Key Insights from the 2023 Cultural Leadership Summit

Megan Holston-Alexander

In true CLF fashion, we brought together leaders across entertainment, sports, music, and business and tech at our annual Cultural Leadership Summit to celebrate the undeniable influence and impact of culture, and foster real connections to build the future together.

Our program featured the voices of prominent speakers who are creating, shaping, and shifting culture. We wouldn’t be doing our jobs if we held onto the knowledge and pearls of wisdom from these conversations. In that spirit, here are the top insights gleaned from our speakers:

1. Autonomy, Ownership, Equity

Bet on yourself and your value early on–even before you have the success to show it. Betting on yourself and being your own biggest supporter requires you to leverage the people and tools that allow you retain control of your work and equity.

While on the road playing small comedy clubs early in his career, Kevin Hart handed out info cards to capture names and email addresses of his fans. This was the start of owning and managing “a database” that eventually grew into a community of nearly 180M followers on Instagram alone. Not only did it help Kevin create an opportunity to forge direct connections with fans, it also gave him valuable leverage in negotiating deals with comedy clubs and theaters.

NBA star Jaylen Brown was seen as an outsider when preparing for the draft and his rookie season. Jaylen was the highest pick in the draft that did not have the representation of an agent. Instead, he advocated for himself and leaned on those around him that he trusted, including the NBPA. While there were plenty of skeptics and naysayers, Jaylen got to where he is, with the largest contract in NBA history at the time, by trusting his work, skill, and intuition.

This is a priority not just for athletes and entertainers, but artists and creators of all kinds as they produce work, build direct relationships with fans, and grow their brands and businesses.

2. Value Curiosity and Discomfort

Kevin Hart put it best, “No question gets answered that doesn’t get asked.” Pushing into new arenas can feel like a difficult and vulnerable position. But making next-level moves requires discomfort and learning something new.

While the worlds of investing, venture capital, and technology may seem daunting, a running lesson that leaders shared was to dive in head first: meet new people, ask the questions, follow up, get as much information as possible.

From his initial skepticism of venture capital to now managing HartBeat Ventures, Kevin turned his discomfort into knowledge and currently invests in entrepreneurs building the future of tech, media, and entertainment.

This is true for any industry or endeavor and is a critical perspective to have in order to be successful.

No question gets answered that doesn’t get asked.
Kevin Hart

3. Don’t Stand on the Podium Alone

One of the most common themes we heard relayed on stage is something that may seem obvious, but doesn’t always happen in practice: once you make it through the door, keep it open for others.

When given a platform, do you stand alone on the podium or do you put shine on others that are coming behind you?

Jaylen Brown’s story is a perfect example. At the press conference announcing his signing as the most lucrative deal in NBA history, he put a spotlight on students who participate in The Bridge Program, part of his 7uice Foundation. This program focuses on four key areas: Entrepreneurship and Financial Literacy, Health and Wellness, Leadership and Activism, and finally, Sustainability and Technology.

Not only did the students he works with participate in the press conference, Jaylen focused his comments to press on the unsettling wealth gap in Boston and his vision for building Black Wall Street in the city. This is how Jaylen is using his platform to highlight and elevate others versus heaping all the attention, praise, and credit on himself.

Athletes have a tremendous platform. We know the attention is on us. Let me divert the attention back where it needs to go.
Jaylen Brown

4. Turn Pressure Into Responsibility and Action

Success is something to be celebrated, but along with more visibility and a larger platform, comes immense pressure and scrutiny. Leaders addressed managing, living, and working in a fishbowl with eyes always on your every move.

Preparation and taking the responsibility of your position head on offer a way to turn pressure into drive. Earvin “Magic” Johnson explained how he likes that pressure because it pushes him to stay over-prepared for any situation and ultimately get the job done well.

Kevin also reflected on making sure we all do something with the ball. There will be pressure and scrutiny but can you depend on yourself to go put some points on the board? Not being afraid to fail allows us to take calculated risks and opens up more opportunities for those who lean in.

I like pressure. It’s what gets me going. That pressure allows me to do my job and do it well.
Earvin “Magic” Johnson

5. Embrace AI’s Potential for Creativity & Growth, for Everyone

AI is on everyone’s mind! A key topic at Summit was how to put AI to work in creative industries, with artists and entertainers contemplating the best ways to use AI as a co-pilot in their creative processes and businesses.

a16z Cofounders Marc Andreessen and Ben Horowitz shared the history behind technology supercycles like we’re seeing with AI. In the music industry, for example, every wave of new technology was followed by the introduction of a new genre of music: the saxophone birthed jazz, the electric guitar, rock n roll, the drum machine, hip hop, and so on.

For new artists and creatives, this new wave of generative AI represents a whole new canvas from which to build and create.

If the theory of technology eliminating jobs is correct, we’d all be sitting around with nothing to do and mass unemployment everywhere.
Marc Andressen

If you’re a new creative, if you’re someone who wants the biggest canvas in the world, you just got it.
Ben Horowitz

The Cultural Leadership Fund was born out of asking the question: what happens when you connect the world’s greatest artists, entertainers, athletes, and executives–those who are creating, shaping, and shifting culture–with founders and builders of innovative technology? How can we best combine the strengths of both cultural leaders and entrepreneurs?

What we have seen over the past 5+ years is that this partnership can produce new ideas, new opportunities, and new culture faster than going at it alone. At the same time, it allows for greater equity and opportunity to participate in the technology industry.

The Cultural Leadership Fund is excited to continue to highlight this intersection of culture and tech, and think about new waves of innovation and creation. This community is an important one and we look forward to building the future together!

We have a group that’s so great at driving or changing consumer behaviors, creating new ideas, new culture, new ways of doing things.

If we combine those with people who are really good at computer programming, maybe we can make a lot more progress, a lot faster.
Ben Horowitz

Software is eating the world.

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