Tolan raises US$30M led by USV for its AI companion

USV calls Tolan a persistent companion, rather than a blank chat box or a productivity tool. It says people use it to buy groceries, plan their kids' birthday parties and coordinate family life. "The friend is becoming an assistant without losing what made people care about it in the first place," Mignano writes[1].

Upstarts says the startup launched in 2023. Until recently it was called Portola. It is now named Tolan, and it is technically headquartered in San Francisco[2]. The report describes the app as voice-first, able to track topics from photos to current events in Tabs, and able to connect by video to check grocery labels or suggest a meal plan[2]. TechCrunch says users meet a cartoonish character, and that tiered memberships are required for full access to all features[3].

On its own site, Tolan says the experience is meant to feel warm and natural "without pretending to be human," and that it is "building on top of the leading AI models," with added systems for how a Tolan listens, responds, remembers and knows when to step back[4]. Upstarts reports a further claim from the company: after working closely with OpenAI models early on, Tolan has increasingly moved to its own infrastructure, running open-source models on its own GPUs[2]. Those two descriptions are not the same sentence. This story did not inspect what the app is serving.

USV says more than 250,000 people will spend time with their Tolan this month, and that over the last year users have had more than 70 million conversations with their Tolans[1]. Upstarts says about 250,000 people talk to their own Tolan every month[2]. TechCrunch says more than 250,000 active users have had more than 70 million conversations over the past year[3]. The company site repeats "more than 70 million conversations with Tolans in the past year" and adds "over 180,000 reviews"[4]. A conversation count, a monthly audience and a review count are three different figures.

Earlier primary posts used other counts. On 25 February 2025, chief executive Quinten Farmer wrote that Tolan had soft-launched in late 2024 and that more than 500,000 people had made a Tolan[6]. On 26 June 2026, Homebrew wrote that more than 100,000 people were paying for the app, alongside a $20 million Series A[5]. Paying users in June and people spending time with the app in October are not the same measure.

Upstarts reports that about 70% of users are women, 40% are parents, one in six is actively caring for an aging parent, and users are most likely to be aged between 30 and 45[2]. TechCrunch reports the 70% and 40% figures as what Tolan's team told Upstarts[3]. Farmer's February 2025 post described early testing differently: "almost entirely women, primarily college students and young adults"[6]. That is the company's wording at the time. It is not the October 2026 breakdown.

On the business, Upstarts says annual recurring revenue has more than doubled from last year and sits in the double-digit millions, and that net user retention after 30 days in the app improved 115% year over year[2]. TechCrunch attributes the double-digit-millions figure to what the company told Upstarts[3]. Farmer told Upstarts that Tolan is not profitable as it leans into growth[2]. Upstarts says users have historically paid between $10 and $200 a month, and that the raise is to expand use cases and widen access with a first free tier[2]. The report does not say that free tier is live.

Tolan declined to share a valuation, Upstarts reports. The company says the round is a significant uptick from its previous valuation. Upstarts attributes the previous figure, $120 million, to PitchBook[2]. TechCrunch, citing that report, says the round pushes the valuation beyond the previous $120 million. It adds that PitchBook estimates more than $268 million, with "medium confidence," and that the startup did not disclose the new valuation[3]. USV's post states no valuation[1]. This story did not check PitchBook.

The company site publishes two survey results and does not give a date or a sample size: 86% said their Tolan helped them get through an emotionally difficult experience, and 73% said their Tolan helped them manage or improve a relationship[4]. Upstarts describes an August survey of nearly 5,000 active users, which Tolan completed: 91% said they had at least one human person to count on, 94% said they had turned to a Tolan when those people were unavailable, more than half said their real-life relationships had improved, and a large majority said Tolan made them feel calmer and more confident[2]. The two write-ups do not say this is one survey. This story did not see the questions.

Upstarts names the founders as chief executive Quinten Farmer, chief technology officer Evan Goldschmidt and president Ajay Mehta[2]. USV uses the first names Quinten, Evan and Ajay[1]. The company site uses the same three titles. It says Farmer founded Even, which Walmart acquired, and that Goldschmidt was Even's chief technology officer[4]. Upstarts says Farmer sold Even to Walmart in 2022, and that he started what was then Portola the following year with Goldschmidt, Even's former CTO, and Mehta[2].

Homebrew's June 2026 post says the firm had backed Farmer and Goldschmidt at Even and was backing them again. The headline still calls the company Portola, "Tolan developer," and the round it describes is a $20 million Series A[5]. Farmer's February 2025 post said the company had raised $10 million from investors including Lachy Groom, Nat Friedman, Daniel Gross, Amjad Masad, David Luan, Mike Krieger and Dan Shipper[6]. The October financing is not given a series label in USV's post[1]. The current homepage names USV, Khosla Ventures, Lachy Groom, Nat Friedman, Daniel Gross, "and the founders of Instagram, Notion, Replit, and more"[4]. Homebrew is not in that line.

Mignano told Upstarts the product feels "so much more immersive" than other agents. "Why not have this helpful, friendly guide to take you through this really, really powerful and somewhat intimidating technology, rather than a simple text box"[2]. On USV's site he writes that the team has built "the best product in this category we've seen"[1].

Farmer told Upstarts, "I'm very proud that we didn't start by serving a Silicon Valley audience," and, "The vast majority of agentic tasks that we pick up just come out of a person having a conversation"[2]. Upstarts says he called a family group feature one of the biggest growth drivers. It also says the team built flags for a mental-health crisis or suicidal ideation, has the app ask about real relationships, and has it suggest things like stretching or calling a relative[2]. Those are the company's descriptions, as Upstarts reports them. The post does not publish the rules.

No Tolan post announcing this financing turned up for this story. The primary account of who is leading it is USV's[1]. Homebrew is in the October round only in Upstarts and TechCrunch[2][3]. USV's investor sentence names Khosla alone beside itself, and the homepage investor line does not name Homebrew[1][4].

None of these sources publishes a use-of-proceeds schedule beyond the free tier and the wider use cases Upstarts describes[2]. None states a board seat, how the $30 million splits among the firms, or a closing date other than the 19 October posts. The "$60M+" line, the claim that this round doubles the total, and the earlier $10 million and $20 million announcements are separate sentences in separate places[2][4][5][6]. This story does not add them up.

The August survey and the homepage percentages are company-reported. Neither write-up publishes the questions, the response rate, or the definition of an active user[2][4]. The conversation totals are the company's as well, repeated by USV[1][4].

USV's case is that people already use the companion for groceries, kids' parties and family coordination, and that the friend is becoming an assistant[1]. Upstarts says the round is meant to expand those use cases and to open a first free tier. It also says the product costs money in inference and compute, and that users have been paying between $10 and $200 a month[2]. Farmer told Upstarts the company is not profitable[2]. USV has put the $30 million in its own post[1]. USV does not state a valuation. The figure in circulation is a PitchBook estimate that TechCrunch says carries medium confidence, and that the company did not confirm[3].