My thoughts on #BetterMA: How to Retain Gen Y

June 8, 2011

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.

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

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.

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 the Peekaboo Mobile Acquisition is Huge for Boston

April 12, 2011

When I saw the tweet come through my Tweetdeck yesterday that Peekaboo Mobile had been acquired, I was surprised, excited and very happy for Ben, Michael and their team. These guys hustle and so it’s great to see them get a return for their efforts over the last year plus.  They also now have a great opportunity to build more greatness over at nSphere.  While everyone is busy focusing on undisclosed deal terms and the acquisition itself, I’d like to highlight what I think is the bigger story:

Why the Peekaboo Mobile Acquisition is Huge for Boston

1) Young Hustlers Get Paid…in Boston!!!

If someone is still unsure if you can make it as a young entrepreneur in Boston, this is a great example that you definitely can succeed.  Ben and Mike hit this city door to door and made it happen on hustle and brains. Few cities are as compact as this one which actually helped their local model.

2) A New Angel gets her First Exit

Jennifer Lum started investing less than a year ago and here she has her first exit.  This is a big deal for quite a few reasons.

First, she already had a taste of success, which should help her feel good about her investment portfolio and encourage her to stay the course on her continued investments. If you follow her on Twitter, you can see she’s travelling all over the US and Canada scouring for good deals.

Second, as this is an exit, she can likely make even more investments or have money left for more follow on rounds in her current investments. Either way, more money in the hands of an investor that is proactive is a very good thing.

Finally, Jennifer took a chance on some young entrepreneurs in Boston and it paid off. This will hopefully encourage her and many others to think about what young people can make happen in this new tech explosion in Boston and beyond.

3) This is the First Exit by a DartBoston Member

It wasn’t that long ago that Ben and Mike were pitching on DartBoston’s Capitalize.  Ali Powell wrote a great recap on BostInnovation here as well.

The fact is, there are a bunch of young entrepreneurs hustling like crazy in Boston and so I expect this is the first of many successes for members of the DartBoston community. I wouldn’t count out Cort Johnson, Kabir Hemrajani, Alex Moore (even if he did transplant), or many others.

4) Startups Can Be Fun

In the sea of all the hard work required to make a startup win, it’s easy to get caught up in the daily grind and forget to have fun.  Ben and Mike definitely didn’t do that. Their mascot kept things light and fun and showed their creativity and were often at those drink ups that were both relaxing and filled with good startup conversation.

This acquisition is a shining example of many of the best things happening in Boston. Let’s congratulate, Ben, Mike, and their team as well as  Jennifer and hope we see more things like this and hopefully even bigger things for them and other hustlers in Boston!


I’m all in on Boston.

March 29, 2011

My last post has been sitting at the top of my blog for awhile and I want to make one thing clear:

I’m betting on Boston.

Any questions?


A frank discussion on the best place to build your startup as a young entrepreneur…

March 19, 2011

We all have goals in life. Those of us in the startup community are particularly aspirational. We dream of building great products with millions of users. We dream of leading great companies filled with awesome people.  We dream of TechCrunch articles, keynote speeches, magazine covers, and the opportunity to create great wealth. We dream of beating the ridiculous odds that say we’re idiots for even trying, especially those of us still so young.

On Friday evening at #WhiskeyFriday, which was sadly under-represented this week (really? Boston can only find 5-10 people to grab drinks after work in Central Square?), I was involved in a discussion about whether, as a young entrepreneur, it made more sense to move to the Valley or try to build a company in Boston.

This wasn’t another b*tch session; this was two friends honestly and frankly talking about the facts at hand. We’ve both been around the block here, had our own and seen our friends’ experiences in this community and so we’re well aware of the situation here and we also have enough contact with the Valley to feel qualified to understand what’s there as well.

I’m not here to make this some magnificent, articulate post, so here’s just in simple bullet form, the Pros & Cons of our two ecosystems and how two young entrepreneurs think about it as we sit in the midst of a new tech bubble (which is what sparked this discussion in the first place):

{Disclaimer: If you’re “tired” of the Boston vs. SV discussion, this post is not for you. Please close your browser window and go back to putting your head in the sand. Don’t worry,the bubble will be over in a few years and you’ll barely have noticed…}

The Valley:

Advantage:

  • Massive access to money
  • Stronger culture of helping each other
  • Companies that can acquire you
  • More industry experienced people around
  • Early adopter culture
  • Great tech press

Disadvantages:

  • Finding & keeping engineering talent is VERY hard
    • Try competing with Godfather offers from Facebook, Zynga, Google, etc
  • Very small fish in a HUGE pond
  • If you move there, you’re basically starting over

Boston:

Advantages:

  • HUGE talent pool to recruit from
    • Universities and less competitive environment overall
  • Established network here

Disadvantages:

  • Underdeveloped mentoring
  • Very Weak acquisition market
    • How do Boston co’s exit? Seems “rarely” is the right term…
  • Weak funding climate
  • No press that gets users or national attention

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So with all of that…the question basically boiled down to:

Is it better to build a company in the Valley and try to return to Boston to recruit

OR

Build a company in Boston and travel a ton (literally and virtually) to NYC and the Valley to try to leverage the advantages there.

I don’t have the answer to that, but I think you can guess what side I’m betting on for now…

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Got comments? Let’s keep this discussion productive and please review the disclaimer at the top in case you missed it and are irritated by the comparison.

This is two individuals talking about what’s best for their careers not an ecosystem taken at a macro level…although in many ways it’s one in the same.

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Interested in more like this? You can follow me on Twitter by clicking here or find more of my blog posts at my site GreenhornConnect.com


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