Your company has at least 3 share prices you might hear/see: > 409A value: an independent appraisal that sets the strike price for new option grants and your FMV for tax purposes > Tender price: the price investors (or your company) are offering for shares in a specific tender transaction > Preferred price: what investors paid for preferred shares in the latest financing round (typically the high-water mark) mixing these numbers up is how people dramatically misjudge what their private-company equity is actually worth

> RSU tax shortfall > tender offers > secondary markets > 83(b) elections > tax withholding > ESPP participation > benefits enrollment > secondary sales > qualified small business stock > 280G parachute payments > offer letters > vesting schedule > 409a valuation > grant documents > right of first refusal > liquidation preference > simple agreement for future equity > convertible note > non-recourse loan > exercise costs > alternative minimum tax > cashless exercise > incentive stock option > section 1244 worthless stock > 10b5-1 insider trading plan > qualifying disposition > contribution of private stock to DAF where do you even start?

umbrella liability insurance is pound-for-pound some of the best, most cost effective insurance you can buy I routinely see people with $5M - 10M+ net worth carrying very basic liability coverage within their home & auto and no umbrella policy to sit on top >car accident with a serious injury >someone gets hurt on your property >your teenager causes an accident >lawsuit exceeds your underlying policy limits you can get millions of dollars of coverage for a few hundred or a few thousand dollars per year

at 22 years old, the last living grandparent I had at the time passed away. if any of them were still with us today, they would legitimately be floored pulling up to our house. my parents didn’t receive $1 of inheritance from them. I operate every single day as if I’m not going to see $1 from them either. I received a generational work ethic from them that kicked in at about 15 years old. before that? a values-based upbringing, people skills, and a relentless sense of optimism. that’s literally all I needed.

I don't mind paying taxes. but I can't stand tax *surprises*. It's why I have a running tax projection going throughout the year. -YTD paystub -YTD investment income -YTD realized capital gain/loss -Expected income / deductions before year-end -Equity comp vesting/exercises -Business income -Estimated tax payments -Charitable giving -Any major one-time income events It's not about perfectly predicting the final tax bill (although it is sweet when it comes within <$50). It's about knowing in September/October that you're likely $50K short instead of finding out in April.

the "millionaire next door" is a very real concept. they are typically unassuming & default kind. you would NEVER guess how much money they have. (they prefer it that way) they grind away and quietly stack capital. they give to charity & support their kids without fostering entitlement. they also happen to be worth $5-$15 million. I've learned that there are kind, hard-working, values-based people everywhere. I've personally lived in 7 different states and serve clients in 16 states from coast to coast. stereotyping based on any measurable demographic is a mostly useless exercise. there are also assholes everywhere. many of them treat wealth accumulation as a you-know-what measuring contest. the net worth number will never be enough, because it was never about the money in the first place. my clients with the highest net worth figures earned their wealth via 1 of the following: >> joined the right company at the right time (equity comp) >> built something extremely valuable (business, product) >> grinded to be in the top 1% of what they do & have a massive W-2 every year to show for it stress and money are always going to go hand-in-hand. but you can legitimately watch it melt away on people if: >> they know exactly what they HAVE and track things regularly >> they know exactly what they NEED to achieve their values-based goals >>they know exactly how to GET THERE with an intentional plan >> they have a team of talented, objective professionals helping them steward their wealth

when your wife’s visions turn into your projects

There's a reason the wealthiest families in America have CPAs, CFPs, and estate attorneys who all talk to each other. It's not status. It's math. An integrated team catches what a single advisor misses every time.

many of my clients now have the challenge of answering the following age-old question at the ripe age of 30-40 years old: "What would I want my life to look like if money were no longer an issue?" I'm not a therapist by any definition, but I've helped dozens of people think through this exact problem set while assigning numbers to values. In reality, very few of my clients "need" me. I serve mostly brilliant people who are already independently wealthy by the time they get to me. The families I work with view this as an ongoing partnership, not a fleeting transactional engagement or a portfolio-management subscription. My responsibility is to bring good judgment, proactive planning, institutional resources, responsiveness, and an organized process around the financial decisions that matter most.

3 years ago today my wife and I hosted our entire wedding for < $30,000 *all in* at Emmy Squared in Philly that covered 100 guests, entire venue for the night, all you can eat and drink for 4-5 hours (no lines, no wait for anything), decorations, flowers, DJ, her dress, my tux, event planner, ice cream bar, after party down the street open bar at our favorite local dive, etc people still tell us it was one of the best weddings they’ve ever been to because it was different and primarily focused on the guest experience (food, drink, music, fun) happy anniversary, J ❤️

"Carta came in and gave us a presentation before the last big tender offer, but we all left more confused than we were before." not surprising. learning about RSU / ISO / NSO / ESPP / QSBS / AMT / 83(b) through traditional methods can be like taking the bar exam in a foreign language. it's part of the reason I started creating.

1. build your dream financial plan: >optimized cash flow >streamlined investment portfolio >values-based goal setting >dialed in savings rate 2. protect the hell out of it: >life & disability insurance >home & auto insurance >rock solid estate plan >"if I'm not here" document >umbrella liability coverage way too many people ignore #2.

1 day you are Head of Financial Planning for a Series A startup. the next day you get invited to a Zoom meeting where they ask you to turn in your laptop. life comes at you pretty fast. how do you respond?

putting my toddler to bed every night 7:59pm {still in their dark room} a state of blissful exhaustion not felt since I was 9 years old. I could (and might) fall asleep right here in full clothes and not wake up for 48 hours. better get up. 8:01pm {after leaving their room} wide awake. 37 things to do before laying back down again. I may not go to sleep ever again. I should stare at screens until 1am.