Cooking, reading, hiking, and taking a meeting by his backyard pool is the new normal for venture capitalist Chris Hollod.
The 35-year-old spent eight years as billionaire Ron Burkle’s right-hand man but walked away from the glitz and glamour to shift his focus to angel investing and more importantly, to be his own boss.
“We’ve done over 150 deals together and overseen and started two VC funds with various compelling individuals,” says Hollod. “But I was like ‘Ron, it’s time for me to take a break and reassess my priorities.’”
Hollod joined Burkle’s private equity firm The Yucaipa Companies in 2009 and quickly moved up the ranks to manage the billionaire’s personal angel investments, serving as managing partner of venture capital funds A-Grade Investments and Inevitable Ventures.
While Hollod no longer works for Yucaipa, he is still involved at both venture capital funds. He also founded his own investment company, Hollod Holdings, with his brother Andrew, which focuses on early-stage companies.
It might seem like a big gamble to leave the offices of Yucaipa and the side of Burkle but Hollod said it’s been one of the best decisions he’s ever made.
“I wake up with a new sense of purpose and freedom,” he says. “I’m meeting a young entrepreneur by my pool every day and I just want to help them.”
The investor spent nearly 12 years in finance while pushing through a number of setbacks that happened back-to-back, from the death of his mother to getting laid off from his job to a breakup.
Those life-changing events helped shape Hollod’s approach to his personal and professional life, which he shares in his upcoming book Big Fish, Big Pond.
He added that although his mother is no longer with him, her strength and positive outlook on life continue to serve as a guiding compass and inspiration.
“The only way for you to know my mother is through your interactions with me, and I want to be damn sure you have a very positive interaction,” Hollod says.
I wake up with a new sense of purpose … I’m meeting a young entrepreneur by my pool every day and I just want to help them.
Georgia on His Mind
Hollod grew up in a suburb just north of Atlanta. While his younger brother won “Homecoming King” and “Best Personality” in high school, Hollod was much more introverted and excelled in academics and soccer.
He looked at Ivy League schools but decided to attend Vanderbilt University. It was close to home and small enough to allow him to be a “big fish.”
After graduating summa cum laude with a degree in economics, he knew he wanted to go into investment banking but didn’t want to experience the Wall Street horror stories and culture.
Hollod decided to join a two-year investment banking program at Wachovia in Charlotte, N.C. He dabbled in a number of products from debt, equity, mergers and acquisitions to IPOs. In a rare feat, he was promoted to an associate during his third year.
Within roughly 18 months, I lost my mom, lost my job, lost my girlfriend … My brain said to move back to Atlanta because that was the safest bet, but my gut said otherwise. I said, ‘You know, let me not rush into anything,’ and that’s when I booked a one-way flight to Los Angeles.
Life was great for Hollod. He would walk to work from his townhome, visit all the restaurants and nightclubs with friends, and things were progressing well with his girlfriend.
But in 2007, his mother lost her two-year battle with cancer at age 53. He was then laid off from Wachovia following the market crash in 2008 and broke up with his longtime girlfriend.
“Within roughly 18 months, I lost my mom, lost my job, lost my girlfriend,” Hollod says. “My brain said to move back to Atlanta because that was the safest bet, but my gut said otherwise. I said, ‘You know, let me not rush into anything,’ and that’s when I booked a one-way flight to Los Angeles.”
He split his time couch-surfing for about a month between Los Angeles and San Diego, where two of his good friends lived.
Hollod fell in love with Southern California’s laid-back lifestyle and hacked a plan to aggressively network his way into a finance gig. He reached out to former classmates and colleagues until finally reconnecting with an old acquaintance from Vanderbilt.
She worked for Yucaipa and passed along his resume. Within a month, he was hired and drove his 10-year-old car from Atlanta to Los Angeles.
Lifting Off in La-La Land
The job at Yucaipa was the break Hollod needed following a tough 18 months. He was determined to stand out and succeed.
“I was beating on people’s doors trying to get on deals,” he recalls. “My first deal was a bottled water company called AQUAhydrate, a startup water company co-founded by Puff Daddy and Mark Wahlberg.”
The deal not only introduced Hollod to the world of venture capital, but also jump started a new passion. His excitement and drive didn’t go unnoticed.
By 2010, Hollod was overseeing Burkle’s newly formed investment fund A-Grade with actor Ashton Kutcher and talent manager Guy Oseary. The firm backed companies including Airbnb, Houzz, Spotify, Uber, and Warby Parker.
“It was the convergence of so many different trends—mobile, social, e-commerce,” he says. “We were helping these startups and having a lot of fun doing it. In our heyday, we were doing a deal a week.”
In addition to overseeing A-Grade, Hollod began managing Burkle’s personal angel investments. He also started traveling with Burkle full-time, starting in 2011.
He then became a co-founder and partner of Burkle’s new fund, Inevitable Ventures, with musician and investor D.A. Wallach. Instead of looking at the next hot mobile app, which they felt was an overly saturated market, the firm wanted to look at startups in industries like healthcare, biosciences, and virtual reality. Its portfolio includes 8i, Memphis Meats, and Thrive Market.
Hollod credits Burkle, whom he calls a mentor, for introducing him to the venture capital world.
“I owe a tremendous amount to Ron,” he says. “He taught me so much and introduced me to so many amazing new things. I joke with my dad that I lived the life of a billionaire for six years as I traveled around with Ron on private planes and yachts.”
A New Path Ventured
The past dozen years have been a whirlwind of success, including failure and loss, and Hollod realized this year that it was time to forge his own path.
“I’m at that point where it’s time to figure things out on my own, build a family, and enjoy the work I’ve done over the last 12 years,” he says.
It’s been two months since Hollod left Yucaipa and he says it’s been great having the opportunity to read more—particularly on philosophy—and cook.
While he’s still hashing out his exact plans, he knows he wants to help startups in the health and wellness space grow their business and learn from their mistakes.
Hollod credits his own mistake—failing to personally invest in online mattress company Casper (now valued at more than $1B)—as a factor driving him toward angel investing.
A close friend from his Wachovia days called out of the blue asking if he’d meet Philip Krim, co-founder and chief executive of Casper. At the time, Hollod was still new to LA and hadn’t sourced many deals for A-Grade.
He immediately jumped on the opportunity to personally invest in the Seed round for a company he felt would be huge.
“I told it to my friends, and everyone hated it,” he says. “They’re like, ‘What an infrequent purchase. How often do you buy mattresses?’ I regrettably let my friends and advisors talk me out of it.”
That’s my benchmark with future deals—if I have that feeling I had with Casper, I’m putting my money in and standing behind it no matter what people say.
As a silver lining, A-Grade did eventually invest in Casper during its Series A round, but looking back, Hollod said he should’ve trusted his initial gut instinct.
“That investment changed my life, but I could’ve got in personally in the Seed round,” he explains. “That’s my benchmark with future deals—if I have that feeling I had with Casper, I’m putting my own money in and standing behind the deal no matter what people say.”
Photos: Dave Suchanek