Ken Sterling is a seasoned attorney, tech entrepreneur and talent agent. He passionately advocates for artists, creators, and influencers, ensuring they have prominent platforms and rewarding engagements. He’s also a respected dealmaker in the tech, media and real estate industries.
In addition to teaching at the USC Annenberg School, Ken worked as a technology and management consultant with KPMG and played integral roles in co-founding a cloud computing company and a socially-conscious bank. As part of a boutique asset management firm, he was entrusted with overseeing the legal team and real estate portfolio exceeding $300 million. In addition to his corporate roles, Sterling has a robust presence in academia and media.
Sterling earned his LLM from the USC Gould School of Law, a BA in communication and applied psychology from the University of California, an MBA in marketing and leadership from Babson College, an MA from the USC Annenberg School, and a PhD in organizational leadership from the University of California.
[Q U I C K N O T E S]
- Position: Founder & CEO of Sterling Media Law. Partner and Head of Talent Management at BigSpeak
- Industry: Law, Talent Management & Tech Entrepreneur
- Location: Los Angeles, CA
- Website: Ken Sterling Law and BigSpeak
- Personal Website: Ken Sterling
- LinkedIn: Ken Sterling
Ken, can you start off by telling us about yourself and why you chose entrepreneurship?
I grew up humble, poor actually and at times homeless. That was not a great feeling as a kid and there was a lot of uncertainty. I quickly figured out I wanted a family, security, safety and that led me to trying lots of jobs and launching companies.
Can you tell us what drives you to be successful as an entrepreneur?
In the early days, my biggest driver was to be financially stable, secure and be able to provide for my family. Back then, I was playing not to lose, vs. playing to win. Later in my career, I moved up the ladder, took bigger risks, had bigger returns and some bigger falls – my driver then was to be better and bigger. These days, my drive comes from wanting to create abundance, work with people I really admire and do good things for the world. I call it, “doing well by doing good.”
Tell us about your vision of your company in the next 2-3 years.
We follow Cameron Herold’s book, “Double Double” and have doubled in size every 3 years for the past decade. Our plan is to do this again except focus more on the “double” of profits and not so much top line revenue. It’s easier to acquire customers and service them than it is to rebuild a firm into quality, lower costs and higher margins.
What’s the one or two accomplishments that you’re proud of?
That’s a tough one, for 2 reasons. First, I am not the bragging type and on the other hand, I’ve been blessed with the ability to work with amazing people on several accomplishments I’m proud of. I was on the founding team of a bank in a Latino community – we helped farmworkers save money, not be gouged by check-cashers and get this – the ability to purchase a home, even if they didn’t have a social security number.
What advice do you have for other up-and-coming entrepreneurs?
Oh, this one is easy and achievable for everyone. Be the Honey Badger, be scrappy, hustle, don’t take no for an answer. Treat your team like VIPs and your clients like royalty. Measure what matters and don’t get distracted with shinny pennies and rabbit holes.
Are you active on social media professionally? If so, what platforms work best for engaging your followers?
I’m only on LinkedIn, it’s imperative for all business networking, connecting, prospecting and staying relevant in the B2B world.
Who was your biggest influencer?
I was blessed with so many influencers and angels. Ma is probably my biggest influencer since she raised me and did the best she could with what she had. A close second was with father, my Nonno Serafino and a close third, was her brother, Zio Gilberto. Both were hard-working Sicilians who loved their family and would do anything for them.
What is the most challenging part of your work as a Leader?
Inspiring my team(s) to be the best versions of themselves and take care of themselves.
What do you have your sights set on next?
Self-provisioning technology, scaling our firm and double downing on cyber and AI.
What is a day in your life like?
I’m up at 4:30, drink lots of water, mediate, catch up on email and lay out my day. A day out in the world could start with me being on-set with a client, later negotiating a deal for a new series with another client – working to double the comp plus get a producer’s credit. After a workout and lunch, I’m working on another project to close a multi-million dollar real estate deal and the day ends dealing with a celebrity in a lawsuit over a penthouse.. Most of my time is spent making deals, saving deals or being sure deals are carried through. I’m involved as an agent, attorney and sometimes a principal or investor in these deals. Current big deals I’m involved in are movies, TV shows, blockbuster book projects, complex real estate deals, and litigation.
Do you have any hobbies?
Family, people, growing companies.
What makes you smile?
When I can make other people smile. Being appreciated or even better, admired.
What are you never without?
Friends, stress and a nagging feeling that I can never just stop and rest.
What scares you?
Mediocrity.
What is your favorite vacation spot?
So hard, it really depends. I love warm weather and classic parts of Europe. If I had to pick one spot, it’s Cefalu near my family’s hometown in Sicily.
Other work, published articles, interviews or accomplishments:
- Podcast on Coruzant
- https://www.inc.com/author/ken-sterling
- https://www.forbes.com/sites/forbescommunicationscouncil/people/kensterling1/?sh=5a341ff7516b
- https://www.youtube.com/watch?v=MIhT1sKiWMw&themeRefresh=1
- 5 advanced degrees at facility based top ranked universities – all in 10 years
