My Learnings from Bootstrapping an IRL Dating Service in Man Francisco:
RIP Piña Colada!

Kati Schmidt
Dec 31, 2019 · 6 min read

After being an early employee at Airbnb and helping launch Airbnb Experiences, I left the company after 6.5 years to pursue my own venture. I realized online-dating was broken and am a true believer that the way to the heart is through the stomach. Piña Colada’s mission was to create meaningful connections between groups of six like-minded singles over great food.

Dating Industry Snapshot

  • Over 1,500 dating apps and services in the US (Marketdata Enterprises Inc.)
  • 150 men : 100 women: Ratio for employed, young singles in San Jose metro area (U.S. Census data, 2016)
  • 1/10 American adults spends > 1 hour/day on a dating app (Nielsen)
  • 48% of online daters are looking for ‘fun’ (B2B International & Kaspersky)

In this post, I am sharing my biggest learnings from this entrepreneurial adventure to encourage others to pursue their ideas while avoiding a few missteps I made.

Company Set Up Matters

It Really is HARD to Be a Solo Founder

While I had been warned by fellow entrepreneurs and investors, I decided to work on Piña Colada on my own after failing to find a co-founder through networking. I missed having a co-founder in two scenarios — and in between: When things didn’t go so well, being on your own can be quite depressing. There is no one to lift you up or share the burden. However, even when things went really well (first 100 users, Forbes feature), it was a lot harder to be proud of achievements and I hardly took the time to celebrate on my own.

Ask for Help Until They Say NO

The majority of my early users came through my own personal network. Once again I was impressed with the pay forward culture in Silicon Valley and the curiosity of fellow entrepreneurs to test new things. However, I had a hard time asking friends for support — even if they insisted. Looking back I realized that this attitude was limiting my success. After all, some of the most critical features of Piña Colada (the company’s name, the logo, referrals from friends) had been the result of brainstorming with friends and former colleagues.

Listen to your Users

The #1 thing I learned at Airbnb is to truly value your users and to engage them directly as often as possible to create a relevant product. While I decided not to play an active role during the first Piña Colada dinner at The Perennial, I was sitting at the bar incognito with a friend observing EVERYTHING that was going on: Did everyone arrive on time? How did they decide on the seating order? Did the restaurant staff pay sufficient attention to them? Did everyone enjoy themselves, talk equally and laugh? Did they leave the restaurant individually, in pairs or as a group? For future dinners, I asked all participants the same questions in a brief survey to continue to gather insights and course-correct when necessary.

I remembered that Airbnb’s co-founder Joe Gebbia told us that he was on the other end of Airbnb’s first customer service hotline in the beginning. So there was no question that I was doing the same. While I frequently referenced “us”, “we” and “the Piña Colada team” in emails, in reality, it was just me on the other end. Even though I used templates to answer repeat questions, I customized each message, read every single question, request, and suggestion carefully and was able to make some quick improvements like providing name cards so that dinner guests could remember each others’ names more easily.

As witnessed during critical times at Airbnb as well, responding to criticism fast and with a heartfelt apology helped me maintain trust in the fragile brand I was building. In one particular case, I decided to issue a partial refund as one participant’s expectations had not been met. While even with thoughtful matching, falling in love could not be guaranteed, I had to admit that there had been an unfortunate no show at one specific dinner that likely led to a less enjoyable dinner experience for her.

Growing a Business Takes Time

Piña Colada turned from a pilot group dinner date to 18 dinners hosted in 18 weeks. On week 19 I was very exhausted and hit pause while on vacation in Europe. I decided to take off the pressure upon my return and assess whether I truly enjoyed my work, the product, and the industry.

In hindsight and after comparing notes with other dating service founders, I realized that I had rushed things too much. While competitors with outside funding were able to grow their singles database for many months and at the same time focus on building a technical product, I hustled to match every single user upon sign up ignoring the basic marketplace truth that a critical mass leads to higher quality matches, higher user satisfaction and thus positive word-of-mouth.

In the end, I had to admit that I had over-indexed on making Piña Colada work at all cost. Although I had previously witnessed entrepreneurial burnout amongst friends, I did not establish a healthy work-life-balance myself, which led to sleepless nights over unsold seats at upcoming dinners and overall associating stress rather than pride with Piña Colada. While any business has stressful phases when working towards a big milestone, founders need to keep in mind that they are running a marathon and not a sprint and need to invest in their own wellbeing.

These Hacks might work for you, too:

Most growth experts will tell you that there are no shortcuts and magic tricks and that long term investments in SEO etc will lead to sustainable growth. While I generally agree with that, below are a few things that created some initial buzz and user growth.

  • Pitch journalists via HARO (Help a Reporter Out) to get media coverage. Not every pitch turned into something, but without HARO I wouldn’t have secured features in ABC, Cosmopolitan and Forbes.
  • Download all of your LinkedIn contacts and email them asking for their feedback and to spread the word. Include an email to forward in your outreach.
  • Sign up for Meetup.com, join relevant groups and share your signup link in the comments section, which triggers an email straight to every member’s inbox. Warning: You might get banned from the platform for spamming but it was worth it for me.
  • For dating services only: Create a profile on dating apps to engage with singles and encourage them to sign up.
I used this OkCupid profile to reach out to singles to fill the last spots of an upcoming Piña Colada dinner.

Resources for Female Founders & Leaders:

According to a 2019 report from Carta, women represent only 13% of startup founders and own just 7% of founder equity. Silicon Valley is slowly waking up to this imbalance and more resources are being provided to women entrepreneurs. Below are my favorite online & offline communities:

  • Elpha: Online forum for women in tech, which has spun off of YCombinator. My #1 go-to place when seeking feedback and recommendations.
  • Changemaker Chats: A salon series for women, hosted every other month. The Chats offer an intimate forum for sharing experiences and building relationships while learning practical tips to advance positive changes at work and at home. I co-lead the San Francisco chapter.
  • Phenomenal Woman Action Campaign: The weekly Bay Area events newsletter raises awareness about women’s rights across all cultures, socio-economic classes, gender identities, and abilities. I also love their merch.
  • Google Launchpad Female Founders: The Female Founders Summit features fireside chats and workshops and enables connections with fellow entrepreneurs. Afterwards, attendees stay in touch via an email list. In my view, this is most inspiring for very early-stage entrepreneurs and potentially a good place to find a co-founder.
  • The Assembly (Mission District) and The Wing (Financial District) are two beautiful female membership co-working spaces. It is refreshing to occasionally work surrounded by productive women in this male-dominated industry.
We hosted Alex Dimiziani, Co-Founder & Global Managing Partner at TwentyFirstCenturyBrand, for a Changemaker Chat in May 2019. Photo by twentytwentystudios.com.

Time to Say Goodbye

Piña Colada was a great experiment that impacted a few hundred singles in the San Francisco Bay Area for 1.5 years and taught me a lot about entrepreneurship and myself. However, I realized that I could not turn the concept into a financially interesting lifestyle business, the user feedback didn’t satisfy my mission to have a significant social impact and I didn’t see myself in the dating industry for many more years to come. So I decided to say thank you for the support and trust I experienced and joined a company with a compelling mission and great culture, which allows me to keep my entrepreneurial spirit.

With ❤, 🍍

Kati Schmidt

Written by

Director of Growth and Campus Operations CourseHero. Early X Airbnb employee. Home is San Francisco, California.

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