3/17/16

I've always considered myself entrepreneurial at heart. Even since I've started my work in IB, I have continued to work on developing a few "back pocket" ideas that I'm excited about. Indeed, ever since I can remember, I have wanted to start my own business, not because I hope to be the next Zuckerberg, but because I believe the ability to dictate your own work is more rewarding than any other employment experience out there. It remains my ultimate career goal, and with any luck, I will make it happen some day.

That said, I have to say that the rising fad of "start-ups" in what has been - arguably - a VC bubble (read more) has started to trigger my inner skeptic. Don't get me wrong: I think it's great that we are increasingly encouraging young people to take career risks and try to create value through entrepreneurship. But I couldn't help but be suspicious that there were a fair number of people getting the short end of the "start-up" stick, if for no reason other than the fact that the few friends I had that went to work for early- to mid-stage start-ups left their corporate jobs filled with enthusiasm and are now silently trying to break their way back into what we all know collectively as the machine of corporate America.

Curious to learn more, I sat down with a friend of mine who founded a mildly successful internet venture, backed by a sizable portion of angel investment and a recent round of VC funding. While he, as you might expect, was overall very satisfied with his career decisions and current role, he did confess that his experience was far different from the one he had imagined when he first completed his round of VC funding.

Perhaps most surprisingly, when I asked him about his thoughts on taking a job at a start-up, his knee-jerk response was, "Don't do it." What ensued was surely one of the most interesting discussions I have had in a long while. Particularly, we addressed many of the "myths" of start-up jobs, and, after doing some independent reading, I though I would share some of the insights. Take them at face value, feel free to dissent, but I found it quite staggering to hear from one of the most entrepreneurial people I know. So with that, a few "myths" of start-up jobs:

  • Myth #1: "Don't worry about the pay cut, you're going to get equity in the business. More than anything else, my friends who joined start-up companies were thrilled about the concept of getting an equity stake (albeit a small one) in the business. All they had to do was work hard (at a place where their effort was far more likely to be noticed, due to the smaller workforce) and they would ultimately be paid off in the form of equity ownership in a growing business. Most people joining start-ups are under the impression that their initial equity package is just a teaser of what's to come, but the truth is quite the opposite.

    Start-ups, especially those backed by VC firms, are notoriously stingy with equity. Even those at the top of the organization often have less than 10% stakes in the business, and the chances of them willingly giving out greater shares of equity in a growing business (especially as time goes on) is vanishingly small. Many employees don't see their equity stake meaningfully increased even after years on the job.
    Perhaps more importantly, promotions, raises and bonuses are exceedingly rare at start-ups. Money is tight at small firms, and there is a prevailing belief that if the business is performing well, the appreciation in your small equity stake makes up for a lack of performance pay (though this is rarely a reflection of reality). 2.5 years after joining a start-up, my friend with considerable programming skills was still making the same salary that he was offered when he joined the firm. What's worse, he knew that at any moment, he could be fired without real cause and with no severance pay to speak of.


  • Myth #2: "If the company grows, you'll find yourself in an executive role at an early age." Although the concept of internal promotion seems to go hand-in-hand with the entire concept of a start-up, the reality is that there are shockingly few non-founders who work their way through the ranks at start-up businesses.

    In most cases, successful start-ups are forced to reach out of the organization for new talent as the business grows. This shouldn't come as a surprise to anyone, but recall that start-ups are often cash-strapped and pay salaries at below-market rates. Inevitably, titles become a form of currency at start-ups - a sort of non-cash compensation that is a key bargaining chip during negotiations with new talent ("we know we can't pay you what Goldman can, but here you'll be the VP of corporate finance"). In an attempt to make concrete the value of those titles, organizations have to find a way to keep people enough people in junior positions to give weight to the title of "VP". Since you're currently the bird-in-the-hand, founders are often more likely to give you the snub in order to attract new talent by dangling more-senior titles in front of their faces. That leaves you - well - SOL.


  • Myth #3: "You get more responsibility at a start-up, which will translate into better experience." While the former is quite likely to be true, the latter doesn't necessarily follow so naturally. The reality is that in all types of business, there are undesirable tasks to be done, and often times, at early-stage businesses, there is even more mind-numbing work to be spread around. Like anything else, your experience is going to vary wildly based on the group of people around you (and this is even more true at start-up companies). Go with the law of large numbers on this one: as the number of people in an organization increases, the quality of work regresses to the mean.

  • Myth #4: "Our company is absurdly undervalued." This is one of the most common lines you will hear when interviewing at an early-stage start-up. We're all familiar with Mark Zuckerberg and the "Accidental Billionaires", so shouldn't we be on the look out for jobs at the "next big thing"? Surely that will pay dividends?

    For the most part, what holds true in the public markets can be easily translated to the private markets as well. That means that, for the most part, no one is smart enough to beat the market (not even the VCs, it turns out!). The chances of anyone (especially the founders, whose perspectives are understandably biased) being able to accurately determine the proper valuation of a pre-profitability business is next-to-zero. If you're thinking about joining a VC-backed start-up, you've already missed the train, and the chances that an early-stage VC fund left money on the table is tiny, at best.


  • Myth #5: "So being an employee at a start-up might not be so glamorous, it's being a founder that makes it really worth it." As we're all already aware, a tiny fraction of start-up companies ever get to the point where VC funding is a realistic option. But, for a second, let's ignore that fact and pretend that you have a sure-fire VC-backed idea marinating on the rotisserie grill of your mind. You've got it made, right?

    Not quite. Even at firms that are backed by $5mm+ of VC funding, it's not uncommon for C-level executives to barely pull in 6-figures in a year. VC money (unsurprisingly) comes with tons of strings attached, and if you're trying to hold on to your precious equity stake (and let's hope that you are, for the business' sake), they aren't going to let their money be paying you a handsome salary. Not until at least a Series C funding event are the founders really going to be pulling in the kind of money that is commonplace at the higher levels of Wall Street. And not until an acquisition or (more rarely) an IPO are you ever going to see the paydays that make founding a start-up so sexy these days.


So you're still not convinced? You're still going to jump ship to the new trendy start-up shop? Here are the tips that I was able to gather:

  1. Negotiate your desire equity package before you sign on. After you're on the bandwagon, it gets increasingly difficult to grow your share of ownership. If you're taking a career risk, make sure you're compensated for it.
  2. Get the title that you want tomorrow today. Promotion is few and far between at start-ups. And you only want to be working at a company that has a strong desire for your skills. If you're sitting across the table from someone that fits that description, obtaining a better title should be a fairly easy request to fulfill.
  3. Consider that there is still a boss when you join a start-up, and the grass isn't always greener. Although the idea of the start-up culture being liberating and progressive is pervasive, the reality is that you're still taking a job - a job that a cash-strapped company is willing to pay somebody else to do for them. Don't kid yourself, there will be plenty of asinine work involved.
  4. If you can't honestly say to yourself, "If I were making the same amount of money at this company in 3 years with very little business growth, I wouldn't regret my decision to join," then don't take the job. More than anything else, working at a start-up is about believing in the business. And if you believe in the business, you should be happy just to be paid to work somewhere you love.

Hopefully you find these tips as useful as I did. If nothing else, it served as a sanity-check for my long-held ambitions. And that's enough for me.

Further Reading:
The Downside of the Startup Failure Craze
Start-Up Lessons Learned
The 25 Best Start-Up Failure Stories
The Story of Nouncer's Failure
Four Myths about Start-Up Pay
HBR: Considering a Start-Up? Think Again

Mod Note (Andy): #TBT Throwback Thursday - this was originally posted on 1/203/14. To see all of our top content from the past, click here.

Comments (66)

2/21/13

Great insights

2/21/13

Great post NS

2/21/13

Thanks for the insight and advice!

2/21/13

there's nothing wrong with a side-hustle, just make sure you remember the difference between a hobby and a career.

2/21/13

Absolutely true:

And something you left which I've noticed when I was at startups was: just because the idea is killer doesn't mean that the guys running the show aren't totally incompetent. I've noticed that leadership at these places is really questionable...

My drinkin' problem left today, she packed up all her bags and walked away.

2/21/13

100% agree. I go to a M7, and I can't tell you how many people have the most "fad" ideas out there. Although I admire their determination, some things that they come up with are too simplistic too be successful enough to build a business out of, and frankly if I have someone else tell me about this revolutionary app they are developing I am going to kill myself.

"They are all former investment bankers that were laid off in the economic collapse that Nancy Pelosi caused. They have no marketable skills, but by God they work hard."

2/21/13

good stuff

Best Response
2/21/13

After working in VC, much of what the OP said is very true. Joining a start-up that already has VC backing means you will likely receive less than 1% equity in the company (unless you are joining at a C-level position). Additionally, you'll still be taking on pretty significant risk (remember, 1/10 start-ups succeed), with little/no job security (most VC start-ups will only have enough cash for around 8-12 months of runway).

Another good point the OP makes is that it's almost impossible to accurate determine the valuation of a start-up. To illustrate my point, look at Socialcam: it was doing well, strong growth, great team, great VC backing - once having a faster growth/larger user base than its competitor Viddy (once valued at $370 million) - what happened? Socialcam start losing users extremely quickly due to a change in Facebook's policies and ended up selling for "only" $60 million. Viddy's valuation will likely fall as well in its next round of financing. Even if you own equity in a "hot" start-up, they still have to make it to an exit before your equity is worth anything (and believe me, getting to an exit is not easy and requires a significant amount of time). If you join a start-up that underperforms and is sold off early by its investors, common stock holders will usually receive very little, if anything at all because investors have liquidation preferences and will be paid back first.

Frankly speaking, from my point of view, it's always better to start a company or be one of the first employees hired than it is to join a start-up that already has significant traction and VC backing (and no I don't consider companies like Twitter/Dropbox/Box/etc. start-ups). This way you'll get more equity, for a similar risk profile.

2/21/13

brutalglide:
After working in VC, much of what the OP said is very true. Joining a start-up that already has VC backing means you will likely receive less than 1% equity in the company (unless you are joining at a C-level position). Additionally, you'll still be taking on pretty significant risk (remember, 1/10 start-ups succeed), with little/no job security (most VC start-ups will only have enough cash for around 8-12 months of runway).

Another good point the OP makes is that it's almost impossible to accurate determine the valuation of a start-up. To illustrate my point, look at Socialcam: it was doing well, strong growth, great team, great VC backing - once having a faster growth/larger user base than its competitor Viddy (once valued at $370 million) - what happened? Socialcam start losing users extremely quickly due to a change in Facebook's policies and ended up selling for "only" $60 million. Viddy's valuation will likely fall as well in its next round of financing. Even if you own equity in a "hot" start-up, they still have to make it to an exit before your equity is worth anything (and believe me, getting to an exit is not easy and requires a significant amount of time). If you join a start-up that underperforms and is sold off early by its investors, common stock holders will usually receive very little, if anything at all because investors have liquidation preferences and will be paid back first.

Frankly speaking, from my point of view, it's always better to start a company or be one of the first employees hired than it is to join a start-up that already has significant traction and VC backing (and no I don't consider companies like Twitter/Dropbox/Box/etc. start-ups). This way you'll get more equity, for a similar risk profile.

+1

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/21/13

Good points. Not all startups are equal. Some will be destined for success but many more will fail. Don't be fooled by the initial social media boom. Speaking from experience, some founders are complete jerks who have serious ego problems and yet lack a real goal/direction in mind. They expect you to give your soul to helping them build their dream whilst giving you laughable compensation for your efforts. Not to mention some hide important information from you which really damages the whole early trust thing.

I think knowing as much as you can about the startup you want to join is extremely important. Make sure you yourself can believe in the company and join it without any lingering doubts. Otherwise you might want to reconsider.

2/21/13

I like when people leave to work at CoolNewDotCom.com, it means less competition for me, especially of my soon to be MBA class all want to walk the plank. Too many people think "Oh, I'll start a business and be free and rich and OMGZ rainbows" when in reality you're a small business owner who works to death and hopes and prays you make a living. Starting it on the side until it's sustainable is a more effective approach in most cases and most successful startup guys did just that.

Other thing is this: dot.com's are trendy right now, but don't overlook other industries! So many people are dazzled by YouTwitterFace that they forget about the other 95% of the economy. The goal is to make money, not have a turtleneck wearing ghost approve of you...

Get busy living

2/21/13

Which is the bigger form of career suicide: joining a startup or doing teach for america? Tough call.

2/21/13

mdk6c:
Which is the bigger form of career suicide: joining a startup or doing teach for america? Tough call.

If it's before MBA / grad school, these things can be a huge plus....

Get busy living

2/21/13

mdk6c:
Which is the bigger form of career suicide: joining a startup or doing teach for america? Tough call.

TFA straight out of undergrad is nowhere near career suicide. B-schools salivate at that type of experience.

MM IB -> Corporate Development

2/21/13

SECfinance:
mdk6c:
Which is the bigger form of career suicide: joining a startup or doing teach for america? Tough call.

TFA straight out of undergrad is nowhere near career suicide. B-schools salivate at that type of experience.

As do banks, consulting firms and law schools. TFA is similar to bschool in that is a fun/fulfilling type thing that is branded well enough that it won't hurt and will likely enhance your career.

2/21/13

Depends on your risk tolerance. I will admit that everything you said is true.

The real fact is that both the upside and downside potential of taking a job at a startup when compared to IB are larger. You need to decide on your risk tolerance.

Personally, I don't settle for the mediocre.

2/21/13

MogulintheMaking:
Depends on your risk tolerance. I will admit that everything you said is true.

The real fact is that both the upside and downside potential of taking a job at a startup when compared to IB are larger. You need to decide on your risk tolerance.

Personally, I don't settle for the mediocre.

Actually, talking with my friend, I was taken aback by the lack of "upside", even for the most successful ventures. Outside of FB / Twitter / Groupon / etc., in ventures that are lucky enough to achieve an exit at a premium valuation (say $100mm) often times early founders have less than 10% equity remaining in the company. Don't get me wrong: $5-10mm is a nice payday, but it's also nothing that you couldn't earn in a few years as an MD a a bank. That part surprised me.

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/21/13

NorthSider:
Actually, talking with my friend, I was taken aback by the lack of "upside", even for the most successful ventures. Outside of FB / Twitter / Groupon / etc., in ventures that are lucky enough to achieve an exit at a premium valuation (say $100mm) often times early founders have less than 10% equity remaining in the company. Don't get me wrong: $5-10mm is a nice payday, but it's also nothing that you couldn't earn in a few years as an MD a a bank. That part surprised me.
This is a great point and a lot of people don't realize this. You won't go hungry or anything, but after everyone else gets their pound of flesh, Uncle Sam included, you're probably not going to be able to go out and buy an $8mm plane.

Having said that, 10 times out of 10 I'd rather earn a $5mm payday as an entrepreneur than over a few years as an MD at a bank.

2/21/13

prospie:
Having said that, 10 times out of 10 I'd rather earn a $5mm payday as an entrepreneur than over a few years as an MD at a bank.

Agreed.

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/21/13

Really enjoyed this... have often wondered what some of the biggest misconceptions about start ups are and this was very informative...

2/21/13

Original article that a lot of this is drawn from. I think someone posted this on a different, earlier thread, but it's definitely worth reading in its entirety:
http://michaelochurch.wordpress.com/2012/07/08/don...

Certainly made me think twice about taking a startup offer I received that would have been terrible pay, little-to-no equity, and for which I should be grateful because the company is "doing really great things." Thanks but no thanks.

Hi, Eric Stratton, rush chairman, damn glad to meet you.

2/21/13

Excellent post.

"Dont compromise yourself; you're all you've got" - Janis Joplin

2/21/13

couldn't agree more. while i've never worked full time for a startup, i interned at 2 early-stage startups in college, and while my responsibilities were pretty vast, thus good for my resume at the time, there was a ton of bitch work that had to be done. on the one hand, as an undergrad, i was in charge of finance. on the other hand, i also had to make the printer work and set up the phone lines and negotiate with the phone company.

Remember, once you're inside you're on your own.
Oh, you mean I can't count on you?
No.
Good!

2/21/13

this is why I like bootstrapped start-ups and why I haven't taken $. Get a good team in place and delay taking VC money for as long as possible (if you need it at all) so that you can hold onto as much of the equity as possible.

The guys over at Warby Parker did this, and I can assure you they have WAY more than 10% because they had every VC tripping over themselves to fund the deal.

Early traction and revenue = higher valuation and more equity in your pocket. There are still a TON of interesting startups outside of .coms that shoudl not be forgotten....com's just get a lot of the attention because of the crazy success stories. Given how scalable the web is, it's the type of businesses that can be run with a small team and scale to massive size.

That doesnt mean someone shouldnt make a better chain of laundrymats that serves beer on tap...

2/21/13

WallStreetOasis.com:
this is why I like bootstrapped start-ups and why I haven't taken $. Get a good team in place and delay taking VC money for as long as possible (if you need it at all) so that you can hold onto as much of the equity as possible.

The guys over at Warby Parker did this, and I can assure you they have WAY more than 10% because they had every VC tripping over themselves to fund the deal.

Very much agree with this sentiment. My friend has a mildly successful travel services website without much capital requirement - I couldn't really understand why he would give up equity for VC funding that he didn't rightly need. Of course now he travels all over the country on the company's dime, has a nice office and a pretty glamorous lifestyle outside of a small-ish salary; however, I can't help but wonder if he won't regret selling equity to raise funds that don't directly increase the company's chances of success.

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/21/13

WallStreetOasis.com:
this is why I like bootstrapped start-ups and why I haven't taken $. Get a good team in place and delay taking VC money for as long as possible (if you need it at all) so that you can hold onto as much of the equity as possible.

The guys over at Warby Parker did this, and I can assure you they have WAY more than 10% because they had every VC tripping over themselves to fund the deal.

Early traction and revenue = higher valuation and more equity in your pocket. There are still a TON of interesting startups outside of .coms that shoudl not be forgotten....com's just get a lot of the attention because of the crazy success stories. Given how scalable the web is, it's the type of businesses that can be run with a small team and scale to massive size.

That doesnt mean someone shouldnt make a better chain of laundrymats that serves beer on tap...

Agreed 100%. There's also nothing wrong with starting something on the side that just makes you a little extra dough. Not every new business needs to be some billion dollar VC-funded venture.

Personally, I'd rather start and own something that brings me steady cash flow, even if it's sub-one million bucks a year, than run a company that has millions of dollars of VC backing (unless it was something I truly believed in and loved.) The first gives you freedom, the latter gives you a ton of work with a much less certain outcome.

3/17/16
WallStreetOasis.com:

That doesnt mean someone shouldnt make a better chain of laundrymats that serves beer on tap...

Running with this. kthanksbye.

2/21/13

To add - this isn't to say that having a little cash cow of your own wouldn't involve a good deal of work, but ideally it'd be something you could manage via outsourcing and remote working. Something that's got huge VC backing will likely mean cranking away like there's no tomorrow. Now, if you can turn your cash cow into something that VCs want to chase, like Patrick explained, that'd be awesome. But, I'm not even sure that it's the ideal life. It would seem, to me, that the ideal is to have a business (or occupation) that pays you enough to keep you comfortable and affords you the freedom to do what you please with your time.

2/21/13

TheKing:
To add - this isn't to say that having a little cash cow of your own wouldn't involve a good deal of work, but ideally it'd be something you could manage via outsourcing and remote working. Something that's got huge VC backing will likely mean cranking away like there's no tomorrow. Now, if you can turn your cash cow into something that VCs want to chase, like Patrick explained, that'd be awesome. But, I'm not even sure that it's the ideal life. It would seem, to me, that the ideal is to have a business (or occupation) that pays you enough to keep you comfortable and affords you the freedom to do what you please with your time.

Definitely agree with this sentiment. A small cash cow on the side sounds more ideal than a VC-backed start-up.

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/21/13

NorthSider:
TheKing:
To add - this isn't to say that having a little cash cow of your own wouldn't involve a good deal of work, but ideally it'd be something you could manage via outsourcing and remote working. Something that's got huge VC backing will likely mean cranking away like there's no tomorrow. Now, if you can turn your cash cow into something that VCs want to chase, like Patrick explained, that'd be awesome. But, I'm not even sure that it's the ideal life. It would seem, to me, that the ideal is to have a business (or occupation) that pays you enough to keep you comfortable and affords you the freedom to do what you please with your time.

Definitely agree with this sentiment. A small cash cow on the side sounds more ideal than a VC-backed start-up.

This cash cow sounds more like a cash unicorn. I don't of many side gigs that are said cash cows, with low startup capital requirements, and can be managed remotely / outsourced.

2/21/13

freeloader:
NorthSider:
TheKing:
To add - this isn't to say that having a little cash cow of your own wouldn't involve a good deal of work, but ideally it'd be something you could manage via outsourcing and remote working. Something that's got huge VC backing will likely mean cranking away like there's no tomorrow. Now, if you can turn your cash cow into something that VCs want to chase, like Patrick explained, that'd be awesome. But, I'm not even sure that it's the ideal life. It would seem, to me, that the ideal is to have a business (or occupation) that pays you enough to keep you comfortable and affords you the freedom to do what you please with your time.

Definitely agree with this sentiment. A small cash cow on the side sounds more ideal than a VC-backed start-up.

This cash cow sounds more like a cash unicorn. I don't of many side gigs that are said cash cows, with low startup capital requirements, and can be managed remotely / outsourced.

1.) You might not realize this, but WSO started as a side business

2.) It's very possible to start a side business that brings in incremental cash. I'm not arguing that it needs to be some monumental venture, but there are definitely things you can do in your off-hours / weekends to get things moving. It's all dependent on how much time and effort you want to put into something. And the amount of money you put into it is entirely dependent on the kind of business it is.

2/21/13

If everyone thought this way, y'all would have no companies to advise on M&A and capital raising

In all seriousness, it really comes down to the person, and the due diligence you've conducted with respect to a potential start-up position. I know of a number of start-ups where junior people who make themselves valuable move up very, very quickly (much more quickly than you would ever see in banking); I know of others where it seems like you're a slave. It's on you to find out as much as you can about the company (it doesn't even need to be in interview Q&A; look at people on LinkedIn and see if they promote from within, if possible).

Also, just thought I'd put this here; it's a pseudo-rebuttal: http://cdixon.org/2013/02/13/the-credentials-trap/

One more thing, I know someone had noted earlier that when working for a start-up, a lot of what you end up doing is moving shit off trucks and arguing with the phone company. That said, if you ever want to start your own company, these are realities you'll have to get used to. I know brilliant, brilliant PM's. Most of them couldn't manage a company out of a paper bag.

Anyway, just a slightly different perspective than the consensus.

Quick Edit: Every concern NS listed is real -- didn't mean in any way to imply that they weren't -- and should be part of any due diligence when looking into start-up roles. All things being equal, it's probably *safer* for the ol' resume (though not necessarily as safe as one might think) to stick with a big company over a tiny start-up.

2/21/13

atomic:
I know brilliant, brilliant PM's. Most of them couldn't manage a company out of a paper bag.
p.

This is what office managers are for, at 50K a year. If you can attract an incremental 2.5mm of assets or get $250K of outperformance, you don't need to answer phones and load trucks.

2/21/13

Great post.

adapt or die:
What would P.T. Barnum say about you?

MY BLOG

2/21/13

nice reading for the evening:)

2/21/13

From personal experience. I work at a startup where I'm paid market rate, no equity and the firm has no vc funding. It's sub $1m in revenue. While the equity piece bugs me, I plan to peace out after a year or two and take what I learned. Granted I will ask for equity after a year, don't know if I'll get it. Plus being in sales it's a you eat what you kill, and I can clear six figures. Talking to friends in the industry .... Breaking six figures is damn near impossible on the business side. Only programmers and sales people can come close.

It's not glamorous either. The founder is awesome, I work 9 to 5 and afterwards dabble on my side projects. The hours are unheard of and we still have double digit growth.

2/22/13

Really great post

2/22/13

I think your article is a very good article for anyone who is scared to take risks. Coming from a startup background myself, I never hired someone to join my startup because they wanted to be rich or make money. The best employees, be it the #1 employee or the #50, are those that believe in what your company is doing. That motivation should match the environment in the office.

Joining a startup should NEVER be for the sole purpose of making more money, especially compared to any IB position.

2/22/13

Agreed. I'm from a startup background aswell, came here to put in my two cents.

From the tone of the comments here, most of you should never join a startup. No start up would take you. Just stay at your aristocratic, high-rise, balls licking jobs on Wall Street and leave Silicon Valley to those who care more about making an impact than making cash.

2/22/13

jericsson09:
Agreed. I'm from a startup background aswell, came here to put in my two cents.

From the tone of the comments here, most of you should never join a startup. No start up would take you. Just stay at your aristocratic, high-rise, balls licking jobs on Wall Street and leave Silicon Valley to those who care more about making an impact than making cash.

God I hope this is a poor trolling attempt.

"For I am a sinner in the hands of an angry God. Bloody Mary full of vodka, blessed are you among cocktails. Pray for me now and at the hour of my death, which I hope is soon. Amen."

2/22/13

I'm currently a cofounder at a vc-backed startup. OP's post is spot on. Don't do a startup unless you are a founder, and even then, it's not as glamorous as you'd might think. Even as a founder, I still feel like I lack freedom. When you get vc-funded you typically lose a great deal control over the direction of the company and product. If I could do this all over again, I'd find a steady job and work on some side lifestyle-project on the side.

2/22/13

Chimpy:
I'm currently a cofounder at a vc-backed startup. OP's post is spot on. Don't do a startup unless you are a founder, and even then, it's not as glamorous as you'd might think. Even as a founder, I still feel like I lack freedom. When you get vc-funded you typically lose a great deal control over the direction of the company and product. If I could do this all over again, I'd find a steady job and work on some side lifestyle-project on the side.

Wow. Very interesting perspective.

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/22/13

Thanks for writing this post. Lots of great advice. I left my job at a VC-backed start-up about 1.5 weeks ago and all of the things above mirrored my experience to a T.

The biggest take-away from this post is to negotiate everything you want up front. If you sign on with the promise of a future pay raise, or equity management will keep finding ways to move the goal post because they want to keep re-investing back into the business. Also, look past the sexy titles and ask yourself what you'll really be doing. Titles may look prestigious to outsiders, but they're meaningless to colleauges at a lean organization.

2/23/13

Great read. Thanks for posting

2/23/13

Great article!

2/23/13

The biggest thing that bothers me about many startups these days, is how people think an iPhone app is a business in of itself.

2/23/13

Banker88:
The biggest thing that bothers me about many start-ups these days, is how people think an iPhone app is a business in of itself.

Your silly. How are app companies that create numerous apps not start ups. Do you know how much coding goes into creating a useful app? Apps are more valuable than the phones now. If your a start-up the can product the next useful apps, that gets thousands of daily downloads and is popularly used, how can you not be considered a start-up.

2/23/13

Interned at a start-up last summer and I saw everything that the OP mentioned/agree with everything he says 100%. Seriously, it appeared to me that unless you are the founder or get an offer for a role that is directly below the founder, then working at a start-up isn't worth it. The place that I worked at had mostly Ivy and comparable graduates working for them and it just seemed like a waste of talent.

2/24/13

I SB'ed this because it's mostly true. It's by design, too - startups benefit from hustling in good talent on the cheap and testing them in hard conditions.

HOWEVER...

The above is written with the caveat that what you are looking for is maximizing the NPV of the career path, and without a differentiating skillset beyond being able to figure things out fast and a willingness to work hard.

I joined a "startup" (in reality a very well funded multi country effort) with no equity and taking a big pay cut, from a "dream job" on a prop trading desk which just wasn't my thing (I thought I had too little experience to have a durable edge). I learned huge amounts in the last year both in terms of soft skills like leadership (and the value of McKinsey and Harvard MBAs) and hard skills like programming. It is definitely worth it. I see it as being paid to go to school, not as employment (and for perspective I am paid 1.3x what we paid our last INSEAD MBA). Once I have enough knowledge and have seen the whole cycle from beginning (when I actually trained the company's first 4 employees on online marketing) to becoming a mid cap corporate (which should happen within a year or two at current growth rate), I will join a few friends and do my own thing. I will have escaped having had to do SEO for some crappy but overfunded iPhone app shop, or yet another "designer T-shirts for half the price" startup that fails to understand the most basic concept of brand.

I gave up hundreds of thousands of dollars in comp and probably millions in NPV, but so far am pretty happy with the choice, because I value NPV less than when I was a college student (or my discount rate is much lower), and freedom both of my hours, my location (travelling all over Asia) and of my work direction much more. The skills I'm learning (like using machine learning to solve business problems) are portable back into finance in a place like Bridgewater in case I want golden chains again.

Also beware of the word "startup". This is the only definition I accept: http://www.paulgraham.com/growth.html Pet shops, and coffee chains, are not startups.

Comp is not necessarily worse, by the way. I know several friends who have taken simple ideas - similar to Ferriss' supplements business - to generating 10k+ USD free cash flow per month per product without much efforts beyond the initial hustling to get the supply chain and demand side set up. Most people are lazy and there are a lot of holes in the economy that can be filled by a smart hard working and flexible guy.

2/25/13

I worked at a bootstrapped startup as the 16th employee and went all the way through IPO. While I agree that most VC funded startups offer no monetary value to employees, I found that the average banker/big company person is not out for it. My company went through banker after banker who knew absolutely nothing about business. Lets face it, a career at a ibank is one big training program. It is a pretty easy way to make money if you can get in. If you take a person that is used to that and throw them into the fire, they don't usually know what to do. I found it pretty easy to progress, but I saw a lot of people get caught up in the myths you mention. Just like 1 in 10 startups fail, 1 in 10 people who switch to startups are cut out for it.

2/25/13

techguy24:
I worked at a bootstrapped startup as the 16th employee and went all the way through IPO. While I agree that most VC funded startups offer no monetary value to employees, I found that the average banker/big company person is not out for it. My company went through banker after banker who knew absolutely nothing about business. Lets face it, a career at a ibank is one big training program. It is a pretty easy way to make money if you can get in. If you take a person that is used to that and throw them into the fire, they don't usually know what to do. I found it pretty easy to progress, but I saw a lot of people get caught up in the myths you mention. Just like 1 in 10 startups fail, 1 in 10 people who switch to startups are cut out for it.

1 in 10 startups succeed*

"For all the tribulations in our lives, for all the troubles that remain in the world, the decline of violence is an accomplishment we can savor, and an impetus to cherish the forces of civilization and enlightenment that made it possible."

2/25/13

AGREE

3/3/13

.

6/7/13

+1 SB, Thanks Man!

"If you have enough assets plus passive income to cover your personal lifestyle expenses for the rest of your life, and that money allows you to work at something you love, without concern for the amount of compensation, then you are wealthy."

1/3/14

Great post! Start ups are so over rated! The chances of someone getting company stock and years later becoming a millionaire are slim to none.

I'm bi-winning. I win here, and I win there.

1/3/14

Great insight

3/17/16

Best way to navigate the tech startup world is to begin your career optimizing your credentials, build your knowledge and network in the high growth sectors within the startup world, and come in at a more senior level with a better comp package. A more direct way to gain credentials is to go work at a hot post Series B tech company -- it already has a ton of traction and momentum, but still cast as the young upstart in the media, so you get the glory without as much risk. Doesn't really make much sense, but neither does credentialism.

Most startups suck. There is a tiny handful of startups every year that are actually worth your time. Figure those out and use your shiny pedigree to make your way in. If it doesn't work out and you really hate the uncertainty, head to business school and reset. If you catch the bug and can't see yourself doing much else, congrats -- you've finally found an actual career and not just another stepping stone.

There is a ton of luck involved in executing on a great startup. There's substantially less luck involved in boostrapping something on the side where you own all or most of the company. Just depends on what you want in life and what concessions you're willing to make to have that.

"Be a yardstick of quality. Some people aren't used to an environment where excellence is expected." - Jobs

3/17/16

Killer post. Thank you for the insights.

3/17/16

Great post. I have a mentor who is pursuing his own startup after banking and VC stints, and he says his goal is to be sure that if they crash and burn, they crash and burn early on, instead of having a slow, drawn out death.

3/17/16

Agreed, but what do you mean "arguably"?! VC over the past decade, with the exception of top decile, has just given returns in line with public market equities, except without the advantage of being liquid. I don't think another Instagram or Tinder clone really adds much value to society, much less would they be good business ideas.

3/17/16

Shit that was a good post. Not to mention, a lot of startups don't materialize as expected - anyone know offhand the failure rate?

3/18/16

I think it's something like 90% of new businesses fail.

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