If you run a business, you really should NEVER take a vacation.
I bet most business owners or founders struggle with this too: It is soooo hard to turn your brain off from working. On vacation, I get a million ideas all day, every day.
You’re mentally working on your business when your 14 month old just wants to build sand castles.
My wife, kid and I just spent a week in Costa Rica. I don’t want memories of that trip to be where I came up with a gameplan to increase revenue by 200% next year. That’s stupid. I’ll never get that time back.
I want hundreds of pictures and videos hanging out on the beach and teaching my daughter how to swim.
So my solve has been writing every single idea in my head into my notes app (bc they honestly won’t stop). Every idea gets 2-3 seconds of my attention and that’s it.
That first day back from the trip I want to open up my notes app to 322 things/ideas that I need to attack.
Of the first 22 Giving Pledge signatories who have died, only 1 actually gave their money away. (Thanks Billionaires)
One. Out of 22.
The Giving Pledge was started by Bill Gates and Warren Buffett in 2010. The deal was simple. Sign your name. Promise to give away at least half your wealth in your lifetime or at death.
The pledge has been signed by 240+ billionaires. Sounds like a lot of generosity coming.
Then the Institute for Policy Studies actually checked the math on the ones who died.
21 of them missed their pledge. Wealth still locked up in estates. Trusts that never distributed. Foundations that hold but don't give.
The only one who actually pulled it off: Chuck Feeney.
He started in 1984. Moved his Duty Free Shoppers shares to a foundation 12 years before they sold for $1.6B. Gave away over $8B in his lifetime. Died with ~$5M to his name.
Three-quarters of the Forbes 400 have given away less than 5% of their lifetime fortunes.
The pattern: pledges are easy. Plans are hard. Without a structure that FORCES the giving to happen, it doesn't happen. Wealth wants to compound, not redistribute.
Business owners run the exact same play.
You tell yourself you'll give "after the sale." Then the sale happens, the money hits the brokerage account, and suddenly the plan changes. You'll give "after the next deal." Then "when the kids are settled." Then "when the market recovers."
The cash sits. The cause waits. The years go by.
Exit planning and estate planning takes a lot of work but it's better to do it years before you actually sell to keep or donate the most of your money.
My Toyota Corolla broke down May of 2018. I was almost a couple of years into building a business as a financial advisor.
Which as all financial advisors know about this time period: “you’re grinding.”
(And ‘grinding’ is code for ‘struggling but smiling through it’.)
So naturally, I was not ready to buy the Lamborghini yet.
I lived in Austin and was booking meetings with prospects and clients all over Texas, but mostly in San Antonio.
My sister was about to sell her 2012 Toyota Prius. Every guy’s dream car.
I borrowed it for the next couple of months before buying a new car.
But those couple of months was summer in South Central Texas. That meant days of 101 degrees or more.
On day 2 of driving the Prius, the AC went out.
‘Grinding’ remember?
Those meetings that summer are honestly the biggest reason I’m here today.
It was July 2018 and I had all of my meetings cancel in San Antonio except for 1. I had two choices:
-Just call the prospect and reschedule
-Suck it up and drive
I drove. I had been trying to get this lunch meeting for almost a year. She was the nicest person in the world.
She had no idea that I drove to the Starbucks at the Rim (300 ft from the restaurant) at 5 AM so I wouldn’t be sweating when I arrived. Or that I was working at that Starbucks until my 12 pm lunch appointment. Or that I left my car parked there so she wouldn’t see it when we walked out of the restaurant.
We had a two hour lunch (I had the time).
She became my biggest client. All because ‘I kept showing up’.
I drove the afternoon fun drive on I-35 back to Austin completely shirtless with the windows down.
My car today has AC. And there are days when I think about that 2012 Toyota Prius and don’t miss it at all.
Five charitable giving mistakes I see in nearly every new client portfolio:
1. Giving cash instead of appreciated stock. If you have any taxable investment account with gains, you should almost never give cash to charity. Gifting appreciated shares eliminates the embedded capital gain and still gives you the full deduction.
2. Not bunching. The standard deduction is $30,000 for married couples in 2026. If you give $15K a year, you get zero tax benefit because you're not itemizing. Bunch two or three years of giving into a single year through a DAF and you clear the standard deduction by a wide margin.
3. Ignoring QCDs after age 70½. A Qualified Charitable Distribution lets you give directly from your IRA up to $108K per year (2026). It satisfies your RMD, never hits your AGI, and saves you from the cascade of phaseouts that higher income triggers.
4. Treating giving as separate from the financial plan. Charitable giving is a tax tool, a portfolio rebalancing tool, and an estate planning tool. When it's siloed as a "values" decision, you lose 30 to 50 percent of its financial value.
5. Waiting until December. The best giving decisions happen in January, not December. December giving is reactive. January giving is strategic.
Please use the right planning for all donations.