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…

Tonight:

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”

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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.

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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>

8 Resolutions in 2010

With the turning of the new year, it’s that time when people make resolutions. Yes, most people make them and soon break them, but I’m hoping to be different.  These are issues I’ve recognized and was already working to improve before the New Year. I’m simply using the turning of the year to make these goals public; I think by putting them out there for the world to see, you put a bit more pressure on yourself to deliver.  So, below are my resolutions and a few items for how YOU can help me make these all happen.

8 Resolutions in 2010

1) Improve my Punctuality: I’ve had many meetings over the past few months and unfortunately, I’ve had a bad habit of not making it on time to many of them. Sometimes it’s a beyond my control like when the T didn’t run for an hour while Obama spoke at MIT, but often, I’m just not giving myself enough time to get places.

How You can help me: Hold me accountable for punctuality. I’m open to creative ideas. Currently Cort, who films GreenhornTV for me, has it that I owe him a beer for every 5 min late I am. So far, I haven’t been late yet since we made that arrangement.

2)  Improve Time Management: As I launched Greenhorn Connect, I took the approach of doing everything all the time. That’s not a good strategy. I’ve gotten better as time has gone by, but I still find myself losing some days to doing things, but not Getting Things Done.

How You can help me: Any suggestions on how I can become more effective and efficient (books, articles or tips) are much appreciated. Thanks Apollo and Mike for your help already!

3) Get Back to the Gym: For my first 6+ years in Boston, I was a regular at Northeastern’s awesome gym, the Marino Center.  No matter how busy I was through undergraduate and graduate school, I always made time for the gym every other day.  Since I launched Greenhorn Connect, I’ve watched my gym attendance dwindle to not having made it since before Thanksgiving.  Fortunately, I have a pull up bar in my apartment and I’ve been getting creative by creating quick 20 minute workouts in my apartment, but it would be much better if I got back to my old workout routines that are a bit more diverse.

4) Get back to Running: I was a pretty good runner in high school on my cross country and track teams. I racked up a few thousand miles in that time and really look back at it as some of my favorite memories from high school. Unfortunately, I’ve never been able to hammer out a routine in Boston that compared and so I’ve progressively lost my endurance.  I can’t run on concrete (not that I think anyone really can without injury) and this isn’t suburban PA so I can’t run on the roads.  This means I need to get out and take advantage of the 2 great locations near me: the Esplanade and Jamaica Pond.  This one will probably wait until spring when weather improves.

How You can help me: I think having the team really helped me stick to my running, so if anyone lives in the Back Bay area and is looking for a running partner or knows of any running groups, let me know.  I think I’d be running in the 7-8 min mile pace right now, looking to run 3-5 miles a day.

5) Read a Book per Week: I saw this come across the Twitter scape and thought it was great: Read a Book a Week for a Year. At first I said to myself, “I’m so busy! I don’t have time to read THAT much!” Then I read that post…and I realized, that’s like 30-40 pages a day. That’s not so bad. I can do that! So, I just started this on Jan 1st and am 3 for 3 as of this writing for getting my pages knocked out each day. As I hopefully progress on this I plan to also write reviews on Greenhorn Connect for the books I like best.

How You can help me: Two ways: 1) Recommend any books you suggest I read. 2) Loan me a book. Yes, I know I can go to a library, but if I borrow it from you, I bet you’ve read it and could then compare thoughts on the book briefly.

6) Post More Often: Keeping the Greenhorn Connect Blog going became my priority over the past couple of months, but now I think it’s starting to stabilize. I like the idea of having things I write here and on Greenhorn Connect (much like there are New Years Resolutions at both places). I’m going to try to commit to posting more often. To help that, I’m going to try adopting a new Seth Godin-like style here where I just write a couple paragraphs about a thought I have and leave it open for continued thought by you and I.

7) Keep learning: Since I started grad school in September 2008, I feel like I’ve been drinking from the fire hose in learning about entrepreneurship. I look at everything I do as a learning experience and that’s led to zero regrets in my somewhat unorthodox journey.  I hope to keep that mindset in 2010 and continue to leverage past experiences to develop future success.

How You can help me: Give me constructive criticism. I really take all the advice and feedback I get from people to heart. I find many are apprehensive to give feedback, but it’s the only way you can truly improve. So please…share your advice, suggestions and criticisms…I’m listening, and more importantly, acting on them.

8.) Pay it forward: One of the things I’ve learned over the past few months is that often, you can’t help those that are helping you. Instead, the best thing you can do is pay it forward and help others regardless of what they can do for you.  I’ve met with a number of people to share what I’ve learned from Greenhorn Connect and other recent experiences and look forward to helping when and how I can in the future.

How I can help You: Ask! You don’t know unless you try. If I can help you I will.

To me, these are more than resolutions; they’re part of my evolution. I think they actually all tie together as there’s a greater theme of curiosity, learning and organization.  Success in one is likely help success in the others.   Please comment or contact me if you can help with any of those or I can help you.

Lessons Learned: Under Promise, Over Deliver

As the clock struck midnight tonight, a vision was officially only that; GreenhornConnect failed to relaunch as planned on Monday.  A series of technical difficulties left us unable to put the site up for you to see in all its glory.  We’d been planning this launch, in honor of Global Entrepreneurship Week, for a few weeks and had worked tirelessly to get all of the resources and content in order and start lining up our guest bloggers.  After many Monster energy drinks and little sleep, it was a thrilling, but ultimately draining experience.  We’re now inching close to the actual launch, but I wanted to hit on a few lessons I learned over the last 48 hours:

1) Nothing…I repeat…Nothing ever goes as Planned

If there’s any complexity to a problem, there will be hiccups. And usually, those hiccups will come where you assumed a task would be quick and easy.  We’re all very good at recognizing the big, time consuming tasks we face. Most of us can even budget relatively well how to get them done and project when that will be.  BUT, the problem is, those other things, the stuff we assume will be easy are not budgeted for and not planned for and so it is these problems that derail us.

Why is that, you ask? Well, it’s really simple, actually.  The more experienced and knowledgeable you are about something, the better you understand it. Those big, time consuming tasks, chances are you’ve done them before, so that’s why you can budget them so well.  But those other things…they’re probably something you haven’t done very much of; maybe it’s something you’ve done once in a different way, or it’s a new technique that should make your life easier. Regardless of the reason, it’s the stuff you don’t know that will hurt you.

So what’s the takeaway here?

Leave yourself a cushion for those hiccups to take time to be resolved and try to ask yourself what steps you’re taking for granted.

2) Over Promise, Under Deliver…err….Under Promise, Over Deliver

When you’re a young entrepreneur, you have to build your reputation from scratch. Everything you do is a small token that adds up to credibility and people believing in you.  Every time you do something good…whether it’s ask a good question at an event, impress someone with your knowledge in a conversation, follow through on a request by someone, etc, you’re adding another chip to the reputation pot. Unfortunately, when you do something bad…like don’t follow through on a promise, or offend someone or otherwise make yourself look bad, you lose many chips from the reputation pot.  Run out of chips and you’re in trouble.

So what am I getting at? If you do good things for awhile, you can get away with a mess up or two, but you still always need to be doing everything in your power to demonstrate your capabilities and why you’re not just another person who muses about being an entrepreneur versus someone who GTD (Gets Things Done).

In the case of the site relaunch, I feel like I really messed up. I promised to a lot of people we’d be relaunching Monday morning and that obviously didn’t happen. My problem was I got hung up on how awesome it would be if we did versus the reality of the fact that we had little margin for error to meet that date.  So, to anyone who went to GreenhornConnect.com on Monday and were disappointed to see the same old landing page and resource list, I apologize.  I hope you’ll check back today and see how far it’s come and join us on a journey to continue to develop and grow Greenhorn Connect.  I hope my enthusiasm and passion for this when we’ve met at events shows through in this and hopefully I have a few chips left in that pot.

So what’s the takeaway?

If you promise less than you know you can deliver, then you’ll wow people when you do more than that. (as opposed to disappoint them…)

3) Do Something You Truly Love

The last thing I want to hit on is the passion of entrepreneurship.  Regardless of what your venture is, you have to absolutely love it. It’s gotta be your passion.  Even as I saw one of my roommates going out with his girlfriend for the night as I stayed in to work on the site or as the other slept in while I got up to go to a conference, I never second guessed my choices. I love going to entrepreneurship events and solving this problem for new entrepreneurs.  If I didn’t love this, there’s no way I’d want to do all the behind the scenes labors that go into making a site like Greenhorn a reality. Motivations of profit are always good and a necessary part of business, but cannot trump passion when you’re starting a business.

When you’re searching for ideas for a startup, remember to look for things you love and problems that relate to them. Solve those problems.  Kabir loves music, which led to RiotVineFan Bi loves fashion, so he started Blank Label.  Matt Webster loves craft beer, so he’s running Drink A Better Brew.

GreenhornConnect is my passion and I’m going to try to exceed all expectations and promises from now on. What’s yours?

The Young Entrepreneur’s Guide, Part III: Building a Network, Reputation and Following

Many people have written tips, guides and questions for aspiring entrepreneurs.  Many of them are excellent, but I don’t think anyone has captured the essence of the stages a young entrepreneur goes through and specific advice for what they should do at each stage.  As part of our efforts at GreenhornConnect.com, we want to create a central location that provides the information that an aspiring entrepreneur needs to go from starting out (Is this for me? What should I do?) to evaluating an idea (What goes into a business plan? How do I build a team?)  to being a real business (Do I need investment? What tools should I use?).

In the coming weeks, I’ll be writing different sections of this guide in my blog, pulling from my experiences, what I’ve read and advice I’ve heard from others. If you read this and think something is missing or disagree with any of the advice, please comment; I want this to be the best guide possible and will gladly give you credit for your contribution. Thanks.

Thus far: See Part I: Starting from Scratch, Part II: Getting Out There

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Part III: Building a Reputation, Network and a Following

You’re out in the community meeting people, reading and learning…now it’s time to establish a reputation and build a following. Here’s how.

1) Understand Ideas are Free

It’s easy to get in the mindset that someone will steal your idea and that you’re giving away something of value by talking to others about their ideas.  This is completely the wrong mindset. Sharing ideas is exactly what you want to do.  It has an incredible amount of benefits:

A) It gets your ideas out of your head and refined by others.  As the CEO of Zipcar said, “every person you meet is a free consultant.”

B) Everyone in the community wants to help each other. If they can’t directly help you, they are more than happy to connect you with someone they know that can help. They can’t help you if they don’t know what your ideas are.

C) It builds credibility.  People recognize and remember those that share good ideas and ask good questions.

In the end, ideas are like a boomerang; the more you share your thoughts with others, they more they’ll share theirs with you. No one will steal your idea, because they’re already working on what they’re passionate about and your passion will always trump someone who is just copying you.

2) Actions Speak Louder…

As a young entrepreneur, you have to build your reputation from scratch. This means that everything you do makes a small contribution to how people judge you.  The best way to build this reputation is through consistently displaying the qualities people look for.  Are you eager to learn? Do you ask questions and share ideas? Do you follow through on everything you say you’ll do?  Do you help others?  Are you honest? If you under-promise and over-deliver, you will always impress people.  Pay it forward and you’ll be amazed at what others will do for you.

3) Use Twitter

It’s great to be up to date on your industries of interest and the trends and topics of the day for entrepreneurs, but to really make a contribution and get involved, you need to be an active part of the conversation.  The easiest way to do this is with Twitter.

You should already be on twitter, seeing what events are being shared as well as articles and ideas. You can do the same thing. If you like something someone already shared, give it a retweet. If you read something really interesting, make a comment about it and link to it in a tweet.  If you have a question for the community, ask it. You never know who might see it.

Also, in addition to connecting with people on linkedin, follow those people and others you see in the community on twitter. They’ll usually follow you back, which leads to an audience that will notice what you have to say.

4) Start a Blog

If you have more to say than 140 characters allows, you should consider starting a blog.  It’s a great way to share your thoughts, questions and ideas on an issue or just share an experience you had.  It also works great with Twitter as you can tweet your entry and if people like it, it will get re-tweeted and more people will read it (and likely start following you).

If you have the passion for writing out your ideas in blog form, then go for it.  To truly be effective, you need to blog a few times a week or once a week at absolute minimum. At first that my seem daunting, but in my experience, that’s not as hard as it seems. There are many great ideas out there for what to blog about; just decide what your blog’s focus will be and give it a shot. If you’re passionate about the subject, you’ll find that writing about it will come much more naturally than your last report for school or work.

There are a lot of great tips for getting started: Here, Here and Here.

5) Tie it All Together

By now you should be on Twitter, LinkedIn and maybe even have a blog. You’re also out there at events.  This means you’re now part of both the real and virtual conversation. To best utilize them, tie them all together.

LinkedIn gives you the ability to directly feed your blog into your LinkedIn page and to provide up to 3 links to other sites from your profile.  These links should be your Twitter profile, your blog and your startup, when you have one.   Meanwhile, Twitter allows you to link directly to one site, so you should then tie it to your blog or LinkedIn.  Finally, most blogs allow for links, so you should link to your Twitter account, LinkedIn and your company.

By doing this, you create a net. No matter how people find you, they can find out everything about you with just a few clicks. This can be really valuable, as anyone can see what you write about (your blog), what your thoughts are (Twitter) and your background/experience (LinkedIn).  This really works. I actually got a job because of my blog; they were able to see my background and interests and out of the blue asked to meet with me.

If you say things that resonate with people, you never know what can happen.

Are you a part of the conversation?

Coming Next Week: Part IV: Working on Your Idea

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This is ongoing series to try to build a comprehensive, lasting guide for aspiring entrepreneurs. I would greatly appreciate any input in the comments below to make this the best it can be.  Thanks!

MIT 100K Elevator Pitch Contest: A Lesson in Awesome

What has a roaring crowd complete with thunder sticks,  a set of hosts in costume, a dancing spaceman and people talking about everything from backless labels to prostate cancer?  No, it’s not the World Series and your average night of commercials. It’s the MIT 100k, where they set the gold standard for awesome.

When I arrived, the event was already in full swing.  As I walked into the auditorium I was hit with an incredible ball of energy; you could feel the excitement and enthusiasm of the crowd and participants. There was also a very entertaining host (dancing spaceman = good, microwave pitch = not so much) and tons of awesome elevator pitches. Where else can you go and hear someone talk about Indiana Jones, prostates and impotence and get multiple laughs, all in under a minute?

To me, the lesson in this is simple: be awesome.  MIT could have had a standard, bland event with limited sound production (sans the Star Trek sound effects), hosts in (regular, not space) suits and a reserved (thunderstick-less) audience.  That would have produced a solid event, with interesting pitches.  Instead, they dialed it  up to an “11″ and went all out to entertain and energize everyone in the room.  This is how you get people excited about entrepreneurship.  This is how you make people say “wow. I wish I had pitched” and realize that entrepreneurship can be as cool as sports.

Cheers, MIT100K team. Awesome event.  Looking forward to future events.

The Young Entrepreneur’s Guide, Part I: Starting from Scratch

Many people have written tips, guides and questions for aspiring entrepreneurs.  Many of them are excellent, but I don’t think anyone has captured the essence of the stages a young entrepreneur goes through and specific advice for what they should do at each stage.  As part of our efforts at GreenhornConnect.com, we want to create a central location that provides the information that an aspiring entrepreneur needs to go from starting out (Is this for me? What should I do?) to evaluating an idea (What goes into a business plan? How do I build a team?)  to being a real business (Do I need investment? What tools should I use?).

In the coming weeks, I’ll be writing different sections of this guide in my blog, pulling from my experiences, what I’ve read and advice I’ve heard from others. If you read this and think something is missing or disagree with any of the advice, please comment; I want this to be the best guide possible and will gladly give you credit for your contribution. Thanks.

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PART I: Starting from Scratch
You recently had the epiphany you want to be an entrepreneur, but really haven’t gotten started yet.  Here’s what to do…

1) Is this for You?

When you first decide you are really interested in entrepreneurship, the key is to get informed.  It’s easy to say you love startups, but it’s another thing to truly understand what you’re saying.  The best way to determine if it is for you is to start reading.  Read inspirational articles written by entrepreneurs like Ken Morse, Paul Graham and Mark Cuban.  Still interested? Talk to family and friends and try to find people who are entrepreneurs that you can talk to about what it’s like.  After hearing about all the challenges, long hours and risk of failure, if you still want to be an entrepreneur, read on…

2) Try EVERYTHING…Be Curious

A key trait of being an entrepreneur is a desire to learn. When you’re getting started, you should try to take in everything you can to learn about different types of startups and roles you can fill in a startup.  Fill your Google Reader with industries you’re interested in and blogs in areas you want to learn more about.  You don’t have to read every article, just the ones that interest you; simply reading the headlines of the other articles can help you to grasp where different industries are technologically.  There are also great websites, magazines, books, and presentations you can check out.  Ask other entrepreneurs what they read.  Add what you like to your list and leave the rest.

3) Overwhelmed? Don’t know where to start?

If you really need a few starting points, here’s a few sites, blogs and items I personally like best (note: This is somewhat Boston biased, because that’s where I live. Find things in your area to get a view of your local entrepreneurship scene):

Websites:  TechCrunch, Venture Beat, Silicon Alley, Gizmodo, Xconomy
Blogs: OnStartups, Innovation Economy, Startup Lessons Learned
Magazines: Inc Magazine, Popular Science, Technology Review

The takeaway from this is not to copy me; instead, notice the diversity. There are newspapers, tech focused media, business sources and established entrepreneur blogs.  The idea is to get as many perspectives as you can. Try to build a similar list based on your passions and location.

4) Study those you Admire

As you immerse yourself in all of this entrepreneurial content, you’ll start to find certain personalities and businesses keep coming up.  Find the ones that resonate most with you and follow them more closely. If the founder of the company has a blog, read it. If they have a book, buy it. If they’re going to be speaking and you have a chance to see them live or on video, watch it. And if you are fortunate enough to have the chance to sit down with them, make the most of it.  Focus on how they got where they are. Learn from their mistakes and try to understand what made them successful and emulate that.

Still in love with entrepreneurship after starting the learning process?

Now Available: Part II: Getting Out There
See Also: Part III: Building a Reputation, Network and Following & Part IV: Working on Your Idea


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This is ongoing series to try to build a comprehensive, lasting guide for aspiring entrepreneurs. I would greatly appreciate any input in the comments below to make this the best it can be.  Thanks!

MassTLC unConference: Can We Build on the Momentum?

Across Twitter, the blogosphere and professional media, there is an obvious consensus: the MassTLC unConference was a resounding success.  Everyone has been talking and tweeting about the energy and enthusiasm that permeated the event.  I believe everyone left with a renewed feeling of optimism for entrepreneurship in New England and a new set of contacts that will be helpful in whatever ideas, ventures or initiatives they are pursuing.

I have no doubt that, on an individual basis, everyone will greatly benefit from the unConference.  However, the greater question is what larger goals may now be possible because of it. A list of action items were created during Scott Kirsner and Tim Rowe’s session called, “Turbocharging the Entrepreneurial Culture in MA.”  These items require a diverse group of people in the community to come together to address issues big and small.

Being a “greenhorn” in the community, I’m not sure how I can help in some cases, but I want to do my part.  I look forward to launching the site being built by myself and some colleagues to help young entrepreneurs  by providing a consolidated source and aggregate for events, resources and other pertinent information.  In addition, if anyone needs any young entrepreneurs to aide in any of the tasks through man power or just a different perspective, I am certainly willing and I believe I know quite a few others who would gladly get involved as well.

So, my question for you, reading this right now, is how, in any way big or small, are you able to help tackle these action items?

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I also wanted to use this entry to summarize and consolidate everything that happened at the unConference.  As I’ve been reading, listening and watching the reactions to the event, I’ve compiled those all into one place.  Below, you will find every piece of content I know of on the internet (sans individual tweets praising the event) that has been generated as a result of the awesome unConference.  If I missed anything, please comment with the link and I’ll update the list.

The Center of it:
Professional Media:
Bill Warner’s Blog/Photo essay of opening
Session Media:
Bill Warner’s discussion of “starting a company with no money”
Adam Zand’s Collection: http://www.utterli.com/AdamZand
PR Improv:
Music 2.0
SKirsner & TRowe:
My earlier entry w/ List
Picture of session: http://yfrog.com/2pzx9j
Lean Startups
Meetup Group organized by John Prendergast, who led the session: http://www.meetup.com/Lean-Startup-Circle-Boston/
Google Group: http://bit.ly/ewVJs
Steve Blank’s Blog: http://steveblank.com/
Build a Community, Not a Network
Quote of the day:
“Some of you are so smart that you take something that should be an instant failure & turn it into a 4-year failure.” -Bill Warner
“Why, @pistachio asks, are we going up against Silicon Valley as ‘Boston’ & ‘Providence,’ not New England?” -@ Pistachio

Links related to the event itself:
unConference website
MassTLC Website
The Pre-Event Session Wiki
The Sessions Listing Wall
MassTLC Blog

Pieces by the Professional Media:
Mass High Tech
Scott Kirsner’s Friday 5
NECN Coverage
NECN Reporter, Scott Montmimy

Blog Entries on the overall unConference:
Bill Warner’s Blog/Photo essay of opening of event
Bill Warner’s Video of the Event
Bill Warner’s collection of 83 Photos
Brough Turner’s Blog

Specific Session Contemt:

“Starting a Company with no Money”:
Session Audio

“PR Improv”:
Session SummarySession Audio Part 1 & Part 2

“Music 2.0″:
Session Audio

“TurboCharging the Entrepreneurial Culture”:
Session Summary,  “The List”, Photo 1, Photo 2

“Firing Founders is VC-101: How to Keep Your Founder Job”
Session Summary

“Build a Community, Not a Network”:
Session Summary, Photo

“Dodging Bullets that Kill Startups”
Session SummaryLean Startups Meetup Group, Lean Startups Google Group, Steve Blank’s Book & Blog, Eric Ries’s Blog & MIT Event, and another blog

Quote of the day:

Based on number of reTweets:
“Some of you are so smart that you take something that should be an instant failure & turn it into a 4-year failure.” -Bill Warner

Based on importance to improving our community:
“Why are we going up against Silicon Valley as ‘Boston’ & ‘Providence,’ not New England?” -@ Pistachio