Last week, Return Path announced it was being acquired by Validity

My fellow board member Fred Wilson wrote a great history titled The Long Game and Matt Blumberg wrote a beautiful tribute titled OnlyOnce, Part XX .

I’ve been involved in Return Path as an investor since 2001 when Return Path and Veripost merged as part of a funding done by Sutter Hill (Greg Sands), Flatiron Partners (Fred Wilson), and Mobius Venture Capital (me). I wrote the very long story in a post titled Return Path Acquires Netcreations in 2004. This post has a ton of Return Path history in it in case you want to go back in time 20 years. And, if you want to only go back in time 10 years, take a gander at Happy Birthday Return Path which is a post about Return Path’s 10 year anniversary and includes the story of the negotiation between me and Fred to merge Return Path and Veripost.

I count my involved in Return Path for 20 years since my investment in Veripost (which became my investment in Return Path) was done in 1999.

Today, Matt is one of my closest friends. In addition to our personal relationship, we’ve had a number of other work experiences besides Return Path. Matt has served on two boards of companies I’ve invested in – FeedBurner (acquired by Google) and Moz . Matt was an early, and engaged mentor in Techstars . Matt introduced me to Scott Dorsey, which led to our investment in High Alpha . Finally, Matt – working with Andy Sautins, Cathy Hawley, and Tami Forman – co-founded Path Forward which was spun off from Return Path.

I’m proud to have been involved in all of these companies with Matt.

Finally, Matt’s been a strong supporter of my quest to do a marathon in every state in the US. We’ve done two together – New York and Idaho .

Twenty years is a long time to be involved in anything. When a VC talks about a quick exit, you can mention that you know a few (Fred, Brad, and Greg) who has a 20-year board experience. As Fred says, “entrepreneurship and startup investing is a long game. It requires patience, resilience, capital, commitment, and much more.”

Matt – and everyone at Return Path – thank you for letting me be part of your journey.

I was an early investor in two of the first email service providers (Email Publishing and Mercury Mail). My experience with ESPs goes back more than 20 years and, since the mid 1990s, I’ve seen the ESP ecosystem evolve from its infancy, with just a few startups blazing a trail, to today’s robust industry populated by mature marketing technology platforms. And yes, they are now called email marketing platforms, which seems much more grown up and sophisticated.

Deliverability first became a hot issue in the early 2000s, and our portfolio company Return Path emerged as an innovator and leader. Since then, deliverability has remained one of the most important levers for email marketers.

Consequently, the role of the ESP’s deliverability specialist (a job, like many others in our industry, that is extremely challenging and not well known) has become increasingly difficult. Today’s deliverability specialist is tasked with managing more clients, across more geographies, with ever-changing parameters by individual mailbox providers. And of course, like any industry, they face greater and greater client expectations.

Most deliverability specialists have cobbled together their own solutions (such as MTA logs and response metrics) and leveraged solutions like Return Path – although admittedly these solutions are based on the same platform any email marketer would use. In short, deliverability solutions for ESPs could have – and should have – been better.

Recently, Return Path launched their innovative new Partner Platform solution , the first deliverability platform built exclusively for ESPs, with extensive input from their longstanding ESP partners . When I first heard of the development of this product, I was delighted that Return Path had committed to investing in an ESP/super-user platform to address the unique needs of the ESP and their deliverability specialists.

Return Path’s Partner Platform puts deliverability data all in one place, allowing deliverability specialists to see what’s happening across their entire client ecosystem. Information is layered together to provide meaningful metrics and insights across all clients’ programs.

The vast data assets Return Path has invested in, coupled with the ability to slice and dice data, is a game-changer for deliverability specialists.

This is a huge step for the email marketing industry and something that’s long overdue. I’m glad to see that an 18 year old, independent company can continue to make big innovations while growing their business.

Dealing with email is something I have become an expert in out of necessity. While it’s out of control, it’s a chore that is wired into my work in a deep way that, regardless of the explosion of real time communication channels, will likely continue to be the least common denominator for communication for the next 100 years .

That is one of the reasons why I’m interested in seeing the projects that come out of the Context.IO App Challenge , a long-format online hackathon that I’ll be judging in a few weeks along with David Cohen, Fred Wilson, Matt Blumberg and Josh Baer.

Context.IO is a product of Return Path , where I’ve been on the board since 2000. It’s an API that developers can use to build applications that integrate their users’ email data (contacts, files, messages, threads, receipts, and rule-based notifications). We’re expecting to see a healthy mix of inbox management tools along with apps that deliver value in other ways outside the inbox. A few of my favorites that have been built in the past using Context.IO are Mailtime , Paribus or Airhelp.

A common question is if projects from a hackathon can become a successful business. Not all ideas will be winners and it depends on the goals of the event and participants. There is certainly a higher chance with an online hackathon like this one where you have months to build something amazing instead of 24-48 hours. One of our portfolio companies, WootMath ,  won a similar App Challenge back in 2013.

In some ways, the judging criteria we’ll all be working from are basic questions any founder should ask themselves:

• Quality of Idea: Is the idea creative and original?
• Implementation of Idea: Was the idea well executed by the developer?
• Potential Impact: Does the application solve a specific problem or paint point for its users?
• Market Readiness: Is the application market ready?

I’m looking forward to seeing what gets built.

Matt Blumberg, the CEO of Return Path, has an outstanding post up this morning titled The Difference Between Culture and Values . Go read it, I’ll be here when you get back.

If you liked that, go get a copy of Matt’s book Startup CEO: A Field Guide to Scaling Up Your Business. It’s one of the books on my list of books all CEOs should read .

Matt distinguishes between culture and values. His punch line, which he reveals early, is:

Values guide decision-making and a sense of what’s important and what’s right. Culture is the collection of business practices, processes, and interactions that make up the work environment.

At Foundry Group, we have a slight modification to how we think of values. Supporting our values are a set of “deeply held beliefs.”  These deeply held beliefs tangibly define our values and give us a frame of reference to operate.

For example, one of our deeply held beliefs is that “we will never grow.” Each of our funds is $225 million, we have four partners and no other investment staff, and we work out of the same office we’ve worked out of since we started in 2007. We’ve had opportunities to raise much larger funds and have considered it in the past given a variety of factors. But, we kept coming back to this deeply held belief and realized that raising a larger fund would violate our brand promise of only raising $225 million funds.

Our deeply held beliefs are fundamental to our values, although we are comfortable challenging them regularly to make sure they are deeply held, and make modifications on occasion when we learn new things but only after a lot of thought and discussion, among ourselves and with several of our very close limited partners.

For example, when we started we said “we’ll make around 10 new investments a year.” This came from a belief around the importance of time diversity of investing – we have a three year time horizon for making the 30 or so initial investments in the companies we want in each fund.

Until 2013, we made between 8 and 14 a year, which is close enough to 10 (although the year we did 14 was a year where we all said “too much – slow down.”) But at the end of 2013, when the JOBS Act became official and AngelList created Syndicates, we decided to understand the phenomenon better by participating in it . So, rather than sit on the sidelines, observe, and prognosticate about angel / seed investing, we created the FG Angels Syndicate on AngelList and have done around 60 seed investments in the last 18 months.

Another example of a re-evaluation of a deeply held belief was our decision to create our Foundry Group Select Fund . Until we created this fund, we limited the amount that we could invest in a company to $15 million. We would occasionally go a little higher (the most we have invested in a company from one of our funds, other than Select, is $17 million) but, especially with successful companies, we were limited to what we could do in the later rounds. During a particularly challenging financing for Fitbit, which we believed deeply in at the time as an unambiguously successful company, we were frustrated that we couldn’t write a big check in the financing. We talked to our LPs about what we were thinking, quickly raised a late stage fund to invest on in our later rounds for our portfolio companies, and made our first investment from that fund in the last round Fitbit did in 2013. With Select, we are no longer limited to investing $15 million per company.

Matt states in his post:

“A company’s values should never really change. They are the bedrock underneath the surface that will be there 10 or 100 years from now. They are the uncompromising core principles that the company is willing to live and die by, the rules of the game.”

I strongly agree with this, although I have one nuance. It’s hard to be absolutely correct at the beginning of the journey. So, instead of being dogmatic about values you created when you were three founders in a cafe somewhere, make sure you have one layer of abstraction about how you implement them, that can be tuned over time. For us, these are our deeply held beliefs, which support our values, but can be tuned as we learn new things. But, because they are deeply held, they can only be slightly modified, rather than torn up and replaced.

I get 300+ non-spam emails a day. No matter how diligent I am at unsubscribing from stuff, I still get an endless stream of valid, opt-in email that I want to unsubscribe to. Google takes good care of my spam and they even jumped all over my complaints about their spam filtering , figured out the problem, and fixed it (thanks friends at Google). So, I’m not talking about spam, but all the rest of the stuff that I don’t need to see right away.

I’ve tried to use Google’s categories, but it doesn’t really work well for me. Others are emails I never want to see and want to unsubscribe from, but (a) it takes longer to do that, (b) trying to unsubscribe from a mobile client is painful, (c) many of my unsubscribes don’t seem to work (I just end up seeing the email again in a few weeks), and (d) the whole experience / UI is sucky.

Now, before you jump to “use a different channel than email”, recognize that I have also Slack, Kato, iMessage, Twitter, Facebook, Skype, and Google Hangouts open on my desktop with stuff hitting them all day long. Voxer lights up regularly on my iPhone, along with notifications from each of these apps. Channel proliferation has become a mess for me and one of the companies we are investors in is working on that problem earnestly.

Ultimately though I spend most of my time in Gmail especially given the amount of email I get from all different senders. It is unyielding – here’s an example from last week.

About 25% are emails that I do not need to see right away. Probably 10% are ones that I want to unsubscribe to.

OtherInbox’s Unsubscriber and Organizer solves both of these for me. Josh Baer , a long time friend and leader in the Austin Startup Community, was the co-founder. OtherInbox was acquired a few years ago by Return Path , which I’m on the board of. I used OtherInbox for a little while before and after the acquisition, but in one of my mad Gmail / Chrome plugin-performance-misery-slowdown-cleanup-fits I stopped using it.

Last fall, after playing the endless unsubscribe-to-clean-things-up-each-morning I decided to try OtherInbox again. I went all in this time. Within one week I was in email heaven.

Here’s how it works. If I want to unsubscribe to something, I simply label it “Unsubscribe” using Gmail labels and I never ever see it again. Then, OtherInbox constantly moves new emails that match certain criteria to folders. This happens automatically and in the background it figures out the organization of the emails.

I can adjust it if I want, but I’ve found that I spend almost no time adjusting it anymore. Typically, I have some unreads in there and they show up as unreads normally do in Gmail, so at the end of the day I just go to label:oib is:unread and take a quick look.

Give Unsubscriber and Organizer a try. I think you’ll find them as magical as I do.

Let’s start with a brief history of my investment-led fight against the perils of spam and my never-ending love of SMTP.

We were investors in Postini and my partner Ryan sat on the board. It transformed my life – with one minor change of an MX record some time in 2002 all the spam in my inbox disappeared. Well – it disappeared before it got to my inbox. Or even my server. The awesomeness of Postini was that it was the first cloud-based email anti-spam solution. And it was a beautiful thing that Google acquired in 2007 for $625m .

One of the benefits of our investment in Postini is a life-long friendship with Scott Petry . Scott is the co-founder of Authentic8 , which we are also investors in. Scott also sits on the board of Return Path , which is run by another life-long friend Matt Blumberg .

Scott worked at Google for three years after the transaction for Dave Girouard  (who used to run all of enterprise for Google and now is CEO of Upstart and on the board of Yesware with me) integrating Postini into all of Gmail’s infrastructure. We continued to use Postini as our spam filter (in front of Gmail) until Google transitioned all of Postini into the Google apps service.

You get the picture. There’s a nice thread through all of this SMTP, email deliverability, and anti-spam stuff in my world, both in investment and relationships. So I generally don’t think much about spam since in the past it just disappeared, or well, never appeared in the first place.

When I came home from my one month sabbatical in Bora Bora , I archived all the 3200+ emails in my inbox. If you missed my vacation reminder during that time, it said:

I’m on sabbatical and completely off the grid until 12/8/14.

I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.

If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (mary@foundrygroup.com ). She’ll make sure it gets to the right person.

If you want me to see it, please send it again after 12/8.

On Thursday, 12/4, Amy decided to scan through her email so I went to the business center at the St. Regis in Bora Bora with her and did the same. I simply started at the top and “read / archived” each of the around 3,300 emails (using the “[” shortcut). I’m a fast reader so I skimmed the emails I cared about. Mostly I just played a video game with the [ key.I might have had a tropical drink while I was doing this.

I didn’t respond to anything and just ran this drill again early Monday morning to finish up. I then turned off my vacation reminder, had Inbox Zero, and got started again.

Yesterday, I had a weird feeling that I’d missed something that I heard about in another email thread. I was procrastinating from working on the final edits to my new book Startup Opportunities (yes – I’m doing that some more right now, but I’ve got a nice empty day in front of me) so I randomly checked my Spam folder in Gmail. I never, never, never do this so I was suprised when on the first page I saw a legitimate email. I opened it, clicked on Not Spam, and scrolled to the next page, where I saw another one. And another one.

I had 5,500 messages in my spam folder since I got back on 12/8. I went through all off them – it only took about 10 minutes. I found 39 legitimate emails. Not notifications, not email newsletters – but real emails sent to me by people I often get emails from. Here’s a screenshot of the legit ones.

I did my dutiful work and hit “Not Spam” on all of them. I was perplexed and talked to my friends at Return Path who gave me some feedback.

This morning, I had 433 messages in my Spam folder. This time, they all looked like they should.

I’m hoping that this was only a temporary glitch in the matrix. However, I’ll be checking my Gmail spam folder on a daily basis for a while. Boo.

Earlier today, I got a note from Andy Sautins, CTO of Return Path , about the four year anniversary of the Boulder / Denver Big Data Meetup . Andy is a good friend and one of the really strong CTOs in Boulder. It’s pretty cool to see what he and his gang have created around Big Data.

While Big Data is often an overused buzzword, this meetup is about helping people solve data problems in new ways that allow them to build and scale their business faster than ever before.  Over the past four year over 1,850 people have joined our group with over 100 routinely attending the monthly meeting.

For the upcoming meeting, Ted Dunning will be talking about machine learning with Mahout.

If machine learning interests you, especially on larger datasets, please sign up and join on 5/21/2014 at the CU ATLAS Room 100 .

Pre-orders for the new book Startup CEO: A Field Guide to Scaling Up Your Business  by Matt Blumberg, CEO of Return Path, are available now on Amazon. Matt, who writes the awesome blog Only Once (which stands for “you can only be a first time CEO once”) has put a herculean effort into writing an amazing book while running a very large company.

This is the latest book in the Startup Revolution series of books that include Startup Communities: Building an Entrepreneurial Ecosystem in Your City, Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur, and Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist.

I’ve worked with Matt since 2001 when I joined Fred Wilson and Greg Sands on the board of Return Path . At the time I was an investor in a company called Veripost that was a direct competitor with Return Path. Fred was an investor in Return Path. Each company was about 20 people. The founders knew each other well and were in a brutal competition in a market that didn’t yet exist. They decided they wanted to join forces, Fred and I cut a deal over the phone in 5 minutes , and Greg Sands (at Sutter Hill at the time) led a financing round that set a price for the combined company.

Twelve years later Matt is still Return Path’s CEO. George Bilbrey, one of the Veripost founders, is the President. They are incredible partners and Matt is still a first time CEO, but now running a 400 person company that dominates its market.

The book is broken up into five parts:

• Part I: Storytelling
• Part II: Building the Company’s Human Capital
• Part III: Execution
• Part IV: Building and Leading a Board of Directors
• Part V: Managing Yourself So You Can Manage Others

Matt  has the entire outline of Startup CEO up on his blog. As with all books in the Startup Revolution series, it combines practical experience with advice with stories with commentary from other experts.

I think Startup CEO  is going to be a must read for any CEO. Do Matt a solid and go pre-order it today.

Over and over again people talk about transparency. Many people assert they are transparent, or are being transparent. Few actually are.

I was thinking about this last night while watching the last few episodes of Revenge: Season 2 with Amy. Suddenly the word “transparent” started being thrown around by the Grasons, referring to their new found desire to be transparent. In this case, it was simply disingenuous – they are transparent only when it suits their purposes and usually as a setup of some other nefarious act they were about to perform (or had performed).

Whenever a word makes it into a TV show like Revenge, you know that it’s lost all meaning. And, as I’ve observed in the world of tech and startups I play in, transparency is used all the time to justify something, but rarely actually supported by behavior.

In the “everything that is old is new again” category, the master of transparency, and likely the originator of “open book management “, is Jack Stack . I remember meeting Jack and hearing him talk at the very first Birthing of Giants event created by Verne Harnish in 1991. I read Jack’s book – The Great Game of Business: Unlocking the Power and Profitability of Open-Book Management – about his experience at Springfield ReManufacturing Corp  – and was blown away by his thinking. My first company – Feld Technologies – was definitely not run with an open book and Jack’s ideas were very provocative to me.

Over the years, several CEOs I’ve worked with have been incredibly open book, or – if you want to use today’s lingo – transparent. My two favorites are Matt Blumberg of Return Path and Rand Fiskin of Moz . Matt shares his entire board book after the board meeting with everyone at the company (now over 400 people). He’s been doing this since the beginning, and only redacts specific compensation information and occasional legal stuff. Rand shares – well everything – including one of the best, most detailed, and completely transparent posts about a private company financing in the history of private company financings.

When an entrepreneur says he’s transparent, I now ask “do you publish your board book to your entire company?” I view this as a benchmark for transparency. If the answer is “no”, then I ask the entrepreneur what he means by “I’m transparent.” If you can’t be open with your company about the information you report to your board, how can you actually be transparent?

Today, Return Path launched three new products and reframed its business as “email intelligence.” Matt Blumberg, Return Path’s CEO has an excellent post up titled Email Intelligence and the new Return Path.

Return Path is an extraordinary company that I’m proud to have been involved with for the past 12 years. At our board meeting last week, Matt gave me and Fred Wilson our 12 year anniversary gift – a pair of red Return Path-branded Adidas sneakers. I still vividly remember the phone call Fred and I had where we cut a deal to merge two nascent companies – Veripost and Return Path – in what became Return Path. We cut a deal in 10 minutes – I offered up a 50/50 merger and Fred suggested he wanted a little more since Return Path had raised 3x the money Veripost had. I responded with “how about 55/45” and Fred said “it’s a deal.”

Twelve years later Return Path is company with over 300 people, major offices in New York, Boulder, and the Bay Area, and other offices around the world. It has created and leads an entirely new category we call Email Intelligence. In 2008, after plenty of forward progress as well as some twists and turns, we finished divesting several older lines of business and focused the company entirely on a new category we created called “Email Deliverability.” As we grew, we expanded the definition to the point where the word “deliverability” only covered a subset of what we did, hence the creation of the category of “Email Intelligence.”

Matt says it extremely well in his post:

“Our solution to these problems is email intelligence. Email intelligence is the combination of data from across the email ecosystem, analytics that make it accessible and manageable, and insight that makes it actionable. Marketers need all of these to understand their email performance beyond deliverability. They need it to benchmark themselves against competitors, to gain a complete understanding of their subscribers’ experience, and to accurately track and report the full impact of their email programs.” 

I’ve been investing in and around email since my first email-related investment in 1994 in a company very creatively named “Email Publishing” which was the very first email service provider. Since then I’ve had a number of investments in email companies including Critical Path, Postini, and SendGrid. I’m psyched with the success and leadership of Return Path to date, love working with everyone at Return Path, and look forward to continuing the journey as we work to ensure that inboxes contain only messages that users want.

I love this time of year. I get up at 5am, catch up on email (holy shit – is it already 6:37?), write a blog post, go for a run, and then have a completely jam packed day full of working with amazing people. Some days are awesome, some days have crushing challenges, all of them are stimulating.

For as long as I can remember, I’ve run incredibly hot from Labor Day through Thanksgiving. The boundaries seem to be the holidays and the bookends are Amy’s birthday (9/14) and my birthday (12/1). We often find ourselves in New York around Amy’s birthday and in some exotic warm beach place (like Mexico) on mine. Between the two is complete and total chaos, which is delicious when I give myself up to it rather than fight it.

Here are a few of the things going on this fall.

• We just closed Foundry Group 2012 – a new $225 million fund. We’ll start investing out of it before the end of the year.
• Companies we’ve invested in are doing major launches. Fitbit launched two new products yesterday (Fitbit Zip and Fitbit One ), Return Path launches three today (Email Intelligence!), and MakerBot launches several magical things on Wednesday. Who needs Christmas – every day is Christmas around here.
• My fourth book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City comes out at the end of the month.
• The Startup Revolution has begun. If you wonder why this matters, take a look at this Kauffman Foundation research on The Ascent of America’s High Growth Companies .
• I’m running a marathon in Utah (St. George), Vermont (Burlington), and Michigan (Detroit) in October. This is the first time I’ve done three weekends back to back (I’ve done two before).
• Amy and I are traveling all over the United States like nomads – San Francisco, Boise, Oklahoma City, St. George, Chicago, Des Moines, Burlington, Seattle, Detroit, Boston, Montreal, Toronto, Lexington (KY), and Palm Desert. I love this country (and Canada). I’ve learned how to ship my clothes to different places – that makes the travel a lot easier.
• Amy and I are finishing up the next book in the Startup Revolution series – Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur which should be out by the end of the year.
• A second edition of Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist – which I wrote with my partner Jason Mendelson comes out, along with a teaching guide that Jason and Brad Bernthal (CU Boulder) wrote.
• I’m spending all of my extra time with my three partners at Foundry Group , who I love working with, including a top secret two day retreat, time together at Defrag and Blur, and a few magic meals along the way.

As my dad likes to say, “if you aren’t living on the edge, you are taking up too much space.” I’m enjoying the edge this semester.

If you happen to talk to Kelly along the way, tell her thanks for putting up with me. Or send her flowers. Or chocolate.

Related articles

• Launching Startup Revolution
• Foundry Group adds $225M to its venture capital pool
• Fall Semester: First Impressions.

Over the past two years I’ve been struggling mightily with the dynamics of “classical VC funded board of directors” and how these boards work. When I hear a VC say “I’m an active board member” it gives me the same nauseous feeling I get when someone says “I’m a value added investor.” I’ve been on some awesome boards, some terrible boards, and everything in between. Today, I refuse to be on a shitty or dysfunctional board and I’m proud that every board I’m on is one that I’d consider to be effective, although they all operate in different ways.

I’ve experimented with a bunch of different approaches across a lot of boards and have been thinking hard about this lately. I’m working on a book called Startup Boards with Mahendra Ramsinghani  and have done some interviews about this topic lately, including a chaotic one the other day with James Geshwiler on the Frank Peters Show .

My long term friend Matt Blumberg (Return Path CEO) and I were going back and forth about his recently board meeting (which ironically I missed) and he wrote some kind words about me and his other board members (Fred Wilson – USV, Greg Sands – Sutter Hill, Scott Weiss – A16Z, and Scott Petry – Authentic8.) I asked him if he’d write a guest post about what makes an awesome board member. He was willing – it follows.

I’ve written a bunch of posts over the years about how I manage my Board at Return Path .  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  All those topics are covered in more detail in the following posts:  Why I Love My Board, Part II , The Good, The Board, and The Ugly , and Powerpointless .

But by far the best way to make sure you have an awesome board is to start by having awesome Board members.  I’ve had about 15 Board members over the years, some far better than others.  Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.

Top 5 things that make an awesome Board member:

• They are prepared and keep commitments: They show up to all meetings.  They show up on time and don’t leave early.  They do their homework.  The are fully present and don’t do email during meetings.
• They speak their minds: They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room.  They do not come up to you after a meeting and tell you what they really think.  I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
• They build independent relationships: They get to know each other and see each other outside of your meetings.  They get to know individuals on your management team and talk to them on occasion as well.  None of this communication goes through you.
• They are resource rich: I’ve had some directors who are one-trick or two-trick ponies with their advice.  After their third or fourth meeting, they have nothing new to add.  Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis.
• They are strategically engaged but operationally distant: This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful.  Getting their operational help requires a lot of regular engagement on a specific issue or area.  But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like.

My interview/vetting process for Board members:

• Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member.
• Source broadly, get a lot of referrals from disparate sources, reach high.
• Interview many people, always face to face and usually multiple times for finalists.  Also for finalists, have a few other Board members conduct interviews as well.
• Check references thoroughly and across a few different vectors.
• Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand.  Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting.  You’ll get a good first-hand sense of a lot of the above Top 5 items this way.
• Have no fear of rejecting them.  Even if you like them.  Even if they are a stretch and someone you consider to be a business hero or mentor.  Even after you’ve already put them on the Board (and yes, even if they’re a VC).  This is your inner circle, and getting this group right is one of the most important things you can do for your company.

I asked my exec team for their own take on what makes an awesome Board member.  Here are some quick snippets from them where they didn’t overlap with mine:

• Ethical and high integrity in their own jobs and lives
• Comes with an opinion
• Thinking about what will happen next in the business and getting management to think ahead
• Call out your blind spots
• Remembering to thank you and calling out what’s right
• Role modeling for your expectations of your own management team
• Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative.  Then get out of our way
• Offer tough love…Unfettered, constructive guidance – not just what we want to hear
• Pattern matching: they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching. To really get into the essence of the issues and help give strategic guidance and suggestions
• Ability to down 2 Shake Shack milkshakes in one sitting
• Colorful and unique metaphors

Disclaimer – I run a private company.  While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary.  And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture.  That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!

I can’t remember when Angela Baldonero joined Return Path , but she’s been there for as long as I can remember. I invested in Return Path eleven years ago at the very beginning of its life. Today it is a profitable, 250 person company that is growing quickly, dominates its market segment, and is an awesome place to work. Angela has been a big part of both hiring many of the people and orchestrating the culture of the company so I very much value her point of view on interviewing. I hope you do also.

Everything is data. The candidate’s responsiveness during the interview process, how the candidate treats the admin staff, and the candidate’s ability to communicate is data. Are you interviewing someone for a tech leadership role who doesn’t have a skype account? Data point. Do you fly a candidate out for interviews who then nickels and dimes you on expenses? Data point. Does your candidate send a thank you note? Data point. Is it well written and specific or a lame generic note? Data point.

Give the candidate feedback and see what she does with it. People are wiggy about feedback. Someone who is self-aware and mature will take it in and own it, then makes sense of how she had that impact. An immature person will get defensive or refute it.

Never sacrifice your culture. Highly qualified yet bad attitude hires wreak havoc with your culture, suck up a ton of management  bandwidth and ultimately don’t get anything done. It doesn’t matter if the candidate has cured cancer or invented Jell-o. An asshole is an asshole. Fiercely protect your culture.

People can’t help but be themselves. The interview process is flawed. People are “acting” in order to get a job. You want to know how this person really is to see if they’re a good fit at your company. Interviews take time and people can only fake it for so long. If they’re “putting on a show” in the interview process, that will eventually be revealed.

Give you candidate something to do. This creates a bit of productive stress and shows you what they’re made of. For example, ask a sales person to do a presentation.  We’ve axed many sales people because they fell apart during the presentation.

Fred Wilson had an excellent post up this morning titled Social Media’s Secret Weapon – Email . I completely agree that email is the key communications channel for social media and have written about this before in posts like 100% Click Through Rate , Email – The Original Social Graph and Email Is Still The Best Login .

I’ve been investing in email related stuff for over 15 years going back to Email Publishing, my very first Boulder-based investment which I believe was the very first email service provider (ESP) and was acquired by MessageMedia which was then bought by Doubleclick. Fred and I are both investors in Return Path which he calls out in his post as the category creator and market leader in email deliverability. I love Return Path as a company and am incredibly proud of what they’ve done as a business.

My partners and I have continued to invest aggressively in what we believe is social media’s secret weapon which we refer to as the comm channel in a hat tip to the TV show 24. In Fred’s post, the comm channel is email. Our investment here is in SendGrid , a company that came out of TechStars Boulder 2009 and is one of the white hot companies in Boulder. They directly address the problem Fred describes which every software developer knows is a pain in the ass, uninteresting, hard to do well, but needs to be done right. Every web app sends transactional email – rather than build all the code yourself, just let SendGrid to it. They are now doing it for over 24,000 companies, sending out over 60 million transactional emails a day, and just sent their 10 billionth transactional email.

But email isn’t the only comm channel. Everyone that uses apps on a mobile phone is likely experiencing push notifications as an increasingly important as a form of engagement. While mobile phones used to only really work effectively with SMS, you now have SMS, email, and push notifications. So we invested in Urban Airship who does for push notifications what SendGrid does for email. Like SendGrid, they are growing like crazy, are in use by over 10,000 customers and have sent over 3 billion push notifications.

My message to all web developers – if you are serious about what you are doing, focus on your app. Don’t waste precious development time on all the activities around the app. You likely no longer sit around with a screwdriver setting up a server in a datacenter – instead you are using a cloud provider like Rackspace or Amazon.  Don’t spent your time coding up an email notification infrastructure – use SendGrid . And if you are a mobile developer, don’t waste your time writing a bunch of code for push notifications – use Urban Airship.

Most importantly, don’t ignore the thing that will actually make your web app get adoption and retention – comm channels!

My long time friend Matt Blumberg , the CEO of Return Path , wrote a blog post today titled A New Kind of Partnership for Return Path. In it he talks about his recognition, as Return Path has grown (they are now around 250 people), of the gender imbalance in the software engineering team (women are around 15% of total engineering team.. He knew about NCWIT from my role as chairman and Matt and his team decided to join the NCWIT Workforce Alliance to engage in helping address this issue.

Matt and his team then did something that blew me away. They provided the sponsorship of the first-ever NCWIT/Return Path Student Seed Fund. This will program will provide seed funding to groups of technical women at universities across the US to advance the goals of women in computing. There are so many things about this that are exciting to me, including the focus on students, seed funding, and the linkage to NCWIT’s overall goal.

We’ve got a huge NCWIT announcement coming in a few days that Return Path is also involved in as one of the founding members. I’ll post more about it, why it’s so important to me, who’s involved, and what you can do to engage – probably over the weekend.

Return Path – thank you!

A week ago I had just gotten home after a month in Homer, Alaska.  I was totally chilled out – I worked plenty in July but had very little physical human interaction with anyone other than Amy.  I’m sitting here in my Boulder condo today thinking about the entrepreneurial tour de force that was the last six days.  I think I interacted with more different people each day than I did cumulatively over the previous 30 days in Homer.

The Boulder New Tech Meetup double header (Tuesday and Wednesday) started things off.  The second Boulder Open Angel Forum delivered.  Then we had TechStars Demo Day which was amazing, followed by an Open House at Jive Software (they acquired TechStars Boulder 2007 company Filtrbox last year and are growing like crazy), a Return Path board dinner at Black Cat, and the the TechStars Afterparty at the Draft House.  Friday saw a Return Path board meeting and lunch with the folks at Return Path followed by TEDxBoulder on Saturday.  Oh, and in between I had piles of “regular work.”

There were numerous blog posts and tweets from the week, but my favorite post about an event from the week is up on the True Ventures web site titled On The Road With TechStars Boulder .   In addition to all the locals, there were a huge number of folks from out of town who participated in the various events and I smiled a big smile when I read the post.

Last night during the TEDxBoulder intermission break, I had a few quiet moments to myself as I wandered around the grounds of the Boulder Chautauqua .  I was filled with a deep satisfaction about the amazingness of the people of Boulder.  While there are lots of other great places in the world, I am most at home here.  And it’s good to be back home.