Everything you have is in one engine, and the engine is the thing you wake up worrying about. Your accountant has explained the tangle twice. Nobody has tied the taxes, the estate, and the exit together into one plan.
The fear is simple and it is not stupid: if the business stumbles, everything stumbles with it. The house, the kids’ plans, your retirement, your parents’ care. There is no second engine. And every advisor you have met wanted to talk about a 401(k) match you do not have.
There is a quieter fear too. You know the conversations you keep deferring: the buy-sell agreement, what happens if you are out for a year, whether the will even mentions the company. They stay deferred because having them means admitting the engine could stop, and you are the one everyone relies on to keep it running.
And a third, which is about you rather than the business. You start fast and go wide. The plan you meant to build is one of several things sitting at seventy percent. Your brain is not broken. It needs a cap, not a cure.
Free, no email gate, and built for the owner whose personal balance sheet is tangled up with the company’s.
Leave the business out for a minute and enter only what sits outside it; the Walk-Away number shows how far the rest of your life is from standing on its own if the engine stopped tomorrow.
Enter the estate including the business value, growth, spending, and time to transfer; compare doing nothing, annual gifting, and an irrevocable trust, and see the ‘Trust Advantage’ gap, which for estates well over the exemption is often eight figures.
If you or your key people hold ISOs, NSOs, or RSUs in the company, this runs the exercise cost, the AMT bill on the spread, and the total cash out, so nobody writes a six-figure check for stock they cannot sell.
Four Field Manual pages, picked for the founder who has to keep running the thing while planning around it.
The business is the engine; name what it is funding (the payload, the reason for the trip) and set a minimum commitment to each, so the engine stops being the only thing you are.
The crisis you can already see (a key person leaves, you are out for six months, the big client walks) gets a written response now, including who calls whom and what the business does in week one.
List every open project, business and personal, in three columns; if more than two are in Build, that is why the estate plan is still a draft, and the fix is a cap, not more discipline.
The buy-sell agreement or the will that is drafted and unsigned is a finished thing in a drawer; put a date inside seven days on signing it and tell one person the date.
Yours and the company’s, together: owner comp structure, distributions, quarterly tax, and the personal picture that depends on the business. Reviewed as your life and your company change, not against a 30-year template.
Solo 401(k), SEP, defined benefit, QSBS, Section 199A, coordinated with your CPA rather than stepping on them. Disability, key-person, buy-sell, will, trust, beneficiary alignment: the conversations founders defer until they are urgent.
Pre-sale tax positioning, post-sale portfolio strategy, and the ‘what do I do with the money’ question answered before a buyer forces it.
Comprehensive planning is a $1,000 to $3,000 one-time setup based on complexity plus a $150 to $500 monthly retainer with a 12-month minimum; combined with investment management the minimum is $500K, and modular single-topic sessions ($300 to $500 for 60 to 90 minutes) have no minimum.
If you want a plan that assumes a steady W-2 paycheck and a 401(k) match, almost any advisor can hand you that template, and it will not fit you. And if you are not willing to have the disability, buy-sell, and estate conversations, the plan has a hole in it that I cannot paper over.
Most plans are written for someone with a W-2, a 401(k) match, and a 30-year career arc. An owner has income that spikes and stalls, S-corp distributions and K-1s, a personal balance sheet tangled with the business one, and a largest asset that is also the job. The plan covers cash flow and owner comp, tax strategy across entities, risk and estate and succession, and exit and liquidity planning, and it gets reviewed as the company changes.
Plan setup is $1,000 to $3,000 one-time based on complexity, then an ongoing retainer of $150 to $500 a month with a 12-month minimum. Planning clients who add investment management pay a discounted 0.25% a year on managed assets, and the combined engagement generally starts at $500K. For one specific question, modular sessions run $300 to $500 for 60 to 90 minutes with no minimum. Fee-only, no commissions, every fee on one page.
Neither. Tax strategy is coordinated with your CPA, not done over them. When insurance is needed (disability, key-person, the funding behind a buy-sell), the requirement gets identified here and referred to a fee-disclosed broker; StandUP earns nothing from the transaction. The planning job is to tie the pieces together into one picture so that the parts your accountant, your attorney, and your insurance broker each own actually point in the same direction.
Run the calculators first; they are free and they do not ask for your email. If the numbers raise more questions than they answer, that is what the conversation is for.