The gig: Chris Hollod, 33, is venture capital partner at billionaire Ron Burkle's private equity firm Yucaipa Cos. They've traveled together for the last five years, with Hollod as the frontman on evaluating thousands of start-up investment opportunities.
Hollod oversees Inevitable Ventures, backed by Burkle and musician D.A. Wallach. Inevitable's portfolio includes Common, Thrive Market and 8i — which are seeking to reimagine industries such as hospitality, groceries and entertainment that brought Burkle his fortune. The magnate's personal investments in start-ups such as meal-maker Munchery also run through Hollod.
They partnered with actor Ashton Kutcher and Madonna manager Guy Oseary on investment firm A-Grade. By backing Uber, Airbnb, Spotify, Nest and Chegg, A-Grade's value has grown to $250 million, or about nine times the principal.
Risk-averse: A star in academics and soccer, Hollod considered Ivy League universities. But he opted for Vanderbilt, or what he calls the Harvard of the South. It was closer to his parents' suburban Atlanta home and less feisty of a culture.
"I wanted to be a big fish in a small pond," he said.
Staying conservative: Studying finance and economics led Hollod to a two-year investment banking program at Wachovia in Charlotte, N.C. He considered higher-tier banks but wanted to avoid their reputation for a "sharp-elbows" lifestyle.
Coasting: In a rare feat for someone his age without a master's degree, Hollod became an associate at Wachovia. He moved in with his girlfriend, with an eye toward marriage. He felt like a high roller in Charlotte, on his way to running Wachovia someday.
A crushing wave of change: His mother died at age 53 after a two-year battle with cancer in 2007. Wachovia laid off his entire group amid the financial meltdown. And Hollod and his girlfriend broke up.
Single, jobless and grieving, he reached what he calls his life's most-defining moment. Some might have turned to drugs or seclusion, Hollod said. He drew inspiration from the strength of his mom, who maintained her life-of-the-party charm until the end.
Going forward, people will only "know who my mom is through their interactions with me, and I'll be damned if they think anything less of me or my mother," he recalled telling himself. "I treat everyone with respect … and I'm honest and hard-working, so people know how I was raised and the mother that she was."
He ventured to a lake house to hike, grill and wakeboard with his younger brother and their dad, an environmental engineer with a doctorate degree. There, Hollod decided to recalibrate by traveling to California for the first time since early childhood.
LinkedIn: Hollod couch-surfed (and beach-surfed) with two friends in Southern California for a month, falling in love with the region's comparatively casual vibe. An insight dawned on him.
"Why does this dichotomy of big fish, small fish exist?" he said. "What's more admirable than the pursuit of a big fish in a big pond? I said, 'I'm going all in. I'm not moving to another small city.'"
He messaged about 100 people on LinkedIn and Facebook for a lead on a finance job in Los Angeles. A younger Vanderbilt classmate he hadn't spoken to in years — and even then only briefly knew — was among the respondents.
A low-level employee at Yucaipa, she said she would forward his resume. Hollod had an interview a month later, and within a week drove cross-country to start at Burkle's firm in October 2009.
Entrepreneurial: Hollod became more proactive, constantly asking bosses for tasks and trying to get himself into every meeting. The energy got rewarded. Executives pointed to him when an opportunity opened a year after he started for someone to be Burkle's eyes and ears on the fund with Kutcher and Oseary.
Key trait: Hollod describes his knowledge as vast in terms of subjects, but shallow on any given topic. He's fine with that because the broad spectrum makes him fast on his feet with anyone.
Take heed: Hollod expects entrepreneurs to describe not only their biggest mistake, but also the lesson derived from it. His own example is not investing in online mattress retailer Casper early on because Burkle and Kutcher questioned its prospects (A-Grade later invested in Casper and cashed out some shares, generating a more modest eight-fold return). Now, Hollod is willing to place small bets with his own money regardless of others' support. He aligns himself with Burkle by co-investing, including in restaurant chain Sweetgreen and aerospace start-up Planet.
Channeling mom: Hanging with the rich and famous can steer people toward clubs, drugs and potential vices. But Hollod said he avoids such traps by doing only what his mom — a People magazine fan — would be proud to read about.
Advice: Don't send canned messages. Notes should have personality and confidence behind them, Hollod said.
"When you're writing an email, the time of day, what you had to eat, it's a different energy," he said. "Be more sensitive to the situation; don't make it sterile."
Treat celebrities like a new friend, meaning strike up a conversation and don't just ask for a selfie. Get over any shyness or fear of them, and don't make preconceived judgments.
"I've seen [Kutcher] sit in a middle seat on a regular plane," Hollod said. "Some of these people will surprise you."
Personal balance: Hollod, who arrived from New York City on Burkle's jet at 4 a.m. on a recent weekday, went on a Runyon Canyon hike, rested and then worked poolside at home until sunset. He says post-travel "exiles," including time spent playing chess on his smartphone and streaming hip-hop music, keeps him balanced.
Hollod is a connoisseur of Pinot noirs, favoring Babcock and Melville wineries. His family plans to launch a wine label named after his mother in the coming weeks and donate profits to charity.
He's thought about writing a book for young adults, urging them to break free from complacency and norms. He'd title it "Big fish, Big pond: Breaking the Dichotomy."