Author Archives: Jason Evanish

I'm a coach and consultant for early stage SaaS startups. I help VPs of Product, Heads of Product, and 1st PMs with their toughest challenges like churn, team turnover, stakeholder challenges, issues with consistently shipping great features consistently, and more. I also started Lighthouse, which helps you learn to be a better manager through our blog, podcast, and training. When not working, I'm an avid reader, athlete, and enjoy lake life living in Austin, Texas.

3 Questions Brought About by Steve Jobs’s Life

5 October 2011

Everyone is tweeting and writing their thoughts as a legend has now passed. I just re-watched Jobs’s Stanford Commencement speech (embedded below) and was as inspired as ever.  As I read more of the tributes like Walt Mossberg’s personal recollection, it got me thinking about 3 heavy questions around all of this:

1) Steve says to “have the courage to follow your heart and intuition,” but why do so few actually have it?

I know so many people that somehow got into a rut at one point and are just on a heartless journey, living paycheck to paycheck at a job they care little about.  I wish for a world with more passionate and inspired people.

2) Would you rather live 56 years in the life of Steve Jobs or 85 years of average American life?

If the cost of changing the world is 1/3rd of your life, that’s actually a pretty high price; there is no commodity more priceless than time.

3) What if Steve’s mother had an abortion instead of putting him up for adoption?

As Steve mentions in his speech, his mother had him out of wedlock and put him up for adoption.  There are few decisions harder in life than the one Steve’s mother faced. The world is fortunate for her decision.

As Walt Mossberg said in his opening, “He was a historical figure on the scale of a Thomas Edison or Henry Ford and set the mold for many other corporate leaders in many other industries.” Only a man as great as Steve could bring about so many great thoughts and so many deep things to think about.

Why I’m Starting a Company Now

10 August 2011

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As I’ve been out on this journey to start a company for a couple of months now, I’ve had plenty of time to reflect on why I’m starting a company now.  From my perspective it’s really the only choice that makes sense for me. The last few years of my life have been filled with preparation for this. Here’s why:

1) I have a zen financial outlook

– I have a sizeable warchest saved up that means I don’t need a salary for quite some time (a year +).  An incremental salary increase is not appealing to me; I have few wants/needs in life and don’t see it changing for the foreseeable future. One day, I’ll probably have a wife, kids and mortgage. That day, it will be a lot harder to bet it all on starting a company.

2) Customer development, homes

– For over a year at oneforty, I was eating, sleeping and breathing customer development. Before that, I did some consulting for John Prendergast cutting my teeth and learning from one of our local experts. I’ve since mentored at Lean Startup Machine events in NYC and Boston and wrote numerous posts about the topic (nothing helps you understand what you know like teaching/helping others).  All this adds up to making me feel like I’m the Kathy Griffin of CustDev (aka- I’m on the D List : P).

– I’m ready to take this knowledge and understanding and use it to crush a startup.  I’ve already used it to kill 4 ideas that have come up and am continuing the learning process, leveraging the knowledge of the greats in custdev (like @hnshah, @brantcooper and @pv).

– Any company I launch will be forged in the pits of lean startup-dom, which is much easier than bringing it into an existing company.  A wise friend recently said, “Culture is like concrete in that it hardens and is hard to change later.” That includes being a customer-centric company.

3) I’m going to be a recruiting machine

– One of my favorite things about being Greenhorn is the opportunity to sit at the intersection of so much cool stuff in our ecosystem. As part of sitting at this intersection, I hear from people that are unhappy at their current jobs or just ready for a change, companies that are waffling and what companies are growing or shrinking. All of these are huge opportunities as we all know that often the best talent never goes officially “on the market.”  Thus far, I’ve mainly been referring those people to friends’s startups, but I’m looking forward to the day I can talk to them about my startup and bring them in for an interview as well.

– All of this doesn’t even consider the platform I have with GreenhornConnect.com and beyond to reach a wide audience, not unlike Dharmesh is able to use OnStartups (although obviously at a much, much smaller scale than him).

4) It’s who you know…

– To be clear, I have yet to accomplish anything significant.  However, as Mark Suster and many others talk about dots and lines in determining investment (which means showing progress over time to build confidence in others investing in you), I’ve already made a few lines thanks to Greenhorn Connect and other activities in our community. This makes me less of an unknown when I reach out for advice, introductions or investment. I’ll still need to prove it with the startup I work on, but it certainly helps.

– While I’ve been meeting and talking with many of the awesome people in our community, I’ve also been curating a list to understand what everyone is an expert in. When someone says, “Let me know how I can help,” I always come back now with, “Ok, what are you best at? What the best thing I should ask you for help with?” I’m noting what they say so I can leverage their offers the best way possible. I can’t wait to leverage this as my startup needs help in everything from leadership to technical questions, customer development to culture and beyond.

5) Greenhorn is a mini-startup

– Few investors see a lot of value in the experience I’ve had in building GHC or from similar side projects according to friends I know (they just respect the traffic and influence) but most entrepreneurs seem to understand the value of learning on the fly from it. Similar to how Dharmesh experiments with OnStartups, GHC is my little playground.

– I’ve hired and fired, managed a paper-thin budget, found 6 unique revenue streams and learned a little project management along the way.  All of this with only a fraction of my attention for the majority of the time Greenhorn Connect has existed.  I am anxious to leverage the learnings on a full scale startup and continue to use it as a low-risk avenue to perform experiments.

6) The skills I have are for a founder, not an employee

– Early employees and founders need to be athletes. They need to be able to handle any job and roll with the punches that come with an early startup struggling to find product-market fit.  It helps as an employee to have a specialty that you can then grow into as the company hires more people and everyone gets more specialized.

– In my case, customer development is what I developed as a specialized skill.  One of the things I learned at the startup I worked at was that a founder needs to own customer development; the person doing customer development is the line of sight to the customer and it’s impossible to relay that perfectly to a management team (although I tried with detailed notes, summaries, email wrap ups, meetings, etc).

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It’s never been a better time to be a young entrepreneur and I’m not that young (26). I feel like I have a combination of plenty of chips to bet and a through-the-roof risk tolerance right now. You are who you surround yourself with and most of my friends are founders or really early employees, so it only makes me more excited to be a founder as well.


Technical and working on something cool that you’d like some business help with? Drop me an email at evanish.j[at]gmail[dot]com and let’s talk. 

Fall Accelerator in Boston?

13 July 2011

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I’ve been helping a friend with his startup recently who shows a lot of promise: early (paying) customers, solid key elements of a product and a logical business model he’s validating.  He’s in a perfect position to join an accelerator and take his company to the next level. The combination of great mentors, a structured program to plan and move the business forward and modest financing represent the things he needs most right now.

Unfortunately, every accelerator program is done this year or currently going on. In fact, unless he had applied by May, he’d have been out of luck for all of 2011.

We have a number of great programs already in place, but they’re all in the spring and summer:

Spring: TechStars

Summer: MassChallenge, Summer at Highland, BetaSpring (Providence)

…but nothing for the Fall or Winter.

This leads me to a few questions:

What would you tell someone in his situation?

Can Boston add another accelerator?

Would TechStars go twice a year like it has in NYC?

Independence Day & Quicksand

4 July 2011

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On this long weekend celebrating our country’s independence, I’ve had the opportunity to reflect on the past couple of months since I left oneforty to work on my own startup.  It’s been good to reconnect with a lot of people who I didn’t get to while being heads down at oneforty, recharge my batteries a bit, and have some success in the cofounder search. That being said, I’ve also realized I’ve walked into quicksand…

Quicksand.

On the football field, it’s when one thing after another goes wrong despite trying to make plays. In startups, it’s when you let something paralyze you and sink your entrepreneurial efforts. It might be because you focus too much on the wrong thing or ignore the most important thing.

I have tried to plan so many parts of this startup I’m now working on. Whether it be meticulously noting the learnings of the past year at oneforty, saving money so I can go without a salary for a very long period of time, or mapping out all of my contacts and the best ways to leverage them to succeed, everything has been carefully calculated.  I even focused on finding a great tech cofounder before the idea, so I was sure I had good alignment with them before we started running on an idea. All of this though ignores a key element: the idea. It is in this search for the idea that I’ve found myself in quicksand.

Searching for Inspiration.

Being calculated and focused is great for planning to save money and preparing to launch a company, but it’s terrible for trying to generate an idea. You can’t force inspiration.  I know this not for lack of trying:

  • Tried using David Skok’s brainstorming process he blogged about (coincidentally posted my first day after leaving oneforty).  It just left me feeling like a VC; knowing what are good, interesting industries, but not actually feeling like there was a specific idea to go work on.
  • Brainstorming with friends. I hit the white board with friends trying to flesh out some ideas, but only managed to write off a few ideas and failed in trying to dig deeper on ideas identified by using David Skok’s aforementioned process.
  • Talking with friends about the industries of their startups. I talked with a lot of friends in the community about what they were working on to see if any industries caught my eye.  Nothing seemed to spark.
  • Helping friends with their startups.  I tried helping a couple friends with their startups to see if I liked what they were doing (and might join them) or if their industries seemed like it had any interesting problems to solve.  The first two attempts yielded nothing and the verdict is still out on the 3rd.
I’ve found the harder I’ve tried to come up with the idea, the more I’ve sunk.

The Paradox of Choice

I feel a tremendous amount of pressure to come up with an incredible idea. A friend of mine mentioned over coffee that he hopes I don’t become Jarrod Saltalamacchia and it fits how I feel; Jarrod was a hugely touted prospect that came up from the minors and everyone expected he’d be the next great major league catcher.  As it turned out, he’s ended up being more of a journeyman.

I feel like I have to get a big hit in my first at bat and it has crippled me; everything feels like a non-starter because no idea feels “good enough.”  It’s also hard because the closest focus I’ve found is that I know I want to build a B2B SAAS company (mainly because I feel there is the most support and related companies here and I understand B2B more than consumer web.)

Digging Out

Realizing this is happening and admitting it feels like the first step. More importantly is what happens next.

David Cancel gave me great advice at RubyRiot that I haven’t heeded well to this point. He said, “save someone an hour a day and build a business around that.”  It also harkens back to the most obvious solution that’s been standing right in front of me the entire time: Customer Development.  Somehow, in all of this, I’ve done very little customer development (other than when helping friends’ startups).

What Now?

As a recent blog post said, “A lot of people talk about Lean Startups and customer development, but very few people really do it.” I need to get outside the f@&%ing building.

Here’s how you can help:

1) What sucks in your day to day or someone you know?

What makes you complain or you’ve heard someone say is horribly inefficient, and totally not in Web 2.0 and should be? I want to talk to you and/or them! Seriously, even if we don’t know each other, drop me an email at evanish.j [at] gmail [dot] com and tell me about your problem.

Don’t worry if you think it’s a boring problem; I in fact prefer unsexy problems. I’m hoping to solve a problem that doesn’t have 25 Valley startups working on it.  One of my favorite startups a friend is doing (not in Boston) is working in a space where his direct competitors are…call centers. That’s a fun problem to solve.

2) Got an idea you wish existed but can’t work on?

I’ve already talked to a few of you that have shared ideas where you said, “If I wasn’t doing my startup, I would do this.”  If you find yourself saying that, I’d love to buy you a coffee or beer and see if it’s something I can help make a reality.  I’m very happy to make you a beta user ;- )

3) Hold me to this.

Whether you have a problem or know of one I can solve or not, please hold me to this.

Don’t ask me how I’m doing next time you see me. Ask me if I’ve gotten outside the building.

Motivation and Perspective

26 June 2011

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In life, you face ups and downs constantly. Choosing to be an entrepreneur means you live in a world of extremes much greater than those with the security of a 9 to 5.  Especially as a young entrepreneur who has a much simpler personal life than those with wife/kids/families, I live and die by startup life; the swings are magnified because so much of it personifies my life and determines how I measure myself.

One of the luxuries of running Greenhorn Connect is that I’ve always had it in addition to whatever my main focus was (for the last year – oneforty and now the new startup).  I’ve found that in most cases, there would be at least one victory, one good thing that always happened to focus on despite any setbacks or blows I’d also taken.

In the end though, some days I still feel more like the nail than the hammer. On these days and ones where I just want to get amped up, I turn to some key places of inspiration.

I love movies. I feel like a good filmmaker with the right story and actors can create a connection with the audience in a genuine way unlike any other medium. I also love sports.  There is no better microcosm for life. Every game and every season mirrors so many of the struggles (and triumphs) of life. It should then be no surprise that all of these are sports and film related.

The “Suck it up” Speech – Rocky Balboa

Rocky’s Speech to his son on Life & Fighting

I watch this when I need to remember that life isn’t easy, and that “90% of life is just showing up” because the other guy will give up.

The Reason to Fight so Hard – Any Given Sunday

Al Pacino’s “inches” speech

Nothing better captures the essence of the struggle and how those little victories, and all the day to day efforts are what builds success.

Hope & Spirit – The Shawshank Redemption

Andy and Red share in the excitement and challenges of hope.

In the end, all we have is our own spirit. If you listen to it, you will get there. This is my all time favorite movie and my goto film when I really need picked up.

Remembering Greatness – Compilation of MJ Interviews

From Nike ads to long hours on the baseball field and courts, a view into MJ’s life.

Your greatest competitor is yourself, but that is how you create greatness: by demanding it of yourself and putting in the work to get there.

Drive, Passion and Dying on the Treadmill – Compilation of Will Smith Interviews

This video made me a fan of Will Smith for life and never doubt another film he’s a part of.

I love Will’s line, “If we got on a treadmill together, there’s 2 things: You’re getting off first, or I’m going to die.” You either find this disturbing or you understand me.

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It feels like my life can be summed up in one word: escalation. I’m always trying to make the next step greater than the last, the next day better than the previous.

One night, shortly after starting at oneforty, Laura Fitton tweeted asking, “What’s the one most important thing?”  I answered “Progress.” Escalation is positive progress.

When I feel like progress is backwards or I just need a reminder of what drives me, this is what I turn to.  This is what I’m about.

Competition and Inspiration: Environmental Effects of Nantucket and Beyond

19 June 2011

When I was a freshman in high school, my father and I attended the Cumberland Valley High School Track and Field banquet. It was an annual event to celebrate the end of another track season by looking back on the season, recognizing great contributors to the team and providing the coaches an opportunity to send off seniors and talk about plans for the future.

My freshman year, I was far from good. I barely made the team that traveled to away meets (they only took the top 5 for each event).  I only ran track that season because soccer hadn’t worked out in the fall and my parents wanted me to try another sport.  It helped that my father ran track when he was in college, which made me think I’d automatically be good at it. I was wrong.

It was a good enough season for a freshman as I enjoyed personal victories fending off challenges for that last spot for away meets and taking 25 seconds off my time (2:40 to 2:15).  However, in the grand scheme of things, no one but my parents and I noticed these “victories.”

At the banquet, our coach reflected on the conference championship we had won and the top athletes on the team that were returning the following year.  I watched from my seat as I felt envy for the high regard the top runners were given. I realized that for all the accomplishments I thought I’d had that season, they were really empty; I hadn’t scored a single point for the team and wasn’t even on the coaches radar as an “up and coming” runner.

As I was leaving the banquet, my long distance coach asked me if I would run cross country in the fall. He told me it would help make me a better runner for the next track season.  I agreed.

As I got in the car with my father to head home, I told him I was going to train all summer and do whatever it took to make varsity for Cross Country.  My father was supportive, but reminded that varsity meant one of the top 7 runners at the school. I had just finished a season where I was barely the 7th best runner on the team in one of a dozen different race lengths.

That summer, I ran over 620 miles in 3 months.  I built up to running 10 miles a day. Every day, my father would wake me up when he went to work and I would run 7.5 miles. An hour after dinner at night, I’d run 2.5 miles more.  During those 3 months, my mile pace went from 8:30 per mile for the 7.5 mile run down to 6:30 per mile for the 7.5 mile run.

To everyone’s surprise, I showed up in great shape at the start of the season and made the last varsity spot.  The hard work had paid off and now I was mentioned as an “up and coming” runner and had the respect of my peers. From there the work was just beginning, but I had made the leap necessary to work alongside the top athletes and take the steps necessary to eventually captain the Cross Country team my senior year.

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Going to the Nantucket Conference last weekend felt like the Track and Field Banquet all over again.  Greenhorn Connect got me in the door, but it felt similar to just making the away squad to run the 800 meters; I’m as much a rookie (if not more so) as the other sponsored young entrepreneurs that attended.

Sitting here at the genesis stage of my next startup, I can’t help but feel the pressure to do something big and find a way to raise my game to hopefully work to one day be an equal of the more distinguished Nantucket attendees.  I have every intention of working just as hard on my next venture as I did that summer to make the varsity cross country team.

My thoughts on #BetterMA: How to Retain Gen Y

8 June 2011

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Yesterday was the “Cultivating Talent: A Building a Better Commonwealth Forum” at the beautifully restored Paramount Center. The goal of the event was to discuss how Massachusetts can better engage and retain Generation Y. While I was expecting a lot of rhetoric and empty conversation, I was pleasantly surprised that the majority of the event had very productive discussion and moved past stereotypes and un-actionable obstacles (sorry, the weather isn’t changing and neither are T hours).

Attendees were encouraged to share their ideas after the event via their blogs, so I’d like to share a few of my thoughts:

Give the “Stay Here” program a facelift.

During audience Q&A, I asked Governor Patrick about the program and suggested they get a better name ASAP.  As a Gen Y’er there are few things less appealing than the command, “Stay.”  We’re an aspirational group and like to think that we’re all blazing our own trails.   Phrases like “Stay Here” run counter to that as it feels like our parents asking us not to go or just a group begging us to do something we’re not interested in (one tongue-in-cheek audience member proposed the change, “baby, don’t go!”).

So what’s the solution? (as the Governor rightly put me on the spot for my suggestion)

I like “Grow Here”, but “Develop Here”, “Be Here” and “Build Here” all work too (note: because of the overarching Mass, It’s All Here program, it has to end in “Here”). The key to me is that the phrase should be inviting and encouraging; I want to know there’s a great party going on and I’d be a fool to miss it. I would also like to know that you understand Gen Y and know that graduating college is just the first step in a career filled with growth and opportunity.  “Stay here” feels like that needy girlfriend you dumped when you went to college. “Grow here” and “Be here” feels like that experience you had at that awesome party you found on the second day in college and never seemed to truly leave.

The Simplest Solution – Give Us Fulfilling Jobs.

Diane did a great job in pulling the panel back from a downward spiral into the same, unlikely-to-be-fixed issues that have plagued many similar events – T and bar hours, cultural complaints and high cost of housing.  She reminded everyone that young people regularly happily cram themselves like sardines into tiny, overpriced apartments in NYC.  If we’re happy with our work and our immediate environment, we’ll happily make sacrifices in other areas.

As reported recently in the New York Times, “the unemployment rate for 16- to 24-year-olds is a whopping 17.6 percent.” If you included the number of people who have jobs unrelated to their majors, but are waiting tables or doing temp work, the number would grow even larger.  I refuse to believe that 1 in 5 (or more) of my fellow Gen Y members is a total unemployable loser.  The fastest way to retain our local graduates is to give them challenging, interesting jobs.

We have to find a way for these better opportunities to be as visible to students as those stuffy, entry level, soul-sucking jobs at finance companies and other conglomo-corp type companies. As I wrote in my contribution to Kirsner’s Globe piece…we need to Go to Them!

Smaller, more interesting companies obviously have less bandwidth, but that just means you need to get creative.  Leverage your existing staff to start with the schools they went to; they’re likely to know how to get around some of the dead ends in the schools career services department; even Northaestern, (where I went) #1 in job placement after graduation, has an ineffective career services department…it’s the co-op program that gets everyone their jobs. So also think about getting an intern or two. They’ll be cheap and a great way to test a young person’s talent before you invest in a full time offer.

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There is great complexity in the challenge of motivating and retaining an entire generation. These are just 2 areas I think we can immediately improve.

How would you improve things for Gen Y in Massachusetts?

Leadership Lessons First Time Entrepreneurs Forget

7 June 2011

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While building Greenhorn Connect, I’ve spent a great deal of my time with young and first time entrepreneurs.  If there’s one thing I’ve come to appreciate, it’s the absurd odds stacked against any of us succeeding; there’s just so much that you have no idea about and need to quickly learn.

You could spend years learning just one small subsection of your duties like SEO, analytics, customer development, copywriting, design, fundraising, product development, development architecture or simply great coding, but the demands of startups says you need to become competent and relatively adept at all of those and more.  Amongst all those hard skills, I didn’t even mention leadership, which I think is the most underrated skill to develop as a young entrepreneur.

Leadership is a bit different, because it’s a soft skill; it’s not as easy to measure as the success of your marketing campaign or the elegance and functionality of your code.  However, it’s an immensely important skill and one with more long term value than becoming an expert in any one of the aforementioned hard skill areas; if your goal is to build a company with more than yourself as an employee, then you’re going to be leading others.  As you grow, you’ll be leading more people and spending less time on any of the individual skills you used in the early days and much more on communication, vision and goal setting and coordination across teams.

As I’ve learned through my own errors and in talking to other young entrepreneurs, I’ve noticed there are 2 major concepts most of us don’t recognize that are absolutely critical to leading your team even when you only have one or two employees:

1) Your employees don’t work for you; You serve them.

Having employees means that you’ve been able to convince others to work with you on your idea.  Appreciate the incredible feat that it is.

However, do not think that because they work for you that they are now enlisted to your dictatorship. You need to involve them in core discussions, listen to their ideas and feedback and cultivate a culture of appreciation and shared passion.   A happy, engaged employee is 5x as productive as a frustrated, stymied or sad employee.  This ebbs and flows, so you really need to watch for it on a daily basis.

Showing appreciation for those that work for with you is not optional; you cannot over-recognize their best efforts.  At the same time, it is a balancing act.  There are times for the carrot and other times it is best to lead them with a stick.  Each employee will respond differently, so it’s a skill that requires fine tuning for everyone you work with.   Personally, as much as I love a good reward, I value constructive criticism significantly more; I’d much rather hear how I can do even better next time than dwell on what went right. Unfortunately, what I, you, or anyone else prefer is completely different than the next person you hire.

I constantly feel humbled by the fact that I have a team helping me make Greenhorn Connect a success today.  I do everything I can to make sure Pardees and Ian know that and have learned well the power of having excited, motivated people helping you fulfill your vision. An hour spent cultivating your employees will pay you back exponentially.

2) Uncover and fix problems when they’re small.

With all the hustle and constant activity buzzing around a startup, it’s easy to overlook small problems. Don’t.

When problems are small, solutions are small as well. When problems grow up, then it takes big, dramatic solutions to overcome them. If it’s an interpersonal issue or a major team issue, then suddenly that small issue can lead to someone having to be let go.

Catch problems when they’re small by reading your employees;  look at their face and posture, and if an employee seems down or upset…asking them if something is up and if you can help has huge immediate and long term benefits.

Conflicts and small issues are often simple misunderstandings or honest mistakes. Tackling them head on breeds a culture of accountability and openness to healthy criticism.  When you get your team in this habit, it becomes much easier to avoid major problems, because they never get that big.  Having a discussion about firing someone is a much more dramatic discussion than talking to an employee about a minor issue that may have caused conflict or hurt the company.  Nip problems in the bud and encourage your employees to do so as well.

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This post may seem like stating the obvious, but theory and practice are two very different things.  Just like hard skills require practice and active use to become sharper, leadership skills like the issues above require active diligence to become adept at them. Ask yourself how your team is doing at managing these issues; I bet there’s times you’ve noticed your team’s mood affected productivity or a problem grew larger than it should have and caused trouble.

Have you learned these lessons the hard way? What key leadership skills do you think first time entrepreneurs need most?

Torture and Culture

3 June 2011

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Thanks to the “War on Terror” the topic of torture is much more front and center than it was in the past.  As life mirrors art, I’ve noticed that popular culture has picked up on it.

In movies and television, torture has become an increasingly prevalent piece of plots. Jack Bauer, hero of the long running show, 24, has regularly used it to get answers and even supposed unexpected everyman hero, MIT educated, Sean Walker of The Event has used torture to get answers.

With real life and art showing torture so prevalently…is it any surprise that more than half of all American teens condone torture?

What’s most interesting is that it wasn’t always like that. We didn’t always glorify it or even condone it.

I just finished watching an old Star Trek the Next Generation episode that addressed torture head on and was far from supportive of the practice. In the episode, Captain Picard is captured by an alien race and tortured for answers. He refuses to break down and repeatedly discusses the ethics and effectiveness of torture. In the end, once he’s free, he admits to the ship’s counselor that after the torture not only was he willing to tell them anything they wanted, he thought he *saw* what they told him to see. (The episode is called “Chain of Command” and you can find an awesome article examining the episode on Slate here.)

As art can also mirror life, it’s well worth noting a practice from World War II. At Fort Hunt, high level German prisoners were subjected to chess, ping pong and steak dinners. Shockingly, these prisoners befriended their captors and divulge massive quantities of highly accurate information. Learn more about the incredible story here.

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Our military’s practice of torture is only further enabled by our cultural embrace of its supposed effectiveness. The survey of teens shows that we may be more impressionable than we like to believe. I’m genuinely concerned for the implications of our future where the majority of people embrace practices so contradictory to our founding principles of Life, Liberty and the Pursuit of Happiness.

Why Unlimited Vacation is a Bad Idea for Startups

18 May 2011

20 Comments

One of the really cool things about being a startup is that you can make your own rules.  There is no HR department to try to make you act all “corporate” and instill strict rules and guidelines or even have an “employee manual.”  There is no doubt that this added freedom creates much of the innovative culture that drives a startup and attracts great employees.

One common area to experiment in for a startup is with the vacation policy. Talking to founders, I’ve heard startups use the entire spectrum from no vacation to unlimited vacation.  Today, I’d like to examine the unlimited vacation policy and why I think it may not be the best idea for startups.

There are really just 2 sides to this issue I see: how your best and worst employees handle it.

Unlimited Vacation takes advantage of your best employees.

I’m a workaholic. So are many other startupers. Especially for an employee punching above their weight class, there can be a lot of pressure to constantly move the ball forward and make progress. That can mean taking very few breaks, and risking burn out.

When you have unlimited vacation, there is no finite number. That number feels very foreign and it’s hard to understand when you are allowed to take time off and how much is appropriate.  When you become a veteran entrepreneur, the concept may make sense and be easy as you’ll know when you should take time off; you fully appreciate the concept that a recharged version of yourself is much more productive than the borderline exhausted version of you slogging along for months.  However, when you’re new, knowing the actual amount of time you’re allowed to take off can really help you not feel guilty taking time off when you need it.

Unlimited Vacation is a dangerous option for bad employees.

What do you do when one of your employees wants to take time off repeatedly in a short amount of time or a time that is far from ideal for your startup? How do you rein that in without conflict? When you talk about issues around “wrongful termination,” it’s a hard argument to say you’re firing someone for taking too much “unlimited vacation.”  This can cause all kinds of conflict in your company as you can have resentment between employees and frustration for both parties; those taking the vacation think they’re merely exercising the rule as written and those working hard and not taking breaks see it as abuse.

So what’s the solution?

Have an open vacation policy with a finite number of vacation days. 

What does this really mean? It means you shouldn’t have to apply for vacation days, but there should be a specific number you get each year. That finite number means employees can’t abuse their freedom to take time when you need it, but you can also tell your workaholic employees, “Hey, you have 90% of your time still unused…take it!”

Obviously vacation and sick policies are a complicated issue at startups. This is just one piece of a larger question about how to get the most out of your employees while keeping them happy, healthy and motivated.

Have you worked at a startup with Unlimited Vacation or another creative vacation policy? What were the pros and cons?