Chase Jarvis's Unconventional Path from Celebrity Photographer to Anti-Unicorn Entrepreneur
From photographing the world's biggest celebs to running a venture-backed startup, Chase Jarvis discovered that playing Silicon Valley's game means losing your own. Here's why he'll never chase a billion-dollar exit again.
Written by: Paige Bennett Photography: Provided by Chase Jarvis
Summary
- From photographer to CEO: Chase Jarvis went from shooting icons like Lady Gaga and Serena Williams to building CreativeLive, an online learning platform that scaled to $35M in annual revenue with top-tier VC backing.
- The VC reality check: Despite growing 40% year-over-year, Jarvis learned his "successful" business wasn't considered interesting enough for investors seeking billion-dollar returns, a painful lesson in how venture capital actually works.
- Losing himself in the process: While chasing traditional startup success, Jarvis realized he'd been seduced into building what the world wanted rather than staying true to his authentic, creative vision.
- The anti-unicorn approach: After CreativeLive's acquisition by Fiverr, Jarvis pivoted to a portfolio model — holding stakes in multiple companies, coaching founders one-on-one, and building six stealth startups inspired by Richard Branson's 400+ business approach.
- Endurance over innovation: Jarvis's key takeaway is that outlasting competition matters more than being first, passion is your only real competitive advantage, and success without fulfillment is "the ultimate hell."
Introduction
The path to becoming a CEO certainly wasn’t linear or traditional for Chase Jarvis. Before heading CreativeLive, Chase wore many hats, from pursuing professional soccer to bailing on medical school to becoming one of the leading commercial photographers in the world.
Yet at the peak of his photography career, after capturing icons like Lady Gaga, Serena Williams, and Tony Hawk, he then turned his focus toward running a venture-backed startup.
“I was seduced by the next challenge... oh, this is the next step in the entrepreneurial journey,” Jarvis shares as he sits in his Seattle studio reflecting on the decade he spent building CreativeLive, an online learning platform for creatives.
But whether he was kicking a ball down the field, snapping photos destined for millions of views, or helping inspire and educate creatives around the world, Chase credits his success — real success, not just what the world says success is — to curiosity and passion.
“If you don't write your own script, other people will be more than happy to write it for you,” Chase said.
His path from athlete to creative to CEO taught Chase three uncomfortable truths about startup success: don’t fall into building someone else’s dream, endurance is your only real competitor, and the anti-unicorn path might just be the smartest play.
Part I: When Success Becomes Someone Else's Script
The Seduction of Silicon Valley
A combination of passion, dedication, and luck helped move the needle on Chase’s photography career, ultimately catapulting him into massive success.
But in addition to capturing photos, he also shared stories about why he loved photography online, ultimately building a strong community that followed along with his journey. With this community, and by honing his technical skills, he was able to grab the interest of major brands and get hired for multimillion-dollar photoshoots globally.
“The passion that I felt around photography made it easy for me to work really hard,” Chase said. “But what most people don't talk about is all the luck that is involved in cultivating success for yourself.”
It was Chase’s online community, and his sharing of photography’s “inside secrets” at a lucky time, that piqued his interest from the more creative side of photography to what could be a lucrative career in a venture capital-driven business.
He began livestreaming behind-the-scenes on assignments, garnering 25,000 to 50,000 views, and then built an early version of what would become CreativeLive. Anyone could watch these streams for free, but replays would come at a cost. This then turned into a subscription model, all built from his personal storytelling and branding.
“The idea of building a personal brand, a platform, was so new at the time — and I know it's impossible for people to think back that far — but you could do that with very limited means.”
The community, passion, hard work, and luck allowed Chase to grow as a wildly successful photographer. According to Chase, he started making “stupid money” as the world’s most-followed photographer. He was able to build a creative studio during a time when he felt like he was “creating all my wildest creative dreams.”
But then, there were those people urging him to launch a tech startup, with seductive promises like reaching tens of millions of people, making a couple billion dollars, and scoring a private jet.
“I don't know who is not seduced by that, and I wish that I was not,” Chase said.
The Venture Capital Trap
Thus became CreativeLive, an online learning platform that continued to rapidly gain momentum, even scoring some of the best investors in the world — with backings from the likes of GreyLock Partners, Social Capital, and Richard Branson — without actively seeking them out.
The company raised a successful round and continued to grow, so Chase tapped a CEO to handle the business side of things while he focused on creative. But true to the company’s mission to teach, Chase himself was able to learn more about the inner workings of running a business of this caliber. When the CEO moved on, Chase felt more confident in his abilities to take over.
“In the process of doing that, you get really involved, and you know a lot about what these venture capital folks want and need,” Chase said. “I had turned around the company after the first sort of arc, and we were doing $35 million a year in annual revenue, growing 40% year-over-year.”
With 10 years of scaling and hitting higher growth marks than ever, Chase felt ready to fundraise again by this point, and he discussed this possibility with his lead investor.
Then came a crushing moment where reality set in, when the investor responded, “I don't know how to say this, but … it's just not that interesting, the business.”
Venture capitalists are looking for massive returns, so even if you seem successful, you could still be falling far short of what VCs are looking for.
“They want to invest 10 million and get out a billion,” Chase explained.
It may have been a painful lesson, but it allowed Chase to take on a deeper understanding of VC, its challenges, and why Total Addressable Market was so important for startups. Even if your startup makes millions and has a solid, satisfied customer base, VCs are looking for more. Venture capital isn’t always the right path and can be extremely difficult, even for the most promising companies.
Not to mention that venture capital may not always pan out the way you think. At the height of the COVID-19 pandemic, having an online learning platform was extremely lucrative, but even still, unique circumstances made it difficult for CreativeLive to continue fundraising despite its success.
At the time, one of CreativeLive’s main board members and two of its lead investors changed course in their own businesses, leaving CreativeLive to have to find new fundraising sources — after years of building those relationships — during an already challenging and volatile time.
Like many other similar businesses at the time, CreativeLive ended up taking the M&A route, while only a handful of online learning platforms went on to IPOs.
“We didn't stay independent. We were acquired by a big public company called Fiverr, which is an online creative marketplace,” Chase explained. “It was fine, but I’m not a billionaire, despite having essentially the first sort of real thumbprint in a world of online learning.”
CreativeLive’s journey lays bare the difficulties of playing the venture capital game, even for trailblazing startups.
Life is not about making mistakes. It’s about recovering quickly, and each time you make a mistake, you’re becoming 1% better.”
— Chase Jarvis, co-founder of CreativeLive
The Cost of Playing Someone Else's Game
In the midst of taking over as CEO and pursuing further venture capital, Chase ultimately began to lose what made CreativeLive so incredible in the first place: creativity and passion.
Today, Chase looks back on this time as feeling seduced by the world and pushed toward traditional markers of success.
“If I was able to listen to my own intuition perfectly 100% of the time, that intuition would have said, ‘Hey, Chase, you're getting sucked into what the world wants for you rather than what you want for you,’” he said.
The world can write your story for you if you let it, and Chase warned other creatives and entrepreneurs to stick to who they are and what makes them unique and passionate, rather than chasing success.
“This thing that we call life is just a series of tiny betrayals of who we really are,” he shared. “Despite all the external success, there were things that were going on behind the scenes. I was constantly getting pulled into things that weren't authentically who I was.”
Ultimately, CreativeLive was successfully acquired, and it made a considerable mark on its industry. Although betraying his authentic self along the way was perhaps a mistake, it’s one that Chase has since learned and grown from, and he’s offering up that knowledge to anyone who’s also trying to pursue their dreams.
“Life is not about making mistakes. It’s about recovering quickly, and each time you make a mistake, you’re becoming 1% better, 1% more kind to yourself, 1% smarter, more thoughtful than the time before. And you do that over and over and over.”
Part II: The Anti-Unicorn Revolution
Chase Jarvis 3.0: The Portfolio Approach
The acquisition of CreativeLive was just the next milestone of Chase’s career. After the company was acquired, he spent a year as an executive during the transition, then took two years off to rediscover his passions.
Now, Chase has evolved into the next stage of his career: portfolio building.
“I know that I love helping creators and entrepreneurs build a living and a life that they love,” Chase said. “While I was doing that at CreativeLive, I was doing that for 10 million people, and now I want to do it for 10 people.”
Today, Chase offers one-on-one coaching and holds 10% to 50% stakes in various companies, whether they are companies born from his own ideas or offers brought to him. He’s even building six startups in stealth mode to be announced by the end of this year.
Ultimately, he’s less interested in concentrating his time and investments into just one business. Instead, Chase is inspired by Richard Branson’s ownership in over 400 businesses and is following that blueprint in his own portfolio building.
“I want to have more businesses that I have a small piece of and can help other creative entrepreneurs start lots of businesses and less operating in the nuts and bolts deeply of one business,” Chase said. “I can only say this because I've come out the other side of operating a scaled business.”
Why Multiple Small Wins Beat One Big Bet
Portfolio diversification has helped reignite Chase’s passion, both in entrepreneurship and creative endeavors. For one, there’s a sense of freedom by no longer tying his entire identity to just a single company.
“It's a fun place to be, just transparently, to be packaging and sharing a lifetime of wisdom, to have that be your job. I feel really grateful,” Chase said. “It comes at a price, but it's a price I'm happy to pay.”
In this current stage of his journey, Chase has also refocused on what drove his success early on: creativity. Now, he has the freedom to pursue photography without pressure from investors, and he works on a couple campaigns each year.
He also wrote a book, Never Play It Safe, to help others rediscover their passions and tap into their intuitions to follow their own creative pursuits, and is doing a TV show. He’s already working on his next book, too.
While Chase has had a winding road through his career and has many successful, if difficult, ventures, his ultimate takeaway is that true success and wealth come from trusting yourself, prioritizing passion, creating lasting relationships, and building wisdom.
“Success without fulfillment is the ultimate hell, in my mind,” he said. “If you have all of the material trappings of success, and you've got nobody to share it with, or you don't feel good about yourself when you wake up in the morning, that's gotta be the worst thing.”
Part III: Outlasting, Not Outrunning
The Competition That Actually Matters
Throughout his journey, Chase has learned that building a strong business is about adaptation, rather than the ability to come out with the latest app or service first.
“So much of this entrepreneur game is about outlasting the competition when things get hard,” he said. “It really is. It's a game of patience and willingness to endure pain and difficulty. That defines businesses that are more successful than others.”
The ability to succeed through endurance is clear in three major case studies: Slack, Instagram, and CreativeLive. Slack started out as a fantasy video game known as Glitch, but it failed as players found it boring. What worked, though, was the internal messaging component, which the team was able to pivot toward, eventually making Slack a household (or office-wide) name.
Then, there’s Instagram, which had started as a location-sharing app called Bourbon with a small photography feature. What later became Instagram was what Chase described as a “lift-and-stamp copy” of his own app, The Best Camera, which became Apple’s App of the Year in 2009.
But Bourbon’s founders were able to pivot to this style and convince investors that their technological backgrounds would disrupt the existing industry, leading to the wildly successful platform we know today as Instagram.
“They kicked my ass at my own game,” Chase said. “Not because I didn't beat them to a million customers, or didn't have a better platform, or whatever, but they had brute force.”
While Chase has described being outcompeted by Instagram as “his greatest failure”, he was similarly able to scale past competitors with CreativeLive. Even when competitors raised more funding, CreativeLive’s ability to pivot through challenging times helped them outlast the competition.
When Passion Becomes Your Competitive Advantage
But endurance and agility aren’t the only things that sustain startups. As Chase learned first-hand, it’s passion that is the ultimate differentiator, especially when times get hard.
“Nothing quite replaces the passion, or the combination of passion, desire, curiosity, interest,” Chase explained. “When things get hard, you will have the ability to outlast the competition.”
Despite the competition from what is now Instagram on his Best Camera app, Chase’s venture CreativeLive was able to succeed because he started it with passion. Even during a global pandemic that completely disrupted life as we knew it, CreativeLive lived on to teach students around the world.
That passion behind the startup was authentic, and it helped Chase build CreativeLive into a strong and successful business for more than 15 years (CreativeLive recently announced it would shut down in late 2025, despite Chase offering to repurchase the brand).
And now, by centering the things he is passionate about in photography, writing, and portfolio building, Chase has found more balance and success at this stage of his journey.
“Stuff will get hard. And what I find is your genuine authenticity, curiosity, passion, focus, desire to build something that serves this audience, or this particular person that you once were, which is a really good mechanism for how can you be valuable to the world,” he said. “When you are pursuing that vector, you’re more likely to not quit.”
“All of the best stuff is on the other side of your comfort zone.”
— Chase Jarvis, co-founder of CreativeLive
Conclusion: The Contrarian's Playbook
Chase has learned three major life lessons during his evolution from photographer to entrepreneur to portfolio builder:
Recognize when you’re building someone else’s dream, and have the courage to pivot back to your own goals,
- Your real competition is your own endurance, not other companies’, and
- Taking a portfolio approach, rather than banking your entire identity into one company or chasing the all-in unicorn dream, may be wisest.
But there’s a bonus lesson to learn from all of this:
Passion is the only true moat
Many successful businesspeople have sung the praises of doing what you love, but in Chase’s case, it made all the difference between simply looking successful and actually feeling and sustaining true success. Feeling fulfilled by what you’re doing is essential to driving the hard work that drives a business, whatever that may be.
As Chase sits in his studio in Seattle, preparing to announce the six startups he’s been building in stealth, providing valuable insights in one-on-one coaching sessions to other founds, and booking photography projects he’s truly passionate about, one thing becomes clear above all else: the contrarian path works.
Founding a unicorn is great if that’s really your passion. Chasing venture capital certainly works for some startups. But these aren’t the only definitions of success. These aren’t the only paths to building something that you’re proud of.
Maybe it’s time to consider an alternate route.
“All of the best stuff is on the other side of your comfort zone,” Chase said.
“Your mission, should you choose to accept it, is getting comfortable being uncomfortable.”
Author: Paige Bennett
Paige is a freelance editor and writer with nearly a decade of professional experience covering marketing, sales, and lifestyle content. Her work appears on the main HubSpot blogs, Business Insider, Better Homes & Gardens, Reader's Digest, and more. She earned her Bachelor’s degree in Journalism from Ohio University, specializing in gender studies and sustainability. Fun fact: as of this writing, she has sustained a 1,200+ day meditation streak (we can only imagine what her Duolingo streak must be!)
