The negligence that led me to DIY investing


Guest post from AR (Accidentally Retired)

Growing up, my Grandpa was a “financial advisor.” Or perhaps he was a stock broker? I’m not sure. Whatever you want to call his profession, there was no doubt that he was a brilliant salesman, a lover of people, and someone who would talk your ear off for days.

So whenever we’d spend time together we’d all hear all kinds of wild stories. We’d hear war stories that included run-ins with General MacArthur during his tour in Korea, or the story of how he was severely wounded in battle and lucky to be alive. Or we’d hear stories of his time growing up in Brooklyn and how he swept my Grandma off her feet. And of course we’d hear about stocks, mutual funds, and his favorite thing ever: annuities. 

I loved my Grandpa. 

I respected my Grandpa. 

Most of all, after growing up with a financial advisor in my life, I never thought about becoming a DIY investor. In fact I didn’t even know it was possible. 

My Grandpa handled my money for me from my 13th birthday on. I had an account with him, and it performed. Or maybe it didn’t? I’m not sure I would know, because I never checked. 

Grandpa eventually retired in my early twenties and my investment account was left to his younger partner, who he had brought in years earlier to facilitate his retirement. I met with his partner and I liked him. I kept my small amount of investment money with him. 

All was well for a few years. But then one day, POOF, he vanished. 

My account was transferred to a new advisor without a word from my Grandpa’s partner. I didn’t get it. I was pissed. My Grandpa had worked to build up a huge book of clients over the years, the least the guy could do was keep me on!!! 

But what did I do? Nothing. I was too focused on building up my own business.

By this time, I was in my mid-twenties and not the least bit concerned with my investment portfolio. I was working to build a successful startup, and I knew that the startup would one day build real wealth for me and my family.

So I simply ignored my taxable brokerage for years. Investing is not for twenty-somethings, I thought to myself. 

Fast forward a few years, and now I was 30, and my business partners (the founders) were on the verge of selling our business (it was going to close any day now). I knew that the proceeds were going to come in soon (my F-you money), and I would want to invest my humble nest egg into the stock market right away. 

I had heard that my uncle was working with a “very good” financial advisor. I had him make an introduction, and we started talking. He seemed to really know his shit. He was talking circles around me. Here I am, a 30 year old who is running a startup. What do I know about investing? You know nothing, AR.

The cold hard facts are that I didn’t bother to interview any other financial advisors. 

I didn’t shop around. 

I didn’t even ask any good questions. I didn’t know what to ask. 

I’m too busy to even think about this.

And I was busy. Seriously. Selling a company to a billion dollar company, as you can imagine was  involved. VERY involved. It took additional time, travel and frankly was a giant pain in the ass. I don’t recommend it. 

But we closed the deal. We did it! I phoned my new financial advisor and started to set up the new account. My wife wanted to meet with him as well, so we drove over and met him in person at his office. Did we want to invest conservatively? Yes. “Take no risks”, we told him. “I am a fiduciary,” he said. “It is in my best interest to work for your best interests.” Sounds swell, we thought.

A few weeks or maybe it was months later, we had everything running smoothly. So smoothly, that I didn’t hear from this guy very often. The economy at that time wasn’t doing great and so our conservative investments pretty much went nowhere. Not up. But not down either. 

Now, I’m sure by now you may be thinking “Uh, oh! This AR guy is about to get hosed out of all of his money.” – No, that is not what happened. This guy wasn’t a scammer. He was a real life financial advisor. And he was a salesman – like my Grandpa. 

Nothing horrible happened from here. But nothing great happened either. 

We paid our AUM fees of  1%+. Only we didn’t see them…they were tucked away nicely. And we had no idea of the real long-term damage that they were inflicting on our portfolio.

Every year I received a“Happy Birthday AR!” email and an invite to the swanky client party that always seemed to come a day late or perhaps not at all. 

Even with conservative allocations, our portfolio still grew as the bull market took off. All was well. Only it wasn’t. 

I couldn’t tell exactly what it was, but something was wrong. I just didn’t realize that the something was me.

Finally, I stumbled upon JL Collins’ stock series, and his Manifesto. The gears were turning…

Index funds? DIY Investing? I had never, EVER, considered it. Not possible. You have to have a financial advisor.

My gears continued to turn, and by now I knew in my gut that Index Investing was the path forward. I just didn’t have the guts to pull the trigger yet. 

Then, I ended up Accidentally Retired. I had more time. I started reading investment books and personal finance blogs. Soon, I was more knowledgeable on investing than I ever hoped that I could be. 

And so a few months into my mini-retirement, I started to interview other financial advisors. I started to be able to “talk the talk” and understand the game. I met with advisors from Vanguard to Personal Capital to Merrill. 

Then I read these words:

If you are a novice investor you have two choices:

1. You can learn to pick an advisor.

2. You can learn to pick your investments.

The Simple Path to Wealth 

Finally, after all these years, it clicked. I can learn to pick my investments. I have already learned. I don’t NEED a financial advisor.  

With my wife onboard, I called my financial advisor. I told him that I had to take a shot on myself. His response was “OK.” – He didn’t even TRY to talk me out of it. I had fired my financial advisor…and his reaction was literally NOTHING!

It was in that critical moment, that I finally really understood that I am the best person to pick my investments. I chose myself. 

And like many of you reading this, I hope you have too. 

But if you were on the fence like me, or if you have had a financial advisor for years, like me, I ask you to follow the great advice of JL Collins:

Pick your investments. Choose Index Funds.

The great irony of successful investing is that simple is cheaper and more profitable. Complicated investments only benefit the people and companies that sell them.

The Simple Path to Wealth 

This was spot on for me. The great irony of my experience with my financial advisor was that it was far more complicated than it needed to be:

  1. We were invested too conservatively for our age and time frame.
  2. We were paying higher fees than we thought (it was 1.2%).
  3. We were invested in complicated and proprietary mutual funds, some of which required a 6 month notice to sell.
  4. We couldn’t move a majority of our holdings to another brokerage without taking capital gains.
  5. We had no idea what our tax implications were. No idea about dividends, capital gains or anything else.
  6. As a smaller client, we were largely ignored by our advisor, who was constantly on the road trying to drum up more business.

And this was all our financial advisor’s fault! 

Except it wasn’t.

I only had myself to blame. 

I might have been a busy partner in a growing startup. I had numerous direct reports to manage, strategic partners to meet with, operations to run, cash flow to manage. But it didn’t matter. That is all an excuse.

No matter how busy you are, you should always, and I mean ALWAYS, make time for your own investments. There is no other way. 

There is only The Simple Path to Wealth. This is the path that I am now on.

I’ve been a DIY investor for nearly a year. It is easier than you think. 

You don’t have to do it all in one night either. Here is what I did:

  • Started to read financial books and blogs.
  • Tested the waters by moving my former 401(k) into a self-directed Rollover IRA. 
  • Wrote out a financial plan for my family.
  • Read more books and more blogs.
  • Built out a transition plan by figuring out what could be easily sold or moved and what could not.
  • Finally, I took the plunge.

It was not an overnight process. This took me 6 months of careful planning to get it right. It then took 6 more months to fully transition away from my former brokerage. 

And while it WAS daunting to move away from my former brokerage and from my reliance on advisors – I did it. There was even a fund that took 6 months to get out of. It’s all transitioned now. 

Growing up with a financial advisor in the family, I was programmed to believe that it was someone else’s job to manage my finances. It took me three financial advisors to realize that this is absolutely not the case.

Ironically, it was my own negligence that led me to become a DIY investor. 

If you are considering becoming a DIY investor at all, then you already have the chops to do it. 

YOU are the main driver of your financial future. And you can learn to manage your investments!  

It doesn’t take as much work or effort as you think! 

What would my Grandpa think of all of this? I would like to think that he would pat me on the back and cheer me on. He built up numerous businesses over his lifetime from nothing. One of them just happened to be a book of business as a financial advisor. He wasn’t a financial guru in any way – he was a salesman and a damn good one at that. I’m sure he is proud that I finally took the bull by the horns and plunged head first into DIY investing. 


Afterword from JL Collins…

When I approached AR to write a guest post here, he came up with the idea of telling the story of his transition from using an investment advisor to handling his investments on his own — better, cheaper and more simply.

I loved it.

Ever since my Stock Series and the post in it Why I don’t like investment advisors, the question of how to make this transition comes up frequently. Here is one man’s journey.

So, who is this guy?

AR is a 37 year old former CEO of a bootstrapped startup that he sold in 2015. His company was divested in early-2020 and, suddenly, he found himself Accidentally Retired. His newly minted blog of that name chronicles this new phase of his life, his…

“…journey to becoming a better father, husband, investor, and to conquer the ultimate question of how to live a happy life and be my best self.”

Launched just this year in January, his blog has already made its mark on the FI community and has been named a Plutus Finalist in two categories: “Best Financial Independence or Retire Early Content” and “Best New Personal Finance Blog”

In this post, he has been very generous in crediting my work, but pressed he confesses that early on these books also really drove it home for him:


Speaking of books, here are three I’ve recently enjoyed:



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Important Resources

  • Talent Stacker is a resource that I learned about through my work with Jonathan and Brad at ChooseFI, and first heard about Salesforce as a career option in an episode where they featured Bradley Rice on the Podcast. In that episode, Bradley shared how he reached FI quickly thanks to his huge paychecks and discipline in keeping his expenses low. Jonathan teamed up with Bradley to build Talent Stacker, and they have helped more than 1,000 students from all walks of life complete the program and land jobs like clockwork, earning double or even triple their old salaries using a Salesforce certification to break into a no-code tech career.
  • Credit Cards are like chain saws. Incredibly useful. Incredibly dangerous. Resolve to pay in full each month and never carry a balance. Do that and they can be great tools. Here are some of the very best for travel hacking, cash back and small business rewards.
  • Empower is a free tool to manage and evaluate your investments. With great visuals you can track your net worth, asset allocation, and portfolio performance, including costs. At a glance you'll see what's working and what you might want to change. Here's my full review.
  • Betterment is my recommendation for hands-off investors who prefer a DIFM (Do It For Me) approach. It is also a great tool for reaching short-term savings goals. Here is my Betterment Review
  • NewRetirement offers cool tools to help guide you in answering the question: Do I have enough money to retire? And getting started is free. Sign up and you will be offered two paths into their retirement planner. I was also on their podcast and you can check that out here:Video version, Podcast version.
  • Tuft & Needle (T&N) helps me sleep at night. They are a very cool company with a great product. Here’s my review of what we are currently sleeping on: Our Walnut Frame and Mint Mattress.


  1. Frogdancer Jones says

    I enjoyed reading this.
    I retired last year and am managing my own finances. I’m definitely not a Maths person, yet what AR says is right. If you take the time to educate yourself, it’s not that hard to do.
    The hardest thing about it is finally taking the plunge.

    • Kevin says

      What is a “Maths” person?

      Loved the article! Thank you very much!

      All five of the book links at the bottom do not display the image (broken image). The links work, but the image display does not.

      • RobDiesel says

        A maths person is someone how knows/likes/intuitively is able to do mathematics.

        Basically, dealing with numbers. I’m guessing a lot of us think we need to be one to be able to invest for ourselves, but I don’t feel we do.

        • Accidentally Retired says

          @FrogdancerJones & @Kevin – Glad that enjoyed it!

          @Rob – You are spot on. I am a “maths” person, and yet I was still intimidated by investing. I bought into the myths, lies and confusion of financial advisors and the system that makes it far more complicated than it has to be.

          Thankfully Index Funds have presented us average joes with the ability to invest with confidence and easily. And while I wish I knew about Index Funds earlier on, it is never too late to start — and you certainly don’t need to be a maths person!

          • Kevin says

            Thanks. I guess I had just never seen “maths” in the plural. I’ve always been a math person – the kind of person that uses spreadsheets for everything and anything – and all this finance stuff just revs me up. I love your book and your blog and have learned so much.

      • Chad says

        “Maths” Is British English (pronunciation) and dialect. Short for MathematicS (with the acknowledgement that there are different forms (algebra, geometry, calculus, trig, etc.). Sometimes used in Ireland and Australia as well.
        *Note: I became aware of this in college (or as the counterparts overseas call it “University”) as an American playing soccer alongside European players. Big world out there with some cool stuff!

  2. FreshLifeAdvice says

    Love to see the AR and JL collaboration! Thanks for detailing your investing story AR – really enjoyed the read and JL’s commentary. I’m so grateful to have come across index funds as soon as possible in my investing career.

    • Accidentally Retired says

      Yeah, the earlier the better. Sometimes we have to make mistakes to realize the error of our ways. This was definitely the route that I took, BUT if I can help others avoid the same path earlier in their investing career, it will have been worth it!

  3. LJ says

    After reading The Simple Path To Wealth, I immediately had a full Arsenal of financial weaponry to go it alone. My biggest fear was breaking the news to my long time Financial Advisor. It took me several weeks if not months to get the courage to cut him loose, to the point I even felt guilty and had to rehearse what I was going to say to him. And when I did his reaction was also nothing, I realized at that moment that every word that JL Collins wrote about that topic was absolutely gospel. This advisor acted like he was part of our family for years was nothing more than a skilled actor and great salesman getting his 2% AUM on the front end alone. No doubt the best financial decision I ever made.

    • Accidentally Retired says

      Amazing that you got nothing as well! That was sort of a big “aha” moment for me too. Like you’re not even going to try to fight it? For many of us who use a an advisor, even if you know in your gut that it is time to leave, it is like a breakup. It is hard.

      I’m glad that you worked up the courage to cut him loose and that it was a great decision for you as well. Cheers!

  4. Andrew says

    Loving your articles and Simple Path to Wealth. How about the risk of having everything at Vanguard? I am thinking of 1) the company itself somehow screwing up, 2) identity theft that allows someone to empty my account(s); 3) other. Would love to hear your comments, given how much you (and I!) believe in putting so many eggs in their total market index fund.

  5. Scott S says

    Hi Jim,

    I stumbled across an eye-opening article on Joshua Kennon’s blog “Mail Bag: Buying Stock When Valuations Are High”. The article itself was nothing new, but the comment section brought to light something I’ve never considered about holding VTSMX in a regular brokerage account. Apparently, the fund has a lot of embedded unrealized capital gains and if forced to liquidate in a panic could leave brokerage investors paying the tax bill for gains they didn’t necessarily benefit from. This wouldn’t matter if held in a tax-sheltered account but could be a massive liability when held in a plan brokerage account.

    He even sites some examples of this happening in recent history (Vanguard Mining Fund). I hold a large chunk of VTSMX in a brokerage account and this got me thinking. I would love to know your thoughts. Have you ever considered this risk?

    This information is pretty important for us “do-it-yourself” investors.

    I would share a link to the article but I don’t want this message to get flagged as spam.

  6. Mike L says

    Good evening all. I had a quick question I might be able to get some clarification on. If I sell out of my current fund in my vanguard ROTH IRA and move that money to a different index fund within my roth will I incur penalties for that, or is this a taxable event? I currently have my fund in a vanguard growth index fund which has done really well, however I’d probably like to eventually move this over to VTSAX. Any help would be greatly appreciated.

    • Dyna says

      Hi Mike why would you need to sell? You can exchange your holding to your preferred fund within the Roth IRA to by pass your concern. Unless I misunderstood your ask.

  7. Passive Canuck says

    I found it really funny and ironic that your ex-financial advisor was so relaxed about you telling him you’re moving on without him. I had a similar reaction from mine when I decided to go solo and begin my self-directed investing journey.

    I think the best part about my system now is that I’ve found a good flow where it’s passive enough for me to just set and forget most of the time, especially with some of the tools (apps and such) I can use to skip a lot of the time consuming parts (stats and analytics for instance).

    Just a side question, what are your thoughts on Covered Call ETFs for self directed investors who aren’t completely knowledgeable about options trading to start off?

  8. Jeff says

    I like the article and agree with the end conclusion but I do want to point out, AR specifically instructed his advisor to invest conservatively and take no risk. That’s why his portfolio underperformed the markets. Also it sounds like AR wasn’t dollar cost averaging into his portfolio either. He was just letting his lump sum float while he invested in his business.

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