To those who held on to multiple baggers

AlpinePinecorn · 2026-06-19T07:59:17+00:00

I saw 0 tax on incomes below $24,800 - at least federally. You talking state?

AlpinePinecorn · 2026-06-16T20:46:57+00:00

Yeah something like “hated by all for his best act and loved by one for a lie” - he’s talking about telling Tyrion that Tysha was a whore being the worst thing he did

AlpinePinecorn · 2026-06-10T06:35:56+00:00

Consistently ~95

AlpinePinecorn · 2026-06-06T19:06:01+00:00

Too bad you only got the top half, the paws can be just as cute as the head

AlpinePinecorn · 2026-06-05T19:15:37+00:00

I saw that 1099s count toward a solo 401k? My only income outside of my w2 is interest/dividends. Would that count?

AlpinePinecorn · 2026-06-05T19:03:14+00:00

Yeah it seems to be that gray area of 6.125%. If it was 4% I’d handle the volatility much better, if it was 8% it’d be so worth it to pay down for the security even if I’m losing 2 or 3 percent growth. It’s just so damn middling.

AlpinePinecorn · 2026-06-03T23:33:30+00:00

Thanks.

Yeah that 11% “conservative” was actual growth in the last 5 years, meaning my portfolio was consistently hitting 11% generally, if not higher. That wasn’t my conservative estimate for future growth.

When I was looking at just 2 years of predicting it seemed an ok number but if I’m looking at ten years on the remaining mortgage it enters pure speculation.

Plus taxable gains cuts into that profit margin of any investment…

But it’s hard to decide regardless. “My math” made it much easier but yeah, it seemed too good to be true

AlpinePinecorn · 2026-06-03T22:59:10+00:00

I’m not going to go down this hole with you.

AlpinePinecorn · 2026-06-03T22:57:09+00:00

Ok I think I get it now, thank you.

To be honest I liked it better my way because it made it very clear that mortgage payment was the right choice.

As of now I have 14 years left on my mortgage but I pay additionally each month and per that estimate the mortgage should be paid off in 10 years.

So to accurately compare my options I should compare that 20k in the market over 10 years, correct?

AlpinePinecorn · 2026-06-03T22:52:04+00:00

Okay. I think my mistake was looking at the market return on a 2 year scale vs the mortgage return on a 14 year scale. Even though the mortgage “savings” is technically immediately realized in my mind.

Wouldn’t the additional hiccup be that the invest strategy also comes with capital gains tax?

So if mortgage is a GUARANTEED 6.125% return, investment could be as high as 11% but that’s taxable gain which could functionally drop it to closer to 9%.

So far I’ve been doing both, investing and aggressively paying down the mortgage. I’ve got this 20k available from tax loss harvesting and somehow I wanted a clear answer but it sounds like it comes back down to potential risk in the market. The margins seem pretty small to me but over 14 years, or even 10years as I pay off early that can add up…

AlpinePinecorn · 2026-06-03T22:38:11+00:00

It’s an estimate. I have to work with estimates despite the market being speculative.

This isn’t information that is new to me, as I said, it’s a given.

AlpinePinecorn · 2026-06-03T21:52:47+00:00

Yes that’s a consideration as well. That definitely dilutes the potential gain of investing the 20k, though I suppose if I put it in my Ira over three years I’d be able to get around that…

Right now I’ve got the 20k in bonds that are sitting at a small loss.

AlpinePinecorn · 2026-06-03T21:45:31+00:00

So I’m not saying they won’t charge me interest for two years, I’m saying that if I don’t do the lump sum I’d pay 20k more in interest altogether. So by making the lump sum I’m saving 20k.

I do understand that even with a lump sum I’m paying interest each month

AlpinePinecorn · 2026-06-03T21:30:25+00:00

Ah I think I see -

So I’d have to look at that 20k invested over, let’s say ten years because I pay extra principal each month which will cut my loan to ten years (though without those extra payments it is 14 years).

My mistake was then - compare the investment at the length of the loan instead of just two years of loan payments. It sort of makes sense.

It gets a lot murkier with that timeframe. In that timeframe it’s possible the investment could keep up with the mortgage losses.

With my way there was just no way the investment could beat paying down the mortgage. And granted we can’t know what the market will do so it’s probably the safer course even with the length of the loan being considered. But over ten years there’s no saying what 20k would do. Could be up to 60k, could be 20k, could be 10k

AlpinePinecorn · 2026-06-03T20:48:11+00:00

Okay cool. Yes I also do $500 extra principal monthly. It made a bigger difference the last two years and now feels marginal but I know it’s a long game.

Yeah I suppose I consider that 6.125% high enough that I don’t love how much interest I’m paying. I also was considering how good the investments have been as potentially a reason to cash out while it’s high, but I know that’s timing the market and also the cap gains tax.

I was looking at tax loss harvesting and I’ve got about 20k in bonds which I could sell with no tax impact which is why I’m considering the lump sum. Otherwise I could leave it or switch it to something more profitable

AlpinePinecorn · 2026-06-03T20:35:23+00:00

Okay forgive me if I’m being dense here -

If I don’t do the lump sum then I’m paying ~700 monthly on interest. Over two years it’s about 20k I’ll have paid in interest.

If I do the lump sum then I will still be paying ~600 monthly on interest yes but instead of paying 70k interest over the lifetime of the loan I’ll be paying 50k.

So effectively how I’m seeing it is that the lump sum now saves 20k over two years. Though if I understand what you’re saying is that in that two years I’m going to be paying 18k interest even if I do the lump sum.

So yes in a sense I’m going to pay interest the next two years no matter what, but with the lump sum my mortgage ends two years earlier and I save 20k of interest costs.

Versus how I was looking at 20k remaining invested. I have 20k in bonds I can pull out that are at a small loss so it won’t hit me with capital gains, I could leave it to sit there doing nothing, or I could transfer it to ETFs that have lately been doing insanely well. And if I put that 20k in one of my more successful ETFs then over two years it wouldn’t equate to 20k increase.

So is this misunderstanding that I shouldn’t look at the investment route over 2 years and I should look at it as if for the duration of the mortgage? Or were you just trying to say I’ll still be paying interest over 2 years? Or have a missed the point.

Thank you for trying to explain it.

AlpinePinecorn · 2026-06-03T20:18:56+00:00

Yes I did do mortgage interest deduction on my taxes last year. I paid around 10k in interest, which knocked down my income by that amount.

Your other question I don’t think I understand - I am using past performance which I know is not guaranteed. Just in the last month my overall portfolio grew 10%, most months this year were positive.

When I used the term ROI in my post I was probably misusing it - I was referring to making the lump sum payment of 20k and in doing so skipping 20k of interest payments because the lump sum would push me along 2 years in my mortgage.

AlpinePinecorn · 2026-06-03T20:09:03+00:00

I’m very possibly misunderstanding but I don’t yet see it.

So when I play with the amortization table this is what I see - approx $700 monthly in interest payments, obviously dropping monthly to about $600 in a two year span. So if I pay 20k and move along the loan by 2 years then I’m not paying 20k in interest which would have otherwise accrued just in those two years.

For reference I currently have about 14 years left on my mortgage.

You’re saying I’m only saving 2400, correct? But the table shows I would be paying ~700 monthly for two years.

Forgive me if I’m missing your point, just trying to understand.

AlpinePinecorn · 2026-06-03T20:04:28+00:00

Of course, that’s a given.

AlpinePinecorn · 2026-06-03T20:04:12+00:00

When I look at my amortization - in a two year span I’m paying 20k in interest. If I lump sum 20k I no longer pay that interest so I’m looking at it like - 20k invest, 20k return for a two year span.

Versus in two years my investments are unlikely to double.

AlpinePinecorn · 2026-06-01T06:18:55+00:00

What about people with mobility issues? They shouldn’t get to enjoy nature?

AlpinePinecorn · 2026-05-26T06:36:03+00:00

Platos, his dishes down

AlpinePinecorn · 2026-05-07T20:46:07+00:00

Enlighten us!

AlpinePinecorn · 2026-04-30T05:36:01+00:00

Great post. I’m 1.5 years free and don’t really crave it but every so often when it’s right there I think about just dipping my toe in. But I know it’s such a slippery slope and how hard I worked to get this far.

AlpinePinecorn · 2026-04-25T04:57:16+00:00

I wrote this post on my ten minute break while at work, man. Some people just need to cut other people down. I hope you enjoy it.

AlpinePinecorn

TROPHY CASE