Laid Off: And Building Her Own Coworking Space
"I’m making lemonade with my own spin. Ya’ll will have to stick around to see what I’m mixing up in the kitchen."
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In today’s issue, I talk to Michelene Wilkerson, who worked in community programming at The Wing and Round. After being laid off last year, she’s decided to build her own community space in Brooklyn.
Michelene Wilkerson, 30, started working at The Wing as a front desk employee seven years ago. The social club for women was the subject of a New York Times exposé in 2020 — it was cast as merely an illusion of feminist empowerment.
That same year, The Wing announced mass layoffs. And in 2022, it shut down.
Michelene started working as the programming and content manager at Round, a professional network for tech leaders, in 2023. She was laid off in April 2024 when the company shut down operations.
She has seen the guts of exclusive community spaces, the inspired and the ugly bits. And now she’s fulfilling a decade-long dream of starting her own business: a forthcoming member space in Brooklyn called Openspace.
”Working at The Wing showed me how purpose-driven companies can go left during hypergrowth, both in culture and scale,” Michelene said. “Round showed me what it looks like when a startup cannot find product market fit. In hindsight, I feel better positioned to build Openspace because I’ve seen what can happen at both extremes of venture-backed community businesses.”
How did Round handle layoffs?
The day started like any other day, but our weekly all-hands to kick off the week was removed. Our CEO couldn't make it. I thought that was odd, but I didn't think too much of it. Then right around noon we all had a meeting added to our calendars. A teammate of ours was very sick, so I, along with others were terrified the worst had happened. Thankfully, that was not the bad news we received but we learned the company was shutting down.
Where were you when you found out?
I was in Austin, Texas where I had just attended a networking event by Black Ambition. This was during SXSW.
Who was the first person you told after getting laid off?
My sister. I called her to spill the tea that my company was shutting down. It wasn't surprising, but it definitely happened more suddenly than I anticipated.
What was the first thing you did after receiving the news?
I was actually heading out to grab lunch when I saw the meeting suddenly added to my calendar. So, right after the announcement, I took the rest of the day off to decompress and talk to teammates, family, and a mentor about the company shutdown. I was going to enjoy my trip to Texas. It was a trip I wanted to take for years. I decided I was going to commit to my joy while I was out there, so I took long walks and enjoyed the sun. I could worry about everything else when I returned home.
When did you know you wanted to start your own business? How did the layoff bring clarity to that vision?
Starting my own business has been a dream of mine for a while now. When I was in my early 20s, I wanted to be like the self-made entrepreneurs you read about in Forbes. It was aspirational, sexy, and would make me feel that I made it. Now that I’m older and more mature, it’s about creating the work that fills my cup.
In recent years I’ve learned two lessons. The first lesson is that you can ask great questions of a potential employer, especially a startup, and still end up in a company that fails. The second lesson is great companies, great managers, great work, and great pay are a very hard combination to find. I could continue to search for happiness in another company, but you really don’t know what it’s about until you’re there. After the layoff, I figured I might as well try to choose my own adventure. So here I am. I love a stable job and check, but I also hate feeling empty.
The laid off to founder pipeline is something I'm seeing more and more of — why do you think that is?
I think this goes back to what I just mentioned. I think people are tired. They’re tired of feeling unacknowledged, disrespected, or unfulfilled. Working in the wrong environment(s), for too long, takes a toll on your soul. I’ve seen and heard of people who’ve gone through intense therapy after a bad job. There are so many broken social contracts. Growing up we were told, “Work really hard and you’ll make it.” That’s a lie. We were told, “Once you make 6 figures, you’re financially set.” A $100,000 salary isn’t enough anymore. In New York, you have to make $140,000 as a single person to live comfortably—but forget buying a house. So the lie detector determined that’s a big ass lie. Because the game and rules have changed so much, I think people distrust the traditional path—because it either hasn’t gotten them what they want or in some instances they’re worse off for it.
I think the last big reason we’re seeing more people go from laid off to founder is because we’re in a bad labor market, not because of innovation. Most people are not aspiring to build the next category disruptor. I suspect most are being propelled into entrepreneurship to survive. When someone else won’t give you a job, you still have to eat. So, you have to get creative.
When you knew you wanted to start your own coworking space, what was the first step you took toward making that a reality?
I took notice of all of the empty commercial space around me. I started to call up the listing agents and set up tours, before I got a broker. It didn’t require me to have money, it just required me to be curious. Touring a bunch of spaces taught me what type of space I don’t want and it taught me to never trust a landlord’s broker.
How did your past experiences working at The Wing and Round influence what do (and not do) building Openspace?
Working at The Wing showed me how purpose-driven companies can go left during hypergrowth, both in culture and scale. Round showed me what it looks like when a startup cannot find product market fit. In hindsight, I feel better positioned to build Openspace because I’ve seen what can happen at both extremes of venture-backed community businesses. Both experiences showed me how critical a community’s purpose and mission are: it’s the reason people show up (or don’t) and it’s the expectation that you’re held to. Getting those aspects right while also being true is crucial.
It’s also really important to me to build a company that myself and any future employee looks forward to coming to. I don’t want to build a company that someone has to recover from, and I don’t want to build a company that feels draining because it’s so stagnant — because that’s depressing, too. I know I’ll never be a perfect leader, but I do want to be a leader who cares about and considers my team. I appreciate all of my experiences, the good and the bad. I’m making lemonade with my own spin. Ya’ll will have to stick around to see what I’m mixing up in the kitchen.
What kind of community spaces exist for laid off folks and solopreneurs now? Do you hope Openspace will be somewhere they can gather?
Laid Off, of course! I’ve seen a lot of laid off folks join resume coaching communities, industry specific communities, and hiring platform communities, all supporting the job search. I feel the not-so-secret secret is that many communities don’t want too many unemployed people, unless it benefits their business model. They fear eroding the quality of their networks and profit. I want Openspace to be an accessible, enjoyable space filled with great people—not a super-elite status symbol.
A well-curated community can have someone well off and it can have someone who is not well off. You can lose your great title tomorrow, or you can get your breakthrough job tomorrow — that’s fluid and ever changing. A great community comes down to the people in it and what they’re all about at core. I thought about this issue a lot, so we’ll have a weekend membership for $35 a month where folks can come in every Saturday for community and lounging (no working). I want to do more, but that’s the first step I can take as a new business.
How did you decide on Brooklyn for Openspace? When do you plan to open to the public?
I was born and raised in Staten Island, but I’ve lived in Brooklyn for the last 5 years. I love Brooklyn, and I also feel it’s actually very underserved. We’re aiming to open later this year, so ya’ll can join the waitlist to know when we’re ready to open!
If you’re down with what I’m building, check us out at here. I’m always down to connect with amazing new people, so feel free to ping me on LinkedIn. Pray for your girl as I’m building Openspace! It’s taking a lot of courage and confrontation to put myself out there on a limb to build this thing. It’s a big risk and the hardest thing I’ve ever done.
This is so cool and I really love the addition of the "Social Club Saturday" membership. I would love to have this in Toronto!
It’s amazing to see all Michelene’s brilliance be highlighted! I met her more than a decade ago at a research fellowship and remember her having entrepreneurship as a primary goal. Rooting for her success with Openspace!