I’ve heard the many stories over the years of the lottery winners and professional athletes that end up bankrupt after having received many millions of dollars (Celtics fans may remember Antoine Walker). At first, it was shocking to me – how could anyone lose that much money so quickly? Then in a smaller scale I came into some money and immediately I had more empathy for these temporarily wealthy. There are so many companies whose sole purpose is to separate people from their money by selling non-income producing assets (like cars, homes, clothing, and jewelry) and experiences (like restaurants, shows, and travel); unethical people who prey on the uneducated and inexperienced with scams or over-promises; family members, friends, and co-workers with their hands out constantly for “loans” or gifts; and financial advisors who over-charge, over-churn, or outright steal.

I shared that I had a financially modest upbringing, and my parents didn’t have much experience or knowledge to share around personal finance. The only class I had in public school that even touched the subject was called Home Economics, where I was taught how to write a check and some basic budgeting. There were no other options in school to learn about money management, investing, or retirement. Since I grew up in a blue-collar town, none of my friends or their parents could share much either. Further, it seems that in our society, money is a taboo subject and politically incorrect to discuss, so it is hard to learn from other’s decisions. People with financially modest backgrounds who aren’t educated about money are easy marks for many.

I wrote previously about looking for paid financial help once I had some wealth – brokers, insurance agents, CFAs, CFPs, etc., and how all of those people need to apply a standard approach to their clients to scale their own businesses (so the result is cookie-cutter) and seemed to be expensive for the value provided. I personally found that paid financial planning help wasn’t a fit for me, so I ended up deciding to do that portion of the work myself, and build direct relationships with specific value providers – a low cost brokerage (for trading index funds and ETFs), a full-service brokerage for certain tasks (for buying individual muni bonds), a CPA (for taxes), an estate attorney (for wills, proxies, trusts), insurance agents (for life, home, auto), and a business attorney. But the one person I lacked, and which I really wanted and needed, was a trusted personal finance mentor.

Who do I consider to be a personal finance mentor? It is someone who has faced similar challenges and experiences, has similar or more financial wealth, probably has a few years on me in age, and has my best interests guiding their (unpaid) advice. After 20 years of looking, I haven’t been able to develop such a relationship in one person, but have found a couple people with whom I can discuss some of these issues. I believe that if I had found a person or these people earlier, I wouldn’t have made some of my financial mistakes – and no CFP/CFA/advisor/broker would have helped either.

Now I’m trying to help others and I’ve begun to develop relationships with several younger tech executives as their personal finance mentor. Many of them have asked to pay me, which I don’t accept (if I did, it would change the nature of the relationship and put our friendships at risk), and have encouraged me to start blogging about these topics. Their encouragement has led me to this little project, which I’m not publicizing and just trying out for a bit.

The bottom line is that there is very high value in having a personal finance mentor and I encourage everyone to seek out that particular person who fits the role. It will pay dividends!