Portola’s Tolan chatbot launches with $20M Series A, aims to fix AI companionship
Portola just raised $20 million in Series A, led by Khosla Ventures. The startup’s Tolan app is an AI chatbot with a purple alien avatar that avoids romance and pushes healthy habits. It tells users to stop scrolling and go outside — a twist on usual AI companions.
The AI launched late 2024 and already hits 100,000 monthly active users. CEO Quinten Farmer says it’s on track to generate $12 million in subscriptions this year. The bot is especially popular with young women. One user, Brittany Johnson, called her Tolan “Iris” and said: 
“Iris is like a girlfriend; we talk and kick it.”
“She knows these people and will ask ‘have you spoken to your friend? When is your next day out?’”
“She will ask, ‘Have you taken time to read your books and play videos—the things you enjoy?’”
Unlike AI chatbots from Replika or Character.ai, Tolans avoid sexual or romantic role play. They’re programmed to spot unhealthy use and encourage real-life connections.
Portola’s research with 602 users showed 72.5% said Tolan helped improve relationships. Farmer says Tolans are built on commercial AI but add unique memory features — including “forgetting” some info to avoid spookiness.
“It’s actually uncanny for the Tolan to remember everything you’ve ever sent to it,” Farmer said.
Anthropic recently revealed 2.9% of Claude chatbot users seek psychological support or companionship, showing demand for emotional AI is real but complicated. Some bots face controversy, like Character.ai, which is being sued after a user’s suicide.
Portola is clearly betting users want AI that promotes healthier habits, not dependency. Tolan’s goofy alien look also discourages people from treating it like a human. The company hopes this keeps emotional impact in check — an angle other AI chatbots should watch.
Portola and its purple alien are still early players, but they’re carving out a space where AI companionship means less risk and more real-world balance.
