Journal
Longer posts about RSUs, options, founder stock, and what happens when your company goes public or gets bought. General education, not personal advice.
Recent
Stock pay at tech companies
- Tech Executives
Insider stock: trading windows, 10b5-1 plans, and Form 4s
If you're on your company's insider list, the stock price isn't the only thing that matters. Your trading policy decides when you can sell, and your company's lawyers are part of the process.
- Tech Employees
RSUs vs. stock options: what's the difference?
People talk about "my equity" like it's one thing. It's usually a few different things with different rules. Here's how RSUs and options differ.
- Tech Founders
Thinking about a charitable remainder trust after an IPO or acquisition?
CRTs come up a lot after a big vest, an IPO, or a sale, and they often get mixed up with donor-advised funds. The first thing to know is that you can't undo one.
Archive
Older posts
Older posts on general money topics. They're still here for reference, but they're not what I focus on now.
- General
Why Physicians Struggle to Enjoy Their Wealth
Most physicians I work with have a problem you don't hear about enough. They save aggressively. They max out every account. They track every dollar. But they don't actually enjoy w…
- General
What Is a 457(b) Plan and Should Physicians Use It?
Most physicians I talk to have no idea this exists. They max out their 401(k) or 403(b), maybe hit the backdoor Roth, and think they're done. But if you work for a hospital or acad…
- General
Why Physicians Skip Disability Insurance (And Why That's a Mistake)
You spent four years in undergrad. Four years in med school. Three to seven years in residency. You're finally earning real money as an attending.…
- General
Why Do Smart Physicians Feel Lost With Money?
You spent over a decade in training. You mastered anatomy, pharmacology, pathophysiology. You can diagnose rare conditions and make life-or-death decisions. But when it comes to yo…
- General
How Should Physicians Handle Moonlighting Income for Taxes?
Most physicians take moonlighting gigs without thinking about the tax hit coming. You pick up extra shifts, do locum tenens work, or consult on the side. The money looks good until…
- Tech Executives
Direct indexing when most of your net worth is the company
Direct indexing gets sold as tax magic. For tech executives it is usually a conversation about not buying more of the ticker you already cannot escape.
- Tech Executives
Executive stock options and ESOPs, without the brochure language
An executive option grant and an ESOP account can both say stock. They are different machines. Read the plan before anyone sells you a strategy.
- Physicians
How Physicians Building Health Tech Startups Can Save $500K+ on Taxes with QSBS
Physician health tech founders pay $500K+ in taxes on exits. QSBS tax exclusion could change that. Learn if your startup qualifies and the 83(b) election timing that matters.
- Physicians
Should Physicians Invest in Crypto?
Physician financial planning often ignores crypto. Learn if Bitcoin and digital assets belong in a doctor's portfolio and how much allocation makes sense.
- General
When Should Physicians Invest in Real Estate?
Physician financial planning gets complicated when real estate enters the picture. You've saved during residency, you're finally attending, and everyone's telling you to buy rental…
- General
Why Should Physicians Get Disability Insurance Before Residency Ends?
Most residents I work with think disability insurance can wait until they're attending. They're focused on surviving 80-hour weeks, passing boards, and keeping their heads above wa…
- General
How Early Should Physicians Start Investing? The Number That Will Surprise You
But you're also looking at six figures of student loans, maybe a car payment, maybe you want to buy a house eventually. So you tell yourself: I'll start investing next year. When I…
- General
The Lost Decade: Why Physicians Start Building Wealth 10 Years Behind Everyone Else
Most people start earning a real salary at 22 or 23. If they're halfway smart about it, they start putting money away pretty early. By the time they're 30, they've had seven or eig…
- General
Why Your Physician Contract Matters More Than Your Salary
You're negotiating your first attending job. The recruiter throws out a number. $350,000.…
- General
Why Do Physicians Feel Broke Even Making $300K+?
A physician client told me something last month that stuck with me. She said, "Malik, I was happier with less money."…
- General
What Do Physicians Miss When Negotiating Contracts?
You spent four years in medical school. Three to seven years in residency. Maybe more in fellowship. You're finally ready to sign your first attending contract.…
- Tech Entrepreneurs
The Money Mistakes Dual-Income Tech Couples Make (And How to Stop Making Them)
Two incomes, two companies, two equity packages, and two sets of tax situations. Most dual-income tech couples are leaving money on the table without realizing it.
- Universal
Emergency Fund: How Much Do You Actually Need? (The Real Math)
Everyone says 3 to 6 months of expenses. But that advice was written for someone with a completely different financial situation than yours. Here's how to figure out the right number for high earners, founders, and anyone with irregular income.
- Tech Entrepreneurs
The Health Insurance Gap Nobody Warns Founders About
Leaving a salaried job to start a company comes with a health insurance problem most founders don't see until it's too late. Here's what to do before you make the leap.
- Physicians
Physician Mortgage Loans: What Doctor Loan Programs Actually Offer (and Where They Fall Short)
Physician mortgage programs are marketed heavily to residents and new attendings. They can be a smart tool in the right situation. But they're not always the best option, and the terms vary more than most people realize.
- Physicians
What Physicians Need to Know About the Financial Side of Partnership Track
Making partner at a private practice or becoming a shareholder in a physician-owned group is a big financial decision. Most doctors focus on the clinical opportunity and miss the financial structure entirely.
- Tech Entrepreneurs
Your Financial Checklist 12 Months Before an IPO or Acquisition
If your company is 12 months out from going public or being acquired, your financial decisions right now will determine how much of that liquidity event you actually keep. Most founders wait too long.
- Tech Entrepreneurs
Solo 401k vs SEP IRA vs SIMPLE IRA: Which One Actually Makes Sense for Founders?
If you're a self-employed founder or running a small startup, you have three main retirement account options. Here's how to actually choose the right one without getting lost in the details.
- Personal Finance
How Do You Know When It's Time to Change Financial Advisors?
Most people stay with a financial advisor way longer than they should. Not because the relationship is great, but because switching feels complicated. Here's how to actually evaluate whether your current advisor is serving you well.
- Physicians
The Spousal IRA: A Retirement Account Most Physician Households Aren't Using
If your spouse isn't working or earns less than you, there's a way to fund a retirement account in their name using your income. Most physician households skip this. Here's why that's a mistake.
- General
Is Your Financial Identity Outdated?
Here's something I see constantly. A resident finally matches. Now they're making $65,000 a year. For the first time, they have actual income. But they're still making financial de…
- Physicians
Locum Tenens Tax Strategy: How Physicians Can Keep More of That Extra Income
Locum tenens income hits differently on your taxes than your W-2 salary. Most physicians don't know the rules until they owe a surprise tax bill. Here's how to handle it correctly from the start.
- Tech Founders
Donor Advised Funds After a Startup Exit: The Tax Strategy Most Founders Miss
If you're charitably inclined and you're approaching a liquidity event, a donor advised fund might be one of the most powerful tax tools available to you. Most founders hear about it after the fact. Here's the full picture.
- General
Why Are Physicians Leaving HSA Money on the Table?
A resident asked me last week if they should max out their HSA. They were making $65,000, stressed about loans, and treating it like an afterthought.…
- Tech Founders
Key Person Insurance for Founders: What It Is and When You Actually Need It
Investors sometimes require it. Partners sometimes want it. And most founders have never thought about it. Here's what key person insurance actually does and how to decide if it belongs in your startup's financial plan.
- Tech Founders
Secondary Sales and Tender Offers: How Founders Can Get Liquidity Before an Exit
Most founders don't know they can sell shares before the company goes public or gets acquired. Secondary sales and tender offers let you take some chips off the table while the company is still growing. Here's what you need to know.
- Tech Founders
How Much Should a Founder Pay Themselves? The Honest Answer
Most founders underpay themselves out of guilt or optics. That can actually cost you more in taxes and create serious problems down the road. Here's how to think about founder salary at every stage.
- General
QSBS Rules Changed in 2026: What Founders and Physicians Need to Know
If you own a startup or a medical practice organized as a C corporation, the Qualified Small Business Stock exclusion just got better. The cap jumped from $10 million to $15 millio…
- General
Why Should Physicians Save 20 Percent of Their Income
Most financial advisors tell you to save 15 percent of your income. That's the standard advice you'll hear everywhere. But physicians aren't most people, and 15 percent won't cut i…
- General
What Type of Disability Insurance Do Physicians Need?
If you're a physician reading this, you've probably heard you need disability insurance. Maybe someone told you it's important. Maybe you nodded and meant to call an agent. Maybe y…
- Universal
The Backdoor Roth IRA: A Step-by-Step Guide for High Earners in 2026
If you make too much to contribute to a Roth IRA directly, there's a legal workaround that takes about 20 minutes. Here's exactly how to do it, and why you should.
- General
Should Medical Residents Buy a House?
If you're a resident doctor making $65,000 a year while sitting on $250,000 in student loans, buying a house probably feels like the next logical step. You're building your career,…
- Tech Founders
When Your Entire Net Worth Is Trapped in One Company
Most founders have 80% or more of their net worth in a single company they can't sell. That's not wealth. That's a bet. Here's how to think about concentrated stock risk.
- Tech Founders
How to Split Equity Between 4 Co-Founders Without Destroying Your Startup
Four co-founders means four opinions on who deserves what. Here's how to split equity fairly without creating resentment that kills the company before it even launches.
- Financial Planning
How to Evaluate a Financial Advisor: Red Flags and Questions That Separate Good Advisors from Sales Reps
Most people hire a financial advisor based on a recommendation or a sales pitch. Here's how to actually evaluate whether an advisor is worth working with, or if they're just trying to sell you products.
- Tech Founders
International Founders on F-1 and H-1B Visas: How to Handle Equity and Taxes Without Getting Deported
If you're on an F-1 or H-1B visa and starting a company in the US, the rules around equity compensation and tax compliance are more complex than for citizens. Here's what you need to know to avoid visa violations and tax disasters.
- Tech Founders
ISO vs NSO: Which Stock Options Work Better for AI Startup Employees
If you're joining an AI startup, the type of stock options you get matters more than you think. Here's how ISOs and NSOs actually work, and which one makes sense for your situation.
- Physicians
Physician Contract Negotiation: Signing Bonus, Relocation, and Tail Coverage Actually Matter More Than Salary
Most physicians focus on base salary when negotiating their first attending contract. But signing bonuses, relocation packages, and tail coverage can be worth $50,000 to $150,000. Here's what to actually negotiate for.
- Tech Founders
Revenue-Based Financing vs Equity Dilution: Which One Makes Sense for Your Startup
Raising a Series A means giving up 20-25% of your company. Revenue-based financing lets you keep equity but comes with monthly payments. Here's how to decide which makes sense for your situation.
- General
How Do Physicians Build Wealth Differently Than Everyone Else?
Most physicians I work with are smart, driven people who spent over a decade learning how to save lives. But nobody taught them how to build wealth. And the standard financial advi…
- Tech Founders
What Actually Happens to Your Money After a Startup Acquisition
Your company just got acquired. The press release is out. Everyone is congratulating you. But the financial reality of an acquisition is way more complicated than most founders expect.
- Tech Founders
The 83(b) election: the 30-day window founders miss
If you got restricted stock in your startup, you have 30 days to file an 83(b) election. Most founders don't know it exists.
- General
What's the Best Retirement Plan for Physicians?
I get this question at least once a week from physicians at every stage. "What retirement account should I be using?" "Is a 401k better than a 403b?" "Should I do a defined benefit…
- General
When Should Physicians Invest in Real Estate?
I get asked this question at least once a week. A resident will text me, or an attending will bring it up after a meeting. Everyone seems to think real estate is the golden ticket.…
- Tech Founders
You Just Got Funded. Now What? 5 Financial Moves Most Founders Skip
Raising a round is exciting. But most founders immediately pour everything back into the company and forget about their own financial health. Here are 5 things you should do the week the wire hits.
- Physicians
RAP vs IBR: Which Repayment Plan Should Physicians Choose in 2026?
The SAVE plan is gone. IBR is being phased out. The new RAP plan charges more. Here's how to figure out which repayment path actually makes sense for your situation.
- Physicians
The Student Loan Consolidation Deadline Every Physician Needs to Know (July 1, 2026)
There's a hard deadline coming that will change how physicians repay their student loans. If you don't act before July 1, 2026, you could lose access to IBR and pay thousands more per year.
- General
Can Physicians Really Zero Out Their Tax Bill with Real Estate?
You've probably seen the headlines. A physician couple eliminated their federal tax bill for seven straight years using real estate. Business Insider ran a piece on it. People shar…
- Financial Planning
You Don't Need a Perfect Plan. You Need Any Plan.
The biggest financial mistake isn't picking the wrong investment. It's waiting until you have it all figured out before you do anything.
- Physicians
Why Every Resident Should Lock in Insurance Before Finishing Training
Disability and life insurance get more expensive and harder to qualify for every year. Residency is the best time to lock them in, and almost nobody does.
- Physicians
Why Do So Many Doctors Go Broke Despite High Incomes?
Physicians earn some of the highest incomes in the country, yet many retire with less than expected. Here's why physician financial planning fails — and how to fix it.
- Physicians
Refinance or Wait for Forgiveness? The Math for Physicians in 2026
With PSLF rules changing and rates around 4.5%, the refinance vs. forgiveness decision just got a lot more complicated. Let's break down the actual numbers.
- Physician Finance
Can Resident Doctors Get 401(k) Matching While Paying Student Loans?
Most residents I talk to are making a decision that feels obvious: pay down student loans first, invest later.…
- General
What Taxes Affect Doctors Most? A Simple Guide
I work with a lot of physicians. And the one thing I see over and over is this: doctors are great at making money, but they're not great at keeping it. It's not their fault. Nobody…
- Tech Founders
Your Startup Failed. Here's How to Financially Reset.
Nobody talks about the financial aftermath of a failed startup. No exit, no payout, just a pile of decisions to make. Here's where to start.
- Tech Founders
Cash Is Not a Strategy: Why Sitting on Money Is Costing You
You worked hard for that money. Now it's sitting in a savings account losing value every single day. Here's why that's a bigger problem than you think.
- Physicians
What Should a New Attending Physician Do With Their First Real Paycheck?
You just finished residency. The paycheck finally looks right. Here's what actually matters in the first year as an attending — and what can set you back a decade if you get it wrong.
- Physicians
What Is a Defined Benefit Plan for Physicians (And Should You Have One)?
Most physicians max out their 401(k) and call it a day. But there's a retirement account that lets you shelter up to $290,000 per year. Most doctors have never heard of it.
- Tech Founders
The RSU Tax Trap: What Tech Employees Get Wrong Every Year
RSUs feel like free money until tax season hits. Here's why so many tech workers get blindsided and what you can actually do about it.
- Investing
Why I Don't Try to Time the Market (And You Shouldn't Either)
Everyone thinks they can predict market tops and bottoms. The data says otherwise. Here's why staying invested beats timing every time.
- Physicians
How Much Should Resident Doctors Save? A Realistic Guide
Residents making $60K with $250K in loans ask me this all the time. The honest answer: more than you think, with less complexity than you fear.
- Tech Founders
Why Tech Founders Need a Financial Plan Before the Exit
Most founders spend years building their company and zero time planning for what happens when the money actually hits. That's a problem.
- Physicians
5 Money Mistakes Early-Career Attending Physicians Make
Your attending salary just hit. $250K feels like a fortune after residency. But these five mistakes can cost you millions over your career.
- Physicians
PSLF Changed in 2026: What Medical Residents Need to Know Now
Starting July 1, 2026, residency years won't count toward Public Service Loan Forgiveness. If you're a medical student or resident, this changes everything.
- Physician Finance
What Is the RAP Plan Replacing SAVE, PAYE, and IBR?
If you're a physician with student loans, you need to pay attention to this.…
- Physicians
Should Doctors Pay Off Student Loans or Invest? A Framework That Actually Works
Most physicians face $200K+ in student debt and wonder: pay it off fast or start investing? Here's how to think through it without losing years of compound growth.
- Tech Entrepreneurs
How VCs Should Think About Carried Interest Tax Planning
Carried interest gets favorable long-term capital gains treatment, but the rules changed in 2018. Here's what VCs need to know to avoid surprises.
- Tech Entrepreneurs
QSBS: The $10M Tax Break Serial Founders Keep Missing
Section 1202 lets you exclude up to $10 million in capital gains when you sell startup stock. But most founders don't know the rules and leave millions on the table.
- Tech Entrepreneurs
83(b) Elections Explained: Examples from AI Startups
AI startups are seeing massive valuation swings. The 83(b) election can mean a much smaller tax bill, but you only have 30 days to file it.
- Tech Entrepreneurs
5 Tax Mistakes Fintech Founders Make After a Series A
Fintech founders raised $42.8 billion in 2025, but most miss critical tax strategies post-funding. Here are the five mistakes I see most often.
- Investing
The Only 5 Investing Principles You Actually Need
Forget the noise. Here are the five principles that actually matter for building wealth over the long term.
- Physicians
Why Your Employer's Disability Insurance Isn't Enough
As a physician, your ability to earn is your most valuable asset. Here's why group disability coverage falls short and what to do about it.
- Tech Entrepreneurs
QSBS: The Tax Break Every Tech Founder Should Know
Qualified Small Business Stock (QSBS) can save you millions in taxes when you exit your startup. Here's what you need to know before your next funding round.