Keep Embracing the Adventure – Learnings from Building and Folding Your Own Company in Silicon Valley: An Interview with Kati Schmidt

Kati Schmidt on a sunny terrace in a white Piña Colada t-shirt

German Accelerator mentor Kati Schmidt (Photo by Bob Cut Mag)

Being a founder can be lonely, but it doesn’t have to be that way. Kati Schmidt, Director of Growth at Course Hero, Entrepreneur, and German Accelerator mentor, is a Münster native but has been living in Silicon Valley for quite some time. Having founded and folded her own venture, Piña Colada, she shared with German Accelerator why persistence is essential, what we can learn from failure, and what it takes to be a successful woman in business.

Kati, you’ve been living and working in Silicon Valley for a few years now. What brought you to the West Coast?

It’s a bit of a crazy story: I came here five years ago after I won the green card visa lottery. I tried eight times in a row (that’s eight years!), so it certainly wasn’t first-time luck. When I got the notification that I won the green card, I packed my bags and moved to the States. I always wanted to come to the U.S., in particular to Silicon Valley. I just love the entrepreneurial spirit here!

I was an early Airbnb employee and worked there for more than six years – I worked in four offices in four different roles, starting in Berlin, Germany, and finishing off my journey with the company in San Francisco. My greatest achievement was to help launch the new business unit: Airbnb Experiences.

In 2018, you launched your own company, called Piña Colada. Can you tell us a little about this exciting journey?

I always wanted to start my own company, and I wanted to do it before having kids or a mortgage. So I came up with the idea for a group dinner dating service called Piña Colada.

I realized that online dating in San Francisco was complicated. The market was fragmented, and to be honest, a lot of dating apps don’t want you to be successful, because, in the end, they want to keep you as a user. I could certainly not guarantee that my system worked better. Still, at least my goal was to create purposeful experiences for people who were looking for serious relationships and not just for a casual date.

Initially, I tried hard to find a co-founder, but I soon realized that in Silicon Valley, everyone has their own ideas. I met with so many potential co-founders, and they all pitched me their ideas, but none aligned with what I had envisioned. I finally decided to do one dinner pilot on my own and realized I have enough users to do another one. I saw that there was demand and my business kept growing. I did everything myself, which was quite lonely to be honest, especially when things worked out well. I was featured in Forbes and Cosmopolitan but had no one to celebrate with. Initially, I wanted to celebrate reaching my first 100 users and when I looked at the spreadsheet I realized there were already more users than I thought. That’s how fast the business was growing…and how much I was absorbed in it.

Everything seemed to be going well, but after one and a half years, you choose to close the Piña Colada chapter? What made you decide to wrap up your own venture?

After almost two years of matchmaking, I decided to stop hosting our Piña Colada group dinner dates. While I was able to create several unique matches, I realized that I could not turn the concept into a financially interesting lifestyle business. In the end, I had to admit to myself that (A) I was trying to make this entrepreneurial experience work at all costs and (B) the user feedback didn’t satisfy my mission to create meaningful connections. Nonetheless, I’ve learned a lot about myself and entrepreneurship, and I’m thankful for that roller coaster of an experience.

What were the biggest lessons learned while building your own company?

Even though I had to say, “RIP Piña Colada,” I want to encourage others to pursue their ideas. Founding my own company had me realize that it doesn’t have to be a perfect, polished product. At Airbnb Experiences, we were operating with Google spreadsheets for a very long time. It was the same for Piña Colada. It’s a lot of manual work in the beginning, but your users don’t have to know that necessarily.

Summary visual of Kati's '5 Lessons Learned From Building Your Own Company'

It is not easy to be a solo-entrepreneur. I had to learn and revisit my strengths and weaknesses, and I had to overcome my aversion to specific tasks because there was no one else I could delegate tasks to. It was like getting thrown into the cold water, but without it, I would have never known that I like sales and that I am actually quite good at it.

You are a mentor at German Accelerator working with many startups. Is there a common pattern that you find when working with German startups, and what advice would you give to overcome the typical challenges and make their U.S. expansion most successful?

The entrepreneurs that come over to participate in the German Accelerator program already have a very successful business in Germany. Some might have even successfully expanded in Europe. They have enough runway and resources to expand. Now, there might be a danger in just that as they might think that they already know how it works. So while they might have been able to prove their business in Germany, it doesn’t mean it will work the same way here. You should be very, very open to questioning everything. Prepare yourself to start all over. The more you are open and willing to try new experiences or ideas, the sooner you will succeed in this market.

Another recommendation I have is to ask your network for help! Especially here in Silicon Valley, there is a great support system for entrepreneurs: free conferences and workshops, serial entrepreneurs, and investors, who are looking for the next thing, wanting to give back as mentors, and free trials of products that can help boost your company. You have to be a bit bold, just ask!

Summary visual of Kati Schmidt's '5 Tips to Tackle Your Entrepreneurial Journey''

You’ve founded yourself and are now also empowering other women to found companies. Can you tell us more about why it’s important for you to support other women in business?

Silicon Valley is still very male-dominated. At Airbnb, we were fortunate to have a women’s group to help find role models, to get together, and to create a safe space. It’s amazing how open you can be, and then you realize that many other women struggle with the same issues and support each other. But there aren’t that many female role models in leadership positions. At Airbnb, the number two in the company was a woman, but the majority of the leadership team members are male. If you move up the ladder, there might only be one other woman at the top, but what if you can’t identify with that woman? If there isn’t a female leader you can look up to at your company, look beyond your company: Silicon Valley has many organizations and events that support women. You just have to keep your eyes open!

Women often worry about the challenge of having a family and a career, and they think it’s either one or the other. Sometimes, women already slow down their careers before they even get pregnant. They don’t apply for promotions or switch jobs, because they’ve already started putting their career on the backburner. I want to help change that.

I volunteer as a director at Changemaker Chats, which is a salon series for young, professional women. Every other month, we create a safe space, invite a high-level female speaker, and have candid interviews and conversations. The speakers share the challenges they went through, from salary gaps and trying to break through the glass ceilings to sexism and sexual harassment and how they handled those situations. All the women in the audience can ask for advice or support, and we deliberately try to create an environment that is both safe and supportive.

Kati Schmidt interviewing Alexandra Dimiziani at a Changemaker Chats event

German Accelerator mentor Kati Schmidt at Changemaker Chats

You talked about role models, who are your role models, and why?

One of my mentors is Elizabeth Bohannon, who now also works as a professional coach. She has had an inspiring career at companies like Intuit, Williams Sonoma, and Airbnb, and was able to prioritize her family at times as well. Every time I interact with her, she empowers me and gives me a lot of energy.

Where do you go when you need inspiration or help?

I’m a social butterfly, so I usually just go to other people. I either attend an event, speak to my friends or people I briefly know or have met. Before hosting my first dinner at Piña Colada, I told everyone about it and got great advice and connections from all sorts of people. I think that’s a huge difference between Silicon Valley and Germany. When I quit my job at Airbnb, my American friends were very supportive and excited for me. They all wanted to help me find a new job. My German friends, on the other hand, were worried that I would need to move back to Germany. This reaction isn’t uncommon in Germany. Most Germans tend to have this very conservative and risk-averse mindset. They ask, if you have a secure job, why would you step out and make things harder for yourself? In the U.S., you get a boost of support! Even if it doesn’t work, it’s not a big deal. Instead, people applaud you for trying.

What is your philosophy of life?

At Airbnb, one of the core values was to ‘embrace the adventure,’ which really speaks to me. I think it’s really about pursuing your dreams and trying new things. I did this with the green card lottery, and remember, I tried that eight times! It’s about being persistent and not giving up. Had none of those attempts worked out, I would have done something great and fun in Europe. I think it’s this balance of not giving up, but also having a plan b and c.

About Kati Schmidt:

Kati Schmidt is the Director of Growth and Campus Operations at Course Hero. After winning her green card in the Diversity Visa Lottery, the Münter-native relocated from Berlin to San Francisco in January 2015. As an early employee of Airbnb, Kati worked on launching and scaling their operations in Europe, starting their public policy efforts globally and launching Airbnb Experiences. Kati founded her own venture, Piña Cola, but after two years of hosting dinner parties, she wrapped up the company at the end of 2019. In ‘My Learnings from Bootstrapping an IRL Dating Service in Man Francisco: RIP Piña Colada!’ she shared her experience of wrapping up her own venture. Kati is a mentor at German Accelerator, supporting German companies to expand their business to the U.S. Read her blog ‘Kalifornia Kati’ here.