Ken's Advisor Circus: A Teaser in the Mail and a Trust on the Cap Table

Diagnosis - four structural failures, not a communication problem.

1. No single leader and no written scope. Five advisors, five agendas, no defined decision rights, and Ken is acting as a router rather than an owner. "Keep everyone on the same page" is a request for a quarterback, not for a memo.
2. A process was launched before the company was ready. The broker has sent a teaser to 40 buyers with no quality-of-earnings work, no valuation reconciliation, and no confidentiality architecture you control. That is a one-way disclosure of the owner's intentions to the entire buyer universe, and it is now irreversible.
3. The cap table is complicated in a way nobody is managing. A grantor trust owns 20% of the stock. That means a stock sale requires trustee consent and separate counsel for the trustee (a genuine conflict, since the trust and Ken are on opposite sides of price and terms), the note must be addressed, and the trust's tax status affects the choice between a stock sale and an asset sale.
4. The succession conflict is unresolved and now public. The son has told the general manager he expects to take over. Any buyer will discover this in diligence, read it as a retention risk on the operations team, and use it to push price.

First five actions:

1. Freeze the broker's outreach. Determine exactly what was sent, to whom, and under what confidentiality terms. Build a leak protocol and a single approved talking point.
2. Take the quarterback role in writing. One engagement letter, one scope, one decision calendar. Advisors report through a coordinated work plan; each keeps their own professional accountability, but sequencing and information flow are centralized.
3. Get an independent valuation and a QoE as common ground. The $12M vs. $9–10M fight dissolves when both advisors are arguing about the same defensible EBITDA rather than about their own instincts.
4. Force the son conversation now, privately, before it reaches a buyer. Options are: he buys (unlikely without capital), he stays as an employee of a new owner, or he exits. Ken must choose and say it out loud.
5. Bring the estate attorney and trustee's counsel into the transaction design immediately - before any letter of intent defines the deal as a stock sale.

Treat it as a valuation-range problem, not a dispute. Both numbers can be true under different assumptions; the broker is quoting a price the market pays for a company that has done the preparation work, and the M&A advisor is quoting a price for the company as it stands today. That gap is the to-do list, not a disagreement.

Mechanism:

1. Commission one independent valuation (or a formal QoE plus a defensible market multiple range) and require both advisors to argue their number against that document. You have converted a personality conflict into an analytical one.
2. Build a bridge table. What specific changes would move defensible EBITDA from X to Y and the multiple from A to B? Management depth, customer contracts, financial statement quality, a second-in-command, documented systems. Assign a dollar value and a timeline to each.
3. Test the broker's $12M against real evidence. Ask for closed comparables in this sector and size band with the multiples actually achieved, plus the structure - because a headline 7x with a 30% earnout and a 24-month escrow is not $12M.
4. Then reframe for Ken: "The number is not 9 and it is not 12. It is 9.5 today and 11.5 in eighteen months if you execute these four items. That's a $2M decision about how you spend the next year."

What to do about the broker: do not fire on the basis of the number. Evaluate on process quality - the 40-buyer teaser with no NDA, no QoE, and no coordination with the estate plan is a legitimate performance issue. If the relationship survives, narrow the scope: marketing only, under a defined protocol, coordinated through the lead advisor.

What to avoid: letting Ken arbitrate between advisors based on who sounds more confident. Owners default to the highest number and the most flattering advisor; the quarterback's job is to make the decision rest on the document, not on the room.

Roles:

Party	Owns	Conflict to manage
Ken (owner)	Objectives, decisions, the family conversation	Wants the highest number and to avoid the son conversation
Lead advisor / quarterback	Work plan, sequencing, information flow, advisor coordination	Must not also be the sell-side fee-earner if objectivity is needed
M&A advisor	Valuation input, marketing, buyer management, negotiation	Paid on success; incentivized to close, not to advise "wait"
CPA	QoE support, tax modeling, personal returns	20-year relationship and personal returns create independence questions on the sell side; consider whether transaction tax work should go elsewhere
Transaction attorney	Deal structure, reps, escrow, employment agreement	None material
Estate attorney	Trust issues, note, gifting, post-sale estate plan	Drafted the IDGT; may defend prior work rather than test it
Trustee's counsel	Represents the 20% trust beneficiary	Genuinely adverse to Ken on price and terms - must be separate counsel
Wealth advisor	Personal financial readiness, post-sale allocation, liquidity plan	Has never done a transaction; scope must be defined before diligence starts

Sequence:

1. Months 0–2: Goals and readiness. Written objectives, personal financial gap analysis, family decision, engagement letters signed, broker outreach frozen and audited.
2. Months 2–4: Valuation and quality of earnings. Independent valuation, QoE, and the bridge table from today's number to the target number.
3. Months 4–9: Value preparation. Execute the highest-return fixes from the bridge table. Nothing goes to market until the financials survive diligence cleanly.
4. Months 4–6 (parallel, non-negotiable): Cap table and estate cleanup. Trustee consent mechanics, the note, whether the deal should be a stock or asset sale, and how the trust's interests are protected without derailing the sale. Get this settled before an LOI locks in a structure.
5. Months 9–12: Market. Controlled process, NDA-first, tiered buyer list, one voice.
6. Post-LOI: diligence, retention agreements for the GM and key staff, employment terms for Ken, escrow and R&W insurance, closing.

The quarterback's real deliverable: not harmony. A written plan that says who decides what, in what order, and what happens when two advisors disagree - with the owner's stated objectives as the tiebreaker.