The Recommendation
Form a new Ohio single-member LLC. Skip Wyoming. Don't S-Corp until net profit clears ~$60K. Ship by mid-May.
Why Ohio: ORC §1706.342 makes the charging order the sole and exclusive remedy for creditors against an LLC member's interest — explicitly extending to single-member LLCs. Stronger than most states and roughly comparable to Wyoming. Plus $99 one-time filing fee, no annual report, no franchise tax. Ohio is genuinely one of the cheapest, cleanest LLC jurisdictions for an Ohio-resident operator.
Why Other Options Lose
- DBA inside Aspire Digital LLC: A "grief moment" lawsuit names Aspire. Aspire's existing client revenue, contracts, bank, Stripe history all become reachable. Wrong move for grief-adjacent failure mode.
- Wyoming/Delaware LLC: Ohio nexus still triggers Ohio CAT/registration. WY charging-order-magic doesn't follow you home. Two states' fees, two registered agents, no real protection gain.
- WY holdco + OH opco: Right structure for $1M+ ARR or real estate. Massive overkill for pre-revenue solo. Two tax returns, intercompany agreements. Convert later if scale warrants.
- S-Corp election at formation: Break-even is ~$50-60K of net profit. Below that, payroll service + 1120-S prep + unemployment tax eat the SE tax savings. Defer.
- Adding Jaime as 1% member: Unnecessary in Ohio (statute already protects SMLLCs). Adds Form 1065 + K-1 + ~$800-1,500 prep cost.
Asset Protection — Insurance
| Coverage | Annual cost | Carriers to quote |
|---|---|---|
| E&O / Professional Liability ($1M/$1M) | $800-1,500 | Hiscox, Hartford, Next, Coalition, Embroker |
| Cyber/Data Breach | $400-800 (often bundled) | Coalition (best bundle), Embroker |
| General Liability + BOP | $500-700 | Hiscox |
CRITICAL: Ask carrier explicitly: "Does this policy cover claims arising from automated/AI-generated communications?" Some 2024-vintage policies have AI carve-outs. Get it in writing.
Banking & Cards
- Business checking: Mercury. Free, opens in a day with EIN. Avoid Chase Business.
- Stripe: Separate account in EFD's EIN. Do NOT use Connect or sub-account on Aspire's Stripe — that defeats the entire entity-separation purpose.
- Business credit card: Delta SkyMiles Reserve Business Amex (if $75K+/yr spend) or Delta SkyMiles Gold Business ($0 first year). Apply in LLC name with EIN to build business credit.
- Sales tax: Stripe Tax or Anrok from Day 1. Auto-tracks economic nexus across states. ~0.5% of revenue.
- Bookkeeping: Separate QuickBooks Online file ($30/mo). Don't class-track inside Aspire's QBO.
30-Day Setup Checklist
| Day | Task | Cost |
|---|---|---|
| 1-3 | File Ohio Articles of Organization (online OH SOS Business Central). Registered agent: yourself = free, or Northwest = $125/yr. | $99 + opt $125 |
| 3 | EIN via IRS.gov | $0 |
| 4 | Open Mercury account with Articles + EIN | $0 |
| 4-7 | Engage business attorney (Operating Agreement, MSA, DPA, call-recording disclosure) | $800-1,200 |
| 7 | Quote E&O + Cyber from Coalition + Hiscox + Embroker. Bind by Day 14. | $1,200-2,000/yr |
| 7 | Open separate Stripe account in EFD's EIN | $0 |
| 14 | Apply Delta Reserve / Gold Business Amex in LLC name; QBO + Stripe Tax setup | $30/mo + 0.5% rev |
| 21 | Buy domain, deploy site, Google Workspace | $50/yr + $12/mo |
| 30 | Pre-launch dry run — sign yourself as $0 client, run intake-to-invoice flow | — |
| Day-1 cash out total | ~$3,200-4,500 | |
Synchrony HR Disclosure — DO THIS BEFORE LLC FORMATION
Funeral home AI receptionist is well outside SyF's payments perimeter. The risk isn't competitive — it's time/attention/IP policy. Topher must disclose in writing.
Five questions to ask SyF HR (in writing, get answer in writing):
- Does SyF's outside business activity policy require pre-approval, disclosure only, or neither for non-competing ventures?
- Is there a restricted-industries list? Does "AI/voice services to funeral homes" fall in any restricted category?
- Are there restrictions on using personal time/devices for outside business?
- Does my role/level require Compliance review in addition to HR sign-off?
- (Implied) Get the answer in writing — email — save it.
Save the response at memory/drawers/day-job/syf-outside-business-disclosure.md.
Full org structure detail (every clause, source URLs, attorney/CPA scope): memory/drawers/aspire-ventures/efd/org_structure.md