Becker Business Podcast: "Howard Klieger on Building True Wealth Through Planning and Behavior" (12-1-25)
Host: Scott Becker
Guest: Howard Klieger, Founder, Walled Lake Planning
Release Date: December 1, 2025

Episode Overview

In this insightful episode, Scott Becker interviews Howard Klieger, veteran wealth manager and founder of Walled Lake Planning. The conversation delves deep into the philosophy of wealth planning, moving beyond returns to comprehensive financial well-being. Topics include the importance of behavioral finance, building client trust, effective portfolio planning, the role of communication within families, and current market concerns. Klieger’s wisdom is augmented by decades of experience and delivered in a candid, relatable manner.

Key Discussion Points & Insights

1. Howard Klieger’s Journey & Epiphany in Wealth Planning

[00:34–03:48]

• Background: Klieger discusses his 45-year foundational career in conservative wealth management, prioritizing clients’ “serious money” and evolving from pure asset management to comprehensive financial planning.
• Founding Moment: A pivotal encounter with a client (brought in by partner Noel Cooper) led to the realization that genuine client service must dig deeper than surface-level portfolio management.
• Quote:

  "That was the day I changed my asset management firm to a planning group... we don't ask 10 questions, we ask 110 questions. And that's how we get to do what we do."
  — Howard Klieger [03:36]

2. Sales Lessons & the Value of Going Deeper

[03:48-06:49]

• Beyond the Sale: Klieger highlights the tendency in many industries to disengage after “the sale,” contrasting that with the superior client outcomes achieved by digging into clients' real needs post-sale.
• Analogy: The approach is likened to excellent doctors and lawyers—those who seek to truly understand their clients.
• Quote:

  "We're so well trained to sell and not quote, unquote, 'sell through the close.' But really, you have to help clients understand sometimes what their real need is. Not convince them what their need is, but help them find what their real need is."
  — Howard Klieger [05:40]

3. The Name "Walled Lake": Purpose, Meaning, and Client Comfort

[07:16–09:03]

• Genesis of the Name: Inspired by partner Noel Cooper’s childhood memories at Walled Lake, the firm’s name embodies the peace of mind they want clients to feel about their financial lives.
• Philosophy: Their mission is to enable clients to enjoy life, free from financial worry, by handling planning and monitoring for them.
• Quote:

  "If I could give you 1 or 2% better return for the rest of your life, but you stayed awake at night, would it really be worth it? ... We want people to have a sense of comfort."
  — Howard Klieger [08:23]

4. Portfolio Construction, Volatility, and Client Reassurance

[09:03–12:32]

• Embracing Uncertainty: The firm admits to not knowing the market’s future, instead building portfolios robust enough for both up and down markets.
• Tailored Plans: The focus is on the client’s actual needs (e.g., why chase 10% returns if 3% is all that’s needed?) and on adjusting plans, not overreacting to volatility.
• Behavior During Downturns: Klieger reassures clients during market drops by revisiting their goals and showing that essential needs remain protected despite fluctuations.
• Quote:

  "We design plans... to pay for people's lives through up markets, through down markets. People still have to eat, people still have to pay their mortgages."
  — Howard Klieger [09:46]

5. The Value of Professional Guidance vs. DIY, Especially for Entrepreneurs

[12:32–14:48]

• Expertise Matters: Howard warns against the “first-timer” fallacy—assuming that intelligence in one field translates to competence in wealth planning.
• Entrepreneurs vs. Committees: He finds business owners are often better at making necessary changes, while executives may get bogged down in analytic indecision.
• Quote:

  "Expertise in one field does not make you an expert in other fields. Although the narrower your expertise, the more you think so."
  — Howard Klieger [13:13]

6. Behavioral Finance and the Psychology of Money

[16:27–19:39]

• The Real Driver: Klieger asserts that investing success is as much behavioral as it is mathematical—helping clients avoid emotional mistakes, like panic-selling in downturns or chasing highs.
• Recency Bias: He explains how people’s memories of recent events distort rational decision-making, using relatable examples from investing and life.
• COVID Example: During the crisis, rather than panic-selling or freezing, his team remained focused, adjusting portfolios sensibly.
• Quote:

  "What industry, when the prices go down, people want to buy less—they want to sell, and when the prices go up, people just want to buy more? ... It's the nature of the human brain."
  — Howard Klieger [17:37]
  "If you miss the five or six best days of the year, you lose two thirds of your return."
  — Howard Klieger [19:55]

7. Generational Wealth: Legacy, Communication, and Family Dynamics

[19:56–24:09]

• More than Returns: Klieger stresses the importance of aligning money with life goals, legacy wishes, and philanthropic aims.
• Communication Is Key: Family disputes often arise from lack of transparency—even well-intentioned estate plans can spark resentment if not discussed openly.
• Quote:

  "On that issue of communication, when you finally build your plan, your estate plan, get your kids in a room and let them know what it is, or else you could be launching a time bomb."
  — Howard Klieger [22:38]

8. Market Outlook: Opportunities, Risks, and Economic Concerns

[24:09–28:38]

• Wall of Worry: Klieger warns that fear and volatility often present opportunity ("Wall Street always climbs a wall of worry") but stresses aligning portfolios to real needs at all times, not just reacting to market moods.
• Inflation & Debt: He is particularly concerned about mounting US and global debt and sees long-term inflation as a real risk.
• Technological Disruptions: Points out risks and potential government/social impacts of AI and associated resource strains.
• Quote:

  "I used to believe there was an intelligent way out of our debt situation... but I'm not sure that's going to happen anymore... I think we're in for some highly inflationary times."
  — Howard Klieger [26:44]

9. Final Thoughts & Principles

[30:32–32:55]

• Planning Wins the Battle:

  "The battle is usually not won on the battlefield, but really won in the planning tent."
  — (Klieger’s partner, cited by Klieger) [30:41]

• A Goal Without a Plan Is Just a Wish:

  "A goal without a plan is really only a wish."
  — Howard Klieger [31:06]

• Direction Matters:

  "If you don't know where you're going, it doesn't matter where you end up." (Paraphrasing "Alice Through the Looking Glass")
  — Howard Klieger [31:50]

• Summary Principle:

  "Planning is better than not planning... If you don't have a plan, the other guy does. And Wall Street wants to part you from your money. So it's best to make sure that you know what you're doing."
  — Howard Klieger [32:47]

Notable Quotes & Memorable Moments

• "We're not here to just optimize for numbers. We're here to optimize for your life. If you can't sleep at night, it's not a good plan."
  — Paraphrased from Klieger's comments on comfort and planning [08:23]
• "Investing is more behavioral than it is economic."
  — Howard Klieger [15:37]
• "It's a leap of faith hiring an advisor. At some point you just have to decide to make a change."
  — Howard Klieger [15:19]
• "Wall Street always climbs a wall of worry."
  — Howard Klieger [24:35]
• "Planning is better than not planning. Even in sports—you walk onto the court and you have a plan. If you don't have a plan, the other guy does."
  — Howard Klieger [32:37]

Suggested Timestamps for Reference

• [00:34] Klieger’s career and shift to planning
• [05:10] Foundational sales and client service lesson
• [07:16] Walled Lake Planning’s name origin
• [09:33] Handling volatility and client plans
• [13:04] Importance of professional wealth advice
• [16:27] Behavioral finance explained
• [19:56] Family dynamics and legacy planning
• [24:33] Market risks/opportunities and economic outlook
• [30:32] Closing thoughts and quotes on planning

Tone & Style Recap

The episode is approachable, wise, and strongly oriented around trust and practical, lived experience. Klieger’s warmth and depth of knowledge shine through as he discusses not only numbers, but the human side of wealth—emotions, relationships, and the need for thoughtful planning.

For listeners seeking a humanized, deeply practical view of wealth and legacy management—and the importance of planning over simple returns—this episode delivers actionable insights from a seasoned pro.