Fred, Brad, and Jerry have done a bunch of postings recently, and threaten to do more, sharing the VC perspective on many aspects of startups and entrepreneurship. I thought it might be interesting to share the entrepreneur’s perspective on the same subjects. I’ll try to cross-post and keep pace, but I’m already a couple behind, and I can’t crank out postings as fast as these guys can! (For reference, Fred and Brad are on my board, and Jerry as Fred’s partner is an advisor to my company, Return Path.)

Topic 1: Boards of Directors. All three have many good points. Brad says that boards come in three flavors (working, reporting, and lame duck), and that small companies need working boards which include other entrepreneurs in the industry as well as management and investors. He also advises to take good care of directors and not let them get bored. Fred calls the good ones engaged boards (interactive, candid, engaged, passionate, and involved) and says that while you can have a good company without an engaged board and even with a bored bored on occasion, to have a great business you need an engaged board. Finally, Jerry says that you should pick your board carefully and build it with some diversity like you would a management team and to avoid people who will yes you.

I basically agree with all of these points, and would add the following four thoughts for entrepreneurs:

1. Building a board can be one of a CEO’s greatest trump cards. Without being even a little bit disingenuous, you can use the “I’m the CEO and would like to talk to you about a potential board seat with my company” as an entree to meet face to face with some of the most interesting, senior, brand-name people in your industry (turns out, flattery will occasionally get you somewhere). Use this card wisely and sparingly, and always be prepared to follow up on your meetings, but take full advantage of it as a way to network. You never know what opportunities you’ll uncover along the way.

2. Don’t think of managing your Board as a burden. Communicate early and often to your Board members and make sure all big conversations and debates are pre-wired in one-to-one conversations before Board meetings, and that debates are framed and researched properly in advance of meetings. Nail the basics (reporting, financial reviews, well-crafted and easy-to-read materials sent out several days before the meeting), so you can focus the valuable meeting time on strategy, not on the minutiae.

3. Figure out how to work differently with investor directors and outside directors. VCs who sit on your board have very different interests, time availability, and things to contribute than outside directors, especially non-retired industry executives. Not all directors are created equally, and you don’t have to behave as if they are.

4. Sit on a board yourself. There’s nothing like a real-live counterpoint to make you take a step back and think about how to build and run an effective board. Find something — another startup, a nonprofit, your high school or college alumni association — to join as a board member. Watch and learn.

All that said, the most important thing I’ve found in running a board is following Brad, Jerry, and Fred’s collective wisdom about fostering an engaged/working board. Definitely don’t let them get bored on you!

I went to an amazing event this weekend. One of my close friends, Raj Vinnakota, started an education foundation about 7 years ago in Washington, D.C., called the SEED Foundation. The foundation’s first venture is the nation’s first urban public charter boarding school, located in the Anacostia section of town and dedicated to providing a college prep environment for kids who otherwise might not even finish high school in the inner city of D.C. The school has had a tremendous amount of national recognition, from Oprah, to Time, to Good Morning America, to Newsweek.

The school has now been up and running for six years, starting with a group of seventh graders back in 1998, and this Saturday, that first class graduated. Impressively, all 21 seniors are going to college, including some going to Princeton, Georgetown, and Penn. Alma Powell spoke at commencement. The event was one of the most moving things I’ve ever attended. The kids and their families were all so proud, and justifiably so.

Raj and I have followed fairly similar paths since meeting in college. Almost 100% of the same activities at Princeton, same first job after college at Mercer Management Consulting, lots of friends in common, similar family backgrounds. The only thing we have in common from the last 5 years, though, is that we’ve raised the same amount of money as leaders of our respective organizations — me for the for-profit Return Path, Raj for SEED.

Attending the SEED graduation gave me a twinge of guilt that I’m not doing something quite as overtly good for society, but it has an inspirational effect on me in two ways. First, it gave me hope for mankind’s future that people as talented as Raj are doing overt good for the less fortunate every single day. Second, it gave me lots of encouragement to build a successful company so that both the company, and I personally, can give back to society over time in other ways, both with money and with time.

Raj tells me that, now that he’s proven the model, he’s going to have a second school up and running by 2006, with more to come after that. All I can say is, good luck, and let me know how I can help!

I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field.

Is that statement true in business?

What’s an example of a “bad” win?  Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition.  Your win might not be sustainable, and you’ve put your reputation at risk.  Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems?  Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.

On the other side, what’s an example of a “good” loss?  We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model.  Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.

What it comes down to is that both examples – little league and business – have humans at the center.  And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth.  So yes, even in business, sometimes a good loss is better than a bad win.

Email Marketing Good and Bad:  Case Study Snippets

I had a good meeting this morning with one of our long-time multi-channel retailer clients who is in town for Shop.org’s Annual Summit.  Over the course of our conversation, she relayed two things going on in her world of email marketing at the moment that bear repeating (with her permission, of course).

First, the good.  In a recent study, our retailer hero determined that customers who receive their email newsletters and offers (not even open/click, just receive) spend on average 3x as much on in-store purchases than their non-email counterparts in any given week or for any given campaign.  Talk about deriving non-email or non-click value from your email marketing efforts!

Second, the bad (ok, well, it’s the ugly as well).  Our retailer hero was just nailed by Spamhaus because someone out there complained about a transactional email he or she received from the retailer.  She estimates that the poor Spamhaus listing is costing her millions of dollars a year in lost sales from regular customers.  The email was literally about a refund that the retailer owed the customer (why there was a complaint — who knows?).  What did Spamhaus suggest the retailer do?  Repermission their list around transactional messages — “or else.”  Seems to me that that’s a pretty tough stance to take on rather shaky evidence and with no appropriate dispute resolution mechanism (e.g., one that’s not just tuned to mailers’ interests, but one that’s fair in the broadest sense of the word).  No wonder Spamhaus is being sued, and no wonder the vigilante blacklist providers of the world are losing traction with ISPs and corporate system administrators.  Authentication and real, professionally run reputation systems with ample amounts of representative data, feedback loops, and dispute resolution mechanisms will ultimately win the day over the vigilantes of the world.  Folks like Spamhaus can get things right lots of the time and in fact do provide a valuable cog in the global world of spam fighting, but they’re less great at making amends when they don’t.

So email continues to have its challenges around filtering and deliverability…but how cool is it that marketers are really sinking their teeth into metrics that prove how effective the email channel is for driving sales, both online and offline?

In my personal life, I have acquaintances, I have friends, and I have good/close friends.

In my work life, I have colleagues – the professional equivalent of acquaintances.

But what comes after that professionally?  We spend over half our waking life at work.  Of course we are going to build important relationships.  Some of them will cross over to personal and become legitimate “friends” or “good friends.” I always feel some sense of honor when a colleague introduces me to someone as a true friend.

But for those that don’t cross that chasm – for those who are truly just professional relationships but ones with increasing closeness – what are we supposed to call them?

I guess in a pinch we could call the next level up “work friends,” although that sounds odd and a bit impersonal.  But what about the level after that?  What is a “work good friend” or even a “good work friend”?  Those sound even weirder.  And yet, “work good friends” abound!  I can probably think of 5 or 10 “work friends” or “work good friends” for every true friend or good friend in the workplace.

Has anyone found a good word or phrase for this yet?

When Good Companies Go Bad

This post could just as easily be entitled, “When Small Companies Go Big.”

I know risk management is an important part of business, but I have run into several examples in the past few months where another company’s insanely aggressive staff roles — legal, procurement, and HR in particular — have driven me batty.

We have a big financial services client who, after much wrangling with their legal time, signed a two year contract with us that was based on our standard form of agreement, though modified quite a bit to their specifications. A few months into the contract, we and our client wanted to add a new service into the agreement via a simple addendum. Someone in their legal team called us up and in a near-hysterical tone of voice told us that he didn’t think the current contract with us was valid because — even though it had an authorized signature on it and had been signed off by their legal team — it wasn’t based on their standard form of vendor agreement. So we had to start over and draft an entirely new agreement if we wanted to get the new service included in the contract.

We had another long-term client who was putting us through the paces on a contract renewal. The company had grown large enough to now have a procurement department for the first time. The renewal, in the midst of a perfectly good working business relationship, took 9 MONTHS to wrap up, during which time the client was missing out on services that the business user deemed critical.

A prospect of ours was another similar company – once small, now large, now with a procurement department. This procurement department demanded the following terms from us as a vendor: an uncapped amount of services for a fixed fee; unlimited custom modifications at no cost; and unlimited liability. When we balked (mostly because we have a brain), the procurement person called back and said “Every vendor who works with us agrees to all of these terms, always. So thank you, I’ve decided this your services are no longer a strategic area of interest for us…and please don’t call the business contact ever again without going through me.” Right, I’m sure the electric company gives these guys unlimited power for a fixed fee.

Honestly. I’m not making this stuff up. I have a lot of respect for lawyers who protect their companies. And for procurement people who are trying to negotiate a good price. But when lawyers and procurement people run the show instead of taking their cues from the business people and adding value on the margin, it’s a sign that your company has a big, big problem.

The Good, The Board, and The Ugly, Part II

Much has been written of late on various VC and entrepreneur blogs on effective management of a Board of Directors, Board materials, running good Board meetings, and the like.  A couple years ago, I even wrote out a few tips for those things myself.

But here’s one critical ingredient of a good Board you won’t find in all those posts:  have fun!  This picture was from today’s Halloween Board meeting at Feedburner…as one of Dick’s colleagues labeled it, The Dawn of the Living Costolos.

Happy Halloween!

Good Meeting Behavior

I've been in meetings with large groups of people at big companies where they're all on laptops the whole meeting, no one makes any eye contact with the speaker/facilitator, and it's hard to get a pulse out of the group as a result.

I almost entirely stopped bringing laptops and smartphones into business meetings a few years back.  There's nothing I find more irritating than when other people are using them when it's my meeting.  Even if they're taking notes, I never know if they're really taking notes or sneaking a peek at email.  And in my experience, people who are on laptops and phones in meetings, whatever they're doing on those devices and however good they are at multi-tasking, aren't paying as close attention to the meeting as the other people in the room. 

What I do instead is take notes on paper and spend 2 minutes after the meeting handling whatever data entry I need to handle on my computer.

I was very excited to see Brad's post about how he is now going to take paper notes in Board meetings rather than use his smartphone and be tempted to check email (and otherwise be distracted).  Everyone should do this for every meeting.  Board meetings are important examples, but they're not alone.  It's just good meeting behavior.  If you have other things to do, step out of the meeting and do them.

Counter Cliche:  Who’s The Dog in this Scenario?

Fred’s VC cliche of the week is a good one — “If you lie down with dogs, you’ll come up with fleas.” His point is a good and simple one, that VCs shouldn’t take people risks in deals and shouldn’t try to back management teams they have serious concerns about (ethical or otherwise) in the hopes of trying to change the team or change management.

The obvious counter cliche is that entrepreneurs run that same risk in accepting capital from less-than-savory venture investors.  An ethically-challenged investor can wreak havoc on a young company, potentially tying the company up with peripheral legal problems or even damaging the company’s attempts at raising future rounds of capital.  So, VCs can be the dog in the scenario as well.

But I think there’s a broader counter cliche here, which is that one’s reputation in business is always tied, to some extent, to the company one keeps.  This applies to investors, and also to clients, vendors, and partners.  The appearance of a connection to an unsavory character, even if it’s just an appearance, and even if “unsavory” is in the grey area instead of black-and-white, is almost as problematic as a real connection.

Our business at Return Path is a good illustration of this principle, as is the case with many companies in email marketing, since email marketing has some very visible bad guys (spammers), good guys (think eBay and Expedia), and lots of companies that operate in shades of grey in between.  One of our lines of business, Delivery Assurance Solutions (email deliverability), is particularly critical in terms of us having a great reputation in the industry, since we work on behalf of email marketers to get their mail accepted (not blocked/filtered) at major ISPs.  No matter how you cut it, this business invariably involves making some judgment calls from time to time on who’s a “good guy” vs. a “bad guy” in the email marketing world.

We try to be as clear as possible with our prospects and clients about what kinds of behavior we wil or will not accept from clients, since our reputation in this business is everything to us.  We won’t, for example, help a client with ISP relations or monitoring tools if they don’t sign reps and warrantees in our contract about their email practices that go well beyond CAN-SPAM in terms of compliance with industry best practices.  We can’t accept clients into the Bonded Sender whitelist program unless they jump through all kinds of hoops with our third-party watchdog partner, TRUSTe.  And as painful as it is from a revenue perspective, we do fire clients periodically who we discover to be either not in compliance with their reps and warrantees to us, or who we discover to have a particularly poor reputation in the industry.  All of these things are designed to make sure we stay flea-free.

One area that’s particularly tricky for us is what to do with a “bad guy” who comes to us asking for help to become a “good guy.”  While it’s hard to be completely objective about this type of situation, we have an emerging policy around it.  We WILL work with clients who the world perceives as a “bad guy,” but only on a consulting basis to teach them email best practices and how to become a “good guy” (one of my Board members, Scott Weiss from IronPort Systems, calls this Return Path’s 12-step program).  If those clients take our advice and make meaningful and measurable changes to their email programs, we will continue to work with them and will slowly allow them to use our other services over time.  If those clients resist our advice or are too slow to change their ways, we will stop working with them immediately.

I guess the point of the counter cliche is that sometimes it’s hard to tell, as Sally told Harry in the movie, who is supposed to be the dog in a particular scenario.

My dad, one of the smartest people I know, asked me a good question last week. “How’s the blog working out so far?”

My answer was generally “I’m not sure,” but as I thought about it more, I saw “good” coming from four different categories, in order of importance to me:

Thinking: One of the best things publishing a blog has done has been to force me to spend a few minutes here and there thinking about issues I encounter in a more structured way and crystallizing my point of view on them. Invaluable, but mostly for me.

Employees: A number of my employees read it, although I’m not exactly sure who since RSS is anonymous. I know this is helpful in that some of the folks in the company who I don’t speak with every day can hear more directly some of the things I’m thinking about instead of getting a filtered view from normal communication channels.

Technology: One of the main reasons I started the blog was to get more experience with blog/alert/publishing/RSS tools as I try to learn more about new technologies related to my company. This has paid off for me well so far (the technology has a long way to go!).

Business development: I have met two or three other companies who may be potential partners for Return Path through this. I also believe that the postings on industry-related topics have been helpful for both business development and PR purposes.

I promised my Dad I’d do a posting on this sometime soon…so happy Father’s Day, Pops! (I also got him a real present, don’t worry.)

Selecting Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  This is the first one…and Fred’s post on the other side of the topic is here.  Next week, we’ll address the topic of building a successful CEO-VC partnership once it’s established.

If you’re fortunate enough to have built a really strong early stage company, you will find yourself in the position of being able to pick from a number of potential venture investors.  The better your business and the more exciting the space you’re trying to tackle…the more investors you’ll find circling around you.  Here are a few tips for ending up with the best long-term partner as an investor.

1. Look for VC portfolios that have a lot of “like” companies (B2B, B2C, media, tech, etc.).  One of the strongest points of value that venture investors bring to the table is pattern matching, and you can maximize that by making sure the investor you end up with has seen a multitude of companies like yours
2. Check references carefully.  Don’t be shy – prospective VCs are checking up on you, and you have every right to do the same with them.  When Fred first invested in Return Path, he gave me a list of every CEO he had ever worked with and said “Call anyone you want on the list.  Some of these guys I worked well with, a couple I fired.  But they’ll all tell you what I’m like to work with.”  First prize is the VC who volunteers this information.  Second prize is the VC who gives it to you when you ask.  A distant third price is the VC who gives you two names and ask for time to prep them ahead of time
3. Focus on the person first, the firm second.  Having a good venture firm is important.  But at the end of the day, you’re dealing with a person first and foremost.  That’s who will be on your board giving you advice and measuring your performance.  Better to have an A person at a B firm than a B person at an A firm (of course, even better to have an A person at an A firm).  This means two things – selecting a great person to be on your Board, and also making sure you end up with a person who has enough juice within his or her firm to get things done on your behalf with the partnership
4. Always have a BATNA (Best Alternative to a Negotiated Agreement – a fancy way of saying Plan B).  This is probably the most important piece of advice I can offer.  And this is true of any negotiation, not just a term sheet.  It’s often said that good choices come from good options. Sometimes, you have to walk away from a deal where you’ve invested a lot of time, energy, and emotion.  But as an entrepreneur, you can mitigate the number of times you have to walk away by developing good alternative options to a particular deal. That way, if one option doesn’t pan out as you’d hoped, another very good option is waiting in the wings.  If you negotiate with two or three VCs, you’ll have a great backstop and won’t let the emotional investment in the deal get the best of you.  Yes, you will spend twice to three times the amount of time on the process, but it’s well worth it
5. Don’t be swayed by promises of help.  I’ve heard VCs say it all.  They’ll help you fill out your management team.  They’ll get you customers.  They’ll help with your back office.  They’re loaded up with value-add.  If venture investor has staffed his or her firm with support personnel who are available free of charge to portfolio companies (this does happen once in a while), then assume your VC will be as helpful as possible, but no more or less helpful than another investor
6. Handle the negotiation yourself, in person as much as possible.  The best way to get to know someone’s character is to negotiate a deal with him.  This gives you lots of opportunities to look for reasonableness, and to see if he or she is able to focus on the big picture.  The biggest warning sign to look for is someone who says things like “you have to agree on this term, because this is how we always do deals.”  By the way, how you handle yourself in this negotiation is equally important.  The financing is the line of demarcation between you and the VC courting each other, and the VC joining your board and effectively becoming your boss
7. “Pay up” for quality and for a clean security.  There is a world of difference between good VCs and bad VCs (both the individual partners and the firms) that will ultimately have a lot to do with how successful your company can become.  The quality of your VC isn’t more important than the quality of your product or your team, but it’s right up there.  But – and this is an important but – you should expect to “pay” for quality in the form of slightly weaker terms (whether valuation or type of security).  Similarly, I’d always sacrifice valuation for a clean security.  Everyone always thinks that price/valuation is the most important thing to maximize in a deal. However, the structure of the security can be much more important in the long run.  Whether the VCs buy 33 percent of your company or 30 percent of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join

As with all things, there are probably another dozen items that could be added to this list, but it’s a good starting point.  However, your more important role as CEO is to put your company in a position where you can select from a number of high quality investors, so start there!