“Pivot” isn’t the bad word some people make it out to be. Many of the greatest companies in YC’s history pivoted along the way.

One example: Clipboard Health. Today Clipboard is built around the idea of connecting independent healthcare professionals — think nurses, medical assistants, or phlebotomists — with healthcare facilities to let them pick up shifts that work with their schedule. It means more flexibility for the nurses, and more much-needed help for the facilities. As of its last round, it's valued at over $1.3 billion.

But that idea wasn’t the first idea. Or the second. Or the third. Clipboard Health founder and CEO Wei Deng tells me the company went through “six to eight different pivots” before it evolved into what it’s known for today.

I recently talked to Wei to hear more about Clipboard’s origin story, and our conversation was absolutely full of insights. Here’s just some of what she shared with me.

Talk to people, find the real problem

Wei started out with a mission, and it’s one that hasn’t changed: to find ways to lift people up the socioeconomic ladder.

The initial idea was to offer an alternative to student loans — an income-share agreement, years before the idea would become popular.  They tried offering it to software engineers, but didn’t get many bites. They shifted to working with lawyers, then doctors — same deal.

Another group they tried working with was nursing students. It was in the conversations with these soon-to-be nurses that Wei noticed a common thread: they were all very worried about actually being able to get a job after school.

“The idea morphed into… okay, let me try to help nurses find jobs.” Wei tells me. “Helping them with their resumes, helping them with interviews, finding ways to give them clinical experience… It was hard, but it was the first pivot that was at least into this industry.”

Wei and her team eventually decided to build a job board just for nurses — and it was there she discovered a deep-rooted problem she could solve.

“The only people who would post were staffing agencies,” she says. “I would give them candidates, the staffing agency would hire them full time… but then every month, they’d give the nurse a different schedule. They’d say ‘Here’s the schedule for February, here’s [a completely different] schedule for March.’ It was incredibly hard to find full-time people who could commit to this ever-changing monthly schedule.”

But what if she could flip the formula around? What if instead of facilities assigning nurses an unpredictable schedule, nurses could sign up for the shifts that work for them?

“At some point I just called the facilities myself and asked: ‘Do you need the same person coming in every month? Or can I give you two different people to fill up that schedule?’ And they all said ‘Yes, we’re very short staffed, we just really need people.’ And this was before COVID, this is 2018!”

She tried building software for the staffing agencies to do this — they shrugged it off in favor of paper and pen. The existing system worked for the agencies, but she knew it wasn’t working for everyone else involved.

“At that point I was like, OK, there’s an opportunity here.”

Find the right person

Wei started reaching out to more facilities directly… but it’s not every day someone calls the front desk of a healthcare facility with a product pitch. The person on the other end generally didn’t know where to send her next.

“I made hundreds of cold calls a day to try to get someone to even meet me in person […] but I would just get hung up on,” she says. “Everybody thought I was looking for a job. I couldn’t reach the decision makers, so I decided to just go and meet people in person.”

Seven months pregnant at the time, Wei was Ubering from facility to facility to pitch the concept of Clipboard Health. After a month of this, a key puzzle piece fell into place; at a facility in Walnut Creek, she found the exact right person to talk to.

“This woman… I think she felt sorry for me because I was super pregnant,” Wei notes. “She taught me a lot of the jargon; she was a scheduler and I was, basically, an agency. She decided to give me a chance — she was like: if you can get two people to fill these two shifts this weekend, I’ll hire you on a permanent basis.”

“We filled those shifts,” she says with a smile.

That facility signed on to be Clipboard’s first customer; today, they work with around 5,000 facilities.

The benefits of being new

While coming in from outside the health industry meant there was a bit of a learning curve, Wei now sees it as a hugely positive thing.

“I’m very happy I didn’t have experience in healthcare… because I would have thought this was really too hard,” she says. “Sometimes experience scares you off. You've seen how others failed and you’re like 'Oh, we can’t do it.'. We would have had preconceived notions of how facilities work and what they care about.”

“For us it was bad and good: we didn’t have the relationships, but we were able to think about a lot of things from first principles. That was kind of freeing.”

If you don’t win, you learn

Throughout my conversation with Wei, I notice a common theme: she is incredibly persistent. There were the aforementioned countless cold calls with facilities. Before that, there were dozens of rejections from VCs. Years before that, when studying to become an investment banker, she emailed thousands of bankers just to ultimately get career advice from a fraction of them. Even as a teen that just wanted to teach herself chemistry, Wei was cold calling universities to try to get them to let her use a lab. Most, understandably, said no.

I asked her what keeps her motivated when met with rejection:

“It’s something I tell my son, and I truly believe: the people who win the most also get rejected the most. When I was pitching investors, I think I got told ‘no’ sixty times. And I’m not a robot — I was crushed.”

So she turned collecting rejections into a game.

“If you get fifty ‘no’s, you’re not in a worse place than you are after just one. By collecting the ‘no’s, I’m just getting better at the thing!”

“Something happens when you have that much practice,” she adds. “You can’t help but just get better. I truly believe that. I definitely felt crushed many times; people would say all sorts of mean things. But I would just regroup and think: one step closer to getting better.”

When it’s working

I asked Wei how, after a half-dozen-plus pivots, she knew this was the right idea to charge forward with.

“I noticed a difference in how our customers engaged with us. Customers wanted to talk to us; they wanted to give us suggestions. They had emotions around our product. They were angry about stuff; they were elated about stuff. “

“Yes, from the qualitative data we were growing much faster” she notes “but you could also just feel the difference. You know when you have a date with someone and it’s kind of lukewarm, versus a date with someone who’s super exciting and you’re both interested? It was like that. I wasn’t sure it was working, but our customers cared a lot more.”

What’s next

Even after growing Clipboard into what it is today, Wei isn’t looking to stand still for long.

She wants Clipboard to expand into other health care verticals that are natural fits — she mentions dental and anesthesiology as categories the company is exploring. But she’s also building what she sees as the “anti-Clipboard” — the thing that would ultimately replace some of the demand for Clipboard Health. Because if they don’t build it, someone else might.

“I will never be one to say ‘We’re crushing it! We have product market fit! You have to be honest with yourself; markets change quickly.”