The Harsh Reality of Working for an Early Stage Startup

March 14, 2015

8:00 am

What do you think of when you hear “I work for a start-up”? Probably something that resembles the latest GoDaddy Superbowl commercial of a self-employed man hard at work instead of watching the game like everyone else. Or maybe you’re thinking of something out of Silicon Valley: young 20 year olds working with their best friends surrounded by laptops, beer, and ping pong tables before hitting the big multi-million dollar buyout. So what is it really like working for a startup? As Ben Horowitz has said in his book The Hard Thing About Hard Things, there is no recipe. While every startup is different, there are still shared experiences that everyone can benefit from.

This guest article was submitted by Belinda Chan, Chief Client Officer at

Below are the startling experiences that taught me key lessons that I wish I had prepped for prior to joining a startup. This is the harsh reality of working for an early stage startup.


“Do you think it’ll be a challenge moving from a big agency to an early stage startup?”

I had done the small mom-and-pop marketing shop, the rapidly growing tech company, and the conglomerate sized advertising agency. I knew I wanted to return to a small company in the tech space where I would play a major role in shaping process and strategy. I’m talking “less than 5 people” kind of early stage, which was something I had never done before but looked forward to the challenge. So did I think it was a change? Probably nothing I wouldn’t be able to get accustomed to within a few months.


“Poshly? Never heard of it”

Try about a year. I went from a spacious cubicle to having no designated work space, computer, or phone. Not having a place to call my office became a metaphor for the persistent feeling of driftlessness and sometimes crippling insecurity that I would live with for the next year. I knew it seemed trivial, who cares that I didn’t have a desk or that I was lugging my laptop everywhere, or that no one knew anything about the company I worked for? Perhaps it didn’t matter at 30,000 feet, but when faced with it every waking hour of the day, that blasé attitude quickly turned to uncertainty and confidence-destroying resignation. What I realized was I was letting my ego get the best of me. I knew I had joined a great company, I just had to keep reminding myself of it. Taking sales bootcamps and practicing my pitch at conferences of all sizes only helped to build up my confidence. So when that uncertainty reared its ugly head, I knew it was just a passing phase.


“Have you had a big, dramatic, ‘this is it, make or break’ moment yet?”

The startup industry is in the business of high risk, high reward, appealing to both the young millennial dreaming of a big payday and the industry veteran looking to impart a career’s worth of expertise. What I should amend in the quote is, it’s not a big, dramatic moment, but the small and steady pile-up of many moments. What I didn’t account for was the pervasive burn of daily stresses. That was my true test of strength and staying power, and now I make sure to ask future hires how they handled their busiest day and if they would be able to deal with their busiest day every day for potentially years.


“We now have new team members joining”

After months of fundraising and careful selection of applicants, we were greenlighted to staff up. Suddenly I was manager to two new team members who would be taking on some of the responsibilities that I had mastered for the past year and change. Imagine my surprise at my sudden reticence to hand over the very tasks that kept me in the office until the wee hours. Somewhere along the way, I had fallen into the trap of “mine” and not “ours”, and didn’t want to see changes to my process, my methods. I had lost sight of the goal of any and every company: to continue improving, and had fallen down the loathed but slippery slope of entitlement. Entitlement had no place for the evolution of a company.


Each lesson, despite its catalyst seeming small or mundane, taught me to become a better worker, a better colleague, and a better teacher. Sometimes it takes the tedious to wear you down and not the big splashy trials and tribulations that seemingly would push you over the edge. It is the unexpected, hiding in plain sight, that teaches you the biggest lesson. Now with Poshly approaching its third birthday and most impressive year to date, I’ll be ready to face a whole new set of challenges.

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Previously the Managing Editor at Tech.Co, Ann Diab has a background of launching and nurturing of startups and tech companies. Empowering and educating entrepreneurs and startups to better productivity and culture is her passion. Growth Manager at WorkingOn to enable folks all over the world to enjoy work and improve communication. Follow me on Twitter.