That’s not just the title of a mediocre 1980’s sitcom starring Tony Danza, it’s a question I get periodically, including last week in an interview. A writer I know is working on an article on entrepreneurship and asked me, “Before you started your own business, how did you like working for other people?”

The question made me think a little bit. I know what she was asking — how I liked being the boss instead of working for one — but the way she phrased it is interesting and revealing about what it’s like to be a CEO. One of the biggest differences between being in a company and starting or running one is that you’re not working for a person, you’re working for many people.

As CEO of the company, I work for a Board and shareholders, I work for our customers, and I work for our employees. That’s how I approach the job, anyway.

Return Path’s Board of Directors is my boss, even though I’m one of the people on it. I report to the Board, and the Board is responsible for hiring and (hopefully not) firing the CEO, so technically, that’s my boss. The Board is also made up (for small private companies, anyway) of representatives of our biggest shareholders. As the main owners of the business, they are concerned with the growth, profitability, and overall health of the company, and they want to make sure we are building shareholder value day in, day out. That’s one very important perspective for me to have every day.

But I also work for our customers. I have to see myself as serving them — and more important, I have to steer the organization to believe that our customers are at the top of our food chain. If I do, then things will go well in the business. We will have the right products in the market at the right time to bring in new accounts. We will have a tremendous service delivery organization that wows customers and keeps them coming back for more. We will beat out our competition any day of the week. We will keep people paying our bills!

Most important, though, I work for our employees. This is very simple. An organization thrives because the people who make it up come to work inspired, focused, and productive. When they don’t, it doesn’t. I can’t wave a wand and make everyone happy all the time, but I try to focus a significant part of my time on making sure this is a great work environment; that the managers and executives are religiously focused on developing, managing, and motivating their teams; and that we’re doing a good job of communicating our mission, our values, and why each person’s job is important to the cause. This one’s the hardest of the three to get right, but it’s worth the effort.

Certainly, I don’t respond to each of my “bosses” every day as I would a direct supervisor, but in the long haul, I have to balance out the needs and interests of all three constituencies in order to have the organization be successful.

When Do You Hire a Real Head of Sales?

A fellow entrepreneur I’m friendly with who’s got a really early stage company asked me the other day when he should hire his first head of sales.

I think the answer completely depends on what kind of business you’re in and how dependent it is on external relationship building, and also what kind of entrepreneur you are. But I tried to distill my answer down to three things for him to think about:

If your company requires a meaningful amount of customer participation before your initial product is launched, you need to invest in sales months ahead of anticipated revenue. This was the case for us at Return Path. We hired our first head of sales five months before our anticipated launch because we needed to have 10-12 beta customers on board in order to have a successful launch.

If you can wait until your product is developed and ready to ship before selling it, you can afford to wait longer if you’re handling early market development and requirements yourself. However, when you find that you don’t have time to call back interested high value prospects within a single business day because of competing priorities to get your business off the ground, it’s definitely time to bring someone in. This is especially true if you’re in a buzz business where you have prospects calling YOU to ask if they can try out your product or service.

Finally, in either case, the trick is timing. The moment you actually need a head of sales is too late to start looking for one, since that process can take a few months. So what you have to do is make your best effort at figuring out 2-3 months ahead of time when that urgent need will pop up and start your recruiting efforts then.

Angel and Strategic Investors

While I and others have recently done a number of postings on Venture Capital investors and their relationship with entrepreneurs, I thought I’d do a posting on handling other kinds of investors — angels and strategics.

Angel investors. My definition: high net worth individuals who put personal money into a company. The good: they’re typically your friends and family, so they don’t play hardball when negotiating terms. The bad: they’re typically your friends and family, so every dinner party you attend has the potential to morph into an ad hoc investor relations conference. The ugly: you feel awful if you lose their money or dilute them down.

Strategic investors. My definition: operating companies (not investment firms) that invest in other operating companies. The good: they’re typically some kind of business partner, so if they have a stake in your company, they will be more likely to help you. The bad: the person at the comapny who made the investment decision is usually a different person than the person with whom you conduct business, so the incentives are rarely aligned the right way. The ugly: unlike financial investors, strategic investors can change their philosophy about making other corporate investments for any reason or no reason and leave you without support in future rounds and with an unproductive player around the table that makes a future exit difficult by their mere presence.

At the end of the day, not everone is cut out to invest in startups. My biggest takeaways about these two types of non-financial/VC investors are:

1. Be very selective about who you let invest in the early stages of your company

2. Make sure angel investors acknowledge to you verbally (above and beyond the accredited investor rep they give you) that they are totally comfortable losing all of their money

3. Make sure angels and strategics understand that in order to preserve the value of their investment, they may need to continue investing in your company if you end up raising multiple rounds of financing

4. Without being unfair, try to limit the rights (or assign them by proxy to you or to the Board or to a lead investor) of less sophisticated financial investors who aren’t and won’t be close enough to your business to participate in major corporate decisions down the road. Along these lines, you should strongly consider selling both types of investors common stock, especially if it’s early on in the company’s life

Why Email Will Win the Day

I attended the same presentation as Fred where a great B2C marketer talked about how she got a 40:1 payback for every dollar spent on email marketing versus an 8:1 payback on search. As head of an email marketing company, it was music to my ears.

But the “finite issue” Fred highlights is actually a great opportunity more than it is a drawback. Most marketers still have email addresses for less than 25% of their full customer database, meaning that if we do our job as an industry, we should be able to increase the availability of email addresses threefold in the coming couple of years. With the inevitable scale efficiencies in email marketing, that 40:1 number can become much bigger, maybe even as high as 100:1, over time.

The challenge for the industry is that this kind of transformation isn’t easy. A lot of the low-hanging fruit of early online adopters is gone. This means marketers are going to have to do more to embrace permission and drive organic list growth if they want to keep pushing the email ROI metric forward. Not necessarily brain bending stuff, but there aren’t a lot of shortcuts for it, either, and it requires a different mindset than traditional advertising and direct marketing. In the end, it all comes down to respecting the consumer and delivering the value exchange to customers.

Why is Seth Godin so Grumpy?

Permission marketing guru Seth Godin says we should all Beware the CEO blog. His logic? Blogs should have six characteristics: Candor, Urgency, Timeliness, Pithiness, Controversy, and maybe Utility — and apparently in his book, CEOs don’t possess those characteristics.

Certainly, CEOs who view blogs as a promotional tool are wasting their time, or are at least missing a fundamental understanding about the power of blogs and interactivity.

But many of the ones I read (and the one I write) do their best to be anything but promotional. One of my colleagues here describes my blog as “a peek inside the CEO’s head,” which is a great way of putting it. And I still stand by my earlier posting about the value of the blog to me and to the company — hardly “annual report fluff.”

How’s that for honest, timely, controversial, and pithy, Seth?

Book Short:  Required Reading

The Leadership Pipeline, by Ram Charan, Stephen Drotter, and James Noel, should be required reading for any manager at any level in any organization, although it’s most critical for CEOs, heads of HR, and first-time managers.  Just ask my Leaderhip Team at Return Path, all of whom just had to read the book and join in a discussion of it!

The book is easy to read, and it’s a great hands-on playbook for dealing with what the authors call the six leadersihp passages:

From Individual Contributor to Manager (shift from doing work to getting work done through others)

From Manager to Manager of Managers (shift to pure management, think beyond the function)

From Manager of Managers to Functional Manager (manage outside your own experience)

From Functional Manager to Business Manager (integrate functions, shift to profit and longer term views)

From Business Manager to Group Manager (holistic leadership, portfolio strategies, value success of others)

From Group Manager to Enterprise Manager (outward looking, handle external and multiple constituencies, balance strategic and visionary long-term thinking with the need to deliver short-term operating results)

All too often, especially in rapidly growing companies, we promote people and move them around without giving enough attention to the critical success factors involved in each new level of management.  I’ve certainly been guilty of that at Return Path over the years as well.  It’s just too easy to get trapped in the velocity of a startup someitmes to forget these steps and how different each one is.  This book lays out the steps very neatly.

It’s also one of the few business books that at least makes an attempt — and a good one at that — at adapting its model to small companies.  In this case, the authors note that the top three rungs of the pipeline are often combined in the role of CEO, and that Manager of Managers is often combined with Functional Managers.

Anyway, run, don’t walk, to buy this one!

Reverse Engineering Venture Economics

How to Negotiate a Term Sheet with a VC, Part II

The original posting (probably one of my top two or three in terms of comments and trackbacks) talked about HOW to negotiate a term sheet with a VC.  I just received a question from a reader today about WHEN to start looking for VC money.  The answer, of course, depends on your stage of business.

The general rule is that the best time to start looking for money is when you don’t need it — but not so early that a potential investor can watch your business closely for too long a period of time before the deal (since all startups have hiccups along the way). 

If you’re looking for seed capital, you may not have too many options in terms of timing, but best to do everything you can to keep bootstrapping things along with consulting or one-off projects.  Why?  At the proof-of-concept stage, the value of your company increases sharply with every new customer or new release, so best not to take capital too early as long as you can live without it.

If you’ve got a business going (say $1-3mm run rate), with a cash balance and a predictable burn rate, and you’ve never taken in institutional capital before, you should probably start talking to VCs 4-6 months before you run out of cash.  While you don’t want VCs to anchor a valuation in their mind too early, the reality is that it takes time to get these your first institutional deal done since it usually involves broader changes to corporate documents, and you definitely want to talk to several different firms, so a little more lead time is better.  This is especially true if your window of time interferes with August or the holiday season, when not much new business gets done at VCs unless you have a super hot deal.

If you’re looking for expansion capital and are near or at profitability, deals will probably take less time to get done, and valuations are likely to fluctuate less.  In these cases, I’d say less lead time is required, although if you’re in a volatile industry, you may need the capital sooner than you think!

But again, the best time to look for money is when you don’t need it.  Investors (even the nicest ones) aren’t afraid to "market price" a deal lower if they sense desperation or, more important, a lack of alternatives.  To that end, of every piece of advice in the original posting, the most important one, which affects timing, is #3 — get more than one VC interested in your deal!

Email Marketing 101

We just published a book!  Sign me Up! A marketer’s guide to creating email newsletters that build relationships and boost sales is now available on Amazon.com.  The book is authored by me and my Return Path colleagues Mike Mayor, Tami Forman, and Stephanie Miller.  What’s it about?

– At its core, the book is a very practical how-to guide.  Any company — large or small — can have a great email newsletter program.  They’re easy, they’re cheap, and when done well, they’re incredibly effective.

– This book helps you navigate the basics of how to get there, covering everything from building a great list, to content and design, to making sure the emails reach your customers’ inboxes and don’t get blocked or filtered.

– Our central philosophy about email marketing, which permeates the advice in the book, is covered in my earlier New Media Deal posting (which is reproduced in part in the book’s Preface) — that customers will sign up for your email marketing in droves if you provide them a proper value exchange for the ability to mail them.

– I’d encourage you to buy the book anyway, but in case you need an extra incentive, we are also donating 10% of book sales to Accelerated Cure, a research organization dedicated to finding a cure for Multiple Sclerosis, in honor of our friend and colleague Sophie Miller.

More postings to come about the process of writing, publishing, and marketing a book in 2005 — boy was the experience we had different than it would have been 10 years ago.

The Rumors of Email’s Demise Have Been Greatly Exaggerated, Part IV

This one could also be entitled “What Are The Bloggers Smoking?”

Reports from last week’s Blog Business Summit like this one are starting to filter in (pun slightly intended).  This one gets a big yawn from me, even more so than the other times I’ve posted on this subject, here, here, and here.  I’m as much of a blogger and a believer in blogs and RSS as the next guy — maybe even more so — but honestly, people, blogs are going to replace email?

I’d like to address a few critical points here head on, although a large part of me doesn’t even want to dignify yet another empty “email is dead” quote with a response.

Basic error #1. The article seems to confuse blogs with RSS feeds.  RSS feeds are data streams coming into an RSS reader application.  Blogs are web sites.  Hello?!?

Fallacy #1. Because blogs/RSS are interesting new media, email will go away.  To paraphrase my colleague Mike Mayor, why is it that whenever something new comes along, its proponents have to bash the current paradigm to make their thing seem more important?  Let’s go through this one — TV came along, and people said radio would go away.  Cable came along, and everyone said the networks were toast.  The fax machine came along, and FedEx was said to be relegated to legal documents that needed to be signed personally.  The Internet came along, and people said everything else was insignificant (newspapers, TV, radio, snail mail).  So yes, new media do arrive on the scene and perhaps make a dent in all prior media, but I’m having a hard time thinking of that one comes in and clocks another one mano a mano.

Fallacy #2. Spam has made email more difficult, therefore email will go away.  There’s a whole industry out there fighting spam.  I know, I know, just because we want the problem to go away doesn’t mean that we can will it away — but filters are working better by the day (did everyone catch this posting about Postini this week?), false positives can be managed down by vigilant clients working with vendors like Return Path, and whitelists, whenever they start really working and charging money to clients to guarantee delivery, will still leave email as the cheapest medium for targeted commercial messaging out there.

Naive belief #1. Spam has harmed email, but blogs/RSS are immune to the same problems.  I’m sorry, do you think the bad guys, or as Fred always calls it, the Internet Axis of Evil (spam, viruses, spyware, DNS hacking, phishing, and the like) are going to leave blogs and RSS feeds alone?  Not a chance.  The bad guys are already hard at work expanding their Axis of Evil.  There’s already comment spam for blogs (or blam, as some call it).  People have and can hijack RSS feeds (no cool name yet).  There’s Instant Messenger spam (spim).  Last week, I heard about a new one that blew me away, which is that someone figured out how to hijack a Voice Over IP phone call and insert an audio ad/porn into the call (spip).

Naive belief #2. Blogs are truly interactive.  Other than a couple of very popular blogs during the height of last fall’s election, I just don’t think this is true for the mainstream.  There are certainly some people who have a little too much time on their hands who spend hours every day blogging, but most people skim most blogs as one-way communication.   While there are mechanisms for commenting, there aren’t ready mechanisms for publishing comments back to the blog audience (thank goodness), so this medium hasn’t turned out nearly as interactive as people had hoped at the onset.  RSS feeds, in case the writer/speaker was confused in this argument, are completely non-interactive.

Naive belief #3. People will read blogs with an agenda of marketing specific products and services.  The beauty of the blog is that it’s not corporate, and it doesn’t have marketing spin on it.  Blogs are much more journals and publishing tools than marketing vehicles.  Who the heck is going to read a blog on Coke?  Or Nike?  Or Microsoft?  Sure, I might read Howard Shultz’s blog if he had one (his book was good enough), but that’s very different than reading the Starbucks official blog.  Why bother?  Where’s the value there?

Ok, I’m done with today’s rant.  As I said, I love blogging as much as the next guy, but puh-lease!  And for the record, I do believe that RSS feeds and maybe even IM from marketers/publishers will supplement email and in some cases maybe even replace it, but email just isn’t going away any time soon.

Oh, Behave!

This week, we launched behavioral targeting for email through our PostMasterDirect group.  This is a great development for us and will produce great value for clients over time by increasing response rates.  It may seem like a bit of buzzword bingo since BT is the phrase of the year in the online media world, but it’s actually a product we’ve had in development for some time now.

Our VP Engineering for list and data products, Whitney McNamara, had a great posting on his blog about BT and how we do it.  The whole thing is worth a read, but the real gem in my mind (and what’s most consistent with Return Path‘s philosophy about consumers and targeting in general) is at the end:

As a final note, it’s critical to remember that none of this means that the people who are collecting the data know better than that actual people on the receiving end what is appropriate and interesting. Ideally (as in the case of PMD/RP’s behavioral targeting), BT is a technique that supplements — not replaces — targeting based on people’s explicit requests for information.

And yes, I have to admit that at least a small part of the reason for this posting is the title.