Grow with, not through

In the startup community, it’s a pretty standard trade-off… Do I “take a risk” and join a startup, or join a more established business?

In the Stanford computer science community, where Peter Thiel’s Zero To One was born through a series of on-campus lectures, there is an expectation that the startup path is the dominant choice. However, more often than not the graduates I talk with are taking the conservative path. These could be great opportunities such as Google in Mountain View or Atlassian in Sydney, but ultimately the days of exponential growth are in the past.

I’d like to drive one point home about why your career development opportunities are better in a startup:

Opportunity comes from growth, and there is more opportunity in the growth around you than in your individual growth alone. 

Does the baby boomer generation have so much equity in housing because they grew better individually than millennials, or because of the economic growth around them?


When I graduated in 2005, “startup” was not a common term. In 2005 the dot-com bubble was in recent memory, Facebook was known only to a handful of US colleges, and the iPhone was 2 years away. Management consulting firms were sucking up engineering talent and most engineering options were sparse and uninspiring (think oil & gas production).

I could have joined one of the consulting or large engineering firms and it would have looked something like this triangle-shaped org chart over time:

I would have worked hard and slowly moved my way up the org. However with this structure I’d be working with graduate peers and under management that only started ~2 years before I did. I’d be unlikely to work closely with senior leadership or the CEO until much later in my career. This limits my direct exposure to key parts of the business until many years after my start date.


Instead, I was lucky enough to join a small team who built complex analytics software.

I joined this company not because startups were sexy (they weren’t in 2005), but because I saw the opportunity to work directly with a small group of talented individuals whose ambition was to build something much bigger.

This was an opportunity to grow with the business and to work directly with leadership. I saw first hand their decision making and approach to growth. I was mentored by leaders far more capable than I was; far beyond the opportunity of a role in a more mature company.

This startup tripled in size before acquisition, at which point I joined a startup that grew to one of the biggest private technology companies in America. Both companies looked more like this:

I just can’t understate how significant this opportunity was to develop my abilities by growing with this company and their leadership:

I understand there are risks joining a startup, some of which are beyond the scope of this post, however here are a few important points to note:

  • You don’t have to be a cofounder. The startup you are joining may already be very experienced through prior ventures or have already been operational for a few years. There is a lot to gain from their experience to date. Personally I would recommend most graduates take this “join early” approach rather than “start your own thing”
  • It’s not the size of the company, it’s the growth potential. Can this company grow 10x or more in 3-5 years? Some unicorn startups may still have this potential ahead of them and therefore remain great opportunities as long as you can feel close to leadership today
  • It’s okay to move around. Not all startups will be a success and therefore won’t qualify for the assumed 10x growth. It’s up to you to identify an opportunity you believe has this potential, and otherwise move on or keep looking. If the company growth stagnates, so does your growth. So, do you believe in the vision of the business and do you align with the CEO? These are the questions to ask.

And these are the main points I hear from graduates who choose the established path like Google, Facebook, or Atlassian today:

“It’s a great addition to my resume”

What is your resume for? Maybe your answer is to advance your career and position you for great opportunities in future? My question is why are you focusing on your resume, instead of focusing on your own self-development? The resume is a reflection of you, not the other way around. Put yourself out there and start working your own growth.

“I will learn from established companies”

Here’s the thing… Established companies have learned to do “X”, but only those who went on that journey of learning understand why to do “X”. New hires that enter established companies are shown what to do but not why to do it, and you will take these actions for granted until you put yourself in a position that requires you to understand why “X” is necessary. The learning curve that leads to the conclusion is far more important than the conclusion itself.

“I’m not ready to join a startup”

In addition to the comments above, you need to have confidence in your own ability to grow. If your intent is to do a very specific role and master it before moving on, then perhaps startups aren’t the right opportunity for you. Personally, I would bias towards breadth of experience than mastery early in your career, as startup growth will present the opportunity to understand your strengths and weaknesses far more vividly than slotting yourself into an assumed position. 

“I will excel in any company”

If you are growing faster than the company then you are better than your peers. Go elsewhere! Find peers who stretch you and who you can learn from. I return to the property boom analogy: Sure, some millennials have done an exceptional job clawing their way onto the property ladder in the 2010s… Imagine how well they would have done in the 1980s!

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