Ditching A Big Co? Here Are 5 Lessons Learned From 20 Years In Startup Land

Making the move to startup life can be a great experience. Here's what you should know.

For a lot of folks in the tech industry it’s been rough out there. Since the layoffs began in 2022, there are now over 250,000 talented, smart, and creative individuals who have been laid off, with many of those layoffs coming from the larger publicly traded tech behemoths. If you are one of those individuals, now might be the time where you are considering dipping your toes into the startup scene. Sure, large tech companies can have huge financial rewards and career opportunities, but startups can also be a place to learn and grow your skills by orders of magnitude. 

This chart shows the estimated number of jobs cut in the largest layoffs by U.S. tech companies since 2020.
Source: Statista

From my earliest days out of college until now I have been working in one way or another as an engineer within the startup orbit. The fulfillment of working at a startup through all of the challenges and opportunities to build something that can have a lasting positive impact on the world is bar none.

For anyone out there who is looking to get into the startup world I would highly recommend taking the opportunity should it come your way. Of course, not every startup will become a huge success and many fail along the way, so it’s important to be honest with yourself about what you are looking to get out of a startup and what you want to give to help it succeed.

Not every startup will become a huge success and many fail along the way, so it’s important to be honest with yourself about what you are looking to get out of a startup and what you want to give to help it succeed.

Whether that was working for an agency to help build some early stage startups or working directly at startups themselves, here are some of the lessons that I have learned along the way. 

Startups are messy

One of the first lessons I learned about startups, and companies in general, is that they are messy. Every single one of them.

They all have various levels of mess, obviously, but the goal is to be as scrappy as possible while giving yourself the highest chance of success. That typically means getting prototypes of your product ideas in front of potential customers as soon as possible and starting to learn. You don’t do that with highly polished products, and usually not with battle-tested business processes either. 

If your goal is trying to find perfection in all areas you are destined to fail. You must allow things to be a bit messy sometimes as you focus on the priorities that matter the most.

This is part of what I love about startups, you get to be intentional about the things you are going to prioritize and care about, all of which typically have a direct impact on the end-user. It also resonates a lot with me in how you have to approach raising a family.

If your goal is trying to find perfection in all areas you are destined to fail. You must allow things to be a bit messy sometimes as you focus on the priorities that matter the most.

Investment can change culture and priorities

I also learned how much investments can change company values, culture and priorities. This is often overlooked as a lot of early stage companies are trying to raise capital, which can be a challenge in even the best of economies. 

Not all money is the same 

Some investor demands, even the most innocent of ones, can shake the foundation of companies with great potential. The demands of rapid growth are the most obvious culprits, but even the values the investors bring can cause monumental changes in how a team operates. 

I once had a leadership coach tell me that “people respect what you inspect”, and I think that’s particularly true for investors. If they are constantly asking about your ARR, you will find ways to make it improve. But sometimes focusing on the wrong things early can destroy a company before it even has a chance.

All companies will eventually fail without great people

Companies without great people will eventually fail to meet the demands of their customers, or will fail to attract talent to solve customer problems. 

I have met some of the best people in my life through my work, and I don’t think that’s an accident. When you build a workplace with meaningful values you attract great people. It’s hard because sometimes that means a lot of time and interviews, but it always pays off. 

When you build a workplace with meaningful values you attract great people.

We all know a bad hire is one of the worst mistakes any company can make, particularly in the earliest stages. A concept I like to apply here is to pretend your customers are interviewing your next hire, who would they be looking for?

Experience matters, a lot

A rare and important point about Hoop as a startup is that we are a team of people that have done this before. So often with startups one or more foundational team members are learning how to build a product, business or team. This leads to very important but costly mistakes along the way. 

That’s not to say we won’t make mistakes, we will, but we will all use our experience to learn and pivot faster and with more conviction that we would otherwise. Crucially, it also means that we will be able to “find signal through the noise” a lot quicker, which is something that I’ve seen startups and products struggle with for years.

Value the customer at all costs

If there is one theme I’ve seen across all the companies I’ve worked with, it’s that you have to value the customer above all else. Not just gathering revenue from them, but valuing them at a deeper level and being willing to throw away your previous assumptions about what’s best. This is what leads to the highest potential lifetime value of the customer, but also gives them the most satisfaction in using your products. 

It’s a bit like charity work, the obvious reason to do work for others is that you’re helping your fellow humans. But the fact that it actually feels good to do it is what ultimately keeps you coming back.

At the end of the day, choosing the startup life comes with all of the risks and rewards, the stress and excitement, and life changing experiences you can imagine. If you're a passionate builder who wants to be involved in something bigger than yourself but not so big that you’re just another cog in the wheel, then working at a startup might just be for you.

Save time. Work smarter. Try Hoop today.

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Save time. Work smarter. Try Hoop today.

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