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The Career Path I Didn’t Consider, But Should Have (themuse.com)
96 points by jseliger on Jan 11, 2015 | hide | past | favorite | 116 comments


The author sells equity as a main motivator in joining a startup. But if you believe in equity, you are far better off being a founder than an early employee

Being the first employee (or an early employee) of a startup seems to be the worst possible choice.

* none of the stability of a larger company * a salary which is likely less than market * 10 to 100 times less equity than a founder (So, in an exit, you'll make 10 to 100 times less money! Not all startups have billion+ dollar exits.) * a huge amount of responsibility - might not be as much as a founder, but still comparable * less influence and decision making ability than a founder * less insight into the finances of the business than a founder (without that insight, how will you know if that equity is worth anything?)

The only benefit I see of being an early employee is if the founder is a seasoned veteran who has already done this who you can learn from and be mentored by. But the vast majority of ycombinator founders seem to be new to the startup game.


To add to your list: as an early employee, there is a good chance that your equity will get diluted a bit. The small fraction of the company you "own" when you join (and after your options fully vest) might shrink significantly after future funding rounds. As an employee you have little leverage against getting diluted.

The worst statistic of all: the vast majority of employees never exercise their stock options. According to this article, less than 5% of employee stock options are ever exercised: https://medium.com/@henrysward/broken-cap-tables-bbf84574a76... Start-ups would love for you to take a lower than market rate salary in exchange for options as the risk is entirely leveraged to the employee.

If you are going to work for a start-up you should never count your options as payment in lieu of salary. They are a lottery ticket and they are no substitute for cold hard cash. There are various other good reasons one might have for joining a start-up, but options should not be one of those reasons.


During my last job search, I was contacted by several companies with seed funding (not even series A). They wanted to lowball a salary and then give 1% or less equity to "make up for it".

Hahahahahahaha. Haha. Ha. Are you serious? For an early non-founder employee, startups might as well be scams.


How does on balance the lower salary with the increased equity in making a decision?


Pretend the company is valued at $1m. Pretend you consider a standard programmer's salary to be $100k. If they offer you a $75k salaray, you are saving them $25k/year. Assuming you'd be there for 4 years (because that's how often most vesting periods are), you are saving them $100k. $100k of the company's $1m comes from your substandard salary. So you should get $100k in equity. That's 10%.

If they try to convince you that you don't deserve that much because the value of the company will rise in the future, ask them where the signed term sheets for the next round are.


A company today is worth however many billions it will be worth if it succeeds, discounted by the risk that it won't succeed. That's an incredibly difficult calculation to make, but fortunately you don't have to do it if the company recently had a funding round, just use the value the other investors decided on.

So if the company raised money at $10MM and you're being offered 0.5% equity, then treat it as a $50,000 bonus that you get for being a loyal employee over the vesting period.


You are speaking in some really large generalities. Being an early employee of a startup isn't indentured servitude.

If you are offered little equity as compared to the founders, don't join. If the founders won't share the financials of the company with you, don't join. If they wont pay you the salary you want, don't join. If they wont offer you the opportunity to grow into the role you want, don't join.

And you can't argue that every company is like this, because once upon a time I was employee #1 of an early stage startup and your post doesn't align with my experiences at all.

I'm not taking anything away from founding a company, I think in many cases that is a great idea. But being an early employee isn't such a horrible deal if you are selective in what jobs you take.


If there's a market for lemons, you'll get two types of people: people who realize it's a market for lemons and stay clear of it—and people who don't realize this, and end up exploited by the market.

Tu quoque: "If you find out the car has water damage, don't buy it. If you find out the car was in an accident, don't buy it. If you find out the car was stolen, don't buy it."

Nobody wants to buy such cars; people are effectively tricked into buying such cars by the information assymetry inherent in the market. This is why there are lemon laws.

And just because there are good used cars for sale, doesn't mean it isn't a market for lemons. The good cars (and jobs) sell and sell quickly, while the bad cars (and jobs) stay on the market—so the market becomes saturated with bad cars/jobs, and the actual good cars/jobs become so rare that people invest more in pursuing them than they're worth, creating a sort of dollar-auction market failure.


Sorry for the OT.

> The good cars (and jobs) sell and sell quickly, while the bad cars (and jobs) stay on the market—so the market becomes saturated with bad cars/jobs, and the actual good cars/jobs become so rare that people invest more in pursuing them than they're worth, creating a sort of dollar-auction market failure.

This, at least in my experience, is exactly what happens with musicians seeking bands.


You can bet that for bands seeking musicians it look exactly alike.

The market for especialized labor is full of lemons on both directions. Yet, we don't get any coordinated action to increase transparency.


> If you are offered little equity as compared to the founders, don't join. If the founders won't share the financials of the company with you, don't join. If they wont pay you the salary you want, don't join. If they wont offer you the opportunity to grow into the role you want, don't join.

Lots of people don't join startups because of these reasons - which is exactly why she wrote this piece, in an effort to convince more people to consider startups.


> If you are offered little equity as compared to the founders, don't join.

There is no "if". Employee equity is always a small fraction of founders'. This won't change until people realize the discrepancy, or demand more equity at early stage startups.


I agree with you about equity, and I'd go one step further - if you're inclined to work for a startup, you're better off in almost every way being a founder rather than an early employee.

For instance, one thing people mention here is "experience" - that you gain experience working for a startup that you wouldn't get at a big company. You only might.

Ask yourself: Are you pitching investors and making contacts? Are you meeting with the lawyers to nail down legal issues? Are you negotiating office space? Setting up equity arrangements and deals? Managing PR? Getting users? Or are you mainly just handling technical issues, while those tasks are kept from you. I know a lot of managers like to say they handle the business side so that engineers can focus on the important stuff, but keep in mind, when the storm hits, you may find, as you stand in the rain and 70mph winds without roof or even an umbrella, that all you were really protected from seeing was the forecast.

I've worked at a couple of startups, and they really didn't expose me to much about running a business. They did expose me to new and interesting technical challenges, and to that extent, I did get something out of it, but certainly nothing more than I would have gotten out of working for a big name company like Google or Facebook.

Really, if your big goal is to learn how to start a startup, I doubt you'll get that by working for one as an employee, even an early one. If you want to prepare for your second startup, I doubt there's better preparation than starting your first one.


Having been both a founder and an early employee, I wholeheartedly agree with this. Early employees really do wind up working nearly as hard as founders and the payoff is extremely disproportionate. The most likely scenario by far is failure, so your equity will be worth nothing. Your next-best hope is a moderately-successful exit, where the investors get their money back, the founders get enough to have made the endeavor worth their time and the early employees walk away with a few thousand. Hardly a year-end bonus at a bigger company (which you can expect _not_ to get at a startup). The Facebooks and Twitters of the world, where many/most early employees become millionaires are few and far enough in between to be essentially lottery tickets.

However, if you are totally fresh and want to gain some experience, it can be worth your time. The market for developers right now is such that you may not need to take such a pay cut vs a bigger company. This is the real variable. What are you giving up. And while you may work about as hard as a founder, you aren't as likely to wind up ruining your credit and destroying relationships with family and friends due to the incredible stress.

So it may be worth it for the experience. Just don't get sold on being an early employee as a path to riches via your equity. That path is vanishingly rare.


Having the opportunity to take on a larger role earlier in a company's lifespan has a lot of allure to me - you get a lot of valuable experience that a larger company would be loathe to offer to not as experienced employees. For an example, I am a senior/lead software engineer with only about 2 years of professional experience. However, my experience has been increasingly high quality, and allows me to move up at my speed, which could pay off in the future if I decide to join a larger company or if I want to start a company of my own, having some credibility with other professionals I work with or network with.

In addition, it gives me the opportunity to affect the culture of a company and help the environment be run the way I want it to be. There is a lot of work to be done, but it's the same in any non-big company.

The stability isn't as much of an issue to someone like me, since I have plenty of contacts I can reach out to if I don't like the looks of things - I've gotten in person interviews set up as short as a few hours. The salary isn't as much of an issue when I am investing in myself and preparing for a larger salary down the line due to outsized responsibilities. The equity may not be as much, but it doesn't need to be founder level to be good enough, and also there are other concerns for a founder - increased dilution and the incredible early stress fundraising & networking is not something I necessarily might want right now.

Not everyone necessarily has the skills to be a successful founder (or co-founder) - personally, I may choose to found my own company down the line, but it will be in what I want. In the meantime, working as an early employee is ok to me.


"a senior/lead software engineer with only about 2 years of professional experience"

Has the term senior lost all meaning?


Has the term "CEO" lost all meaning, amid the hundreds of startup founders who have no management experience? Not at all. They're called CEOs because they make top-tier executive decisions and act as the public face of their startups.

Based on the post above, Bahamut's senior title is also a function of the responsibilities he's dealing with - in this case, building the first viable product of the company at an architectural level, and overseeing the completion of major features from start to finish. Just like the crop of startup CEOs in YC, his title has nothing to do with his previous experience. If the leadership of the company has decided he's fit to train new engineers and prioritize tasks for them, the "lead" description is apt too.

I'm sure there are much more skilled CEOs and much more skilled lead developers at other companies, but it's completely impractical to compare people based on internal titles. We're talking about descriptions of an employee's role in the context of his or her own company - don't read anything more into titles than that.


For 20 years I've only ever called myself "software developer", or "QA analyst," or whatever the role was. I've never added level of seniority, and I always used my own term, not whatever corporate label a particular HR department dropped on a role. ("Technical staff member?" Please.) I really don't care how my employer of the moment labels me.


My job title has often been "nerd".


Absolutely! If you framed your diploma, hung it on the wall, started work the day after graduation, and made "Senior" before you have to dust the frame the first time...


The terms CEO/CTO/etc. haven't lost their meaning with all of the startups out there (some pretty poor), why would years of experience necessarily dictate that a quality engineer cannot reach that position so quickly?

In my case, I continually hone my craft outside of work (with some breaks here and there) - I spend a lot of time learning, digesting new patterns, and assessing then. I read articles, and spin up many projects to experiment hands on with the technology, patterns, etc. My abstract depth was already sharpened from my time as a math PhD student (ultimately dropped out), and spending 2 1/2 years unemployed from having trouble finding work whetted my appetite for working to an insatiable degree. The Marine Corps enhanced my innate leadership traits, which I then took the lessons learned and applied them to leading a team (which I had to do as an acting tech lead when the tech lead had to take leave due to a family death), as well as generally carrying myself.

I earned the senior title through domain expertise at an exceptional level, and with a bit of luck achieving it in a piece of tech that exploded in popularity just afterwards (AngularJS). I have been seriously recruited as a lead developer for about a year, although I have turned down such positions for a while since I did not consider myself ready at the time.

The one thing I appreciate about being in the Bay area is that companies here recognize that such talent can exist, and such people may not even be unique. In most of the country, I probably would be still a mid-level developer, and not given the opportunity to demonstrate I would be a capable senior developer, much less lead developer.


And that's why you should ask for a good salary (the VCs will most likely pay for it)

And it's definitely not a bad experience (of course it's fast paced)


http://genius.com/Sam-altman-lecture-1-how-to-start-a-startu...

cmd-f: "You'll make more money and have more impact"


>> "But if you believe in equity, you are far better off being a founder than an early employee"

But not everyone is cut out to be a found or has a good idea they can execute on. For those people being an early employee is the best they can do. It's also incredibly more stressful being a founder and a lot of people don't want that. They are happy to take a lower than market salary in exchange for lottery ticket (equity).


Employee #1 is taking on 80% of the risk of a founder for usually a sliver of the upside. I know a lot of single-digit startup employees and I really think you're doing them a disservice by characterizing that role as really at all less stressful than being a founder.

You see founders parachute straight into consulting or speaking after flaming out of their tech startup. Their team needs to go get jobs.


>>Their team needs to go get jobs.

I can't speak for everywhere on earth but in this current Bay Area tech job market, I can just as easily parachute into a well-paying, full-time gig at $TRENDY_TECH_COMPANY. You build interesting experience & insight being the first-hire and, if you're actually a skilled engineer, shouldn't have a problem finding your next job in about 4 to 6 weeks if things don't work out.


Sure. But the amount of risk you're taking on, relative to the reward, is much, much, much higher.

Management consultants make a lot more than code jockeys do.


It's still stressful but nowhere near as stressful. For instance - employees get a salary, founders usually don't. That alone makes a huge difference. The founder has to keep the startup alive, try to find funding, direct the product all while one bad decision could kill it. The employee has to do what the founder asks, do it well, and go home at the end of the day. Being an early employee is still more stressful than a normal job especially as there is no one to help out if you're stuck, but I think the difference between founder and early employee stress is vast.


Not to mention not everyone has 6-18 months of expenses saved up to live off of while they try their start-up, not to mention capital to start the business.

I'd go off and found a startup tomorrow if I had some way to keep paying my mortgage and feeding three mouths for however many years it took to adequeately replace my current income.


Also, you are unlikely to survive the hard work of a startup if you are not there for intangible reasons. My rule of thumb is that I will join if I believe in the vision and want to work with the team in the culture we would create together. If that is not there it is much better to get a big-co name on your resume or consult if you have strongly marketable skills.


Sightly less than market salary is a lot better than 12+ months of no salary, and putting a good chunk of your saving in to getting a company started.

If you want a ton of equity, start a company, but don't expect a paycheque. If you want a paycheque and a lot of equity, join an early stage company.


By the time a company can afford decent pay checks for new employees, those employees probably aren't getting "a lot of equity."

Yeah, they'll get some, but they won't exactly be retiring after the IPO because of it.


As always, when someone has something to gain from giving you advice, be skeptical, even if it seems well intentioned.

It is fairly disingenuous of VCs and other investors to advocate for talented young people to start businesses without providing data on how most startup founders (and especially employees) do. From the limited amount of data on this I've seen, it looks like your odds of making any substantial amount of money is quite small and certainly if you're talented enough to found a successful startup you're probably talented enough to get a higher paying job at a more stable company. It might not be as glamorous, but it will give you time to focus on the things that are more important to you than money.


There are millions of people in the US alone that would jump at the chance of taking a good startup job or creating a startup themselves. They don't need convincing. But startups don't want to hire them and investors don't want to fund them. Because they're poor, under-educated, and different. They also make up the majority of the smart and talented people.

It would require actual effort and understanding to work with those kinds of people. A lot more work upfront. Some of them haven't even read Homer, the plebs.

Instead, wealthy investors ignore those millions and spend their time trying to convince a handful of wealthy entitled children to temporarily forgo the easy life at Google or Accenture.


If there are "millions of people" smart and talented enough to start a successful startup, or join one early, this sounds like a spectacular business opportunity.

After all, everyone knows doing a startup is easy and riskless if you just have enough smarts and talent. Startups don't require any skill or effort beyond that. We therefore conclude that the reason there aren't millions of people involved in startups is a conspiracy of "wealthy entitled children" who hate anyone who hasn't read Homer. I remember all the in-depth quizzing I got about Homer last time I applied to a wealthy entitled child's startup.


The most successful Silicon Valley founders and investors were born into wealth, attended expensive private schools, and are connected by exclusive networks. We therefore conclude that these kind of people are simply better and more successful human beings than others. Why else would this tiny class of people so dominant an entire industry?


Startups are hard and risky, which is precisely why it's dominated by "wealthy entitled children". If a poor kid's startup fails, poor kid gets kicked out of his house and starves. If a wealthy kid's startup fails, wealthy kid doesn't get to buy his Ferrari for another year.

I have no idea how to break this vicious cycle, apart from strengthening social safety nets for the lower classes to minimize downside risk. But we know once you start providing welfare for the poor, they'll simply stop working, right?


Kickstarter and crowdfunding are a great next step. When it's not just rich old guys picking which projects get funded you get Oculus and an entire new VR industry, created by a unpedigreed outsider that no investor would have given the time of day to.

The real shift will come when crowdfunding for equity is possible. When not just rich investors will be able to benefit from the massive wealth creation of technology companies. It may be that regular people are willing and able to fund as many viable projects as exist.


Exactly: People talk about how Bill Gates dropped out of college to make a startup, but many gloss over his socioeconomic starting-point that let him "afford the risk".


I'm confused. Where was it ever implied by the parent that running a startup is "easy and riskless if you just have enough smarts and talent" and that "Startups don't require any skill or effort"?

The point, that I understood, from the parent is that the job (SV?) culture is highly homogenized and that there isn't enough outreach to skilled people who don't "fit". Did I misunderstand? If I didn't, do you not believe there's any amount of truth to this?


[deleted]


"Yes, the homogenized group of Americans, Europeans, Indians, Chinese, other Asian and Middle Easterners present in the valley clearly won't engage in outreach to skilled people. Another popular meme: those greedy capitalists are constantly lobbying congress to give them permission to reach out to skilled people from around the world in order to lower wages. Better stop them, it's bad for workers!" -yummyfajitas

It's pretty clear to me that staunch isn't talking about racial homogeneity:

https://news.ycombinator.com/item?id=8871859


I am searching for a business partner for eCommerce that would do the whole business part while I will be plugging in and extending automated sales technology I created and use in my other companies, with 50/50 equity split and the initial operating capital provided by me if necessary. However, almost nobody wants to start from scratch, growing the company as their baby (despite having the benefit of immediate use of my mature technology, spending at most 1 hour a day running the business anywhere in the US and non-interfering from my side on their business style except for advices on proven business model I operate and avoiding legal problems); they expect earning $100k within the first 3 months or so with no work at all. Sometimes I feel like there is an insurmountable obstacle between their dreams and effort they put into the work to get where they want to be...


Surprised you're having issues filling this. I come from a Supply Chain and Ecommerce background. Currently VP Product for an ad tech company. Let me know if you'd like to chat. My HackerNews username @ gmail, or on Twitter.


Done this once and happy to do it again. Send me a note: cram@openmailbox.org


Product manager open for opportunities here. totalrobe@gmail.com


I agree that the majority of talent remains untapped, and that's why I believe actions like Sama offering his startup class free online are huge steps in the right direction. While I don't wish to instigate an immigration debate in this thread, I do believe that the goal of equal opportunity regardless of geographical origin is extremely important as well.


Being smart and talented doesn't make a successful business, even if you add hard working too. The actual valuable part of the business is the ability to get others to give you money for what you do. It doesn't matter how that is achieved, but your worth is directly proportional to how successful at that you are.


>They don't need convincing. But startups don't want to hire them and investors don't want to fund them. Because they're poor, under-educated, and different. They also make up the majority of the smart and talented people.

This is a tragedy. Seems like a pairing between early stage startups and fresh grads may be a great thing. Lots of fresh energy from the young to feed a startup and a chance for them to learn and grow.

Some countries provide government funds for startups, maybe we fan have some of this fundijg for startuos that hire the young?


...and our government that there aren't enough of them.


Completely self-serving, where it is coming from, and completely wrong. An early employee at a startup will get fraction-of-a-percent equity (at time of exit, and often, at time of joining). And that overstates the amount of equity. Investors, and increasingly, management, get things like liquidity preferences. You need an exit in the hundreds of millions before that amounts to real money. Employee #5 at Google or Facebook does very well. Otherwise, you make a lot more at established industry. There are a lot of suckers out there who'll take those jobs, so I don't see them getting better.

Where do you learn more? It depends on the startup and the industry. If it's a YC startup with a pair of 21-year-olds at the helm? I'd actually say mainstream industry. Now, if you compare co-founder to call center -- definitely go co-founder, but:

1) Call center is an unusually bad job. 2) The type of person hired by a call center is unlikely to get a startup job, unless the startup sucks at hiring. Seriously.


> There are a few warnings that go along with working for equity.

Another warning: Equity can be expensive. It can cost a lot of money to keep that equity when you leave the startup.

I was at a startup for 2 years and had 2% vested equity. I left the company 2 months ago. If I want to keep my equity, I have to exercise my stock options and pay ~$30k within the next month. If I don't, the equity disappears forever.


There's a third option: you can sell some or all of your equity to an investor. Companies don't like to talk about them, but I've seen more and more of these transactions happening, and they can be great for everyone involved: the employee gets a payday and eliminates her risk, and the investor gets access to a company she would not have otherwise been able to.


Don't rules about sales needing to be approved by the board block such transactions?


If the startup is doing well you'll have no problem finding an angel to finance those options for you.


Plus the tax bill on the difference in value from option issue date to option exercise date.


Definitely worth looking into http://esofund.com/


Is that because the stock hasn't vested?


It's because almost all the time you are actually issued options, not shares. The options allow you to buy a certain number of shares at a lower price, but you need to pay that price to exercise them.


No, it's because options are completely shitty for employees (whereas they're great for the company).


She says:

"There are a lot more startups today, and you can in effect become an early investor in one by going to work for it."

It's important to remember that she means this for one very particular industry, and she is talking about a very particular kind of startup. Overall, there has been a steady decline in the number of startups during the last 30 years:

https://www.fedinprint.org/items/fednsr/707.html

"The first observation is the steady decline in the firm entry rate over the last thirty years, and the second is the gradual shift of employment from younger to older firms over the same period. Both observations hold across industries and geographies."

The great era of starting a new business in the USA was several decades ago. It is much more difficult to do so now, and that is perhaps part of the reason why there are less entrepreneurs now, and less new companies being founded.


Yes, she is talking about one particular kind of company, but Jessica's definition of a startup is the generally agreed upon one here on HN [1]. (The fed is using a definition of a brand new company.)

While the fed paper is really interesting, I don't think it is relevant for this discussion.

My own personal and unsubstantiated view is that we're living in the golden age of startups.

[1] http://www.paulgraham.com/growth.html


And that's assuming your founder is scrupulous and actually gives you the promised equity, and it vests.

No, I'm not bitter, why do you ask?


I thought you were a new user who had no idea where he was right now! :)


(missed edit window.) What I mean is that, just as the OP does (who is in fact a very experienced HN contributor despite this one comment reading as though written by an outsider), we all know the context that is meant here with a specific kind of startup, and don't presume to generalize it.

"The great era of starting a new business in the USA was several decades ago" - except for building the next instagram or airbnb while having $0 in capital and maybe 8 months of coding experience, oh and not even any business experience, perhaps still being a twenty-something who has never done anything. Then "several decades ago" probably wasn't the best time to build the next social startup.

But the above ridiculous constraints are still enough for some of us, people reading this very thread, to succeed at this. Literally. That doesn't mean we presume to extend this to the rest of America's 20 million entrepreneurs and business owners. That's why I said it looked like he was a new user who didn't know where he was for a second :)


> My 20-year-old self didn’t consider joining a startup—or founding one—as a career option, but I hope you will.

I would think that the startup environment, and the job environment in general, is much different in 2015 than in 1993, which puts the framing analysis as a post-rationalization that's essentially comparing apple-and-oranges.

> And lastly, you will probably have to work long hours. But that wouldn’t have mattered to me in my 20s.

Isn't one of the primary criticisms of modern startups that they abuse naive fresh-out-of-college graduates?


>Isn't one of the primary criticisms of modern startups that they abuse naive fresh-out-of-college graduates?

Precisely. A 20 year old should go out and get a job and gain some experience in a space and then, maybe, they'll be able to identify and solve a real-world problem.

I had very little sense as a 20 year old. And yet, judging by some of the articles I read here, I was positively worldly compared to some of the kids who are getting big money and starting companies. I have a hard time coming to terms with why seemingly sensible adults think this is a good idea.


> and then, maybe, they'll be able to identify and solve a real-world problem.

And also then, maybe, they'll be able to judge whether a particular startup is solving a worthwhile problem and has a hope to succeed.


Isn't one of the primary criticisms of modern startups that they abuse naive fresh-out-of-college graduates?

The official Y Combinator solution to that is to replace them with naive, fresh-off-the-plane, H1Bs.


and they wont be recruiting eng lit grads in the main


I started out my career at Fidelity Investments too! And after a couple of years, moved into the startup space.

I agree with many points here - you learn infinitely more quickly, you work infinitely harder, and this has given me business and engineering acumen far greater than had I stayed at Fidelity.

I will disagree with the overall tone that, when we are young, salary is less important. It is certainly true that many of us have fewer financial obligations, besides perhaps student debt and rent.

But I would always advise against joining a startup at significantly below market rate just for the equity. Even as a 1st or 2nd employee, you can only control the direction of the company so much, you're working just as hard as the founders, but the upside is a fraction of what it is for them.

(Let's also remember that you're typically not granted stock, but stock options. So if you have student debt, join a startup as a customer experience associate, you may not even be able to afford to exercise all of them when you leave!)

If I had gotten a job at Google after graduating (let's say I had applied and gotten in) my starting salary would have been higher, and that would have served as an anchor point for all future salary negotiations - for the rest of my life! I've probably left ~100k on the table over the past 5 years due to this alone.

Today, I still have few financial obligations, but wouldn't take an appreciably lower salary for any company until I start my own. I have enough experience now to be able to negotiate that kind of deal, but if I were to do it again, I would try to be a little smarter about this point as well.


Fido is a great shop and 100K is relatively cheap for that important of a lesson... and of course we shouldn't ask too many what-ifs.


The risk of a startup has moved from investors to founders and now from founders to employees.

Investors diversify their investments to minimize the risk. They don't really care if a particular startup they invested in will fail. They have tons of other investments...

Now with this new generation of "entrepreneurs" who start five startup at a time, they are not too afraid of startup failure either. They did diversify their risk too!

The only one who really loses when a startup fails is the employee who bought promises of "learning a lot" or "probably getting rich" and compromised his/her income and lifestyle.

It's very hard to find a startup that is like early Google where everyone is firmly believing they are doing something huge and everybody is all-in the company.


I generally agree with you that investors and founders mitigate their risk through diversity and networking. However, I wouldn't single out employees as "the only one who really loses when a startup fails." Like you said, choosing a Google-like startup is tough, and most founders believe theirs will be incredibly successful when they hire early employees. But I can think of at least one example where the employee of a failed startup will have benefited greatly, possibly more than the investor and founders.

Imagine an employee who chose the startup because she passionately shared its vision, and the position available was exactly what she wanted to be doing. She worked out a budget so that her family would be fine with the lower salary. She gets to do what she enjoys in a fast-paced environment learning many new skills alongside others who share her vision. If that startup fails, she's out of a job, and the equity she earned is worthless. If she was paid enough to stay within her desired lifestyle range without taking on debt, and she enjoyed working at the startup much more than she would have enjoyed being a cog in the BigCorp machine working on projects she felt indifferent about, then I believe her risk as a startup employee was relatively low.

Opinions will obviously vary depending on how important compensation (after a certain threshold) and prestige are versus working on what you want.


Some people make very good employees, but lousy sales people, when they are trying to sell their skills to a prospective employer. So becoming suddenly unemployed, especially after having a year or two of substandard pay (so no savings) can cause damage. Especially if it takes 6 months to find another job.

The only way I personally would work for a startup is if I could purchase supplemental unemployment insurance. I know you can get unemployment insurance on various loans (mortgage, car, credit cards, etc), and state unemployment pays a small amount. But I would like to see an option where the startup pays an insurance company to cover my full salary for up to a year (or until a job is found) after a business folds.


My first "startup" was a Rocket Internet company where I knew I'd have little career future, that my pay would be way below market, and that I'd get no equity (I was fortunate that the person who recruited me was upfront about it). Three years and two more RI ventures later, I've observed enough and figured out what to learn, learnt it and even found both my market and co-founders. This happened because of the breadth of work that needs to get done in a startup/"small underfunded mostly online company" and the lack of people available to do it, meaning little bureaucracy and much more responsibility, with immediate feedback from the real world on your performance.

Career switches are hard and sometimes, starting at the bottom again, risk included, can be worthwhile. I do agree with you that few people hired as "employees" should expect to "get rich". But provided you are willing to observe and learn, especially learn what to learn, it can still be worth it, even just to see what a hyped up "5-at-a-time" startup looks like from the inside and the signs of what to avoid.


Startup employees have a lot of advantages to mitigate this risk though:

- They can be much more selective of only joining startups that already has good traction

- They generally can command a higher salary than founders pay themselves

- If things go south they can jump ship much sooner

There are certainly disadvantages, but it is a free market. If you choose to go the startup employee route, then use all the advantages you've got available to you. Depending on a your goals being a startup employee might not be the right thing, but they can mitigate their risk just like everybody else.


The only reason I can think of to join a start-up as an early employee is that you want to some day do a start-up of your own and you want to acquire the relevant experience.

From a financial perspective it is a lottery ticket with a very high price and a low chance of paying out.


Not really. Unless you're using equity to compensate for a lower salary, which you should never do.

If the startup is offering a fair market salary + equity the only real thing you're risking is stability. Yeah you might only have the job for a year because the company goes under but short term employment is more common place now so that seems like a low risk.


> If the startup is offering a fair market salary

In that case, yes. But that's definitely not the way quite a few of those pitches go. It's more like: take this below market salary and this tiny bit of equity which will surely be worth more one day than the salary that you're foregoing today.

Of course it takes two to tango and you're free not to believe that spiel but I've seen it more than once in my own career.


I interviewed with around 20 startups in the Valley about a year and a half ago. Hands down every single startup that made me an offer had a shit salary.

After I ditched the idea of working in the Valley based on my experience interviewing there I decided to focus my search on distributed teams only.

What I found was surprising. Not only were these new startups outside the Valley offering remote work but almost all had higher salaries. It was crazy. Here I was thinking that the only way I could earn a high paying wage was to live in one the most expensive cities in the world. Little did I know that I could earn a market salary and live anywhere.

If I could give anyone advice about finding a new job at a startup it would be to seek out companies offering remote work. It's the only way to go.


What kind of skillset do you have though?

Here on HN there has been constant bemoaning over difficulty of finding good remote work.

The biggest issue has been that remote work pretty much requires living in low cost of living locations.


I mostly brand myself as a Product Designer. That job typically requires a decent knowledge of both design and development. As far as me specifically: UI, UX, CSS/SASS/HTML/JS, Rails & Ruby, Design tools like sketch and CC and some working knowledge of iOS development.


So she managed to graduate without student loans? All her obligations were rent? Good for her. Most 20-somethings coming out of college have a shitload of student loan debt. Myself included. Equity sounds nice, but it doesn't stop Sallie Mae from calling and demanding her money back, plus interest.


> And for much of my 20s, I worked long hours anyway—but others benefited financially from whatever I did, not me.

This is not true, unless Livingston was not paid. An accurate statement would have been "I worked long hours anyway—but others benefited more financially from whatever I did."

But guess what? This is true when you're an employee at a startup too. Founders, executives and investors will almost always have significantly more to gain than you, and their relationships with the company are going to be structured more favorably than yours is. So going to work at a startup is hardly a panacea for folks who can't live with the fact that somebody else is profiting from their labor.

> And remember, working isn’t just about making money. It’s also a form of education. And at a startup, you learn a lot faster about how companies work and how to make a great product than at a big company.

This isn't necessarily true. Lots of startups are chaotic and highly dysfunctional. And many don't produce great products. Depending on the type of startup you go to work for, you may exit the experience with a whole lot less in the way of transferable skills than you expect.

> ...having to explain to crackpots why their mutual fund account went down that day.

Tangent: I'm really surprised at what's coming out in some of the recent writings of people associated with YC. It's unfortunate that some folks who have money in mutual funds don't understand how they work, but the use of the word "crackpot" here is as unjustifiably contemptuous as claiming that "most people are very lazy"[1].

[1] https://news.ycombinator.com/item?id=8858942


>This is not true, unless Livingston was not paid.

No, the word "benefit" implies additional value (like "profit") above and beyond the break-even trade.

It's entirely possible to "not benefit from the work" on a nonzero salary.


The "work for a startup so you get high risk equity" argument is a bit silly. You're better off working for a high salary and investing as much as possible into asset classes with less risk. However, the "you'll learn a lot while working for a startup" part of the argument makes sense. You're investing in your own human capital and if you can't bet on yourself who can you bet on?


It's also good to diversify. Bigger companies solve different problems and reach more people. This makes the problems often more challenging and interesting than startups.

You may have an easier time implementing the newest/fanciest tech at a startup but it's often the big companies where that tech is being created or where it could really move the needle :O.


I've been doing some heavy investigation to how (and where) I should start my career in terms of maximizing learning. I have friends who will be working at Microsoft, and other friends who criticize said 'Microsoft' friends, saying that they won't learn much. Others say you learn the [most] at big companies, and a small minority say that start-ups are the way to go when you're early in your career.

I wonder what advice Jessica (and the HN community) would have for people like me, as I imagine there are a lot of people like me visiting HN.


> I have friends who will be working at Microsoft, and other friends who criticize said 'Microsoft' friends, saying that they won't learn much.

There are many things to criticize about the dev experience at Microsoft, but that's definitely not one of them. Unless you're in a quite dysfunctional group, there is extensive early-career training and explicit mid- to late- career mentoring there that really distinguishes it from startups and other big companies. As a manager there, I was held responsible for growing my organization's devs much more explicitly and to a much further "minimum ceiling" career stage than I've seen or heard of from any peers at other companies or other places I've worked.

Of course, things may have changed since I left that position in ~2006.


My first job as a developer was at a very small infosec non-profit (5 employees total!), I now work for a fairly large tech company (VMware) - and while I was in school I worked tech support at a startup that grew from ~30 to ~80 employees in the year and a half I was there.

So I've seen a decent range and think that you'll learn a lot wherever you are (particularly early in your career). What you learn will vary a bit and you will most likely prefer one or the other, but until you've tried both I wouldn't worry too much about which is better. I'd suggest pursuing opportunities at companies of all sizes and accept the offer that most interests you.


The advice that I got was to join mid size startup (Think of google 2004, FB 2007, or uber/ airbnb/ dropbox right now). The company has been mostly de-risked, and there is still newer parts of the organization where you get to do interesting things.


I joined a startup as the first employee shortly out of college and I've been here for almost two years. I would say I've probably learned more here than I would've elsewhere because I jump up and down so much of our stack. I've gone deep on a few technologies (Akka, ElasticSearch, CoreOS/Docker) while gaining breadth in a number of others (Neo4j, Rails, AWS).

I don't think I would've gained the responsibilities I have here as quickly as at larger companies.


This is interesting to read but a one-sided perspective. It can also go the other way, where going into the startup world is a big career mistake and is later regretted. A number of my female friends joined startups right out of college. Multiple busts/layoffs/firings later, they realized they had a disjointed resume, with short experiences at companies no one has heard of, and worse - few skills to show for it. They never progressed beyond customer service and various other administrative, low-paid positions. On the other hand, after a short stint in consulting/banking, other friends gained skills that they could leverage for much better positions in both startups and the corporate world. Yes, working for a company like Deloitte or GE expands your choices later on. For some reason, lack of career progression seems to impact women in startups much more than men. I think it's because there are so few women at startups - and male founders bring in their friends/other men they're comfortable with for interesting positions. The good news is that although they "lost" 4-8 years where they didn't learn much, these women were able to finally get going with their career - either through graduate school (MBA, law school, going into medicine) or getting an entry level job at a large company (Facebook, Cisco etc) where they were able to work with MUCH more senior people in a business team and actually learn things.


Why is it so important to join a company that is structured in a particular fashion?

Rather than work in an industry that you love? It seems to me to be a case of function following form.


Most of the comments are missing what to me is the main point, which to me can be boiled down to:

-----

1. Early in your career, gaining knowledge, skills and proof of same can be more important than immediate income.

2. Doing something for which you're "underqualified" is commonly a fast way to learn (and to prove that you've learned).

3. Start-ups are relatively likely to pay you to do something for which you're underqualified.


Basically, college grads today should do exactly what college grads were doing during the dot com boom? Yeah sure that's great advice!


For what it's worth, I chose the small startup offer over the name brand offer after graduating from a top school. My advice would be to TAKE THE NAME BRAND OFFER. Jessica's points were not true in my experience.

"Yes, startups are very risky, and they often fail. But when they don’t fail, their stock can become quite valuable."

The startup I worked for actually was pretty successful by most measures. In fact, I've now worked for two "successful" startups as a relatively early employee -- one acquired for XX M and another for XXX M. When all was said and done, I would have made more had I gone to a company like Google. You will get diluted, the investors will get their liquidation preference, part of the acquisition will go to retention incentives, and whats left over will be a fraction of the numbers you see in the media. Literally, the only way you will make anything comparable to a founder exit is if the company IPOs and becomes Facebook.

Also, most big companies give large stock grants. When I graduated, the stock grants Google was giving to recent grads would now be worth well into the 6 figure range. Not life changing money, but comparable to what you would get in a decent sized exit at a startup. I'd also add that joining a company like AirBnb is not the same as joining a startup. I'd imagine the AirBnb experience would have more in common with joining Google than joining Zip-tify-io-ly.

"It’s also a form of education. And at a startup, you learn a lot faster about how companies work and how to make a great product than at a big company."

NOT-TRUE-AT-ALL. If you go to work at Google, you can still work on a new product. The big difference is that at Google you will be surrounded by experts in their fields. You will learn what it takes to build a scalable product, how to build things in a modular and parallelizable way, solid coding practices, how to work on a team etc.

At a startup you "might" learn those things, but you very easily might not. My experience is that a lot startups carry massive technical debt. Their products tend to be hacked together because they didn't have an expert in (python, javascript, databases etc.) when they built the product. So, worse than not learning a lot, you might be learning exactly how not to build a product and spending all your time cleaning up spaghetti code. Plus, at Google, your product might immediately be in the hands of millions of people. The vast majority of startups never even find a product-market fit.

Bottom line, in my opinion it makes no sense to join a small startup as an employee from either a financial or career perspective. If I had it to do over again, I would have gone to a more established company with name-recognition out of school and built savings, skills, a social life and connections. After a couple years at one of those companies, you can write your ticket to any role in the industry, including founder of a VC-backed startup. You'll have an insane network, enough savings runway to build your idea and actually have time to enjoy your early 20's social life.


Thank you for providing this perspective, I completely agree.


Secure corporation vs. high-risk startup seems to be a false dichotomy. Many people start a business that doesn't even remotely aim to be the next Google or Facebook: highly specialized software, support, infrastructure, ... That's a career path worth considering for all who can think and act economically.


Honest question. How many 'early stage' startups would hire an English major straight out of college? The only way I see this working is if they already know the founders beforehand or if there are varying definitions of 'early'.


This was what I was thinking as well. The article is written as if she had turned down the option to join a startup or even had a chance to join one with her skillset, and I have a hard time believing that is the case.


Graduates fresh out of college have the one thing that's most important for long-term wealth accumulation on their side: time. Take two scenarios, for instance, both assuming retirement age of 65 and a long-term average stock market return of 7% annually.

Scenario one: Smart 20-year-old college grad accepts an offer to go work for Big Tech, Consulting, whatever. Their salary allows them to pay down any student loan debt they might have, build a cash cushion, and sock away $10K/year for retirement. At 35, when they've built valuable industry experience and connections, they decide to go out and do their own thing. They stop investing in their retirement account, putting their cash into the startup or raising money, and let the retirement account sit and grow with compound interest.[1]

Scenario two: Smart 20-year-old college grad decides against the BigCo route and founds a startup (assuming this is even feasible given any loan debt they might have). Maybe raises a small funding round, takes a low salary...everything goes back into the business. There is no investment into a retirement account. Let's say they meander through startup land up until 35, making some money here, losing some there and given the high failure rate of startups never really sees the "big exit". At 35, when things like marriage and family happen, they're forced to take a job at BigCo (or MediumCo, SmallCo, whatever) and finally have the means to start investing something into a retirement account. Let's get aggressive and say they put in the same $10K/year that scenario 1 grad did up until 65 (hard to do if you start having kids, buy a house, etc).

At 65, scenario 1 grad would have $2,046,783 in their retirement account after just 10 years of investing $10K/year and then letting it sit and collect compound interest. Scenario 2 grad would have just $1,010,730 in their retirement account after investing $10K/year over a period of 30 years. The difference between scenarios comes out to over a million dollars!

Obviously there's an endless list of variables that could throw a wrench in this model, but the point is that people who fail to assess the time value of money and the opportunity cost for a dollar spent (or not invested) today vs. one invested over the long term do so at their own peril. If you're 20, just $1,000 invested into the market once will turn into $21,000 when you're 65. If you keep putting money in regularly, this amount will grow significantly and the sooner you start the more it will grow. It's up to each individual to determine the right path for them, and I'm not saying it would never make sense to go do a startup when you're young (you have more energy, creativity etc), but you must be aware that the tradeoff is losing valuable years early in your financial path that you will never be able to get back. Arriving at the same spot at 35 that you could have started at at 20 will put you significantly behind others who have used those early years to put the miracle that is compound interest to work for them.

[1] http://www.moneychimp.com/calculator/compound_interest_calcu...


OK, I've been trying to be nice here, but this is just too much. 7% annual returns in the stock market? Good luck with that, buddy. I'd be happy to get a guaranteed 4%, but I doubt it will happen. How about a team of unicorns to pull my coach to work every day?

Guess what: you are never going to have financial security unless you win the startup lottery. If you make 150k a year instead of 100k, the colleges you send your kid to will just charge you an extra 50k in tuition. The more you make, the more they charge. Great model, eh?

Middle class savings are ridiculously inadequate to modern expenses. Even a few days in the hospital could set you back hundreds of thousands of dollars if the bureaucrats at the insurance company decide it's not covered. In a divorce your partner will get half of the house, half of the money, and probably a permanent monthly stipend out of you (at least in California).

You're either one of the 1% or you're one of the poor. So take your chances and roll the dice. If you succeed you will be able to pursue whatever other dreams you want. If you fail, you'll just take the safe job at IBM like everyone else. Retirement is mostly a scam anyway and odds are none of the savings you've accumulated will mean squat when the big one drops / singularity hits / Sarah Palin becomes President-for-Life.


None of these numbers are adjusted for (estimated) inflation, right?

For instance, $1,000 from 1969 was worth the equivalent of over $6,000 in 2014 (45 years later, same as "start work at 20, retire at 65" examples)

So the benefits of investing, while not poor, are substantially less impressive than they appear from the raw numbers. That $21,000 of 2060 dollars might only buy as much as $3,500-4,000 in 2015, when that first $1,000 was invested.


You can ignore the impact of inflation since his argument is that the earlier investing results in a greater net worth at a later time.


Worked at 4 startups, 1 got sued, 2 went down, 1 chugging along barely breaking even, stock worthless.

Should have taken the salary.


I suspect that these arguments are very familiar to HN readers. Thus, I don't know why it's on the front page.

Sure, Jessica Livingston is a reliable author, but most readers already had high enough confidence that these arguments are true such that this article didn't change much.


> Thus, I don't know why it's on the front page.

The ranking algorithms are really weird on the weekends due to the lower volume of submissions.


'Yes, startups are very risky, and they often fail. But when they don’t fail, their stock can become quite valuable. I wish I’d taken a job as an early employee at a startup and gotten some equity when I graduated from college'

The author means she wishes she'd joined a -successful- startup. That, or she wishes she'd had better challenges out of college, ones that she still could have completed, though (rather than just taken a job at a startup yet failed to be productive at it). The problem is that the former is impossible to pick, and the latter isn't guaranteed just because you joined a startup.

You should be picking a job at a startup with the assumption that the startup will fail. Is this particular startup opportunity you're looking at (not 'it's a startup!', but, 'it's a chance to work at X, using technologies Y, with team members of Z, management seems good, the environment seems good, the compensation is good enough') worth it, given that?

And if you take it, periodically ask, given this startup will fail (take that attitude, even if things are beginning to look positive), is the environment still worth it?

The fact it's a startup, the fact it includes equity, are -terrible- reasons to stay at a job that you aren't growing in and learning to enjoy.

I've experienced good enterprise jobs, where I felt I had a massive say in what technologies were used, in what tasks we prioritized, and felt extremely responsible to get things done, to where I felt I was constantly learning, and better yet, felt incentivized to go learn more on my own. I felt that my efforts were recognized, that my management gave a damn, and that collectively my department was effective, and supportive, and that my time was respected.

I've experienced bad startup jobs, where I felt micromanaged, that I had no say, that my tasks were constantly shifting and never under my own control, and that the existing cruft from prior pivots was so large that I had no real freedom to experiment or expand into the areas other people, who were more knowledgeable about the code, were working in, and by the time I left I felt I had learned nothing, and felt so drained at the end of the day I had no inclination to do anything on getting home. I felt unrecognized, viewed largely as a useful code monkey, that my time was not respected, and that collectively everyone was just in it for the paycheck and the hope of an eventual payout of their equity.

Take articles like this as reasons to consider a startup, but NOT as "startups are better". Just because something is a startup is not a reason to take it, just as it's not a reason to dismiss it. Whatever opportunities you face are specific to you, and they should be evaluated by you based on their actual merits.


Clearly since Ms. Livingston was graduated from college, she has learned a lot about the economy, business, start-ups, making money, getting financial security, careers, and jobs. And likely and apparently she got a good marriage. Good.

History

But nearly unbroken history of at least the past 200 years shows that the knowledge frontier she reached keeps moving forward. So, yes, likely Ms. Livingston knows more about start-ups, etc. than her mother did, but, even so, it is not clear that she knows enough about start-ups people in their teens and 20s need to know now to do well to get started on doing well in the rest of their careers.

Do well? Sure: Have to select the good start-ups and f'get about the rest. How to do that? Not easily, e.g., the venture capital world tries but, from some data posted by VC Fred Wilson on his blog AVC.com (1) about 2/3rds of the start-ups he funded flop (don't do well, or some such) and (2) on average the return on investment (ROI) of US information technology start-ups is poor, less good than Ms. Livingston helped obtain in her first job in Boston that counted the minutes she was on her coffee breaks.

Sure, Ms. Livingston might have majored in computer science and joined Microsoft in 1990. Alas, we come this way only once, and we don't get do-overs or re-dos, at least not until we get a time machine.

So, what to tell young people now?

Since Ms. Livingston is talking about start-ups mostly in information technology, we should consider such things, and there is less to the significant history there than often meets the eye:

(1) In the 1930s, Bell saw clearly that vacuum tubes were too big, expensive, unreliable, and hot for the future of the US long distance phone network. So, a better amplifier was needed. They had a solid state rectifier, so what about a solid state amplifier? They started a project. WW II got in the way, but soon after the war, presto, bingo, fireworks in the sky, a giant step for Bell and a much larger step for mankind -- the transistor.

Exercise: Why so important? At the time Bell saw the importance for civilization and, thus, decided not to patent the transistor. So, write an essay that might have been written in, say, 1949, on why the transistor should be so important.

(2) Soon enough the Cold War caused the US DoD to want a lot of digital electronics for aerospace, and thus, erupted from Stanford, due in part to Dean Terman, Silicon Valley to supply electronics to the US DoD and later NASA.

(3) Fairly soon Silicon Valley saw how to put several transistors on one piece of silicon and make integrated circuits. Gee, could make little devices! An electronic calculator to replace all those mechanical parts? Sure: But, still, need a lot of transistors, maybe more than for just a small, simple, general purpose computer where the rest of the calculator functions are just from software? Yup. So, bingo, simple microprocessors.

(4) NSF: MIT had some ideas for interactive computers with a lot of security. So NSF funded their Project MAC which did the operating system Multics with an hierarchical file system and security features capabilities and access control lists. For authentication, MIT did Kerberos. Then Kerberos made use of RSA encryption, also from MIT. Big things still with us; moving right along here.

(5) Bell Labs again: They wanted word whacking. DEC had a mini-computer, so Bell borrowed a little from Multics, etc., wrote a simple operating system Unix written in a simple programming language C. Later Bjarne Stroustrup, also at Bell Labs, wrote a pre-processor for C to support software objects -- the pre-processor was called C++.

Since Bell was a regulated monopoly, they couldn't sell Unix so essentially gave it away. A group at Berkeley, as I recall funded by the US DoE, did more with UNIX and made their work available as the Berkeley Software Distribution (BSD).

Unix became Linux, and C++ and software objects are still with us.

(6) Lots of people, not just Bell, were struggling with typing. IBM had their Selectric and, eventually, a correcting Selectric with a little white ribbon that would remove from the page a character struck in error. But, why no actual word whacking? Okay, Apple II, IBM PC, WordStar, etc.

Biggie. Really big biggie.

(7) We got Microsoft that recapitulated the mainframe history in operating systems, and Intel came along with microprocessors that recapitulated the mainframe history in processors. Now WinTel put on "every desktop" a computer for word whacking, Microsoft Word, and business arithmetic, Excel. Gates on the way to being the richest person in the world. Not too doing too badly, Paul Allen, Charlie Simoni, Nathan Myhrvold, etc.

(8) Ah, the US DoD again: It wanted battlefield communications, where even if shoot holes in some of the equipment the rest still works and provides communications. So, we got TCP/IP, e.g., in BSD, that is, we got internets. Soon labs were connected, and we got the Internet. Soon NSF funded it and IBM ran it. With HTTP and HTML for a particle physics newsletter by Tim Berners-Lee at CERN, we got the Web. Companies put their company brochures on the Internet.

(9) For the Internet, we needed more in communications capacity. Enter Bell labs again: They'd seen that one coming, too, and had been working on Ga-Al-As (as in the periodic table from a chemistry book) solid state heterojunction lasers and had the solution. Bingo: Send at 40+ billion bits per second (Gbps) on one wavelength, some dozens of wavelength on one fiber, some dozens of fibers in one cable, maybe several cables along a pipeline, electric power line, railroad track, highway, river, ocean shoreline, across an ocean or few, etc. Now, watch movies!

(10) Presto, IBM and others learned more about putting magnetic dots on surfaces, and now we have hard disk drives in the 3 1/2" form factor size with a few trillion bytes each. And HP is on the way with a trillion bytes, solid state, on a postage stamp.

So, now we can build server farms at Google, Facebook, Twitter, Microsoft, Apple, Amazon, etc., and we can have start-ups like SnapChat, PInterest, Box, etc.


Future

So, what lessons for the future might a young person draw from this history?

(1) Science. Off and on, some amazing science, especially physics, played a huge role. Maybe that will continue.

(2) Information. The desire for information, create it, transmit it, store it, use it, etc., seems nearly unlimited.

(3) Logic. Want something done? Well, describe the work in clear steps. For a lot of work done manually in offices over the past 100 years, such a description is now usually fairly routine. Then with such a description, fairly routinely can write software to do the work. So, can automate a huge range of old, manual work of office workers. That's a lot of what for some decades made IBM successful.

(4) Social. People are highly social animals. Or to paraphrase E. Fromm, The Art of Loving, "For humans, the fundamental problem in life is doing something effective about feeling alone." In more detail, since humans are also thinking animals, we see that alone we are at risk, that is, vulnerable to, say, the hostile forces of nature (earthquakes, blizzards, tornadoes, floods, wild fires, disease) and society (war, crime, economic depression). Knowing that we are vulnerable, we are worried (have anxiety) and seek security. We feel more vulnerable when alone so want to do something about being alone. From Fromm again, the first recommended solution is a good romantic relationship. Next is a good version of religion -- get all wrapped up. Next is membership in a good group -- get acceptance and approval, a feeling of belonging. Next, not recommended, is what some college students try -- get drunk on alcohol, high on drugs, and go to an orgy. So forget about the worries until recover (but have more worries).

So, to do something about the worries, we want security, financial and emotional, don't want to be lonely, do want to be loved, want a romantic relationship, want to belong, etc.

More generally we will want to form good families and be in good communities.

We will be using computing and the Internet for all they are worth for such things.

(5) Economic Security. Likely second only to love, and maybe more important than love, and maybe essentially a prerequisite to love, people want economic security, and for that there is a famous one word answer "more".

The drive to use logic, software, computing, the Internet, etc. for "more" will remain powerful for decades, maybe centuries.

(6) Information. Now one of the keys to more in economic security, "more", is information, and the drive for that will also continue for decades, etc.

For information, we take in available data, process it, and report the resulting information. This processing is necessarily mathematically something, understood or not, powerful or not. Then clearly one approach to more powerful processing and, thus, more powerful and valuable information, is to use mathematics to determine how to do the processing.

E.g., how to look for oil? Okay, often oil collects in pockets in the subsurface layers. So, let's map the layers and look for pockets. How to do that? On the surface, have something go "boom". Sound waves go into the ground, and they get reflected off the layers so that there is a convolution. So, to find the layers, take the resulting signal and do a deconvolution -- Enders A. Robinson, 'Multichannel Time Series Analysis with Digital Computer Programs'. The fast way to do deconvolution? Sure, the fast Fourier transform.

Once get the oil out, over here have all that oil, from Texas, the Mideast, Venezuela, Canada, etc. -- typically it's all different. Over there know what can sell -- methane, propane, gasoline, Diesel, heating oil, motor oil, etc.

So, how to take the available input and sell the output and make the most money? That's a math problem, in particular in optimization. Long the first-cut approach was via linear optimization (programming in the sense of operational planning). At one time, IBM had fun selling mainframes to Houston for just this work. But linear programming is not quite the right stuff. So, want some non-linear optimization. Well, for more details, see the work of Christodoulos A. Floudas in chemical engineering at Princeton. Houston does know about Professor Floudas.

There's much more to do. Right: Likely not a single VC in the country says that they want to see some especially valuable software based on some especially powerful mathematics. Hardly a one. And they are not comfortable backing something they understand so poorly. So, right, a lot of confused and unhappy VCs (they so richly deserve it!) but: Presto, bingo, opportunity. Besides, the main raw material into original mathematics is paper, pencils, and coffee, and how expensive are those?

Almost inevitably, there will be only a few people going that way with the rest heaping ridicule, etc. Not nearly new: Think of the Mother Goose story The Little Red Hen.

Secret: It turns out, no matter how much advanced and/or original mathematics you use, nearly always a lot of the actual computations will boil down to linear algebra and there, numerical linear algebra. So, take linear algebra, elementary, intermediate, advanced, applied, numerical, and related subjects such as linear programming, non-linear programming, multi-variate statistics, ordinary and partial differential equations and their numerical solutions. For more, study the leading generalizations of linear algebra, functional analysis, e.g., Hilbert and Banach spaces.

(7) Niches. One of the standard ways to make money is to have close to a monopoly, and one of the standard ways to do that is to have a niche of some kind and where the monopoly is protected by, say, a geographical barrier to entry, an especially good product or service, some crucial, core, defensible technology or know-how, a good customer list, some network effect, etc.

So, go for it!


I think startups can be romanticized so I'm sharing my startup story and some of the things I did do and some of the things I should have done.

When I was 23 I joined a startup as employee number 4. We did Salesforce implementations for small businesses using freelancers. At the time it was the CEO, Director of Sales, and another Project manager. I was originally hired as an admin assistant but after I taught the other project manager what a Gantt chart was, the company decided I was ready for the big time.

The company eventually fell apart due to internal conflict. The CEO had already started another successful web design company during his teens. He was extremely driven, charismatic, and caring, (and better than me in almost all the ways that count) but he did seem to have lost something due to working so hard for so long. The director of Sales was an absolute beast at what he did well, which was sales. Our pipeline was always bursting, but the customers expectations were often for things that were technically impossible (integrating Salesforce with Outlook at the time was terrible). He was clinging on to a fading dream of entrepreneurship. He didn't talk about his past, but he had worked in enterprise, and started his own business, but he hadn't reached the parabolic heights that he'd hoped for. The PM (project manager) was a friend of mine, and a friend of the CEO. He was extremely smart, but sometimes an idealist, and at the time not a very experienced negotiator.

I started at the company because I had been working at a big business that didn't offer me full-time work. Straight out of university I needed a job, so I'd have quick cash. I had an Arts degree and just wanted anything to start, so I took what I could get. They had me on as a temp, and I was fearful. I wanted security and one of the ways I saw to get it was to threaten to leave, so I put out my feelers, and the PM answered. My boss at the time couldn't put me on, and even if he'd said he would, I probably would have left for the startup. I figured, it could be the next Facebook.

At the interview, the Sales guy grilled me, but one of my strong points is interviews, so I nailed it. I even asked for more money, and I got it! At the time, I didn't ask a question which I should have:

1) Ask the founders why they need another employee

Hell, this probably wouldn't have changed my answer to their offer, but at the time they were looking for relief. The PM was overworked, and they needed him supported. In retrospect, they didn't know what they wanted. I kind of wanted an assistant role, and at the time didn't know I wasn't the best at project management, but that's what I ended up doing. I think in most startups the original employees don't have much choice - they do what needs doing. Find out what that is so you know what to expect.

I also did one thing well:

2) Have a realistic discussion about money

I asked for more money than they had offered in my interview. You should already know what the startup does, and you should have a fair idea of how cash poor or rich they are. This became even more important for me later. However, don't assume because you're working for a startup that you need to get paid nothing. Startups fail, and if that happens all you're going to have in your pocket is the cash. Trading experience for food is a little less convenient.

I started working. It was hard and I was in the deep end. I bought some experience to the table that they didn't have at that point, and I got my first sales experience, which I hated. I hated project management less, but what I really loved doing was development. For the work we were doing, development was quite light. The hours were long, and we hired devs, predominantly in India, to do configuration. The projects stretched out, often because I hadn't communicated with the customers well enough, and because the customer's expectations were not aligned with ours/reality.

3) Understand the customer

We were working for small businesses. This meant that a small amount of money meant a lot to the customer. The level of technical understanding of the customers was also low, which could be either extremely positive (importing csvs sounds complex and don't worry if it takes a month) or extremely negative (why can't you spell check e-mail addresses automatically). Additionally, in the end we were working for Salesforce. They didn't care how long it took us, they wanted the customer satisfied so they could get that sweet monthly SaaS payment on into the future. All this lead to extremely drawn-out projects, because that's what our customers demanded. That meant long hours, and lots of anger.

4) Understand the competition

I think this was the most crucial thing I didn't do. In the small business space for Salesforce, companies rise and fall all the time. I think this is due to the volatility of the customer type. It seems like the success strategy for companies in the space is to move to the medium-customer segment, effectively leaving the small businesses behind. I honestly have no idea if that was our strategy, but I probably wouldn't have joined the company if I'd realized how fraught with risk our market was. I even had another friend who had worked in the space, and shut down their company. In the end our competitive advantage seemed to only be how high our customer's expectations were in the sales pipeline.

5) Evaluate perks versus effort

If something goes wrong and you have to work until 3AM (and it will and you will), a bottle of expensive vodka is still less expensive than your hourly wage would have been. Is an office pet and an open bar worth the time you're spending at the office? Ask yourself this question often, because you'll be spending a lot of time at work.

At this point the pipeline was getting totally stuffed with old projects that had been drawn out for months because we couldn't deliver on our promises. Our desire and need for new deposits still grew, however, and so the pressure continued to build. The sales director was restless with this. I had been so excited at the beginning of the company to help design our processes, but we continually revisited and redesigned them, so much so that I think we went through 4 different visual designs for customer quotes in the 6 months I was there. I didn't think this was normal, and I felt like we needed more stability.

6) Remember that X% of $0 is $0

As the company became more fraught with drama, all the non-founders (there were now 6 in the company) were offered equity in the company. The first issue with this was that the company was surrounded by a bunch of other companies with different names, so we had no idea where the money was going. The second issue was this was a verbal agreement from the sales director. At this point I decided to leave the company.

I don't think there were any other lessons to learn, and I think I came out of the experience as a better person. If I'd turned down the offer I'd probably be reading Hacker News all starry eyed thinking startups were the promised land. They aren't, but they are fun, and I'd recommend everyone try them. But, protect yourself. Ensure you know what you are getting, and be realistic about the outcome at all times. If you are living hand-to-mouth as a college grad, don't rely on a successful exit as your savings plan.

In the end, I went crawling back to my old boss, but he hired me full time without an interview, and offered me more money! Taking into account my unpaid overtime, I got a 100% pay rise :). I was hurt by the experience, and the startup had threatened to call the cops if I didn't return my laptop and phone on the day I left, but looking back on it now, what a laugh! I felt taken advantage of, but I got valuable sales experience, learnt more about working with external devs (although I'm still not great at it), a chance to design processes for a company from the ground up, a better nose for bullshit and a few expensive bottles of vodka! It was an exhausting six months.

After I left, the founding CEO got f@#ked out of the company by the sales director, and then the sales director got f@#cked out of the company by the new CEO. The equity never materialized. The best story is of the other PM, who managed to score two medium-size enterprise clients for himself, and now earns six figures and works only a few days a week!


This post looks like it could be an awesome blog post and thread on it's own!


Thanks :)


This site is so busy it almost reminds me of a tabloid:

- three signup buttons (top-right and top-left, and the bottom of the article)

- permanent left overlay

- permanent double overlay on the top, including 9 'share' links

- red banner at the top for the latest campaign

- popular linkbait articles with pictures along the left side

- self-advertisement in the middle of the article

- giant modal signup popup after about 10 seconds of activity -- "Are you Prepared for Your Next Interview?"


I completely agree! One of the worst reading experiences I've ever encountered.




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