Why I left big tech for startups in 2021

I spent the first ~7 years of my career at large companies, primarily in Big Tech (Salesforce, or SFDC as they say), with a brief stint as an accountant and strategy consultant (woof).

At the end of my tenure at SFDC (and even at Oliver Wyman), I was sick of bureaucracy and knew it didn’t align with who I was deep down - a scrappy builder who doesn’t like to be told “that’s just how we do things” with no or outdated logic aligning to why a decision is made.

The bottom line is I push back and reject dogma more than ever now. I’m sure it’s something Julian, Cailen, and even my wife want to pull their hair out over at times 😆.

Because I made the transition from a big to a small company (and wrote about it), I have spoken to countless people (usually via LI DM reachout) who are looking to make the same transition, feeling unfulfilled in their current path, but want something more.

They want out of a big company and into one where they’ll have more impact; usually, that means a startup.

To articulate the difference between the two paths (bigco vs. startups), the best analogy I’ve seen is the pitch Jobs gave prospective developers when they were contemplating joining Apple vs. The Big Guys (IBM, Microsoft, etc.) in the 1980s: the pirates vs. the navy.

I admire Apple for their world-class branding and beautiful/elegant products, but mainly admire Jobs for always thinking from first principles, his thoughts on life (his Stanford commencement speech and notes he wrote on his deathbed are a must watch/read), and his distaste for consulting 😎.

Jobs used this framing of the pirates vs. the navy to motivate his current “motley crew” developers; they were significantly under-funded and under-resourced compared to the big guys, but they wanted to stay for a broader vision and impact, mainly, with, yes, an upside of financial returns should this go well.

According to some of these devs:

This tale of being a pirate would come to be the metaphor that symbolized the anti-establishment movement that drove Apple in its early days.

Jobs even created his recruiting strategy around this:

As with most things in life, it’s all a game of tradeoffs - there isn’t a right or wrong path generally + it depends on where someone is in their life + what motivates them.

If you choose BigCo:

• Pros:

  • You get stability (or at least the feeling of it) - I’d challenge this, but this is what most people note about working at a big company

  • You get the status/brand halo of that company (Ex-Google) - in some circles this is great, but in others not so much/indifference

  • Lots of resources for you to do your job (and benefits as well)

• Cons:

  • Less individual glory or agency - you don’t have as much of a feel for impact

  • Corporate bureaucracy and politics (you move up more from optics than you do performance/impact a lot of the time)

  • Less opportunity to do things outside your job

  • You run into more NPCs (non-player-characters - which is corporate America’s version of a GDI/Narp)

  • Classic golden handcuffs

  • Lots of talk of innovation, but risk aversion kills a lot of bold ideas

If you choose startups:

• Pros:

  • Building skills that mimic those of running your own business (due to you having fewer resources)

  • Financial upside of equity

  • Career accelerant & network effect (why you should join a breakout)

  • Feeling of impact/ownership from your day-to-day work - you feel like you’re personally building something

  • Upside of equity

• Cons:

  • So many ways a startup can fail - and that is what makes it risky (I have friends who are sharp as a tack and still haven’t found their home run)

  • Burnout risk - you work more at startups, and always need to be “on”

  • Bad equity outcomes are way more common than a good payout

  • So many fewer resources (for some, this is great/forced learning, and for others it’s a nightmare)

  • Immature/crazy founders who don’t get GTM/sales

  • Less cash/guaranteed comp

I did this breakdown when I was leaving big companies, and realized my heart was much more in startups.

Then, when I was at startups, I realized even those were too big, and I started VibeScaling earlier this Winter and finally found my “thing”.

It’s all about experimentation to get closer and closer to your Ikigai (what you’re good at, what you like doing, what you can make money doing)

As mentioned, there really isn’t a right or wrong answer to joining BigCo vs. a startup - they both have tradeoffs and pros/cons.

The question you really need to ask yourself though:

Are you a pirate, or are you a sailor?

Till next time 🫡,

Chris