Nick Chertock

Exploring the golf improvement process. Open Forum cofounder. Tax Firm Owner (CPA). dad of 3 vb players. startups. side hustles. equity comp tax expert

[Nick Chertock @golfprogress]

@ryanmouquegolf People have experiences after commenting that shift their relationship with social media toward quiet lurking…years ago lots of people would comment but if they felt attacked they would usually stop

[Nick Chertock @golfprogress]

@DocBrownLloyd 88mph…one point twenty one gigawatts.

[Nick Chertock @golfprogress]

@bsuecannon What I told Claude on 10/16 when I wanted to revisit my top goals for Q4 which I had forgotten

[Nick Chertock @golfprogress]

When we were in school, no one would ever turn in an assignment a week before the deadline… you would turn in that shit at the last possible second. If you go into Tax accounting, you better have been the type of kid who could handle writing a 10 page essay at midnight the night before it was due.

[Nick Chertock @golfprogress]

@djanjali @ebloch Clients rarely look at the California return past page 2. Even staff accountants have this habit. I learned to embrace looking at Sched CA on a 540 bc I persuaded myself it was important, but my clients won’t look at it even if I force their eyes open

[Nick Chertock @golfprogress]

Everyone teaching creators about taxes promoting deducting all the clothing they wear, and telling trainers to deduct all of their gym clothes and supplements and gym memberships….. seems like all the relevant court cases pre-date the era of the IG influencer, so these Tax “coaches” claim those cases to be irrelevant in 2026.

[Nick Chertock @golfprogress]

@stevenchung So if I’m a model and I sell videos of myself wearing 100 different types of underwear, would you agree that the clothing would be deductible, or would you say I could wear the underwear in my personal life so it’s not deductible? @TaxLeverage @KarltonDennis

[Nick Chertock @golfprogress]

@bsuecannon This last 10/15 was definitely my worst…. I did schedule Tax prep, but the offshore team I was relying on overpromised what they could do and I had to end up taking on a ton of it myself in the last two weeks.

[Mark Edler, CPA @markedlercpa]

15 subs we are COOKING

[Nick Chertock @golfprogress]

@mhutchlv @mkoontz328 @wanderlustworkr My clients can have AI review their return… I’m not allowed to do the same. There are no clear rules in place…right now most Tax firms are way too scared to be dropping a client’s return into an LLM. And we’re not going to be telling clients that they should do it.

[Nick Chertock @golfprogress]

@CPAJeff @mkoontz328 @seanfgates It’s kind of hidden actually…. I believe it’s on page 4 of the California return and a lot of tax preparers don’t look beyond the first two pages when they review State returns. If they even look at the State.

[Nick Chertock @golfprogress]

@0xcryptotax The tax people who gave you this return clearly did not actually look at the California return before they signed off. It’s unlikely that they actually thought you should pay this penalty. Not that this helps. I’m sure it’s embarrassing for them.

[Nick Chertock @golfprogress]

@ebloch This is a prime example of a basic mistake not requiring AI. Good for you that OpenAI found it, but half of the responses are going to be questioning why you as the client didn’t notice it. It’s a bonehead error. And a sign that the finished product is not being looked at.

[Nick Chertock @golfprogress]

He didn’t say he had a balance…. Maybe this penalty just reduced his overpayment? I see the California healthcare penalty get computed by mistake all the time. Most likely due to software defaults. It’s definitely a sign that the Tax preparer didn’t properly review the return.

[Nick Chertock @golfprogress]

@KKelley_golf @freddydoubles Both of those companies are out of business

[Nick Chertock @golfprogress]

@RDriscollCPA @kevin_notoleary In this case, it was not anything to do with the client. It was the AI Tax prep software I was using.

[Nick Chertock @golfprogress]

@RDriscollCPA @boboknight They get K-1s in August or September. A lot of my clients are in the venture-capital world. Some are getting hedge fund K-1s a bit earlier, like July. Some are law firm partners so July/August. A handful I could have done in April. Most have to be on extension.

[Nick Chertock @golfprogress]

I spent four hours on the 15th cleaning up bad AI data entry. It saves time on some aspects but not flexible enough right now. It created 200 8621s for a client where I would not have bothered with any of them. And each of them needed me to manually input more information to clear e-file diagnostics. AI can poison a return with its inputs without giving you a chance to ask why it did that or ask it to partially undo what it did.

[Nick Chertock @golfprogress]

They’re both incredibly stressful…. About 2/3rds of my clients go on extension. I still have to ascertain how much they might owe in April, which involves quite a bit of work. October deadline is a bit worse, because you know there is no more time. But April does involve all the clients who want to actually file on time plus extensions plus Q1 estimates.