Larry Jacobson

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Larry Jacobson Speaker Biography Larry Jacobson is a recognized thought leader in the field of non-fiscal retirement lifestyle planning. His work is based on his own successful experience and that of his clients. Successfully transitioning from CEO to sailor, he achieved his dream of sailing around the world, then from sailor to six-time award-winning author, coach, and two-time TEDx motivational speaker. His speaking areas of focus are Retirement, Achievement, Performance, Entrepreneurship, Passion, Embracing Change, Happiness, and Leadership. A California native, circumnavigator and adventurer, Larry Jacobson is an avid sailor with over 50,000 blue water miles under his keel. He is the creator of Sail Into Retirement™, a self-guided video program, which combines home study and personal coaching to ease the transition from work to retirement. He is author of the six-time award-winning memoir of his six-year circumnavigation, The Boy Behind the Gate, and his latest work is the children’s version of that journey, Let’s Go! He also recently published Navigating Entrepreneurship, soon to be a video program. While speaking comes naturally to him, to solidify his skills Larry was trained by the best coaches in the field. He customizes every speech and makes his stories relevant to the audience. In the last decade, he has presented to corporate clients, associations, youth organizations, and boards of directors. The feedback from participants is always 5-stars with comments of, “Inspiring, Funny, and Relevant.” He knows how to deliver your message with gusto. Larry lives in the San Francisco Bay Area and welcomes new friends and inquiries at:

Larry Jacobson's Experiences

Virtual In-Person
Virtual In-Person

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Circumnavigator Larry Jacobson

Larry's life adventures include a six-year circumnavigation in his own boat.

On Camera

Jacobson has years of experience on stage and on camera

Professional Captain

Jacobson holds his USCG Master Mariner's License for 100-ton yachts

  • What is your favorite quote? The difference between knowledge and wisdom: Knowledge is knowing a tomato is a fruit. Wisdom is knowing not to put it in a fruit salad.
  • Are there any moments that stand out as having a significant impact on your career? After 20 years in the corporate world, I sold my company, bought a boat, and left to circumnavigate. I left every bit of my comfort zone behind: Career, Income, Security, Home, and Identity t
  • Outside of your profession do you have any hobbies/interests? Sailing, Qi Gong, Yoga, Swimming, Travel, Helping others achieve their dreams.
  • Who do you look up to as a mentor and why? The wisest person I ever met was my mother. I live by her words every day and her most famous line was: "Accept or Reject. Don't tolerate."
  • Is there anything else we should know about you? I am a circumnavigator and wrote a best selling memoir about the six-year journey. The Boy Behind the Gate has own six literary awards and retains a 5-star rating on Amazon. I am passionate a