Agile VC: 

My idle thoughts on tech startups

Playing Startup

Lee Hower
June 17, 2015 · 5  min.

playtimeI’ve observed what may be an emerging trend, at least in some startups, that I find somewhat unsettling.  It has an impact at an individual level, a company level, and an ecosystem level.  This is not an easy topic to discuss without coming off like a jerk or a crusty old dude, so I wanted to share two quick stories about my own career below.  But I think it’s important to discuss, particularly given today’s heady environment for startups.

My first startup job was as an early employee at PayPal, where I took a job at the end of ‘1999 and started a few months later in 2000.  When I first started working there, I only made it home for dinner with my cohabiting girlfriend (now wife) probably 3-5 times a month.  I worked, usually at the office not remotely, at least part of every weekend for the first year or so.

I started off as a product manager and while I never actually slept over at the office, there were frequently late nights.  One of my fellow PMs did sleep  routinely under his desk in a sleeping bag he kept there for that purpose.  On multiple occasions I’d get in to the office in the morning and find our CEO (Elon Musk at the time) asleep on the couch in our little product team lounge from the night before.  The company held holiday parties at the end of each year and lots of friendships were spawned from work collaborations.  But the first real time we had a big celebration and folks felt like we’d “made it” was the party we held in the parking lot on February 14, 2002 when PayPal went public.  We were a profitable company at that point with nearly $200M annualized revenue, one of the first tech companies to IPO after the dot-com bubble.

When we started LinkedIn, it was a similar situation.  As a founding team we were a reasonably experienced and close-knit group already.  Nearly all of us had worked with Reid Hoffman at either PayPal or SocialNet before so there was zero concept of “face time” or having to establish trust or work ethic with one another.  We started working nights and weekends in late 2002 when some of the founding team were wrapping up their prior day jobs and then everybody was full time on LinkedIn by January 2003.  Yet absent a family obligation or something similar, nobody left until 7, 8, 9pm, or later even though we were too cheap to provide dinner for employees back then in the early days.

My point and the trend I’ve noticed and felt we should start discussing more publicly:  I fear a meaningful number of people are “playing startup” today.

Paul Graham used this phrase in an essay, albeit making a slightly different point.  What I mean is that people are joining startups because working in a startup seems cool or lucrative, not because they want to change the world and they’re fundamentally committed to putting in all the blood, sweat, and tears that entails.  We’re hearing more about people new to startups asking their seed stage company how many months of severance is included in their package.  We see co-working spaces where the ratio of work to non-work (ping pong, beer, startup talks, etc) is pretty low, while elsewhere founders enamored with the lifestyle or perception of being an entrepreneur, believing they’ve made it once their company raises a Series B.  Entire startups exude a rah-rah environment during the all hands, and then at 5:15pm the office is a ghost town (even though everybody rolled in after 10am).

FWIW I do firmly believe that everyone deserves and should work towards finding work + life harmony as Brad Feld has described it.  The reality is a startup career path entails a variety of sacrifices, but I don’t believe it should preclude a rich family life, involvement in one’s community, or otherwise seeking a well-rounded human existence.  And even when working hard, there should always be moments of fun and close relationships that are formed from working in startups.  Back in the early PayPal days Jeremy Stoppelman and I used to go hit golf balls during lunchtime at the Palo Alto muni driving range across the street from our office on Embarcadero Rd, which was a nice break in a long day and helped form a long-lasting friendship.

Additionally, a lot of people today work in startups or want to work in startups or want to be founders, which overall is a great thing.  A lot more companies get started today than 10 or 20 years ago, which overall is a great thing.  And a lot of big, meaningful companies have been created just in the last couple years which is nearly unprecedented.

But I’ve witnessed more and more “playing startup” in recent months.  And to be clear I split my time between Boston, New York, and SF and I’ve seen this across a broad swath of startups and individuals… both outside NextView’s portfolio and occasionally within it.

So why should I or we collectively care?  Because while lots of startups will fail in spite of the hard work and zealous commitment of the whole team, pretty much none succeed without it.

I’d like to think that I worked hard, but I was probably in the middle of the distribution of my colleagues at both PayPal and LinkedIn in terms of work ethic… neither the slacker nor the hardest worker.  More important than simply hours worked though, I perceived a zeal in my colleagues that translated into an overwhelming commitment in each of them to do whatever they could to incrementally drive our company closer to success.  It motivated me to do the same.  In addition we all realized that failure is always an option, success is hard won, and recognized the difference between progress towards a goal and achievement of that goal.  So we acted accordingly.

I don’t always see that today unfortunately.  At times I see of sense of entitlement when perhaps it’s not merited.  I see a lack of commitment and hard work, especially when the work isn’t fun but is still of critical importance.   I see people taking their eye off the ball when it’s still in midair or worse, not having a clue which of the juggling balls actually matter.

To be clear I don’t want to paint all employees, founders, and startups with a broad brush.  I still think most of the startup ecosystem has a healthy attitude, focus, and commitment to the unique challenges of throwing yourself off a cliff and assembling an airplane on the way down (as Reid describes the startup experience).  A few months back I saw a founder/CEO with nearly all of his ~100 person SaaS company hard at work, closing their final deal of 2014 at 11:00pm New Years Eve.  Last fall I saw a startup with it’s back against the wall, days from shutting down, pull off a new financing round and what looks to be a promising pivot.  And just the other weekend I bumped into a founder hard at work on a Sunday afternoon when I stopped by my office building.  I still see lots of things which give me reassurance even as I see some things that give me serious concern.

Perhaps it’s just a symptom of where we are in the cycle.  But there’s still a lot of “playing startup” going on.  I commit myself to help however I can to foster and support the true commitment of entrepreneurship in my small corner of the startup world.  But let’s start the dialogue of what we do from here.

Lee Hower
Lee is a co-founder and Partner at NextView Ventures. He has spent his entire career as an entrepreneur and investor in early-stage software and internet startups.