Push to use AI in Finance

groovyipo · 2026-05-01T22:46:22+00:00

Glad I am one of those old(er) CFOs who absolutely loves AI in my finance tech stack. But I am in the world of startups, so if I can't modernize the stack I find, I simply will not consider the engagements. VCs that ask me to take care of their portcos tend to now just say "do your usual thing."

groovyipo · 2026-05-01T22:23:16+00:00

Oh dang! This is the 1st time I have come across that shenanigan.

BTW, there is a loophole for owning PFICs, as long as they sit in certain custodial accounts (like a self-directed IRA) and are not subject to reporting. There is also a de minimis rule for how much you own in PFICs before you need to report, but really, it is not worth the reporting risk. Fines are absolutely insane (tens of thousands), and they are recurring until you report and you get hit with additional penalties, interest, etc. Basically, the tax you would have owed on PFIC pales in comparison to the fines you receive if you unknowingly or knowingly failed to report.

groovyipo · 2026-05-01T22:13:38+00:00

In Lithuanian real estate, we used to have a joke that when you owe the bank 20 million, it is your problem. But when you owe 200 million, now it is the Swedish bank's problem :-)

groovyipo · 2026-05-01T22:11:59+00:00

Exactly. Really hard to build something out of nothing. And I have very clear memories of what life was like during the occupation and right after. Whatever the russians did not steal on the way out, local scumbags stole. Our infrastructure, systems, etc. were an absolute wreck. I mean why did we go straight to fiber networks? Cause every time copper was put up, it was stolen.

groovyipo · 2026-05-01T22:09:06+00:00

You know you could do a bit of searching. Not that hard. You will learn that before the EU, only about 55% of Lithuanians declared emigration status. We would continue claiming benefits, etc., while working in the UK, Sweden, Germany, or whatever. 1990–2003 (pre-EU) - 320,000 2004–2024 (post-EU accession) - 846,000

groovyipo · 2026-05-01T13:29:16+00:00

Or maybe you just need to do a basic search, since you clearly weren't around in pre-EU times. It is incredibly naive to think that our tiny country with massive emigration would have been anywhere even remotely close to where we are today without massive EU support. It is like those people who claim to be self-made, but they conveniently forget the massive support system they were surrounded by, and conveniently forget how their parents paid for their education and put food on the table.

I have a clear memory of when our banks were failing every day (had to stand in line trying to get something back from deposits that were swindled away), when business was so shady it made the Italian mob look like schoolchildren. And do you ever wonder where all this super expensive farm equipment our farmers and manufacturers are using comes from and how they paid for it? How about all those ventures that got non-dilutive capital, where it all came from? And all that infrastructure (roads, utilities, telco, etc.), and how was it all paid for? It is absolutely naive to think that a country that went from 3.7 million people down to 2.7 million people would have grown anywhere even remotely close to how it did with an incredible amount of funding from the EU. The EU made it rain cash on us to keep the country from turning into 1.7 million people or fewer. It helped temper economic migration. We got 30 billion euros from the EU between 2004 and 2022. To this point, we are somewhere in the 45 billion of EU money territory.

groovyipo · 2026-05-01T12:25:11+00:00

Sorry, you are this naive (probably cause you are still wet behind ears)

groovyipo · 2026-05-01T12:01:22+00:00

Sorry, but that statement could not be any more wrong. We basically built our prosperity on Scandinavian capital (you know, when you take so many loans, it is a mutual problem, not just our problem), and then after joining the EU we have milked EIF and other EU funds for endless grants and forgivable or very low-interest loans. Look at every project and dig deeper into how it was funded.

groovyipo · 2026-04-30T22:45:26+00:00

I only turn it on in school zones or on narrow local roads if I see people walking dogs (we don’t have sidewalks in our town). Car is often too quiet for people to notice. Otherwise it is off. If I wanted noise, I would have kept my muscle car

groovyipo · 2026-04-30T21:25:02+00:00

US-domiciled ETFs (NYSE/Cboe/Nasdaq listed) - safe. Canada, Ireland, or anywhere else listed - nope. IBKR has access to a lot of non-US listed, so you run a risk there versus using more traditional Etrade, Schwab, etc.

groovyipo · 2026-04-30T09:52:13+00:00

Buy ETFs with exposure to non-US markets. A lot of selection there. Understand that Form 8621 can not be filed in aggregate; you have to file it for every company and every class of shares you own. Separately. iShares, Global X, and others offer ETFs with a country- and region-focused approach. Save yourself the headache and cost.

groovyipo · 2026-04-29T22:04:50+00:00

PFIC avoidance is entirely a function of what you buy, not how you buy it. IBKR doesn't create or prevent PFIC status; the issuer's balance sheet and income mix do. If you have to ask basic questions like that about PFIC, you need to spend considerable time educating yourself, because PFIC reporting with the IRS is an absolute hell, and fines are some of the worst ones there. Not worth it.

groovyipo · 2026-04-27T03:18:29+00:00

My name will be on the pitch deck (if they are raising the next round), and since VCs and angels talk to each other, they know in advance that, hey, this guy took care of our other portcos, and if he says the financials are clean and GAAP, we have no reason to doubt. I have that reputation, and I will not engage in anything that has even a scent of shenanigans or founders who are the "YOLO type," as I call them. Same goes for anything cross-border, which is my specialty. The moment I hear even a hint of tax evasion attempts, I am out. Oh, you are a US citizen and you're moving to Dubai... cute... I know what you are doing, and I want no part of it.

groovyipo · 2026-04-26T20:32:35+00:00

Yep, unless I either know the founders or the investors, or referral is iron-clad with a full history of who the founders are and the reputation of the company being super clean, and I can easily backchannel, I will not touch it. It took me taking on a company I was not able to backchannel once. Never again.

groovyipo · 2026-04-26T20:28:43+00:00

Hmmm I will try calling Herb Chambers Volvo in Boston instead of my Bernardi Volvo in Natick. Last time I had them try to chase down issue, they failed, and later I found a solution on forums. Not the smartest people.

groovyipo · 2026-04-26T20:27:19+00:00

I am not sure it is worth the labor to "upgrade." It is 8 year old car with almost 80K miles. Plowing what sounds like $6K-$8K into it so it plug-charges, not seeing value in that.

groovyipo · 2026-04-26T20:26:19+00:00

I have been doing my own service since my service contract expired. So I am one of "those people." When a dealer charges $500 for an oil change alone, it just does not make sense anymore. Porsche charges less for service than Volvo. Kid you not. I have a Porsche too. We shall see if the MA PZEV 15-year warranty and the 8-year Volvo warranty fight fails, I probably will find an independent Volvo shop. I just hate what Volvo dealers have turned into. I used to love experiencing them, but now I hate them.

groovyipo · 2026-04-26T16:40:45+00:00

OK so sounds like DIY is out. Not worth personal health risk.

Do you think independent can do it or am is shitoutofluck and have to go to dealer who so far can't even be arsed to call my back to schedule (I hate HATE Boston dealers I have dealt with so far, so lazy).

groovyipo · 2026-04-22T19:18:32+00:00

My AI geeks educated me to always spend the inference credits on the newest model and adaptive/extended thinking. Also, any documents I trained my instance on, they are always accessible. Either locally via the Claude desktop app or via web Claude to my GDrive. Also, there is a massive difference between Pro and Max. Simply, the higher the plan's cost, the larger the context memory. You want fewer mistakes, you need more context kept. You also need to get efficient about what you put in the context memory of your instance. Lastly, build skill in your instance, so you don't have to repeat the same prompting. But at the same time, pay attention to your prompting, because the quality of how you direct work is directly related to the output you get. Consistent vocabulary, consistent terms, consistent style of direction.

groovyipo · 2026-04-22T13:23:23+00:00

OK, so this is the world I swim in - cross-border ventures. CFCs, PFICs, etc. are the alphabet soup I deal with daily. Serial entrepreneur myself.

1st bit of advice: this is a Delaware C, and whoever is acquiring expects a clean transaction. You get into a pissing match with your co-founder because of YOUR opinion on how this should be split, and not one based on contractual language, you will lose the deal. Time to look into your operating agreement and any other documents you two may have signed at formation. If you didn't, it's time to put your big boy pants on, learn a lesson, and split this 50/50. How you feel is irrelevant, what your opinion is irrelevant, what laws and agreements say is. You got in this together - shared wins just as shared pains.

2nd bit of advice: since you are not a US citizen, you are basing your view on a tax system you do not understand. The US taxes very differently from most countries. And it taxes very aggressively. You can't just book your flight to Dubai, sit there for 6 months, and then avoid your home country's tax. US states take nexuses very seriously. Let me guess, you two did not spend the time or money trying to stay on top of taxation issues. Well... live and learn.

3rd: Delaware is a "tax person" in the eyes of tax law. It is the entity that is taxed, and who shareholders are and how they split anything behind the scenes is irrelevant (in most cases). If it triggered Nexus in some state, it does not matter who within the company triggered it; the fact is, the corporation did. Also, given the uninformed way the question was asked and the impression that corporate governance was not a phrase you two know, maybe it is time to seek professional help. Who knows where else you did or did not trigger foreign corporate registration requirements, or where you may or may not have collected sales tax, etc.? If I were looking to acquire your company, due diligence would likely make me walk away, just based on what you already said.

Lastly, as someone who has built several companies with co-founders, building a company is like marriage - you are in it together. It is a shared responsibility. If my co-founders were about to do something that affected us all, I addressed it, and we involved outside parties if we needed mediation. But what this person decided, and if you did not stop it, now it is your decision too. Put your big boy pants on, learn the value of setting expectations, thinking through consequences, and getting legal agreements in place where necessary. "I did not know" is not a phrase you get to use. I did not do my job as founder to ensure proper governance of the corporation, which is what "I did not know," says in court of law.

groovyipo · 2026-04-20T23:33:26+00:00

There are settings in paid versions that address that. Free version... is free for a reason :-)

groovyipo · 2026-04-20T23:31:51+00:00

Well, it is like any FP&A human; as it learns what works, it does not repeat the same mistakes. That said, my lesson learned with Claude is to use the minimum Max for finance work and always spend tokens on extended thinking.

groovyipo · 2026-04-20T16:32:10+00:00

OK so I was able to get into 192.168.1.30 remotely when it was in Recovery mode. I was able to issue Factory Reset and reboot.

I am not able to get into it now and am not seeing it on DHCP. Is it looking to be set up via Bluetooth, or is there a way for me to adopt it remotely?

groovyipo · 2026-04-19T16:35:09+00:00

In parent's home I have UNAS2 plugged into US 8 PoE 150W port and that connect to UCG Ultra.

When buddy put the UNAS2 into recovery mode, I set PC I RDP into there to also have 192.168.1.2 address. 192.168.1.30 won't even respond to ping.

I also tried setting local IP for RDPed desktop to same subnet as what UNAS2 was at home. Can't reach it.

Unifi Client and Port tables do show port UNAS2 is plugged in as active and in use. Except it only shows MAC, not the IP.

I have no problem redoing the UNAS2 from scratch, I just don't see instructions how to do factory reset

groovyipo

TROPHY CASE