Big Tech or Startup?

Every few months, I have a conversation with a mentee or an acquaintance who is considering job opportunities in big tech (Microsoft, Google, Facebook, etc.) or a smaller startup.? I have worked in both, and am always happy to share my stories and opinions, but unfortunately, my answer is usually not very satisfying: both are great depending on what you are looking for!

A quick summary of my CV for those that may be unfamiliar.? I joined a small, Canadian-staffed startup called Quack.com – an early voice portal company during college. Think Moviefone but with voice recognition and support for stocks, news, and weather1.? This was during the first Internet bubble, and it was a wild ride.? Quack moved to Silicon Valley, was eventually acquired by American Online, and moved into the Netscape2 campus in Mountain View.??

Later, a core group of engineers from Quack started a company called iSemantic.? We set out to build a distributed, in-memory database and rules engine with the hopes of changing the way enterprises process big data (think Snowflake). Our tech was pretty awesome, but our timing sucked. Between the time we locked ourselves in a basement coding, and the time we emerged one year later to secure our first round of funding, the Internet bubble burst, and there was no VC to be found.? I went back to school, finished my degree, and spent the next 18 years working for ‘big tech’ (first Microsoft, and now Google).??

I have honestly loved my experience at both startups and ‘big tech’. And, although I have chosen to spend the bulk of my career working at large companies, I wouldn’t trade my startup experience for anything.? That said, I usually end up giving this speech when I am trying to talk an intern or employee out of taking a job at a startup – so there is probably a bit of unconscious bias in the way I frame my arguments.

One of the things I have loved about working at companies like Microsoft and Google is the quality of talent and the depth of experience around me.? I am almost always the least experienced person in the room, and I have had the chance to work with the best of the best.? Have a question about some programming language issue you are hitting – Anders Hejlsberg is just down the hall.? Not sure how to tackle a systems management issue – Jeffery Snover is on the treadmill next to you at the gym. Need some help thinking through a distributed computing problem – sign up for office hours with Mike Dahlin .?

But it isn’t all about the “big names” in tech with fancy Wikipedia pages3 - it is about getting a chance to workday in and day out with dedicated professionals with extensive domain knowledge.? It is about having a legal department to help answer questions and keep you out of jail. It is about having a user experience team that will help you craft the perfect user interface. It is about having a marketing team to ensure you are building something that your customers will use.?

In a startup, you are the legal department, user experience team, and marketing department.? If you hit a challenge when working on a project, there is no one to escalate to – you need to solve it.? Depending on your character and mindset, this can be incredibly empowering and liberating or extremely frustrating.? If you are an experiential learner – startups could be the right place for you.? If you do your best in a structured learning environment – you may be best to stick with larger tech companies.

The next factor to consider is your tolerance of risk. While working at large tech companies is not entirely without risk , you can generally assume that your job will be there six months from now.? You can build a lifestyle around this and even buy a couch .? This is not true of startups where 90% fail .? Generally, this means you need to be in one of two situations: you have nothing to lose or enough of a nest egg that you can afford to fail.? I haven’t seen the statistics, but I would be willing to bet startup employee age distributions follow an inverted bell curve – with the vast majority under 27 or over 43.??

When I first started at Microsoft, I told myself that I would leave within a couple of years to do another startup. But after a few years of a stable paycheck, I found it very hard to leave.? It is only now, in my mid-forties, that I feel confident enough to pursue a startup. So I suppose this is my way of saying that if you are young and you think you might want to join a startup – you should probably do it?.

Before I end the article, I would like to touch on a couple of ‘myths’ about startups - or what I would call ‘bad’ reasons for wanting to join a startup.? The first is the myth that the only way to get rich in tech is to join a startup.? If you are a twenty-something engineer, the truth is that unless you are exceptionally fortunate (think Microsoft in the 80s, Google in the 90s, or Facebook in the aughts), a successful startup ‘exit’ probably means enough money to buy a nice car or put a down-payment on a house – not buy the Dallas Mavericks . The people who get rich in startups are generally the initial founders, investors, and business executives that get brought in along the way.? The engineers do well – but the money isn’t life-changing.? A stable salary from a large tech company, well invested over the course of a career, will net out to be the same or more.

The second myth I want to touch on is that in a startup, you get to throw off the shackles of oppressive processes and tools enforced by your management chain and do anything you want.? In ‘big tech,’ the limiting factor tends to be management and process – in a startup, the limiting factor is time.? Between researching GDPR requirements, hacking in features for VC demos, and touching up your business plan, you will probably not ever get the chance to return to the code you wrote and add in that cool new feature you wanted. In ‘big tech,’ the limiting factor tends to be management and process – in a startup, the limiting factor is time.??

One of my superpowers in big tech has been finding ways to fund my crazy ideas.? When I left Microsoft, I handed off a directory containing over 40 prototypes – many of which were productized and turned into multi-million-dollar products.? It is possible to get your ideas funded and make a difference in big tech – you just need to be patient and learn how to navigate your org?.

In summary, the ‘good’ reasons for joining a startup are that you are an experiential learner, and you thrive in a chaotic environment.? You are willing to take on any challenge that comes your way, and you have a high-risk tolerance.? The truth is you will probably not become a billionaire, and you won’t have limitless freedom, but you will likely have a lot of fun and learn a lot.??

Do you have experience in a startup or big tech?? I would love to hear your thoughts in the comments section below.??

Be Happy!

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Footnotes:

1. ?If you are under 35, Quack and Moviefone sound weird.? But, when candy bar phones were all the rage, having an easy-to-remember phone number that you could call while going to get movie times was a seriously awesome idea.
2. Again, I find it mildly disturbing the number of new grads these days that give me a blank look when I mention Netscape.? In the 90s and early aughts, Netscape *was* the Internet – commanding over 90% of the web browser market.? The share fell to less than 1 percent in 2006 (ref ).? We probably need to start teaching ‘internet history’ in school lest we forget how fast the tide can change in our industry.
3. If you are sensing a bit of jealousy here you are not wrong.? Still hoping to get this someday – and for a good thing – not those fires I set in high school (joke)
4. If you are one of my interns or employees, totally ignore all of this advice.? A startup won’t be any fun at all, and you should take the job I am trying to talk you into!
5. I have added ‘how to get your ideas funded’ to my article backlog.

Please note that the opinions stated here are my own, not those of my company.