Interested in starting your own entrepreneurial journey in personal development but unsure what to expect? Then read up on our interview with Larry Jacobson, Founder of Buoy Coaching, located in Emeryville, CA, USA.

What's your business, and who are your customers?

The number one question asked by retirement planners is, "Do you have the money to retire?" The second most important question that is rarely asked is, "What are you going to do with your time in retirement?" I am one of the early thought leaders on the topic of Non-financial Retirement Coaching. I started with higher-priced coaching of CEO's, and have since produced a self-guided online video course that brings my coaching to nearly everyone at an affordable price.

My clients tend to come from higher positions in work careers such as VP, Presidents, and C-suite executives because it seems the more important a role in your career, the more difficult it is to retire and let go of that identity. However, everyone who retires will eventually ask themselves, "Is this all there is?" and "Where/how do I find purpose and fulfillment without my work career?" With 10,000 people reaching the age of 65 every day in the U.S. alone, there is a great need for non-financial retirement coaching, and I'm proud to be a thought leader and help guide the field.

Tell us about yourself

I was born into a happy lower-middle-class family where I watched and learned a strong work ethic from my father. He was creative, smart, and a hard worker, and it paid off when he invented and patented several products, which booted us up the ladder to the middle class. I learned at an early age that entrepreneurship, while difficult, was the way I could direct my own life. I eventually ended up in the Incentive Travel and Meeting Planning Industry as a salesman for another company. After five years of working for an abusive alcoholic, I left the company and, with a partner, started our own company, of which I became CEO.

After 15 years, we had established ourselves as the "Darling of the Industry" and sold our company. I made just enough money on the sale to think I could retire (I was wrong). I bought a 50' sailboat, left everything behind, and spent the next six years sailing around the world. Yes, it turns out the world is indeed round. This was a huge endeavor, and the difficulty in getting a boat all the way around the world is almost beyond description. The challenges come from weather, breakdowns, crew and personality issues, money, perseverance, and commitment.

When I returned from my journey, a friend who was the CEO of another company asked me for some advice. His question wasn't about how to run his company but rather about how I was able to leave my identity behind and become a sailor. So I took the next year to reverse-engineer and document how I did it, including my thoughts, feelings, and actions. That's when I identified the nine areas of focus in my course, SAIL INTO RETIREMENT. To this day, it remains the gold standard in non-financial retirement planning.

I want everyone to have access to a course in order to have a retirement that provides purpose and fulfillment and doesn't waste a retiree's time. The success emails I get from clients keep me motivated.

What's your biggest accomplishment as a business owner?

As a business owner, I've always believed in listening to what the client wants and translating that to what they need. I studied education in graduate school at UC Berkeley and understand how to build a course that teaches the desired result by building step upon step until it all comes together at the end. In SAIL INTO RETIREMENT, someone can start with no idea what their retirement will look like and end with a Plan of Action and knowing their next step to take.

I then listened to my clients and heard so many questions about being an entrepreneur and how to deal with the roller coaster ride of entrepreneurship; I created another online video training course NAVIGATING ENTREPRENEURSHIP. It teaches about the leadership of oneself and others and addresses the ups and downs of the entrepreneur lifestyle. And while the course reflects my decades of entrepreneurial experience, I keep it priced less than the cost of lunch to provide access to as many as possible. It's my way of giving back to the entrepreneurial community.

I would say a big accomplishment is in learning how to re-invent myself multiple times to reflect on what the community wants and needs. I have learned how to accept and embrace both fear and change, and my courses teach those skills. Passing on my wisdom is my ultimate goal.

What's one of the hardest things that come with being a business owner?

One of the most difficult ideas to grasp as a business owner is how to manage fear. Many entrepreneurs experience fear about so many things, such as quitting their jobs and comfort zone to start their own business, thinking they don't know enough to do so, analyzing risks, making decisions, and what to do when change is necessary.

Once you understand how to manage fear, it will change your life. My first TEDx talk was called "Passion Trumps Fear," and there, I taught the listener the easy two-step system to deal with fear. It works, and some people call me a "Fear Specialist." I was fairly fearless in business but truly learned the art of managing fear on my six-year sailing journey around the world. Thirty-foot seas, being chased by real pirates, and being cornered by Komodo Dragons will force you to learn how to deal with your fears very quickly.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Learn to manage your fears. I also teach it in my course, NAVIGATING ENTREPRENEURSHIP, which is now available for a ridiculously low price at
  2. No risk, no reward. If you're not willing to take a risk and leave your comfort zone, then you may as well resign yourself to continue doing what you are doing.
  3. Take action. If you don't make a decision to take action, then you just make a decision not to take action. "Neither words nor worry affects outcome; only action does." -- an original by Larry Jacobson. If you want something to happen, you have to be the one to take action. Make a plan because, at least with a plan, you have something to change.

Is there anything else you'd like to share?

I speak, write, and coach in order to share my knowledge and wisdom. My first book, THE BOY BEHIND THE GATE, is the story of my six-year sailing trip around the world. It won six literary awards and was an Amazon #1 seller. I think the reason it is successful is it inspires the reader to take action. I get many emails from readers from all over the world thanking me for inspiring them to do what they knew they wanted to do but just didn't have the courage. Then they read that I did it, so why couldn't they? The book is available on hardcover, Kindle, and Audible with me narrating. Then I wrote a middle-grade children's book about the same journey but for 8-12 years olds and it teaches good values and morals.

My two video courses are really effective at giving the listener the skills and traits they need to succeed. Both SAIL INTO RETIREMENT and NAVIGATING ENTREPRENEURSHIP are available on my training site directly at One can begin at my website, and there are links there to take you to the training, to purchase books, and there are LOTS of free gifts on my home page at from Leadership Tips to Public Speaking Tips. I'm currently working on two new books--ask me again in a year. :)

Where can people find you and your business?


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