Boston, I need your help!

As I prepare to take the giant leap from Boston to San Francisco (in case you missed it read more here), I have a number of things that would be tremendously helpful.  If you can help with any of the following, I’d be most appreciative.

1) Looking for a roommate in SF.

– I’ve heard it’s a nightmare to try to find a place in San Francisco so if you have anyone in your network that lives out there that you could ping and see if they’re looking for a roommate or have a room they need to fill, I’d love to hear from them.

– To give you an idea of what I’m looking for, since KISSmetrics is in SoMA, I’m looking for a place within 20-30 minutes of SoMA via public transportation. Pet free (allergies).

2) Looking to talk to KISSmetrics users

– Does your company use KISSmetrics? Did you try and give up on it? Either way, I’d love to talk to you before I leave March 10th!

– This is your chance to have in person customer development done by the product manager of KISSmetrics. I’ll always be happy to talk to Boston companies, but nothing beats a good in person customer development interview.

3) Looking to Sublet my Somerville Apt

– I have an awesome roommate that loves scotch, pool (I have a table in my apt) and electronics. He’s a great, loyal guy and I need someone to tak over my room in our apartment. It’s near Porter Square. If interested, contact me for details and to come check it out.

4) Anyone I *must* meet in SF?

– A few of you have told me you know some people I need to meet when I get out west. I have a pretty small network out there now so I appreciate any insights on who to meet when I get out there.

5) Advice for Living in SF?

– I know there are a number of you who at one time lived in San Francisco. A number of you have already dropped a lot of knowledge on me for making the most of SF, but if anyone else has advice let me know!

How to get in touch:

Feel free to leave a comment if it’s just some quick SF advice, or to set up a KISSmetrics meeting or connect me to anyone in SF (to meet or talk about roommates), use my gmail: evanish dot j at gmail dot com.


Dear Boston…

Dear Boston,

The past 8 years have been the most invigorating and exciting of my life. You were my first city after escaping the suburbs of central Pennsylvania to attend Northeastern. We were together for the wild rides of the Red Sox playoff runs in 2003, 2004 and 2007 and all the other championships that have made this the city of champions that such a rabid sports town deserves.  Many of my favorite memories with friends involve Boston sports playoff games. You’ve also been a big part of my life’s ups and downs.  Nothing calms my mind better than a walk down Boylston Street on a busy day or a quiet night of reflection by the Christian Science Center reflecting pool.

When I walked onto Northeastern’s campus for the first time, I knew it was where I’d spend the next 5 years. After graduation, I still felt a strong connection as I excitedly got my start at E Ink.  Later, your startup community welcomed me thanks to the amazing DartBoston community and helped shape me into the person I am today: better, faster, smarter, stronger.

All of this is what makes what I’m about to say so hard.

From almost the beginning of my time here, I’ve known I wanted to be an entrepreneur more than anything else in the world; it was a presentation by one of your leaders, Russ Wilcox, when I was a freshman that convinced me of this path. It was later other entrepreneurs that helped me get my start and make me who I am today: from Tim Rowe and Scott Kirsner helping encourage me to start Greenhorn Connect to John Prendergast giving me my first job in the ecosystem as a customer development intern to Laura Fitton being the one person willing to give me a shot at a full time job. Countless others have helped along the way as I’ve needed advice, friendship and a helping hand.

I left oneforty in April 2011 to finally build the great company I’ve always dreamed of.  I wanted to take all the lessons I’ve learned and build the next great anchor company here. Unfortunately, despite trying many different ways to get a company started, nothing has worked.

While I struggled to find the cofounder for my dream company for a multitude of reasons, I was equally failing at finding the right startup idea. Many have told me it’s a spiritual quest; the right idea will grab you and you’ll just “know.”  I know they’re right. That’s how Greenhorn Connect happened, but it doesn’t make the pursuit any easier.

As I continued my quest, I felt I had to start expanding my efforts. That’s why in December, I took a trip to visit your brother out west, San Francisco.  I needed to spend some time away from you to gain perspective and see if the next step could actually be anywhere but here.

I thought I’d never take another job after oneforty. I’m an entrepreneur at heart and felt like my time was now. But after getting perspective out West and having the right person say, “why don’t you come work for me?” I realized I had the perfect opportunity I couldn’t pass up.

There are certain people in the startup world I’ve grown to admire greatly. They’re all on their way to, or already have built great companies. They’re thoughtful leaders with big visions. They understand the pay it forward mentality. And when one of them not only offers you the opportunity to join their team, but in an ideal role, where you get to work directly with them and the company is still at a small enough stage to your liking, you have a too-good-to-pass-on opportunity.

In this perfect storm, the leader is Hiten Shah, the company is KISSmetrics, and my role is Product Manager with the responsibilities to make them a great customer-focused, lean startup with a product their customers love.  I’m both punching above my weight class and bringing all of my skills to the table for this role. I couldn’t be more excited about the opportunities and challenges ahead. At the same time, it hurts greatly to leave Boston to join this San Francisco-based company.

After all the memories, all the great friends inside and out of the startup community and all I’ve built here, I know it’s hard to believe I can pack my bags and leave, but I know this is the next step I must take.  It is far from easy, but a move that makes sense as I work to get closer to my dream of building an achor company.

Your first question is probably, “What happens to Greenhorn Connect?”  Do not worry. Greenhorn Connect is in *great* hands with Paul Hlatky and Pardees Safizadeh.  They are two of the best young people I’ve met in Boston and I’m honored they’ve accepted the ongoing challenge of keeping Greenhorn Connect serving the Boston startup community.  I’ve been working with Paul for months to prepare him to be my successor and I know that he is not only up to the task, but will take Greenhorn Connect to new heights.  He was the driving force behind the Boston Tech Talent Fair and the buses that brought students to #RubyRiot. This is just the beginning of what he can and will do.

While I’ll be handing the reigns to Paul and moving out West, know that Boston and my many friends, mentors and colleagues will not be forgotten. Technology is folding space and time which means that Twitter, Skype and the occasional flight will still keep us connected.  I care so much about our startup community and all the friendships I’ve made along the way, I can’t imagine just forgetting about it.  I’m still planning events in the community like RamenCamp in May and I wouldn’t miss the unConference for anything. I hope to be a bridge between my new home and those here in Boston.

This is the beginning of an exciting and scary new adventure for me and the Greenhorn Connect team. I hope I can count on your support as I set out on my new journey, and more importantly, that you’ll help Paul and Pardees succeed in having Greenhorn Connect continue to support the Boston startup ecosystem.


West Coast Differences – Non Startup Edition

I just took a trip to the Valley for the first time. I’ve had a lot to say about it from the perspective of an entrepreneur (see on Greenhorn Connect here and at OnStartups here). I also noticed quite a few things that have nothing to do with startups that I found culturally interesting.

1) Everyone is nice

Boston can be a cold place, and no I’m not talking about the weather. In general, you just don’t find people being friendly walking down the street, and you definitely don’t see it on the road.

One event really tipified this for me: I had just made it out of a parking garage before close. Because of this I didn’t have time to set my GPS before hitting the road. There was no where to park so I pulled off blocking a driveway. As I was engrossed in entering my destination address into my Garmin, an SUV started honking at me; they needed in the driveway. I of course complied.

What happened next shocked me. The woman parked her car, got out and walked over to where I had pulled off slightly up the street. When I put down my window, she apologized for honking her horn at me. 

2) Everyone weighs 15 pounds less

It’s hard to believe until you see it. Everyone is just in slightly better shape than I see them in Boston. It’s a visual average I noticed after a few days.

I think the cause of this is pretty simple. Nice weather = more time outdoors = more exercise. What kills us (even a gym rat like me) are these brutal winters. It’s really hard to get enough cardio in under those circumstances which means every winter you’re putting on a little weight. Add that up over a winter or two and you quickly get those 15 pounds.

3) The Valley has safer drivers

I’ll be totally honest: after not driving for 7.5 years, I’m a pretty terrible driver. Luckily, people in the Valley drive slower on the highways (around 65 instead of 80) and well, they aren’t MassHoles. They actually use things like turn signals and let people over when they do signal. It was refreshing and the only reason I got back to Boston in one piece.

4) Parking is a breeze outside SF

There’s easy parking in Mountain View and Palo Alto. Even downtown. And it’s free. I was terrified when I forgot to bring quarters with me on my trip and was pleasantly surprised to find that I didn’t need them.

5) Their public transportation is good, but flawed too

We all have our gripes with the MBTA but it gets you where you need to go….usually. The SF system is the same. Their buses are slightly unreliable, but have some drawbacks: the stops often smell of urine and the back part of every bus is covered in graffiti. Meanwhile, the CalTrain is incredible. Like a well oiled machine, the trains fly through the Valley right on schedule.

The best part of their system is they’ve tied it all together on one master card (their version of the Charlie Card). The Clipper Card, as they call it, was the only thing I needed and was easy to pick up at a station.

6) They have a serious homeless population

I found out while I was there that SF has the largest homeless population in the country and for some ridiculous reason they give each of them $400 a year (as if the year round good weather wasn’t attractive enough for the homeless).  I think this is a likely contributor to the bus stop urine smell.

These are just a few of the random differences I noticed in comparing the cities of Boston and SF and the Valley vs. New England.  Have you been both places? What have you noticed as a difference?

Visiting the Valley Next Week

Late in the summer, I wrote about how I thought startups should be “Tricoastal.” What I meant was that you can benefit greatly from having a presence in Boston, New York City and Silicon Valley.   I’ve made a number of visits to New York City in the past 6 months, but have yet to make a real visit to the Valley. It’s finally time to change that.

December 3rd through 8th I’m going to be visiting Silicon Valley.

In order to make the most of it, I plan to spend a little time in 3 of the major hubs: San Francisco, Palo Alto and Mountain View.

If you’re reading this, I’d love to meet up and/or hear your advice on things I can’t miss during this visit. I really want to get a feel for what it’s like out here, what makes the Valley tick and as many of the places that make the Valley special as possible.  I’m also working on a lean product management tool, so if you know any product people I should meet, let me know!

I’ll be in San Francisco: Saturday evening, 12/3 to midday Monday 12/5

I’ll be in Palo Alto: midday Monday 12/5 to midday Wednesday 12/7

I’ll be in Mountain View: midday Wednesday 12/7 through Thursday 12/8

I have places to crash in Palo Alto and Mountain View, but I’m still looking for a place to crash in SF on Saturday and Sunday nights.  If you’ve got a couch, please let me know!

So, what do I need to check out while in town?

3 Questions Brought About by Steve Jobs’s Life

Everyone is tweeting and writing their thoughts as a legend has now passed. I just re-watched Jobs’s Stanford Commencement speech (embedded below) and was as inspired as ever.  As I read more of the tributes like Walt Mossberg’s personal recollection, it got me thinking about 3 heavy questions around all of this:

1) Steve says to “have the courage to follow your heart and intuition,” but why do so few actually have it?

I know so many people that somehow got into a rut at one point and are just on a heartless journey, living paycheck to paycheck at a job they care little about.  I wish for a world with more passionate and inspired people.

2) Would you rather live 56 years in the life of Steve Jobs or 85 years of average American life?

If the cost of changing the world is 1/3rd of your life, that’s actually a pretty high price; there is no commodity more priceless than time.

3) What if Steve’s mother had an abortion instead of putting him up for adoption?

As Steve mentions in his speech, his mother had him out of wedlock and put him up for adoption.  There are few decisions harder in life than the one Steve’s mother faced. The world is fortunate for her decision.

As Walt Mossberg said in his opening, “He was a historical figure on the scale of a Thomas Edison or Henry Ford and set the mold for many other corporate leaders in many other industries.” Only a man as great as Steve could bring about so many great thoughts and so many deep things to think about.

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 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. 

Independence Day & Quicksand

On this long weekend celebrating our country’s independence, I’ve had the opportunity to reflect on the past couple of months since I left oneforty to work on my own startup.  It’s been good to reconnect with a lot of people who I didn’t get to while being heads down at oneforty, recharge my batteries a bit, and have some success in the cofounder search. That being said, I’ve also realized I’ve walked into quicksand…


On the football field, it’s when one thing after another goes wrong despite trying to make plays. In startups, it’s when you let something paralyze you and sink your entrepreneurial efforts. It might be because you focus too much on the wrong thing or ignore the most important thing.

I have tried to plan so many parts of this startup I’m now working on. Whether it be meticulously noting the learnings of the past year at oneforty, saving money so I can go without a salary for a very long period of time, or mapping out all of my contacts and the best ways to leverage them to succeed, everything has been carefully calculated.  I even focused on finding a great tech cofounder before the idea, so I was sure I had good alignment with them before we started running on an idea. All of this though ignores a key element: the idea. It is in this search for the idea that I’ve found myself in quicksand.

Searching for Inspiration.

Being calculated and focused is great for planning to save money and preparing to launch a company, but it’s terrible for trying to generate an idea. You can’t force inspiration.  I know this not for lack of trying:

  • Tried using David Skok’s brainstorming process he blogged about (coincidentally posted my first day after leaving oneforty).  It just left me feeling like a VC; knowing what are good, interesting industries, but not actually feeling like there was a specific idea to go work on.
  • Brainstorming with friends. I hit the white board with friends trying to flesh out some ideas, but only managed to write off a few ideas and failed in trying to dig deeper on ideas identified by using David Skok’s aforementioned process.
  • Talking with friends about the industries of their startups. I talked with a lot of friends in the community about what they were working on to see if any industries caught my eye.  Nothing seemed to spark.
  • Helping friends with their startups.  I tried helping a couple friends with their startups to see if I liked what they were doing (and might join them) or if their industries seemed like it had any interesting problems to solve.  The first two attempts yielded nothing and the verdict is still out on the 3rd.
I’ve found the harder I’ve tried to come up with the idea, the more I’ve sunk.

The Paradox of Choice

I feel a tremendous amount of pressure to come up with an incredible idea. A friend of mine mentioned over coffee that he hopes I don’t become Jarrod Saltalamacchia and it fits how I feel; Jarrod was a hugely touted prospect that came up from the minors and everyone expected he’d be the next great major league catcher.  As it turned out, he’s ended up being more of a journeyman.

I feel like I have to get a big hit in my first at bat and it has crippled me; everything feels like a non-starter because no idea feels “good enough.”  It’s also hard because the closest focus I’ve found is that I know I want to build a B2B SAAS company (mainly because I feel there is the most support and related companies here and I understand B2B more than consumer web.)

Digging Out

Realizing this is happening and admitting it feels like the first step. More importantly is what happens next.

David Cancel gave me great advice at RubyRiot that I haven’t heeded well to this point. He said, “save someone an hour a day and build a business around that.”  It also harkens back to the most obvious solution that’s been standing right in front of me the entire time: Customer Development.  Somehow, in all of this, I’ve done very little customer development (other than when helping friends’ startups).

What Now?

As a recent blog post said, “A lot of people talk about Lean Startups and customer development, but very few people really do it.” I need to get outside the f@&%ing building.

Here’s how you can help:

1) What sucks in your day to day or someone you know?

What makes you complain or you’ve heard someone say is horribly inefficient, and totally not in Web 2.0 and should be? I want to talk to you and/or them! Seriously, even if we don’t know each other, drop me an email at evanish.j [at] gmail [dot] com and tell me about your problem.

Don’t worry if you think it’s a boring problem; I in fact prefer unsexy problems. I’m hoping to solve a problem that doesn’t have 25 Valley startups working on it.  One of my favorite startups a friend is doing (not in Boston) is working in a space where his direct competitors are…call centers. That’s a fun problem to solve.

2) Got an idea you wish existed but can’t work on?

I’ve already talked to a few of you that have shared ideas where you said, “If I wasn’t doing my startup, I would do this.”  If you find yourself saying that, I’d love to buy you a coffee or beer and see if it’s something I can help make a reality.  I’m very happy to make you a beta user ;- )

3) Hold me to this.

Whether you have a problem or know of one I can solve or not, please hold me to this.

Don’t ask me how I’m doing next time you see me. Ask me if I’ve gotten outside the building.

Motivation and Perspective

In life, you face ups and downs constantly. Choosing to be an entrepreneur means you live in a world of extremes much greater than those with the security of a 9 to 5.  Especially as a young entrepreneur who has a much simpler personal life than those with wife/kids/families, I live and die by startup life; the swings are magnified because so much of it personifies my life and determines how I measure myself.

One of the luxuries of running Greenhorn Connect is that I’ve always had it in addition to whatever my main focus was (for the last year – oneforty and now the new startup).  I’ve found that in most cases, there would be at least one victory, one good thing that always happened to focus on despite any setbacks or blows I’d also taken.

In the end though, some days I still feel more like the nail than the hammer. On these days and ones where I just want to get amped up, I turn to some key places of inspiration.

I love movies. I feel like a good filmmaker with the right story and actors can create a connection with the audience in a genuine way unlike any other medium. I also love sports.  There is no better microcosm for life. Every game and every season mirrors so many of the struggles (and triumphs) of life. It should then be no surprise that all of these are sports and film related.

The “Suck it up” Speech – Rocky Balboa

Rocky’s Speech to his son on Life & Fighting

I watch this when I need to remember that life isn’t easy, and that “90% of life is just showing up” because the other guy will give up.

The Reason to Fight so Hard – Any Given Sunday

Al Pacino’s “inches” speech

Nothing better captures the essence of the struggle and how those little victories, and all the day to day efforts are what builds success.

Hope & Spirit – The Shawshank Redemption

Andy and Red share in the excitement and challenges of hope.

In the end, all we have is our own spirit. If you listen to it, you will get there. This is my all time favorite movie and my goto film when I really need picked up.

Remembering Greatness – Compilation of MJ Interviews

From Nike ads to long hours on the baseball field and courts, a view into MJ’s life.

Your greatest competitor is yourself, but that is how you create greatness: by demanding it of yourself and putting in the work to get there.

Drive, Passion and Dying on the Treadmill – Compilation of Will Smith Interviews

This video made me a fan of Will Smith for life and never doubt another film he’s a part of.

I love Will’s line, “If we got on a treadmill together, there’s 2 things: You’re getting off first, or I’m going to die.” You either find this disturbing or you understand me.

It feels like my life can be summed up in one word: escalation. I’m always trying to make the next step greater than the last, the next day better than the previous.

One night, shortly after starting at oneforty, Laura Fitton tweeted asking, “What’s the one most important thing?”  I answered “Progress.” Escalation is positive progress.

When I feel like progress is backwards or I just need a reminder of what drives me, this is what I turn to.  This is what I’m about.

Torture and Culture

Thanks to the “War on Terror” the topic of torture is much more front and center than it was in the past.  As life mirrors art, I’ve noticed that popular culture has picked up on it.

In movies and television, torture has become an increasingly prevalent piece of plots. Jack Bauer, hero of the long running show, 24, has regularly used it to get answers and even supposed unexpected everyman hero, MIT educated, Sean Walker of The Event has used torture to get answers.

With real life and art showing torture so prevalently…is it any surprise that more than half of all American teens condone torture?

What’s most interesting is that it wasn’t always like that. We didn’t always glorify it or even condone it.

I just finished watching an old Star Trek the Next Generation episode that addressed torture head on and was far from supportive of the practice. In the episode, Captain Picard is captured by an alien race and tortured for answers. He refuses to break down and repeatedly discusses the ethics and effectiveness of torture. In the end, once he’s free, he admits to the ship’s counselor that after the torture not only was he willing to tell them anything they wanted, he thought he *saw* what they told him to see. (The episode is called “Chain of Command” and you can find an awesome article examining the episode on Slate here.)

As art can also mirror life, it’s well worth noting a practice from World War II. At Fort Hunt, high level German prisoners were subjected to chess, ping pong and steak dinners. Shockingly, these prisoners befriended their captors and divulge massive quantities of highly accurate information. Learn more about the incredible story here.

Our military’s practice of torture is only further enabled by our cultural embrace of its supposed effectiveness. The survey of teens shows that we may be more impressionable than we like to believe. I’m genuinely concerned for the implications of our future where the majority of people embrace practices so contradictory to our founding principles of Life, Liberty and the Pursuit of Happiness.

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

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:


  • 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


  • 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



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


  • 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


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


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…


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.


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