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Larry Jacobson
About
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Biography Highlights
- When it comes to overcoming tough challenges, rising to fearless leadership, and living a life filled with passion, Larry Jacobson hasn’t just been around the block. He’s been around the world.
Biography
Larry Jacobson Leadership Speaker and Adventurer
Larry Jacobson is a recognized thought leader in the realm of non-fiscal retirement lifestyle planning. His work draws from both his personal success and that of the many clients he has guided. Honored as “Retirement Coach of the Year” by the Retirement Coaches Association, he continues to shape the field. His latest book, What’s Your Encore? A Step-by-Step Guide to Retiring with Purpose and Fulfillment, reflects his commitment to helping others navigate retirement with clarity and meaning.
Successfully transitioning from CEO to global sailor, he fulfilled his longtime dream of circumnavigating the world—then seamlessly shifted from sailor to six-time award-winning author, coach, and two-time TEDx motivational speaker. His expertise spans Re-defining Retirement, Achieving Dreams, Peak Performance, Navigating Entrepreneurship, Living with Passion, Embracing Change, Finding Happiness, and Navigating Leadership.
A natural-born inspirational speaker, Larry refined his talent through training with leading experts in the speaking industry. As a Certified World Class Speaking Coach, he understands how to captivate an audience from start to finish. He is thoughtful, humorous, and known for delivering messages with lasting impact.
A California native, Larry Jacobson grew up along the shores of the Pacific Ocean. Holding degrees from the University of California Irvine and Berkeley, he cultivated both an entrepreneurial drive and an adventurous spirit. A circumnavigator and lifelong adventurer, Larry is an avid sailor with more than 50,000 blue-water miles to his name.
Award-winning Author of Five Books and Two Video Courses
He is the creator of Sail Into Retirement™, a self-guided video program that blends home study with personalized coaching to support a smooth transition from career to retirement.
He is widely recognized for his six-time award-winning memoir of his circumnavigation, The Boy Behind the Gate: How His Dream of Sailing Around the World Became a Six-Year Odyssey of Adventure, Fear, Discovery, and Love. He also authored the children’s edition of that story, Let’s Go!. Known for his entrepreneurial insight, he recently released Navigating Entrepreneurship in both book and online course formats. His newest publication, Beyond the Meeting Room: A Practical Guide to Mastering Communication in a Remote World, highlights his communication expertise. Larry is also in demand as a Certified World Class Speaking Coach.
Jacobson energizes audiences through vivid storytelling paired with compelling photos and videos, placing listeners in the middle of each adventure. He uses these moments to illuminate powerful insights on setting goals, persevering through adversity, achieving new milestones, and fulfilling long-held dreams—no matter how challenging or delayed. His dynamic recounting of his global journey serves as a guiding beacon for anyone striving for excellence in business or personal life.
Jacobson’s business experience, deep understanding of sales and marketing, and sharp sense of humor shine through in his keynote speeches. With high energy and enthusiasm, he shares his wisdom, wit, and charisma while drawing strong parallels that empower participants to apply his lessons to their own lives and careers.
In the realms of Leadership Development and Sales-Performance training, Larry Jacobson is the preferred speaker for many top organizations worldwide. His tailored keynotes and interactive training workshops are designed specifically around the goals and needs of each event.
Jacobson’s leadership insights come directly from lived experience. After a successful corporate career, he boldly stepped away from financial security and comfort to pursue his lifelong dream of sailing around the world. Over six years of circumnavigation, he gained invaluable, hard-won lessons: how to overcome fear and limitations, embrace change, endure inevitable storms on the path to success, and bring one’s dreams to life despite the odds.
Throughout that odyssey, Larry and his crew encountered countless challenges and discovered the true meaning of perseverance. They experienced why so few who attempt a global voyage ever complete it. From surviving the tsunami in Thailand to facing pirates in the Gulf of Aden, the six-year adventure presented extraordinary risks—any one capable of ending the journey. Instead, each challenge reaffirmed that passion fueled every step forward. It’s this same passion he inspires audiences to activate in their own lives.
A True Achiever with Outstanding Leadership Skills, and the Talent of Making His Stories Relevant to the Audience
Larry’s business path began when he founded an adventure travel company leading whitewater-rafting expeditions on previously uncharted rivers in New Zealand. He understands firsthand the challenges entrepreneurs face when building a company from the ground up.
From Salesman to Vice-President to President, to CEO – He Understands Business
- Larry began his career in incentive travel just as the industry entered a period of explosive growth.
- After five years working for another company, he founded World Class Incentives.
- As CEO, while actively leading sales and marketing, he elevated the company to a top-tier position in the incentive and meeting planning arena.
- Jacobson expertly evaluated client distribution systems and applied strategic, performance-enhancing incentives to boost sales, employee engagement, and dealer/distributor loyalty.
- World Class Incentives earned a reputation for producing exceptional events recognized industry-wide as setting the standard.
Redefining Retirement
Beyond his inspiring messages centered on pursuing dreams and rising above adversity, Larry is a leading voice in rethinking retirement. His books, video courses, and keynote presentations address key questions surrounding non-financial retirement planning. What becomes of your identity when your lifelong career ends? What will your encore be? How can you transition into a purposeful, fulfilling next chapter? Professionals, organizations, and financial planners alike benefit from the practical tools and insights he provides. His sessions often draw packed rooms and standing ovations—testament to the authority and authenticity he brings from lived experience.
Videos
Popular Talks
Make Passion Your Priority
From TEDx talks to corporate meetings, making passion your priority is now Larry Jacobsons single most requested speech. Larry opens his heart to tell the story of discovering his passion for sailing at the age of 13. Then he jumps right in to the lives of the audience and how important passion is for them, how to find it, and how it can improve the quality of their work and personal lives.
By getting to know you and your audience in advance, Larry then weaves his tale of passion into the work lives of the audience with great effectiveness using stories and slides from his 6 years of sailing around the world.
Humor, emotion, and passion are keys to delivering this keynote and Larry Jacobson has them all.
Navigating Leadership: Leadership Lessons Learned at Sea
As a leader in sales and marketing for twenty years, and then captaining his own boat around the world, Larry Jacobson speaks with unique authority and credibility. As a leader and adventurer, he weaves tales of his six-year odyssey circumnavigating the globe with the challenges of leadership in our fast-paced business world.
There are similarities in leading your crew while facing 30-foot walls of water slamming into your boat in a horrific Red Sea storm, and leading in your company. Its lonely, scary, and its easy to want to make it all go away. Making your dream of sailing around the world come true doesn’t happen by luck, but by good leadership and visualizing achievement.
Like sailing around the world, leadership in business is making decisions, taking risks, maintaining a good attitude, facing fears, staying focused, and digging deep for strength and perseverance.
This keynote is the perfect fit for any sales meeting, conference, association, or incentive program, your attendees will learn:
- How to feel comfortable taking risks
- The skills of recognizing fears and using them to their advantage while in a leadership role
- How to make decisions more promptly and effectively
- That without dreams, leaders have nowhere to lead to
- The importance of goal-setting as part of being a leader
- That tenacity is a skill best learned from practice
- That a leader has to lead all the way to the final conclusion.
As a true thought leader in the field of leadership, Jacobson’s credibility, wit, and eagerness for you to have a successful event, add up to a great keynote. He is a well seasoned speaker with over 20 years experience in the event industry. He’s a great leader for your event.
Living Your Unstoppable Life!
Very few people achieve the status of circumnavigator. In fact, many more people climb Mt. Everest each year. Yet Larry Jacobson decided as a 16-year-old boy that sailing around the world was what he wanted to do and he never let go of that dream.
There were many times before and during his challenging six-year odyssey that he could have quit and jumped ship, as so many do. But he didn’t.
Sailing around the world is only one of Larry’s achievements. Throughout his life, he has strived for and achieved great endeavors, both in his professional and personal life. He knows how to make dreams come true, no matter who or what gets in the way. It’s this quality of being unstoppable and refusing to settle for less than your best that makes the difference between mere existence and living the life of your dreams.
Upon returning from his six-year voyage, visiting 40 countries, sailing over 40,000 miles, and overcoming innumerable challenges, he turned his experience into an Amazon #1 seller, six-time award-winning book.
In this keynote, Larry inspires his audience to dream again, overcome obstacles that stand in the way of honoring their own dreams, and transform them into reality.
This keynote is a perfect fit for any general motivational type event including sales meetings, conferences, associations, and incentive programs. Your attendees will learn:
- How to awaken our dormant dreams and turn them into actionable goals
- How good things in our lives get in the way of great things
- Why staying focused on your dream is so critical
- How to see and mark the value in every day
- Five steps to start living Your Unstoppable Life and fill it with Love, Laughter and Passion
Join Larry for this inspiring, empowering and entertaining keynote that will have your audience remembering and recommitting to what’s really most important to them.
The 22-Minute Keynote
How much of your audience is still listening after 22 minutes? After giving two TEDx talks, Larry Jacobson is convinced that you should be able to say what you want within that time frame. By doing so, you’re guaranteed the audience is still listening and absorbing.
By carefully crafting each and every word, not beating around the bush, and making every sentence count, Larry believes he can accomplish the job in 22 minutes. TED talks are limited to 20 minutes, and Larry adds 10% in order to make his points with emphasis.
Of course you can ask Larry to give a 30-minute keynote, which he also believes works well for a limited time frame. And yes, he speaks for the typical 50-minute keynote as welland very effectively. However, when planning your event, consider the 22-30 minute option. It works.
Navigating Sales: Achieving Unstoppable Performance
What stops many salespeople isn’t lack of skill, education or talent. It’s fear.
Fear of making that next cold call or finally presenting that big prospect they’ve been chasing. Making that next sales call or trying to get an appointment with a big prospect can feel like facing a 30-foot wave in a storm lonely, scary, out of control.
Larry Jacobson knows all about that kind of fear and what it takes to turn it around and achieve the success of your dreams. After 20 years in the sales and marketing world, he spent six years circumnavigating the globe in a sailboat. As a sales expert and adventurer, Larry draws instructive and entertaining parallels between tales of his odyssey at sea and the challenges of selling in our fast-paced business world.
Sales is the driving force of every industry and the lifeblood of every business. Like sailing around the world, successful selling calls for decisiveness, a tolerance for risks, staying positive no matter what, maintaining a laser focus, and a strength and perseverance that come from digging deep inside.
Cultivating these skills is what allowed Larry Jacobson to close millions of dollars in business as well as to complete his circumnavigation fulfilling a childhood dream against all odds.
Larry understands what it takes to close sales in just about any industry, from high-tech to home products. But he also knows that success in sales, just like any endeavor in business or in life, isn’t about knowing tricks of the trade; its about committing to become the best at what you do.
Larry challenges each listener in his audience to do just that: Achieve Unstoppable Performance.
This keynote is the perfect fit for any sales meeting, conference, or incentive program. Your sales people will learn:
- How setting goals can increase their sales
- Why taking risks is necessary in sales
- Why fear is nothing to be afraid of
- How to keep a good attitude in spite of adversity
- How important perseverance is to their careers
- Why objections in sales are good
- How a “no” brings you one step closer to a “yes”
- What to do after making a sale
A true sales professional, Larry will inspire your sales team to greater heights.
Making Ideas Happen: Passion, Priorities, and Perseverance
Many people have ideas for their own personal growth and for new ways to accomplish more at their work. Sadly, many ideas never come to fruition because one or more of the following three characteristics are missing.
- Passion. No great idea ever happened without dedicated passion. Do you want your idea to happen more than the status quo?
- The idea must be made a priority of the originator. And they must make it a company priority. The company must then buy in to the idea. That will put more passion behind it in order to fuel its success.
- Most ideas never happen because the person or company doesn’t persevere.
Making an idea happen is not an event, but rather a process. Larry Jacobson had an idea when he was 13 years old that he would sail around the world. It took him 33 years of passion, prioritizing, and perseverance to make that dream come true. And it took an enormous amount of all three of these traits to spend six years sailing his own boat all the way around the world.
This as an area in which Larry Jacobson is indeed an expert, and was the standing ovation topic of Larry’s TEDx talk to a youth group. From 30 to 50 minutes, Larry uses stories, pictures, and makes the subject relevant to the lives of the audience. This talk is a winner!
Redefining Retirement, What's Your Encore?
Until now, nearly all retirement planning has been fiscal. Once your finances are in order, the question still remains: What will you do with your time in retirement? It’s a much bigger challenge than expected and very few sources address the problem.
Shortly after the euphoria of, “Yahoo! I don’t have to go to work today!” wears off, new retirees often feel:
- An overall sense of loss Loss of social interaction from fellow employees Lack of purpose
- Void of fulfillment
- No longer needed
- No longer appreciated for their knowledge
- Suffer from fears about not knowing their next step
- Disconnected from society
- Loss of direction
- Don’t know who to turn to for help with these new challenges they are facing
How do you redefine retirement so it provides you a continued life of fulfillment and purpose? How do you live a balanced life in retirement when you discover that golf and grandkids aren’t enough? As a thought leader in the field of non-financial retirement planning, Larry Jacobson addresses all of these issues and more.
A new study from the American Heart Association shows you have a 56% higher chance of stroke if you cant state your purpose in life during your retirement. Jacobson guides his audiences to find that purpose.
Baby Boomers are retiring at the rate of 10,000 per day for the next 15 years. They are living 10-30 years longer than their parents and are wondering what to do with their time. Its an unexpected part of life that has not been planned out for them.
Retirees without a plan have a 40% higher probability of falling into clinical depression than non-retirees. Still, only 30% of retirees have a clear plan of what they want in their retirement years and what steps to take in order to make that life a reality. Those with a plan have clarity of their purpose, passions, desires, and skills; and know step by step how to plan a fulfilling retirement. Larry’s audience members leave his presentation with concrete steps to creating their purposeful and joyful retirement plan.
Larry Jacobson Brings Your Audience a Rich Personal Experience After retirement from 20 years as a corporate executive, Larry achieved his own dream of sailing his own boat around the world. Jacobson now is dedicated to helping others redefine their retirement to live a longer and more fulfilled life with purpose. He guides his clients to find their true passion and merge it with their knowledge and wisdom to find a new purpose in life. Jacobson stands out as a work to retirement transition expert. His personal experience and stories of achievement, will engage your audience and provide practical application to their own lives.
Larry'S
Testimonials
E.G. Sebastian
Marketing Manager
Asheville, NC
Marcelle Epley
Senior VP
Long Beach Transit
Kristen Newcomer
Director of Events
Investments and Wealth Institute
Patricia Fripp
Past President
National Speaker Association
Jill Hoiffman
Mayor of Sausalito, CA
Theresa Davis
Chair
Case District VII Conference
Lindsay Olson
Event Planner
Calcom Association
Mike Hebel
Program Chairman
San Francisco Police Officers Association
Chuck Kuglen
Managing Partner / VP of Sales & Development
The Henderson Group
Books

What’s Your Encore: A Step-by-Step Guide to Retiring with Purpose and Fulfillment
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What’s Your Encore: A Step-by-Step Guide to Retiring with Purpose and Fulfillment

The Boy Behind the Gate: How His Dream of Sailing Around the World Became a Six-Year Odyssey of Adventure, Fear, Discovery, and Love
Read more..
The Boy Behind the Gate: How His Dream of Sailing Around the World Became a Six-Year Odyssey of Adventure, Fear, Discovery, and Love

Navigating Entrepreneurship: 11 Proven Keys to Success
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Navigating Entrepreneurship: 11 Proven Keys to Success

Let’s Go! Middle Grade Reader
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Let’s Go! Middle Grade Reader

Beyond the Meeting Room: A Practical Guide to Mastering Communication in a Remote World
Read more..