I was going to get fired.
My first job out of school was at an education technology company as a Sales & Support Associate. On my second week, I “trained” 60 teachers through an online webinar on how to use our web product. This was done by reading off a four-page script intended for sales pitches.
After the training session, the director of the school emailed my boss. The email read, “The training was useless… I demand another session… the trainer was a waste of time… teachers are more confused than ever… low confidence in the software.” Each sentence made my heart sink further. I called my mom after work that night, freaking out that I was going to get fired.
I upped my game for the remainder of the week, studying as much as possible and leaving the office as late as 11pm each night. I manned the support desk alone by relying on past customer support responses. On the fourth week, my boss informed me that she had been silently reading my ticket replies and observed fantastic improvement in my knowledge of the platform. I’ll never forget that feeling of relief and redemption.
Where did I go from there?
I’ve since then worked closely with four CEOs; interacted with attorneys, tax professionals, and international businesspersons; and collaborated with ultra high net worth individuals with 8, 9, 10-digit bank accounts. In contrast, I’ve also witnessed homeless children under freeways in Mumbai; captivated middle school children in Galle, Sri Lanka; and fended off solicitors knocking on my taxi windows in Jakarta. These experiences span 225,635 miles flown across 141 flights and 15 countries.
A younger me would not have fathomed this as my career trajectory. My dad is a mailman and my mom works two part time jobs as a high school food server and as a supermarket chain bookkeeper. Yet, through hard work and an equal amount of luck, I’ve kept up in the realm of business & technology.
My essays in recent years have focused on traveling through business-related trips. Due to the nature of working in proprietary software, I wrote about things I did or people I met outside of work. The products I’ve worked on have since shipped, so I can finally share the more memorable experiences and my takeaways.
I stand on the shoulders of giants. These giants include working with these CEOs who have conquered entire industries and disrupted markets. However, these giants also include memories derived from my travels that have broadened my horizons. The culmination of these people, travels, and memories have played a part in shaping the entrepreneurial drive I have today.
But why write this?
The more I learn how money makes the world go ’round, the more I’m drawn to entrepreneurship. I enjoy working with all departments within a company. I enjoy interacting with people from around the world. I like solving tough operational, organizational, and technical problems, and creating things that are valuable to others. Product management and consulting have been immensely gratifying for those very reasons.
So the purpose of this essay is twofold: (1) reflect upon my work experience to help improve my odds of succeeding as a lifelong entrepreneur, and (2) to share these stories for anyone to read and learn from.
Story: what’s it like eating lunch with several CEOs?
One CEO I worked with ran an international manufacturing & wholesale company. My job was to form a software division to build a mobile app that would provide a new sales channel. I met with him in China to (i) review the business plan, (ii) learn about the factory and prototyping/design center, and (iii) draft a proposed software team organization chart. The milestone of the trip was to write job descriptions for each member’s role. The company would then send these resumes to recruiters.
In the middle of the trip, the CEO informed me one morning that we were to have lunch with some of his friends. Come lunch time, we drove to a Taiwanese restaurant and were escorted into a large private room on the upper floor. There were around 10 people at the table. I was introduced to three other CEOs.
Lunch comprised of a set menu of various seafood, soups, vegetable dishes, fried dumplings, and more. There were two servers who were completely dedicated to us. They were either wallflowers or stood outside of the door waiting to be summoned.
I took photos as fast as I could, self-conscious that I’d be judged for doing millennial shit.
The conversations between these men were fascinating.
CEO #1: “Hey CEO #2, how’s business? I notice your stock price has tripled since the IPO last year, great job!”
CEO #2: “You know I can’t discuss investments. We’re a publicly traded company now, I can’t give insider information.”
*Some laughter*
CEO #2: “…But I would avoid investing in my own company right now. The stock is priced too high, and I don’t know why. I think some banks or hedge funds are mingling with our company.”
Here I was, a 20-something year old dude sitting next to made men in their 50s and 60s, out of my comfort zone and trying to figure out what to say without sounding moronic. Until that very moment, my worldview was that CEOs were the “top dogs” in the business world. I would not have thought that they would be troubled by market manipulation by other entities, especially regarding their own company.
During this experience, I was able to sit with executives of publicly-traded company and learn that they too are privy to the whims of even more powerful individuals or entities. This experience gave me a rude awakening on the realities of the business world and its hierarchies. From their dialogue, I gathered these were old friends engaging in friendly competition by poking fun at the state of their companies.
Through the course of this project, I had the pleasure of engaging with CEO #3 a few more times, including visiting his private ranch/haven. And although I don’t drink alcohol, I could not turn down a glass of wine from him. “[CEO #3] refuses to drink anything less than $1,000 USD.”
…but that’s a story for next time!
Upcoming Stories
After a long hiatus, I plan to begin writing again with an emphasis on business. Essays will be written in a format similar to this essay: Four lessons learned from negotiating for a $10,000 bonus.
- Having dinner with a businessman at his private ranch/haven
- Demo’ing to investors in Hong Kong
- Having breakfast with two CEOs at the Four Seasons Bosphorus in Istanbul
- Working with two Chinese management consultants with an English interpreter
- Interacting with investors in a pitch in Taipei
- Pitching an investor in Silicon Valley
- How a job interview became a conversation about how to get an Indian visa with a CEO
- Flying from California to China over the weekend to work two days
- Taking a dozen American coworkers to have spicy Chongqing hotpot
- Driving a CEO to LAX from San Diego at 11:30pm, for a 1:15am flight
- The origins of my tea drinking hobby: learning the Chinese tea ceremony through a CEO
- The first time I laid off an employee
- What kind of leader I want to be: lessons learned from being pampered by a businessman
- How I spent my weekend earning extra money during a business trip
- Different giants: how I learned personal finance through my parents
- Books that have supplemented my management methodology
- Personal weaknesses and what I need to do to address them
- …and more.
Andy Cheng 
