For a venture capitalist whose firm has had some big winners over its two decades – from consumer brands like Fitbit, Ring, and Peloton, to enterprise software makers HashiCorp and Duo Security – that’s more than armchair theorizing; it’s a thesis on which True Ventures is actively betting.

True hasn’t gotten this far by following the crowd. The Bay Area firm has largely operated under the radar despite managing roughly $6 billion across 12 core seed funds and four “select,” opportunity-style funds that it has used to pour more capital into portfolio companies that are gaining momentum. While other VCs have grown more promotional – building personal brands on social media and podcasts to attract founders and deal flow – True has gone in the opposite direction, quietly cultivating a tight network of repeat founders. The strategy seems to be working: according to Callaghan, the firm boasts 63 exits with gains and seven IPOs amid a portfolio of some 300 companies assembled over its 20-year history.

Three of True’s four recent exits in the fourth quarter of 2025 involved repeat founders who came back to work with the firm again after previous successes, says Callaghan. Still, it’s Callaghan’s thinking about the future of human-computer interaction that really stands out in a sea of AI hype and mega-rounds.

“We’re not going to be using iPhones in 10 years,” Callaghan says flatly. “I kind of don’t think we’ll be using them in five years – or let’s say something different that’s a little safer – we’re going to be using them in very different ways.”

His argument is simple: our phones are lousy at being the interface between humans and intelligence. “The way we take them out right now to send a text to confirm this or send you some message or write an email – [that’s] super inefficient, [and] not a great interface,” he explains. “[They’re] prone to error, prone to disruption [of] our normal lives.”

So sure is he of this that True has been spending years exploring alternative interfaces – software-based, hardware-based, everything in between. It’s the same instinct that led True to bet early on Fitbit before wearables were obvious, to invest in Peloton after hundreds of other VCs said ‘no thanks,’ and to back Ring when founder Jamie Siminoff kept running out of money and even the judges on “Shark Tank” turned him away. Each time, the bet looked questionable, says Callaghan. Each time, the bet was on a new way for humans to interact with technology that felt more natural than what came before.

The latest manifestation of this thesis is Sandbar, a hardware device that Callaghan describes as a “thought companion” — or, in more mundane terms, a voice-activated ring worn on the index finger. Its singular purpose: capturing and organizing your thoughts through voice notes. It’s not trying to be another Humane AI Pin or compete with Oura’s health tracking. “It does one thing really well,” Callaghan says. “But that one thing is a fundamental human behavioral need that is missing from technology today.”

The idea isn’t to passively record ambient audio but to be there when an idea strikes, serving as a kind of thought partner. It’s attached to an app, leverages AI, and, according to Callaghan, represents a very different philosophy about how we should interact with intelligence.

What drew True to Sandbar founders Mina Fahmi and Kirak Hong wasn’t just the product, though. “When we met Mina, we were just absolutely aligned on vision,” Callaghan recalls. True’s team had already been thinking for years about alternative interfaces, making targeted investments around that possibility. They’d met with dozens of founders, as a result. But the approach of Fahmi and Hong – who previously worked together on neural interfaces at CTRL-Labs, a startup acquired by Meta in 2019 – stood out. “It’s about what [the ring] enables. It’s about the behavior it enables that we will very soon realize we can’t live without.”

There’s an echo here of Callaghan’s old line about Peloton: “It’s not about the bike.” To some, the bike – even its earliest iteration – was compelling. But Peloton was really about the behavior it enabled and the community it created; the bike was just the vessel.

This philosophy of betting on new behaviors — not just new gadgets — also explains how True has managed to stay disciplined about capital. Even as AI startups raise hundreds of millions at billion-dollar valuations out of the gate, True insists that it’s able to stick to what it does best, which is to write seed checks of $3 million to $6 million for 15% to 20% ownership in startups that it often gets to see first.

Callaghan says True will raise more money to fund what’s working, but he’s not interested in raising billions of dollars. “Like, why? You don’t need that to build something amazing today.”

That same measured approach colors his view of the broader AI boom. While he says (when asked) that he believes OpenAI could soon be worth a trillion dollars, and while he calls this the most powerful compute wave we’ve seen, Callaghan sees warning signs in the circular financing deals backing hyperscalers and their $5 trillion in projected CapEx spending on data centers and chips. “We’re in a very capital intense part of the cycle, and that is worrisome,” he notes.

That said, he’s optimistic about where the real opportunities lie. Callaghan thinks the greatest value creation is ahead of us – not in the infrastructure layer but in the application layer, where new interfaces will enable entirely new behaviors.

It all comes back to his core investing philosophy, which sounds almost romantic — the kind of pitch-perfect VC wisdom that would ring hollow from most people: “It should be scary and lonely and you should be called crazy,” Callaghan says about early-stage investing done right. “And it should be really blurry and ambiguous, but you should be with a team that you really believe in.” Five to ten years later, he says, you’ll know if you were on to something.

Either way, based on True’s track record of betting on hardware that many others missed – fitness trackers, connected bikes, smart doorbells, and now thought-capturing rings – it’s worth paying attention when Callaghan says the phone’s days are numbered. Being early is the whole point — and the trend lines support his thesis: the smartphone market is effectively saturated, growing at barely 2% annually, while wearables — smartwatches, rings, and voice-enabled devices — are expanding at double-digit rates.

Something’s shifting in how we want to interact with technology, and True is placing its bets accordingly.