the worst case scenarios: Broke. Homeless in New York City. No health insurance for his family.
His coach asked him one simple question:
If this doesn't work out, how long do you think it will take you to get a job? Three months?
He realized all his fears were dumb.
Or rather, a mirage.
He felt like he’d be putting his whole family in danger, but all that was really in danger was his ego.
His financial stability wouldn’t really be in danger. What he was afraid of was the unknown, and what would happen to his ego, his identity, if he did leave and have to come crawling back – the insecure teenager exposed.
But the ship was sinking.
[My insecurities were] like a leaky ship with all these holes and I was just patching it up with achievement, and then eventually the dam broke because achievement is like a piece of tape. It's not actually fixing the hole.
He had spent so much time running away from who he was.
Khe decided to make just one more investment at age 35.
This time, in himself.
He didn’t spend a lot of his money (it turns out it wasn’t all that satisfying), so he had a lot of savings.
He talked to his wife and they decided to set aside two years of full-time income from their savings to live off of, giving Khe two years to explore what else he wanted to do with his life.
I made an angel investment in myself. I expected to lose it, but there was a small chance for a spectacular return.
He quit his job.
No one understood.
People were like, ‘You walked away from that job? And you write a 36-person email newsletter? Like what the F— is wrong with you?’
‘You're 35, you have a kid, your wife is an artist, you are going on COBRA because you literally can't get insurance through your wife, and you're walking away from the job that people dream to have?’
At the time Khe was also in the highest position at his company – a managing director. He was also the youngest to have the title. He’d achieved everything he ever wanted. He would be financially set for the rest of his life – all he had to do was stay.
So no one understood when he walked away.
But he did: “It was heaven.”
I only took two weeks off in a row twice in 14 years. One was my honeymoon and one was when I was like 22. I didn't know what it was like to walk around during the daytime on a weekday.
I had all of these Nike Air Maxes but I only had two days out of the week to wear them because I was wearing crushed shoes for the other five.
He could hardly believe the possibilities: “I could wear a different pair of sneakers four days in a row?”
He had spent so many years trying to achieve what the world saw as success that he hadn’t taken the time to walk a mile in his own shoes.
He had spent so much time running away from who he was. But instead of trying to fit that shy insecure teenager into someone else’s box, he was ready to create a new one.
It was incredible.
It was also terrifying. So I don't know if you want to talk about the terrifying part.
I do, I tell him. I definitely do.
But first, Bali.
“That's not my identity anymore.”
After spending 70 hours in an office each week, the first thing Khe did after quitting his job was book a one-way ticket to Bali – along with his wife and one-year-old: “So cliche,” he laughs, “We did the family version of ‘Eat, Pray Love'.”
They traveled for three months, and the trip was so meaningful that when they got back Khe tattooed the flight numbers on his arm.
And before the tattoo fully healed, the questions started coming, fast.
What was his plan?
He didn’t really know. Because he didn’t really know who he was anymore.
I had to start to rebuild my identity from the ground up because I no longer could say ‘Oh you know that fancy job on Wall Street? Yeah, I got that.’
That's not my identity anymore.
And it’s a very convenient identity because people tend to know it.
But it wasn't a true identity.
Because it wasn't really me.
He wanted to find out who else he could be, but after 14 years doing the same thing, he explains, his initial view was narrow.
He still struggled to think of himself outside of the world of finance – he knew he wanted to be a creator of some kind, but he didn’t think he was worthy to step too far outside the box he knew.
Maybe he’d do something in financial tech or become a seed investor?
But the initial burst of confidence that led him to quit his job faded fast, especially once he saw his bank account go down – not up – every month, for the first time in 14 years.
That is an important fact that I think gets swept under the rug often when creators talk. I had financial runway. But no matter how much money you have, when your bank account goes down consistently for months, years…no one's emotionally ready for that.
When he went out to eat with his wife, he only ordered water to drink.
His wife gave him a funny look – that wasn’t like him. But he was ordering water – saving money – because he already felt like a failure.
He was convinced he was going to fail as a creator before he even started.
All the while he was still sending out what had become his weekly newsletter – which he called RadReads.
When I was in finance in New York City, I fantasized about surf life and have always aspired to live a ‘chill’ relaxed California life. So I promised myself that my future company would have ‘rad' in its name, especially to force my old, old-school colleagues to use the word ‘rad.’
To me, the definition of rad is being cool without having to work for it
By now the newsletter had transitioned from blind copying 36 friends to over 100 people on an email service provider. (When he left finance everyone was so curious about where he was going to go next; he told them they could stay in touch by joining his newsletter, which they did).
But at first, being able to see the data behind his emails was daunting; if his open rate went down by even 5%, he would get down.
And the texts he kept getting, all asking the same question, brought him down even further:
What are you doing???
Some people genuinely wanted to know what he was up to, but to him, all those texts were actually saying:
You’re crazy. You're dumb. You've made a big irreversible mistake. How come you don't have an idea yet?
He started a venture capital business just to get the texts to stop, just to have an answer.
It never occurred to him that the weekly newsletter he was writing in the background would be the thing that took him into his next chapter, showing him who he was, and who he could be.
He let the shy insecure teenager speak up.
Khe loved writing. RadReads was his anchor; and along with the curated articles he was reading, he also shared his journey, honestly, as it was happening.
Email by email, he showed up a little bit more every week. He let the shy insecure teenager speak up.
And people identified with him. With his journey.
Khe didn’t have answers. All he had was curiosity. An open heart.
His emails, and his sincerity, resonated.
Email by email, he showed up a little bit more every week.
And even though he only had a few hundred people on his list – all people he knew personally – he started to get unexpected opportunities via email replies.
Like when someone on his list replied to a newsletter asking Khe if he would speak at a TEDx event.
Then, a manager on Khe’s list asked him to come coach his team – who, according to him, were “mostly very driven-type men that are not very in touch with their emotions.” He wanted Khe to help them work through some of the thoughtful questions about life, work, freedom, and happiness that Khe was pondering in his newsletter.
Seriously? Someone wants me to coach someone, like another grownup, about making grownup people decisions?
The manager wanted to pay him for his time, too.
Khe really couldn’t believe it, but, curious, he said “Okay” to the coaching opportunity.
He was really good at it.
All the internal work he did to take a step back from a narrow 14-year worldview was now something he could teach other people how to do – widen their aperture, ask the hard questions, figure out the real fears, and pivot when needed.
His bank account started to go up again, just a little.
And then, another person on his newsletter emailed him: Lauren Brown.
She made a career out of holding mirrors.
Lauren was the senior editor at Quartz, a media company, and when they started an entrepreneur in residence program she thought of Khe’s newsletter and asked him to be their first entrepreneur in residence.
He couldn’t believe what people were seeing in him; in some ways he felt as lost as ever.
But Lauren, he says, really saw him: “She had this magical talent of seeing these things in people that they didn't even see in themselves, and aligning them with bigger industry trends.”
He thought his newsletter was just fun – but she was the one who showed him that what he was doing was valuable: “You’re a good writer; you may not even know it,” she told him.
Lauren helped Khe find an identity again – helped him believe he was already a creator, that maybe he always had been.
Lauren died last summer, at the age of 38, from breast cancer, and Khe says everyone who knew her had a story like that. She made a career out of holding mirrors, helping people see the possibilities they couldn’t see by themselves.
Inspired by Lauren and all he learned at Quartz, Khe kept writing his newsletter with new fervor.
And the people on his list started forwarding his emails to their friends.
Two of his subscribers happened to be friends with reporters at Bloomberg and CNN.
Within a few months, both reporters reached out to do articles on Khe and his journey.
By then his email list was 1,500 people, purely from word of mouth. But after those two articles went live, his email list was over 10,000 subscribers.
He got 9,000 new subscribers in 9 days.
He wasn’t making much money yet, but that was intentional.
They were still living off of the two years of savings he’d set aside; he knew it was a luxury, a privilege, to have that runway and he wanted to make the most of it and not jump into something too quickly, out of fear. He’d done that for 14 years.
This time, he wanted to find work that was fun.
I could have broken even way earlier if I had elected to do more consulting things that didn't seem super compelling to me. Or choosing to work with people who weren't particularly inspiring. So I said ‘No’ a lot to remain true.
I really am guided by things that I find fun, which is probably a dangerous business model, but it also means that at any point in time I'm always 120% energized to do what I'm doing.
He never wanted to go back to only giving 90%.
So Khe allowed himself to move only in the directions that sparked him. He wrote his newsletter the same way.
So when Notion came out, a workspace collaboration app, Khe shared it in his newsletter because he loved using it.
People emailed him questions and in return he’d send them short tutorial videos back using Loom just for fun.
This time, he wanted to find work that was fun.
People loved the tutorials and they kept coming to him with more questions – and Khe loved teaching about something he loved.
Maybe he should make an online course on how to use Notion?
It sounded fun, like something he’d want to invest himself in, 120%.
He went all in, using Zoom and Gumroad to create his first online course. And then he emailed his list about it.
The list he’d been writing to weekly for five years.
Without ever asking anything in return.
“What are you talking about? What am I going to teach a course on?”
For five years Khe didn’t sell anything to his email list. (Even his coaching, he explains, stayed word-of-mouth only, and still is to this day; “it's helped by the newsletter because I stay top of mind.”)
Finally, he had something to sell.
His first launch made $10,000.
People responded in droves – they were thrilled to finally have a way to support him, to learn even more from him.
His second launch made $15,000.
Then he built his first automated email sales funnel, even though he didn’t know how. To learn, he subscribed to as many sales funnels as he could and studied how they were writing and what resonated with him and what didn’t. He used those as models to make his own.
His next launch, using his first automated sales funnel, made $25,000.
If you had asked me in March of 2019, ‘Are online courses going to be the driving and growing part of your revenue?’ I would be like, ‘What are you talking about? What am I going to teach a course on?’
But I was set up. I had the audience. I didn’t understand email marketing, but I was good at email.
Khe was good at email because he never lost the spark that started it all – no matter how much his list grew, he never stopped writing like it was just 36 friends in the BCC section.
“You've inspired me to live on my own terms.”
To date, Khe has 19,000 people on his list and a very high open rate – 55%.
When he shares his open rate, some business people balk at the high percentage: “You should actually have a lower open rate and be more aggressive.”
Khe doesn’t necessarily believe they’re wrong, but, as he shares, “that's not my personality.” He knows who he is now, and he loves doing email his way.
Email marketing helped him turn his newsletter into a business – he’s in love with automated email funnels now – but the money was never what this was about for Khe. He had money. He was grateful for it; it’s what allowed him to quit his job and explore his next phase.
But he also knew that money was tape. Temporary. If money was the point he would have stayed on Wall Street.
He tells me about a folder he has – of all the email replies he’s gotten over the years – the ones that have really affected him. People tell him their stories, and how his story gave them courage to throw out society’s expectations and start valuing their own metrics.
A new definition of success.
Money, power, and status don’t mean much to Khe anymore.
When he stripped it all away, and started listening to – and writing as – who he really was, he found his own definition of success.
Because there isn’t just one; or, if there is, it’s having the courage to make that one up on your own.
Khe has his own definition of success now, which he lists out for me:
- The ability to be present and give my best energy to the people I love.
- To only spend time with people who inspire me and bring me energy.
- To use my creative gifts every single day.
- To never feel rushed.
- The ability to control my own schedule.
- The ability to surf every day.
Khe’s advice to people who ask him about wanting to break away from conventional ideas of success?
If you're afraid of something or if you're insecure about something, dig deeper. Be curious, be nonjudgmental about it.
Look at my life, 35 years of insecurity and anxiety and feeling bad about myself, trying to soothe myself with status and things like that. It wasn't until I started actually looking at those feelings and leaning into them that it really opened me up.
To Khe, that kind of awareness is everything.
People always talk about extending the financial runway by cutting costs or saving more money.That's important.
But if you can extend the emotional runway, you're unstoppable.
After our phone interview, Khe gives me a virtual tour of his home office, including the garage where he works.
There’s one thing he’s really excited to show me.
He clicks a button and the garage door slowly opens, sunshine pouring through.
That’s when I realize he doesn’t live in New York City anymore.
I remember number six on his list.
He walks out of his garage, onto the street, pointing the camera just past his sincere, boy-ish grin, and that’s when I see it.
The Pacific Ocean.