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This letter was originally emailed to the Wonolo team, I am republishing here in the spirit of transparency and the hope that some may find it helpful.


Dear Whamily,

It’s 3:38AM on Saturday, and I woke up with yet another nightmare and soaked pajamas drenched with cold sweat.  

Waking up with nightmares has been an ongoing event for me, since several months ago.  I understand the importance of a good night’s sleep, but that notion feels so foreign to me, especially right now.

Since devastatingly saying goodbyes to many of our amazing colleagues two weeks ago as a result of the economic shock due to the coronavirus pandemic, I have had numerous 1:1s and small group sessions with you.  During those conversations, there is a recurring question that I get asked. It manifests in different ways, but what I hear fundamentally is this: “What’s my job security at Wonolo?

It’s one of the most difficult questions for me to answer during these uncertain times.  The answer itself is not complex or difficult. In fact, the answer is simple, as you will see below.  However, the difficult part is how I answer it.

Whenever you ask me variations of that question, what I ultimately sense from you is the underlying “fear.”  The fear of not knowing what tomorrow is going to be like. The fear of losing what you currently have. The fear of not being valued for all of your hard work.

And may I be totally honest with you?  I have those fears, too.  

There have been numerous articles about how job security for CEOs is nonexistent.  In 2019, a record 1,600+ CEOs departed from major corporations. Not surprisingly, it’s expected that we will see substantially more CEO departures in 2020.  Among the startup class of 2014, when Wonolo started, very few companies have retained their original CEOs, even if those companies are some of the rare ones to make it this far.  

Personally, my job as the CEO of Wonolo is on the line everyday.  For every decision I make, I am judged, questioned, and tested. And please don’t get me wrong, I should be held to the highest standard. 

I get lots of feedback: good, bad, and ugly.  I am grateful for the encouraging and supporting words I get from you each day.  I would not be here today, still standing, without them. At the same time, I also receive constructive feedback that can be painful at times, and sometimes fills me with doubt.  “Yong lost touch with what’s really going on at the company. He operates like we are still a small team of 50.” I want to let you know that I take your feedback to heart. It’s one of the most valuable gifts.  I actively endeavor to make changes to address them.  

Truthfully, it’s not just your feedback that escalates my own insecurity.  I am required to demonstrate real results. I often joke that my happiness directly correlates with the company’s daily performance.  My wife comments that she finds me staring at the daily metrics dashboard all day. When I wake up and see our revenue numbers looking good, I let out a deep sigh of relief.  I’m visibly peppier. When they are trending in the wrong way, I find myself struggling throughout the day, not to fall into the quicksand. It’s unhealthy, I know. Pressure to perform as the CEO is immense.  

Nevertheless, losing my job as the CEO is not what I am really scared of.  What I am truly terrified of is not having Wonolo in this world. 

Wonolo not surviving would mean that I would no longer have a job to build this wonderful company with you.  More importantly, it would mean that you and I would no longer be able to serve amazing front-line workers and customers that rely on our service everyday.  That terrifies me.

And this existential fear has been with me since Day 1. 

It was gnawing in my stomach even during good times when we would win large deals, release amazing features, and delight our loyal base of users.  I would find myself asking, “what if the only reason why we made it this far was because we just got lucky, and all these amazing things vanish tomorrow?”  This fear would be even more amplified during difficult times like when we almost ran out of money multiple times, and when we had to say goodbye to our beloved colleagues virtually, not even in person, like two weeks ago.  

Having said all these, here is what I would love for you to know.  

This was the life decision I made – to leave my normal, stable career track to embark on building something everyone said was impossible.  They told me that it was “career suicide.” Moreover, I had to fully accept instability and insecurity in my life and also my family’s. Yet, I chose this path because I knew that I might have a direct impact on the outcome of my own career.  To me, being able to dictate my own destiny was the greatest security I could have for myself and my loved ones.   

I recognize that the same is true for many of you.  

Many of you are here because there is something about being able to make a direct impact on the success of a mission-driven startup.  Building a company with your own hands with talented people motivates you. Being an underdog, wanting to prove the naysayers wrong energizes you.  Walking on a tightrope as one team makes you feel alive.  

I have to believe that these aspects must have outweighed all the risks of being at a startup.  That’s why many of you are here just like why I am here.

So, here is my honest, direct answer to your question, “What’s my job security at Wonolo?”   Unfortunately, no one has it.  Not me. Not you. I am sorry to be direct, but that is the truth.  Yes, we have taken prudent actions to be financially robust, and yes, we’re staying strong – even amid COVID-19 – but no one has a handle on the full economic consequences of what we’re living through.  We are truly in uncharted territory.      

What we have here is greater than us.  We are here to serve millions of underserved people.  It may, at times, sound fluffy. It may also be difficult to see how we are making a real difference, especially during times like this.  Building a company is this hard.  The unprecedented crisis makes even the true believers question their own beliefs.          

However, even during these times of great uncertainty, this is what I commit to you.  

First, I commit to you that I will help turn our own fear into courage so that Wonolo has the greatest chance of success.   

I understand how important expressing our feeling of fear is.  We should always be honest about and respectful of our own feelings.  At the same time, please know that fear, when used positively, is one of the most powerful motivators to bring out the best in us.  When we share our own fear openly and embrace our vulnerability, it unites us. It becomes a multiplier of strength. We should acknowledge it, and leverage it as our own galvanizer.    

When I reflect on all the major successes over the last 5 years at Wonolo, we achieved them together during extreme times of uncertainty and challenge.  I believe that it’s because we were able to turn our own fear into courage to step up and lead this company together. This time is no different. We are in this together.  

I commit to you that I will continue to steer our fear into courage.      

Second, I commit to making Wonolo a safe place for you.  

I want to promise you that Wonolo will be a place where you are heard and seen fully.

Your free voice at the company is welcomed and admired.  Your colleagues respect your different point of view. You feel like you don’t have to hold back on things that will help Wonolo win.  You are admired for being your true self. And we all stay true to the Tao of Wonolo even when no one is looking.

I commit to you that I will tirelessly work to cultivate a safe place for you even when I have to make painful decisions for the greater purpose of the company.

Finally, I commit to fighting my hardest. 

I am a human.  I am imperfect.  I confess that I don’t know what to do 99% of the time.  There is no textbook or blog on “How to build Wonolo 101.”  Although I am surrounded by millions of opinions and advice from people who are smarter than me, I don’t know who is right and what the right answer is.  

Yet, even during these difficult times, I commit to you that I will still fight this battle with you.  I will put myself out there with conviction and confidence as your CEO. I will overcome my own imposter syndrome.  I will fight through these challenging times. You have my commitment.

So, my beloved Whamily…,

I understand that these are very difficult times for all of us.  What we currently face will, if not already, test who we are everyday.  However, don’t fear what we cannot control.  This is the moment that will bring out the greatest in us.  It will transform us in a way that we would have never imagined possible before.  

An American author, Carlos Castaneda, famously said, “we either make ourselves miserable or we make ourselves strong. The amount of work is the same.”  We can dwell on our own fear of uncertainty and instability. Or we can focus on emerging even stronger as one team. We can have the greatest influence on what our future is going to be like.  

Specifically, during these challenging times, we will obsess over the following three things: who we serve, how we manage time, and where we focus. 

  • Who we serve:  Front-line workers and customers need Wonolo more than ever.  There are now more unemployed/underemployed workers who need us direly.  Our customers need us to help them manage ups and downs of their mission-critical operations.  Both sides need to know that we are open for business and here for them. We will continue playing a critical role in helping both of them navigate through multiple challenges related to their jobs. 
  • How we manage time:  Our concept of time has fundamentally changed.  Things are developing and changing in real time.  We have to stay nimble and move with urgency. We can no longer plan for quarter by quarter.  Instead, we should stay flexible and be OK with changing directions week by week. Our ability to move fast will help us overcome external challenges.
  • Where we focus:  There are a lot of directions we can pursue right now, and it’s easy to be distracted and lose the sense of priority.  Please let’s make sure that we have clarity on what we must do as a company, and more importantly, what we must not do.  We will make fewer bets, but fully align around them, and execute them flawlessly.      

When we come out of this, we will stand here, looking back at what we accomplished together.  There will be millions more jobs for underserved workers. Thousands of our customers will flourish once again.  And we will be right there with them, celebrating their success.  

The greatest superpower we all have is our courage.  And the world needs it right now.  So, let’s use it.

I am truly grateful to you for still being here with me, and for allowing me to lead you even after all the mistakes I have made.

Let me see if I can fall back asleep for a few hours before my daughters get up.

Thank you,

Yong