Jesse Itzler wants you to chase two kinds of wealth. And he wants you to refuse to trade one for the other.

Itzler, a serial entrepreneur and best-selling author, spoke Friday at Ignite, the customer conference for FieldRoutes and Aspire customers. DJ Dee Wiz joined Itzler on stage, dialing up tunes to complement a presentation that included video, images, and even a customer singalong.

Itzler’s lesson began at a checkerboard. Itzler’s father, Dan, never let his son win. He showed no mercy when Itzler was 4, heckled him at 7, and at 13 still won after removing his own back row. The message: nothing gets handed to you, even by your dad.

Itzler finally won just a few years ago, late in his father’s life. 

“What I didn't tell you,” Itzler told contractors, “is that when I beat my father in checkers, he didn't know who I was. Because my dad had Alzheimer's.”

His children spent six days in hospice holding their father’s hand around the clock, and Jesse Itzler found he had no regrets. 

"Empty the tank, and you're going to feel really good about it at the end of the day," Itzler said. 

He had poured his soul into the relationship, and so had his father. His father never amassed a fortune, but he mastered the other kind of wealth. 

"If you have a billion dollars and your spirit is zero, a billion times zero is zero," Itzler said. "But if you have $1 — $1! — and your spirit is a billion, a dollar times a billion is a billion. 

"My dad was a spiritual billionaire."

More takeaways from Itzler’s talk:

1. Measure success with SIPPS

When Itzler researched senior living for his parents, he found that facilities grade residents on five criteria: social, intellectual, physical, purposeful, and spiritual. 

Money didn’t make the list, and neither did social media followers, watches or cars.

2. Put yourself where luck can find you

Locked out of a conference where his prospects gathered, Itzler bought every muffin at the coffee shop next door and struck up a conversation with an attendee who needed one. 

That conversation became his first sale. 

“The universe rewards the bold,” Itzler said.

3. Compliment, congratulate, and console

After the first Marquis Jet (a private jet card company) sale, Itzler handed his customer a list of vetted pediatricians and booked spring break dinner reservations. He kept showing up in good times and hard ones, and the customer stayed loyal. 

“Business can be transactional,” he said. “Relationships can’t.”

4. Act with urgency

Itzler’s mother asked him to take her to a castle in London when he was in his 20s, 30s, and 40s, and he was always too busy. 

In his 50s, she couldn’t go. 

Work, sleep, meals, and screen time claim about 75% of the year’s 8,760 hours, he told contractors, so he urged customers to be diligent with the other 25%. 

“When you have a chance to create a memory or a moment, you take it,” Itzler said.

5. Rip up the playbook

Itzler asked the room, “If nobody taught you how to do your job, how would you do it?” 

That question is where innovation and disruption begin, along with a second one: What makes you and your product uniquely different?

6. Watch the words you speak

While training for a 100-mile foot race, Navy SEAL Chad Wright gave Itzler one rule: Never give pain a voice. 

If Itzler was asked how he felt, the only answer was “outstanding.” 

In the 75th mile of the Hennepin 100, Itzler shook with hypothermia and could barely move. Walking beside him, Wright shared a secret: He never gets tired.

When they got inside an aid station, Itzler took a seat.

“Chad grabs me by the shirt, ‘let's go!’” Itzler said. “Mile 75, how do you feel? I feel outstanding, Chad.” 

“77 miles in, there's no one near us. ‘I don't get tired, Chad,’” Itzler said as Bill Conti’s “Going the Distance” from Rocky began to build.

“80, 82 miles. ‘I feel outstanding, Chad.’

“Eighty-five, 87, 89, 90, 92, 95, 97, 99, all the way to the finish line of a 100-mile race. 

“The words you speak matter.”