Part 1 - The Million Dollar Opportunity

Chapter 2 - One Million Dollars to Turn This Around

After I resigned, I waited until the next morning to get my stuff from the office. This way I wouldn’t be embarrassed with colleagues staring at me as I packed my belongings. The pack up was very quick because as a senior leader, I actually didn’t have a desk.

In fact, most colleagues didn’t have a proper desk. We were all just sitting at any spot we could find in a tiny, crowded office. And we all had to bring our personal laptop to work.

Usually, that would be okay for a startup that is running lean. However, when I later found out how much we were spending on office furniture to create the startup vibe as well as all sorts of unnecessary items, like branded bags, a number of TVs, hiring branding agencies etc., I knew how much “people” meant to this company.

Ready for my next chapter, I got a call from James the next day.

I haven’t properly introduced him yet. James was the one on our weekly call getting updates from our CEO, Steven. James was the person who started this company, and he was the non-executive co-founder (meaning that he wasn’t part of the operating team), the largest shareholder, and the board chairman.

He had his own full-time job as a partner at a global engineering firm, and he was a big shot in his field - many people knew him. From what I understood, he always had a passion to build a software business, and so he kicked off this initiative and brought in two young co-founders to run and build the startup.

I met him once for coffee before I joined when he interviewed me. And since he was also on our weekly management call, I was surprised at his active involvement in the company.

He wanted to meet up to chat. I didn’t know what he was looking for, maybe he wanted to hear my honest opinion about the company, maybe he just wanted to stay in touch with me.

I didn’t care. For me, if I could be helpful in any way, I always loved to help.

So I went to meet him at a Starbucks near our office.

I couldn’t recall exactly what we talked about, but at some point, he started sharing with me that he actually knew the company was in a bad shape despite the hiring spree and the opening of a second city operation.

He was looking for a change in leadership, someone who could turn all this around.

He knew that the company was either a crash or a sense of hope. And he thought of me as someone who could bring in significant changes because I’ve helped my previous startup grow to multi-city operations as the COO.

I was flattered, but I couldn’t really comprehend what was going on all of a sudden. Something felt a little fishy.

He also proposed to have me and Steven as co-CEOs, this way we could complement each other’s strengths and weaknesses. And I immediately rejected this idea because I knew having co-CEOs would be the worst idea ever. And so we reverted back to the offer as a solo CEO.

Honestly, it was a little overwhelming, from joining to resigning, to now being offered a CEO role. He also told me I could be building my own company, including starting over, reorganizing the team, and most importantly, making it work with 1 million US dollars in the bank.

I needed some time to think about this, and I told him I’d get back to him.

I left Starbucks with mixed feelings. I was excited but I didn’t know what I was about to get myself into.

Going with My Heart

From the bottom of my heart, it was not an easy decision to make.

On one hand, the company was in such a mess and the offer seemed a little desperate. On the other hand, I’ve always planned to start my own company at some point, and having been the COO of a startup, it was time for me to step up to the next level.

I spent 2 days just sitting on the idea. In my mind, I was debating all the pros and cons of this opportunity.

And on day 3, I replied James.

“Thanks for offering me this opportunity, but I can’t take it. We’ve just met briefly, and I don’t think I’m ready for this.”

That was it. He was super respectful of my decisions and we said we would just keep in touch in the future. And I thought this marked the end of this “little adventure” of mine.

2nd Follow Up Wins

If you’ve been in a position that requires you to reach out to new contacts, you know that the first time you reach out to someone, they most likely ignore or reject you.

Then you go back for a 2nd time, and this time they’re more willing to listen to you.

Do you know why?

It’s really simple. When you do it for a 2nd time, they feel that you’re really making the effort, and you “deserve” at least one chance. This teaches us a lesson: hard work pays off.


2 days later, I got a text message from James again. He wanted to meet up for a drink just to chat about what I’ve planned next. He said he had another project that perhaps I could offer some help.

Based on our limited interactions, I already respected James a lot. He came across as a genuine person who wanted to form a partnership more than just hiring someone to work under him. He was reasonable and direct. He was understanding. And I had no doubt why he was so successful in his career.

This time we met up at the cafe in the hotel lobby, and the conversation quickly moved towards me leading the company again.

He expressed that he understood my decision, but he would really want me to give it a try because he believed in my character, my “careful mind” (because I rejected him), and that it would be a great opportunity for me to save the company since “it was already a mess”.

He asked me to seriously consider the offer again and he would provide his help as much as possible to ensure a smooth transition.

I rarely thought about the motives people had behind their words. With this offer coming for a 2nd time, I could feel James’ effort in making this right. This time it got me thinking more on whether I should take it.

I told James I would take a week to evaluate it again. At this point, I knew it was a 50/50 chance.

With such a big decision, I spent my entire week talking to a lot of people: my parents who were both in business, friends in large corporations, friends in startups, and we evaluated the pros and cons of this opportunity.

The list looked like this:


  • I would have a chance to discover myself as a first-time entrepreneur. I could find a new problem to solve, and there was already funding and talents so I didn’t have to start from scratch.
  • I would be paid an attractive monthly salary and equity options (15% with 4 years vesting) to be an entrepreneur - I believed it was an offer hard to beat.
  • I already have worked with the team for 6 weeks, and I knew there were some good talents.
  • I wanted to learn about building a software company, this was the perfect chance.
  • I was confident that I could improve the situation because it was at the rock bottom.


  • I didn’t have a problem I was dying to solve.
  • I had worked and grown a startup before, but it was in a different field. Most importantly, I only joined after they found product/market fit.
  • The company had a long list of angel investors who were brought in by James. The complicated shareholding structure might create problems down the road.

When I looked at the challenges presented ahead of me, I was definitely more inclined to test my own ability to turn this around than to worry about what the future might look like.

One phrase kept showing up in my head - “I have nothing to lose, right?”

As an operational person, I was very comfortable fixing the internal issues with my past experience. I knew that the immediate challenge would be to study the existing business model and see whether we could keep going with the same product.

But if not, what was our team going to create?

A Critical Decision Was Made

Despite all the unknowns, I decided to throw myself into a big pot of hot boiling water and see what happened next.

I took the offer, and became the new CEO of the company.

Honestly, the offer sounded too good to be true, and I was convinced that “I couldn’t do any worse”.

Of course, this wasn’t true. And let me explain why.

From investors’ perspectives, in the first few months, I was compared to the mess before, which made everything look great. They were excited and hopeful to hear that there was a new leader who had experience running a team.

However, after about 6 months, as the company went back on track operationally, no one cared about how it looked before. My performance was evaluated based on my ability to build a fast-growing company, so the statement that convinced me to take the offer “you couldn’t do any worse than this” was not valid at all.

I fell for it, but it was okay.

The challenge was accepted and I was ready to embrace it.

The only question left was how I was going to best use the one million dollars, the team, the existing customer base and all the other resources.

Key Lessons
  • Sales 101 teaches us to always follow up. This applies to everything you do that requires convincing another person. James respected my decision and genuinely followed up, and I was sold.
  • When you’re struggling to make a decision, always go for the one that you’ll regret the most if you don’t take it. We always regret things we don’t do more than things we do.
  • I was scared to take up this challenge, but I have always loved to throw myself into tough situations because I know that’s how I learn the greatest and fastest. And I take each day as it comes without over-worrying.

“You hadn’t had any founder experience and yet he was giving you a job? No wonder it failed.”

I was surprised as well, and that’s why I called this a once-in-a-lifetime opportunity that I couldn’t possibly turn down. I learned that he was keen to have me take over because 1) I had worked my way up in a startup previously, and I was slightly familiar with software products. Something that the last CEO didn’t have. 2) I knew that a big part of the offer was because I was there at the right time. It would be incredibly difficult to go out to find someone who would want to take this job, so I was the best option James had. Not something I was proud of, but whatever.

  • Career Advice For Millennials, You Need To Carry The Water - I’m a huge fan of Drift and their co-founder and CEO, David Cancel. Back in 2016, they released a podcast about carrying the water as juniors in a company. I’m a strong believer in this concept and have done so throughout my career, doing all the dirty and extra work as long as it gets the team and company going.
  • Respect: The Cornerstone of Success - Even though we don’t work closely anymore, I have huge respect for James. He is the best person I’ve met in business because of one thing: he respects everybody. He didn’t boss me around because I was younger and more junior. He said “sorry” and “thank you” appropriately when he was late to our meetings or when I helped him create a presentation deck. He was understanding and never put me in unnecessary stressful situations. No wonder he is so successful in his own life, that’s the biggest thing I learned from James.

Written with ❤️by Jessica Leo. All rights reserved.

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