3 Key Lessons For CEOs And Founders Needing A Creative Breakthrough - Kathy Caprino

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Advice, Amazing Career Success, Breakthroughs, Careers, Creativity, Inspiration for Change, Inspiring Thoughts, Leadership, Professional Growth, Thought Leadership 3 Key Lessons For CEOs And Founders Needing A Creative Breakthrough Written by: Kathy Caprino

Part of Kathy Caprino’s series “Today’s True Leadership”


According to recent data and research, creativity has been ranked as a top skill for business success today. In a 2020 World Economic Forum “Future of Jobs Report,” creativity was rated highly as an important emerging skill across numerous countries. But very often, seasoned CEOs and leaders can rely too heavily on what they’ve done in the past that has been successful, when in fact, something brand new is called for. As an example, research has shown that novice CEOs consistently outperform more experienced leaders, in part because the more experienced CEOs “fall back on the playbook from their last job, become overly concerned with cost-cutting, and are less adaptable than rookies…”

To learn more about how CEOs and startup founders can achieve creative breakthroughs for their businesses, I caught up this month with Joey Boukadakis, founder of the advisory firm General Specific. He works with CEOs of new media, tech, and web3 companies with a focus on creative strategy advisory. Boukadakis previously cofounded Wheel, a mobile video technology startup acquired by Tinder in 2017, and worked in creative development roles at MTV, Warner Brothers, Disney, MGM, Paramount, HBO and Comedy Central.

Here’s what Boukadakis shares about how leaders can achieve creative breakthrough:

Kathy Caprino: Joey, as a creative strategy advisor to some of tech’s top CEOs, what does your work focus on?

Joey Boukadakis: I help CEOs solve complex creative challenges and scale creative tech businesses. That work looks different for each CEO, but the role is a perfect combination of my experience as a creative and executive in Hollywood, and as an entrepreneur, building and selling my own media tech startup to Tinder and IAC.

Originally focused on entertainment, I graduated from USC film school and started my career as a music video director, working with artists like Black Eyed Peas, Linkin Park, Lil Jon, Thirty Seconds to Mars, Liz Phair, Marc Broussard and more (back in the day when MTV actually played music videos).

From there, I transitioned into screenwriting and wrote and sold a good number of movies and TV shows to studios and networks like MGM, Comedy Central, CBS, Disney, and HBO (where I worked on the “Entourage” franchise).

As I was writing, I also grew interested in gaming and went on to run a digital gaming group inside Warner Brothers, producing properties around global IP like Batman and Harry Potter. As media continued to evolve with the inflection of smartphones and consumer apps, I began to feel more and more drawn to technology and entrepreneurship, eventually raising VC money and starting a tech company with my brother—a mobile video collaboration app called Wheel, which we ended up selling to Tinder and IAC a few years ago.

Going from fledgling startup to acquisition by a Fortune 500 company was exhilarating; we learned a lot of lessons along the way. Coming out of the sale, I recognized how valuable an entertainment and content background could be for the right kind of tech organization, and identified a white space opportunity from the advisory side. Growing our startup, we utilized the help of all kinds of incredible advisors—financial advisors, legal advisors, and IT advisors—but no one was really doing what I today call “creative strategy advisory,” and it would have been extremely meaningful for us.

I ran with this insight and started helping out CEO friends with their businesses—companies with some kind of content, original IP, creative tools, media tech, web3, gaming, or platform component to them. It unearthed a real demand for the work, leading me to launch my own strategy advisory firm called General Specific, which I run today.

I’ve fused my experience, relationships, expertise, and intangibles across entertainment and the startup community to advise, work with, and invest in many incredible businesses. Focusing on early and growth-stage new media, tech and web3 companies, since inception, I’ve been fortunate to advise businesses like Tinder, Masterclass, Citizen, GoPuff, Raya, Green Dot, Artie, Invisible Universe, Masters, Popchew, Joyride and more.

What I spend a lot of my time on falls into a handful of advisory buckets. I work directly with CEOs to architect and implement a creative vision for their company, then execute on it. I develop original IP and content strategies using Hollywood storytelling talent to cut through the fray and facilitate entertainment and media partnerships across talent agencies, studios, networks, and brands. I help drive inventive growth and scale initiatives and bring in strategic investment capital from different ecosystems. Ultimately, I find ways to provide innovative and disruptive companies with equally innovative and disruptive creative solutions.

Working across a diverse kaleidoscope of CEOs, creative challenges, and industries means my days are uncommonly dynamic, colorful, and, dare I say, fun. Most of the CEOs I work with express they want to come join me after we properly scale or sell their company. An advisory firm comprised of all former creative tech CEOs? Yes, please.

Caprino: So how does your background as a Hollywood creative shape the work you do for tech companies?

Boukadakis: It informs almost everything. Success in Hollywood depends on multiple factors including original idea generation, storytelling, and collaboration. I work with CEOs to help them build strategies for implementing this mindset within their organizations. Tactically, this can present itself in a variety of ways.

For example, when companies like Tinder, Masterclass, and Invisible Universe need help with original IP and content development, I bring in a brain trust of exclusive Hollywood screenwriters from TV shows like Happy EndingsFamily Guy, The OfficeBig MouthBreaking BadVeepEntourageWeCrashed, and more, using a “writer’s room” style approach to brainstorm and “crack creative” in a unique, nontraditional way.

Hollywood has the highest concentration of artistic brainpower in the world; by refocusing it through a business prism, we help companies foster new ways of solving creative problems, be they content initiatives, brand campaigns, or AR experiences.

Many of the companies we work with also require access to or relationships with Hollywood institutions such as talent agencies, management companies, movie studios, networks, and entertainment brands in order to drive partnerships and growth. So, be it an experiential marketing stunt for mobile gaming company Joyride with Paramount Pictures—or tapping into talent collaborations via Hollywood agencies like CAA and UTA for Popchew, a virtual food brand platform—by facilitating entertainment partnerships opportunities for clients, I’m able to generate value on both sides of the equation, as entities in Hollywood also want to work with compelling Silicon Valley tech startups.

As an advisor, I also use my entertainment background to bring strategic investment capital from the Hollywood ecosystem into startups, adding star power and high-profile names to boards and cap tables. Over the past several years successful athletes, musicians, celebrities, influencers, and executives such as The Chainsmokers, Kygo, Kevin Durant, Serena Williams, Kevin Hart, Snoop Dog, Charli and Dixie D’Amelio, Jeffrey Katzenberg, Kevin Mayer and more have become more involved in the investment space, many raising their own designated VC funds or SPACs, leveraging their social footprint and marketing reach to participate in and add value to equity funding rounds.

For a tech company, having a differentiated investor base with deep entertainment roots outside Silicon Valley can be a powerful advantage.

Ultimately, I’ve found that Hollywood creatives and tech company innovators have a lot in common: they’re bold thinkers, unafraid to disrupt the status quo, and they understand what emotionally resonates with people. But it’s quite uncommon for people to jump between the two industries. I have the benefit of years of experience in both—so I’m able to make connections and bridge the gap for truly impactful and asymmetric results.

Caprino: What are your top strategies for helping often left-brain CEOs unlock their inner creative/artist and tap into their right brains?

Boukadakis: Creativity is about connecting disparate concepts until you’ve come up with something entirely new. Making connections is almost mathematical—an act of analysis, or logic. So, it’s not necessarily a battle between left-brain/right-brain, but figuring out how to harness a CEO’s specific strengths as a wedge into creativity. Breakthroughs often come from combining elements that may not ordinarily belong together. One of my tried and true strategies is to encourage “associative thinking” for CEOs and help them connect the unconnected.

Caprino: Why do you think many founders who had immense creativity when they first started their companies ultimately stagnate?

Boukadakis: It often comes back to the old adage: “what got you here, won’t get you there.” If you stop taking creative risks and searching for new wellsprings of inspiration, an organization can shrivel and die. It can be daunting, but CEOs should be willing to cannibalize their own initial creativity and constantly reinvent. The challenge rests not so much in manifesting new ideas as in escaping from old ones.

Caprino: What can small business owners learn from your work with CEOs and highly recognizable businesses and brands? What can they do to expand their creativity and innovation?

Boukadakis: Great CEOs and businesses are willing to experiment and take risks to find breakthroughs. It’s easy to do what everyone else is doing. Anyone can buy performance marketing ads across social media—there’s little innovation or leverage there. Viewing your business through a creative prism, or asking the question “how do we do something the world has never seen before?” or “how do we attempt to make something undeniably great?” isn’t delusional—it’s an antidote to atrophy. The safe competitor can always be taken down by someone willing to take risks and be noisier. In a crowded marketplace, success favors the bold.

Caprino: What are your three best tips for CEOs and founders, and other leaders, to innovate at the highest level?

Boukadakis: Here are my top tips:

Think and execute creatively

In the future, anything that can be automated eventually will be. But creative work is its own form of leverage and very hard to teach. The ability to think and execute creatively is a tremendous competitive advantage. It pays to have a differentiated point of view.

Throw yourself into change

Embrace change because it’s coming. The goal is to be on the right side of technological disruption and creative innovation. To do so, it pays to be perpetually curious. In business you have to divine the zeitgeist a few years ahead—where do people’s needs, desires, and frustrations lie? Inculcate a culture of curiosity and actively take risks to disrupt yourself in order to invent the future, rather than get steamrolled by it. Remember, your job as CEO is not to protect your current business but to build newer businesses faster than the old ones decay.

Fuse data with intuition

Lastly, I think making room for both data and intuition, science and art, the quantitative and the qualitative in business is paramount to building inspired companies that last.

The Italian entrepreneur, Brunello Cucinelli, has said that he wants his company to be a place where both “the Enlightenment and Romanticism, reason and beauty, blend together. A great idea that is born out of the mind and then goes through the soul—there is no doubt that will lead to something special, a marvelous outcome.”

I’ve always responded to that sentiment; it’s indicative of the creative spirit and attitude we help CEOs and companies strive for every day.

For more information, visit General Specific and Joey Boukadakis.

Kathy Caprino is a leadership and career coach, author and speaker helping high-potential women achieve greater success and impact.

Follow me on Twitter or LinkedIn. Check out my website or some of my other work here.