Salary or distributions: the founder pay decision that sets your tax bill
How you take money out of your own company depends on its tax classification, and getting the mechanics wrong costs more than the amount you pay yourself.
Taxes
Business and founder taxes: what applies, what it costs and what to file.
The real cost of incorporating your startup in the wrong place
Where and how you form your company decides who can invest, what you owe each year and what it costs to undo later.
Rich on paper, short on cash: the founder liquidity problem nobody plans for
A large equity stake in a private company can coexist with a thin bank balance. Here is why that gap exists and the realistic ways founders close it.
Founder vesting and the 83(b) election: the 30-day deadline explained
Why founders put vesting on their own shares, what the 83(b) election changes about the tax bill, and the filing window that cannot be fixed once it closes.
How QSBS works: the Section 1202 rules founders ask about too late
The qualified small business stock exclusion can remove federal tax on a large gain, but only if conditions set years before the sale were met.
The cash math every bootstrapped founder should run every month
Without investors, cash timing is the business. The numbers to track, the money that only looks like yours and the levers that buy months of runway.
How bootstrapped founders pay themselves without starving the company
Owner draws, payroll salaries and the S corporation reasonable-compensation rule work very differently. How each works and how to avoid a surprise tax bill.
How founder secondary sales work, and why the company gets a say
Selling some of your shares before an exit is possible, but transfer restrictions, approval rights, valuation knock-on effects and tax rules shape every deal.
Family business succession starts a decade before the handover
Ownership, leadership and family harmony are three separate problems. The families that hand over well plan each one deliberately and early.
The rules every family business needs before hiring a relative
Hiring family can build loyalty or quietly poison a workplace. Written rules on roles, pay, reporting and exits make the difference, along with the payroll tax details.
What angel investing really costs a founder writing small checks
Founders get offered deals constantly. Before writing checks, understand the illiquidity, the follow-on pressure, the tax mechanics and the time it takes.
Solo 401(k), SEP-IRA or company plan: retirement saving for founders
Founders often skip retirement saving because the company feels like the plan. Here is how the main account types work and what changes as you hire.
Accepting crypto as a business: the tax and accounting mechanics
Taking payment in digital assets creates income, basis and a second taxable event when you sell. What changes for your books, payroll and risk controls.
Estimated taxes for founders: how the quarterly payments actually work
No employer withholds for you once your income comes from distributions, draws or a sale. How quarterly estimates work and how to avoid the penalty.
C corp, S corp or LLC: how your entity shapes what you personally pay
Entity choice decides whether profit is taxed once or twice, whether you owe self-employment tax, and which investors and exits remain open to you.
How to negotiate a startup offer when equity is half the package
The terms that decide what startup equity is really worth to you, from exercise windows to acceleration, and the levers worth pushing on beyond the number of shares.
The hidden paperwork of hiring a remote employee in another state
Hiring someone who works from a different state brings new tax accounts, insurance and employment rules. What changes, what to check and how to stay on top of it.
What founders should know before writing a company travel policy
Your first travel policy sets how much admin, friction, and tax exposure every trip creates, so here are the parts that matter and what to ask your accountant.
Company car tax basics every founder should understand before buying
A car used for business brings real deductions and real record-keeping duties, so here is how the main rules work and what to ask your accountant.
Leasing vs. buying a business vehicle: how the math actually works
The cheaper monthly payment is rarely the whole story, because cash flow, ownership, mileage, and tax treatment all differ when a business leases or buys a car.