Larry Jacobson
Senior teams under sustained pressure do not fail from a single shock. They fail from accumulated fear, deferred decisions, and the quiet erosion of conviction over months of difficult conditions. Most leadership development addresses the crisis moment. Far less addresses the long stretch in between, when the temptation to retreat is constant and invisible.
Larry Jacobson is a motivational keynote speaker and author who draws on a six-year sailing circumnavigation to help leaders and teams hold their nerve, manage fear, and finish what they start.
Full Profile
Why organisations work with Larry Jacobson
- A source experience that is independently documented and book-published. The six-year voyage, the 40 countries, the tsunami in Thailand, the pirate threat in the Gulf of Aden are not rhetorical devices, they are a verifiable record audiences can read after the keynote.
- Direct translation between an extreme personal undertaking and the corporate context he left to begin it. Jacobson ran a company before he sailed, and speaks to commercial audiences with the cadence of someone who has carried a P&L.
- A specific argument that fear is a workable variable, not a problem to be removed. Audiences leave with a clearer sense of how to act while still afraid, rather than waiting for the fear to subside.
- A track record with mainstream corporate and financial-services audiences, including Northwestern Mutual, Investment & Wealth Institute, and Retirement Coaches Association, alongside two TEDx platforms.
Biography highlights
- Six-year circumnavigation by sailboat, 40,000+ nautical miles, 40 countries visited.
- Author of The Boy Behind the Gate, an Amazon best-seller and award-winning memoir of the voyage.
- Two-time TEDx speaker: TEDx Golden Gate (“Passion Trumps Fear”) and TEDx Youth (“Passion, Priorities, and Perseverance”).
- Additional books include What’s Your Encore? A Step-by-Step Guide to Retiring with Purpose and Fulfillment, Beyond the Meeting Room: A Practical Guide to Mastering Communication in a Remote World, and Navigating Entrepreneurship: 11 Proven Keys to Success, with companion video programmes (Sail Into Retirement, Navigating Entrepreneurship) hosted at Buoy Training.
- Certified World Class Speaking Coach, the credential awarded through the 12-week certification programme run by 1999 World Champion of Public Speaking Craig Valentine.
- Keynote and coaching clients include Northwestern Mutual, Investment & Wealth Institute, Retirement Coaches Association, InVision, The Henderson Group, Hill Physicians, CASE District VII.
Biography
Most leadership content is written for the crisis. The harder problem is the long stretch in between, when conditions stay difficult, fear becomes ambient, and the easy decision is to retreat or wait. Jacobson’s material is built for that stretch.
He spent six years sailing around the world after running World Class Incentives, a corporate incentive and meeting planning business. The voyage covered 40,000 nautical miles and 40 countries, and included the 2004 Indian Ocean tsunami and a transit through the Gulf of Aden during a live piracy threat. The book that followed, The Boy Behind the Gate, became an Amazon best-seller and the spine of his speaking practice.
The argument he builds from that experience is practical. Fear is a workable variable in any sustained undertaking, not an obstacle to be removed before starting. Audiences hear how to make decisions while afraid, how to sustain conviction over months rather than minutes, and how to finish a long commitment that no one else can see the end of.
He has spoken twice on the TEDx platform and works regularly with corporate, financial-services, and association audiences, including Northwestern Mutual, Investment & Wealth Institute, and the Retirement Coaches Association. His retirement work extends beyond the keynote into What’s Your Encore?, a step-by-step retirement guide, and Sail Into Retirement, the structured video programme advisers use with clients. His other books include Beyond the Meeting Room on remote-world communication and Navigating Entrepreneurship. He is a Certified World Class Speaking Coach, a credential earned through the programme run by 1999 World Champion of Public Speaking Craig Valentine.
Key speaking topics
- Resilience and decision-making under sustained pressure
- Fear management in leadership
- Perseverance through long commitments
- Personal reinvention and career transition
- Goal-setting and execution
- Retirement and second-career planning
- Communication and presentation skills for senior audiences
Ideal for
- Sales kick-offs and annual corporate off-sites where the brief is morale and conviction, not analytical content
- Financial-services and wealth-management association audiences working on client retirement and life-stage conversations
- Leadership teams entering a long restructuring or turnaround, where the work will outlast the initial mandate
Audience outcomes
- A direct, named framework for acting while afraid, rather than waiting for confidence to arrive first.
- A clearer view of what sustains conviction over months of difficult conditions, drawn from a six-year first-person example.
- Permission to take a personally difficult decision they have been deferring, supported by a specific story rather than abstract encouragement.
Talks
Jacobson’s TEDx Golden Gate keynote and his most-requested corporate talk, arguing that fear is workable rather than disqualifying.
Key takeaways:
- A working definition of fear as a signal to plan, not a signal to stop.
- A first-person account of the decisions that made the six-year voyage possible, and the ones that nearly ended it.
- A direct ask of the audience: name the decision they are deferring and the fear underneath it.
Leadership keynote translating six years at sea into the corporate context Jacobson left to begin the voyage.
Key takeaways:
- How to lead a small team through a long undertaking when no one else can see the destination.
- The role of preparation in reducing the cost of unavoidable surprises.
- Specific examples of decisions under sustained pressure, including the Gulf of Aden transit.
Keynote for financial-services and wealth-management audiences working with clients on the non-financial side of retirement.
Key takeaways:
- Why the financial plan is the easier half of the retirement conversation.
- A structure for the “encore” question that advisers can use with clients.
- Examples drawn from Jacobson’s own transition out of corporate life.
Videos
Testimonials
Books
Fees
| EUR | GBP | USD | |
|---|---|---|---|
| Home Country | Under €12000 | Under £10,000 | Under $15000 |
| Asia Pacific | €12000 to €40000 | £10,001 - £35,000 | $15000 - $50000 |
| Europe | €12000 to €40000 | £10,001 - £35,000 | $15000 - $50000 |
| Middle East & Africa | €12000 to €40000 | £10,001 - £35,000 | $15000 - $50000 |
| South America | €12000 to €40000 | £10,001 - £35,000 | $15000 - $50000 |
| United Kingdom | €12000 to €40000 | £10,001 - £35,000 | $15000 - $50000 |
| US East Coast | Under €12000 | Under £10,000 | Under $15000 |
| US West Coast | Under €12000 | Under £10,000 | Under $15000 |
| Virtual | Under €12000 | Under £10,000 | Under $15000 |