“Your Job Is To Ask The Right Questions” 5 Leadership Lessons With Jeremy Straub

Yitzi Weiner
May 14, 2018 · 5 min read

“As the CEO, you need to ask the questions that will help identify problems within your company. Then you need to decide the best way to spend its talent and resources on. Prioritizing is key.”

I had the pleasure to interview Jeremy Straub. Jeremy is the Founder and CEO of Coastal Wealth, a member of the MassMutual Financial Group. A financial industry thought leader who brings energy and passion to helping people preserve wealth, he quickly ascended to the top of the financial planning industry at other companies before establishing Coastal Wealth in 2016.

Yitzi: Thank you so much for doing this with us! What is your “backstory”?

Originally from Bethlehem, Pennsylvania, my entrepreneurial nature was influenced by my father, who worked his way up in the auto industry from selling cars to owning dealerships. He instilled in me early on the importance of helping others and so I was raised with the mind of a capitalist and the heart of a social worker.

Yitzi: Can you share the funniest or most interesting story that happened to you since you began leading your company?

The funniest thing that has happened since launching Coastal Wealth was being asked to be on Bravo’s Below Deck. Once the episode aired, it was funny to see how many C-level executives that work at Fortune 500 companies called to ask about the show. I had no idea how many of my successful colleagues were into reality shows as their guilty pleasure.

Yitzi: So how exactly does your company help people?

My goal was to create a firm with a family feel — where advisors are treated like clients, and clients have experts at their fingertips to address every aspect of their financial lives. Its mission is to help clients, businesses and their employees, prosper by making good financial decisions, and to avoid catastrophic ones. We achieve this through financial planning, asset protection, property and casualty insurance and group benefits.

Yitzi: What do you think makes your company stand out? Can you share a story?

At Coastal Wealth we put people before profit. We believe that to do well, we must do good — to our clients, employees, agents and community. It is part of our DNA to help and collectively our team donates in time, talent and dollars to 159 charities across South Florida. We also happen to be extremely successful at helping people and businesses make smart financial decisions.

Yitzi: None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are?

My grandfather was an inspiration to me. There was a childhood story he would tell about a panda and a coyote. When the panda can’t find bamboo to eat, they starve. However, if the coyote can’t find its food source of choice — it adapts to find another. The moral of the story was that you have to adapt to your changing environment to survive. I’ve always kept this lesson in mind and it has contributed to a lot of my success.

The Coastal Wealth team believes strongly in giving back and is highly engaged in the community, with 70 percent of employees involved with local charities contributing more than 2000 hours of community service per month to organizations serving diverse needs throughout Florida. Personally, I am a volunteer with SCORE in Broward County, where we help entrepreneurs start, develop, and grow their businesses.

Yitzi: What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why. (Please share a story or example for each.)

1. Protect your time. When you reach a certain level of success, your ability to say no is more important than your ability to say yes. People will want to sell you or make you change your mind. In addition, it is very easy to get caught up attending conferences or attending networking events. You have to be selective in how you spend your limited amount of time and drive your own agenda.

2. You never see the easy problems. Every issue that was an easy solve will get handled before it reaches your desk. You never get the simple things. It’s the difficult, emotionally charged, and risky tough decisions that you have to resolve.

3. Talent around you is your key to sanity. If you have talented people around you it will make your life easier. When you don’t have strong people, your workload will increase. So it is important to hire and develop talent. Also, to realize that someone who got you to the level you are today, may not be the best person to help you reach the next level.

4. Never lose sight of who drives your revenue. It is easy to start to believe your own press. So when people say you are so successful you tend to stop focusing in on what is important. You lose grasp of exactly what drives your revenue and their changing needs. Never forget the people, in our case our advisors and clients, you are running your business for.

5. Your job is to ask the right questions. As the CEO, you need to ask the questions that will help identify problems within your company. Then you need to decide the best way to spend its talent and resources on. Prioritizing is key.

Yitzi: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this :-)

I find people that are able to take a passion in a traditional area and make it something more exciting and their own, fascinating. Laird Hamilton was a pro surfer who wasn’t a fan of organized competition, which is the typical way people make money in surfing. He helped innovate offshoots of surfing such as big wave tow-in surfing, paddle boarding, and foil surfing. Along with innovating, he became a health “guru”, and developed new group training techniques and wrote articles on healthy living. But what truly makes Laird someone I would like to meet is his focus on his family. I believe he has shown real success: balanced life of health, family and living your passion. With my background in extreme sports, I am intrigued by other athletes, which led us to launch an athlete division at Coastal Wealth.

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