Advisors for entrepreneur / founder clients

Founders have two balance sheets

Company ownership may be valuable but illiquid, and a funding round's price is not the cash you can use to pay a mortgage. Start with two views: household runway and company exposure. List accessible savings, base pay, debt, insurance, dependents and tax liabilities. Separately list shares, vesting, exercise costs, dilution, investor preferences and any guarantees. Then ask what the household can withstand if the company takes longer to exit or never reaches its last valuation. An advisor can help build a plan that lets you make company decisions without every month becoming a personal liquidity emergency.

Bring your cap table summary, grant and shareholder documents, recent tax returns and a simple spending estimate to a professional you choose. Do not disclose confidential company records to a directory or an unvetted stranger. A founder's counsel, company finance lead and personal tax adviser should agree on what information can be shared and who makes which decisions.

Choose help for the company's stage

• At formation: ask counsel and a tax specialist to review entity structure, share issuance and any time-sensitive elections. The financial advisor can model household cash and risk, but cannot replace them.
• At fundraising: distinguish headline valuation from your economic ownership after dilution, vesting and liquidation preferences. Decide whether salary and cash reserves are adequate.
• At secondary liquidity: model proceeds after taxes, remaining exposure and any restrictions before deciding whether a partial sale improves resilience.
• At exit: plan tax reserves, concentrated proceeds, income replacement and an investment policy before the wire arrives.

Ask candidates to walk through how their advice changes across stages. Someone who has only managed liquid portfolios may be useful later but not qualified to lead a complex pre-exit decision.

Founder equity has deadlines and uncertainty

Share classes, options and restricted stock have different legal and tax mechanics. An 83(b) election may be relevant to certain restricted property and has a strict filing window; it can also create tax cost even if the shares later lose value. The IRS Section 83(b) election form helps frame the question, but filing is a specialist decision. Potential stock-sale tax treatment depends on company and shareholder facts, issuance and holding requirements, and current law. Do not plan an exit around a presumed exclusion without a written tax review of your own shares.

Options can also require cash to exercise and create tax obligations before liquidity. Add each vest, expiration and decision date to a shared timeline with your CPA and counsel. A reliable advisor should show an adverse scenario, not only a best-case IPO slide.

Make diversification an explicit tradeoff

Founders often hear that selling any shares shows weak conviction. But household security and company commitment are separate choices. If a permitted secondary sale is available, model the after-tax money that would cover years of personal needs and the upside you retain. Compare that with the risk of holding everything. If no sale is possible, build liquid investments from salary when feasible and keep essential insurance and reserves current. Investor.gov's diversification guide explains why owning one company, even a company you know intimately, does not spread portfolio risk.

Screen the advisor and the fee

Ask whether the advisor has worked with founders whose wealth was mostly private, whether they will coordinate with company counsel and your personal tax professional, and whether their fee structure works before there are assets to manage. A percentage-of-assets fee may be a poor fit for a pre-liquidity founder; a scoped planning fee may be easier to assess. Get scope and costs in writing. Verify registration, services, conflicts and disclosures through IAPD.

Five useful interview questions

1. How do you plan for a founder with high paper wealth and low liquid savings?
2. Which equity decisions do you handle, and when do CPA and counsel take the lead?
3. How would you model dilution, preferences, tax and delayed liquidity?
4. What would you recommend checking before a secondary sale, without assuming the sale is allowed?
5. What do I pay now, before a liquid exit, and what changes after one?

No advisor here is currently tagged as a founder specialist. The profiles below are a general roster, not proof of founder-specific experience. Ask them directly about the decisions you face. The business-owner guide covers related planning for privately owned firms.