Why We Are Investing in Real

Starting a company is like setting sail for an island that you are not sure exists. Sometimes you end up at that island. Sometimes you end up on a totally different continent. Sometimes you have to rebuild the boat while you are at sea, like the proverbial ship of Theseus. What matters most is that you set sail for a reason that endures, and that can sustain you on the turbulent seas.

Anu called me.

You have to meet Ariela. She’s building something that I think will resonate with you. It’s a mental health concept.

We met at the Marlton on 8th Street for breakfast.

I shared with Ariela stories of my own dark days, and told her about the book I was writing on my journey at the intersection of entrepreneurship and mental health.

She told me a bit of her story, a family member with mental illness, a father who taught her empathy. The arc from abandonment to acceptance was clearer from what I saw in her eyes than from anything she said. Peering in, I saw an old soul, a wisdom beyond her years. Clearest yet in Ariela’s life story was what had been forged in her upbringing: the resolve to build something that mattered, to create a company that could help people process pain, love, and life; to find something more of ourselves, and to be better with each other.

Though maybe fifteen years older, I felt younger than Ariela at times during our conversation. She scolded me for not remembering a mutual friend’s last name within moments of our conversation beginning. It’s a common experience with entrepreneurs: because they don’t defer to authority, they can feel like reciprocal mentors, even from day one.

They say that when the student is ready, the teacher shall appear. I’ve often wondered if it isn’t the other way around: when the teacher is ready, the student shall appear.

Which then begs the question: who is teaching who?

I could often tell which employees at Bonobos would later become entrepreneurs. They were not the only ones who didn’t care what I thought. There were many of those, and rightfully so. But they were the only ones who didn’t care what I thought, and who didn’t care if I knew that they didn’t care.

Ariela shared with me her vision for Real, a redesigned approach to therapy. The product idea was for a new kind of women’s mental health clinic, more of a studio or a sanctuary than a doctor’s office, with a digital backbone.

At the time it wasn’t totally clear to me what the digital backbone was. I didn’t spend much time asking her what it was going to be, for a reason that may sound strange:

I personally don’t worry too much about the idea for a product when I invest in a company’s very first round. I know that sounds weird, but before the much vaunted product/market fit comes something else I look for.

It’s harder to spot and it’s more important:

Entrepreneur/mission alignment.

If entrepreneur/mission fit is present, product/market fit will inevitably, after trials, tribulations, and iterations on those stormy seas, follow.

In getting to know Ariela, there were other hints of greatness. She’s biked across Switzerland, Italy, and the entire United States of America. She has a letter of recommendation from the founder of IDEO. She is formidable. She is humble. She is kind. She is tenacious.

I asked Manuela to meet her. She was equally impressed.

We invested.

Soon after, Ariela’s investor updates showed the most month-to-month momentum of any entrepreneur I’ve ever invested in. They’re also fun to read, with an economy of words that speaks to empathy for the overcrowded inbox, but with an abundance of that dancing emoji that looks like Jabba the Hutt on Red Bull.

Ariela was geared up for the April launch of her studio. It was ready, a year’s worth of tireless work, multiple years of dreaming.

Then COVID descended.

Disaster for a seed funded company with one chance to prove itself, let alone a 4-wall, brick and mortar concept, with cash running out the door.

Who could predict this would have happened?

Ariela got the team together, and within a week they built this.

And people reacted like this:

That’s the thing about great entrepreneurs.

They figure it out.

Spirit animal @bonobos, swan hunter @redswan, brother @monicaandandy. I love cilantro but love even more the people that hate it

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