Leadership Lessons in Real Life: Leading by Example

January 31, 2012

I’m a leadership junkie. Nothing fires me up quite like a good example of leadership, especially if it comes in the face of adversity.  It’s probably why I love so many cheesy sports movies like The Replacements and Hoosiers. They’re all chock full of leadership lessons. As art imitates life, it’s fitting this weekend I witnessed some truly profound leadership right in front of me at a soccer game.

Setting the Stage:

I play on an indoor soccer team as part of the Boston Ski and Sports Club. It’s nothing fancy and to the outside world, it’s pretty meaningless. But to those of us that play it has a lot of meaning. Many of us grew up playing sports and continued all through high school and college. There’s a void left by that only filled by finding a team sport to play even after school.

The team I’m on is pretty special. No egos. No dead weight. Just a bunch of athletes that enjoy playing with each other and find that perfect balance between hyper competitiveness and having fun.

That mix combined with a little luck found us in the championship game of our league this past Sunday. We were coming off one of our best performances of the year in our 5-3 semifinal victory, so we were pretty confident entering the game.  Things did not go as planned, but thanks to a great example of leadership in its purest form all was not lost.

Struggles and Setbacks:

In the first half we stumbled a bit to a 0-1 deficit. At halftime we all talked about how we just needed to finish a few opportunities and we’re in it. We were a little discouraged to have not scored yet, but confident in our abilities to have a solid second half.

Unfortunately, the second half started off very poorly. Within minutes of the half starting an errant play by me led to an own-goal. Seizing the momentum, just a minute after that, another goal was scored as our defense looked lost.

We hung our heads. Down 0-3 with 20 minutes left. But one of us refused to relent. Rob was more fired up than ever. He kept encouraging all of us to keep fighting. There was plenty of time to come back. He started chasing down every ball within range and ripping shots every chance he got.  The opponent’s momentum was stopped when Rob ripped his first goal to bring us within 2 goals.

Rob then subbed out after a lengthy shift and not long after a fourth goal came. down 1-4, just 15 minutes left. While the rest of us looked beaten and thought we were toast, Rob was more passionate than ever.  He ran down balls, beat defenders and kept pushing. At first the rest of the team didn’t respond. He was like a one man wrecking crew, but playing 1 on 5.

The Turning Point:

With Rob running around the field like a maniac for a few minutes finally another player on our team started making big plays too. Soon after another joined in and before we knew it, we had the whole team challenging every ball and pushing hard on goal.

Not long after, Rob got his second goal of the night. After the goal he ran right by our bench yelling at all of us to get fired up and get ready to come in and make a play too.

It worked. With 8 minutes left, down 2-4, Brandon dribbled hard into the defense and was taken down inside the box. Penalty kick. Like a man on fire, Rob convinced Brandon to let him take the shot, which he quickly buried in the back of the net. Now down by just 1 goal, Rob got a little crazy.

In outdoor soccer, when you’re down with little time left, you’ll often grab the ball after you score and bring it back to the mid line so the other team can’t stall waiting to kick off. Fired up after his goal and desperate to keep our momentum, Rob attempted to take the ball from our opponent and run it up. A near fight ensued that got our whole bench fired up and fortunately led to no penalties.

Completing the Comeback:

After the post-goal scuffle, there was no doubt that everyone on our team was ready to do whatever it took to tie the game. As a team we won every 50-50 ball in the open field and even took some 40-60 balls from them. We wanted it. Bad. Rob’s passion had infected the whole team and there was nothing our opponent could do about it.

With just 4 minutes left, a quick save by our keeper with a throw up the sideline led to a fast break. A quick give and go then led to a shot from the corner which Brandon buried in the back of the net. Tie game.

With all the momentum in our favor we pushed hard to try to win before time ran out, but unfortunately we were unable to settle it in regulation.

Overtime in our league means straight to Penalty Kicks (PKs). Leading the way once again, Rob scored our first PK, and went on to lead encouragement of our goalie and other shooters. A clutch save by our keeper and 3 straight goals made led us to a 3-2 victory in PKs.

The Moral of the Story:

Leadership is not about what happens when times are easy. It is what you do when the times are tough that matters. When the rest of the team was ready to give up, Rob refused to lose.  When no one else seemed to have any fight left in them, Rob continued to lead by example, challenging every ball, running hard on every play and encouraging everyone.  Eventually, he got others to join in and soon everyone was believing again and putting everything they had into the game.

No matter your challenge, realize that leadership means flying in the face of group think (the game is over) and being bold enough to stick with it long enough for others to join you and change your situation, whether that be a soccer comeback, your company on the ropes, or dancing on a hill (my favorite TED talk ever, below):

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Posted by Jason Evanish

Does Boston Have Too Many Startups? A response to Kirsner’s Sunday Globe Article

October 18, 2011

This post originally appeared on Greenhorn Connect and has a boatload of comments. See here: https://greenhornconnect.com/blog/does-boston-have-too-many-startups-response-kirsner-s-sunday-globe-article

 

In the Sunday Globe this week, Scott Kirsner posed the question, “Does Boston Have Too Many Startups?”  The article seemed to try to make the argument that all our little startups should just be employees at bigger startups (disregarding how bigger startups, start out…).

The article is really best summed up in the quote in the article by Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.” I find it fitting that coincidentally, Ryan Durkin, COO of CampusLive (and mentee of Mr. Driscoll as a Highland Capital portfolio company) writes about attracting talent today:  http://www.ryandurkin.com/blog/2011/10/how-to-hire-dudes-showers-kitchens/

I’ve spoken with a number of friends about the article and had some interesting Twitter conversations as well and wanted to highlight some of the key points that came from them.  (Note: Kirsner sought out some thoughts which you can see on his Globe blog here.)

1) We don’t talk about logical career paths enough

Quick: explain, with examples, a logical career path for someone to evolve to be a successful entrepreneur.  Stumped? I know I am. Most examples I think of fit in the “Zuckerberg” files of folks who didn’t have much of a startup pedigree before launching their monster success (think Matt Lauzon, the many TechStars companies, etc).  I look at the titans of our community like David Cancel, Dharmesh Shah, Jeff Bussgang and know very little about “how they got here.”

It’s easy to tell people “go work for a startup first,” but you need to show them examples of people that have succeeded in doing that, and if you didn’t as a founder, then you have to acknowledge you have some hypocrisy on your hands.

2) We don’t have enough serial entrepreneurs and mafias

We are all familiar with the Paypal Mafia and some of the many startups the former employees spawned, but where are Boston’s Mafia’s? There was a great Bostinnovation series covering some of them, but it seems like there are fewer and certainly less celebrated.

These mafias are exactly what would convince someone to *join* a startup instead of start their own: join a team and have a great exit and then have peers and valuable experience to start another.  Maybe an offshoot of Eric Paley‘s Founder Dialogues needs to be “Mafia Dialogues” and bring in a few people from a successful team to share their combined story. We also need to think about whether it’s good for a CEO of a billion dollar company to be proud that all of his first 10 employees are still working at his now billion dollar company.

I think Rob Go was also on the right track highlighting the power team of Brian Balfour, Aaron White and Ariel Diaz teaming up for Boundless Learning (and also happens to talk about the importance of “more shots on goal,” not less startups as Kirsner suggests).

3) We don’t take enough chances on Greenhorns

I am very lucky. What few of you remember is that no one was interested in hiring me when I came into the tech scene. John Prendergast was the first to give me a small shot doing some work for him, which then led to the opportunity to pitch Laura and the oneforty team on joining them (John was on their board).  That was a 6 month journey to get that full time offer from oneforty.  If I didn’t live as lean as possible and have the luxury of a little savings, I may have never made it.

Just like our investors are often criticized for wanting too much traction before they invest, many of our companies only want to hire people that have done a role before.  I know too many young, eager people who want to work at startups, and yet there doesn’t seem to be many roles available to them.  I get asked about Janet Aronica, who I hired at oneforty, a few times a month it seems and the irony is, I doubt anyone else would have taken a chance on a young, eager talent coming from the low rungs of a PR firm.  I also look at Kristin Dziadul, who once made videos trying to get HubSpot’s attention and was smartly hired by Rob May and Backupify.

This is not to lump everyone together. Matt Lauzon and the Gemvara folks have taken chances, and I know Diane Hessan has been an awesome advocate for some of the truly hungry Gen Y folks. Unfortunately, the rest of the community hasn’t caught on yet.

4) We don’t take recruiting seriously

It bears repeating via Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.”  Vinod Khosla went as far as to say “New CEOs should spend 50% of their time recruiting.”  I’ve seen the aggressiveness of Sequoia firsthand as they held an event the night before Startup Bootcamp for their founders who were speaking to tell a bit of their stories, answer questions and meet people. I know Dropbox has spoken at at least 3 Boston area schools in the last 6 months.  How many schools have you spoken at in your own back yard?

Maybe we need an event or two to talk more about recruiting talent (One of my favorite events ever was a fireside chat with Akhil of MassChallenge and Paul English talking about recruiting).  I think it’s a competitive advantage for some companies while others throw money at it, but it certainly seems like it might help.  More awesome posts on the subject like Brian Balfour’s and David Cancel’s would help too.

5) Complaining about funded startups is an insult to entrepreneurs

The funding climate in Boston has improved, but it’s still hard to raise money.  As the opening to the Bloomberg TV show states, TechStars is more selective than Harvard. If you manage to raise money, that’s quite an accomplishment, as David Friend says in his message to Kirsner.  If you have an idea that goes far enough to funding, you have an at bat and need to go try to execute. The amount you’ll learn with your small team will be tremendous and put you in a great position to contribute to another company.

Now, living off of savings, is obviously a big risk and so if someone is risking financial ruin to keep their fledgling startup alive, it most likely makes sense to go work somewhere. Then again, the Valley wouldn’t have Airbnb if those guys weren’t relentless.

6) We need to clarify what a startup is

Wayfair is a $350Mn+ company. HubSpot has over 300 employees.  Are both of them still startups? Neither? I worked at E Ink when they went from about 90 employees to 165.  From my experience, the Dunbar number is very real.  The culture really started to shift at that point and more HR rules and regulations hit, not by choice, but out of necessity.  Few companies are really like Google and provide the independence and opportunities similar to startups, and even there, I don’t think you get the same thing.

I’ve heard about HubSpot’s education classes that try to teach some business and entrepreneurial lessons, but I have a feeling they’re the exception, not the rule. I also wonder how they’ll be able to maintain it as they grow further.

7) What motivates an entrepreneur or early stage employee?

Another great quote from Craig Driscoll on advising companies was, “They need to figure out how to recruit and create jobs that are attractive for entrepreneurial people.”  An entrepreneurial person cares much more about working with other smart people, having flexibility and independence in their role and a feeling of true contribution and influence in the big picture of what they do.

When I worked at E Ink, everyone looked forward to their quarterly meetings where Russ Wilcox explained the state of the company.  It lifted the covers on how the company was doing and especially during the wild ride that was the exploding popularity of the Kindle, you could feel everyone having a renewed sense of purpose after work as they were a part of the amazing opportunity to replace paper books with E Ink technology.  I think that same sentiment is happening now with Gemvara as Matt hammers home the vision to change jewelry and e commerce on the web.  Entrepreneurial employees want to be a part of something bigger than themselves, while feeling like they’re really making a contribution.

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I’m glad Scott brought this conversation out for discussion, but feel like it missed the mark on what really matters in this ecosystem developing.

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Posted by Jason Evanish

Competition and Inspiration: Environmental Effects of Nantucket and Beyond

June 19, 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.

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Posted by Jason Evanish

Leadership Lessons First Time Entrepreneurs Forget

June 7, 2011

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?

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Posted by Jason Evanish

Why Unlimited Vacation is a Bad Idea for Startups

May 18, 2011

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?

20 Comments | Concepts, entrepreneurship, Leadership | Permalink
Posted by Jason Evanish

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