6 lessons I learned going from a Fortune 500 to an Early Stage Startup 🚀

I graduated 🎓 in 2018 and landed my first job at a fortune 500, except just a few months of internship experience under my belt I did not know what to expect from my newly found corporate life. Months after navigating through the intricacies of a 100-year-old company, I decided to join an early-stage startup to take up new challenges and expand my skills while creating something from the ground up. Here are the top six lessons that I have learned so far going from a Fortune 500 to an early-stage startup:

1. Virtues of Adaptability

Source: Venture Burn

Working at a startup, you will be expected to juggle between different roles - hiring people, hacking customer success, laying down your processes. More than often, you will find yourself biting off more than you can chew. To some, this may sound like a deal-breaker, but in the long run, it can open up more doors than you can count. This constant fire 🔥 will remodel the way you think about businesses and teach you the virtues of adaptability.

On the other hand, bigger companies will not make it easier for you to switch roles with that much agility. The experience of working in a startup, where things are changing every day, will teach you to embrace and adapt to change rather than resist it.

Few days into my startup job I was working with the customer success team, hiring people, creating software, understanding customer behavior and doing much more. This has forged me into an all-round wizard who is confident to get things up and running without waiting for professional 👨‍⚖️ intervention.

2. Perfection is a Mirage

Source: Wall Paper list

On a random Wednesday Morning:

Customer Success Person: “Folks, X feature will solve Y problem for 95% of our users, we need this by the end of this week.”

Product Person(Looking at the Tech lead with puppy eyes): “What do you think?”

Tech Lead(After 2 minutes of silence): “Okay, we will do it!”

Founder(Smirking): “Good!”

Conversations like this will be a commonplace at an early stage startup, where, things are changing almost every day. Working in such an environment will teach you one important lesson - the importance of getting sh** done and to always be ahead of your curve. Unlike Fortune 500 companies, where, everything is done in a very methodical manner and the risk is spread across a number of people, creating bureaucratic roadblocks - culture at startups is for all the right reasons mostly horizontal, mitigating the sloth-like movement.

Early-stage startups are often in the middle of finding a product-market fit, controlling all kinds of churn, and much more, things need to move fast and perfection just doesn’t fit in the equation. As I like to put it - “Done is better than Perfect”. Lean thinking is what will help you thrive in such a fast-paced environment, and you will be running faster than the “road runner”.

3. Work Life Balance is a myth

Source: Quotez

“Run, Forrest, run 🏃” - that will be your first day, and all the following days working at an early stage startup. Everyone around you will be running around with a stack of monkeys sitting on their shoulders, and the thin line between your work and life will start to get blurry. The time commitment that startups require is beyond 9 to 5 grind.

Startups are notorious for last-minute projects, and more than often you will find yourself submerged in a pond of tasks, staying behind the office after hours to get that last-minute project ready for the urgent launch. Attending a weekend call with colleagues may sound daunting, but getting great ideas off the ground takes a fast pace and an all-out dedication.

It will become essential under such fast-paced circumstances to keep a check on yourself and to make sure that you are not on the verge of burning out. You will often need to take a step back and reevaluate the benefits of maximizing your time.

4. Failure is Success in disguise

Source: FastCoDesign

Failure seems to get more attention than success. We try to mitigate it, fret it, doubt ourselves every time an unconventional idea falls our way. But we forget that - success comes to those who stumble from failure to failure, taking one lesson at a time, excelling in what they’re after.

Entry-levels at Fortune 500s are structured so it is almost impossible to fail, which is indicative of the fact that the rules are tightly set. It ends up making for little mistakes and much boredom. On the other hand, at small startups, there are no safety nets, you fail, you learn, you get up and you start over.

After all, learned are the people who know how not to do something because they have already tried that and failed at it. Edison and Dyson are two classical examples of such learned individuals.

5. Measuring what matters

Measurable actions within a set time ⏲ frame can help us to focus on the initiatives that can make a real difference, deferring the less urgent ones. Oftentimes, we set goals and targets, but forget to quantify them and end up scattering our energy in achieving things that were never on our agenda.

One thing that I have learned throughout my startup career, is the art of setting up SMART (Specific, Measurable, Achievable, Relevant, Time-Bound) goals. It has helped me focus my time and energy on what matters, benefiting both me and the business. Setting goals might not sound like a herculean task, but setting up SMART goals takes deep thought and effort, it forces us to think multi-dimensionally. At a startup, no one will be setting goals for you. It will be on your shoulders to understand and assess what needs to be done and how you will measure success or failure. One thing to keep in mind is to make sure that the goals are always aligned to the company goals.

Another benefit of quantifying goals is, that it makes it easier for us to periodically reflect upon how we’re progressing. This activity involves taking a broader view and assessing whether the whole system is working for us or not.

6. What about wealth?

Source: SlideShare

Working at a big company, one is more likely to earn a career worth of income in less than a decade. The same is not necessarily true working at a startup. In the startup world, people seem to have a lottery ticket with less than 1% chance of paying off for very early employees - that too only if you got any options when you joined.

If you are young and start working with people 5 to 10 years older than you, chances are that you will not be taken seriously, unless you can pull some really cool magic tricks from your hat. Working at startups is great to sharpen your skills, but no one will promise you a life-changing amount of wealth unless you are working at the next Google - chances of which are really really slim in the practical world.

Published 3 Feb 2020



Rishabh Madan on Twitter