Choose your own adventure. A career at ESPN

When I was a kid my favorite books were the Choose Your Own Adventure Books, where you’d read along and come to a decision point — do I take the mountain path or the jungle path.  Since my first job at RIT, I’ve always treated my career a bit like a choose your own adventure book (blog post here)— where you flip the page and a really awesome opportunity comes along and you have to make the decision to go after that opportunity — or stay the course.

I’m at that page in my book today and I’m excited to announce that I’ve joined ESPN as Sr. Director of Product and will be focused on digital products across all screens: including, Mobile (scorecenter, SportsCenter feed), WatchESPN, ESPN3 & ESPN Fantasy.  ESPN has been a big part of my life ever since the days of watching Michael Jordan highlights on SportsCenter before school.   More importantly, ESPN is an important brand in 10’s of millions of peoples lives around the world.

I’m a tech geek at heart and have always loved product — the combination of that plus the ability to create product in a huge space that i’m personally passionate about is an adventure that’s hard to turn down.  At it’s core, ESPN is a technology company with the deepest well of content and talent available in the sports world today.  Right now, ESPN is embarking on a revolutionary journey to reinvent the way that we consume, share and create content around sports and I’m super excited to be able to help contribute to that vision.

Of course, by choosing this adventure — I’m leaving something behind.  It’s been one of the greatest pleasures of  my career being a part of the Polaris family.  I’m humbled by the opportunity that this awesome group of folks gave me to learn the venture business, contribute to the portfolio and  to help entrepreneurs succeed in building some awesome companies.  I’m forever indebted to the partnership, but especially to Dave Barrett who took me under his wing and spent the time to teach the craft of venture capital to a complete greenhorn.   The guys on the tech team (Jon, Peter, Terry, Jason & Noel) are first-class and I look forward to continuing to stay involved and  working with them outside of  my day to day at ESPN.

While I won’t be as deeply involved in the community as I am today, I’ll be intently watching the tremendous renaissance that is happening in our ecosystem.  There is so much to be excited for in Boston — I’m tremendously bullish on the future & you should be too!

So this isn’t goodbye, it’s jumping to page 183 — the ESPN path.  For those that want to keep in touch, my new email is

Posted in Uncategorized | 5 Comments

Talking to the right investors — don’t push the rock up hill!

One of the questions that I get often from entrepreneurs (especially those raising seed rounds) is to make introductions for them to investors, which I’m always happy to-do.  Making GOOD introductions is a key part of my strategy to helping the start-up ecosystem thrive, and hopefully helping great entrepreneurs get one step closer to the dream of building a really awesome company.

I always ask   founders who they want to meet and why — with the WHY being the most important question.  All to often, I get a laundry list of every guy in town (which generally constitutes the teams “strategy” of ask everyone with a pulse).   Personally, I think founders are wasting a shit load of time (which they typically don’t have) and energy (that could be dedicated to actually building the business) with this strategy — and frankly — showing that they’re strategic thinking skills are, well — non existent .   There should be a base of questions that a founder asks themselves about every potential investor — BEFORE they add them to the list of folks that they want to go after.  Here is my rank ordered checklist:

1) Where are the areas that I need the most help (generally also where I have gaps in the teams skills).  Who are the folks that are known experts in those areas?

2) Using the list above, do they invest in my space (hint: look at the investments already made)

3) Do they invest at my stage?  (not every institutional investor does seed deals, for instance).  Do they invest w/ my preferred deal type (convertible note –or– priced?).

3) Are there competitive or synergistic portfolio companies (hint:  investors love synergies among their portfolio).

4) How many investments has the firm/investor made?  Do they realistically have the time to spend working with me on my business? (remember – you’ll need more HELP than $$ to build a great company — pick folks that optimize on the help side).

5)Does the firm prefer to lead/follow?  Do I need a lead investor to get them excited?  Are they betting on my seed to take a stab at the next round?  (important to know, as  you’ll want to have some idea as to how fill out your dance card for a GREAT seed round and to tee you up for the series ‘A’).

End result — spend the time up front to pare down the list to the most relevant folks — and don’t waste your time running around town pitching to folks that aren’t a good fit — time matters and it’s better spent put towards your business.


Posted in early stage | Leave a comment

Are you a River or Point person?

Over the past few weeks I’ve found myself in a bunch of conversations with people about their careers.  Some are thinking about their next immediate move and what they need to learn to get there.  Others were thinking out 10 or more years and are working on plotting the exact best route to get there.  It’s this second group that is hard for me to relate to.  I’ve never (for better or worse) been the type of person to decide what it is I want to be doing in a decade from now.

I consider myself a river person.  I believe that a river person thinks about their career a journey, making decisions at key junctions, often taking them on an entirely new and exciting course.  Sometimes those junctions are accidental, others they’ve worked towards creating.  Nonetheless, if you look at my own career trajectory, it’s easy to see I’m a river person.   It’s all about awesome experiences, new challenges and being open to moving outside of your comfort zone to learn and practice something totally new and foreign.

Point people, on the other hand define a point in the future and work carefully and strategically towards getting to that point, with little deviation along the way.  They’re purpose driven and always thinking about what experiences they need to gain to help them achieve their goals.  I’ve seen people suffer through jobs they hated, all for the experience of doing “X”.  I’ve always admired these types of people, but as a river person — I’m pretty happy.

Why in the hell does this matter?  I think it matters when talking with someone about their career, to understand what camp their in.  And if you’re a people manager — this is a critical thing for you to understand, in order to best help your direct reports grow and achieve new heights (no matter how they may get there).   I think it’s always important to share your experiences and beliefs — but I always do it with the context of being a river person.  I think it makes your advice/perspective way more useful, and less foreign that way.

Posted in career | Tagged , | 2 Comments

What I Learned From a Crappy Manager.

We’ve all seen the thousands of posts where people talk about what they’ve learned from awesome managers.  Truth is, it’s the same for me — I’ve been (and currently am!) fortunate to have managers who I’ve learned boat-loads from, have cheered me on, challenged me, believed in me, and set me on the right course when I veered off.   Over the weekend I had a conversation with a great friend and afterwards I was reflecting on the one & only horrible manager I’ve had in my career (I’ve had at least 14 “managers”, and have managed others).  I thought — there must have been something that I learned from them — it couldn’t have all been wasted time.   Or was it?

It turns out, that there was alot that I learned — and thus, thought I’d share it.  If for no other reason than to show that even the crappiest of crappy managers, can still teach us something.  Below is a short list of things I learned & hope to never repeat.

  • Don’t be absent, then be upset that team moved on with out you:

May seem obvious, but assuming you have the right team in place — let them execute.  Worst thing  you can do is disappear (physically or literally) and then parachute back into the mix.  That yo-yo effect kills momentum, and results in the team having the tail wag the dog.   Better yet, set the pace and empower the team to keep up!

  • When you recognize that the team has bonded, embrace it — don’t try to kill it:

Don’t feel the need to be part of the inner circle of the team.  Rather, be proud that they’ve come together in a really powerful organic way.  Teams that can execute at a high degree as a unified voice are wicked powerful.  Embrace (and be proud!) of this movement — it means that the team is firing on all 8 cyinders!

  • It’s OK not to be the smartest person in the room:

Making the assumption that you’ve hired the right people, let them be awesome.  You’re the manager, not because you are the resident expert of every topic from arts & crafts to deep tech — you’re the manager because you can hire awesome people and inspire them to greatness.  The more that you try and act like the cats pajamana’s, the more likely that your team will shut down and you’ll lose that precious good stuff you hired them for in the first place.

  • Past greatness, means nothing to future success:

If you have to go back more than 10 years for your last big accomplishment — don’t bother.  Worse yet, is beating your team across the head with those same stale and irrelevant 15 year old accomplishments.  Instead, focus on the future and how you’re going to, as a kick ass manager, drive the team to something awesome.  Look ahead, not behind you.

  • Give credit and upward visibility to the team:

If you’re afraid to have your team meet with your manager, ask yourself why.   Chances are, you’ve sniped some credit from the team and don’t want to be exposed.  Or you know you’re totally inept, and want to control the messaging.  Either case send shitty messages to your team, not of which are inspiring confidence in your ability as a leader.  Encourage updward dialogue, and most importantly — give 100% of the credit to the team, after all — you had the foresight to hire them.

At the end of the day, a crappy manager can ruin your day (or hell, even your career!), but I believe that no matter how bad the situation — there is always something to be learned.

Posted in Uncategorized | Leave a comment

Focus on product, not fundraising

Not a week goes by where I meet with an entrepreneur that has an all to familiar problem — “I can’t raise seed money”.  Even in this environment where it seems like everyone is pulling in $10’s of millions of funding, there are still alot of companies that are having a hard time raising seed capital.  The next statement that I often hear, is “I’ve been so focused on fund raising over the past XX months, I haven’t spent  much time on  product/customer acquisition/etc.”  When I hear this,  it always concerns me.

The reality is, they’re not listening to the market and instead of spending time on what really matters — they’ve spent their time chasing every lead, introduction, and possible funding source — with little to show (except frustration and exhaustion).  Hopefully you have a great team with really relevant experiences, and  there are a few entrepreneurs that can raise money based on reputation alone, but chances are — pretty slim.   So what’s my advice?  It’s simple really:

  • Stop spending all of your time on fundraising.
  • Listen to the feedback — silence is deafening.
  • Focus your time and energy on building a disruptive and compelling product & start to get data to show validation.
  • Great product and some traction, the funding will come to you.

What should traction look like?  It doesn’t have to be 6 months of data, or millions of users.  It should be directional (IE: does the slope of the line head the right way with a 3 or 4 key data points).  Your goal is to have a thesis (not all of the answers), start to understand whats working and what’s not, and what levers you need to pull to make the business head in the right direction……yup, it’s all about reducing risk!  A few key data points I’d think about (and I always ask about!) and be able to show data against: (Note: not all are always applicable)

  • User acquisition rate and source (can you acquire users and are you buying them, or are they organic?)
  • Of those users, what is the daily/weekly/monthly actives (registered users alone, is totally uninteresting w/o this data)
  • Unit economics and conversion of free to paid users? (can you build layers of services on top of a freemium model?)
  • What’s the cost of acquisition?  LTV of a customer?  (ideally you’l show cost going down, value going up)

You shouldn’t expect to have mountains of data, but the more data you can provide — the better.   What creates compelling data? Great product!!  If you’re struggling to fund raise — Focus on a building a compelling & disruptive product, the fundraising will complete itself.

Posted in dogpatch labs, early stage | 1 Comment

390 days of WinPhone7, and now onto the iPhone4s. A comparison:

A little over a year ago when I was still working at MSFT, I couldn’t wait to get my hands onto the new Windows Phone.  A year later, and alot of abuse from friends & colleagues I’ve moved onto the iPhone4s.  I have to admit, the Windows Phone was a great leap forward over the previous OS’s and all in all — I’d recommend it to anyone who is in the market for a great device.  FWIW, I feel like most comparisons are by folks that have spent 15 minutes with the Windows Phone, after more than a year as a heavy user, I thought I’d share my thoughts 🙂

Where Windows wins (Mango build, on Samsung Omnia):

  • Live tiles and home screen are a slick and intuitive way of getting me the right information at a glance.
  • Keyboard is bigger and more responsive to my meat claws.  Why in gods green earth do I need to shift to get to common punctuation?
  • Zune software.  There I said it, I miss the all you can eat music (connected to my shazzam app) feature on my windows phone.  Trying to replace this with spotify on the iPhone, but still not there yet.
  • Facebook integration is freaking awesome.  Type in a contact, and automatically see everything I need for that person.  Don’t have someone’s number in out outlook contacts?  No problem, if it’s in facebook — you’re set.  Facebook integration is the MOST underrated feature in the windows phone, and is what I miss the most.
  • Camera button.  Seems dumb, but I found myself wanting the camera button a bunch of times this weekend.  I HATE unlocking my phone to snap a picture.

Where the iPhone wins:

  • App ecosystem — hands down.  I have 4 pages of apps that I’ve downloaded in a week.  Most importantly, I can test drive app’s for Dogpatch companies, friends, etc.  This was the #1 reason I made the switch — I simply needed to be on the platform where innovation is happening.
  • Hardware.  Say what you want, I love the look and feel of the apple hardware.  For a chubby non-cool kid, having the iPhone makes me feel cool again.
  • Bluetooth sync.  It actually works flawlessly with every bluetooth device I own (including the Sync system in my Ford Truck — which is a MSFT product).  I had 10% success at best with the Windows Phone syncing w/ bluetooth devices.
  • Siri.  Siri rocks.  I could never get the Tellme application in my windows phone to understand what the hell I was telling it.  After a few hundred tries, I finally got it to understand one saying “WTF, you’re a piece of shit”.   Great youtube video of a side by side comparison.
  • Camera quality is magnificent.  I’ll never feel the need to own an actual digital camera ever again.  Now only if they made the camera more accessible and usable from an out of pocket state.

A little more than a week into the iPhone, and I really love it.  I do miss a bunch of features from my Windows Phone, and it was my last piece of nostalgia from a 5 year career at Microsoft.

Posted in technology | 1 Comment

Some Thoughts After A Few Days in NYC

I type this as I’m heading home on the Acela, after spending a few days at dogpatchlabs in NYC.  I’d spent alot of time in New York when I was with Microsoft, but never with the start-up lens on.  After 24 hours, I’m pretty excited about the community there.  It feels like everyone is working together, towards this common goal of making shit happen — and that’s a goal I can get behind.

I was most excited about the pre-SXSW meetup that folks at Hashable put together.  An event with a single goal — Help every company that is launching a product at SXSW nail it.  About 20 companies did a 2 minute pitch so we all knew what they were launching, gave deets on how best to help them, and took feedback from the audience (about 120 people in attendance, all whom are attending SXSW).  I really loved the rallying of the troops and most importantly — the support that folks were getting.  I was pretty impressed with a bunch of the companies that were presenting, and with the overall large number of people schlepping down to Austin from NYC for a week.

Here’s the website and details about the NYC mafia that’s going to be at SXSW:

I’m really looking forward to spending more time in NYC and am more determined to findways to try and link Boston and NYC together — it’s crazy not to think about all of the synergies that we could/should be taking advantage of (and perhaps, saving Vivek Wadhwa from telling us all how much we suck, again)

Posted in dogpatch labs, early stage, Uncategorized | Tagged , , | 1 Comment

3 Things that Make Great Dogpatch residents

On my flight this AM to Austin (sans wi-fi) I had a moment to reflect on the past few weeks that I’ve been at Polaris. It’s been a really awesome month, and I’ve met a bunch of GREAT companies, entrepreneurs and have learned more in the past month that I ever though imaginable (thanks to some great mentors like Dave Barrett and Ryan Spoon).    A big part of what I’ve been focused on is getting Dogpatch moved into the new digs at One Cambridge Center (6th floor), and also recruiting new companies to come and join the DPL community.

At the earliest stages, every company is missing something (key hires, traction, funding, etc) and it’s our hope that creating an open-source and collaborative community within DPL provides fertile ground for companies to find the chocolate to their peanut butter.  It’s also worth mentioning that the goal of DPL is not to create deal flow for Polaris, but rather that every DPL company receives funding from someone.  Just in the past month, several DPL residents have announced they’ve closed funding – which to me, is success.   Based on that, I thought it worthwhile to list out a 3 things that I think make great residents in DPL (and thus, make a great organic community)

1)      Willingness to be collaborative. DPL is purposefully a mix of companies across stages (some just putting finger to keyboard, others having raised funding), which means that as you’re heading to your next mile post, someone else has probably just crossed that same mile post and learned something along the way.  The community only works at DPL when everyone is willing to share successes and failures, and everything that was learned while getting there.   Whether it be sharing data about which angels to talk to, helping solve technical problems, or sharing a success (or failure) with other likeminded folks – the Dogpatch community is truly about collaboration and openness.

2)      Knowing that it’s OK to ask for help.   Following on the point above, it’s hard for another entrepreneur to help, if you don’t ask.  I subscribe to the theory, much like what the teachers used to tell us in middle school – there are no embarrassing, dumb, or useless questions.  Run into a wall?  Can’t see the path ahead?  Haven’t closed that million dollar seed?  Need to figure out equity?  Ask the DPL community – I’ll bet a coffee (or beer) that someone has experienced a similar problem and is more than willing to spend an hour to help you.

3)      Actually spending time at DPL. If you’re not there, how do you take advantage of the all of the other great folks that are part of your DPL brethren?  If you’re not willing to spend more than a day or 2 a week at DPL, then you’ll probably not get much out of the experience.

If you can’t tell, I’m really really excited about where Dogpatch is heading, and if you’re interested in joining, send me a note (, catch me at an event, or stop by DPL office hours.  I’d love to chat, hear about what you’re up to and tell you more about Dogpatch.

Posted in Uncategorized | 1 Comment

DART Boston Family Dinner — Call to Action!

Last night I had my first official appearance as an EIR at Dogpatch Labs, attending DART Boston’s family dinner at the Bee Hive in the South End (sponsored by David Chang VP Products,   I had the honor of being a mentor along with the like of Bill Warner, Rob Go, Reed Sturtevant, Ty Danco, Eric Paley, and a few others, and Victoria Song did a masterful job of finding 40 young entrepreneurs to join us at dinner.  I left this dinner so energized I felt like I could have sprinted all the way back home!  While I’m not sure how much help I provided my table, they certainly did a great job of helping me understand some of the dynamics for young entrepreneurs.   Here’s who joined me.

Casey — CEO of DealGator, which is a FlashDeal aggregator, started in August and launched in December.   They’ve got a solid user base, are adding cities and have created a lot of buzz.  They’re bootstrapped and have 2 employees.

Lida — CEO of AlwaysonTechnology.  Lida created an app, Cloud Browse which enables full desktop support (+ flash +java) for iPhone.  Has close to a million users, is bootstrapped and has 1 employee.

Mark Bao — Just sold, and proved that you can build something interesting,  get viral traction and sell quickly.  Most interestingly — he’s a fulltime student and Bently, and is my accounts already a serial entrepreneur.

Here’s what I observed, in no particular order.

  • All 3 of these entrepreneurs are running pretty successful companies, making money and none have taken (or needed!) any funding. 
  • All 3 of these guys went to school in/around Boston.
  • All 3 have products based fully in the cloud.
  • All 3 are working out of their apartments.
  • Their biggest complaint is that they have a hard time meeting people, and that there are not enough events for them with the content (they don’t need a talk on funding or founding)!

Besides getting really excited about what these guys are up to, it cements for me a couple of things:

  • Lack of funding is not as big of a blocker of entrepreneurship in Boston as some would believe.
  • It’s all about the cloud and Ruby on Rails.
  • We’re leaving money on the table by not doing a better job of connecting with and supporting students (note: none of these guys went to Harvard/MIT).
  • Small gatherings like Dart’s Family Dinner are REALLY impactful and important (first time at this event for all 3 of these guys)

Here’s my call to Action for every VC, Angel, successful entrepreneur and mentor in Boston!

Get off your ass, and dedicate at least 2 nights a month to spending time at something like a DartBoston family Dinner, having office hours at local campus, or pulling together your own small & targeted gathering of folks to spend an evening helping make sure that entrepreneurs like Lida, Mark and Casey can grow a billion dollar business here in Boston.  There’s no magic, no secret sauce — just dedication, openness and a willingness to help.  Not sure where to start?  shoot me a note and I’ll help, or contact Victoria, Cort, or Jason Evanish — who I’m sure will help get you going.

Posted in dogpatch labs, early stage, Uncategorized | Tagged , , | 5 Comments

A New Path Ahead — Becoming an EIR at Polaris Venture Partners

December of 2008 I stepped foot for the first time into the Boston Innovation Community (and also into NERD!).   For those of you who don’t remember, Fall of 2008 was when the world stopped turning, and the innovation ecosystem in Boston was a barren landscape.   At the same time, Microsoft made a huge investment in Boston, opened NERD and made it a key part of the charter to help catalyze and grow the Boston technology and innovation ecosystem.  I had the privilege to work with some awesome folks on this really important project.   immediately we saw how NERD could be helpful and opened the doors, invited the community into our home, and invested in groups/projects/ideas  that could add value to the community.

Fast Forward 2 years — NERD is a bustling hive of activity and has become a keystone to the innovation community.  I’m tremendously proud of all of the work that we’ve done (a lot of which was just feeling around in the dark), and how much I believe we’ve been able to help make Boston a better place for students, entrepreneurs, technologists and of course — beer and pizza companies.   While  there is never a good time to move on, and leave behind something as amazing as NERD, I feel great about the path that it’s on.  You shouldn’t expect to see anything differently from NERD.  I was a part of an amazing team and I expect them to fill in right behind me and continue to be an awesome community enabler and partner! 

I’ll be starting next week at Polaris Venture Partners, and will be working out of the Cambridge Dog Patch lab.  You’ll still see me at every event, gathering and party in the community!  I’m really excited to be able to really roll up my sleeves and continue to help launch and grow new companies in Boston.  Dog Patch is an amazing community of entrepreneurs and innovator (across all 3 cities!) and I can’t wait to hear your thoughts on how to make it a bigger and better part of the ecosystem.  There’s still a lot of work to-do in Boston, and my resolve to make the ecosystem better is as strong as it ever has been.  My new email is and I’ll be working out of the current Cambridge DPL.  Stop in, say hi or shoot me a note — as always, coffee (or beers!) is on me!

Lastly, thanks to everyone for your guidance, friendship, support, and for welcoming a relative outsider into this phenomenal community!   Here’s to an awesome 2011!

Posted in career, dogpatch labs, early stage, Uncategorized | Tagged , , , , | 5 Comments