The 2 Most Important Skills to Start Your Career

There is nothing harder than starting out or starting over. When you are new, it can be difficult to get your foot in the door and make a good impression. It can be hard to tell the difference between incompetence and a simple lack of experience.

Therefore, if you’re just starting out, there are two skills that are essential and will carry you farther than any others:

1) A Fierce Attention to Detail.

Any manager with a new hire has in the back of their mind the questions of, “Can they handle this?” and “How much do I need to keep an eye on their work?” If your manager knows you have an excellent eye for the details, they will be much more trusting in your abilities, knowing that you’ve taken good notes of their instructions, will triple check your work for careless mistakes and won’t do anything to make them look bad.  Building this trust can be the difference between a fast accelerating career with new responsibilities and languishing as an entry-level hire for years.

The longer I’ve been a manager and worked on product teams, the more I appreciate this trait. Over and over again we see the evidence of how the little details are what people notice and love (A great example is how Crashlytics built for Tweets which led to their viral growth). This is at the heart of great craftsmanship.

2) A Hunger to Learn.

Unfortunately, minding the details is not enough to succeed. You must also be eager to learn new skills. The faster you level up, the more likely you are to advance in your career whether always at the same company or at new ones. You need to learn from others and seek out sources of information on your own, which are skills in and of themselves to develop.

Many people in other careers have asked me how to get into product management, which isn’t always easy. However, one of the easiest ways to change your role is to work at a growing company and show how fast you can learn and grow.  This gives a company the confidence to give you more and new responsibilities.

The Combination is the Key.

When you combine an attention to detail with a hunger to learn, you will be unstoppable. Watching for the little details will make you more inquisitive and help you find the hidden gems and little secrets others gloss over. The little details are where life’s curiosities and greatest lessons lie.

As you grow the confidence of others and use curiosity to drive your learning, you will open new doors and build great relationships with others in your field. You are likely to attract great mentors who enjoy watching your development and love sharing stories and lessons to further your learning. They will also become your strongest advocates, either as great references, or the kinds of people that hire you again and again.

What do you think are the most important skills for those starting out?

Building a network is about playing the long game

When I moved to San Francisco, in many ways I was totally starting over. After 8 years in Boston including 3 in its tech scene, I had built many great friendships and connections. I still keep in touch with many of them today, but being across the country is definitely not the same as having beers, dinners and coffees regularly.

I find nothing more fascinating than the challenges and struggles in building a company and how some succeed where so many others fail. I greatly value the insights into how companies are run and the tough decisions leaders face, so it was really disappointing to suddenly miss out on all those conversations I was often privy to in Boston. As I’ve worked to rebuild what I had in Boston, I’ve come to realize an important lesson:

Building a network is about playing the long game.

A number of my friends in Boston are now successful founders and C level leaders. Many are raising B and C rounds right now and two even sold to Twitter for a substantial sum. I’ve learned an immense amount in conversations with them and found their first hand accounts inspiring.

As much as I would love to know the same caliber of successful founders in the Valley right away, it’s unlikely to happen. Instead, what I can do is the same thing I unintentionally did in Boston: get to know people before their startup success. Some of the aforementioned founders I knew when they had just raised an angel round, others before they even started working on their ideas and were instead employees at other startups.

You don’t know Jack.

I hear many people try to get to know the big names in town or even pretend they already do because they talked to Ev or Jack or Zuck once at an event. When you think about the odds of them remembering you or answering your email (if you even have their contact info) it’s pretty slim.

…but you could know the next Jack.

Instead, focus on getting to know the talented people around you that will be successful. Find ways to be helpful for them (much more likely than you being able to help Zuck) and keep it all in perspective; over time you will grow and develop and so will your friends. Like a fine wine you’ll find your network gets better with age. Those same people will happily return your emails and provide assistance no matter how successful they become. They may even work with you on your next venture.

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.

Why I’m Starting a Company Now

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

1) I have a zen financial outlook

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

2) Customer development, homes

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

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

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

3) I’m going to be a recruiting machine

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

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

4) It’s who you know…

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

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

5) Greenhorn is a mini-startup

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

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

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

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

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

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


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

Fall Accelerator in Boston?

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

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

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

Spring: TechStars

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

…but nothing for the Fall or Winter.

This leads me to a few questions:

What would you tell someone in his situation?

Can Boston add another accelerator?

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

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.

My thoughts on #BetterMA: How to Retain Gen Y

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

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?

A few added thoughts for the Globe piece today…

I’m sure some of the old folks woke up this morning and said, “ugh…another discussion on young entrepreneurs leaving.”  I know some of you are tired of it and I know things have gotten a lot better over the last year and a half or so, but the fact is that we’ve solved only a handful of the challenges that do exist. And like the little brother in a big family, our accomplishments will always be compared to our big brother in the Valley.

The important thing to remember is: talking about this and not taking action is called complaining. Talking about this and doing something about it is healthy (and necessary) discourse. Great sports teams watch and learn from what other teams do, so we should be no different.

With all this in mind, here’s a couple of things I’d like to add to the great article in the Globe today and supporting pieces by local young entrepreneurs:

1) DartBoston is missed.

Yes, Dart still does Family Dinners, which Victoria Song is doing an absolutely amazing job on. And I also realize that the pace that Dart worked at in the beginning was completely unsustainable (and financially unsupported). I’m also very happy for where Cort and Jake are both crushing it at startups.

That being said, the comaraderie and friendships formed at DartBoston events like Pokin Holes and Capitalize are what energized me when I first started Greenhorn Connect and few people cared. That energy also drew in new students in great numbers (as I wrote about in the Globe piece)

I’ve actually been talking with Fan Bi recently about how we can resurrect elements of it in a less demanding fashion for the organizers.  So far, we’ve done a few dinners and poker nights, but there’s an intermediate step between small dinners and huge parties that is missing for young people.

2) How can we get more mainstream press?

One of the reasons that New York City has picked up so fast is that they have major press there, which has given great attention to the startups making things happen there.  Unfortunately, we don’t have a Mashable, Times or Wall Street Journal, but we do have press that would allow locals to see us: the Globe, the Herald, the Metro and the Improper Bostonian.  Now obviously those 4 Boston press arms are VERY different from one another, but they all reach different audiences that might just include some people who should join our startup community.

Imagine if some of the cool startups such as some of the ones Kirsner wrote about got small features in the Metro every week? I take the T every day and believe it or not, a lot of people read them.  It might just get us a better early adopter crowd (the other half is playing angry birds, so maybe they’ll download that app written about) and at the least will make people aware of the startup scene, which has ancillary benefits like rescuing more talented, experienced folks from big companies (another thing we could work on in Boston).

3) You have to remember what it was like to be a student

I spent 6 great years at Northeastern University. Unlike many “Boston” schools, we’re literally right in the city. They even send us out on co-ops to work at 3 places to get us off campus. I even got an entrepreneurial degree in that 6th year (a Master’s in Technological Entrepreneurship).  I had no idea that the startup scene existed except for a few off-hand mentions until I graduated and then created Greenhorn Connect.

When you’re in college, you have student groups, intramural sports, classes, parties and tests.  Each university is a contained ecosystem that students rarely poke their head out of unless it’s to do something fun in the city. That’s why you have to go to them.  Once you get them excited and can point them to a few good things (maybe one of the upcoming startup parties like RubyRiot or Binno de Mayo (this week!) plus Greenhorn Connect and Web Innovators) and they’ll be on their way, but it starts with us providing some of the activation energy.

4) I’m tired of young people leaving

A couple weeks ago we had a #startupdinner of 13 young entrepreneurs. 4 were planning on leaving (Tim Chae and Evan Morikawa amongst them) and Fan Bi predicted 10 would be gone by next year.

I want what’s best for young entrepreneurs and frankly, I don’t have a lot of good answers for them. Right now, I don’t feel comfortable looking them in the eye and saying, “No. Don’t go. You should stay here. Trust me.” Maybe I’m just a little tired from all the things I do. Maybe my vision is foggy. Maybe that’s what I should be telling them, but when I get emails from friends now in the Valley that say things like this, it gives me pause:

I’d get out here as fast as you can. Capital aside, the level of access you get out here is like night and day from Boston. I know the people who run the APIs for [all of the big players in his industry], and just about anyone else we have an interest in working with is just a tweet or email away. They’re all accessible, they’re all responsive, and since they don’t know who’ll end up the next Google, they’re pretty darned helpful.

 

Just the parties alone — there are tech parties with 400-500 people attending. It’s wild. Kegs are allowed at events. Journalists attend them, meet you, and write about you the next week, sending tons of traffic. Companies get acquired regularly, making even more parties, new angels, and feeding the whole system.

I’m excited for Ruby Riot, Binno de Mayo (this week!), the forthcoming Playtime Party and DartBoston‘s party that will blow the roof off (trust me). We need this. 4 big parties gets you on that track. So anyone grumpy about that Globe post…dust off your dance shoes and come out and remind everyone why they’d be a fool to leave.

And if you want to leave a comment that can give me some ammo next time a young person asks me about leaving, I’d much appreciate it…

Why the Peekaboo Mobile Acquisition is Huge for Boston

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!