I file jointly with my wife, so we use her as the real estate professional. We also use the 469 election which groups all activities rather than qualifying as a professional for each entity. This captures the losses on the K-1s from our passive investments as well as the companies we operate.

You are right about the interpretation of hours worked for qualifying individually. The most favorable for qualification would be block hours on your Delta timecard. Next most favorable is using pay hours. The worst calculation would come from using duty day. There are also some interesting interpretation possibilities for pilots on reserve. This falls squarely in the category of DYODD and get advice from a tax professional.

I've been reading up on the topic of Acquisition Entrepreneurship. Buy then Build by Walker Diebel is worth a read. Acquira is a company that follows this model with a JV approach for buying a business. The focus is on owning and running a business, not being the business. "Work on your business, not in your business" is a common theme among entrepreneurs who successfully scale.

 

except I can do better, but for set it and forget it looks good.

 

My side “hustle” for 2021 was just to enjoy the family and some new hobbies, all of which only lost money. But a steady stream of dollar cost averaging into effortless 401ks (dual income household) and keeping spending under control saw our net worth increase 37.9% and retirement accounts are up 34.5% YOY. I keep wondering if I’m missing out by not actively investing in stocks or other vehicles, but I’m not sure what I’d stop doing to make time for the active monitoring/research that must be required to make all that activity worthwhile.

 

You’re missing nothing. This is investing. Keep buying and sit on your hands. The more complex, the more models, the more valuations, the more ratios, the worse your investing will do. At least that’s been my experience and observation.

 

I appreciate the vote of confidence. It can honestly be hard to resist the urge to try to make more. But in the end I don’t see many people at any income level that really appear completely content with their income/investments/net worth. What’s the rate of return or nest egg value that lets one know when to let off the gas? The human rat race seems to be pretty out of control. Anecdotally, I’d say that those with less are more likely to actually feel (or present themselves) content. If Warren Buffett feels the need to keep generating and maximizing cash flow…well…I’m not entirely sure what to do with that.

 

Astute observations and thoughts. I’m also on this vision quest as well, “how much is enough”. Often people try to boil this down to a single number. For me, that has not worked. So now the question is shifting from “how much” to “what”. I’ll let you know when I reach this moment of clarity. Don’t hold your breath.

 

Great observation, enjoy that family! This last year has been a tough one for me and everything that's happened has just reiterated to me that I need to enjoy life while I can, time is precious. One of the "ventures" I mentioned above is more about pursuing an avenue that I believe will really help others, which is a passion of mine. If I can monetize it, even better....maybe it will allow me to drop more trips and spend more time with family and/or helping others. Everything else I do to "get ahead" financially, is more about providing some side/passive income should I lose my medical. Plus I really don't want to be doing this gig until I'm 65, so it would be great to have (mostly) passive income built up so that I can easily retire early. Obviously, you have to find that balance that ensures you're not missing out on the moment!

 

The slow and steady approach of investing in retirement accounts will create a big pile of money. The beauty of a venture into real estate and to a lesser extent, dividend stocks is that it creates income today that buys back time. You don't have to wait for 59 1/2 to start reaping the benefits. Knowing the bills are (partially) paid from a side hustle before you even go to work for the month is much more liberating than having a fat emergency fund.

I spent a majority of 2021 on the vision quest you mentioned and came up with a couple revelations that directed some significant actions. Estimating the longevity of a pile of cash comes with lots of uncertainty. Predicting future rates of return, inflation and calculating a draw down rate you won't outlive is stressful and leads in some cases to overaccumulation. How much becomes an ever-increasing number to deal with the range of uncertainty. Turning that pile of cash into a predictable income stream really helps shift the mind from "how much" to "what".

 

I’ve had 2, sold both.
First was a margarita recipe my wife and I developed, brought to market and sold to a small restaurant chain.
Second was a small car show (Caffeine and Octane) that turned into the biggest monthly auto gathering in the nation. Sold it to Cox Communications.

Not sure what the next one will be.

 

I don't think so

My strategy too. Unfortunately or fortunately (depending how you look at it) the check of the month club for me has made me sort of lazy. I contribute max to my stuff here at DAL. The matching is good (could be better though - TED74 for negotiating committee BTW!). I should probably be rolling over that check of the month into some more aggressive investments as play with $$, rather I use it for my "hobbies" all of which are tremendous wastes but provide us with so much well needed relief. Hard to put a $$$ value on that. I'll reconcile that opportunity cost any day.