Ollie is betting its focus on privacy can help it win the AI assistant race

Lennon is taking a different approach with Ollie. Currently, this family assistant connects to calendars and email to organize family schedules and keep its users updated about their days. It also offers tools that can help you plan meals, shop for groceries, track to-dos, book appointments, and pay bills via group chats. Later, it may help manage household budgets, too.

Yet, all this access requires trust, which Ollie claims, is its value-add compared to its rivals. “We’re not sharing your data with anyone. This is super sensitive, and that is necessary to win the trust of the users,” Lennon said.

In addition to the data protections provided by SOC 2 compliance, Ollie doesn’t request usernames or passwords to complete its tasks. When Ollie needs to log in to a website on the user’s behalf, it does so using its own browser in the cloud, and sends the user a link to a remote session in the browser. The process is similar when the assistant needs to make a payment or purchase on the user’s behalf.

While this method offers security, the downside is that users always have to log in to complete certain tasks. Still, that’s something Lennon believes technology will improve upon in time.

“This is… new territory. I think in the future, we will do some form of hard tokenization, in a secure way, so you’re not going to have to re-enter every time,” he said. “That’s frontier stuff… we want to find the right user experience that balances convenience and trust.”

Building that trust will be important before users trust Ollie to access more sensitive materials, like their bank accounts, even if that’s through a connector like Plaid.

Lennon, who has a PhD in AI, also has a background in fintech, having previously sold his startup Groundwork, a neobank for nonprofits, in 2021. That experience could help as Ollie moves further into money management.

Still, it’s not yet clear if people even want any of this assistance.

Lennon is hopeful, though, saying that Ollie’s retention curves are consistent with the leading AI subscriptions in terms of paid subscribers. (He didn’t share how many users or paid customers are now using Ollie, saying the space is too competitive.)

These systems can also be hit-or-miss at times. Despite the hype around Instinct, one of my first tests with it was to price out hotels then book one, and it quoted me all the wrong rates. Ollie, meanwhile, experienced an infrastructure outage with its text provider when I was testing it, and it stopped responding.

We asked the founder how Ollie is handling such problems, given that most consumers only give a new app or technology one shot. If it’s broken, they simply move on.

Lennon agreed this is an issue with AI overall. “This is the challenge with LLMs, in general — because they’re stochastic , they’re inherently unreliable,” he said. “We have to essentially build the harness — the agent harness — in a defensive way to catch and prevent those things… It’s almost like there’s just 1,000 cuts that you’ve got to solve first.”