Startups seem to have a very different societal perception these days.
I’m not sure if it’s Gen Z leading the entrepreneurial charge or people looking for
new opportunities during record high inflation — **but working at a more agile and fast-paced
startup seems to be in right now.
I mean what’s not to like?** You learn more because you take on more responsibilities,
you probably report directly to chief level executives, and you get a lot of those valuable
early-stage stocks in the company.
If you’re new to this channel, since graduating MIT and dropping out of Stanford, I have exclusively
worked with startups.
I’ve been a founder, and have held multiple positions from Software Engineer and Technical
Product Manager to Chief of Staff and even interim CEO.
I’ve been behind the scenes coding and I’ve also been in the forefront: doing interviews,
pitching, and demoing products.
**I love startups, and honestly, I don’t see a scenario where I will be completely
disconnected from the startup world.** However, it’s not all rainbows and butterflies.
It all starts with the people.
People are everything in a startup.
These are the people that you’re going to be spending extra hours working really hard
with.
They’re the foundation, and those individuals and relationships will be what keep the startup
going through the inevitable tough times.
**During my startup journey, I’ve met some incredible people.** This includes investors
that are just genuinely really cool, coworkers who I now consider some of my closest friends,
and industry leaders who I aspire to be.
But, working this closely with people in a high pressure environment is also bound to
create tension.
**The earlier the startup is in its development, the less likely there is to be any sort of
hierarchical structure.** Everyone is more or less the best at what they specifically
do.
Therefore, when bigger decisions come along, it may feel like a too many cooks in a kitchen
scenario where things stall when there are major disagreements.
Usually, in a bigger company, the CEO and senior directors can dictate the direction
that they want the company to go in.
**However, at earlier stages, employees and founders alike feel more empowered to push
their agendas forward.** I can’t speak too much about the people drama I’ve experienced,
but all I can say is that those moments get very stressful.
It feels like watching loved ones fight one another.
Although I knew that the pressures of a startup could lead to people tension, I never truly
understood the extent of it until I lived it.
**One of the great things of joining an early stage startup is that you will probably get
a substantial chunk of equity — or at least you should if you’re an early stage employee.**
The founders aren’t the only ones who get equity.
If the company has good leaders, all early hires should receive significant amounts of
equity where if you successfully exit, you’ll make at least a couple hundreds of thousands,
if not millions.
That equity should grow at an exponential rate with each round of funding.
However, the odds aren’t in your favor at that early stage.
**Most of the time, initial employee equity becomes worthless because the startup ends
up failing.** I love startups, and highly recommend them for personal growth.
However, for financial stability, I’d actually recommend maintaining a diverse portfolio
regardless of your involvement in startups, since you never really know what’s going
to happen with the market.
**It’s great to hope and strive to have a successful exit, because why would you be
in the start up to begin with if you didn’t believe in it?** But you can’t bank on the
money that you may receive if the startup were to exit with a valuation of X dollars.
The odds are simply not in your favor.
If you’ve been paying attention to the markets, you’ll know that right now traditional forms
of investments like stocks and even crypto aren’t doing so hot.
Unforeseen events like Covid and historically high inflation make timing markets almost
impossible.
**However, with a diverse portfolio, you have a chance of having your other investments
makeup for some of the other losses.**
An alternative asset class that historically has done well during inflation is art.
**This brings me to Masterworks.
Masterworks is the platform for investing in contemporary, blue-chip art.** You’ve
probably heard about billionaires investing in art, but thought that it’s simply an
unattainable investment.
Until Masterworks came along, you were right with that assumption.
Investments in art by world-renowned artists like Picasso, Banksy, and Monet were accessible
only to the ultra rich.
Masterworks has sold three paintings since 2017, each returning over 30% net IRR, or
internal rate of return, to investors.
The S&P 500 is viewed as the benchmark for growing your money, and contemporary art prices
have outperformed the S&P 500 total return by 164% for the past 26 years.
**Although we can’t predict the future, similar works have appreciated 17% annually
since 1984, just to put things into context.** How Masterworks works is that you create your
account with your traditional bank account and pick major works of art, or their new
blue-chip diversified portfolio to invest in.
Then you choose how much you’re trying to invest, hold shares in those works, and you
even have the option to trade them in Masterworks’ secondary marketplace.
**There’s currently a waitlist to sign up but with my code you can skip the waitlist
and start investing today!** Huge shoutout to Masterworks for sponsoring this portion
of the video.
Startups are truly a pressure cooker for your emotions.
Things never seem guaranteed in the earlier stages.
The company will always be focused on fundraising, and until you get into your later rounds of
funding or reach product-market fit, surviving is the biggest goal.
Startups aren’t for everyone, and a lot of why they aren’t for everyone is the emotional
roller coaster involved with them.
The highs are really high.
You may have finished a successful demo, iterated another time on the product, or closed a round
of funding.
**When these things happen, you feel euphoric and invincible.** But the lows also do get
very low.
You may have had to let someone on the team go, the demo may have gotten delayed due to
unforeseen bugs, or the company’s runway begins to get shorter and shorter.
**When these things happen, you start to really question your bigger life decisions, and you
feel as if you need to have fallback plans.**
In a startup, you’re almost always on call.
It’s not really the long hours that I'm referring to, because some really long days
are expected.
I’m referring to the weekends where you may have to fix a bug to keep the servers
running or you may have to do a last minute edit to the pitch deck for a Monday pitch
that you have to stay on top of.
If you’re working with a novel idea, then you also don’t have the safety net of examples
that you can base your work off of.
**You can’t simply look up a tutorial.** Of course, you’ll probably be able to piece
together various solutions to create your product, but this involves innovating on your
approach.
This may require days or weeks at a time where you’re trying to tackle this one critical
problem.
This is where a lot of the growth comes from, but it’s also a very vulnerable place to
be in.
You’re being relied upon, and the solution has to come from your brain one way or another
**To get you through the emotional roller coaster that is joining a startup, I’d say
to expect adversity.** I’m usually a very optimistic person by nature, but there’s
been many times where I’ve had to lower my own expectations in order to keep moving
forward.
Timelines are always longer than expected, that MVP always takes much longer to iron
out bugs, and many iterations are required before you nail the actual product that hits
the market.
And actually getting that product-market fit will require getting people to buy in, whether
by working with you or investing Not everyone has the entire vision thought out like you
do, so it’s really hard to get really good people to commit at an early stage.
If you do, it does, however, prove that you have a pretty good idea.
Throughout your career in startups, you’re going to have to learn how to communicate
with people who don’t have tech backgrounds.
The earlier the startup is, the less managers are around to bridge the information between
the technical and non-technical teams.
It’s not going to be as simple as saying you’re using the latest and greatest technologies.
You’re going to have to answer a lot about “why this is important, and why do we need
this right now?”.
This goes for explaining your ideas to leadership directly if you’re not a founder, or pitching
these ideas to investors if you are.
You need to get good at framing that story.
If you don’t have much experience, it doesn’t matter how early you were involved with the
company, there’s probably going to be new people hired above you to fill the needs of
the company.
You can’t take these things personally.
You’re going to learn a ridiculous amount and probably fully take on multiple roles
during your career.
In startup software jobs, you’ll have so much more knowledge about systems because
you would have had a hand in many more parts of the system than you otherwise would’ve
at a larger company.
You have the responsibility of understanding how everything works from the ground up, and
not just your little section of a giant system.
As you gain more of these valuable experiences, you will be that person that can lead larger
teams or even whole companies in the future.
**An aspect of working with startups that I think is overlooked is the fact that you’ll
probably work directly with chief level officers both inside and outside of your company.**
These experiences allow you to realize that these leaders are very normal people.
They may be very smart and ambitious, but they’re not the all-powerful, never-faltering
leaders that you may have expected.
They’re human just like you, they have hobbies that they love outside of work, and they are
learning with each experience as well.
To me, this gave me a huge change of perspective.
I now look at various leaders in their fields in a new light.
I’m no longer intimidated by the presence of anybody, and it’s given me the confidence
to enter any room knowing that I also have some pretty unique experiences under my belt.
One of the biggest blessings and curses that you’ll experience at a startup is being
needed and respected by the team.
If you got hired or recruited to be a part of a rapidly growing team, you showed enough
to not only be valued, but needed.
This is a feeling that’s hard to replicate in other work environments.
Most of the time there’s enough employees and enough people in the pipeline that you’re
expendable.
In a tech startup, as a tech employee who is building core technology, you’re probably
not.
You’ll be relied upon to produce great work, which does add to the pressure of working
at an early stage company.
However, from my experience, feeling needed has empowered and motivated me to push myself
harder than I would’ve otherwise.
And I truly believe that my career has greatly accelerated because of this.
**So yeah, there’s a lot of things to consider before joining an early stage startup.** But
hopefully you now have a fresh perspective on things and can make a more informed decision
in the future.
I’m going to continue to make the biggest difference I can on this world, and hopefully
all of you will follow along that journey with me.