Gary Sinderbrand

Gary Sinderbrand Speaking Topics

• Dial-for-Dollars to AI-Powered Connections: How Anyone Can Use AI to Solve Real Problems

  After training 12,000+ financial advisors at Merrill Lynch, UBS, and Morgan Stanley, Gary Sinderbrand watched a brutal pattern repeat: 80% of new advisors fail because cold outreach to strangers is a broken system. Instead of accepting this, Sinderbrand asked a different question: What if AI could identify who they SHOULD be talking to—people psychologically wired to connect with them?

  That question led Sinderbrand to build The Rainmaker App, combining Jungian psychological archetypes with AI to transform prospecting from a numbers game into a matching system. Response rates jumped from 2–3% to 25–40%.

  But here’s what audiences really take away: You don’t need to be a programmer to build AI solutions. You need a real problem, the courage to ask better questions, and the willingness to learn in public.

  Attendee Results:

  • Learn the 5-step framework for identifying problems AI can actually solve (not everything needs AI—most things don’t)
  • Understand how to translate domain expertise into AI-powered innovation without writing code
  • Discover how psychological intelligence and pattern recognition can transform relationship-based businesses
  • Walk away with practical tools to evaluate AI opportunities in their own industry
  • Hear the unfiltered story of what actually works (and what failed spectacularly) when a non-technical founder builds AI products

• The Reinvention Imperative: Why Your Fifth Act Might Be Your Best

  At 25, Gary Sinderbrand was a financial advisor. At 57, Sinderbrand pivoted to biotech, developing machine learning systems to optimize chronic disease treatments (US Patent #9,202,066). At 63, Sinderbrand returned to financial services as a consultant and coach. Now Sinderbrand is launching an AI startup that could revolutionize professional prospecting.

  Most people think reinvention is for the young. They’re wrong.

  Sinderbrand’s decades of pattern recognition, battle scars, network, and understanding of how humans actually make decisions—these aren’t relics of the past. They’re unfair advantages waiting to be deployed.

  Through hosting the podcast, “If The Public Only Knew” and interviewing entrepreneurs who’ve navigated their own reinventions—from CEOs who rebuilt after overdoses to founders who sold companies to Coca-Cola then bought them back—Sinderbrand discovered the common thread: his breaking point was his breakthrough waiting to happen.

  Attendee Results:

  • Understand why experience compounds rather than expires—and how to leverage accumulated wisdom
  • Learn the psychological barriers that keep accomplished professionals stuck (and how to break through)
  • Discover the 3 questions that reveal whether it’s time for evolution or revolution in their career
  • Hear real stories of entrepreneurs who transformed their deepest struggles into their greatest innovations
  • Walk away with a framework for evaluating whether their “crazy idea” is actually their calling

• Psychological Intelligence: The Missing Layer in AI and Sales

  Everyone's talking about AI transforming sales—better leads, more data, faster outreach. But they're missing the fundamental question: Why do certain advisor-client pairs thrive while others fail, even when the credentials match perfectly?

  The answer isn't in the data. It's in the psychology.

  After four decades studying why some financial advisors build million-dollar practices while equally talented peers struggle, Gary Sinderbrand discovered that WHO you pursue matters infinitely more than HOW MANY you contact. This insight—combined with Jungian personality archetypes and AI—became a patent-pending system with 132 claims that's catching Fortune 500 attention.

  This talk explores the intersection of psychology and technology that most AI conversations completely miss. Whether you're in financial services, real estate, executive search, or any relationship-driven business, understanding psychological compatibility isn't soft skills—it's your competitive moat.

  Attendee Results:

  • Learn why response rates vary from 2% to 40%—and it has nothing to do with your pitch
  • Understand how Jungian archetypes predict business relationship success (backed by data, not theory)
  • Discover the "compatibility stack" that determines whether a prospect will trust you before you ever speak
  • Walk away with immediately applicable insights for improving client retention and referral rates
  • Explore how psychological intelligence will reshape CRM, marketing automation, and sales enablement

• Behind Every Success: What 50+ Entrepreneur Interviews Taught Me About Failure

  Hosting “If The Public Only Knew” put Gary Sinderbrand across the table from CEOs who overcame addiction, founders who lost everything and rebuilt, and executives who walked away from eight-figure contracts because something felt wrong.

  What Sinderbrand discovered shattered his assumptions.

  These weren't superhuman risk-takers. They were people who hit walls, faced their limitations, and found that their wounds became their wisdom. Kerry Siggins went from overdose to leading an employee-owned construction empire. Nick Jonsson transformed C-suite loneliness into a global coaching movement. Ari Rastegar lost everything, then built across 38 cities in 13 states.

  The pattern? Conventional wisdom said “stop,” but something deeper said “continue differently.”

  This talk shares the five principles that emerged from 50+ conversations with founders who turned breaking points into breakthroughs—principles that challenged how Sinderbrand is building his own AI company and will challenge how attendees approach their biggest obstacles.

  Attendee Results:

  • Hear the unfiltered stories behind public success that most entrepreneurs never share
  • Learn the 5 patterns that separate those who break through from those who just break
  • Understand why “your wound becomes your wisdom” isn’t motivational fluff—it’s strategic reality
  • Discover how accomplished leaders handle isolation, uncertainty, and the impostor syndrome that never fully disappears
  • Walk away with a new framework for evaluating which constraints to fight and which to embrace

• The Experience Gap: Navigating the Great Wealth Management Knowledge Transfer

  This presentation will target Leadership and Financial Advisors at Wealth Management Firms: "The wealth management industry faces an unprecedented transition as a generation of seasoned advisors approaches retirement. While these veteran advisors have accumulated decades of market cycle experience, client relationship expertise, and nuanced portfolio management skills, their designated successors often lack the depth of training and practical experience that historically defined the profession. This "wisdom" gap threatens client service quality and portfolio management consistency at a time when market complexity and client needs are increasing. The industry must address how to effectively transfer not just client books, but the crucial experiential wisdom that has been the cornerstone of successful wealth management relationships."