Next time you walk into a coffee shop, ask for a discount on a cup of coffee. How will you ask for it? Will you feel uncomfortable? Now here’s the catch: you can’t ask for a discount point blank. There’s a chance that a direct ask could get you the discount, but I want you...

Helping Black leaders is crucial. Relative to the general population, there’s a distinct shortage of Black leadership in business. The Black population makes up just over 13% of the US population, yet as of today there are currently only three Black CEOs of Fortune 500 companies—that’s less than 1%. (That means there are more CEOs...

The auctioneer stopped in the middle of bidding and asked me to come on stage. The bidding stopped at $2,000 for a 7-night, luxury vacation for 10 to any of Inspirato’s destinations. It was easily worth over $15,000. And no one’s hands were going up. Inspirato’s “Inspired Giving” program required a $6,000 minimum and we...

Just another chicken dinner gala and they want my money… Fundraisers for nonprofits suck. They all follow the same old subpar formula. Donors are getting fatigued. But nonprofits are in a dilemma. Their tight budgets mean they skimp on details and as a result raise less money. After 20 years of planning fundraisers, I think...