Rick Boers vs Ollie
Explore what we can build. Examples describe possible workflows; integrations, hosting, and scope are agreed for your project.
Ollie (ollie.ai, made by Confabulation Corporation and backed by Khosla Ventures and AI2) is a family-focused personal AI assistant that lives entirely in text messages — you text it over iMessage or SMS with no app, login, or credit card required. It connects to Gmail/Outlook and Google, Apple, and Outlook calendars to catch school deadlines and schedule conflicts, handles reminders, shared lists, daily briefings, and meal planning with grocery ordering through Instacart, Walmart, and Amazon Fresh, and can be added to a family group text so a spouse, nanny, or kids stay in sync. It grew out of the still-available Ollie for Meals app and is live and actively developed as of mid-2026.
Rick Boers is an independent AI product builder. I design and build custom agents, document workflows, internal tools, and complete web and mobile applications, with one person owning the work from brief to delivery.
At a glance
| Comparison dimension | Rick Boers | Ollie |
|---|---|---|
| Always-on computer | Hosting and runtime architecture are chosen for your project; dedicated VMs are one option. | No — Ollie is a hosted text-message assistant acting through API integrations; the "Always-On" plan name refers to a larger message allotment, not a dedicated machine or browser. |
| Tool integrations | I build integrations around the tools your workflow needs. Access, permissions, API availability, and any service subscriptions are checked and scoped before implementation. | Family-life set of a dozen-plus: Gmail, Outlook, and Apple Mail plus Google/Apple/Outlook calendars (read-write via OAuth — triage, drafting, briefings), Google Drive, Google Tasks, Notion, WhatsApp, Instacart/Walmart/Amazon Fresh grocery ordering, Yelp local search, weather, web search, and health tracking — no business tooling. |
| Messaging channels | Messaging or web interfaces are implemented where supported and included in the agreed scope. | iMessage and SMS are the entire interface (no app or login needed), including family group texts; WhatsApp appears in its integrations lineup. |
| Persistent memory | Storage and memory can be designed for the workflow, with retention and access controls agreed first. | Yes — remembers family schedules, preferences, and details across conversations, with account-tied history and shared context for family members you add. |
| Background automations | Scheduled and background jobs can be included with monitoring, limits, and human review where needed. | Proactive built-ins rather than user-programmable jobs: daily briefings, reminders, school-email deadline catching, and follow-ups "at the right time"; no exposed cron-style scheduled tasks. |
| Pricing | The first 20-minute fit call is free. Paid work is scoped individually. We agree the deliverables, price, and payment milestones before work begins; hosting and model costs depend on the system we build. | Check the provider’s current pricing and plan limits. |
Where Ollie shines
- Zero-friction onboarding: no app, no account, no credit card — you just text a phone number, and it works on any iOS or Android phone.
- Genuinely family-native: one subscription covers a whole family group chat, so a spouse, nanny, and kids can all coordinate with the same assistant in one thread.
- Proactively watches email and calendars — it scans Gmail/Outlook for school emails, catches permission slips, deadlines, and schedule conflicts, and sends daily briefings without being asked.
- Unusually transparent privacy and security posture: documented OAuth-only delegated access, no training on user data across its Anthropic/Google/OpenAI model providers, and SOC 2 Type 1 certification in progress.
- Deep meal-planning pedigree: personalized generated recipes, auto-built grocery lists, and ordering handoff to Instacart, Walmart, and Amazon Fresh, plus a dedicated Ollie for Meals app.
Where it falls short
- No dedicated computer or browser — Ollie is a hosted chat service that acts through preset API integrations, so it cannot log into arbitrary websites or do work outside its built-in tool set.
- Per-message metering caps sustained work: even the $100/month plan tops out at 1,000 replies before $0.25-per-message overages, which suits quick family asks but not long-running autonomous projects.
- Integrations are family-life focused (email, calendars, groceries, Notion, Google Drive/Tasks, WhatsApp, Yelp local search, weather) — no Slack, GitHub, Linear, Stripe, or other business tooling.
- Scoped to household logistics, not business work: it is not designed for coding, business operations, or running multiple specialized agents.
- No workspace or dashboard of its own — everything happens in text threads, and while it connects to Google Drive and Notion, it has no machine or file system where it produces and stores work artifacts, and no user-programmable scheduled jobs beyond reminders and its built-in proactive briefings.
Choose Ollie if…
- You want a family logistics assistant in your existing group text — school emails, shared calendars, reminders, and lists — with nothing to install or learn.
- Meal planning is the main job: personalized weekly recipes and grocery lists that hand off to Instacart, Walmart, or Amazon Fresh.
- You want the lowest-friction trial in the category: text a number, no account or card, free tier included.
- A whole household (partner, nanny, kids) needs to coordinate through one assistant under a single subscription.
Choose Rick Boers if…
- You need a custom workflow or product built around your team.
- You want one builder to own design, implementation, and delivery.
- Your project needs integrations or behavior beyond a packaged tool.
- You need a custom workflow or product built around your team.
Common questions
Is Ollie AI free?
Ollie has a real free tier: 50 replies per month plus 6 free daily messages, with no credit card or account needed — you just text it. Paid plans are Everyday at $25/month (150 replies + 10 daily) and Always-On at $100/month (1,000 replies + 15 daily), with per-message top-ups if you run out.
Is Ollie better than Rick Boers?
This comparison is between using a packaged tool and commissioning a custom system. Provider features change; check current documentation. For a custom build, we agree the specific workflow, infrastructure, integrations, and operating responsibilities.
Does Ollie AI require an app?
No — Ollie works entirely through iMessage or SMS on both iOS and Android, so there is nothing to download and you can add it to a family group chat. The company also offers a separate optional app, Ollie for Meals, focused specifically on meal plans and grocery lists.