It's not easy to break into either Hollywood or Wall Street. Aaron Siegel has carved out a place in both.

As head of Goldman Sachs' entertainment investment banking business, he oversees a team of bankers who work on deals spanning a range of sectors, from live events and video games to television and movie production. His team represented amusement park owner Cedar Fair in its $8 billion merger with Six Flags last year, and Niantic, the video game maker behind the hit franchise "Pokémon Go," in its $3.5 billion sale to Saudi Arabia-owned Scopely.

This year, he was named to Billboard's annual list of its Power 100 list — and was ranked No. 8 on the publication's list of finance sector professionals.

As a former Hollywood reporter who now covers Wall Street, I was curious to hear Siegel's thoughts on the future of entertainment and his advice for making it on Wall Street. Siegel joined Goldman as an analyst more than 20 years ago and last year was elevated to partner, the firm's highest rank outside the C-suite.

He said that when the entertainment banking group launched as an independent business line in 2021, he was its sole managing director. Today, he oversees a team of four MDs, including Hemal Thaker, who spearheads the gaming and interactive entertainment business; Gaurav Madan, who handles M&A execution; Jack Kamine, who looks after film, television, and content; and Evin Broder, who's focused on live entertainment, and entertainment services and growth.

Jenny Kim, a managing director at Morgan Stanley, joined in June to lead the bank's music business.

Goldman's expansion comes amid sweeping upheaval in the entertainment industry—from the 2023 dual strikes over AI and labor concerns to climate disasters like California's $250 billion wildfires and mass evacuations.

Here's a look at our conversation, edited for length and clarity.

I'm often up early enough to go for a jog through Central Park. It is a global business, and we generally have something fun happening. So as I make my way to the park, I'll check in with our teams in Europe and Asia working on projects. This week, it was teams in Stockholm and Singapore. Stockholm, especially, is a vibrant epicenter for the world of music production.

Once I'm in Central Park, there's nothing better than just having some time surrounded by the earth and the trees. And there's no better way to end a day or a week than with a Little League baseball game, one of my kids' music performances, or getting a chance to attend a religious service performed by my wife, who's a rabbi at a temple here in New York.

When I joined the firm 22 years ago as an analyst, I had the privilege to really be in the trenches with our clients, building those relationships. So I really try to encourage and ensure that our entire team is getting that exposure and building those relationships.

I am inspired by the incredible creativity and tenacity of our clients, and I want our junior bankers to experience working for the most creative entrepreneurs and people in the world.

Entertainment is a very broad sector, and there are sectors within it, like music and video games, that have grown consistently in recent years.

In Hollywood, film and TV production have gone through a period of just epic challenge from the pandemic to the evolution of the streaming wars — as well as the 2023 actors' and writers' strikes and the LA fires. But I believe from the work we're doing with our clients that the environment for film and TV content has stabilized and is now growing again.

Audiences have re-embraced the theatrical experience at the movies, and the scaled streaming services are on a very strong footing.

It makes sense that companies are uncoupling their businesses so that each have their own capital structures, management teams, and strategic direction. I believe that this will also help people start to operate again from a position of stability and strength.

AI is influencing every transaction we work on right now.

We are seeing AI empower creators, writers, songwriters, and directors. It's making content creation easier and more widespread.

Among our client base, AI is proving a win-win for everybody.

I look to music as an example. There're over 100,000 songs uploaded to streaming platforms every day. And share has shifted as a result to independent and DIY artists.

The majors have benefited as well because of their expertise in elevating artists to global superstars. Their knowledge in this environment becomes all the more important since they have the intuition and models to help artists reach the next level.

I will never forget being at South by Southwest for the premiere of "Everything, Everywhere, All at Once" for one of our studio clients in 2022. I was not even remotely prepared for the grandeur, the emotion, the intensity of that experience in that film. For me, it was an unexpected story about parenthood and having young kids at that moment watching that movie — I did not go into the journey expecting to be so moved.

This is a career that celebrates achievement by changing your role. So as an analyst, you spend two or three years mastering modeling. As an associate, your task is to oversee the narrative of presentation materials. And once you master that, you are then moved into a new role where as a VP managing projects and the day-to-day work with clients.

And these are all wildly different roles requiring you to build different skills. And so my advice would just be to enjoy that experience, embrace the fear of new challenges.

And if you do, you probably won't find a lot of moments of boredom throughout the journey.

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