We live in a wild time where paths in front of young people have never represented more opportunity or more peril.
The internet provides nearly infinite free knowledge to learn how to create or do anything. The internet also provides nearly infinite cheap dopamine to waste your time, ruin your motivation, and become cynical.
Similarly: those who are able to leverage this new breed of AI tools are having faster career advancement than ever before and those who are looking for "old style" entry level jobs are struggling.
The question is: how do you allocate your most valuable asset—time—when the range of outcomes has never been wider?
With age comes the realization that everything of enduring value compounds – relationships (i.e. network), skills, brand. The notion of compounding that we tend to associate with financial investing is broadly applicable to careers – and life.
Which path will you choose?
Here are 5 mental models to adopt and 5 traps to avoid – compiled as I think about my early career, the landscape today, and the early career folks we want to hire at Multiplier.
Part 2
(1) View your time as an investment
Investing is all about trajectory—the direction of travel. By the time a result is known, investors speak of that expected outcome being "baked into" the price of the asset in question.
Markets are forward looking.
As a free agent in the economy, you want to be forward looking too. Where will the opportunity be in the future?
Every job that you do — as an employee, founder, student, or volunteer — can create the following sorts of returns:
Cash (salary, equity)
Network (relationships that compound)
Expertise (skills, capabilities)
Brand halo (credibility, reputation)
Your goal is not just a good financial outcome but to build relationships that are durably meaningful throughout your life and career. You also want to become qualified for the best jobs that will exist in 5, 10, 20 years— when you'll be entering your peak earning period.
Part 3
(2) Luck is a surface area
I had been working part-time since I was 14 (at a computer store) and writing software that I shared online even earlier. My first full time job came to me in an unexpected way but as a result of my earlier skill investments.
I was positioned to get lucky.
In the second half of my college experience I signed up for a class called "Scientific Computation" offered in the Reed Physics department by a legendary professor: Richard Crandall.
Richard was a true polymath—a Reed alumnus himself, he went on to study under Richard Feynman at MIT and then published papers in areas as diverse as elliptic cryptography, epidemiology, calculating more digits of π than anyone else, quantum, chemistry—and he ran an industry research lab at Apple (the ACG).
Richard did things his own way. The first day of class he walks in, announces that there has been an emergency hiring situation, points at me and my friend Devin and says: "You two have new jobs. Class is dismissed."
I graduated into the recession in 2009 but landed a full time job that quickly led to career and financial growth. Being curious as a kid and wanting to teach myself to code—and then later doing optional homework for a professor who didn't believe in grades—led to my first job in tech.
You make luck by showing up and doing the work even when nobody's forcing you.
Expand your surface area of luck
Perhaps the single biggest factor in early career success is increasing your surface area of luck by meeting great people, being kind, working hard, building genuine connections, and jumping at opportunities.
Luck isn't a trait; it's the measure of the set of opportunities that can plausibly be reached by you. Output, skill, and kindness don't guarantee a specific outcome—they increase the size of the region where good randomness makes contact.
Part 4
(3) Catch the wave early
I know a lot of people who did exceptionally well by getting into mobile development or data analytics in 2008 or 2009—right at the dawn of that era. There was a strong tailwind that meant decent skill in that domain would accrete to job opportunities or business success.
Being early pays off more than being late.
Being early pays off more than being late
My first company, Lucky Sort, was not actually that successful a business—but building a data oriented company meant that we almost accidentally created skills and IP that made us a desirable target for Twitter to acquire in 2013.
Selling a business early in my career set me up for a sort of "preferential attachment chain of wins" where early success helped make later success more likely.
It's not just engineering roles that can benefit—being in tech has been the place to get lucky. I knew two guys who were liberal arts majors without technical skills—but they joined Instagram pre-Facebook acquisition and I suspect it worked out quite well for them.
This story isn't unique—I met a ton of non-engineers who hit it big in Silicon Valley at places like Twitter or Stripe by getting into BizOps, Sales, Business Development, or Customer Service roles.
This is perhaps an exceptionally lucky draw—but you make luck by going to where the action is and just trying your best to create value for other people with the skills that you have.
One of the central tenets of investing is that there is no reward without risk—these dynamics are irrevocably tied together. Investor Alex Rampell frames this as: "Have you made a thing, or sold a thing, or done a thing—not been Oompa Loompa #12,411 at giant company."
“My advice to students is to chase the biggest and most prestigious logo early in your career...”
Alex Rampell responds that this is now counterproductively wrong in tech:
if you want to make it at a startup, boosting your resume with the biggest
logos can actually hurt you.
When you join a business that is already too successful, the part you play in making it more successful is limited. The people who select for the most high-growth roles want to find folks who will take risk.
By the time success is clear, it's too late—the results are priced in from both a financial and reputation return basis.
Software engineers - and by extension other employees at companies that produce software - tend to be treated very well because each employee has such a large potential for positive economic impact to the business. This is technology leverage.
The story is similar for those who work in finance - they generally use financial leverage instead of technological leverage. My hedge fund friends are pretty well cared for.
The broad point I make here is that anywhere you find people who are able to magnify their impact on the economy through some form of leverage you'll find free bananas (and more!)
The AI platform shift provides a once in a lifetime opportunity to transform professional services firms with technology in a way that benefits clients, staff, and owners. This can deliver a lot more than free bananas for all of us (though, I'm not opposed to sponsoring a fruit bowl).
The tech industry didn't become the pampered employee promised land overnight - in the late 1990s and early 2000s it was still largely a collection of felt-cube-wall offices like those profiled in the 1999 movie Office Space. As the winners in the tech industry produced ever more cash flow - and investors caught on to the power law dynamics behind these returns - they ignited a bidding war for talent which lifted all the boats in that ecosystem.
The road ahead won't be easy (or, as my old boss used to evocatively say, an "escalator ride to success") - but I'm confident we can, through focus and technology leverage, deliver better outcomes for ever larger numbers of clients. Then, as a result we will justify ever greater compensation and better work environments for our teams.
Part 5
(4) Work at the edge of your ability
Work should be at the edge of your capability—always pushing you to grow.
One of the most pure applications of the "Edge of ability" principle is the training regime of a body builder—lifting weight and volume just up to the point of failure is how you grow. This approach must be measured, though—too little and no benefit is gained, too much and the risk of injury spikes.
Generalizing this to work:
Too challenging → Anxiety, Failure
Not challenging enough → Boredom, Apathy
Right level → Flow state
One common theme of all of the most successful people I've learned from is that they spent a large amount of time at the outer edge of their ability—constantly leveling up.
In that first job I took out of college I was quickly learning how to build and ship machine learning systems (something I was quite unqualified to do)—then shortly thereafter I was hiring a team and managing them (I was also not qualified for that). The more I did outside my competency, the more I was able to learn.
The honest self-assessment questions:
Can I do things now that I couldn't do 6 months ago?
Do I see challenges ahead of me that feel daunting?
Is this work challenging or just time-intensive? Some problems just require hours to solve vs. problems that require me to grow.
When you are young with the ability to take risks, there may be asymmetric upside in pushing slightly further out than you think you can handle.
Part 6
(5) Focus on genuine relationships
Almost all the best jobs I've gotten, people I've hired, funding rounds I've raised, advice I've received—they all have one thing in common: they're the product of a genuine relationship that I built.
Deep relationships where you a) care about and respect the other person and b) have significant experience working together are the foundation of these sort of connections.
To get the upside of these genuine relationships you have to be emotionally available at work—truly expressing how you feel (while staying professional) and thoughtfully listening to others. This essential human connection creates trust and understanding.
This advice seems almost trivially obvious to me—but when I look around it actually seems shockingly uncommon.
Failure modes here include: creating many superficial relationships where nobody can really vouch for the quality of your work or your integrity. Being transactional or disinterested in other people or, worse, burning other people. Playing political games. Being cold and disconnected—communicating the minimal required for the job.
Business karma is real—if you help out the other people around you and build genuine relationships these will compound like nothing else.
The returns are both practical (access to opportunities) and far deeper.
The essence of human thriving is having a community of people that you care about—and who care about you. Your career can be an ideal domain within which to build one such community.
Part 7
Five Traps Nobody Expects
(A) Great financial outcome without the network, career trajectory, or internal scorecard wins will feel empty
A lot of ambitious young people are concerned with financial outcomes - or career trajectory (often a proxy for future financial outcomes), or what is currently fashionable (often a proxy of where the good returns have already been gotten).
The story you'll tell yourself (or your kids) matters more than you think now. Focus on creating real value, durable relationships, and a track record you'll be proud of.
External validation (manager praise, promotions) is nice but insufficient.
(B) Big brands can make it hard to grow yourself because you have so many people scrambling for opportunities. Understaffed teams give you an opportunity to shine.
The more established a firm is the more great people want to work there. The more great people work there the more competition there is for meaningful work and opportunities.
This idea rhymes with the idea of "Table Selection" - as a poker player your ability to win will be determined as much by who the other players at your table are as by what you can do.
The ideal situation is to be in a small, understaffed, team of exceptional people. This will give you great network, chances to learn, and a shot at doing work you're not yet qualified for (operating at the edge of ability).
(C) By the time success is clear, it's too late — the results are priced in from both a financial and reputation return basis.
Everyone wants to buy a stock after it's clearly a winner, join a company after the risk looks low. Fundamentally being able to absorb a certain level of risk and uncertainty will be required to get the full amount of upside.
(D) The cohort effect — The cohort of people you bond with will matter more than you think.
If you're early in your career you'll think of your peers as junior today—but in 5 or 10 years many will have climbed high and the history you have with them will matter.
Focus on building real relationships with people who are more senior than you, peers, and more junior than you. Be kinder than you need to be. Great people are rare. Great people where you also have a genuine personal connection are priceless.
(E) Financial success matters less than you think — After you win the financial games you'll just want to go on a business adventure with your friends. So focus on the friends.
I was very focused on financial independence when I was younger. Every vesting day - every bonus - I would diligently track the spreadsheet. The truth is that the opportunity you can easily measure (usually finite, near term, low risk) is wildly inferior to the opportunity you can't easily measure (usually uncapped, longer duration, higher uncertainty).
Part 8
The early career playbook
Early on you have maximum natural energy with minimal life responsibilities. Highest capacity to take intelligent risks. Ability to fully focus on growth without competing priorities.
Just like investors view companies: your best years are 20+ years down the line, but it's hard to appreciate long-term compounding in the moment. In a compounding process the good returns come in the second-half of the process.
Financial success is a downstream output: Focus on maximizing learning and network, and skills first.
Financial outcomes follow from capability building and positioning yourself to get lucky.
The goal isn't to be reckless, but to be intentional about growth and willing to push beyond your comfort zone when the opportunity is right.
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