True Ventures co-founder Jon Callaghan doesn’t think we’ll be using smartphones the way we do now in five years — and maybe not even in 10.

For a venture capitalist whose company has had some big winners in 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; this is a thesis on which True Ventures is actively betting.

The truth has never gotten this far by following the crowd. The firm has largely operated under the radar despite managing roughly $6 billion in 12 principal seed funds and four “select,” style funds it uses to pour more capital into portfolio companies that are gaining momentum. While other VCs grew more promotional – building personal brands on social media and podcasts to attract founders and deal flow – True went in the opposite direction, quietly cultivating a tight network of repeat founders. The strategy seems to be working: according to Callaghan, the company boasts 63 exits with gains and seven IPOs among a portfolio of about 300 companies gathered in its 20-year history.

Three of True’s four recent exits in the fourth quarter of 2025 involved returning founders who returned to work at the company again after previous successes, Callaghan said. However, 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 won’t be using iPhones for 10 years,” Callaghan said. “I don’t think we’ll use it in five years – or let’s say something different that’s safer – we’ll use it in different ways.”

His argument is simple: our phones are not good enough to be an interface between humans and intelligence. “The way we get them now to send a text to confirm it or send you a message or write an email – (that’s) not very efficient, (and) not a good interface,” he explained. “(They are) prone to error, prone to disruption (of) our normal life.”

So sure is he that True has spent 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 appeared, 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 away from him. Each time, the rust looked questionable, Callaghan said. Each time, the bet is on a new way for people to interact with technology that feels more natural than before.

The latest manifestation of this thesis is the Sandbar, a hardware device that Callaghan describes as a “mental companion” – or, in more mundane terms, a voice-activated ring worn on the index finger. Its sole purpose: capture and organize your thoughts through voice notes. It’s not trying to be another Humane AI Pin or compete with Oura’s health tracking. “It’s something really good,” Callaghan said. “But that one thing is a basic requirement of human behavior that is being lost in today’s technology.”

The idea is not to passively record ambient audio but to be there when an idea arises, serving as a kind of thought partner. It’s included in an app, uses AI, and, according to Callaghan, represents a very different philosophy of how we interact with intelligence.

What attracted True to Sandbar founders Mina Fahmi and Kirak Hong wasn’t just the product, though. “When we met Mina, we were completely aligned in vision,” recalls Callaghan. The True team has been thinking for years about alternative interfaces, making targeted investments around that possibility. They met with many founders, as a result. But the approach of Fahmi and Hong — who previously collaborated on neural interfaces at CTRL-Labs, a startup acquired by Meta in 2019 — stood out. “It’s about what (the ring) can do. It’s about the behavior it can do that we 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.” For some, the bike – even the earliest iteration – is enticing. But Peloton is really about the character it creates and the community it creates; the bicycle is the same ship.

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

Callaghan says True will raise more money to fund the operation, but he’s not interested in raising billions of dollars. “Like, why? You don’t need that to do something amazing right now.”

A similarly measured approach colors his view of the broader AI boom. While he says (when asked) that he believes OpenAI will soon be worth a trillion dollars, and while he calls it the most powerful compute wave we’ve ever seen, Callaghan sees warning signs in the circular financing deals backing hyperscalers and their $5 trillion in planned CapEx spending on data centers and chips. “We’re in a very capital intensive part of the cycle, and that’s worrying,” he said.

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

It all goes back to his core investment philosophy, which seems almost romantic — the kind of pitch-perfect VC wisdom that rings hollow from most people: “It should be scary and lonely and you should be called crazy,” Callaghan said of early-stage investing done right. “And it should be blurry and vague, but you should be with a team that you believe in.” After five to ten years, he said, you will know if you have something.

Either way, based on True’s track record of betting on hardware that many others have failed to do — fitness trackers, connected bikes, smart doorbells, and now mind-bending 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 roughly 2% per year, while wearables – smartwatches, rings, and voice-enabled devices – are expanding at double-digit rates.

Something is changing in how we want to interact with technology, and True is placing bets accordingly.

Pictured above, the Sandbar’s Stream ring. For more from our conversation with Callaghan, tune in to StrictlyVC Download podcast next week; New episodes drop every Tuesday.