40 Year Old Entrepreneur Ready to Be Done!


Dryer sheet aficionado
Jun 6, 2011
As a lurker for a couple of years that is approaching FIRE in our future, I feel compelled to finally make my introduction and join the conversation! I enjoy reading the forums daily, always taking away some education and more importantly motivation!

My wife and I are 40 and have two teenagers. We are starting to really look at what we want to do once the kids enter college. We have a target of retiring at 44, or at least being in position to make decisions about a “reduction in labor.”

I started my own business at a young age and have seen it grow continuously and significantly for two decades, but I am really ready to step away, but the entrepreneur and saver in me may struggle with moving from the saving mode to spending mode. My wife works part-time in a professional office.

We paid off the final $85,000 on our mortgage in 2010 (home value about $250,000 now). The stock market would have provided some pretty nice returns over the last 2 ½ years since we paid it off, but I wouldn’t trade the peace of mind having a paid for home!

Our investments total about $2,200,000. Detailed below. A recent report had 97% in stocks , 3% in REITs. In 2009, we decided to enlist the help of a fee-only registered investment advisor. Holdings include Vanguard funds, ETFs, etc.

Joint Acct: $1,294,000
Simple IRA: $224,000
Her 401k: $89,000
IRAs: $220,000
HSA: $53,000
(we cash flow medical expenses and max out our HSA contribution)
Cash: $77,000
Kids CSP: $115,000
(no longer adding to CSP, will cash flow any additional expenses)
Kids UTMA: $75,000

I’ve read some milestone threads, and may throw these there too, but here are some of our noteworthy milestones along our journey:

$40,000 in investments at age 25
$1m in investments at 34
Paid off mortgage early at 37
$2m in investments at 39
$2.2m in investments currently

We are fortunate to have a large shovel. In 2012, we added $180,000 to our investments, $177k in 2011 and $100k in 2010k (plus $85k to payoff mortgage). In the last 9 years we’ve averaged adding $117k to our investments.

We have been very fortunate, but we’ve also been very good savers. I started investing $50 and $100 per month to a few Vanguard funds and as my salary increased, we added to our level of investing.

In 1998, we were in our mid-20’s and stuck $18k into our retirement and taxable accounts. In 2012, we hit a new personal best by adding $180k to our investments.

Our spending is in the $75,000-$80,000 ballpark.

One scenario I am considering with my business is to reduce my work down to a low stress 4-5 months per year and maintain a salary of about $100,000. My thoughts are leaning towards cutting back the business when I am 43 or 44 and then maintain the remaining business until about age 47-50.

I’ve run FIRECALC with various numbers and usually it shows 100% success rate in 91 cycles. The numbers I’ve entered would be to work 4 more years (investing $100k each year), then I put in a lump sum contribution the next 3 years (reduced work) that would mean we would not tap into investments until 2020 (age 47).

Thanks to everyone that contributes to the forums and provides guidance, ideas & their own experiences for us to consider & learn from.

2017 Hopeful?!
welcome to forum retire44. Impressive savings but 97% in stocks is too much - plan on rebalancing and have some safety(70/30 ?). I'm currently 80/20 and in the process to rebalance around 65/35 - waiting for FA to analyze my portfolio and suggest a mix.
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Congrats on your achievements! I'm just a few years younger than you, and a few $ lower on the portfolio rung, but can appreciate your concerns as well as goals.

Two comments about your data:

Our investments total about $2,200,000.

Kids CSP: $115,000
(no longer adding to CSP, will cash flow any additional expenses)
Kids UTMA: $75,000

1. For retirement purposes, I'd strongly advise against counting your kids' CSP and UTMA accounts as YOUR portfolio. Legally, you can't, and I sure wouldn't want to allocate $190k to my kids' accounts and plan on spending that for my own, when it either has to be used for college education or incur a penalty (I'm assuming they're in 529 plans?), or else outright in their names and are accessible to them and them only when they're of legal age in your state.

Even with subtracting out the $190k, I don't see much concern...but would rather be slightly conservative than creative in this accounting. :)

2. Regarding your portfolio - I would also recommend perhaps slightly more fixed income. Personally, I lean towards preferreds and a few closed end funds that have higher yields...but as long as you're very widely diversified in your equity investments (in terms of % in each stock - didn't know how much you might have in individual stock holdings). My fixed income is only about 14%, +/-, but my overall portfolio is widely diversified and my plan is to live off my dividends when I pull the plug...so a high equity percentage isn't too worrisome for me since I won't be as dependent upon selling my holdings to fund my lifestyle.
Thanks for the replies -- we've had that discussion about adding bonds, but we do have a very diversified portfolio (without pulling up exact percentages at the moment) of index funds and etfs, no individual stocks.

I listed the college savings plan and UTMA's for overall view of the portfolio and to show that college was pretty well covered. The UTMA's are the kids' money from gifts they've received, saved or earned. The college savings plans are funds that my wife and I have invested. If there are funds left after college, we would likely use them to help them with a first home or something like that. We are the owners of the CSP 529 plans, they are beneficiaries. As I understand it, we could take funds out and pay penalty and taxes as we own those accounts. The UTMA's are all theirs :)

When I run FIRE Calc and other calculators, I do not include the CSP & UTMA amounts, I just listed them here to show that college savings was underway.
Special feeling to be debt free, mortgage free. Bravo! You have the FI to write your own ticket, congratulations to you and good health to you and yours.
Congratulations Retire44. You are an inspiration for all the young, would be entrepreneurs out there. Given your expenses, you look like you have the FI part down pretty good. With some rebalancing to a more conservative AA you can add the RE at any time.
It may take a while to transition to ER if your mind is in your business. It's hard to find that fine balance point.
What happens to your business when your retire. It sounds like you should be able to sell it?
As I understand it, we could take funds out and pay penalty and taxes as we own those accounts. The UTMA's are all theirs :)

There is no penalty to cash out a 529 plan, you only pay taxes on the GAINS in the investments. An UTMA is an IRREVOCABLE gift to a minor. When the kid turns 21, that money is theirs. There have been lawsuits against parents who try to "hide" UTMA/UGMA assets from their kids, and it has ended badly for the parents almost every time. That is why I caution parents against throwing huge sums of money at UTMA/UGMA accounts.........;)
It might be possible to sell my business, very unique and very dependent on my skill set, would be a limited market to sell to; planning retirement as if I would not sell it.
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