The world’s most famous skateboarder—now a father of three—explains how to raise a brood of risk takers

Tempted by the Fruit of Another Summer

All my life I've had cravings for that which is ripe and ready to fall—even if I had to take it by force

Before puberty, before the swells and curves of the human body became such an obsession, I began to notice fruit. Coconuts swaying with their palms in tropical breezes from the Arabian Sea, egg-shaped sapodillas nestling slyly in the folds of trees, the flash of the occasional golden tumescent guava hanging just out of reach. Most striking of all were the mangoes dangling in bounteous clusters from the branches of a tree that spread out over our school compound. I stood underneath, enthralled by the mangoes' green smooth-skinned voluptuousness, and willed for one to fall. Each time I found a mango in the bushes beneath, no matter how small or immature, I took a bite. There was something magical about eating food I had found myself, something gratifying about partaking of the tart, even bitter flesh.

The Importance of Being Earnest

This denim doctor is mastering the streets

Immune Boosters

Supercharge your diet with these doctor-approved upgrades

My interest in what is now known as integrative medicine began many years ago when I was a teenager and witnessed my grandmother battle a breast-cancer recurrence. In those days, it was typical for patients receiving chemotherapy to be confined to a hospital bed. Nothing was done to stop her decline—not nutritionally, not physically, not really medically—and she eventually wasted away and died in her bed.

A few years later, in medical school, I began suffering from ulcers and migraines. None of the physicians I visited provided any significant relief. Month after month, I tried to find a cure. Hypnotherapy, acupuncture, Rolfing massage…nothing worked. Out of desperation, I stopped eating the roast beef, burgers, and fried chicken I'd been raised on in favor of whole grains, legumes, and fruit. The idea that nutrition could help fight pain and illness was, in the medical community of the 1970s, unheard of. Yet within weeks, my ulcers and migraines disappeared.

Playing Ball

An auctioneer showcases his $500,000 collection of Chicago Cubs memorabilia and shares the secrets of his trade

As president of Mastro Auctions, the country's largest sports—memorabilia auction house, lots of great stuff passes my desk, but I give pause only to Chicago Cubs items from 1907 and 1908—the last seasons the franchise won the World Series. The Cubs were terrible when I was growing up in Chicago, but when I saw an old tobacco card from the 1908 team at my first sports-memorabilia show, it made me realize we were once the best. I bought it and became inspired to learn as much as I could about the team. I've since added uniforms, balls, pennants, and even a player's passport. I've invested about $150,000 and I could sell the collection for three to four times that. But the reality of sports memorabilia is that you buy something because you like it. Ultimately, the collection shows my dedication to my hometown and its oldest team—an organization that has waited longer to win the World Series than any other. I think it's about time we win again. Here are my favorite pieces in my collection.

Crank It

The director of cycling's hottest team shares his gut-busting fitness routine

Life forced me to shift gears. A few years ago, I retired from a decade-long professional cycling career and started selling commercial real estate. Between driving prospective clients around, pushing paperwork, and spending evenings with my family, I didn't have time to exercise. Within months, I realized that a spare tire was forming around my waist and that my core strength had waned. I was used to riding 700 miles a week and eating whatever I wanted—particularly the rich, calorie-laden pastas and meat dishes I'd acquired a taste for during my travels through Western Europe. That lifestyle simply wasn't possible anymore.