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Why really rich people worry (about money)

Why really rich people worry (about money)

November 2, 2023
Imagine being having $20 million and being scared of losing it all. Now imagine having $100 million and “sleeping with one eye open.” Yet, the scarcity mindset is a terrifying boogieman. Who strikes at all levels of wealth. It’s a fear that lurks around the corner. A fear that the “rational brain” can’t overcome by […]
Life after “Golden Handcuffs”

Life after “Golden Handcuffs”

May 4, 2023
Leaving Wall Street cost me $900,000. Yup, the “Golden Handcuffs” are real. Bonuses are deferred. So by definition you leave money on the table. At 35, I said f** it. I want to own my time, surf every day & watch my kids grow up. 8 years later, I’m still standing. I’ve learned a lot […]
Will you have “retirement regret?”

Will you have “retirement regret?”

April 4, 2023
Guys, I screwed up. I left Wall Street at 35 without a plan. I was constantly told: “You’re throwing away your Peak Earning years.” The haters were right. I’m now 43 and my net worth is exactly the same as it was at 35. I screwed up my retirement. And that’s great news. It’s time […]
Status games: Absurd or necessary?

Status games: Absurd or necessary?

March 16, 2023
Are you a green bubble or a blue bubble? You know what I’m talking about. Even if you use WhatsApp. Heck, you’ve probably denied someone entry into your group chat because of the green bubble. (Our surf group has displayed this savage behavior – so I’m not above it.) The green bubble is a red flag […]
How to overcome the “scarcity mindset”

How to overcome the “scarcity mindset”

December 6, 2022
We’re surrounded by scarcity.  The day starts with “I didn’t sleep enough.” Then the rush to get the kids fed and out the door is accompanied by the nagging feeling that as parents we’re “not present enough.” Next, a commute skimming articles on our phones and listening to podcasts at double speed. There’s too much to […]
When a dollar is not worth a dollar

When a dollar is not worth a dollar

November 5, 2021
I love ice cream. Jeni’s. Ample Hills. Salt and Straw. Van Leeuwen. If it’s cold, creamy and chocolate-y – I love it. But as a 42 year old, ice cream and the Notorious B.I.G. have something in common: Mo ice cream, mo problems. (That is a terrible dad joke.) You see, the Chocolate Gooey Brownie […]
It’s ok to take a walk without headphones

It’s ok to take a walk without headphones

February 20, 2021
The Big Sur MacOS update delivers a delightful Easter Egg. Your AirPods now magically follow you across devices. Gone are the awkward transitions (“hold on, let me connect my AirPods”) while fiddling with your Bluetooth settings and pressing that random button on the white case. Now you can gracefully glide from podcast, to Zoom call, […]
The hidden benefits of renting (over buying)

The hidden benefits of renting (over buying)

September 15, 2020
This post was adapted from a @radreadsco Instagram story. If the old adage “paying rent is like burning money” is true, then our family has (and will) continue to burn it for many years to come. Two years before I left Wall Street, I made the conscious decision to de-risk our financial picture by selling […]
The Gordian knot of identity and achievement

The Gordian knot of identity and achievement

July 11, 2020
“Stress is a perverted relationship to time.” These words from the late Irish poet, John O’Donohue are truthfully incisive. And whether it’s using Text Expanders or doing Tabata Burpee workouts – I’ve always been in the hot pursuit of more time. The chase is straight forward. More free time equals more time to do stuff. […]
The dubious promise of financial independence

The dubious promise of financial independence

April 20, 2019
Last week, we hung out with our man Sherman paralyzed by his $1.2 million salary and bereft of agency over his own life. He’d played his cards right – attending the right schools, developing unique skills and landing in a lucrative industry. Yet the path to financial independence was sealed off to him. Well that’s […]
How to build durable and long-lasting Atomic Habits

How to build durable and long-lasting Atomic Habits

February 4, 2019
A friend once told me they used set recurring daily reminder to read more. “Come on,” I responded, “that would be like putting having sex on your to-do list.” Paying your rent, filling out school applications and scheduling annual physicals are tasks. Making love, exercising, and sleeping more (maybe the three form a compelling bundle?) are […]
Resentment: The silent relationship killer

Resentment: The silent relationship killer

January 19, 2019
“Do you think your wife would ever leave you?” It was a jarring question, one that shook up routine coaching session. “Absolutely,” I said without any hesitation. I surprised myself with my answer’s assertiveness. It was a bit like jumping off a cliff at an amusement park. You trick your legs into jumping, a split […]
The career arc of specialists and generalists

The career arc of specialists and generalists

October 20, 2018
This post first appeared on Instagram over @radreadsco. Ascending the corporate ladder can involve an alphabet soup of options. There’s T vs. I-shaped professionals, a concept pioneered by design guru and IDEO CEO Tim Brown. For the wonkier free-agent types, there’s the semicolon-shaped person coined by blogger Venkatesh Rao. These frameworks all seek to reconcile the perceived trade-off between […]