reecepacheco

Being a player/coach isn’t easy, be it sports, business or life in general.

Last weekend was the annual Cape Cod Lacrosse Tournament. For the past four years, my buddies have registered a team and I just showed up to play. I did my part to lead on the field, but I didn’t feel responsibility as a coach.

This year, I stepped it up. I designed our jerseys (and picked the team socks!), worked on the roster a bit more, communicated to everyone, decided the starters, influenced our style of play, (even took some videos to thank our sponsors) etc… all while trying to play defense and have a great time with friends I only see once a year.

It wasn’t easy.

I’m competitive and I like to win. Last year, we did not win (the championship, nor many games). This year, I was determined to change that.

But in the process, I realized it’s a really tough position - being a friend, a teammate and the coach. I wanted to win and yet I also wanted all my buddies to get plenty of playing time. I wanted to coach, but I also wanted to just let my team play the game - purely and free - the way it’s meant to be played.

I know I blatantly made some mistakes as a coach (and as a player!), and it was scary in Game 1 when we lost badly, but I’m really proud to say we won every game after that to bring home the 2010 Championship!

I think the winning formula was a balance between leadership and letting go. When you put the right team together, give them a problem to solve and the tools and trust to do it… good things are going to happen.

And really important, we emphasized having fun on the field. The team we beat was swearing at one another by half-time, while we coolly joked about the previous night’s shenanigans. 

The best compliment on the weekend though was this: 

I heard a lot of people on the sidelines saying how funny you guys were and how much fun you all were having during the game…must be legit if you can have fun and win at the same time!

Be passionate about what you do, have fun doing it and it’ll never seem like work. While I know I learned a lot of this through my career in sports, I’ve had a similar experience in business.

When we started working on HomeField, I know I had a tendency to micro-manage, which isn’t great as a friend, co-worker or ‘CEO’ to my cofounders, Dan and Joe, and our new guy, Henry. But I’ve learned to let go and the results have been phenomenal. It wouldn’t be possible without the trust that we all have with one another.

This week, we’re in my hometown on Cape Cod to get some great work done on HomeField, but also to think big and have fun building a great company together.

So here’s to Beach House Lacrosse - the 2010 Cape Cod Lacrosse Champions - and to my buddies - Dan, Joe, and Henry - for being awesome teammates, letting me be a player/coach.

[Photos by Leslie].

Yesterday, I tweeted this:

Apparently, a few people patriotically agreed with me.  (Thanks for the retweets!).

It’s a simple analogy and it’s probably been made before, but as I went for a run yesterday I was thinking about the decisions and actions made by our founding fathers to start this country, and I quickly began imagining the excitement and uncertainty they must have felt at that time.

Nowadays, starting a company is every bit as exciting, but thanks to widespread media and connectivity - the story’s been heard before. There’s no perfect roadmap, but there’s a rough framework: start with an idea, work hard, and go from there. You can even Google it.

But these dudes were starting a whole new country! Think about the leap of faith they had to make to go from everything they’d known to “we’re doing this our way from now on.” They certainly couldn’t Google “how to start a country”. BADASS.

Let’s face it, America is a business. There are all sorts of cool analogies we can draw from its history… in the Civil War the founders almost broke up the band, in the Cold War we got in a feature race to take over the market… but I’ll leave it here for now and just remember that those original starters - the founding fathers - laid down a great framework for free enterprise that lets me and my cofounders work on HomeField today.

Thanks for that, guys. Happy America Day.

July?! What happened to June? Oh yeah, I traveled so much that I literally didn’t stay in one bed for more than 3 days at a time!

Any VC’s reading this are already thinking “cry me a river.”  Trust me, I’m not writing to complain. In fact, I loved it! Sure it messes with my work/sleep/diet/exercise routines, but I got to meet some awesome people - and as I’ve said before, it’s best to make connections early and often.

I’m just going to tell you about the highlights (and the coolest people!):

Hanging with our investor Allen Morgan and his family, our fellow Brown online-video entreprenurs from Wistia, and our former professor in engineering and entrepreneurship at the Brown Campus Dance (Providence, RI) for my 5th reunion!

Meeting Larry Probst - former CEO of EA Sports, current US Olympic Committee Chairman and just an awesome guy!  We had a great discussion about HomeField and he’s made some intros for us already.

Out to Seattle, and more specifically Gig Harbor for Mark and Aubrey’s wedding (click for pics).  Such a fun time and a beautiful area (look at that sunset!)

I made it back to NYC for a meeting with Peter Horan (another great, smart guy) and then took off for LA for a few angel meetings and more importantly - a meeting with the head of Yahoo! Sports, Kyle Laughlin. I like their thoughts for the future and am excited to work with them going forward.  And of course it was great to crash with my study abroad buddies Mike and Rafe! We had dinner at Wurstkurche in Downtown LA - if you like beer and bratwurst, and Belgian fries - you gotta go!

Then it was back to the East coast for a meeting with serial entrepreneur Chris Hassett on… Cape Cod? Yup! Who knew I had a successful veteran entrepreneur in my hometown?!

Took a quick trip to BOS to meet with Todd McCormack - angel investor and super smart exec at IMG - then back to NYC for a bunch of meetings, but particularly productive was catching up with Matt Minoff, CEO of Nabbr, and then Andrew Montgomery at Mesa Global.  Both really sharp young guys navigating this tech/media world well.

I made it back up to Cape Cod for the weekend so I could work a party at my parents’ restaurant in celebration of San Juan’s Day (a popular holiday among the Portuguese). Such a fun night!  (That’s me in my Azorean soccer jersey with my Vavo!).

Another quick trip to BOS after that, this time to meet Dustin Dolginow of Atlas Venture. For a “junior guy” at a VC firm, Dustin already shows lots of promise. He started out as an entrepreneur, so he knows what it’s like being on my side of the table, and he listens well so he can understand the problem, the market and the potential.

Back down to NYC again for meetings with Pat Battle - top brass at Collegiate Licensing Company which later sold to IMG where he now heads up their college division. Even though we met in a busy midtown hotel lobby, we had a great chat about sports media and business.

Then I headed over to RRE to meet with Eric Weisen. I’d seen Eric’s name on AVC.com comment threads and always appreciated his thoughts, but had never met him. Glad I did. Eric is smart, realistic and straightforward without being a know-it-all.

Finally, I got back to Cape Cod - home sweet home - and spent a couple hours at the beach with my sister a.k.a. @OmGal talking about strategies as she builds her personal brand at OmGal.com.  We took some fun pics, too!  

It wouldn’t last long though - before I knew it - Dustin Dolginow hooked me up with tickets to the Red Sox - 7 rows behind home plate, courtesy of Atlas Venture! Along with us was Jameel Khalfan of Globespan Capital and Chase Garbarino, founder of Pinyadda. Afterward, I invited my friends John Gillis (future MIT Sloan student) and Charley Cummings (current HBS student), and we all had a great talk about tech, startups, business. I can’t wait to do it again soon.

There have been countless other people I’ve met with, spoken with, danced with and more - but this post is long enough! It’s been a fun month being on the road, though I’m glad to be settled for a while so I can get some momentum going in my own work.

Finally, I have to say thanks to everyone who’s helped me out - for the intros, the lunches and dinners, events, couches to sleep on, etc. - it’s really nice to be able to travel all over the world and still feel at home.

And a special thanks to @daisyames for hitting the road with me and helping every step of the way!  (I think she’s trying to run away!)

By the numbers: Starting the last weekend in May when we went to RI AND moved Daisy from NYC to New Haven, my schedule has been: NYC, RI, NYC, CT, NYC, SEA, NYC, LA, CC (Cape Cod), BOS, CC, BOS, CT, NYC, CC, BOS, NYC, CC, BOS, CC.  

20 stops in 34 days!

I’ve met some people who work “in digital” lately. I honestly don’t know what that means. None of them seem to be engineers. They’re usually sales people. 

I’ll give them this though, they’re always looking to buy and sell ad inventory, so they usually light up when I say I’m at a web startup…

Until I tell them we don’t run ads on HomeField.

We have real customers who pay us to use HomeField because they love it. This is news to them. This is good business to us.

On a related note, I was fortunate enough to meet with entrepreneur/investor Travis Kalanick recently. We talked about HomeField. He said if I mentioned advertising as the business model he would literally walk out the door.

I liked that.

Listen, advertising works for some properties, but there’s nothing like the ‘beautiful feeling’ of getting paid - directly from a customer - for your product.

The other day I talked about Jeff Bussgang’s book Mastering the VC Game. I highly recommend this for anyone who thinks they may want to raise venture capital someday.

In the book, Bussgang includes the stories of some stellar entrepreneurs. In particular, I loved the story about Eric Paley who keenly built and successfully sold his startup to 3M.

There are a few reasons Eric was so successful, but one lesson that stuck out to me was how he developed his network early. He made the connection to Jeff as an MBA student, before even mentioning his startup. When it was time to pitch the idea, he already had a warm connection.

Conversely, when we started building HomeField, we didn’t have any connections to the world of investors. We really didn’t know much about startups at all. We just wanted to create this thing to scratch our own itch and figured we’d learn along the way.

Over time, I slowly started to hear about some of the major players online: Fred Wilson, Brad Feld, Bijan Sabet - but I still didn’t know anyone who knew them!

However, thanks to their life-streaming and my avid reading/commenting habits, I was able to develop a relationship with them through their blogs and eventually met with all of them in person (one in an office, one on a 6am run around the Flatiron District, and one on a football field. Ok, coffee first, then football).  

I’m lucky I was able to do this, but it took time to get there and I’m still playing catch-up. I wish I’d known them sooner. Hell, I wish I’d started this business before I even graduated, but then I wouldn’t have done this, this, or this.

Point is - if you think you may want to work with someone in the future, make the connection as soon as you can… and in general, make as many good quality connections as well. As I’m learning from our ‘sherpa’ Allen Morgan, they’ll pay off in the long run.

[And to be clear, I mean real connections. Facebook, LinkedIn et al. are great for research, but they don’t count.]

I finished reading Jeff Bussgang’s book Mastering the VC Game last week. It’s a great, quick read that anyone starting out in tech/startups/VC should read (especially founders planning to raise money).

Lots of rookie founders subscribe to a diet of self-education through blogs/books (often about fundraising because it’s foreign as first-timers). I sometimes refer other newbies to my Entrepreneur’s Reading List including classics like Getting Real, inspirational works like The Monk and The Riddle, and prolific bloggers like Fred Wilson and Mark Suster.

I’ll admit though, some of it turns into an echo chamber. “start building something, get traction, iterate on feedback, raise capital only if necessary, work hard, innovate…” etc. I’m not putting all this advice down, but Bussgang’s book touched on something new for me.  

…the most essential element in the relationship between the entrepreneur and the VC boils down to one word.  Chemistry.

Bussgang advocates developing a great, communicative foundation between entrepreneur and VC in order to have a successful business. By communicating early and often to develop chemistry, they can work together more harmoniously than stereotypical ‘vulture capitalists’ are known for. Furthermore, Bussgang notes that entrepreneurs cannot simply look at a VC like an ATM with a hefty fee.

I generally try to be very terse in any communication with VC’s. They’re busy guys so it’s tough to break through the noise. Likewise in any pitch I’ve had - I cut right to the chase. But in hindsight, this is too transactional. The best VC’s want to get to know the entrepreneurs and figure out how they can really help build a great business.

…and thinking back on it, the best meetings I’ve had are when I’ve ditched the deck and been the most candid about who I am and what makes me (and my founders) tick. And when the VC’s open up the same way, we can really see eye to eye and start to work together.

A lot of entrepreneurs bemoan pitching investors, but I’ve learned to love it. These guys have tons of experience and I’m excited to learn from them and work more closely together to build a great business.

There’s a ton more good advice in the book. Go read it.