One Door Closes, Another One Opens: A Startup Cautionary Tale

That Thursday was supposed to be a regular day in the office; everyone still slightly hungover from holiday baked goods and just beginning to fall back into routine. The usual faces greeted me as I emerged from the narrow, carpeted hallway. Casual greetings of “Good Morning” and “Happy New Year” trailed behind me on the way to the Keurig. My morning coffee routine – 12 ounces, Sumatra Reserve, in a matte black mug that read “Stop! I don’t have time for bullshit today”.

My first clue to the trajectory of this particular Thursday on the startup rollercoaster: my boss had not shaved in a while. Of East Coast decent, he’s not the kind of guy known for presenting himself at any level of unkempt. As he walked out of his office toward the conference room for our last-minute management team meeting at 9am – the beginning of the work day – his walk seemed off-kilter. Given that it was a mere moment in time, I can’t quite describe the air of dismay in his step or what caused the bottom of my stomach to twist, but I had a feeling.

Normally, today would have been my work-from-home day, but I had gotten done with my 6am yoga class only to find a text message from my boss requesting my presence in the office. He did not give a reason. Being that I absolutely love my job and consider myself very fortunate to be part of the management team, in less than an hour, I got myself together and arrived at the office. Little did I know what the day had in store for me.

At 9am on the dot, the management team all acquiesced to the impromptu meeting and took the usual seats in the main conference room. The table was large and made of finely finished dark wood, surrounded by eight tall leather black swivel chairs.

After a few minutes of pre-amble, explaining that we had been actively seeking funding, and that we had been unsuccessful (this was news to me as I was highly involved in all the investment pitches from the beginning), he said the sentence that deep down I knew meant it was really over:

“Effective immediately, everyone is terminated, including myself.”

I don’t remember anything that was said after that. The shock had crippled my mind and my stomach felt as though someone had piled rocks to the top. So many questions came to mind but none of them made it to my lips: how did this happen? Why did this happen? We were so close! Six months away from having a product that would blow the market out of the water (a market that, by the way, will be worth $1 trillion by 2025 according to Frost & Sullivan) and our investor was done. No warning, no severance – just done.

They say that all is fair in love and war…but what about business?

It had been a wild nine-month journey since I started at the company. I was originally interviewed for a software developer position to work on an ETL tool that would expedite the process of getting clients off the legacy platform and onto the newly built platform. The new platform boasted a React front-end and a React Native mobile app. It was shiny and new and it demo’d fantastic. The only problem was, as I would soon come to find out, that we did not have the right team with the necessary skills to go-to-market, let alone develop the product to become something that was remotely competitive.

After my initial interview and whiteboard algorithm challenge (with the Director of Engineering who wasn’t an engineer), they made an offer to me with the title “Product Manager”. It was the first I had ever heard of the position, let alone the entire department. Product seemed like my calling, as I was dubbed to be too valuable in communication and presentation skills to be stuck sitting behind a computer coding all day long (even though it’s something that I loved to do). I had just graduated from coding bootcamp (Coding Dojo Dallas) two weeks earlier. I was hungry for a paycheck, having lived off credit cards for four months during the full-time program, so I accepted my first offer and started the very next week.

Fully immersing myself in the Product life, I read books on AGILE/Scrum, product development and cautionary tales from founders and CEO’s of technology startups. I wrote everything down in Evernote and became known as the “girl who always brings her laptop to meetings” to take notes. I wrote over 72 user stories, got waist-deep into the market to understand the competitive landscape, and created a GAP analysis to assess what was missing in the new product vs. the old product.

I quickly came to the realization that the company’s position was overinflated during my interview process.

Despite this realization, I continued to work on the product, attend sprint planning, and battle the uninspired development team that only showed up to the office when they felt like it. I had never before worked with so many people who were unwilling to put in the time and effort – I was raised to bring home A’s and that is exactly what I planned to do.

The development team at the time was not my biggest fan from day one. I can remember feeling so out of place – most of the employees had one foot out the door and those that still had two feet in were not working, leaving early and sometimes not even showing up at all. There was no thought or direction, no planning from the management team, and outrageous spending of the development team (a you want it, you got it! attitude). Even though this was before I had experience dealing with P&L’s, I knew that the way things were could not possibly be sustainable.

Still, none of these challenges phased me. I spent a few years running equestrian facilities, working as professional rider, and even mucking stalls and painting fences in 105 degree Florida weather – I know hard work. I was convinced I could be the one to breathe life into what could be: a decent brand and brand strategy, value propositions I could buy into, and the overarching theme that we were driving down energy cost and consumption – because who doesn’t love the idea that you’re helping major corporations save the planet? For the first time, I felt like I was making a difference on a larger scale. In fact, my feelings of accomplishment were re-enforced when attending Dallas networking events and describing my business to total strangers. When you serve a larger purpose, it’s easy to get behind the bigger picture even if things aren’t as good as they seem on the surface.

Despite my greatest efforts across product, marketing and business development – involved in everything from high-level strategy presenting to the board and investors to creating marketing collateral for the sales department.  Despite re-launching our company website in just four months as the first phase to our net new digital lead generation strategy. Despite the amount of time I poured into our strategic reseller partnership with a Fortune 200 company – when the announcement was made that day, none of it mattered.

Everything seemed so surreal. Once the management team was done with asking questions about what this meant for all employees – health insurance (no option for COBRA), severance (there wasn’t any), and paid time off (will not be paid out) – then came the time to announce it to the rest of the company. As if this weren’t a hard enough announcement, we still had a handful of people out on vacation. I can remember thinking “at least I was here, at least I felt the finality of it all and I got the opportunity to say goodbye”, because not everyone else was so lucky.

We crammed everyone from the office into the same conference room to announce the news. We let the CEO do all the talking, and I remained silent while holding back tears. Everyone was angry, and rightly so. We had just spent over a million dollars hiring a fresh, senior-level development team that had accomplished more in Q4 than the last team had accomplished in a year. They had left good, safe jobs at large corporations to take a risk on something small and innovative. Out CTO was very picky about who he hired, and a recent new-hire himself. He had spent months rebuilding a team that had all but disappeared, and just when things were looking up, the rug was pulled out from beneath us.

“Why didn’t we know about this? Is there a reason it came out of the blue?” one of the more vocal developers asked sternly. The CEO replied that we had been working on securing funding for a while and that this is just “how it is” at startups. Very matter-of-fact, void of emotion.

The one consolation we were all afforded: everything in the office was up for grabs. Within an hour, of which I spent wandering, chatting, processing – the entire office was turned upside down. TVs were ripped off walls, monitors were put on carts and even the ping pong table was claimed.

It’s crazy to think that a company could just vanish into thin air. But it did. And here I am.

I choose to look at my time at Flywheel as the opportunity of a lifetime. I was privileged to experience things that individuals many years my senior have not. I was involved at the highest level of financials and business strategy – a tremendous opportunity for a 28-year-old who considers herself “bad at math”. I sat through board meetings, I pitched to investors, I helped train a Fortune 200 channel sales team. I created company collateral that would be shown to household brands, I learned a tremendous amount about energy management and sustainability, and I got to improve and grow my skills in Adobe Creative Cloud, product design, web design, digital lead generation, and so much more.

There are so many things to be grateful for that I look to this next chapter in my life as an open book rather than a lost opportunity. As my boss would say when it came to hiring anyone to handle a new project, “I want the person that’s done this before, that’s failed at it, that’s learned from it”.

As one door closes, another one opens.



  1. Great Blog Cat! I / we knew you were great the first time we met! I hate that this happened to you so abruptly- especially with no insurance or severance! Ouch! Been there done that! It only made me stronger and more determined to realize my worth and go for the gusto. I hope we get to work together again soon! ~Kat


  2. Loved this post! I’ve been considering doing one of those coding academies myself because I’m in need of a career change. Would you be able to answer some questions for me? I’d love the perspective of someone who has actually been through it!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.