A Fiduciary’s Reading List

I’ve completed William Bernstein’s recommended reading from his eBook, If You Can.

The reading humbled me. With a 1st Class degree in Econ / Finance, and 20 years experience in international investing, I was left feeling intellectually arrogant and ignorant. Each of these books challenged my beliefs while explaining financial history.

I’d recommend making these books compulsory reading for your advisers and key family members.

Good people can be found in the field of finance. I appreciate the significant time that each of the authors spent to educate willing readers.

The Millionaire Next Door – introduces the key concepts of wealth, saving, investment and taxes

Your Money & Your Brain – a solid summary of the latest on behavioral psychology as it relates to finance and investment – why I will always fool myself

The Great Depression: A Diary – an inside look at what it is like for a conservative, professional family to live through a depression – 2008-2010 was easy compared to the 1930s – could your family survive on minimal income for multiple years?

All About Asset Allocation – the early chapters were the most useful – simple explanations of the role that volatility plays within a portfolio – reading this book, you’ll be tempted to seek the perfect portfolio mix – my decision has been to keep it simple

Common Sense About Mutual Funds – a wealth of information – Bogle picks apart the industry by making his case for simple and low-cost investing – the book makes one wonder how brokers and financial advisers can sleep at night – readers will learn about the industry structure that silently fleeces its customers

Side Note: if you worked in finance from 1980 to 2000 be sure to adjust your brilliance for volatility and leverage using Bogle’s updated charts. We had one heck of a tailwind. Humbling!

How A Second Grader Beats Wall Street – don’t be fooled by the child-like title – this book will save your family tens of thousands of dollars in fees and taxes

Devil Take the Hindmost – a history of financial speculation – hedge funds in the 1860s & derivatives in the 1600s (!) – as Taleb says, we’re never going to get rid of greed, the challenge is to build the system so the greedy don’t inflict suffering on the good


To Bernstein’s list, I’ll add Estate & Trust Administration for Dummies – a good primer to get you thinking outside of your own self interest.


If you are in an advisory, or trustee, relationship then tick off one book per meeting with your professional team.

Read a book, take notes and discuss how the book impacts your family (or your firm).

Challenge yourself with exposure to the best ideas available.

Studying new approaches can be painful but we all benefit from a bit of cognitive dissonance.

What Do We Need To Retire?

My post showing how a 1.2% fee differential can cost you 131% of your pension contributions inspired Paul Meloan to write an article about The Clear Value of Financial Planning. The article lays out Paul’s case for his work in the field.

To help you understand the cost/benefit relationship, have your advisers write out the dollar amounts that you’re paying in fees, expenses and taxes. Be sure they include all the soft costs that are buried in your mutual funds.

In Paul’s article, he lays out questions for a family to consider. I thought I’d answer these questions, as viewed from a life outside the box.

#1 – How large of a pool of assets do my significant other and I require in order to live in the manner which we desire for the rest of our lives?

The most important thing for you to remember is to declare victory immediately. You have more than you need and are in a position to think about the future. Many, many people are less fortunate than you. Spending time with the less fortunate will temper your needs and get you to financial freedom more quickly.

The financial services industry is built backwards from your true needs. If you listen carefully then you can hear the industry say, “you can be happy tomorrow if you have more.”

Be happy now, with less.

I recommend that you flip question #1. When I look at my family’s net worth, I express it in terms of “years of current expenditure.”

For example, if your net worth is $500,000 (Assets Minus Liabilities) and your current expenditure is $125,000 per annum then you have FOUR years of current expenditure (500,000 / 125,000).

Why is this is a useful way to consider your position? It’s useful because it changes the conversation from

  • What do I need to be happy tomorrow?; towards
  • How can I spend wisely today?

The years-to-burn exercise reminds me that the fastest way to improve my financial position is to reduce my current expenditure, not take more risk.

In terms of years-to-burn, my peak wealth was 13 years ago. I was living out of a Subaru and sleeping on a friend’s floor in LA. My life was extremely simple – eat, sleep, train. It was one of the happiest periods of my life and my net worth was 1/6th of right now.

It’s worth repeating… I increased my net worth by 600% and feel less wealthy.

Historically, most my spending has been wasted.

  • luxury air travel
  • high-end hotels
  • excessive childcare
  • personal assistants
  • office space
  • non-performing assets
  • personal luxury expenditure (clothes, cars, boats, vacations)

I ditched most of these because I discovered that they were bandaids healing myself from a lack of satisfaction with daily living. My spending was driven by our culture rather than my needs.

Choose your hometown and your buddies carefully! I assure you that the exact same family will have needs that vary by geography. Consider:

  • Manhattan vs Boulder
  • Aspen vs Truckee
  • Palo Alto vs Greenville
  • Santa Barbara vs Hood River

I came close to moving to Palo Alto to spend more time with my pals (love you guys and gals). It would have changed my life – not better, not worse – but absolutely different.

The more time that you spend helping people that have less than you, the smaller your retirement fund will “need” to be. There are examples of this all around us.

Finally, the benefit of wealth is not to leave work. The benefit is to feel secure enough to choose meaningful work, regardless of compensation. Hang out with people that are rich in personal satisfaction (artists, priests, teachers, ministers, caregivers, coaches, guides) – you’ll know them when you speak with them.

#2 – What should be the composition of that pool of assets, and how should they relate to each other in terms of risk and expected returns?

You can beat all of your pals by using Bogle’s Little Book of Common Sense Investing.

As a bonus, the strategy is simple to understand and easy to execute.

If you can’t figure the book out then call Vanguard and they will help you in exchange for a fixed price fee when you need help.

If you keep screwing up then get yourself a financial coach and pay a fixed fee to hold you to your plan.

We all do better when someone is watching – that’s why I have a blog.

Getting My Affairs In Order

In March, I shared a family legal structure. Even with that structure in place, there will be significant admin for your family to sort when you pass. This admin will hit your spouse and children when they are least equipped to deal with it.

Given that people are useless at administration when they are grieving, how can you make life easier for your family? 

Simplify possessions, portfolios and personal legal structure. Almost everything we have will be sold, donated or disposed. Streamlining yourself, in advance, is an act of love that will save your kids days and weeks of effort. If you have mementos that are special to you then sit down your kids, and grandkids, for storytime. Use the pictures and personal effects to make your history, their history. Without this effort, your memories will end with your passing. Your kids will treasure their memories when you pass. 

Brief your successor(s) – consider the roles that you play in your family (financial, administrative, emotional), who’s backing you up? Do they know it? Have you explained their role to them? Do your successor(s) have written plans and checklists to work through? It’s far easier to update an existing plan than to create one when you’re under the stress of an unexpected event.

Establish A Joint Operating Account – Start with a joint operating account with your spouse. As you age, consider a joint account with your most reliable adult child. In my family, at least half of us have bodies that outlive our minds. It’s very likely that I’ll need to hand off to one of my kids at some stage.

Consider Medical and Financial Powers of Attorney – These roles require different skill sets – consider splitting. Have an honest conversation with the individual you’re considering to help you out. Are they willing, and able, to fulfil their role.

Consider Probate – If you died today then would your estate require probate? What are the costs, and disclosure requirements, associated with probate in your locale? Are you OK with that? What are the steps necessary to avoid probate?

Clear Instructions – make your Will crystal clear, simple and easily available when you pass. Brief your executor, and personal representative, well in advance.

Proactive Disclosure – Hold meetings with your financial/admin attorney, your medical representative and your spouse. I’m 44 and have a quarterly state-of-the-family meeting with my succession team. Not because I expect to die anytime soon, rather as an insurance policy to lessen the blow on my loved ones if I’m taken out at short notice.

Sorting the above doesn’t make coping with death easy, but it does go a long way towards reducing the chance that your survivors are overwhelmed, or ripped off.

Be very careful with financial powers of attorney and signing rights over your assets. I’ve seen fraud within families and between lifelong friends. Establish structures that limit the ability to one corrupt individual to hurt your family. Remember that even competent people make mistakes.

When you think you’ve got everything sorted – try explaining it to a trusted friend. Once you’ve explained it to your pal, have them explain it back to you. I guarantee you’ll learn something.

Three tips for estate planning:

  1. Say what needs to be said, today.
  2. Be a hero now, not when you pass.
  3. You’ll get the greatest satisfaction from sharing gifts (in person) with the people you love.


Denver Bar Association: what to do when someone dies

Colorado Bar Association: personal representative and trustee under probate

When You’ve Made Your Money

By the time I was 32 years old, I had created a life where I had the option of working parttime. For the most part, I got that opportunity “right” and enjoyed my freedom.

My errors came from from the thought (perhaps the lie) that spending yields happiness. That belief, shared by most my peers, pulled me back into fulltime employment twice over the last decade.

The first time I was pulled back, it was to help a friend start a business. There was huge equity upside and I loved the work. It was a good decision but I ended up over-extended financially. Thankfully, I started selling down in 2005 and, in the Great Recession of 2008, “only” lost 2/3rds of my net worth.

The scale of the losses was equal to what wiped out my grandfather’s generation. In the four generations of my family tree (that end with me), we’ve lost enough money for the entire family to never have to work a day in their lives. The bulk of my current job description (father, teacher, administrator, spouse, brother, uncle, trustee) is trying to reduce the frequency, and consequences, of these bad decisions.

When I took my big financial hit, my cost of living (2008) was 5x higher than what I spent in my first year of “freedom” post-college (2001).

Due to the bankruptcy of the business I’d been advising, I was under a tremendous amount of stress. Reflexively, I chose to cut expenses and replace income. My family’s 2009 expenditure was half of 2008, but remained 2.5x higher than what I spent in 2001. I focused on my back-up career of coaching (always have Plan B!) and managed to cover 50% of what I was spending.

At that point, 2010, I didn’t know what to do. Inside my personal business plan, I have a heuristic “if in doubt then wait.” So I repeated the year, with a couple exceptions, Axel (2011) and Bella (2012).

Gradually, across 2011 and 2012, I realized that preserving the status quo (large house, dad working to pay bills that don’t make him happy) was insane. Despite being complete insanity, I was following a path that had universal support in my peer group. As my kids popped up, I noticed that I was getting less and less fun to be around AND I was actively working to create a life outside my house.

The family readings that I shared, and my family history, show that it’s almost certain that we will wipe ourselves out (perhaps more than once) in the next seventy-five years.

What should you know about your money?

  • Most of any financial legacy will be gone a couple decades after my death, or spent by people I never knew
  • The greatest pressure I experience is preserving wealth that I’m unlikely to spend
  • I know I can live in peace on a fraction of my current spending

What do I truly need? Easy to answer day-to-day: exercise, love, service and health.

For the long-term, I like to have a mission. Why not make the people I live with part of my mission? Then I’m surrounded by meaning, and success. If that’s the case then what does my family truly need?

Empathy – it’s easy to find people to do stuff. It’s a lot tougher to find people to listen and care.

Learn To Teach Ourselves – my writing is about sharing how I teach myself. Tools that I want to pass to my kids: write down insights and blindspots, make errors visible, replace habits that hold us back and share stories of what you’d like to become.

Cope With Loss – More by accident than design, I’ve been on a self-guided education of the major faith traditions, neuroscience and behavioral psychology. This has led me to believe that loss is an opportunity to learn by experience. Until life deals us a major setback, we will not understand impermanence and the nature of existence. Create a daily practice that let lets you process, release and recharge from the challenges we all face. Deal with loss by continuing the good that you’ve learned.

My kids weren’t around for for the first 40 years of my life. Common sense means I won’t be here for the last 40 years of their lives.

What’s your legacy?

Good memories and a skill set that let’s the student surpass the teacher.

Financial Karma

Having been raised in a Judeo-Christian household, I used to define karma with reference to “sin.” For example, karma is my sins coming back to haunt me. 

Over the last year, I’ve learned a wider definition that goes like this… historical and current choices result in the life I have right now. I prefer that definition as it reminds me that I change the future with decisions today. At 43, our family’s balance sheet is an expression of my financial karma. 

I grew up in Canada, a country where there’s a social contract. The system isn’t perfect but it works for many Canadians. Living in the US, most prefer a model with greater self-reliance. Both systems have their strengths and create different incentives.

The book I referenced last week, makes the point that, historically, people relied on family, rather than government. What are the areas where family support can assist, without screwing up incentives?

As a young man, being an aggressive saver made me happy. I have no idea why, likely a habit that was built from a very young age. With three kids in my house, my desire to sacrifice today, to enable security tomorrow, remains strong. At a deep level, it feels like the right thing to do.

Boulder is an environment with a lot of financial wealth. The focus in Colorado isn’t as consumption-centric, as my previous homes in London and Hong Kong, but my reality is a far more expensive life than what I had created in New Zealand. 

Part of my annual review is asking myself the question, “Am I getting value for money within my current life?” Being honest with myself, the answer is “not yet.”

A key part of this year’s review has been completing a five-year plan to get my family to cash flow breakeven. When I became unemployed at the end of 2008, I gave myself a pass for five years to take stock and see what happened. The four year anniversary of that decision is approaching and I have a good idea where I want to take the family.

Long term, I have been considering the life I want to live in front of my kids. A parent’s life choices are powerful lessons on effort, consumption and strategic management.

I see a benefit to the kids of taking my consumption down. Expectations management is something the Kiwis do very well. All my pals in Christchurch understand the relationship between work-results-satisfaction. It is a very grounded society and I enjoyed my time there.


  • What are the most useful elements of financial wealth?
  • What does my life say about my attitudes towards wealth?
  • Are my current choices aligned with my family values?
  • How best to give my kids a chance to be successful: in their own terms, relative to their peers and relative to myself?

I’ll end with book recommendation: Wealth in Families by Collier. Another title that is valuable regardless of your net worth – the sections on anchors and family management contain a lot of good questions for parents to consider.

I measure true wealth in freedom.

A Life’s Work

Last week, I was on retreat, cycling daily in the mountains. Getting outside my normal life, offers me an opportunity to reflect on three questions.

  1. What will be my life’s work?
  2. How did I do, today?
  3. Am I aligned?

As a young person, my first realizations were not-to-dos. I’m still best at telling myself what to avoid (excess booze, sloth, late afternoon naps, overeating, anger, holding my breath, fatigue). It is easier to see where I don’t want to take myself than to consider my purpose and what I want to leave behind.

Various lightning bolts from my past…

  • Not to be unhealthy (mid-20s)
  • Not to be inactive (late-20s)
  • Not to gain satisfaction from a lifetime of accumulation of wealth (early-30s)
  • Not to spend my life dragging boxes across a screen (early-40s)

Each realization struck me quickly, and powerfully. It was obvious that my current life didn’t fit. Following that realization, I would redirect myself.

When we think about “legacy”, most of us consider financial wealth. I’ve considered my family tree.

I’m the first-born of the first-born of the first-born – everyone upstream being quite young when they had kids. So I have been fortunate to watch, and learn about, many generations. In looking up my own family tree, there have been a few members that hit-it-big over the last century. Regardless of their financial success, nothing material passed more than two generations. When I die, everything in my family tree from the last 150 years will pass. This brings context to my question, how did I do today?

Being 40+ years older than my kids, they are an obvious target for having an impact or, at least, building a relationship so I might be able to have an impact. I ask myself, “what can I do that might prove useful to my great-grand kids?”

Have you considered what continues?