Ashley Targuello is the co-founder and co-CEO of Can We App, a platform designed to move people from online interaction to in-person connection. Her path to building a tech product did not start in software. It started in sports, then moved through education and communications, and later into company building.
This post follows the themes discussed in the episode: career transitions, the problem Can We is trying to address, what “social navigation” means in practice, how Ashley thinks about community building, and how she approaches leadership.
Career transitions: openness over certainty
Ashley describes her early identity as rooted in basketball. She played Division I basketball for her first two years of college and later transferred to NYU. At NYU she studied international politics and languages and worked in public relations with the New York Rangers. After graduation, she moved to Miami.
She frames these shifts as the result of staying open rather than committing to a single fixed track early in life. She argues that people often treat college as the moment when they must decide their permanent direction, and she rejects that idea. Instead, she advises being willing to pivot.
“Be open to opportunity, be open to change, to pivot, to reinvent yourself.”
She also emphasizes not letting other people’s doubts decide what is worth starting. In the conversation, she references how others asked the host how a podcast would be monetized, and uses that example to underline her approach: begin, then learn.
“If that’s what you want, go for it. Break that wall down and don’t stop.”
The loneliness problem and why connection is the product
Can We App positions itself around a specific claim: loneliness is widespread and has consequences beyond mood or short-term well-being. Ashley says society is living through a period of high loneliness and that people often underestimate what that does to health.
“We’re currently living in the loneliest times ever.”
She links this to the broader mental health conversation and adds that loneliness affects physical health as well. She references Dan Buettner’s Blue Zones work and points to community as a common factor in long-lived populations. Her conclusion is that “connection” is not a soft benefit but a practical driver of better outcomes.
The app’s mission, as she describes it, is to improve quality of life by helping people connect in person.
“We use tech to get people off of tech.”
What “social navigation” means
Ashley draws a clear line between Can We and traditional social platforms. She says it is not a social media product and does not aim to keep users scrolling. Instead, she calls it “social navigation,” a category she describes as a tool that helps you move through your social life in the same way a GPS helps you move through a city.
“We’re not a social app. We call it social navigation.”
In practice, she explains the product in terms of communities, events, and introductions. Users can join or host events. The platform then makes suggestions and introductions based on shared interests and context, including whether two users are attending the same event. The intent is to nudge people toward meeting offline.
She describes the longer-term vision as a utility you open when you want to connect where you are: at a coffee shop, at the gym, or in your neighborhood.
One example she gives is how people can live close to each other without knowing one another.
“They’re walking their dog alone and so is their neighbor… They don’t know anyone.”
The concept is not only “find people,” but “reduce the friction of starting.” The system introduces people and provides a reason to speak in person.
Community building as a strategy, not a side effect
Ashley talks about community building as both an outcome and a deliberate method. She hosts women-focused events, but she says the product is not limited to women. She describes those events as partly marketing and partly a way to gather people in a format that supports connection.
Her definition of community is functional: people being introduced, speaking, and leaving with new relationships. She contrasts that with events where attendees only talk to the friends they arrived with or focus on appearances and photos. In her view, those do not create community.
A recurring theme in her comments is that many people do not know how to initiate conversation anymore, especially with strangers. That is where structure matters: a host who introduces people, prompts that start conversations, and formats that reduce the social barrier to participation.
“People don’t know how to connect anymore.”
She also uses the phrase “friend in common” as a model: a trusted intermediary who makes introductions and gives people permission to follow through. In the app, that intermediary is the product itself, which suggests who to meet and why.
On event size, she says she prefers smaller gatherings (around 40 people) for her own events, but also describes larger events working when they break into smaller interest-based groups. The central point is not the total headcount. It is whether people end up in smaller, relevant clusters where conversation can start.
Leadership: empathy plus standards
Ashley describes leadership as personal attention combined with clear expectations. She gives examples of checking in with employees about how they are doing and creating what she calls a family environment. She frames care as part of building trust and retention.
At the same time, she stresses that work still needs to move.
“If I say something needs to get done, it better get done.”
In her framing, empathy and accountability are not competing ideas. Empathy helps build trust and communication; standards set what execution looks like.
She also co-leads the company with her husband. She says people often ask how that works, and she describes the partnership as an extension of operating as a team in marriage and parenting. In her view, the shared goal and shared responsibility make the work relationship more direct rather than more complicated.
“We’re one team. We have one goal.”
Presence and personal style: function over labels
The conversation also covers how she thinks about presence, confidence, and leadership, particularly for women in tech. She connects personal style and body language to how someone carries themselves in professional settings. Her point is not that the clothing itself creates authority, but that the signal matters.
“It’s really just the way you carry yourself.”
She also argues that style is not defined by price and mentions mixing affordable items with higher-end pieces. In her examples, a blazer functions as a practical “go-to” uniform that can work across settings.
Growth approach and what comes next
On expansion, Ashley describes a geographic strategy: build density in one location first, then expand outward. She names South Florida as the target area to “own” before spreading into adjacent markets.
She also references activations outside Florida, including events in the Dominican Republic and Paris, and a launch connected to Necker Island with Richard Branson. These examples are mentioned as proof that the concept can travel, but her stated plan prioritizes local concentration first.
She hints at a future deal planned for 2026 but does not share details in the episode.
She frames the overall trajectory as early-stage momentum.
“This is just the beginning.”
A practical takeaway
Ashley’s view of community is operational: create the conditions for people to talk, remove friction from introductions, and design for offline follow-through. In that framing, the product is not only the app. The product is the connection that happens after the app.
If Can We succeeds on its own definition, it will be measured less by time spent in the interface and more by how often people leave it to meet someone in person.
“We use tech to get people off of tech.”
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