What Happens When A Founder Is Too Sick To Work?
I first noticed symptoms last summer. “Must be burnout,” I thought, blaming long hours as the co-founder and CEO of Stowaway Cosmetics. The D2C startup had been my singular focus, and I was loathe to notice any problems that could hinder my grind. After all, my tenacity is exactly what Silicon Valley celebrates, and it attracted investors like Gary Vaynerchuk and Jason Calacanis, the original heroes of the hustle porn category. Working myself to death was a virtue. I just didn’t think I was doing it literally.
It started slow, but grew into crippling chronic pain and swelling in my spine, chest, and left leg, as well as a set of symptoms I labeled “itchy and twitchy,” which I wrote off as “allergies.” That I took six benadryl a day and finished a 1000 pill bottle of Advil in three months should have been a sign. Every flare — combinations of swelling, hives, pain and insurmountable exhaustion — prompted questions from my teammates about whether I was “really” OK. They asked me to rest. To take care of myself. I didn’t listen for more than a day at a time.
Stowaway was at an inflection point and I didn’t want to take time for myself when the opportunity was so exciting. We were focused on building out not just a makeup brand, but the technical backend for a new kind of customer experience. I had slowed our burn so we could build our technical product right rather than chase revenue to impress investors. It was a long term approach that thrilled me after fixating on growth at any cost for the first years of Stowaway. I was confident we had the right solution for the long haul. But just months into the build I had to stop. I had become too sick to work.
What’s Going On?
I decided to take a few weeks off and go to some doctors. Of all possible people, my therapist was the one that recognized my symptoms. “Sounds rheumatic,” she said as I described the constant pain and pressure in my tendons and my joints. I laughed it off. Still I went to her specialist for a battery of tests.
An inflammation panel came back with results that were off the chart and clinical evaluations confirmed the blood work. Even the lightest touch was agony. I couldn’t put any pressure on my left side and was losing the ability to even walk. I was diagnosed with an overlapping set of diseases that were the result of uncontrolled swelling in my fascia, tendons, and ligaments as well as in my vertebra. “Enthesitis,” or inflammation where tendons or ligaments attach to bones, as well as ankylosing spondylitis were responsible. My entire body was locked in an autoimmune response it couldn’t stop, leaving me bed-ridden, exhausted and in constant pain. The doctor’s prognosis was that I’d likely spend the next year finding the appropriate treatments for results this acute.
Worse, if I didn’t seek treatment immediately, my condition could have permanent effects. Left untreated the swelling along my spine could leave me unable to walk. And the treatments were serious; I was put on a course of a chemo drug called methotrexate that made it a struggle to think along with high doses of steroids before we could even begin testing different injectables for a long term cure. My doctor advised me to quit work. Immediately.
What To Do?
In one of the hardest moments of my career, I had to let the board and our investors know I was no longer healthy enough to work. We had to find Stowaway’s next steps without me. I was devastated. I remember wanting to cry, but being unable to even get out a small sob because costochondritis had tightened the ligaments in my chest wall so much that my own rib cage felt like a tightened vice.
I tried instead to focus on what I could be grateful for: At least Stowaway was in good health. The company had no debt, plenty of product to sell, a loyal customer base, and an established brand. But given the vision in front of us and without a CEO to lead her forward, we needed to make some tough choices about her future. Did we hire someone to replace me? Sell to a cosmetics conglomerate? Find a private equity shop to grow it? What path would provide the best return for investors and employees?
I pushed myself to find Stowaway a home and make it happen. Even if I was ill.
The illness and treatments meant I could barely move or think, which made finding Stowaway’s next step agonizingly slow. If I thought running a startup was hard, nothing prepared me for how hard it was to find someone else to run it. Because I couldn’t just walk away.
Startups die every day, but if you ever want to start a company again, you have to come through as a founder. While our investors were very supportive of me getting healthy, they also came to me with dire warnings of what “everyone else” would think. More than one of my investors told me that if I didn’t sell the company, I’d “never raise venture capital again.”
The conventional wisdom was frustratingly contradictory. Apparently everyone knows that investors don’t care about any individual investment that much (most go to zero anyway), but they want to know that you’ll sacrifice yourself to protect their money in principle.
Finding Stowaway a Home
So off to pitch meetings I went, trudging around New York City, slowly pulling myself in and out of cabs with a cane. Air travel was out of the question as pressure changes were considered dangerous for my spine at the outset of my diagnosis. And if I wanted to walk I needed opioids and steroid injections, but with them I struggled to think clearly. There were no good choices.
Stowaway’s options, meanwhile, seemed just as complicated. Being early stage, we quickly found we didn’t have enough of a capital cushion to hire a replacement CEO. After all, I didn’t mind running lean, but cosmetic executives sure did. The conglomerates liked the brand, but without a founder in the deal it just wasn’t appealing. And as much as I would have loved to work for a big beauty house, I couldn’t give them a firm date on when I’d be healthy. Private equity shops similarly wanted the talent as much as the company. So no founder attached was a deal breaker for all the traditional sources — turns out there’s a reason founders get locked up for years after an acquisition.
While we had offers of help, in the end, the only people that could really sell Stowaway were me and the team. And we had a ticking clock. The longer Stowaway was in the wind, the less appealing it would be to acquire her. The team kept things going, but we weren’t making progress. There were days I prayed that we would just fail so I could focus on my health, but I knew that even just by being sick, I was at risk of being seen as a failure by people that had trusted me to return their investment.
I questioned my diagnosis. If I was a “do whatever it takes” founder, why didn’t I just take another painkiller and push through? And there were days that I tried, ingesting a small pharmacy hoping that the side effects of each pill would even each other out. I popped muscle relaxers and Ativan in an attempt to even out the jitteriness caused by the steroids. Then I’d take more steroids in an attempt to overcome the lethargy caused by the chemo drugs. I worried constantly about developing a drug dependency, measuring out my doses of painkillers with my iPhone alarm.
But then, after months of conversations asking hundreds of people if they knew of a good “home” for Stowaway, we met the folks at WIN Brands Group or WINBG. Their team was exactly what we were looking for: a group of operators with deep brand experience and financial acumen. They had the insight that the next phase of DTC would require some tricks from the past. They formed a holding and operating company that is rolling up DTC brands and running them with a common set of operational infrastructure in order to reduce overhead and take advantage of scale. They were a fellow startup taking the next logical step in the space. It was an ideal fit and thanks to their cross-brand operational model they didn’t need me to be part of the deal. They wanted what we had built.
They wanted to take the Stowaway brand and products and integrate it into their operation and invest in growing the brand for the long haul. And so in an ironic twist, a company founded to disrupt the traditional conglomerate model found her home in the modern version of a consumer packaged goods conglomerate.
But most importantly, the company we had spent years building didn’t go to zero. The investors have meaningful upside. I hadn’t failed them. And Stowaway is probably the best position yet to grow.
What’s Next for Us
And so we’re done. Sort of. As glad as I am that Stowaway has her home, I’ll never know the full cost of the last nine months. My progress in treatment has been slow, and I still have a long road ahead of me. Now that I’m free to focus purely on my care, I’m leaving to spend much of August in Michigan at a speciality inpatient clinic focused on autoimmune conditions like mine.
Perhaps the hardest part of all of this was silently suffering in isolation during so much of this process. After all, in an industry where we are always “crushing it,” there’s no room for a sick founder. For all of the kindness and sympathy I was shown by my own investors, the pressure of the “common knowledge” that I had to come through with an exit weighed on me heavily. It felt like a choice between risking my entire career or risking my long term health. I am still not sure if I made the right choice.
As I’ve finally been able to start giving signals publicly about what I’ve been living through, I’ve been stunned at the responses I’ve gotten — privately of course. Because I’m far from the only founder battling this. But like me, they can’t expose their companies to the risk of public perception of a founder who is anything less than 100%. And so they continue to slog away, in pain, until something gives, damaging their long term health in order to preserve our industry’s idea of “hustle” because “real founders” always find a way.
Ultimately, we’ll all have to face this as an industry. Do we really think that the healthiest companies are built by people who aren’t their healthiest selves? Stowaway wasn’t my first startup, and it won’t be my last. But I do know that anything else I do from here on out will have to be on terms that protect its founders and employees, not just for my sake, but for us all.
