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 Does this still work if I have an unusually long…thumb?

[Nick Chertock @golfprogress]

@garrytan I’ve always believed that the entire reason people seek to be famous is so they do not have to give strangers context…. We want people to already know about us. Why we are important. Why they should admire us. Why we are special.

[Daniel Grieve @dangrievegolf]

( TEMPO ) Gaining control 🎯

The soft-landing shot is one of the most important shots in the short game. It's a mid-flighted shot that lands softly onto the green with control, allowing you to access tighter pins and get it close on firmer greens. T...

[Nick Chertock @golfprogress]

@LoganGrafTax @taxretreat I travel a ton for volleyball tournaments and we try most of the time to get Airbnbs instead of $400 a night hotel rooms…. It’s usually cheaper and you get a full kitchen.

[Nick Chertock @golfprogress]

@LoZabransky Give us their initials

[Nick Chertock @golfprogress]

@CathyWilliamsCA @LoZabransky All of us, except for the people who actually went through this in real life…. Somehow they have a clear conscious.

[Shauheen Nakhjavani @shkeengolf]

This is the easiest way to show you the simplified MATCHUP between body rotation & shaft pitch.

The steeper you are, the more you have to tilt in order to get the club back in position. If you try rotating instead, you’ll get way too steep on it.

The shallower you are, the more you need to rotate in order to get the club back into position. If you try tilting, you’ll get stuck way underneath and will suffer from all sorts of low point and contact issues.

This is a big reason why being shallower is specifically better for golfers who want to rotate more through the shot. Enjoy! 🤙

[Nick Chertock @golfprogress]

@LoZabransky He acts like before TCJA you could just write off golf and going to ball games even if 162A didn’t cover you. He acknowledges there was a change to the law but doesn’t comprehend what that change was but he likes to say he doesn’t get caught up in these tax nerd details

[Nick Chertock @golfprogress]

@mfinneygolf I never understood the logic of the old school coaches saying “Hogan never needed a launch monitor to win tournaments.” like the fact that there were people winning tournaments 80 years ago supports any claim about modern gear

[Nick Chertock @golfprogress]

@ryanmouquegolf Do you guys message in Skillest about having a zoom call and then one of you just initiates the call at the chosen time? Wondering exactly how you run this.

[LKD @LukeKerrDineen]

Why are blade putters going extinct?

This concept was explained to me the other day, and I found it super interesting

Quick 🧵

[Nick Chertock @golfprogress]

@CPATaxTeam @jasononfirms Listen to the podcasts while you play golf

[GREG ISENBERG @gregisenberg]

I just got back from SF and I FEEL INSPIRED.

I spent 5 days with frontier AI model teams, AI startup founders, and 3 billionaires.

My takeaways:

1. I had lunch with 3 billionaires. All of them are buying SaaS companies and rebuilding them agent-first. They were deeply inspired by Bending Spoons and Ryan Cohen's eBay deal. Buy the company, cut the headcount, rebuild the tech, add agents, add features, make more valuable experience, raise prices.

2. The frontier model companies are hungry for usage data from the field. They can see API calls and token counts. They can't see the actual workflows. If you're deep in a niche using these models in ways the model companies haven't seen, that understanding is incredibly valuable. Usage intelligence is the new alpha.

3. Consumer AI is massively underbuilt. Every billboard in SF is either B2B inference infrastructure or vertical agent companies. The entire city is optimized for enterprise. Meanwhile you have companies like Cal AI doing $50M ARR in 18 months as a consumer app. I met with a cool few teams doing consumer AI (@paulscherer / @ekuyda)

4. MCP came up in literally every conversation. The companies exposing their product as MCP endpoints are getting pulled into deals they never pitched for. The ones that aren't are becoming invisible to agents. This is the new SEO. If agents can't find you, you don't exist. Building products for agents is the new zeitgeist in general.

5. Not uncommon for hot seed rounds to be $25-50 million valuations. I saw a Series A at $450 million

6. If I had a dollar every time someone mentioned "forward-deployed engineer" this trip I could have funded a seed round. It's the hottest role in SF right now. The person who sits between the agent and the customer, making sure everything actually works.

7. The mood around open source shifted. A year ago it felt like open source was chasing the frontier models. Now founders are telling me Gemma and DeepSeek are good enough for 80% of what they need at a fraction of the cost. The "which model do you use" conversation is being replaced by "which model for which task." Model loyalty kinda feels dead.

8. Voice agents came up more than I expected. Multiple founders told me voice is the interface for the next billion users. The billion people who will never type a prompt will absolutely talk to one.

9. The Obsidian community in SF is weirdly intense. Multiple founders showed me their vaults unprompted. Like showing someone your home gym. It's a flex now. The quality of your knowledge base (second brain?) is becoming a status symbol among builders.

10. Maybe it was just the people I met but the age of the founders is shifting. I met more founders over 40 this trip than any trip before and more founders under age 21 than ever before. Founders getting older and younger at the same time.

11. I spoke to a lot of fast-growing startups, VCs and frontier models who are hiring content creators right now.

12. The restaurant scene in SF is actually better than it's been in years. Founders are going out more. Alcohol is out, not surprisingly.

13. SF doesn't feel like the only place anymore. We all have access to the same frontier models. We all read the same X feed. A founder in NYC or Lagos is calling the same APIs as a founder in SoMa. So in the past it felt like SF was always lightyears ahead, doesn't feel that way anymore. It's okay not to live in SF and have BIG DREAMS.

14. The coworking spaces in SF are half empty but the coffee shops are packed. People want to be around people. I had a few startup ideas here....

15. Walking around the Mission I noticed something: the street-level businesses, the taquerias, the barbershops, the laundromats, none of them use any AI at all.

16. I heard the phrase "agent debt" for the first time. Like technical debt but for agents. When you hack together an agent workflow fast and never clean it up, the system prompts conflict, the memory gets polluted, the tools overlap. 6 months later the agent is doing weird things and nobody knows why lol.

17. Met a few people who carry two phones now. One for personal. One that's basically an agent terminal running Telegram or iMessage connections to their agent fleet.

It's always amazing to get that dose of inspiration in SF. I FEEL INSPIRED.

But I'm so happy to be back home, locked in and building.

We're 12-18 months into a shift that will take 15 years to play out. The urgency in every conversation was real.

What an incredible time to be building.

[Nick Chertock @golfprogress]

@LoganGrafTax I was a failed stock broker in 1997. My mother told me that her friend told her that if I became a CPA “I could write my own ticket”…. I immediately started studying for the exam.

[Nick Chertock @golfprogress]

@AAnonSalesRep @LoganGrafTax @Micha_Siegel Does a single B mean the entire path forward is cut off if you are a CS Major?

[Logan Graf @LoganGrafTax]

If you haven't tried a meeting AI assistant yet, here's your sign (and a free month).

Paid partnership with Ping Assistant.

I'm calling Ping a Productivity Advisory Assistant. Yes, a brand new term.

After testing it out in my own firm, the most interesting part of Ping wasn’t even the notetaking.

It was seeing how AI can help organize information, surface ideas, reduce admin friction, help firms operate more effectively, and make more money.

Here's my in depth video going over all the features in Ping!

Check out the link in the comments to get a FREE MONTH of Ping.

[Nick Chertock @golfprogress]

I saw someone say this recently and it’s true. When you post a video about Claude, the entire accounting world stops to watch it.

[Jason Staats⚡ @jasononfirms]

A guide to every Claude Cowork feature accounting firms ought to know about, ad free

0:00 Intro
1:08 What plan to use
1:56 The desktop app
2:40 When to use Cowork
3:14 Model selection
3:51 How to reduce hallucinations
5:33 How to point it to your files
6:43 How projects work
8:55 How connectors work
11:34 How memory works
11:50 How custom instructions work
12:23 How skills work
13:50 How plugins work
15:26 How scheduled tasks work
16:55 Understanding usage limits
18:31 How to connect Claude to Chrome
19:56 How to control Cowork with your phone
20:30 How to let Cowork control your computer
22:31 Locking down access to your Claude org
23:45 Should you disable Cowork altogether?
25:20 Should you disable web search?
25:54 How to give Cowork tool access
27:02 Should you disable skills?
27:59 Should you disable Claude in Chrome?
29:10 Should you disable Computer Use?

[Adam Young Golf @adamyounggolf]

Do you want to know how to increase COMPRESSION in your #golf shots.

This thread🧵 explains how 👇👇👇

Bookmark 📑 this, and follow me
@adamyounggolf

[Nick Chertock @golfprogress]

@frydwia @Accel @viktor__com $100 billion company