SF Startup Survival Guide: How to help your employee move to San Francisco

Congratulations! You’ve found a new person to join your startup in the Valley. You found them outside the area, so now you’re moving them so they can join your team in your office.

They’ve signed their offer letter and booked their flight, so all you need to do is get their desk ready and a set of keys to the office, right? Wrong. If you really want to help your employee succeed and build a strong relationship with them, you need to understand there are many needs you should try to help them with beyond the office.

The key to understanding what your new employee faces is to follow Maslow’s Hierarchy of Needs. Most people join a startup for Levels 4 and 5, because they bring opportunities for more rewarding and interesting work than you’ll find at a big company. It is likely many of the keys that convinced them to join your company play to those desires.

The problem is, when you move, Maslow’s Hierarchy is flipped on it’s head; your basic life needs of safety, shelter and belonging are all wiped out as you leave those things behind in the last place you lived.  Maslow made his list a hierarchy for a reason; you don’t care about Self-Actualization and Esteem nearly as much when you don’t know where you’re sleeping at night or have no friends.

Having moved to SF just 4 months ago, I’ve had to rebuild those first three levels (to varying degrees of success). I’d like to share my advice for a founder importing talent so their employees can have an easier transition.

Level 1: Physiological

When you move to a new city everything is uncertain. Where will you live? How will you get to work? Where do you buy groceries and other household items? Your most basic needs are up in the air, which will mess with even the strongest individual’s psyche.

If you’re moving as a young adult, chances are you’re going to be moving out here and then starting your search for an apartment. Especially in San Francisco, nothing could be more stressful. Even if you’re lucky enough to have a friend’s place to stay, most people feel uncomfortable putting their friends out and even the best friends are going to be grimacing if a stay with them drags on very long.

What should you do for your employee?

In my last post in the SF Startup Survival Guide, I captured all the advice I learned in finding an apartment in San Francisco. There’s a lot that would blindside even a veteran of living in big cities, so the first thing would be to pass them posts like that and adding any advice from your coworkers. The latter has the bonus of being a great opportunity for a new employee to bond with a coworker.

Also realize that you should have your employee focus on finding their place to live. They will not be able to focus on their jobs while they don’t even know where their bed is going to be. If they’re like I was, I moved because the job was an opportunity to punch above my weight class which made me eager to prove myself. That came in direct conflict to taking time off to look at apartments, but Hiten (CEO of the company I work at, KISSmetrics) wisely encouraged me to, “do whatever you need to.”  It was 10:45am on a Monday that I found my apartment, the second one I had looked at that morning. If you only search on weekends, it will take forever to find anything given how competitive the market is and drag the stress (and productivity loss) on much longer than it needs to.

Level 2: Safety

Once you have the bare essentials of a roof over your head, your concerns shift to figuring out how to start building your life here in town: settling in, building routines and getting the items you may have discarded before moving.

San Francisco is a decently safe city…except where it isn’t.  A newcomer could be fooled by the high end stores on the borders of the Tenderloin and City Hall and Opera in Civic Center. These are not places to be in at night without your wits about you.  It’s also an expensive city that can quickly shrink your bank account.

What should you do for your employee?

Make sure they have what they need and know where to go for things. Don’t assume anything. Showing you care beyond their ability to ship code or execute on marketing plans not only shows you’re not a selfish leader, but it will score major points with them.  Those points matter a lot in the competitive employment environment here; it won’t be long before they’ll be meeting other startupers that would be happy to hire away your talent.

On the financial front, realize it is quite expensive to move. Based on my own experience and talking to others, it appears it costs an average of $5,000 to move an individual and upwards of $10,000 to move a family. This will put a serious dent in anyone’s bank account so if you can offer a relocation package, expect it to need to hit those numbers to cover someone’s costs. If you can’t offer one (I didn’t get one at KISSmetrics), realize the importance of that first paycheck and make sure that they’ll receive it on time and as expected.

Level 3: Love/Belonging

When you move to a new city, you’re leaving behind many of your friends and often much of your family, too. We’re all social creatures and by making a big move, you’re essentially cutting off much of your natural support system. As I’ve talked to others who are also transplants to this city, this seems to be the dirty secret no one wants to talk about; nobody wants to admit they have no life outside work (and not by choice).

I completely underestimated the impact my move from Boston to San Francisco would have on me personally. In Boston, I had spent the last 8 years building more valued friendships than I could count. I played on the same soccer team for 4 years, played Ultimate Frisbee with much of the same group for 6 years, built countless friends in the tech scene and still had great friendships with many classmates at Northeastern. I also had a best friend and roommate (hat tip to David Sonnenshein) who always had my back, was always down for a fun stuff to do and knew when I needed to be told, “Stop working and grab a beer!”

Within my first two weeks of moving out here to SF, my father had a heart attack scare (thankfully a false alarm) and my grandmother (last living grandparent) was diagnosed with terminal cancer (she passed May 15, 2012). Piling on top of all the other things I was dealing with settling into SF and having no one close to talk to, it almost broke me. It didn’t help SF is 3 hours behind the West Coast so I couldn’t talk to friends and family before work (I was asleep) or after (they were asleep).

Luckily, Hiten noticed there was something up and took a more active role and interest in my well being. We got dinner a number of evenings, which helped me have someone to talk to and led to us talking through my challenges. We then worked on some ideas on how I could handle things better, which included visiting my grandmother, taking some time off and being more strategic about how I settle in.

What should you do for your employee?

Your employee has a roof over their head and has started to settle in to the basics of life. Your work here is done, right? Wrong. A depressed or lonely employee will not be nearly as productive and engaged as one who is happy inside and out of the office.  But what can you do? You can’t be their BFF, but you can help.

As Hiten did with me, you should give extra attention to see how your new employee is doing in their first couple of months. Make it okay for them to talk about what they’re struggling with. The Friday off Hiten gave me after I told him about my dying grandmother was exceptionally helpful and built a lot of trust.

Beyond dealing with personal crises, the best thing you can do to help a new employee is have them make a list of all the things they loved most where they lived before. I did this and it helped tremendously. I realized that I really missed playing on sports teams, playing poker with my startup friends, seeing movies in theaters and “Scotch day” with my roommate.

Armed with a list of things I missed, I could start picking off what I missed doing. Your other employees can likely help out with this (I relied mainly on Google) and recommend the sports leagues they know about (I play in Bay Area Disc for Ultimate and Sports4Good for Socccer), sites with things to do (Zach Cole helped me find Sosh) and anyone they know that might share similar interests. SF has much to offer regardless of your interests, which definitely helps.

If you’re at an early stage startup, everyone is likely working long hours. That makes it all the harder to make friends as you don’t have a lot of free time to work on building those relationships. Recognizing this, building a culture of “work hard, play hard” can help, by ensuring all your employees have time to have fun and potentially become friends outside work, which has obvious ancillary benefits.


Hiring someone new to your team is more than adding an asset like a printer or computer; remember they’re a living, breathing human with hopes, dreams and needs. In this competitive environment, showing the extra effort to care about your employees beyond the work they produce can have a huge impact on your culture and retention.

And if you’re new to the city, know you’re not alone. Life has gotten a lot better than my first few weeks here, but I still have a long way to go to replace all the things I miss most about my life in Boston. If you want to grab coffee or a beer, know any casual poker games or have an affection for good scotch or movies, let me know.

How to Plan for Succession in Your Business

Whether you’re building a volunteer organization, a high growth business or a profitable side project, there is likely going to come a day when you no longer will be able to (or want to) run it.  Building something that outlasts your direct efforts is a real accomplishment, but few talk about how to actually do it.

As I just moved to San Francisco, I’ve gone through the process of succession for my role in Boston running Greenhorn Connect, a site that aggregates everything going on in the Boston startup scene.  (You obviously can’t run the day to day of such a site from another city.)

I’ve been fortunate enough to find someone great, Paul Hlatky, to take over and even managed to get my awesome team on board with the idea. This was no mistake. I was fortunate to have been able to solicit advice from some of Boston’s best leaders. I’d like to share what I learned from them and in the process of handling this succession.

Special thanks in particular to Tim Rowe of the Cambridge Innovation Center and Michael Skok of North Bridge Venture Partners for their advice for this post.

How to Handle Succession Planning for Your Organization

1) Start planning before you need a successor.

In October 2011, I talked with my team at our monthly Greenhorn Team meeting about the idea of me not always running the day to day of Greenhorn Connect. After 2 full years, it seemed like it would make sense for someone new to give Greenhorn Connect a fresh injection of energy and vision. At the same time, I was trying to launch a company, so I realized that a founder of a growing business would not have the time for a side project like GHC.

From that meeting forward, I started quietly keeping an eye out for a successor and thinking about what it would take to hand off the business. This led me to ask myself a few key questions:

  • What are the core benefits to the job I can sell someone on?
  • What is the archetype for the person & skills needed for this role?
  • What role would I expect to have after the transition?
  • What don’t I know about succession planning that I should learn about?

At the outset, I had few answers, but it gave me a framework to get started on the process before I needed my successor. It also helped me understand what questions to ask others when I had the opportunity to learn how they’d approach the challenges I felt were coming.

2) Be proactive and seek out your sucessor.

Once I realized the kind of person I was looking for was going to be a hungry student new to our ecosystem and hungry to help others that were new to the ecosystem, I needed to find some leads. By narrowing the definition of who I was looking for I was able to concentrate my search to a few student leaders starting to emerge in the community.  Since I didn’t want succession to be done in the spotlight, I had to seek them out directly and somewhat discretely.

Paul, then a senior at BU, had attended our massive conference the unconference and wrote a passionate blog post about connecting students. It came across my Twitter stream one night and I followed up with him by commenting and then meeting up with him for coffee.

3) Try before you buy.

Successions that fail don’t end well for anyone. Just ask John Sculley (aka- Jobs’s disastrous first successor). To save embarrassment for you and your potential successor, the best thing you can do is try before you buy. This means working with them and spending a lot of time with them to make sure you feel comfortable with them taking over.

For Paul and I, this trial ended up turning into a jointly organized Startup Career Fair. Pulling off a major event like this (500+ students and over 30 companies) requires a great deal of coordination and help. Paul showed incredibly skill as he recruited dozens of students to help, negotiated huge discounts from our venue and otherwise showed great business instincts. Even before the fair occurred I knew I had the right person, so I made the pitch.

4) Sell the Dream.

No matter how ugly, everyone loves their own baby. But if you’re handing it off to someone else, you have to convince them to love your baby, too.  Once you’re certain you’ve found the right person, you need to grab a pair of rose colored glasses and sell the dream of why this person should want to take over for you.

While I knew Paul was a great young hustler, I didn’t know everything about his motivations yet, so when I made the pitch, I laid out all the benefits I knew Greenhorn Connect could provide its leader. I focused on what I knew motivated me to do it as well as some of the things that were cool, ancillary benefits of the role.

If you’re stuck on what to say, just think about how Willy Wonka made it impossible for Charlie to pass on the opportunity to run the chocolate factory…and reveals much of his succession plans:

(Quite possibly the best “Sell the Dream” ever. Skip to 2:29 in the video)

5) Focus on values and key success factors.

When you choose a successor, you have to realize they are not you. You can’t expect them to do everything as you have done it before. Instead, you need to focus on instilling the core values of the role and what matters most to the success of the business or organization. These values and key success factors will act as guide posts for your organization’s new leader to make their own decisions by.

In the case of Greenhorn Connect, I shared a large Google Doc with Paul filled with insights to what I felt had made the site a success to date and things I felt were our core strengths and weaknesses.  I also shared with him many of the processes and productivity hacks I had used to run the site, but I tried to emphasize that he was welcome to come up with new strategies and tactics as long as they didn’t compromise our core values.

With what I’ve seen in Paul’s first 3 months running GHC, I can see that he learned the values and is now bringing some of his own style and ideas to the table, making Greenhorn Connect better than it was before.

5) Put them out in front.

Now that you’ve got your successor excited about the role and are instilling your values in them, it’s time to shine the spotlight on them.  When I asked Tim Rowe for advice on succession he had a lot to say about this in particular. He told me:

Give Paul the spotlight. Make it all about him. When you’re out there, let him be the one up on stage. Meanwhile, you should be in the background telling everyone, “isn’t he great?” Keep pushing him and promoting him from behind the scenes until one day you aren’t back stage and everyone simply knows he’s in charge now.

There’s a lot of pride and ego you have to swallow to do this, but in order to avoid casting a tall shadow on them, you need to let them shine while you’re still around.  It creates an intermediate step where you and your sucessor are together, rather than an instant switch from you to them that would be jarring.

6) Get out of the way.

Of all the steps, this is by far the hardest. You’re handing off your baby you watched grow and develop and now you have to trust someone else to continue caring for it. If you don’t get out of the way, you’ll end up meddling in their work, preventing them from succeeding.

To truly be a successor, they have to be able to put their stamp on it. This only comes with the independence of full control. As Michael Skok told me:

It doesn’t matter if they succeed or fail; either way if you do it right, they’ll be to blame for it, not you.

In some ways it feels heartless; when you’re handing it off, you want to feel like you have some lasting value you can provide. However,  the best thing you can do is tell them you’re there if they need you, but otherwise absent.

I’m still working at this last step. Since I stayed on as CFO at Greenhorn Connect, I still have some duties with the business. These duties are a blessing and a curse; I still get to see how GHC is doing, but it also then tempts me to interject in Paul’s work to make observations and suggestions.

Luckily, Paul is very gracious about them and he’s also strong enough to stick to his guns and do what he thinks is best. I think I’m getting better at this last step of late, but I still catch myself at times trying to prevent Paul from making his own mistakes. I have to let him make his own mistakes or he won’t learn.

Succession is hard.  But to ensure good things continue beyond the lifespan of its creator, it’s an important step in the lifecycle of every organization. I hope these tips will help you keep your great organization living on.

What advice do you have for succession planning?

Leadership Lessons in Real Life: Leading by Example

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):

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

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.


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.

Competition and Inspiration: Environmental Effects of Nantucket and Beyond

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.

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.

Leadership Lessons First Time Entrepreneurs Forget

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.

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?

Why Unlimited Vacation is a Bad Idea for Startups

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?

Leadership Lessons from Pixar

Last night, I watched the documentary, The Pixar Story, which is exactly what it sounds like: the story of Pixar becoming the powerhouse computer animation film company it is today.  You can view the documentary by clicking here.

It’s a fascinating story hearing how they built a team of people sharing a common and seemingly impossible dream when they started: making a full-length, feature-film made entirely with computer animation.

There’s a lot of awesome anecdotes in the film and the documentary’s creators did an excellent job of capturing the emotions of creating these movies many of us know so well: Toy Story, the Incredibles, Monsters Inc and Finding Nemo.

I’m a bit of a leadership geek, so I wanted to share leadership lessons I saw in the film that stood out.  (Note: some of these are also inspired by the book I just finished reading: Little Bets, which uses Pixar as one of the key companies it draws stories from.)

1) Collaboration and spontaneity matters

After their first major success, Pixar opened a new facility that embodied the culture they had built and worked to foster it to greater levels.  This new facility is expansive and open and allows for employees to be creative and collaborative in new ways.

This is why cubicles are the enemy of any great company. Those random connections that happen in an open environment vastly outweigh the costs of interrupting others.

2) Openness to criticism and feedback is essential

Everyone sees the world a bit differently, which is hugely valuable.  At about 68 minutes in the film you see an artist showing his peers a rough draft of Nemo the fish talking to his Father.  The artist had focused all his efforts on the father and Nemo looked basically dead. His peers helped him realize the importance of showing life in both characters.  Throughout the film, collaboration is emphasized as a key item.

Without a collaborative environment where feedback is welcomed, you will never be able to move quickly enough.

3) Celebrate real success

The Pixar team worked insane hours and under unbelievable pressure as they more than once put their backs against the wall in making a film and trying to rewrite it with tight deadlines.  In one scene, the director of Monster’s Inc announces to the Pixar company the box office receipts for opening weekend, which were huge.  The whole company was celebrating with champagne and cheers.

Many have talked about the distorted reality of celebrating funding for a startup.  It’s important to remember that especially after a major struggle for your team to celebrate key successes and recognize those making extreme efforts.

4) Take bold chances

After 3 straight hits on their hands at Pixar, the reigns of directing their next film was handed over to someone who had never even been an assistant director.  As it turned out, this led to Monsters, inc, a huge success.

Recognizing talent within your company and giving them the opportunity to grow beyond their current role can yield great results as demonstrated here.  The director of Monsters, inc, was employee #2 at Pixar.  He was ready.

5) Push the Limits

At Pixar, it was a constant back and forth: the tech team would give animators new possibilities to try to animate and then the animators would come back pushing the tech team to allow them to do even more.  In A Bug’s Life, the tech team said they could only render 50 ants on screen at a time. The animators pushed back and the tech team delivered; they made it possible to render over 400 ants on screen.

The greatest inventions of man have always come from those willing to try to make the impossible possible. It is a worthy exercise to ask your team “what if” and make things happen.

6) Never Settle

After a string of hits, Pixar was on top of the world. They could have tried to stick to their formula and made more great movies, but they didn’t. Continuing to push themselves, they brought on Brad Bird, who had just mad the flop, Iron Giant.  He brought fresh ideas to the company and thrived in the Pixar culture that assimilated him.

When you get comfortable and rest on your laurels, that provides a window of opportunity for your competition. If you continue to push the limits and innovate, you will never be caught.

7) Be your own best customer

It was said best right in the documentary, “We’re a team of people that love film…We just make things we all just want to see.”  As it turns out, when they were unhappy with films and pushed themselves to rewrite and improve what they were doing, they created great movies that they were proud of and people loved.

Every startup knows the best customer in the early days is full of ideas and constructive criticism. Make your people a great customer of their work.

8) Your competition doesn’t understand your value prop

Towards the end of the film, they mention the decline of 2D animation and the fact that other studies gave up on the medium after a string of Pixar successes.  As it turns out, they seemed to think that audiences no longer had an interest in the 2D animation form and that the success of Pixar was attributed to their technology.  They couldn’t be more wrong.

Know what your company is all about at its core and focus on delivering your best possible product. Don’t worry about competition, because they are likely to look at your success and be unable to understand what the real reasons for your success are.

9)  Empower your people to have control of their work

Everyone at Pixar has a great level of accountability to themselves and their peers. Everyone takes great pride in their work and believes in the mission.  Pixar’s employees are operating at the highest level of Maslow’s Hierarchy of Needs and the quality of their work demonstrates it.

Give your employees the opportunity to surprise you. Give them ownership and the opportunity to see their work to the end.  This empowerment will give them new vigor in their work.

10) Overnight successes are far from overnight

Pixar was a fledgling arm of LucasFilm in the 1970s when their journey began.  It wasn’t until two decades later that Toy Story finally came out. They were constantly on the edge of going out of business and had many sleepless months producing their hits.

No success is overnight. It’s a collection of small victories that eventually add up and one day reach the tipping point of success.

Maslow’s Hierarchy of Needs

Lessons Learned from Observing the OnSwipe Investment Announcement

I really enjoyed seeing the explosion of stuff for local Jason Baptiste and his startup OnSwipe. To really see how this all works, you need to read all the articles surrounding the events of the last 24 hours:

This morning:

TechStars NYC Announces their companies in their first class with one Mystery company:

BostInnovation: “NYC TechStars Companies Announced”

note the allusion: “And a mystery company focused on building a “Platform for Tablet Publishing and Advertising.”  I immediately thought of PadPressed (the old name for OnSwipe) for a lot of reasons I won’t go into, but couldn’t figure out why they wouldn’t be announced.  Then it was cleared up…


1) TechCrunch Announces the Funding:

OnSwipe Raises, Like, A Million Dollars

2) Jason’s take on the OnSwipe Blog:

“The Road Ahead: Why Tablet Publishing Is Transforming The Way We Consume Media”

3) And Boston Angel Wayne Chang talks about his investment in OnSwipe:

“Proud To Be a Part of OnSwipe”


So what to learn from this? A few quick lessons and observations:

1) A mystery breeds intrigue

Being the mystery company…of the first TechStars…in tech hotbed and media mecca New York City…is a heck of a way to start things off with a bang.  TechStars tries to help companies make more noise and this is huge for OnSwipe.  On top of the buzz the other companies get, OnSwipe gets a huge extra magnification as people were looking to see what that 11th company was up to.

Lesson: If you can create some intrigue…definitely do! People love a good mystery.

2) Announce it and be AS LOUD AS POSSIBLE!

So we’ve got the source for Startup Tech News aka- Tech Crunch, writing about your funding announcement, a brilliant manifesto on the company blog by a truly gifted writer and the Angel investor that was the first to commit all writing about it at the same time.  Now that’s how you burn up Twitter and the social webs!

Lesson: The more ways you can get your message out, the wider the reach and the greater the buzz you can create.  Buzz = ongoing press attention, easier recruiting of employees and plenty of opportunity for serendipity.

3) The First Commit Came from BOSTON and was a new Angel

I’ve heard more than I care to about what it’s like to try to raise angel money in Boston and so it’s thrilling to hear that the first commitment for investing in OnSwipe was a Boston Angel (see Wayne Chang’s blog post).

Lesson: Boston.is.not.dead. There’s good people and if you show you have the right idea, the right team and the right skills, you can get funded around here.

4) Jason is the PERFECT choice to execute on this idea

Jason is a truly gifted writer/blogger both on his own blog: http://jasonlbaptiste.com/ as well as for the past few months Dharmesh Shah’s widely read OnStartups Blog: http://onstartups.com/ So when you take someone who is reaching tons of people because of his gift of writing…and happens to be giving tons of great advice on being an entrepreneur, that’s a perfect fit for someone that wants to lead a company that wants to change the way content is consumed.

Lesson: If you’re pursuing an idea, think about why you are the PERFECT choice for the idea. Then make sure the investors you pitch know why.

5) Jason has the BIG VISION investors love

So besides solid domain expertise, a solid personal brand to leverage and an initial product that is apparently already impressing investors, you have a guy ready to take on a big vision of how to transform an industry.  In his post on OnSwipe, he says it all:

“…50 billion dollars of traditional media spend needs to shift online.  Our belief is that it’s in a holding pattern and can’t. There’s a disconnect between award winning beautiful ads found in print and tasteless spam ads that litter the web. We think touch enabled devices can let this change by providing advertising people actually enjoy with the best of the web layered on- mobile, local, social, and more.”

Lesson: Think BIG, but be grounded in understanding the macro trends and opportunities.  Share that vision with the world and execute.


So to me, this is a home run all around at this stage. Yes, they still have to execute, but they’ve got an exciting and awesome set of pieces in motion.

This is the first of what I’m sure will be many more major steps in the future of OnSwipe.  I wish Jason and the rest of his team all the best and look forward to using it on my iPad soon.

Book Review: 10 Powerful Personas By Kevin Vogelsang

Ever wonder what makes a leader great?  Ever spend time thinking about what the strengths are in your personality or how you might be able to become more like great people around you? Kevin Vogelsang has and he’s written a book to help you answer those questions.  In his just released book “10 Powerful Personas, Kevin examines key attributes of 10 different qualities found in leaders. I learned a lot from the book and I’d like to share a few of the lessons here:

1) Leaders come from everywhere

One of the most interesting things about Kevin’s book is the balance in people he uses as examples of different leaders.  He uses everyone from General Patton to his football coach to his mother as examples of the different powerful personas to great effect.  Because of his wide variety of examples, it made me think about who around me, both famous and friend, that exhibited the traits he describes; it was an excellent reminder that you can really learn from anyone around you if you simply raise your awareness and look for it.

<Click here to read the other reasons at GreenhornConnect.com>