Editor鈥檚 note: Changes have been made to reflect Ilona Sturm and her experiences more accurately.

Sometimes Ilona Sturm just wants to grab a beer and hang out. But ironically, the older she鈥檚 gotten, the harder it is for the to make plans with other people.

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One of her friends prefers to stay in and watch TV alone while another one has a significant other so she only makes time for date nights.

So, when Sturm is in the mood for a casual beer, she goes alone to or and brings her drawing pad along. For a writer and artist, she says, “it is critical to enjoy being alone.”

鈥淚鈥檓 57, but I still think like a 30 year old,鈥� Sturm said on a recent morning over the phone. 鈥淕od help the folks that are not artists and don鈥檛 have the inner resources to [be alone].鈥�

Sturm embodies what we鈥檝e seen as we鈥檝e delved into this topic for our Loneliness In Tech Series: first, that loneliness is a feeling to be managed, not necessarily combatted. Second, that in order to better understand isolation, we need to be open to being vulnerable and not confuse likes with affirmation and conversation.

However, although she鈥檚 following these rules, Sturm still struggles to have genuine interactions on a whim.

This leads us to our final topic for the series: Tech stepping in to make face-to-face interactions more human.

Face To Face

For some startups, there鈥檚 a in charging people to meet other people. After all, the addressable market of lonely individuals is quite high.

, for example, is a platform that connects women over the age of 50 for social events. It was part of the most recent batch, and it was started by and . Revel membership is currently free for inaugural members, but Marrone said members will eventually join for a $15 a month subscription.

Marrone, on stage at Y Combinator, said there are 50 million women over 50 in the United States alone. She added that these women have time, money, and energy to spend but nowhere to go.

鈥淚t鈥檚 all about meeting each other in the real world, because we know that that鈥檚 how people of all ages form the strongest connections,鈥� said Wahr. She added that all of her the organized gatherings are 10 women or less to keep them intimate.

As for events available, think decluttering workshops, printmaking workshops, a picnic by Lake Merritt, or, in Sturm鈥檚 case, a tour at the Museum of Modern Art in San Francisco.

Using Revel鈥檚 platform, Sturm hosted a tour at the museum on a recent Monday and four people showed up, including herself. The platform has been live in the Bay area for a month.

Other startups in this category include MyScoot, also a Y Combinator startup, which lets hosts throw parties and charge for attendance, and of course MeetUp, which was bought by WeWork in 2017 for $200 million.

But friendship requires more than just showing up, it means being genuine once you get there.

鈥淚f you are older and you go to a random meetup that isn鈥檛 super focused鈥� that鈥檚 the kind of vulnerability that will not pay off,鈥� said Sturm.

Inner Self

Taking a step back, in order for a community to be vulnerable, might come down to individual mindfulness to set the tone.

聽is a startup which sports the tagline 鈥渨e make being thoughtful easy.鈥� It鈥檚 defined as a 鈥渧irtual relationship assistant鈥� and helps users stay in touch with friends and families.

On the company鈥檚 website, it says that we鈥檙e all disconnected. 鈥淐onstant availability gives the illusion of connection. Online shopping, on-demand streaming, and working from home all corrode opportunities for human interaction,鈥� the website reads.

To join, users complete a 15 minute 鈥渙nboarding chat鈥� where the company learns about you and important relationships in your life. Then you pick how much time you want to invest in those relationships every day, week, and month. The assistant sends reminders such as call home regularly, chat with a friend even if there鈥檚 a time difference, and plan a birthday gift in advance. It charges $20 dollars a month, .

There鈥檚 also that encourages 鈥渄igital wellness鈥� by having users spend more time away from their phones. Users can track the progress of phone usage while studying, sleeping, or working, said , the co-founder and CEO of the startup.

Flipd has also started partnering with wellness content creators to host music, sleep stories, and meditation. Other startups that help with the latter category include , , and Wave.

Harvey thinks Flipd can help with loneliness.

鈥淲hen you’re constantly reminded that everyone on the internet is living their best lives and you’re at home scrolling on the couch, the best thing you can do for yourself is to get off your phone and engage your mind and body in another activity,鈥� she said.

A Mix Of Both

, a community manager with , thinks both in-person interaction and mindfulness apps aren鈥檛 the perfect solution. Yet.

While at the University of Pennsylvania, Bian started hosting gatherings for strangers to meet each other in three hour blocks. The time period was key: 鈥淚 think you need at least three hours for people to physically feel away, and create the energy of an alternate environment.鈥�

While Bian thinks startups like and Revel are helpful, she also said they aren鈥檛 a 鈥渃omprehensive enough solution for building a socially connected future.鈥�

鈥淭hese companies do an amazing job for creating opportunities for connection, but what鈥檚 lacking is having real connection be a value.鈥� Part of the reason, Bian said, is rooted in American culture.

We need a 鈥渧alue system that is about connecting and have connection be a value,鈥� she said.

In her observation, community leaders should be responsible for facilitating that value.

鈥淚f we鈥檙e talking tactically, [it鈥檚 about] the lighting, the mood, the sound, and the ambiance when you first step in the room,鈥� Bian said. The first 10 minutes sets the tone for how the conversation should go.

Circling back to Sturm. She鈥檚 been thinking of moving to Europe for the more casual culture. Until that day, however, she鈥檚 optimistic.

鈥淟oneliness is one way of interpreting an empty feeling,鈥� Sturm said. 鈥淏ut that empty feeling can also be turned into something that is very meaningful, if we don鈥檛 stop at the initial feeling of it.鈥�

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The poet once wrote: 鈥淭he irony about loneliness is we all feel it at the same time.鈥�

I imagine that , , and other leaders of social media would like to think of their platforms as a refuge for this human condition. After all, windows into each other’s lives have never been easier to look through. has 2.4 billion users who connect and share. , another Facebook-owned property, has .

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Despite those massive user numbers, data tells us we鈥檙e the loneliest we鈥檝e ever been. In fact, the more online you are, the more likely it is that you actually feel alone.

Some of the blame for loneliness is the omni-present like button鈥攁n app feature some confuse for actual affirmation. For others, digital socializing is a contradiction in itself.

鈥淪ocial media has failed in its promise of being social,鈥� said , the founder of , a conversation platform he said is built 鈥渢o help people to rediscover and reconnect over conversations.鈥�

鈥淭he true promise of social media,鈥� he said, 鈥渃an only be realized through real conversations.鈥�

Shah鈥檚 app helps people chat through spoken conversations, which he says are more intimate than the ones that could be had through keyboards or devices.

鈥淭he social apps of the world today have external validation and FOMO as their primary incentives,鈥� said , the , an app which lets individuals screenshare and video chat.

The game, she said, ends up being how we can all get the most likes, comments, and follows.

鈥淚t鈥檚 exhausting and depressing to constantly compare everyone else鈥檚 filtered lives to your own real life,鈥� she said.

Yet the largest social platforms in the world are slowing catching on to the inherent addictiveness of the apps they build.

A Filtered Lens

Instagram is rolling out a version of its app that removes the total number of likes on photos and video views. It is being tested in Australia, Brazil, Canada, Ireland, Italy, Japan, and New Zealand, according to , a spokesperson for Instagram.

鈥淲e are testing this because we want your followers to focus on the photos and videos you share, not how many likes they get. We don鈥檛 want Instagram to feel like a competition鈥搘e hope to learn whether this change can help people focus less on likes and more on telling their story,鈥� she added. The test began in Canada in May.

Of course, some users have found social media, as is, to be useful. , the CEO of , spends about 19 hours and 44 minutes a week on Twitter, according to his Screen Time app. 1

鈥淭he value of Twitter, for me, is the stuff that is on no one鈥檚 feed,鈥� he said. 鈥淚t鈥檚 the DMs that have been really valuable to me. I try to use it as a place where I can have conversations with people and be genuine and share my thoughts.鈥�

Through DMs turned into Zooms and phone calls, Twitter has given him friends in tech in Utah, San Francisco, and Los Angeles.

As for quality of conversation, money talk isn鈥檛 deep enough, Lavingia said. Talking about how hard it is to paint with the color green, however, is.

But having that deeper conversation requires a culture shift. It means relying on social media not for the affirmation but for the potential conversation. And it’s possible that culture shift, coupled with less addictive features, is the solution to loneliness induced by social media.

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Thirty minutes of meditation, fifteen minutes of a pep talk, and then a silent prayer service solely dedicated to founders seeking funding.

Founder Meditation was a weekly support group that , the CEO of , found comfort in after a potential co-founder stepped down for personal reasons.

鈥淲e鈥檇 have to explain what鈥檚 underneath us, why we鈥檙e tired,鈥� said TranPham on a recent Friday at . The meditation room was often full of other founders chatting about topics regarding how much time they spend with their spouses and differences in salary.

It was about 鈥渟haring in the suffering鈥� and feeling together, explained TranPham.

Then, after about three years, Founder Meditation shut down. According to TranPham, it was because the class got too popular, but there wasn’t enough space to host all the founders.

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TranPham still ended up starting a company, Reflect, to help people match with therapists that understand them. Yet even with a business targeted toward mental health, TranPham feels the pang of loneliness from time to time.

defines loneliness as a distressing feeling that comes when a person’s needs are not being met by the quality or quantity of social relationships. Another says that loneliness impacts .

Entrepreneurs, who are than a regular person to suffer from depression, bi-polar disorder, and suicidal thoughts, are no exception.

Vulnerability As A Solution

, founder of , a marketplace for digital goods, said that friendship takes vulnerability and time. He added: 鈥淚f loneliness is epidemic, this seems like an important part of the fix.”

Making friends seems to be a problem for adults everywhere.

Are we uncomfortable with spending time with people just because? Is it a base human thing to optimize how we spend our time, and with who?

Maybe being vulnerable comes up against evolutionary instinct.

鈥� Sahil Lavingia (@shl)

But that solution is complicated when applied to startup executives.

鈥淏eing a founder in itself is lonely, because you鈥檙e competing against so many other people,鈥� 鈥檚 told me in a recent interview. Due to that competition, “it鈥檚 hard for leadership to be vulnerable.鈥�

For , chief of staff at , an artificial intelligence startup, and Josh Taub, the vice president of product at Swyfft, a home insurance startup, a move to Baltimore presented a fresh opportunity to make friends.

The couple chose to live in a , featuring a one-acre amenity floor equipped with an open concept kitchen, hang out spaces, outdoor vegetable garden, pool, and double-sided TV.

So far, they鈥檝e started 鈥渓oose friendships over mixology and aromatherapy classes” hosted by their building. Movie night and late-night swim events are also on their calendars.

They said none of these activities feels forced. Many residents, according to the duo, are looking for the same experience.

For Optimization Sake

, a licensed clinical psychologist and professor at UCSF Medical School, and formerly head of Clinical Innovation at , works with tech founders and empathizes with clients since he was once a startup founder himself. He compared entrepreneurs to Olympic athletes: both groups need a coach to train their muscles while they compete, not just after they fail.

Most of Sepah’s clientele comes in search of 鈥減erformance optimization.鈥� That鈥檚 a fancy way of saying that some executives are realizing that working themselves to the bone is not productive. Coming to a psychologist for 鈥渙ptimization鈥� feels like a nod to the hustle culture mentality, which Sepah said can generally be a positive mindset if it’s balanced.

鈥淢y clients are high functioning, compared to the relative demographic of people I have seen in this community,鈥� he said. Before working with founders, Sepah worked with veterans in a hospital where many patients only sought help when symptoms became uncontrollable. He doesn鈥檛 advertise for his services. All of his patients come to him, often through referrals, because 鈥渢here鈥檚 a shortage of people doing this who are actually good at it.鈥�

That said, when he does sit across from a startup founder who is lonely, Sepah tells them he鈥檚 not going to change that state of mind.

鈥淚 wouldn鈥檛 try to fix their loneliness,鈥� he said. 鈥淭hose are normal human emotions and probably evolutionarily we evolved these for a reason鈥攖hey are useful signals to tell us something is wrong.鈥�

Instead of numbing or distracting the negative feelings of loneliness or sadness, Sepah urges founders to be critical about the crutches they use to avoid loneliness, such as drinking, social media, hyper-networking, or long work hours.

With this focus, his conversation with a distressed founder becomes less about how to cure loneliness, and more about how they can find find inspiration and a home within it.

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