Taxes don't sleep just because you start a new job and your weekly live class gets canceled

We power through!

We're on Week 5 of 11 of running through my entire course on tax planning in personal financial planning

Week 5: Other Deductions, Penalties, & Loss Disallowance🧵 First, not all expenses are deductible

Seems obvious (you would think)

For instance, payments violating public policy, like bribes or fines, cannot be deducted

Neither can the majority of political contributions

12 years ago, the 30 for 30 documentary "Broke" first aired on ESPN

I was in college at the time and it was all my friends and I could talk about (we were financial planning majors and huge sports fans)

Here are 7 athletes that managed to turn millions into dust 🧵 "Broke" explored how many pro athletes end up in financial distress despite earning millions during their career

Sadly it's not a unique story

Poor money management, lavish lifestyles, bad investments, and exploitation by bad actors, family, friends, and shady advisors

We're on Week 4 of 11 of running through my entire UCLA course on tax planning

It's kept me accountable to pushing out a longer thread on a weekly basis

Want to pay less tax? You need to understand deductions

Week 4: Intro to Deductions and Itemized Deductions Deep Dive 🧵 Deductions are not guaranteed and can be subject to scrutiny

→ Taxpayer has burden of proof
→ Adequate records of expenses must be maintained

They never taught you anything about taxes

Honestly, that's a massive problem we should fix

I voluntarily took on 1 of the least desirable courses in our CFP program & turned it into the best reviewed course we offer

Week 3: Income from Employment & Investment Activities 🧵 If you missed my posts from the last 2 weeks, I'm going to be posting a thread for all 11 weeks of the CFP income tax planning class I teach for UCLA Extension

It's my 9th time teaching the course

2 hours every Wednesday night on Zoom with quizzes, cases, and exams in between

I have the honor of serving some of the smartest & most successful people in tech

top tier Developers, PMs, Founders, etc

by hiring me, most have chosen the "driver/passenger" approach to their finances

Here are 10 things I do for them up front that stand apart 🧵 First -- "driver/passenger" in this case means:

"I want to delegate most of this function, but I'd still like to be pretty heavily involved and informed as we go"

My practice is a premium, comprehensive service and it requires some work up front

2023 was an incredible year personally & professionally

Here on X, I went from 180 followers in June --> 3.3k

I've been contacted by dozens of industry colleagues and 15+ qualified clients in the pipeline from X

Here are some of the top Tweets & Threads that made it happen 🧵


Going super deep on company equity / ISO's, etc

https://x.com/markcecchini/status/1700882714230972553?s=20

It's estimated that there are approximately 29.2 Million "forgotten" 401(k) accounts holding as much as $16.5 Trillion...

I get it, leaving a job is stressful & we don't want to deal with the administrative side

So what CAN you do with your old 401(k) and how do you do it? 🧵 Let’s demystify 1 thing —

You should almost always roll your old 401(k) / 403(b) / 401(a) / 457(b) / TSP account into your new employer's retirement plan OR some type of IRA vehicle

There are a lot of factors at play

Here are the main options IMO:

You really have ~35 days to save yourself thousands of dollars this year...

Let's be honest, not much usually gets done after 12/23

Also custodians (Schwab, Fidelity, Vanguard) sometimes stop accepting requests

Here are 10 major things to consider before it's too late 🧵 There's a reason you've seen so many year end posts lately

It's the time of year when we can do a LOT of good planning and tax work

IMO it all starts with a thorough tax projection which can be used as a modeling zone:

https://twitter.com/881486490/status/1690029888374181888

Whether you work in tech or not; you should be aware of "the Manual"

Easily one of the best collections of personal finance articles and interviews I've seen

It's written in a concise and relatable style

Here are 13 articles to set your knowledge apart from your peers 🧵 1. Company Equity Deep Dive

manual.withcompound.com/equity-guide-f…

You're damn right college athletes should be able to get paid

Can you imagine bringing in millions of dollars for an organization and not pocketing any of the profits?

Here's the latest on the NIL (Name Image Likeness) madness and how athletes can plan around their wealth 🧵 It's no secret that college athletics can be revenue generating machines for universities

particularly major TV sports like football/basketball

(there are TEN football programs that generate in excess of $100,000,000 in revenue for their respective athletic programs per year)

I've input 100+ tax returns for high net worth clients as an associate

I've reviewed dozens more alongside talented CPA's

I get paid to teach tax planning to aspiring CFP's

Today seemed like a good day to expose bogus "tax strategies" and outline legitimate tax planning 🧵 It's hard not to see this stuff online all over the place, all the time

It's dangerous and can lead to very bad outcomes

My advice would be to be VERY careful about what you believe on TikTok, etc

"Emily" was an early employee at Blue Apron

She was granted Incentive Stock Options (ISOs) when it was just a small startup

Unfortunately, her equity compensation strategy did not go as planned

Here's another cautionary tale of how equity comp could blow up in your face 🧵 I've talked a lot on X about equity & the various challenges

1) Some people exercise their options and they go to $0 before any liquidity event (fairly common for startups)

2) Some people exercise their options when they are small $$, and then things go to the moon (big exit)

Meeting with a founder who is getting acquired

Straightforward case -> giant pile of cash and capital gains to contend with

I'm estimating her tax liability from the transaction at $900k (no QSBS, sadly)

This might be the clearest explanation of capital gains you've read 🧵 Capital gains are the profits you make when you sell an asset, such as a stock, bond, or piece of real estate, for more than you paid for it

Capital gains can be short-term or long-term

I worked with an active NFL player for 5 years

As someone who played football growing up (and a big fan of the game), it was fascinating

I got a 1st hand look at NFL contracts, payroll, 401(k), benefits, & taxes

🧵 What's it like to be an advisor to a starting NFL lineman? 🧵 It's no secret that pro athletes haven't been the best with $$

This player's Dad knew my boss, and there was a baseline level of trust

Many firms and agents court athletes (some are bad actors)

@thejacobturner is top notch advisor working with athletes (and a great X follow)

Working for a company that goes public can change your life

The founders ring the bell on Wall Street as the confetti falls...everyone's rich!

Not so fast.

There's a 6-mo. lock up period where employees and insiders can't sell.

Why is this a thing, and what can you do? 🧵 If you're curious how an IPO works, consider this thread I wrote about Instacart

https://twitter.com/881486490/status/1694015921801622006

Imagine making $20k in 1 month just for holding a stock

No, I'm not talking about dividends...

I'm talking about premium income from a covered call strategy with a concentrated position

This is a very simple example, but the concept is something that most people don't know 🧵 A covered call is when you SELL a call option for a stock that you already own

Because you own it, that makes it a "covered" call option

You receive a premium from the buyer of the call option, & you agree to sell the stock at the relevant strike price if that price is reached

stock options can make you RICH if you don't screw it up

working w/ PM client leaving pre-IPO company

ISO's will convert to NSO's 90 days post-termination

we're deciding:

1) how many options to exercise before the 90-day
2) where to source liquidity for exercise & AMT

🧵 they've already exercised ISO's and NSO's this year

the company has generously extended a 3-year window to exercise vested options post-termination

but the ISO's convert to NSO's after 90 days

ISO's are more advantageous because they can qualify for long-term capital gain

Tony Robbins has sold more than 15 million book copies and 50 million audio programs...

In 2014, he tackled the topic of personal finance with his book "Money: Master the Game"

Tony hosted 1:1's with 50 legendary financial experts

Here are 10 takeaways I found hard to deny 🧵 1. Understand your financial freedom number

Robbins suggests calculating your ‘financial freedom number’

Not necessarily the net worth you need to be financially free

But the amount of annual "income" you'll need to live without depending on wages

Angel investing has gained a lot of popularity over the last several years

People like @Jason, @tferriss, @naval, @sacca have made a fortune via writing angel checks

...but what exactly is angel investing?
...and should you be doing it?

Here's my take 🧵 Angel investors are usually HNW individuals who invest their own capital in startups

They provide smaller amounts of funding compared to institutional VC firms

Some of my clients are founders themselves and work in tech, so there are lots of opportunities to get involved here

This is the IPO thread.

Instacart's IPO chatter has been going for 3 yrs, but it appears they may finally be ready to go next month.

If you are an employee or investor, how should you think about this?

Let's hit the grocery store & get ready for the NYSE opening bell 🧵 First - let's talk about IPO (initial public offering)

It's when a privately owned company lists its shares on a stock exchange

This makes the stock available for purchase by the public

Many people think of IPOs as big money-making opportunities

as a startup founder, you have a LOT on your plate

-->Investor fundraising
-->Internal leadership
-->Hiring talent
-->Scaling with user growth

When it comes to managing your wealth, these are 6 things you have to stay on top of to be in the top 1% of wealth builders 🧵 First, who is this relevant for?

--Early stage founders, employees, busy VC's
--Anyone who wants to delegate this to a company that works exclusively with the technology ecosystem

https://twitter.com/markcecchini/status/1663568530124447745