Separated — WealthCo RIA + DealCo SPV sponsor

The founders own HoldCo, which owns three operating entities plus the connective layer:

• WealthCo — the RIA. Its own Form ADV, CCO, books, and cap table. Sean is CIO here, and only here; it advises separate accounts for an advisory fee on AUM.
• DealCo — the SPV sponsor. Its own adviser registration (typically an ERA under Advisers Act 203(m)), its own investment principal and IC, its own cap table. It sponsors and advises the SPVs and funds; carry flows to its GP entities. Sean does not advise here.
• MediaCo / MarketplaceCo — the creator media, events, and marketplace P&L — held outside both advisers.
• The funnel, papered as a durable, conveyable referral-and-data agreement that routes DealCo participants into WealthCo as wealth clients, so the customer-acquisition advantage survives a future sale.

The two advisers are genuinely separate — separate ADVs, separate ICs, separate key personnel including Sean RIA-only — which is precisely what avoids the integration collapse and delivers the clean, independently sellable RIA. The red-team review affirmatively credits this: a properly separated sister adviser that neither controls nor is controlled by the RIA is generally not an advisory affiliate, so DealCo's entity-level events do not auto-hit the RIA's Form ADV.

Heavier than Combined. You must add the SPV-side investment principal and IC lead, because Sean is now RIA-only and cannot be it — a senior, credible hire (the heavyweight IC the deal quality depends on), not a junior one. This single seat is the biggest team-cost difference between the two paths. WealthCo grows its advisor / IAR bench (wealth management is a headcount business; Sean cannot personally advise hundreds of households, and advisor dilution is a reason the separate cap tables are attractive — it should not eat the creator economics). DealCo grows its deal-operations owner and specialist sourcers. Compliance can share services carefully but has a wider surface across two advisers.

Higher. Two operating entities to capitalize and govern, more formation and structuring legal up front (inter-company agreements, separate registrations, the conveyable-funnel papering), the additional senior investment hire on the deal side, and — if you acquire a small RIA as the WealthCo chassis (recommended, because it hands you registration, a CCO, custody relationships, and a starter book on day one) — the acquisition cost. Order of magnitude: $5–8M+ to fund both entities through 24 months including the extra senior seat, or a staged version where each entity raises on its own timeline.

This is where separation earns its keep: you can raise the right capital from the right investors at the right multiple for each business, instead of blending them.

• WealthCo (RIA): a clean, recurring-revenue story for wealthtech investors, RIA aggregators, and PE, at a comparable multiple. Lower-risk capital, easy to price — and you can sell a minority stake without touching the deal business.
• DealCo (SPV sponsor): an alts-platform / GP-economics story for a different investor base, valued on fee-and-carry potential.

You still hold both under one HoldCo, so a single consolidated seed round is possible; separation is what preserves the option to raise each on its own terms later.

Higher total, if the funnel is preserved. The RIA is valued on terms the market already knows: roughly 2–4% of AUM, or 6–12x EBITDA, recurring, with a growth premium for the proprietary low-CAC funnel. A buyer of WealthCo also gets a CIO (Sean) dedicated fully to the RIA, which reads cleaner than a shared one and supports the premium. DealCo is valued separately on its own (lumpier, lower) economics, and its standalone value depends on the investment principal you hired to run it. The sum can exceed the blended combined valuation, because the market pays full price for the clean RIA instead of discounting it for the SPV risk surface. The condition is real: the funnel — and the shared brand — have to be contractually durable and conveyable HoldCo assets, or the RIA loses the growth premium.

Highest strategic flexibility: tune each business independently, set separate incentive pools (advisor dilution never touches creator economics), pursue separate fundraises and separate exits. The personal Sean-on-both conflict disappears because he is RIA-only, which is genuinely cleaner. The entity-level affiliated-allocation conflict — the RIA placing clients into the sister company's deals — remains, and is disclosed and managed by a written allocation policy plus consent and fee-offset mechanics. The cost is lower operational simplicity: two entities, inter-company agreements, a broader compliance surface, and data-sharing / consent mechanics on the funnel handoff.

Highest, and the strongest single argument for separation. Sell WealthCo into the deep, liquid RIA-aggregation market while keeping DealCo, or sell each to its natural buyer, or sell at different times. The RIA is the liquid crown jewel you can monetize on its own schedule, and because the entities are distinct from day one there is no fire-drill carve-out when a buyer appears. One caveat carries the same weight as the funnel: if the brand is the flywheel and the brand is HoldCo-owned, a clean sale of the RIA alone has to convey the brand (or the buyer gets a de-branded RIA that has lost its acquisition engine) — so treat the brand, like the funnel, as a HoldCo asset with a defined disposition set up front.