TOC-23 Team Meeting — July 14, 2026
A full-day working session on clients, tools, positioning, growth, and what we do when the world changes.
TOC-South · 28 South Street, Hingham, MA · 0900 until finished · Dinner at Café TOSCA
Jim Machinchick · Phil Ierardi · Sam Stanton · Colin Fitzgibbons · Justin Graham · Hunter Steadley · Chris di Bonaventura · Matt Blind
One day, six working sessions
| Time | Session | The question on the table |
|---|---|---|
| 0900–1030 | 01 · Client Deep Dive — the Actively Managed Family Plan, family by family | Is every plan actually being actively managed — Plan / Portfolio / Performance / Pain? |
| 1045–1215 | 02 · TOC-23 Tools & AI Updates — framework, demos, security | Is the app stack compounding our advantage — and is client data safe inside it? |
| 1215–1300 | Lunch | — |
| 1300–1400 | 03 · TOC-23 Positioning — the Actively Managed Family Plan as our value proposition; differentiation, pricing, competition | When a stranger asks what TOC-23 is, do we all give the same answer? |
| 1400–1500 | 04 · Business Development — the 80/20 niche, the client portfolio, pipeline | Who exactly are we for — and does the client base diversify like a portfolio? |
| 1500–1600 | 05 · Team Goal Setting — financials, short- and long-term goals, personnel | What does winning look like by year end — and in ten years? |
| 1600–1700 | 06 · War-Gaming — eight scenarios, tested against history | When the scenario hits, what do we do in the first 30 days? |
Followed by dinner at Café TOSCA. Bring appetite — for both.
Client Deep Dive — 0900–1030
The Actively Managed Family Plan, one family at a time — with a TOC-Nilla run for each family on the roster.
The client is the coach. We are the quarterback.
The core of our value proposition. Every family of consequence already has excellent specialists. What almost no family has is someone whose only job is to keep those specialists coordinated — in real time, against a single definition of success.
Uncoordinated, the tax advisor optimizes taxes, the investment advisor optimizes returns, and the estate attorney optimizes documents — each locally right, collectively wrong. The gaps between them are where families lose money, usually in taxes.
One concrete play from the AMFP playbook: asset swapping between the inside and the outside of the estate — a move that only exists when the estate planner, tax advisor, and investment team are in the same huddle.
Asset swapping: put every dollar where the tax code treats it best
Seven families, four lenses each
For each family: Plan (is the estate & tax architecture current?), Portfolio (does the allocation still match the plan?), Performance (net of fees, vs. the family’s own objective), and Pain (what is quietly bothering them that they haven’t said out loud?). Target: a TOC-Nilla waterfall run for every family below.
| Family | Plan | Portfolio | Performance | Pain | TOC-Nilla |
|---|---|---|---|---|---|
| Robbins | Review | Review | Review | Discuss | Run live |
| Blanchard | Review | Review | Review | Discuss | Run live |
| Fitzgibbons | Review | Review | Review | Discuss | Run live |
| Chou | Review | Review | Review | Discuss | Run live |
| Fitton | Review | — | — | Discuss | If time allows |
| Annarelli | Review | Review | Review | Discuss | Run live |
| Lacrosse | Review | Review | Review | Discuss | Run live |
Discipline to close the session: every family leaves with at least one proactive action — an idea we bring to them before they ask.
TOC-23 Tools & AI Updates — 1045–1215
The application stack, live demos, the data warehouse, the gaps — and an honest conversation about security and privacy.
Asymmetric tactics, applied — through technology
The same framework we show clients is how we run the session: one secured data lake as the single source of truth, TOC-Monitor orchestrating on top, sub-applications drawing from the middle. Every demo today should be judged against this map: does it feed the lake, draw from the lake, or float alone?
Demos, decisions, and the two gaps
App Portfolio & Demos
Walk the stack live: TOC-Folio, TOC-Nilla, TOC-Hedge, TOC-Cierge, Doc-Parser. For each: usage since last meeting, what broke, what clients actually touched.
Custom Pitch Examples
Review the “See Button” pitch flow. Decision on the table: is TOC-Posal sustainable as built — maintenance cost vs. the 8–12 hours it saves per proposal?
Data Warehouse
Status of the unified lake: what’s ingested, what still lives in spreadsheets, and what it takes to make the lake the only source of truth.
Risk Management GAP
No systematic risk layer today — exposure, concentration, and liquidity monitoring across families. Scope what “minimum viable” looks like and who owns it.
Client / Associate Dashboard GAP
The operational goal is a 4:1 client-to-associate ratio. That requires a dashboard expressing the AMFP per family. Define v1 scope and a build owner.
TOC-Cierge Status
Adoption update, open requests, and whether the concierge layer is ready to be a named part of the client pitch or stays internal for another quarter.
Client data in Claude & our hosted apps: the debate, then the policy
| The case for | The case against | |
|---|---|---|
| Strategy | AI leverage is the asymmetric tactic — it’s how eight people deliver SFO-depth service. | One breach at a firm our size is existential — there is no “incident response” for a family’s estate plan on the internet. |
| Vendor posture | Enterprise/API tiers of Claude don’t train on inputs, encrypt in transit and at rest, and carry SOC 2 Type II. Client data already sits with custodians and Addepar — this is vendor management, not a new category of risk. | Consumer accounts and shared Hostinger hosting are a different animal: SMB-grade infrastructure, thin contracts, unclear breach SLAs — and the custodian, unlike us, has a security team. |
| Regulatory | Nothing prohibits AI use; regulators expect written policies and vendor diligence — both achievable. | Reg S-P safeguards, notification duties, and fiduciary duty all apply — self-built apps on shared hosting are what an examiner circles in red. |
| Practical | TOC-Nilla and TOC-Posal need real balance-sheet structure to deliver value. | Prompt leakage and misconfiguration are operator errors — and we are the operators, with no security engineer. |
Green · proceed now
De-identified documents into TOC-Nilla and enterprise Claude. A trust document stripped of account numbers, asset values, and SSNs is structure, not identity — and structure is what the tools need.
Amber · with controls
Client-linked data in our hosted apps — only after migration off shared hosting, with MFA, logging, zero-retention agreements, and written client consent. Until then: de-identified only.
Red · never
Raw SSNs, account numbers, custodial credentials, or full statements into any consumer AI account or shared hosting — no exceptions, regardless of convenience.
The conclusion to ratify: de-identification captures nearly all of the AI upside while removing nearly all of the breach downside. We leave this session with the three-tier policy adopted and an owner named for the infrastructure migration.
TOC-23 Positioning — 1300–1400
The Actively Managed Family Plan as our value proposition — external positioning, differentiation, pricing, benchmarking, competition, and a review of existing marketing materials.
Our value proposition is the Actively Managed Family Plan
“We don’t apply our business model to you — we build it around you.” The Actively Managed Family Plan is how that promise is actually delivered: one quarterback, actively coordinating every dimension of the plan. Line by line, the way a family experiences it:
| Dimension | Typical PE-Backed MFO | TOC-23 |
|---|---|---|
| Ownership | PE sponsor on a 5–7 year exit clock | 100% client and employee owned — no outside capital, no fund life |
| North Star | EBITDA growth, AUM per advisor | Client retention and depth — we invest alongside you with personal capital |
| Portfolio | 4–6 standardized models off a menu | Single-family-office customization: bespoke allocation, SMAs, direct deals |
| Estate & Tax | Referred out, or thin in-house | Lead-advisor model, coordinating your attorney and CPA with investments in the room |
| Concierge | Out of scope | In scope — the aircraft, the property, the philanthropic vehicle. We figure it out. |
| Alignment | Sponsor wants the exit; advisor wants the earnout | The people who hold the equity sit across the table from you |
Three pillars, one sentence each
Business Development — 1400–1500
The 80/20 niche, the client base as a portfolio, minimums, TOC-Talk, pipeline, and trustee services.
Where could 80% of our effort go? A brainstorm, not a decision.
Generalists compete on price; specialists get referred. To make the brainstorm concrete, two worked examples of niches where our story could be unusually strong — offered to test the idea, not to pre-select the answer:
Family Office Executives
Why us: they know exactly what great looks like — they run it for someone else — but rarely get SFO-level service for their own balance sheet. They evaluate on substance, not brand, and they refer each other constantly.
Expertise-building plays: a TOC-Talk series “for the people who run family offices” · an annual benchmarking note on FO executive comp, deferred comp, and co-invest structures · a TOC-Nilla teardown offer (“bring your own estate; we’ll model it live”) · presence at FO executive forums as speakers, not sponsors · a referral loop with FO attorneys and recruiters.
Successful Franchisees
Why us: multi-unit operators are cash-flow rich, entity-heavy, and chronically under-planned — real estate, holdcos, and eventual roll-up exits create exactly the estate/tax/liquidity complexity the AMFP is built for.
Expertise-building plays: a playbook white paper — “From 5 units to 50: the franchisee’s balance sheet” · pre-exit planning content timed to franchisor consolidation waves · relationships with franchise attorneys, brokers, and brand development officers · a case study (anonymized) of an asset-swap + entity cleanup for an operator · a seat at franchisee association events in 1–2 chosen brands.
Also on the table from the agenda: pre-liquidity founders and Fidelity executives — and anything else the room surfaces. Goal for this hour: a longer list of candidate niches and the criteria we’d use to choose among them. No commitment today; the decision comes after we’ve pressure-tested the ideas.
Manage the client base the way we manage capital
The rest of the growth engine
Client / Prospect Profile
Be deliberate: write the profile down — complexity, entity count, liquidity horizon, temperament — and grade the current pipeline against it. A prospect that doesn’t fit the portfolio’s target weights is a pass, even if the fee is good.
Minimums — FAQ
Agree on the public answer. Proposal to debate: a hard minimum for the “wealthy now” sleeve; a deliberately flexible structure for the venture sleeve, priced to convert at liquidity.
Brand Building: TOC-Talk
Cadence, format, and audience — pointed at the chosen niche, not at everyone. One great conversation a month beats four generic ones.
Pipeline Review
Walk the live pipeline by sleeve and by niche. For each: next action, owner, and date — and prune anything that has gone quiet for two quarters.
Trustee Services
Scope the opportunity: corporate trustee gaps among current families, what we can responsibly offer vs. refer, and whether it belongs in the administrative-services sleeve.
Four a year, for ten years
The long-term goal is 4 new clients per year. At target weights, that’s roughly 2 wealthy-now, 2 venture per year — the pipeline should be built and measured against that split.
Team Goal Setting — 1500–1600
A financial level set first — actuals through Q2 2026, projected through 2027, with and without the pipeline — then the goals that build on it.
The lines are converging — the question is when they cross
The expense mix is normalizing around people and technology
Compensation holds at roughly 60–63% of spend — a senior team is the product.
Technology’s share roughly doubles, 7% → 16% — the only line we deliberately grow, per the Session 02 strategy.
Legal & compliance normalizes from 23% → 6% as the 2025 formation-year spike rolls off.
Break-even is in sight — the pipeline decides the date
On existing clients alone, cash dips slightly negative around Q4 ’26–Q1 ’27 before recovering; with the pipeline, cash stays positive and ends 2027 near $440K. Converting the pipeline is what makes “no additional external financing” achievable.
Short-term: break even. Long-term: compound.
Investment
Define a quantifiable performance objective — and outperform it in 75% of quarterly reporting periods. The war-game session at 1600 is part of earning that number.
Operational
Build and execute the associate & client dashboard that expresses the Actively Managed Family Plan — the tool that makes a 4:1 client-to-associate ratio possible.
Direct Investment
Committed, credible sources and uses of capital: $25M in 3 years, $50M in 5 — higher-margin revenue (management fee + carry) than advisory, with incentives for external capital.
Personnel & Aspiration
TOC-23 forever — but it’s okay if you have different plans; mutual transparency is the rule. Standing question: what would make TOC-23 the greatest place any of us has ever worked?
Financial review to open the hour: revenue, costs, and trends since the last meeting — numbers on screen, no adjectives.
War-Gaming — 1600–1700
Eight scenarios. For each: the closest historical analog, what actually happened in the data, our pre-committed game plan, and the predicted result — so the plan is written before the phone rings.
How we war-game: history first, opinions second
1 · Anchor to an analog
Every scenario gets the closest historical episode — with real drawdown, duration, and recovery data. If we can’t name the analog, we don’t understand the scenario.
2 · Pre-commit the plays
For each scenario we write the first-30-days playbook now — rebalancing bands, tax harvesting, liquidity draws, client communication — so decisions under stress are executions, not debates.
3 · Predict the result
Apply the playbook to the analog’s data and estimate the outcome for a diversified TOC-23 growth allocation vs. a conventional 60/40 — directional, honest, and written down so we can grade ourselves later.
All figures on the next two slides are approximate historical references for internal discussion — not projections, not client material. Past performance does not predict future results.
When it breaks Defense
| Scenario | Historical analog & data | TOC-23 game plan (first 30 days) | Predicted result |
|---|---|---|---|
| Equities −30% to −50% | 2007–09 GFC: S&P 500 −57%, ~4 yrs to recover. 2000–02: −49%. 2020 COVID: −34% in 23 days, back in ~5 months. A 60/40 fell roughly −30% in the GFC. | Rebalance into equities at pre-set bands; harvest losses across every taxable account; execute Roth conversions and GRAT funding at depressed values; deploy into high-yield and distressed credit as spreads blow out — HY spreads hit ~2,000 bps in late 2008 and the asset class returned ~+58% in 2009. Detailed buying plan two slides ahead. | Diversified allocation (munis, hedge funds, real assets) drawdown meaningfully shallower than equity indices; harvested losses and depressed-value transfers turn the drawdown into a decade of tax alpha. |
| Geopolitical unraveling (Taiwan, Ukraine, Iran, terror) | Historically, event-driven selloffs are sharp but short: 9/11 — S&P ~−12% in a week, recovered within about a month; 2022 Ukraine invasion — initial drop, market bottomed later on rates, not the war. Median geopolitical drawdown historically in the −5–10% range with recovery in weeks-to-months. | Do not sell into the headline; confirm liquidity ladder covers 12+ months; add to energy/real-asset and defense-adjacent exposure per the analog; client letter within 72 hours with the historical table attached. | Short, sharp drawdown absorbed; the client letter is the real return — families who hear from us first don’t call anyone else. Persistent escalation shifts us to the inflation playbook. |
| Hyperinflation / AI bubble popping | 1973–74 stagflation: S&P ~−48%, gold and commodities surged, bonds punished. 2000–02 tech bust: Nasdaq −78%, but value/dividend equities were roughly flat-to-positive in 2000–01 — diversification worked. | Tilt to real assets, TIPS, and short-duration; underwrite every AI-adjacent position on cash flow, not narrative; rotate concentrated tech gains via exchange funds/collars before the pop, not after. | Real-asset sleeve and value tilt cushion the bust as in both analogs; the families hurt worst in 2000 were the ones who never diversified the concentrated position — that is the pain we pre-empt. |
| Liquidity crunch — 100% of committed capital called in 3 months | 2008–09: distributions stopped while calls continued; the denominator effect crushed over-allocated LPs — major endowments shopped PE secondaries at reported 20–40% discounts. | Stress-test every family now: unfunded commitments vs. liquid reserves; maintain a 2–3 year liquidity ladder per family; pre-arranged credit lines; be the secondary buyer at discounts, never the forced seller. | All calls met without selling equities at the low; families with dry powder pick up secondaries at the discounts the forced sellers create — the 2009 vintage was one of PE’s best. |
The standing theme across every scenario: position our families to be the liquidity providers when the market is starved for it — pre-set dry powder, secondary purchases at forced-seller discounts, credit deployed at panic spreads, and securities-backed lines (margin, used sparingly at pre-set LTV limits) so portfolios can buy without selling at the lows.
The −40% playbook: buy the panic, on a schedule written today
Trigger −20% · deploy 25% of dry powder
Broad equities at pre-set bands; harvest losses in every taxable account; begin Roth conversions.
Trigger −30% · deploy 25%
Add high-yield credit once spreads clear ~1,000 bps — equity-like return, senior in the capital structure.
Trigger −40% · deploy the final 50%
Equities, distressed credit, and PE secondaries from forced sellers; draw securities-backed lines at ≤10% LTV to buy without selling.
When it rips Offense
| Scenario | Historical analog & data | TOC-23 game plan (first 30 days) | Predicted result |
|---|---|---|---|
| IPO window broadly opens | 2020–21: record US issuance (~1,000 listings incl. SPACs in 2021); lockup expiries then met a 2022 bear — many founders round-tripped paper fortunes. | Sprint pre-liquidity planning for the venture sleeve: QSBS positioning, GRATs funded before the pop, charitable vehicles, 10b5-1 plans, and post-lockup hedging calendared on day one. | The venture-sleeve bet pays: pre-liquidity clients convert to full AMFP relationships, and — unlike the 2021 cohort — they keep the fortune because the plan preceded the pricing. |
| Market melt-up | 1995–99: S&P compounded roughly +28%/yr for five years; discipline felt foolish until March 2000, then it was the only thing that mattered. | Enforce rebalancing bands mechanically; collar or exchange-fund concentrated winners; resist late-cycle FOMO into richly priced privates; bank the gains into the liquidity ladder. | We lag the hottest index in the melt-up — by design — and keep most of it when the music stops; 75%-of-quarters objective is won across the full cycle, not in any single year. |
| Quantum computing breakthrough | Netscape, 1995: a single catalyst ignited a decade-long buildout — the durable winners (infrastructure, picks-and-shovels) mostly weren’t the first names to spike. Side risk: current encryption standards age fast. | Capture beta through broad indices first; selective direct exposure only via the direct-investment sleeve with real diligence; immediately review our own and vendors’ cryptographic posture (the security debate from Session 02 becomes urgent). | Participate in the buildout without single-name speculation; being early on post-quantum security is both a risk control and a credibility story for the tech-forward positioning. |
| Rate cuts, QE, mega peace deal | 1995 soft landing: S&P +34% that year. 2019 Fed pivot: +31%. Easing into a non-recessionary economy has been among the best historical setups for risk assets. | Stay fully invested to targets; extend fixed-income duration ahead of cuts; refinance or lock every client liability; accelerate any planned leverage while spreads are generous. | Portfolios ride the easing analogs’ tailwind; the liability side (mortgages, credit lines, deal financing) captures savings most advisors never touch — quarterback value, visible in dollars. |
“Anything above” — combined scenarios — default to the defensive playbook first: liquidity, then rebalancing, then offense. Approximate historical figures, internal discussion only.