Why We’re DIY’ing Our ROBS (With AI) for Team Jellie Adventure Corp — And Not Paying a Middleman

Why We’re DIY’ing Our ROBS (With AI) for Team Jellie Adventure Corp — And Not Paying a Middleman

If you’ve ever explored funding a new business with retirement money, you’ve seen the acronym: ROBS — Rollover as Business Startups. It’s a perfectly legal way to move eligible retirement funds into a brand-new C corporation so the company can actually operate and grow. For Team Jellie Adventure Corp, our Michigan travel media startup, we’re putting $70,000 from Jason’s E-Trade 401(k) into the company now and leaving room to add another $70,000 in about six years.

Here’s the twist: we’re handling the structure ourselves with the help of our AI project instructions, templates, and automations—not a third-party ROBS promoter. Below is the full story—what ROBS is, how we’re implementing it, the exact guardrails we’re using, where the automation saves real effort, and why the DIY route makes sense for us.

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What a ROBS Actually Is (in plain English)

At its core, a ROBS does five things:

1. Create a C-Corp. For us that’s Team Jellie Adventure Corp in Michigan.

2. Adopt a qualified 401(k) plan for the company that allows rollovers and can invest in employer stock.

3. Move eligible retirement funds (via direct rollover) into the plan’s trust account.

4. Have the plan buy newly issued corporate stock (i.e., invest in Team Jellie Adventure Corp).

5. Put the purchase money into the company’s bank account so the business can actually operate.

It’s not a loophole, it’s not tax evasion, and it’s not “free money.” It’s your retirement capital investing in your company, with all the responsibility that implies. Your plan owns corporate stock; you then run a real business with actual compliance obligations.

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Why DIY? Our Decision Framework

We considered hiring a ROBS provider. Most of them are honest and useful. But we asked three questions:

Complexity: Is the compliance rocket-science, or “just” a lot of careful paperwork, calendars, and clean bookkeeping?

Control: Do we want deep, internal understanding of our structure—or to outsource that knowledge to a vendor?

Cost & Fit: Does an ongoing monthly service make sense when our company is intentionally lean and we’re comfortable documenting everything?

For us, the answers pointed to DIY—with help from AI playbooks, checklists, and auto-reminders. We’d rather invest our time once to learn the system properly than pay a recurring fee to be told when to file a form.

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Our Plan at a Glance

Entity: Team Jellie Adventure Corp (Michigan C-Corp)

Initial Funding: $70,000 from Jason’s E-Trade 401(k) via direct rollover to the corporate 401(k) plan

Plan: Team Jellie Adventure 401(k) Profit-Sharing Plan (permits employer stock)

Stock Structure: 100 authorized common shares at $1 par value (simple ledgering)

Initial Issuance: 100 shares purchased by the plan for $70,000 (books show $100 common + $69,900 APIC)

Operations: Jason is a salaried employee (reasonable compensation); no dividends; clean corporate books

Future Funding: A second, similarly documented round of $70,000 in ~6 years (we’ve already baked in reminders)

That’s the map. Now let’s talk about the road.

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The Minimalist ROBS Flow (How We’re Doing It)

1) Form the C-Corp (Michigan)

File Articles of Incorporation with LARA

Get the EIN

Adopt Bylaws and Organizational Minutes

Approve a Banking Resolution and open a corporate checking account (MSUFCU)

2) Adopt the 401(k) Plan & Trust

Plan document allows rollovers and employer stock

Appoint Jason as Plan Administrator and Trustee

Obtain/confirm a plan trust account and place an ERISA fidelity bond (target ≥10% of plan assets)

3) Move the Money (Direct Rollover)

The prior 401(k) custodian transfers to the plan trust (we issue a Rollover Acceptance Letter)

The prior plan issues a 1099-R with code G (trust-to-trust rollover)

4) Plan Buys Employer Stock

The Board authorizes the issuance in a formal resolution

We execute a Stock Subscription/Purchase Agreement

Issue Stock Certificate No. 001 to the plan’s trustee and update the stock ledger

5) Operate Like a Real Company

Cash from the stock purchase is now in the corporate account

We pay only legitimate business expenses, run payroll for Jason at a reasonable salary, and keep clean books

We maintain the plan for the exclusive benefit of participants (yes, that means we respect ERISA)

If that sounds like paperwork with some annual beats, you’re right. Which is why we leaned into AI to make it boringly reliable.

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Where AI Makes This Simpler (and Safer)

We built a lightweight “ROBS Project” inside our AI workspace, with:

Project Instructions (single source of truth): company facts, stock structure, plan details, operating policy (salaried Jason, no dividends), and filing calendar.

Document Templates: Organizational Minutes, Plan Adoption Resolution, Stock Issuance Resolution, Stock Subscription Agreement, Stock Certificate, Stock Ledger, Banking Resolution, Rollover Acceptance Letter, Annual Minutes, a 5500-EZ prep worksheet, and an annual valuation memo template.

Automations: reminders for:

May 15 — Michigan Annual Report

April 15 — Corporate tax return (Form 1120)

July 31 — Form 5500-EZ (file every year)

Annual — ERISA bond check/renewal, annual minutes, valuation memo

Year-6 — Second-funding workflow kickoff (90 days prior)

With those in place, the “compliance problem” becomes a calendar problem, and a calendar problem becomes an automation problem. That’s our sweet spot.

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Risk, Reality, and Guardrails (Important!)

DIY doesn’t mean do-whatever. We set non-negotiable guardrails:

Reasonable Compensation. Jason is on payroll as an employee. We’re not using corporate funds for personal expenses.

No Dividends. We reinvest or pay reasonable salary; we’re not distributing earnings while the plan is a significant owner.

Strict Segregation. Plan assets are plan assets; company assets are company assets. The plan holds employer stock (plus incidental cash).

Documentation Discipline. Every stock issuance, valuation memo, and minute is filed in a binder (and backed up).

Annual Filings. We treat 1120 and 5500-EZ as hard deadlines, not soft suggestions.

Could you get all of this wrong without realizing it? Sure. That’s why our AI setup treats the annual cycle like a flight checklist: repeatable, time-bound, and auditable.

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Why Not Hire a ROBS Provider?

Short answer: because our needs are simple, we’re comfortable with documentation, and we want to internalize the knowledge.

Longer answer:

We value mastery. We want to know exactly how our capital structure works and why. If the person who understands your company best is a vendor, that’s a dependency—sometimes necessary, sometimes not. In our case, not.

We prefer one-time setup, not monthly fees. Many services bundle documents, plan adoption, and reminders. Helpful, but we’ve now generated our own high-quality templates and embedded the reminders ourselves.

We already operate with tight creative workflows. Our content business lives on repeatable processes—scripts, templates, project boards. Building a compliance lane beside those isn’t a stretch; it’s an extension of how we run everything.

Transparency beats mystery. We’d rather read the rules and follow them than treat compliance as a black box.

Is a provider wrong for everyone? Of course not. If your situation is complex (multiple employees on day one, acquisitions, unusual plan eligibility questions), a specialized advisor may be well worth it. We simply don’t need that level of hand-holding for our scope.

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“But What If You Miss Something?”

That’s the most common pushback. Here’s how we designed against it:

1. Single Source of Truth: Our project sheet locks in the plan facts (par value, share count, operating policy, calendar-year accounting).

2. Automated Reminders: We don’t rely on memory. Repeating dates are scheduled with nudges well ahead of deadlines.

3. Annual Valuation Memo: Each year we pin a memo to support the plan’s employer-stock value for Form 5500-EZ and internal governance.

4. Annual Minutes: We record the shareholder vote (the plan trustee voting plan shares) and board actions at year-end. This institutionalizes the review loop.

5. Binder Layout: Every document has a home. Articles, EIN letter, bylaws, minutes, resolutions, stock ledger, 1120, 5500-EZ, valuation memo, ERISA bond—each has a tab.

Could the law change? Yes. If the IRS or DOL update guidance, our AI project’s “watch” triggers will prompt a review. That’s the benefit of capturing the process once and adjusting it when the landscape shifts.

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Our Ethics and Intent

A ROBS structure imposes fiduciary reality: when the plan invests in our company, we take on a duty to operate for the exclusive benefit of plan participants and beneficiaries. That mindset doesn’t sit on a shelf; it’s in our daily operating choices. Reasonable salary. No funny business. Clean books. Documented valuations. We embrace that discipline because it forces us to be the kind of company we want to build anyway.

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The Second Funding Round (Year Six)

We’ve baked in the future:

Reminder at T-90 days

Board resolution template for a new issuance

Valuation memo update to support pricing

Stock certificate & ledger ready for the second entry

This “round two” readiness keeps us from reinventing the wheel later—and it sets today’s structure with tomorrow’s needs in mind.

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What We Actually Built (Artifacts You Can Touch)

To make this real, we produced a full stack of working documents:

Project Instruction Sheet (company facts, plan facts, calendar, triggers)

Organizational Minutes + Bylaws + Banking Resolution

Plan Adoption Resolution and Rollover Acceptance Letter

Stock Issuance Resolution, Stock Subscription/Purchase Agreement

Stock Certificate and Stock Ledger

Annual Board & Shareholder Minutes

Form 5500-EZ Prep Worksheet

Year-End Valuation Memo Template

Having these in place is empowering. It’s not theoretical compliance—it’s operational.

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The Real Payoff: Focus

We chose DIY because we want to focus: on travel storytelling, video production, writing, and the work of building a Michigan-born media brand. Our ROBS process is deliberately boring. It’s precise, repeatable, and done. If something needs attention, our reminders surface it. If something needs updating, our project instructions tell us where it lives and how it works.

That frees creative energy for the stuff only we can do.

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Should You DIY Yours?

DIY may fit if your plan is simple (few/no employees to start), you’re comfortable reading and following instructions, and you’re willing to keep a binder, a calendar, and a clean ledger.

Hire help if you have immediate employees to enroll, complex eligibility questions, acquisitions, or simply want a professional to quarterback the filings and stand between you and regulators. There’s no shame in that—just know what you’re buying.

For us, the combination of AI project scaffolding and a tight compliance loop is enough. We love the clarity and the control.

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Final Word (and Where to Follow Along)

We’re bootstrapping Team Jellie Adventure Corp the same way we do everything else: hands-on, organized, and with a sense of humor. If you want to see how this structure translates into road miles, cameras, edits, and stories from around Michigan and beyond, come hang out with us:

YouTube: https://bit.ly/447MHDH

Spotify (Deep Dive AI Podcast): https://bit.ly/41Vktg6

Subscribe on YouTube: http://bit.ly/44ArQcq

And hey—if you’re building something of your own, remember: systems set you free. Get the structure right, automate the boring parts, and go make the thing you actually care about.

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Quick Reference: Our Compliance Checklist

Entity & Plan

MI Articles filed, EIN obtained, Bylaws + Org Minutes adopted

Plan document adopted; Trustee/Administrator appointed

ERISA fidelity bond placed (≥10% of plan assets)

Funding & Stock

Direct rollover received (1099-R code G from prior custodian)

Board resolution for stock issuance

Stock Purchase Agreement executed

Stock Certificate issued to plan; Stock Ledger updated

Annual Rhythm

Apr 15: Form 1120 filed

May 15: MI Annual Report filed

Jul 31: Form 5500-EZ filed

ERISA bond confirmed/renewed

Annual Minutes recorded

Year-end Valuation Memo completed

Operating Policy

Jason on salary (reasonable comp)

No dividends; retain earnings or reinvest

Strict plan/company segregation

Clean books; backup binder

That’s our playbook. DIY doesn’t mean alone—it means in control. With the right templates and automations, even “compliance” can be a calm lane in your creative highway.