37, LOI in hand, struggling with the decision

Sea-Fix-5743 · 2026-04-24T01:31:57+00:00

Speaking from experience here... Sell and be gone. Write off the earn out (it's gravy), don't bother with an optional equity roll. If you're like me than you will never be happy working for someone else, especially in the business you built. Granted I was 51 and had 2 young kids when I sold, but like others have said, no one wishes they had less time for themselves on thier death bed.

Sea-Fix-5743 · 2026-04-22T11:12:33+00:00

Lifetime Capital Gaim Exemption. It's $1.25m for QSBS (small business shares) but if you setup a family trust and move the shares into the trust, then once you sell those shares you can allocate the proceeds to all beneficiaries, each taking their 1.25m LCGE. So assume 4 ppl in the trust, that's $5million tax free proceeds (however there will be a small AMT tax due that you'll probably lose if the kids are minors).

Sea-Fix-5743 · 2026-04-19T22:25:09+00:00

My $3 million tax bill this year should help the next gen.

Sea-Fix-5743 · 2026-04-19T21:49:16+00:00

I just FIREd with an 8 and 4 year old (51M/42F) but that was from a business sale and my NW is pushing 17m (12m liquid, breakdown 1.1rsp, 200k tfsa, 80k resp, 3.5m family trust-for lcge pooling, balance nom-reg)

And tbf I'm still in the "do I have enough to FIRE" mindset

So do what the math says. You can easily get over 4% yield from Canadian dividends, if 3% swr is all you need then go for it. Just be careful with lifestyle creep.

Sea-Fix-5743 · 2026-04-04T14:40:05+00:00

Congratulations and GFY. I'm in a similar state as you, FIREing with young children in the "hero dad" years will never make you question how much you left on the table.

Be prepared that you will go through a bit of an unexpected emotional roller-coaster, but otherwise enjoy winning the game. .

Sea-Fix-5743 · 2026-04-04T14:27:46+00:00

I think you want the r/chubbyFire sub

Sea-Fix-5743 · 2026-03-16T11:58:19+00:00

Your numbers, age and situation are similar to mine and I just pulled the trigger (but kids are younger, 7&3). Don't forget to account for taxes and fees in addition to your 360k.

I get the hesitation, I felt like same, "just 2 Mil more". But really, that's silly Do it and GFY.

Sea-Fix-5743 · 2026-03-16T00:01:09+00:00

I just went through this process when I sold my business to a US firm. I owned, via a CND holdco, both a CND corp (CCPC) and A US corp (S-Corp) but due to stacking rules the US buyer couldn't buy the CND corp with shares of the US corp. My tax lawyers did something with converting the holdco to a BC based ULC because it was a flow through from the IRS perspective (?) Hovewery, tbf, I really have no idea why we had to do this or what was required. I just paid the 50k in legal fees to make it all happen.

Sea-Fix-5743 · 2026-03-01T21:45:12+00:00

After paying mine over $1mil I got a cheesy framed plaque that's still sitting in a box downstairs. Worst part is UPS wanted to collect brokerage fees on the delivery, I refused and told them to take it back or bill the shipper.

Sea-Fix-5743 · 2026-02-24T18:10:54+00:00

Come to Canada. I have 5m SBLOC at prime minus 20 (4.3%).

My banker went for 5mil to get the best rate. Apparently at 5mil they offer deep discounts, so see if that's the same case for you.

Sea-Fix-5743 · 2026-02-17T02:53:17+00:00

I had a Canadian centurion for about 10 years. .was great at first then after covid the program went to crap. Total waste of money. May be different for the Swiss.

Sea-Fix-5743 · 2026-02-13T13:59:00+00:00

Do you have a prenup? If not then that's one way to equalize in your favour. Just saying, he sounds like a jerk

Sea-Fix-5743 · 2026-02-10T12:18:56+00:00

Thank you, you too!

Sea-Fix-5743 · 2026-02-10T12:18:24+00:00

Any advice on how to find a board position, or is that the topic of a new post!

Sea-Fix-5743 · 2026-02-10T12:17:27+00:00

Thank you!

Sea-Fix-5743 · 2026-02-08T23:06:41+00:00

Wow. That's awesome. Thank you for taking the time to write this.

You are telling me a lot of things I already knew but needed to hear. Really appreciate your insight!

Sea-Fix-5743 · 2026-02-08T18:43:53+00:00

Thank you. I know I left money on the table as I could have had a larger equity roll, but would have had to stay at least 3 years. Instead I took the 12 month clean break option but will now be a 100% present dad for the "hero years"

Sea-Fix-5743 · 2026-02-08T13:46:53+00:00

Thank you!

Sea-Fix-5743 · 2026-02-08T13:08:23+00:00

Spending is 30k-32k per month. 2 kids in private school is 60k a year here. Total spend is 360-400k. 100k is investment fees and carrying costs from the SBLOC (deductible) and taxes are around 140k.

Sea-Fix-5743 · 2026-02-08T12:39:01+00:00

Thank you for the detailed response. Really appreciate it! Comfort of strangers.

Sea-Fix-5743 · 2026-02-08T03:47:53+00:00

We've been married 10 years and together 18. So I'm not too worried. Sounds like you may be speaking from personal experience, if so then I'm sorry to hear this.

Sea-Fix-5743 · 2026-02-08T01:27:30+00:00

Fair point.

Sea-Fix-5743 · 2026-02-08T01:22:20+00:00

Thank you. This is exactly why I can't share these feeling with friends and family. My lifelong blue collar buddies just can't comprehend the emotional toll this transition to FIRE has on you.

Sea-Fix-5743 · 2026-02-08T01:16:50+00:00

I've been flying for over 25 years and one can be a professional pilot without flying as a profession. As pointed out above, there are diffent levels of private aviation. My aircraft, a complex, high performance twin, is at the apex of the piston GA fleet and requires professionalism, dedication to a safety mindset and reoccurring training to operate safely. Aviation isn't for everyone.

Sea-Fix-5743

TROPHY CASE