Three Entrepreneurial Lessons I Learned

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On November 16, 2017, I was in a Karaoke bar with my SSF peers in the city of San Francisco. I was drinking and singing along, waving and swaying to the music, waiting for my turn to sing my song “Lucky” from Jason Mraz.

My phone ringed. It was a message from a friend in the Bay Area, J. I got to know J during my time in SSF. In SSF, I finally started getting my hands dirty working on my dream – to design a school. I officially kicked off my journey of school design when I started my second master degree at Penn GSE – Education Entrepreneurship. Lots of meaningful conversations at Wharton helped me narrow down my professional options to education – specifically, non-instructional leadership in innovative schools. As soon as I arrived in California, I started to drive the project forward. I reached out to mentors and friends in the education space, found opportunities to plug myself into education circles at Haas and Stanford GSE, flew around the country to visit a variety of innovative schools and their founders, and gathered groups of parents with different backgrounds to understand the market. One piece after another, the vision of the new school was gradually crystalized.

J was a friend I encountered during my desperate exploration of the education ecosystem in the Bay Area. She has been very active as an experienced education advocate in Palo Alto in the past few years. I shared my stories and my vision with her over coffee at the beginning of SSF and we kept in touch ever since. On this most random night in SF, she texted me.

“Hey Cindy, have you heard that AltSchool is closing down a campus in Palo Alto? My daughter goes to that school. I am leading an effort to create another independent innovative school to keep the educators from it. This is a great opportunity to accelerate your school design timeline. Are you interested? I can call you in 10 minutes.”

I was freezed. It felt like getting hit by your dream, a dream that took many years to discover. I literally blanked out in the middle of people’s wild singing.

Lesson One: “If you know it’s a rocket, get on it first without asking questions.”

We had a great conversation and some initial brainstorming over the call. I was quickly weighing this opportunity in my head. Yes, this kind of opportunities wouldn’t happen everyday, but it did change my original plan and expected setup. I also knew that this project had a built-in countdown – since we were to “save” a school, we had to figure everything out within less than half year before all educators and families left for other schools. Any decisions had to be made fast and accurate.

“J, if we decide to do this, you’ll have two words from me: all in.”

Today when I recalled that phone call and the way I said “all in”, my heart still beats fast. Sometimes it makes sense to spend some time to make important decisions in life, such as choosing a husband. But sometimes, when you take too long to evaluate pros and cons, an opportunity may have slipped away. Buying a house in the Bay Area is one example, and jumping into this school project is another.

Ever since that phone call, tasks to be done and problems to be solved exploded. Thankfully, Bain trained me to become a very fast doer, and J was extremely efficient and responsive on her end too. Things were moving forward very fast. We quickly created multiple versions of financial projections and initiated several rounds of negotiations with AltSchool regarding the support our new school could receive from it. We identified a funding gap of 1 million US Dollars to support the first 3-5 years of operation before the new school becomes self-sustainable. We immediately got on the fundraising task, the first go-or-no-go milestone we needed to hit.

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Lesson Two: “What do you want? What is your bottom line? What can you give in?”

In the process of fundraising, another interesting thing was that people kept asking us, over and over again, these three questions. No matter how well you prepared your answer, when you were on the negotiation table, it was simply hard to stick with it.

It’s especially hard when your bottom line became the only hurdle between you and your goal – extra hard when your goal was a one million dollars check. One time we were having a very positive conversation with one large donor who requested more board seats than we expected. Although nonprofit organizations like ours do not return to investors, board seats largely determine the independence of the school. In return, the donor promised a large amount of donation to support not only our school operations but also future property development. It was a large check that nobody wanted to turn away. However, we knew that independence of the school was an agreed bottom line among founding team members. After rounds and rounds of discussion, we decided painfully that we should not largely compromise board independence for donations. In fact, turning away donations with less ideal terms welcomed donors with better vision alignment. It was a painful no to say, but we never regretted.

Lesson Three: “Patience is a self-cultivation for entrepreneurs.”

In the process of working with investors and donors, things were drastically slowed down. A lot of times we had to wait for investors and donors to get back – one million dollars is not a small amount to anyone. On top of that, our team worked remotely and communication was not always timely. Waiting was a big theme for the past few months.

I’m sure “waiting” is nothing new to any entrepreneurs. However, it’s the first time I dealt with anxiety – I, of course, had anxious experiences before, but this time the anxiety was so strong that it got very physical. So strong that I had to name it. So strong that kept me from doing anything else, including sleeping. I never knew that I could lose this much of my composure.

It was an introspective moment too. In the nights when I couldn’t fall asleep, my brain was dominated by two threads of conversation. On the one hand, I couldn’t stop but continued to strategize every detail of the project, thinking through every power dynamic and deal structure that may impact our overall strategy and immediate next steps. On the other hand, I kept asking myself how I could “want it less”. It’s a weird question to ask as an entrepreneur, but yes, I wanted it too much and got too emotionally attached to stay balanced and remain rational. A desire to make it work may be a strong driver to progress in the startup stage, but it can also be a great obstacle founders have to overcome to make objective decisions and stay resilient. I took this as a great mental exercise to stretch my stress tolerance and stability.

Patience makes an entrepreneur more mature. When you are able to wait for outcomes to reveal, you are more ready to receive success or digest failure.


Our school project is moving forward steadily. Although we still have a few go-or-no-go milestones to hit, we saw positive signs to launch in this upcoming fall. I am sure I have just taken one baby step towards a big mission, and there is a long way to go. I will continue to reflect and summarize, walking towards my dream with passion and determination.

And maybe sing “Lucky” more often?


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