Meet Roi: The surprise we had in store for Owen Rask

On Wednesday, I was on my way out of the office when Rask founder Owen Rask called me over to his desk.

We share an office with the Rask team, and we'd invited Owen to join our founder, Navarre Trousselot, for our Superintelligent Investor Workshop on Friday. We'd told him to turn up and be prepared for a surprise. Now he wanted a few tidbits. What were we going to show him? Was there anything he could do to get ready?

I told him it would be a bit of a surprise, but to just be his normal inquisitive self and put our secret to the test during the webinar.

Then I realised I'd probably said too much. I slipped away while Owen was still talking.

The secret was Roi, our new AI portfolio assistant. The plan was to show Owen what we'd been working on, starting with Scenarios. Then we'd surprise him with Roi and bring the two together: asking questions about a portfolio, modelling hypothetical trades and exploring the results through a conversation.

When we went live on 16 October, Owen told viewers he didn't know what Navarre was about to show him. He likened it to a live unboxing.

So, thankfully, I hadn't given the whole thing away.

We'd even prepared a spare thumbnail for the reaction I was expecting. Perhaps I'd set the bar a little high.

The first Navexa AI could only take us so far

More than a year ago, we introduced the first version of Navexa AI in another webinar with Owen and Navarre.

The idea was to let people ask questions about their portfolios in their own words. But as Navarre explained during this workshop, that first version was restrictive. It could handle the prompts we'd built for it. Ask a follow-up, and you could quickly reach a dead end.

That's a frustrating place for a conversation to stop. A chart might answer your first question and immediately give you three more. Why did that period look different? Which holdings contributed to the result? How does it compare with another portfolio?

This time, we rebuilt the assistant from scratch.

The work behind the surprise

Since joining Navexa, Nick Freemantle, our Chief Agent Officer, has helped bring Roi from a concept to a product we could put in front of Owen and everyone watching.

That has involved long hours, sweat, tears, Saluministi coffee visits and Guzman y Gomez lunches. Nick has worked on Roi during the long commute to and from the office, and on weekends. As Navarre described on the webinar, it began with a proof of concept and developed over months.

It's also been a team effort. We've spent hours testing different use cases, feeding back what worked and what didn't, writing help articles and working on how Roi communicates. Making it sound more human has been part of that work, alongside making its answers clearer and its actions easier to follow.

You see the result of all that work when someone asks a question, follows up and gets somewhere useful. That's what we wanted to put in front of Owen.

Owen brought the questions

Navarre began with Scenarios, then introduced Roi and started asking it questions about the demo account.

One request brought all the portfolios onto a single performance chart, with a separate line for each. Another compared a portfolio with multiple benchmarks. Then came a comparison of the latest 90 days with the two preceding 90-day periods, and a treemap showing holdings grouped by sector and sized by value.

The multiple-benchmark example struck a chord in the chat. One viewer wrote:

Owen also asked what would happen if he asked Roi whether he should buy BHP. It was a useful question about the assistant's boundaries, and Navarre explained that the team was still stress-testing those safeguards ahead of release. Looking at your recorded portfolio data and asking for a recommendation to buy a particular share are different requests.

Navexa's calculation tools supplied the portfolio figures in the demonstration, while the AI interpreted requests and presented responses. The underlying records and settings still matter, and AI-generated explanations need checking.

Bringing Roi and Scenarios together

The Scenarios walkthrough compared three hypothetical sets of trades. Each produced similar cash proceeds, but the estimated capital gains or losses and the portfolio allocations left behind were different.

People watching wanted to get into the details. Could they choose which parcels a scenario used? The walkthrough covered the portfolio's existing CGT method and manual parcel selection where that feature is available.

Later, Navarre returned to the scenarios through Roi. He described hypothetical trades in the chat and asked it to compare the results. This was the part we'd wanted to bring together: the modelling tools and a conversation that could use them.

You can explore a hypothetical change, inspect its estimated effects and save it to revisit. Modelling doesn't place an order with your broker or change your actual transaction records.

The practical questions mattered, too

The DRP example brought the conversation down to a task many customers will recognise. Navarre started by asking about dividend reinvestment, then asked Roi to enable DRP tracking for a holding in the demo account.

Roi asked which rounding method to use and presented the change for confirmation. Once Navarre confirmed it, the reinvestment trades appeared in the holding's records.

A viewer promptly asked: “You would still need to action DRP in the Share Registry though, right?”

Yes. Turning on DRP tracking in Navexa records an arrangement you've made elsewhere. Participation in the plan still needs to be arranged with the relevant share registry or provider.

Other questions covered working across portfolios, ETF overlap, data privacy and using Navexa through Claude or ChatGPT. Navarre explained that Roi uses external AI model providers to process information, and discussed the separate MCP connector for connecting portfolio data to external AI tools. ETF look-through and expanded diversification reporting were described as upcoming work.

These are the questions we need to keep answering as we bring Roi to customers: what it can do, what it needs to do better, and how it fits into the way people already manage their portfolios.

What happens next

Scenarios has been released and is available under Tax Reporting. Roi's release is targeted for Monday 19 October, subject to the remaining checks. Navarre described an initial 30-day period to learn from usage and feedback, with longer-term pricing and usage arrangements still being assessed.

For our team, getting Roi in front of people is the next part of the work. We want to hear where it helps, where it gets stuck and what questions people want to ask next.

Towards the end, Owen said the team could be proud of what we'd built. In the chat, one viewer also took a moment to acknowledge Nick's work on Roi. It was good to see the work behind the product getting a mention.

Thank you to everyone who joined us, asked questions and put the demos to the test. And thank you to Nick and the team for the work behind what you saw.

Owen got his answers on Friday. If you missed it, the full replay is above. You can judge for yourself whether I was right to keep quiet on Wednesday.

Navexa provides portfolio tracking and reporting tools. The demonstrations and examples are for educational purposes and do not constitute financial, investment or tax advice. Scenario results are estimates based on recorded data and selected settings. AI-generated responses may contain errors or omissions.