Succession is rarely just one handoff. The engagements that work cover three transitions in parallel.
Multi-state work across all 50 states.
Price scoped upfront. No hourly meter.
Answers within one business day.
Available beyond tax season. Quarterly check-ins.
Every engagement follows the same disciplined path. You always know what is next, and you always know who is doing it.
A complimentary 30 minutes. We scope what you actually need — and tell you straight if we are not the right fit.
Clear scope, deliverables, and a flat fee quoted upfront. No surprises. No hourly meter spinning in the background.
Family conversation facilitated together with all key stakeholders. Valuation baseline established. Multi-year succession memo within 60 days.
Quarterly family + leadership check-ins. Ownership transfer milestones tracked. Tax-position changes (gift-tax exclusion shifts, exemption changes) flagged immediately.
Three siblings, no one wanted the same outcome. Milestone facilitated 18 months of family work — alongside our family attorney — that ended with two of us in operating roles, one fully bought out, and a trust structure that protected the company from any future family drift. The business is still in family hands. The tax bill came in 40% under what our first model predicted.
— Second-Gen Owner, Bay Area Family Business
Multi-generational transition · Milestone client 2022-2024
Realistically 5–10 years before the actual transition. Tax-efficient ownership transfers using gifting and trusts take years to fully fund. Operational succession (training successors, building independence from the founder) also takes years. Less than 5 years out and you are doing damage control, not planning.
No — we work alongside. Estate attorneys draft the trusts; we model the tax outcome and coordinate funding. Family attorneys handle governance documents; we structure the operating economics. Best results come from coordinated teams.
Common, and worth addressing directly. Often the right answer is a longer transition with interim leadership (key employee, board chair, fractional CEO) bridging the gap. We have helped families design 7–10 year transitions where the family eventually steps fully into ownership but not necessarily operations.
Also common. Then succession becomes an exit — sale to outside buyers, key employees, or private equity. Same financial work, different destination. We pivot the engagement accordingly.
The current $13.6M per person federal exemption is scheduled to drop in 2026. Families with $10M+ in business equity should be modeling the change now and considering accelerated gifting before the cliff. Always scoped to specific situations.
Yes — gift tax returns (Form 709), grantor trust returns, family limited partnership filings, and the annual maintenance work to keep the structure compliant. Coordinated with annual income tax returns.
A complimentary 30-minute call. Walk us through who is involved and what timeline feels right — we will tell you straight what succession planning would look like and where the wins are.
