Financial Advisor Success Podcast Ep 429

What It Takes To Really Help High Net Worth Business Owners Navigate Their Wealth With Purpose

Guest: Ali Nasser | Host: Michael Kitces | Date: March 18, 2025

Episode Overview

This episode explores how financial advisors can truly serve high net worth (HNW) business owners by integrating their entrepreneurial mindset and complex needs into comprehensive wealth planning—beyond what traditional financial planning curriculums teach. Ali Nasser, founder of the Wealth Integration System for Entrepreneurs (WISE), shares the evolution of his own advisory business into a consulting and coaching practice, revealing the systems and philosophies necessary to help business owners effectively navigate wealth, risk, and purpose.

Key Topics & Insights

1. The Unique Psychology and Planning Needs of HNW Business Owners

• Main Point: The risks and emotional dynamics of a concentrated business asset differ radically from holding a similar-sized stock position (e.g., $50M in own business vs $50M in Apple stock).

  • Quote: “If you meet someone that's got $50 million invested in Apple, what's the first thing you think — ‘How have you not diversified?’... But if it's $50 million in their own company, it’s, ‘What an amazing company, tell me more!’” (05:22)
  • Timestamp: 05:22–07:44

• Ali’s Philosophy: Advisors must approach business ownership with deep empathy and recognition of both control and legacy dimensions, not simply as a technical diversification problem.

  • Quote: “It’s not just a financial tool. It represents life’s work. Approaching it with empathy... is required. Otherwise, we won’t make progress.” (08:39)
  • Timestamp: 08:39–10:48

2. Rethinking Diversification for Entrepreneurs

• Key Insight: Diversification isn’t always the “right” answer—context matters.
  • For younger owners, reinvesting in business may make sense; for those nearer retirement or with larger net worth, building independent wealth outside the business becomes critical.
  • Quote: “I can practically guarantee you if you go in there and say you need to diversify, you're going to alienate the client. Instead, give them a path to clarity.” (11:31)
  • Timestamp: 11:31–12:41

3. Planning for “Independent Wealth” — Not Just a Liquidity Event

• Strategy: Mapping out regular cash extraction or personal savings from the business is as important as planning for a sale or partial exit.
  • Quote: “The more traditional business owner...it's independent wealth by saving maybe 20% of free cash flows for the next 15 years... So when you actually do exit, all your base is covered.” (15:07)
  • Timestamp: 15:07–18:47

4. The Evolution of Ali’s Practice: From Generalist to Hyper-Niche Entrepreneur Focus

• Ali’s Journey: Started as a generalist, charged fees for planning early, and then deliberately narrowed the firm to serve only entrepreneurs, which both amplified growth and personal fulfillment.
  • Quote: “The narrower the focus, the greater the opportunity... I picked the client segment that was the hardest, but I had the greatest passion for.” (19:10)
  • Timestamp: 19:10–24:52

5. Identifying “Planning Gaps” and Creating Value

• Value Proposition: Even sophisticated owners with teams of advisors have major, often invisible, gaps due to siloed advice—especially around integrations (e.g., charitable giving, entity structure, estate planning).

  • Quote: “When I'd pull all those plans together, I noticed major planning gaps... Nobody pulling all the pieces together.” (29:50)
  • Timestamp: 29:50–33:24

• Example Gaps:

  • Not donating appreciated assets to charity (missing tax benefits)
  • Will/estate plans in conflict with asset titling
  • Uncoordinated distribution strategies
  • Timestamp: 33:24–36:24

6. Multi-Stage, Fee-Based Planning Process (“Wealth With Purpose”)

• Process: Comprehensive, iterative planning done over 6–9 months, typically 8 meetings, with deep integration of the business owner’s entire financial, tax, legal, and family picture.

  • Quote: “Eight meetings over six to nine months for mapping a path to what he calls independent wealth for his entrepreneur clients.” (49:24)
  • Timestamp: 49:24–50:05

• Engagement Model: Substantial up-front and ongoing consulting fees ($10k–$100k first year, $5k–$15k ongoing), justified through demonstrated, ROI-rich value creation.

  • Timestamp: 62:41–63:20

7. Coaching Through “Paradigm Gaps” & Mindset Issues

• Common Entrepreneur Paradigms:
  • Skepticism of markets, bias toward their own business (rooted in past investment losses)
  • Feelings of scarcity and financial trauma, even after substantial success
  • Quote: “Most entrepreneurs have a paradigm that...their money experience was traumatic or had high adversity. They’ve been running toward wealth to protect themselves against fear of scarcity.” (56:25)
  • Notable Education Tool: Reframing index investing as “diversified entrepreneurship.”
  • Timestamp: 50:05–59:07

8. Transitioning from Advisor to Coaching and Educator

• Ali’s Shift: Sold his firm to focus on WISE—a platform to train advisors via bootcamps and directly coach entrepreneurs, separate from investment management and advice.

  • Quote: “Do I want to be the CEO of a wealth management firm and also an education company? ... I picked the path to build [the] education and coaching company.” (65:15)
  • Timestamp: 65:15–68:34

• Current Offerings: Advisor bootcamps (2.5 days intensive + ongoing coaching, $15k–$25k), entrepreneur workshops, and cross-referrals between educated business owners and WISE-trained advisors.

  • Timestamp: 68:54–75:49

9. Entrepreneurship Lessons: Scaling, Delegation, and Standards

• Challenges:

  • Maintaining client experience as business scales and as others deliver the process.
  • Letting go of team members who aren’t a great fit is “the hardest part.”
  • Quote: “You've got to be crystal clear with your vision ...and when there’s someone on the team that isn’t meeting that standard, getting rid of them. And that's the hardest part for me.” (78:13)
  • Timestamp: 75:49–83:00

• Top Learning: Feedback from “avatar” clients (those you most want to replicate) is more instructive than from squeaky wheels or internal sources—use that to continuously improve and focus.

  • Timestamp: 83:06–86:00

10. Advice for Advisors & Defining Success

• Advice for New Advisors:

  • Get a mentor, invest in professional development, avoid learning everything “the hard way.”
  • Quote: “There are many people...that have made our mistakes over the years and that love helping [you]...Don't learn it the hard way.” (86:06)
  • Timestamp: 86:06–87:07

• Ali’s Definition of Success:

  • Achievement of goals, but also enjoyment of the journey.
  • Focus on both “return on life experience” and return on investment.
  • Quote: “So often we're so consumed with getting to the outcome...that we don’t actually enjoy the journey and we’re missing out on life.” (87:37)
  • Timestamp: 87:37–89:05

Notable Quotes & Memorable Moments

• “It’s not just money. It’s not just a financial tool. It represents life's work.” — Ali Nasser (08:39)
• “The gems are in the details of the process that's really needed to serve entrepreneur clients and their needs effectively.” — Ali Nasser (Intro, 02:27)
• “There’s nothing more dangerous than a bored entrepreneur, except a bored entrepreneur with a lot of cash.” — Michael Kitces (63:43)
• “If you empower and educate...there's a 90% chance that owner’s going to go, I’ll give this person a second meeting.” — Ali Nasser (39:12)
• “Pick your best clients...they represent your avatar. They're your number one source of innovation and growth.” — Ali Nasser (83:06)

Important Segments & Timestamps

| Segment | Timestamp | |---------------------------------------------------|-------------| | Business owners vs investment clients psychology | 05:22–10:48 | | Strategies for building independent wealth | 15:07–18:47 | | Niching to entrepreneurs: the big decision | 19:10–24:52 | | Finding planning gaps, showing value | 29:50–36:24 | | Process: 8 meetings over 6–9 months | 49:24–50:05 | | Overcoming entrepreneur mindset “paradigm gaps” | 50:05–59:07 | | Transition to education/coaching business | 65:15–68:34 | | Advisor training bootcamps: structure & pricing | 71:27–75:49 | | Team, delegation, and client experience lessons | 75:49–83:00 | | “Avatar” client feedback for growth | 83:06–86:00 | | Advice for new advisors, Ali’s definition of success | 86:06–89:05 |

Final Thoughts

This episode offers a unique behind-the-scenes look at what it really takes to help successful entrepreneurs and business owners achieve holistic wealth and life satisfaction. Ali Nasser doesn’t just share technical strategies—he illuminates the mindset, empathy, and business model pivots required for advisors to have genuine impact. Whether you’re looking to niche your advisory practice, develop deeper client relationships, or explore training in the WISE process, this episode is a comprehensive resource.

For further details and resources, including a link to Ali’s book The Business Owner’s Dilemma, visit kitces.com/429.