Winding Down Olympia

On August 7, 2025, I began a 45-day wind-down of Olympia, an AI “virtual staffing” app built in Ruby on Rails. Ending something you’ve poured time and care into is never easy. I’m proud of what my team shipped, grateful to the customers who trusted us, and clear about the lessons I’m taking forward.

This post is a debrief focused on product, go-to-market, and company-building lessons. It’s not a legal brief or a play-by-play of personal conflict. Different people experienced the same moments differently; what follows is my perspective as the technical founder and investor. Importantly and contrary to her claims, the reason that I don’t fully name my co-founder Victoria when I discuss this story online is simply to protect her reputation, not to “erase” her from the story. Readers are invited to form their own conclusions.

What Olympia Was

Olympia offered a small team of role-based AI consultants — strategist, copywriter, legal expert — working in a shared workspace with memory, web tools, and light autonomy (e.g., link-reading, outbound email). Customers liked that the “team” remembered context over time and produced outcomes, not just advice.

What Worked (Product)

• Role-based collaboration lowered friction. Starting from a role beat starting from a blank chat.
• Memory compounded value. Long-term context (brand voice, in-flight work) kept people coming back.
• “Do it for me” > “tell me how.” Features like outbound email and link-following moved us toward real assistance.
• Show, don’t tell. Case-study flows and tutorials converted better than positioning pages.

What Didn’t Work (Reality Check)

• Distribution gravity favored incumbents. As soon as platform players shipped “build your own assistant,” much of the discovery surface moved inside their ecosystems.
• Platform velocity outran wrapper moats. Improvements in base models turned our differentiators into table stakes fast.
• Horizontal promise, vertical purchase. Our best stories were narrow (policy ops, launches, niche marketing), but our message stayed broad.
• First-mover advantage evaporated. We launched into the hype and peaked around $7.4k MRR (May 2024), then slid toward ~$1.9k by mid-2025 as the market flooded and our acquisition slowed.

Where I Set Us Up Poorly (Company-Building)

I optimized for convenience over structure. We ran through my existing LLC instead of forming a new company. That shortcut avoided legal overhead early but created ambiguity later: no vesting, no board, no tie-breaks, no written decision rights. I eventually signed a revenue-sharing agreement tied to a potential asset sale (50% of net sale proceeds if a sale closed) with my collaborator, but never replaced that with proper governance. Lesson: paper the company you intend to run, not the hope you intend to feel.

Titles outpaced scaffolding. I gave my collaborator a CEO title to build confidence. Without defined scope, decision rights, and coaching, a title became identity rather than accountability. That’s on me.

GTM doctrine stayed fuzzy. We needed a repeatable performance engine. Early paid tests fizzled; we defaulted to organic/community. Those channels matter over long horizons, but they were mismatched to an AI land-grab. If the thesis requires paid acquisition, instrument CAC/LTV, time-box spend, and staff it — or narrow the wedge and lower the burn.

Unequal draws + unclear expectations = friction. Any deviation from equal founder compensation should be explicit (salary, loan, or distribution) with terms. Otherwise, strategy debates feel personal.

Why We Wound Down (Short Version)

Recently a potential asset transaction fell through due to legal diligence cost/complexity. Leadership alignment wasn’t there, and I have full-time obligations elsewhere. Keeping Olympia in limbo just so that my collaborator could continue to keep the less than a thousand dollars a month in profit would have been unfair to customers. So I made the difficult decision to wind the product down: disable auto-renewals, pause new charges, provide export tools, set support timelines, and close accounts cleanly.

Documentation note: I keep contemporaneous records (email headers, calendar invites, call notes, finance charts) from this period and can share them confidentially with editors or mediators for verification. I’m not publishing private materials here.

What I’d Do Differently Next Time

Form an entity on day one. Issue founder stock with four-year vesting and a one-year cliff. Put IP and contracts in the company, not a personal LLC.

Don’t give someone completely unqualified for the role a hefty title like CEO just to help them build their resume or because you love them. That was my biggest and stupidest mistake.

Define roles and decisions early. Write down scope, decision rights, and tie-break mechanisms (e.g., an advisory board or named mediator). Titles follow the work.

Separate generosity from governance. If you help a collaborator financially, document it (salary/contract/loan) and keep it distinct from founder economics. I ended up giving my collaborator almost all the profit that the business ever generated, just because “I didn’t need it” compared to her. Instead of gratitude, I got spite and false accusations when things went south between us. There is such a thing as being too generous.

Declare GTM doctrine. If paid growth is required, staff it and time-box experiments. If you won’t fund that motion, right-size the ambition or focus on a narrow vertical with clear activation.

Set pivot gates. 30/60/90-day checkpoints tied to retention/activation. If the metrics miss, either narrow the wedge or sunset gracefully.

Ship plumbing early. Memory, retrieval, logging, export — make them boring and dependable. Trust compounds quietly; bugs spend it loudly.

Design for defaults. Meet users in the tools they already live in, or give a 10× reason to leave.

Assume the platform will ship your roadmap. Your edge must survive the next model release and the next store announcement.

Drift, Named Honestly

By late 2024 our cadence told the truth: sporadic posting, fewer launches, slipping focus. We didn’t fund a pivot, hibernate with integrity, sell quickly, or sunset on a timeline. That wasn’t malice; it was conflict-avoidance dressed as hope. The compassionate move would have been to decide — earlier.

A Word on Disputed Narratives

Different accounts exist about why a prospective transaction and a related hiring discussion didn’t proceed. I’m not litigating that here or anywhere else on social media. The only piece that matters to customers is this: we closed Olympia with care. If a journalist or mediator needs verification about the business sequence (diligence cost, dates, notices), I’ll provide documentation confidentially.

Gratitude

To everyone who tried Olympia, sent feedback at odd hours, and trusted an AI “team” with real work — thank you. To my collaborators: we pushed something super ambitious into the world. That’s worth celebrating. Even when we disagreed on direction, we were united by the hope that work could feel lighter.

What’s Next

My contract at Shopify ended recently, so I’m focusing on a vertical platform for specific industry workflows and a few tightly scoped Rails-plus-AI experiments. Same brief as always: pick a chronic pain, solve it end-to-end, and stay human about it. If that resonates, I’d love to talk.

Onward.