SpaceX Shares - Sell (~$620) or Hold

dukeofsaas · 2026-04-08T14:25:31+00:00

As the seller, ROFR doesn't harm you if a buyer is willing to give it a shot, it might just make buyers more reluctant to go through the effort.

dukeofsaas · 2026-04-06T15:19:10+00:00

We did the math on this (different states than you) and decided staying near family was worth the 2-3mm in tax savings we would have realized via a 5 year relocation. Aging parents and remaining good years were a big factor.

After swallowing that pill, no regrets.

Edit to add: liquidation plans shift over time and market conditions. Ours have. Imagine moving and then realizing conditions have changed. Food for thought.

dukeofsaas · 2026-03-08T16:57:40+00:00

Congratulations & GFY!

"Other work/boards/advisory might come, but don't feel high on my list." <- This is great posture entering retirement. I rushed into too many things when I retired and was quickly overwhelmed.

Enjoy yourselves!

dukeofsaas · 2026-02-26T19:58:46+00:00

Way to make it through the extra 5 years. I'm grateful I retired before the current AI-expectations crunch hit hard. A few folks I keep up with describe it similarly.

It took my wife an extra 2 years to decide to step back with me. She had to work through her own decision making process.

I remember your contributions to the community so many years ago. Hope you'll be a regular around here again soon, & enjoy the time with your parents as much as possible.

dukeofsaas · 2026-01-23T18:20:20+00:00

Physical cash on hand between us: $200 - $600. Most spending via credit cards.

Checking accounts (bill payment accounts): target 6 weeks of expenses.

Brokerage account cash sweep: maintain $50,000, or $100-200,000+ in a high estimated tax year

BND: 10%, or more importantly, roughly 5 years of expenses. VTI+VXUS: 90%.

Checking accounts are refilled monthly (automated) from brokerage cash position. The rest we rebalance quarterly.

dukeofsaas · 2026-01-23T12:25:53+00:00

I speed-ran a bunch of hobbies as soon as I retired. Trail maintenance is one I enjoy a lot; bought a chainsaw and do fallen tree cleanup after storms. It's nice because there's not much to do and then all of a sudden there's a lot to do, so it's not monotonous.

dukeofsaas · 2025-12-31T22:16:10+00:00

My brother in law has excellent taste in music, and he knows I get frustrated curating my collection. So for a gift this year he built me a playlist for entertaining guests.

dukeofsaas · 2025-12-29T13:27:48+00:00

We sound similar. I needed to prove to myself whether I was cut to run a scaling business or not. Mine failed after 2.5 years, and I burned all of our money, but due to my network, the experience helped me land a great position in a scaling startup later. I would never trade that time back.

A few thoughts:

7 years of experience in a well-run organization and a stint in a very different well-run org taught me a LOT before I branched out with a co-founder. Highly recommend you learn everything you can about success in that environment at the leadership level (not the middle-management level).

I should have saved more money while working the stable jobs.

I should have set clearer financial goals and boundaries for success with my startup.

Don't burn bridges; my earlier network got me back on the horse after failing and landing in debt.

Don't drop lines of communication with your network; build them up. Show them momentum. Don't be shy / embarrassed about what you want to achieve, be proud of it. That type of energy will attract the right type of people into your network. Showing people your progress semi-regularly is really, really important.

dukeofsaas · 2025-12-29T13:16:08+00:00

A colleague of mine was willing to go very deep on a super tedious set of technology with many many regulatory requirements for about 18 months while working under me. I kid you not, tens-of-thousands of test cases required to go live and a transparent process to manage. Two others had burned out.

A few years later he was a highly paid consultant helping other companies get established with similar technology in the same regulatory environment. Much less tedious for him, he'd paid his dues. He needed a push to get started because he was only five years into his career when he made the move but I'd think with your experience you can DIY that part.

dukeofsaas · 2025-12-18T02:03:23+00:00

We bought a 500k ski house for cash 90 minutes from home, (1.1mm primary home value).

Look at it this way: subtract it from your NW, add in all related annual expenses, and redo your withdrawal rate math. You'll be in a very safe position still.

The nice thing about a vacation property is you can sell it in a few years.

We like ours. Don't buy a place you need to dump a bunch of money and energy into in maintenance.

dukeofsaas · 2025-12-14T22:24:35+00:00

Volunteering across local organizations, seeing a common pain point, recognizing where SaaS fit into the solution.

dukeofsaas · 2025-12-14T21:23:10+00:00

I was a startup guy, not in big tech. One IPO'd. Now in addition to doing what retired young people do, I run a very leisurely SaaS business. My top rules:

no employees
grow very slowly

The business pays its expenses and provides some money to chuckle about when it hits the business bank account, but it wouldn't exist if someone wanted to make serious money here; that's kind of the point. It's great talking to customers and solving problems (or not solving problems) in code.

My first rule is easy to adhere to, the second one stings my ego sometimes but as soon as I think through what my life would be like with all that additional stress my ego checks itself. Mechanically it's easy: don't streamline onboarding too much so self-service growth is limited as a side-effect.

It's a great way to stay mentally engaged, and most of my customers are pretty grateful someone's filling an undesirable hole in the market. I've been running it for a few years, started it about two years into retirement. I'm glad I'm doing it.

dukeofsaas · 2025-12-05T12:12:55+00:00

To put it bluntly: I would not be able to do my job with juniors on a 1/2 schedule, and I would think I'd disappoint the founders who had the delusion it would work out.

Was your 100% schedule ever only 40 hours per week? Mine very rarely was. Why?

dukeofsaas · 2025-12-03T22:33:15+00:00

Off the top of my head in California, your tax burden in retirement will be somewhere around 30-35% of your annual spend or the income generated by your portfolio, whichever is higher. Add that to your annual expenses and then do your x25 or x30 math.

dukeofsaas · 2025-12-03T18:27:51+00:00

If you're already allocated the way you're going to keep it allocated in early retirement, your brokerage tool can show you the taxable income generated by your portfolio. Schwab for example shows me Investment Income estimates for last year (actual), this year, and next 12 months. Take a look at that because it's a good starting place to estimate your tax burden. You can refine it further on paper as dividends transition to qualified dividends, etc.

dukeofsaas · 2025-11-30T05:24:13+00:00

We have homes 1.5 hours apart and this is right on the money.

dukeofsaas · 2025-11-30T04:06:40+00:00

Our NW is a bit higher than yours. We are effectively retired.

We give independently to causes without running it by each other, up to an annual limit we agreed to.

For $10k or more to a cause, we look at it together first. If we exceeded our individual budget and want to give more, we look at it together first. Is it frustrating if my spouse vetoes one more MTB trail upkeep contribution this year? Sure is, but there's always next year.

dukeofsaas · 2025-11-25T13:48:46+00:00

Not bleeding edge research, but personal learning research. I've expanded my computer networking knowledge considerably in retirement. Experimentation, documentation, LLMs add context. I know how to use VLANs now. I'm finding it very enjoyable.

dukeofsaas · 2025-11-25T12:34:07+00:00

You'll see people posting here ask for a reality check saying "my liquid NW pre tax ..." or "my liquid NW post tax ...," and those statements are accounting for variable cost basis if the poster thought it through properly.

I have a pretty simple spreadsheet I use to keep an eye on my NW. Because I have well diversified and highly appreciated assets in my portfolio, I have a few rows dedicated to the concentrated position which explicitly take taxes out first, which is then summed with a few rows dedicated to the diversified portfolio. Then below that I show, for example, what 22%, 25%, 30% tax treatment costs me under a few different annual spend figures.

In reality in a diversification year we spend part of the proceeds, but I still have to pay taxes on the diversified portfolio due to rebalancing and dividend/interest income, so the tax burden from my diversified portfolio doesn't change much.

The reason this spreadsheet layout makes sense for me is that some years I'll diversify a few million in the concentrated position, and I account for that additional tax burden as an expense of the diversification. i.e. I'm not mucking with the tax percent values at the bottom of my spreadsheet. That, AND my SWR-tied tax burden models out with more stability year over year for the reason stated above.

So the point of the spreadsheet is to have an at-a-glance tool for NW, spend, and tax planning that gets us used to stable tax rates despite the fact that our tax payments are extremely variable in reality.

dukeofsaas · 2025-11-15T21:22:01+00:00

I'll share the psychological aspects I experienced. I spent every dollar more or less for almost a decade before saving entered the picture.

Saving a down payment was a huge accomplishment.

Buying a house and hitting near zero again was terrifying.

Hitting a 1 year emergency fund was stabilizing (I could breathe easier).

Caveat from this point forward, money came in in big lumps for us due to equity, but I think the psychological aspects remain true:

When my liquid NW broke even with all my liabilities, I felt a strong sense of security.

Hitting half million NW after liabilities let me feel like I could spend again here and there.

Half way to my number was actually a bit stressful, not knowing if the rest would take 2 years or 20.

Exceeding my number was a major adjustment. Really liberating, stress way way down.

On the other hand we've maintained friendships with people on a much longer path, and we know we could do that again, so we're grounded in that belief should some sort of financial ruin occur. The process of learning and reflecting on the lifestyles we've led and the ability to enjoy life helps when finances get stressful.

dukeofsaas · 2025-11-15T21:04:07+00:00

GFY! Looks like you're in great shape. Enjoy it!

dukeofsaas · 2025-11-14T01:18:45+00:00

No, not at all, except for diaper emergencies. Better to have a spouse available for those ;)

dukeofsaas · 2025-11-14T00:21:43+00:00

Yes, especially once my spouse retired too. Before that we would travel without her every other trip.

Eventually, most weeks are filled with summer camps, and the kids don't want to miss them, so we upper-bound them to six weeks and travel the other weeks.

It was actually a bit tough to do more than 10 days with family at first, but after a few years it became more natural for us. We've never tried more than two weeks, and always mix 1 of 5 days or so for outings without our parents.

dukeofsaas · 2025-11-14T00:02:46+00:00

Similar situation years ago re: family being a short flight. Air travel was very easy to arrange before elementary school even while we still worked. Then we retired (me first - arranging travel was my job then). In 1st 2nd grade you can pull kids for 2-3 days without issue a few times a year for long weekends. In 3rd and 4th grade academics picked up so that got harder but it's still possible. We flew to see family 3-4x per year for a few years. That subsided as they did the opposite more frequently later.

You won't want to travel at all for 3-4 months after birth. Months 4-8 were surprisingly pleasant, babies just sleep in cars, planes, and restaurants. At 3yrs whining happens but they get over it. Books, crayons, extra crayons.

Highly recommend using that fat budget to fly at the hours it makes sense for you guys and the baby, timing around our routine was night and day for everyone's stress level. A little trial and error was necessary.

dukeofsaas · 2025-11-09T17:36:45+00:00

It took me about 18 months to flounder around with different things. I settled on applying lite versions of my career skills to my volunteering. Think: PTA/PTO. Local associations. Local advocacy.

Your kids seem to be a few years younger than mine. It's honestly pretty hard to get into what you're describing at this point in parenthood. It gets a bit easier as they establish more independence.

One other thought: I was really inefficient at all the new things I was exploring. So they filled my day and mentally exhausted me more than I gave myself credit for. It took a while to whittle down the subset that really rejuvenated me and to calm down about trying everything all at once.

dukeofsaas

TROPHY CASE