Five Founders With Exits Are Betting On Offline. Should You?

Brynn Putnam sold Mirror to Lululemon for $500 million. Tristan Walker sold Walker & Company to Procter & Gamble. Andy Dunn built Bonobos. Audrey Gelman built The Wing. Adam Neumann built WeWork.

All five are now running companies with the same pitch: get people off their screens and into the same room. TechCrunch laid out the pattern on September 20, and it has been circulating among founders all week.

Putnam's Board is a 24 inch touchscreen table that reads physical game pieces. Walker's Heirloom Craft is buying and scaling fine craft trade schools, starting with a leatherworking school in San Francisco. Dunn's Pie has become what he calls a social life operating system for run clubs and watch parties. Gelman runs an 11 room inn in the Hudson Valley that hosts murder mystery dinners. Neumann's Flow sells apartment living built around community.

When five people who have each guessed right once all guess the same way, it is worth asking what they see. It is also worth asking what they might be missing.

The timing has a few clear drivers.

The health data got loud. In mid 2025, the World Health Organization's Commission on Social Connection reported that about one in six people worldwide are affected by loneliness, and linked it to roughly 871,000 deaths a year. That is about 100 deaths an hour. The report also found the highest loneliness rates among teenagers.

Consumers say they want experiences. TechCrunch cites a Harris Poll for Marriott Bonvoy in which two thirds of Americans said they were prioritizing experiences over material purchases this year.

AI is changing what people want from work and free time. Walker told a StrictlyVC audience he started Heirloom partly out of worry that AI would take knowledge work and pull people apart. More than half of the capacity at Heirloom's first school is filled by young tech workers looking for what he calls a phones down creative outlet.

Put those together and you get a market that looks ready. Whether it is a venture scale market is a different question.

Board has the clearest public numbers. According to TechCrunch's June coverage of its $20 million Series A led by Union Square Ventures, the $399 device is in tens of thousands of homes, schools, hospitals and restaurants across all 50 states. The company says 85 percent of customers average 30 or more play sessions a month. Total funding is now about $35 million.

Pie has raised $24 million and has changed shape several times, from friend matching to event discovery to hubs for recurring groups. Gelman's inn has raised about $3.8 million. Heirloom has not disclosed funding. Flow is the outlier, with more than $450 million, mostly from Andreessen Horowitz.

Notice the spread. Four of the five are raising relatively modest amounts. That is not a lack of ambition. It reflects a real limit: getting strangers to show up for each other does not copy and paste the way code does.

Software gets cheaper per user as it grows. Most offline businesses do not. Every new location needs a lease, staff, insurance and a local community that has to be built by hand. Every event needs someone to run it.

That creates three hard questions for any founder in this space:

1. What is the unit? A room, a class, a device, a group? You need a unit you can count and repeat.
2. What does one unit earn, and what does it cost? If a single location or group does not make money on its own, more of them will not fix it.
3. What carries over from unit one to unit ten? Brand, software, trained staff, a playbook? Something has to make the tenth one easier than the first.

The founders in this story each answer the third question differently. Board sells hardware, so the unit is a device and the repeat engine is games. Heirloom is buying existing schools, so the unit is a school with students and a master teacher already in place. Pie is software for groups that already meet, which avoids owning rooms at all.

If you are a first time founder drawn to this space, you do not need a Mirror exit to test it. You need a model that matches your resources.

Model 1: Hardware or kit that creates gatherings. Board is the example. You sell an object that makes a group activity easier. Margins depend on manufacturing, but you do not run the rooms. This is capital heavy early and hard without experience in hardware.

Model 2: Software for groups that already exist. Pie's current direction. Run clubs, book clubs, supper clubs and faith groups already gather. You sell them tools for scheduling, payments and membership. This is the lightest on capital and the closest to normal startup economics.

Model 3: Roll up or franchise of proven local businesses. Heirloom's approach. Buy or partner with places that already have demand and a skilled teacher, then add booking, marketing and operations. This is slower, but each unit has proof before you buy it.

A fourth model, owning big physical spaces as Flow and WeWork do, tends to need very large capital and carries real estate risk. It is rarely a good first company.

The good news about offline businesses: you can validate them with almost no code.

Run one event, three times. Pick a format. A craft night, a game night, a walking group. Charge for it from the first session, even a small amount. Free events tell you people like free things.

Track repeat rate, not signups. The number that matters is how many people come back for the second and third session without being chased. Board's 30 sessions a month figure is powerful for the same reason.

Measure cost per head. Add up venue, supplies, your hours and marketing, then divide by attendees. Compare it to the ticket price. If you lose money at 20 people, doubling to 40 rarely saves you.

Ask what they would pay monthly. A membership tells you more about value than a one time ticket.

Keeping this data in one place helps. Some founders use a simple sheet. Others build it into a business plan in a tool like Foundra so the unit numbers sit next to the market and funding sections. Either way, write the numbers down after every session.

TechCrunch's own read was cautious: it is unclear whether togetherness becomes its own sizable investment category, because it is not as scalable as shipping software.

That tells you who is likely to write checks. Repeat founders get meetings because they have sold something before. A first time founder with the same idea will face a tougher room. So plan accordingly:

• Consider revenue based financing, small business loans or angel money if your model is local and profitable per unit.
• Pitch venture investors only if you can show a repeat engine, usually software or a brand, that makes growth cheaper over time.
• Lead with retention data. In this category, repeat attendance is the equivalent of net revenue retention.

A profitable network of ten locations can be a very good business without ever being a venture business. Decide which one you are building before you pick your investors.

One more thing to notice about the five founders in this story: each one built a real brand before. That history lowers the risk investors see. If you are starting without it, your substitute is proof. Paying customers who come back, a waitlist you did not buy with ads, and costs you can explain line by line will do more for you in a pitch meeting than a big vision about loneliness.

Which founders are building offline connection startups? TechCrunch highlighted Brynn Putnam (Board), Tristan Walker (Heirloom Craft), Andy Dunn (Pie), Audrey Gelman (The Six Bells Countryside Inn) and Adam Neumann (Flow).

Is loneliness really a market driver? The WHO Commission on Social Connection estimated in 2025 that about one in six people worldwide are affected and linked loneliness to roughly 871,000 deaths a year. That has pushed the topic into health policy and consumer spending.

Can a first time founder compete in this space? Yes, especially with lighter models like software for existing groups or small, profitable local formats. Expect venture investors to ask hard questions about scale.

What metric matters most? Repeat attendance. How many people come back without being chased tells you whether the gathering has real value.

How much money do I need to start? Often very little. You can test most formats with a rented room, supplies and a ticket link before building any product.

1. A small but growing number of founders are betting on bringing people together offline, TechCrunch, September 20, 2026
2. Board, the new game startup from Mirror founder Brynn Putnam, raises $20M, has already sold thousands, TechCrunch
3. Andy Dunn's startup Pie becomes less of an events app and more of a social network, TechCrunch
4. Social connection linked to improved health and reduced risk of early death, World Health Organization
5. Loneliness, Social Isolation Linked To 871,000 Annual Deaths, WHO Finds, Health Policy Watch