Jackson Fish Market
Posted on March 11, 2008 by hillel on About, Industry

Working hard or hardly working? VC-backed startups vs. Bootstraps.

There’s been a blip in the blogosphere (and the Seattle Tech Startup mailing list) lately about corporate culture and how hard people should work at startups. Posts of note include:

We’ve taken our own approach here… (not super noteworthy yet as there are only 3 of us relative to the “mega-corporations” of 37 Signals and Mahalo ;) ) but we have done it twice already successfully — we take two “breaks” a year for roughly 4 weeks at a time (last year summer and winter). During those periods we shut the company down and respond only to emergencies and customer issues. For the most part though people travel out of the country, do big projects at home, etc. We considered the 4 day workweeks but decided that to get some really good non-work stuff done you need more than a week or two at a time. Also, not having everyone else working while you’re on your trip around the world makes it easier to relax we’ve found.

But… that’s not the main point of this post.

Across the net people have come in one side or another of this debate. Clearly being flexible with your employees and making sure they have time to have a life makes sense. Clearly not hiring slackers or people who don’t love their job makes sense as well (though I would ask Calacanis, why does he write it as “fire” as opposed to “not hire in the first place” — but that’s another post). But I have noticed (in an ad-hoc fashion) that the companies that talk about scaling back from “seven days a week to six” are often funded by angel and VC money. And the companies that have a more liberal attitude about time spent at work are not part of that funding model.

My take is this: VC money comes with a countdown. At a certain point the fund ends. At a certain point the investors need to see return. At a certain point there’s a deadline for progress past which it’s no longer worth it to spend any more time or money on a particular startup. When you start a company with an hourglass, it’s no wonder startup CEOs feel the need to work six and seven days a week. The’re battling the clock. “It’s in the DNA” as Umair Haque would say.

I know the knee-jerk response to the above paragraph from a few folks (my responses in-line):

  • “So you don’t care about making money?” — Of course we do.
  • “So VCs shouldn’t expect a return on their money in a reasonable timeframe?” — Of course they should.
  • “So you want to spend your entire career taking time off instead of making a successful business?” — Can’t I do both?

I don’t know about other folks trying to create businesses, but I am under no illusion that I have any predictive power in terms of when we’ll reach certain revenue milestones. I can guess. I can make educated guesses. I can even make spreadsheets and presentations that look like I really know what the fuck I’m talking about. But I don’t. And I believe nobody else does either. When you’re starting a new business, there’s simply no way to know. You can guess, but I’m not sure what that gets you other than a false sense of comfort. (For more on this check out my favorite post from Marc Andreesen from a while ago… basically, you can’t raise your batting average so increase your number of at bats.)

So, for me at least, this means that we would be insane to start a business with a built-in self-destruct timer given that we have no idea how long it will take to make the business a success. I’m a relatively risk-averse person and this seems to me the equivalent of startup suicide. And, yes, I know many businesses have successfully beaten the clock, but many more businesses (some started by the very same people) have not.

And in fact, when you take that investment, not only is your VC and your business on the clock, but you end up putting yourself and your employees on the clock. Regardless of what the founders say, I think it’s hard as the leader of a VC funded startup to not start thinking about an exit. (The VCs are thinking about it.) When you’re running a business the values of the leadership have to align. When you take investment there is some aligning of the values of the leadership of the company and the new owners of the company. I believe that invariably, on the issue of timing, the leadership of the company ends up aligning their values with the investors. Cause… who could argue with wanting to be successful in a reasonable time frame? So let’s act like we have a better than average ability to effect that outcome! (Oh wait, we don’t… shhhhhhhhhhhhhhh.)

And once the leadership is on the clock, it’s a short hop, skip, and a jump to put the rest of the employees on the clock. (Never mind that the upside for most of the employees is very very different from the leadership and investors — more on this in a later post.) Of course this is simply not a recipe for the long term. Ask any runner (and I’ve had to since I’m allergic to most exercise) and they’ll talk to you about pacing yourself for a long distance run. Most VC-backed startups I learn about are sprinting.

This is not to say that taking venture is necessarily bad, or that VCs don’t understand that businesses take time, or that every venture-backed startup necessarily behaves this way. But, I do believe the DNA in the VC backed startup is conducive to this type of short term thinking. And of course, when you’re facing a deadly snake (hmm… who has the new Indy movie on the brain?) or some other life-threatening situation, short-term thinking can come in quite handy. But running your business this way wears on the employees. To borrow a term from the environmental sphere, what we’re looking for is sustainability. You can’t overfish the seas (the fish need time to replenish their population), you can’t overplant a certain crop (farmers do crop rotation), you can’t use up all the natural resources of the planet, and you can’t look at your employees as having a short shelf-life. It’s not like there’s tons more just waiting to replace the ones you’re burning through.

Finding fantastic people is very very hard. In general when you find someone who is just perfect (smart, talented, energetic, fun to hang out with, etc.) wouldn’t you want to stay working with that person for as long as possible? The cost of replacing them is huge. Of course 37 Signals and Mahalo both get this fact and are taking the approach they think best to retaining their best folks. I just think, making the right decision comes more naturally when the pressure to succeed comes primarily from a group of talented folks who want to create value and prove themselves, and not from people who’s top priority is a return on their investment.

And finally, the pressure relief works in both directions. When a company is filled with people working hard to get their exit so they can retire and do the things they really love, everyone is feeling the pressure. When you give people the time to do the things they love in addition to work (let’s not be so cynical as to assume people have a limited capacity for being passionate about things in their lives) then when they are working, they can work even harder. Not because they feel time ticking away, but because time has slowed down. They no longer have to wait until they “hit the lottery” to do the things they love in addition to their work — they can do them on Friday (at 37 signals) or in their next month break (here at JFM). Having the time “now” to fit a broad range of things into your life does wonders for the degree with which you apply yourself to work you love. Truly passionate people don’t confine their excitement to great work, they need time to follow their passions year round.

Update: More thoughts from Alex at Launch 21.

Join the discussion 9 Comments

  • Reply

    Cubicle Dropout

    March 12, 2008 at 11:40 am

    Good Post. I plan on bootstrapping a startup in the near future for the express purpose of better time management. Productivity among passionate workers doesn’t necessarily follow a 9-5 work schedule, and just because someone shows up for a 9-5 job doesn’t mean they’re working 9-5.

  • Reply

    Matt

    March 13, 2008 at 11:14 pm

    Great post. I’m a co-founder at a bootstrapped startup (quit the consulting world about 6 months ago) and it’s a real eye opening experience.

    Building products was my passion, I just needed to start actually doing it and really diving into the work to fully realize it.

    With bootstrapping, I think the biggest advantage upfront is control. A lot of things will change and having a dynamic team that can shift, re-focus, and deliver productively and with real passion is important.

  • Reply

    Jeff Yablon

    March 14, 2008 at 6:36 am

    Bravo!

    Take it in another direction: when people got a job and worked for a benevolent (ha!) company for long stretches, perhaps their entire working lives, there was a set of rules that was really easy to interpret: you showed up when expected and did was was asked if you desired to keep your “place”. We live in a different world, now:

    Many experts in this field will tell you that there’s no such thing as a job anymore; even those of us “lucky” enough to be on someone’s payroll are really just self-employed people, albeit with a regular check. Well, if that’s true (and I posit that it is), then we all (and I’m an emploYER, thank you) need to accept the reality that high-handed statements like Jason’s have no place in the equation.

    Most important: we all NEED downtime. Pick a study, any study; they all say the same thing. ANd be honest; did you even need a study to tell you that?

    Jeff Yablon
    President & CEO
    PC VIP Inc.
    Virtual VIP

  • Reply

    Work Post

    March 14, 2008 at 7:17 am

    Most of the investors and businessmen my company has talked to say the same thing: until your idea is at least partially realized and you have “customers”, a reliable revenue stream and a good management team in place, the VCs you want to work with will not have much interest in you. So I guess that means you have to do what you have to do to get those things before you can (and should) accept funding. And once you do accept funding, the pressure to show results increases. Bottom line, startups are time consuming and you will tend to become obsessed if you start one but the best people I have observed who start their own companies work smarter than everyone else, not harder.

  • Reply

    Tony Wright

    March 14, 2008 at 9:54 am

    Huh? Bootstrapping has a “self-destruct” timer too. Everyone has a tolerance for how much they are willing to watch their savings dwindle (or stagnate) when they know there are 6-figure jobs out there waiting for ’em.

    Unless you are a services/hybrid business like Jackson Fish (you guys do consulting/project work for MS, don’t you?), you chance of getting a healthy salary early on is slim.

    While you can adjust your spending to increase your runway– bootstrapping is essentially being your own VC. You are investing savings and/or opportunity cost in your idea/business.

    This is true for ANY product business and is even more poignant for strict consumer plays (that don’t have a paid offering). It’s a long road with a painful cliff at the end unless you can manage to sprout wings before you get there.

    All that being said, I think you are right on a lot of fronts. By virtue of the business I’ve created, I have very very good data to support that working 10 days straight kills productivity. Someday I’ll aggregate and publish some data to prove it. :-)

    Great/interesting post– thanks!

  • Reply

    Hillel

    March 14, 2008 at 10:08 am

    @Tony. Thanks for all the comments. wrt bootstrapping self-destruct… I guess I always understood bootstrapping to mean you need to identify a source of revenue (other than your savings) from day one, and are constrained by that revenue. It may be a temporary source (relative to your long range business model) – like our consulting efforts (we do for MSFT, YHOO, and other startups btw) but it’s still a revenue source (as opposed to just savings).

    I don’t think of self-funded startups as bootstraps per se. Though I’ll confess that most bootstraps probably have some degree of self-funding even if it’s only subsidizing the venture by taking less salary (which we are certainly doing).

    Maybe this is just semantics. :)

    BTW… i’ll definitely check out rescuetime.com. It looks great.

  • Reply

    Vijay Chakravarthy

    March 14, 2008 at 1:34 pm

    I think there is another dimension to this that many people are not aware of.

    In any system, say for example, one that produces good software, there are bound to be bottlenecks at any specific point in time. For example, you would be bottlenecked on a few engineers, or on product management etc. At such points, it is far better for the non-bottlenecked people to take it easy, go learn a few skills (to alleviate the bottleneck), etc. than to work hard and overload the system.

    This understanding, is in essence, an approach that measures results and throughput rather than number of hours spent working.
    Which is not something many organizations are comfortable with, since they dont have those measurements in place, and so have to rely on, IMHO, the completely ad-hoc measure of watching how subordinates spend their time..

  • Reply

    Hillel

    March 14, 2008 at 3:11 pm

    @Vijay: You’ve touched on a super important point. In fact, I think it’s worthy of another post. Basically, companies would rather base decisions on things they can measure even if they are the wrong things versus admitting that there is no measurable metric and going with what seems right.

    The other key of course is that companies that feel that they need to measure how subordinates spend their time is starting from the perspective that their employees are children who can’t be trusted as opposed to adults who are naturally inclined to do the right thing. This too is another post I think.

    Thanks to everyone for the comments.

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