Episode Summary
In this episode, Jake Knight sits down with David Newfield — strategic advisor, business coach, and founder of NextGenCoach — for a powerful conversation on identity, individuation, and redefining success as a rising gen. Drawing from his own family business experience and a diverse professional background that spans hospitality, real estate development, and mining, David now coaches next generation leaders looking to build meaningful careers on their own terms.
Whether you've stepped away from the family business, are navigating what’s next, or are seeking to turn generational pressure into personal power, this conversation is filled with clarity, honesty, and tools for forward momentum.
02:17 — David’s Path to Coaching
David recounts his journey through multiple industries including family hospitality ventures in the Caribbean, a $2B real estate development portfolio in Toronto, and a wild mining play in Peru before launching his coaching and consulting firm dedicated to rising gen leaders.
06:07 — Leaving the Family Business But Not Burning the Bridge
Not all exits need to be permanent. David shares why stepping away to gain skills and perspective can position rising gens for more meaningful re-entry or future partnership within the family enterprise.
08:14 — Rejecting the Narrative of Starting from Scratch
Too many next gens believe that forging their own path means erasing everything they've inherited.
11:00 — Confidence and Decision-Making
David introduces one of his core coaching philosophies: helping clients move from needing certainty to navigating with probability. The key to progress is building momentum through better and faster decision-making.
14:00 — Three Client Profiles
David outlines the three phases of client journeys he typically works with. The first is for those contemplating leaving the family business. The second is for those with an idea but overwhelmed by execution. The third is for those building within the family orbit but wanting autonomy and ownership.
19:28 — Identity, Comparison, and the Sibling Effect
Jake and David dive into the pressures of comparison within family systems — especially between siblings — and the internal battles of wanting to be known for your first name, not your last.
26:18 — Trade-Offs and Ownership
What does it really mean to build something of your own? David discusses the sacrifices and trade-offs rising gens must make, especially when tempted by the comfort and distractions of generational privilege.
30:31 — Communicating with Family Without Blowing It Up
Jake and David explore the emotional and strategic layers of high-stakes conversations within family systems and how rehearsal, role-playing, and coaching can lead to more productive and less reactive communication.
36:48 — Strategic Applications of AI in Business Building
David shares how his clients and his own firm use tools like ChatGPT and Claude to simulate communication, build strategies, and accelerate learning, especially during early-stage business planning.
39:14 — How the Industry Can Better Serve the Rising Gen
David offers actionable insights for advisors, law firms, and family offices who risk being left behind by the next generation. Supporting rising gens early and meaningfully is the only path to continued partnership.
44:50 — New KPIs for a New Generation
Jake and David discuss the industry’s need to evolve its metrics and mindset, especially as leadership ages and younger generations seek more personalized, human-centered support.
46:16 — Defining Success on Your Own Terms
David closes the episode by sharing his “four-legged table” framework for a balanced and fulfilling life. Professional achievement, family connection, physical and mental health, and spiritual grounding each play a role in how he defines and lives success.
Website: nextgencoach.com
LinkedIn: David Newfield
Email: David@nextgencoach.com
Visit joinenclave.com to learn more
