Part 1 - The Million Dollar Opportunity

Chapter 1 - Joining a Promising Startup

To kick off this dramatic roller coaster startup ride of mine, I should first tell you about myself.

My name is Jessica and I grew up in Luxembourg. Many of you might not have heard of this place. It is a small European country surrounded by Belgium, France and Germany.

I spent most of my childhood here before I spent a total of 8 years in a boarding school and a prestigious college in the U.S. I was 13 years old when I left home.

Banking and finance is huge in my country, so I always thought I would study hard and become a banker one day, just like my parents. I didn’t end up doing finance, but I did major in business in university.

Personality wise, I’m quite an introvert. I enjoy spending a lot of “me time” with the Internet and books. But to my surprise, a lot of people think I’m extroverted and outgoing. My own explanation is that when I need to, I can throw myself out there to interact with people, that’s what is required in the “real world”.

I’m obsessed with personal growth - anything that can make me a better person. Reading, challenging myself with new sports, setting measurable new goals ... that’s what I enjoy.

Enough of my intro. I am not here to write my biography, I’m not that old. This eBook is about my 18 months running a startup and what I experienced, so let’s speed up a little.

Prior to these 18 months, I had 2 career experiences for a total of 6 years. After graduation, I moved back home to Luxembourg and got a job as an Assistant Product Manager at a development agency where I worked for 2 years, and then I joined a fast-growing retail startup expanding and operating their brick-and-mortar store programs.

I was first hired to be in the expansion team, but with my doer attitude that got my hands on everything I possibly could help, I got promoted to be the COO of the company with a team of 20 people after 3 years. I was really lucky to be offered such a big responsibility when I was still fairly young.

But during that one year I was in the COO role, I kept questioning myself whether I was happy running physical stores and where I saw myself in the next couple of years.

I decided it was time for me to move on because deep down in my heart, I was craving technology and wanted to get myself back in software.

“I’ve got to follow my heart to be successful.” That’s what I told myself.

So I left the company without any plan, and took the time to figure out what’s next.

My background was a bit of a mess really, a mix of knowledge in business, tech, product, operations, and human resources. People like to call that “jack of all trades”, but I wasn’t sure what I was good at.

A Rare Opportunity Popped Up

I was looking for an “interesting” tech startup to join. Good mission, good culture, and a good team, a place where I could put my knowledge and skills into practical use.

There were some startups in Luxembourg, but being a small country, you can imagine there weren't a lot of good options. Through a friend’s referral, I got to learn about this local startup called Astry.

After checking it out briefly and getting impressed, I sent an email to the co-founder & CEO, Steven, telling him about my interest. I was surprised he got back within the day and we quickly set up a time to meet at a coffee shop 2 days later.

Astry was a B2B2C SaaS platform that allowed merchants to set up their e-commerce store. It had a full suite of tools for businesses to interact with their customers via events, referral programs, and surveys. I thought that was pretty cool given the rise of e-commerce.

I met Steven and the other co-founder, Josh, for the first time, and then I met Steven 2 more times. All three conversations were casual, purely getting to know each other and sharing our background and aspirations.

Honestly speaking, since there weren't a lot of quality startups in my city, I was quite interested in joining them just by judging the book by its cover. And here’s why.

1. They had a big vision to revolutionize the e-commerce space by building this mega ecosystem and they sounded like they had a plan to tackle it.

2. The metrics they showed me looked pretty good. I thought about working with the team to bring it to the next level.

3. They grew the team to 20 people in 2 years, a size that implied they’re slightly beyond early-stage.

4. They had a semi-remote international team with people in Europe and Asia. I went into their office to meet the local team and I liked them. I could tell they were all great people, humble and have no ego attached. This was key to me no matter where I worked.

5. Lastly, they had really amazing UI and visuals. The product, the marketing site, the slide decks, everything they showed me looked great. It was hard to find such quality elsewhere.

Because of my experience in expansion, marketing and operations, they wanted me to lead the expansion team. Just that this time it wasn’t about store expansion, it would be user acquisition to the platform.

Completely different, and something I had no experience in. But hey I was up for a challenge if they believed in me.

After we agreed on the terms, I said “Let’s do it!”

All sounded good so far, and I honestly didn’t know it would be the beginning of a traumatized experience…

What Went Wrong?

When you join an early-stage startup, you can expect a few things.

You know there isn’t any process to follow, you know things would be messy, you know there would be a lot of junior team members you’d have to look after … but what Astry had was beyond all these.

Let me share my observations here.

> There were 20 people on the team, roughly 60% Product & Engineering and 40% Sales & Marketing. The two teams didn’t talk to each other at all and were in the process of splitting into 2 separate offices when I joined.

> The mentality of the co-founders was that hiring would solve the problems, and that was also why I was brought in. They hoped that someone with experience in certain areas would come in and brought changes, structures, and growth to the company.

> Steven, the CEO, spent most of his time having 1-on-1 with different colleagues. In my first few weeks, he nudged me for a quick catch up frequently. Most of the conversations were him convincing me of his new ideas, and they were all one-way communication. I assumed the conversations with the others would be the same. Because these conversations were held in private 1-on-1, everyone got different messages and the team wasn’t aligned at all.

> Vanity metrics (e.g. total number of users) were celebrated. The numbers were reported from the team to the CEO to the board. As a SaaS platform, there was no emphasis placed on activation, retention, MRR, churn etc.

> There was a key strategy that the sales team deployed: cold emailing and cold calling. What the team did everyday was to dig out more contacts and reach out to them to convince them to try our platform. On the marketing side, there were blog posts being published but the strategy was hiring university students to write them. There was no distribution, so each blog post had an average of less than 10 views.

> The product strategy was also extremely frustrating to the whole team. The product team never talked or interviewed any users, and the roadmap was filled with feature requests from customers the sales team was engaging. Our strategy was to treat these custom requests as feedback to enhance our product that could potentially serve other users.

> The team was full of imaginations. There were a lot of talks about how we could change the world, how our product made people’s lives better, how we represented a new way of doing things. And there was no user research, interview, or data to support any of that.

> Finally, there was a weekly evening video call for the senior team to gather with the chairman of the company. The call was mainly about the CEO sharing the latest updates to the chairman. This was strange to me and the other senior managers, because I was so new there, I just followed.

Now you know why I said it was a traumatizing experience.

If the average startup survival rate is slim, I thought the chance for this startup to thrive was zero. 

And I couldn’t help myself but to come up with a lot of reasons why I had to get out as soon as possible. 

After 6 weeks of my head spinning in circles, I handed in my resignation.

At that time, my biggest question was why my colleagues, some talented people, stayed there. I later found out that some were planning to leave but wanted to see how things went for a few more months, and some of them didn’t even bother as they were getting paid.

Is that a common mentality for most employees? Why waste precious time waiting for change instead of proactively taking control of your life? I couldn’t do that.

I was aware that it was partially my fault to let this happen, because I didn’t drill deep in the conversations we had to fully understand how they functioned as a company and as a team. Things like these should have been pretty obvious to spot.

Anyway, I was ready for a new chapter of my life and put all this behind me.

Little did I know that by being honest and blunt, the biggest offer in my life would be showing up soon ...

Key Lessons
  • Anyone can make a startup look great and promising from the outside. Before joining or partnering with one, make sure you dig deep to discover their vision, priorities, culture, team impact etc. These 40 best questions to ask in an interview can help you.
  • Once you find out the company is toxic, a lot of people choose to wait to see if things will change. Don’t. Toxicity comes from people. Only if you think the people would be changed in the short run, spend your time on better things.

“You didn’t do enough homework before joining them, so it was your fault.”

I agree. I was sort of blindsided. At that time, I was working on a side project for 3 months and was stuck, which made me want to jump at the first opportunity I got. I always believe that everyone is responsible for their own experience, and I never regret these 6 weeks because I learned how to properly assess a company.

“They hired you to change things, you should have stuck around to do that.”

As selfish as it sounded, I honestly couldn’t. When so many things were going wrong, and I woke up every day frustrated, I had to take action. I’m one of those people who need to find passion and order in my work. If there isn’t any, I would much rather not waste my time and their time because life is so short. And remember, no one can make the decision for you except yourself.


Written with ❤️by Jessica Leo. All rights reserved.

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