We’re excited to introduce you to the always interesting and insightful Isaac Gordon. We hope you’ll enjoy our conversation with Isaac below.
Isaac, thanks for joining us, excited to have you contributing your stories and insights. We’d love to hear how you think where to draw the line in terms of asking friends and family to support your business – what’s okay and what’s over the line?
Speaking from my experiences alone I don’t think you can expect the world. And, that’s OK. Not everyone is going to see things how you see them! You get entrenched in the life you live and then subsequently surround yourself with people who are similar. That’s not reality though. That’s the bubble you’ve created to survive. When you step out of that bubble and back into the real world with family, friends. These are folks who have never left home, who have worked the same job with the same company for 30 years. That’s definitely not a knock. That is life and what we are taught. So, while you can expect them to cheer you on and hope for the best. You can’t truly expect them to understand. Is that tough? I can be! People you love and respect might believe you have gone insane. You might have to fight off the fears they possess and try to put on you. You might have to disconnect all together. But, yeah… that’s where you have to take a step back and have empathy towards their perspectives while not letting it drain you. Much easier said than done.
Where do I draw the line? I personally would never ask my family for seed money or a loan. Would I take a gift? Maybe! I think we’ve all heard the stories of so and so who got a loan from his uncle and turned it into a million dollar company. Not sure I want to ever go down that path. I’d rather get things popping on my own, grow and then support my family, if given the choice/chance.

Isaac, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
My name is Isaac and I run a company called New Legacy Enterprises (NLE). We are based in North Hollywood, CA and we specialize in all things entertainment but our main services include talent management, distribution, marketing, pr, talent buying, event planning and production, tour routing, consultations and talent booking. Later this year our booking agency, Breakpoint Booking, will add public speaking clients to its roster of talent. Speakers such as Ella Halikas, Iskra Lawrence and Juliette Brisman “A Heart Returned,” look to be early signees along with leadership expert and former United States Air Force F-15E Fighter Pilot Brandon Williams. The company also represents comedy and music clients.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.
I think you can absolutely say that this happened. I just couldn’t leave the music alone. I worked in radio for a decade. I started out working at WCOJ in West Chester, PA right out of college. From there I bounced around a bit working in production, sales, traffic and continuity. However, on the side I was an aspiring band manager! I wrote a blog, I booked shows, events, helped with music distribution. This was back in 2009, 2010. I’d work my day jobs at Delmarva Broadcasting Company (DBC), Fox 29 and Comcast and then I’d come home and go full music business mode. This was life up until around 2012 when I was pretty sure I wanted to switch careers. My passion for radio had dwindled by that time.
Key milestones? Anyone saying yes to me managing them! I think just the fact that I had people believe in me, see something in me and trust me enough to let me help them. That gave me the confidence to keep going. Shout Out The Quelle Source and Ben Runyan out of Philadelphia.
Have you ever had to pivot?
Yeah so after I graduated Full Sail my now husband and I moved to NYC and I left radio and TV behind to get a part time job and intern. I went from salary to hourly and with the internship it was unpaid. I actually ended up landing two internships which took up a lot of time. The NYC experience was a time to be alive though. I thoroughly enjoyed myself in NYC.. maybe a little too much. Not to say it wasn’t challenging. I remember running an errand and I was told to get a specific bottle of tequila over to a certain actor’s house by a certain time. Imagine not really understanding the subway system, it’s hot, the trains are late lol. Seeing people arrive 30 seconds late to an interview… sweating, probably with a legit reason but being turned around saying they weren’t getting the interview anymore. NYC was a beast but it was necessary.
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