ANGELES — The gig: Chris Hollod, 33, is venture
capital partner at billionaire Ron Burkle’s Los
Angeles-based private equity firm Yucaipa Cos. They’ve
traveled together for the last five years, with Hollod
as the frontman on evaluating thousands of startup
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 startups such as
meal-maker Munchery also run through Hollod.
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
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
wanted to be a big fish in a small pond," he said.
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
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.
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.
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.
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."
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.
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.
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.’"
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
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.
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.
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.
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
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.
Don’t send canned messages. Notes should have
personality and confidence behind them, Hollod said.
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
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
seen (Kutcher) sit in a middle seat on a regular
plane," Hollod said. "Some of these people
will surprise you."
balance: Hollod, who arrived from New York City on
Burkle’s jet at 4 a.m. on a recent weekday, went on a
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.
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.
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