Ten Characteristics of Great Investors

Fred had a great post today called Ten Characteristics of Great Companies.  This link includes the comments, which numbered over 70 when I last looked.  Great discussion overall, especially for Fred’s having come up with the list on a 15-minute subway ride.  Fred used to write a series of posts about VC Chiches, and I would periodically write a Counter-Chiche post from the entrepreneur’s perspective.  This post inspired me to do the same.

So I’ve taken 15 minutes here, pretended I’m on the subway, and here is my list of Ten Characteristics of Great Investors, in no particular order:

1. Great investors know how to give strategic advice without being in the operating weeds of a company
2. Great investors get to know whole management teams, not just CEOs — in fact, great investors become part of the extended management team of their portfolio companies
3. Great investors invite you to do diligence on them by giving you a list of every CEO they’ve ever worked with and asking you to pick the ones you want to talk to
4. Great investors ask great questions
5. Great investors don’t publicly take credit for the success of their investments, even if they were major drivers of that success
6. Great investors show up for meetings on time and don’t spend the meeting using their smartphone
7. Great investors treat their portfolio companies’ money as if it were their own money when spending it on things like lawyers or travel
8. Great investors look for connections to make between their portfolio companies or relevant people but have a strong relevance filter and don’t send junk
9. Great investors never have a ready-made list of the ways they add value to companies — and they specifically never talk about the help they give in recruiting executives or making sales/bus dev introductions
10. Great investors recognize when they have a conflict around a portfolio company and are clear to represent their separate points of view separately

I’m not sure I’ll be invited to present this anywhere, but there it is for discussion.

From Founder/Builder to Manager/Leader

After I spoke at the Startup2Startup event last month, one of the people who sat with me at dinner emailed me and asked:

I was curious–how did you make the transition from CEO of a startup to manager of a medium-sized business? I’m great at just doing the work myself and interacting with clients, and it’s easy for me to delegate tasks, but it’s hard to have the vision and ability to develop my two employees into greater capacity…

I’d be interested in reading a blog post on what helped you make that transition from founder/builder to manager/leader

It feels like the answer to this question is about a mile long, but I thought I’d at least start with five suggestions.

1. Hire Up!  The place where I see most founders fumble the transition is in not hiring the best people for the critical roles in the organization.  Sometimes this is for cash flow reasons, but more often it is either due to subconscious fear (“will I still be able to control the organization if this person is in it?”) or due to bravado (“I can do engineering way better than that guy”).  Lose that attitude and hire up for key positions.  Even if you COULD do every role better than anyone you’d ever hire, you only have so many hours in the day.
2. Learn the magic of delegation and empowerment.  You can never get as much work done on your own as you can if you get work done THROUGH others.  Get comfortable delegating work by setting clear expectations up front in terms of timing and quality of deliverables and giving your high level input.  And never be a bottleneck.  If people are waiting on you for decisions or comments, that means they’re not working…or at least that they’re not working on the highest value or most urgent things they could be working on.
3. Don’t fear some elements of larger organizations.  Larger organizations require some process so they don’t fall apart.  Make sure you pick your battles and accept that some changes, even if they feel bureaucratic, are critical to ensure success going forward.  I still get a queasy feeling in my stomach half of the times I see a new form or procedure or a suggestion from a lawyer, but as long as they are lightweight and constantly reviewed to make sure they’re having their intended impact AND ONLY their intended impact, some are inevitable.
4. At the same time, don’t lose the founder/builder mentality.  Your company may have grown larger, but if you’re still running it, people will naturally look to you and other founders for much of the energy, vision, and drive in the business.  You will also likely be more inclined to be scrappy and entrepreneurial, which are good traits for any business.  Don’t lose those qualities, even as you modify them or add others.
5. Look to the outside for help.  In my case, I’ve consistently done three things over the years to learn from others and to prevent myopia.  First, I have worked on and off with a fantastic executive coach, Marc Maltz from Triad Group. Second, I have always had one or two “CEO mentors,” e.g., guys who have built larger businesses than Return Path, on my Board, at all times, as resources.  Finally, I do a lot of CEO peer networking, some informal (breakfasts, drinks meetings), and some more formal (a CEO Forum group that I established) to make sure I’m consistently sharing information and best practices with others in comparable situations.

Any other entrepreneurs who have made the leap have other advice to offer?

Yiddish for Business

Contrary to popular belief, Yiddish isn’t “Jewish slang” (I hear that a lot).  According to Wikipedia, Yiddish is a basically a High Germanic language with Hebrew influence of Ashkenazi Jewish origin, spoken throughout the world. It developed as a fusion of German dialects with Hebrew, Aramaic, Slavic languages and traces of Romance languages.  It is written in the Hebrew alphabet.

I don’t speak Yiddish.  Like many American Jews whose families came to America in the late 19^th and early 20^th centuries, my grandparents spoke it somewhat, or at least had a ton of phrases they wove into everyday speech.  Presumably their parents spoke it fluently before coming here and Americanizing their families.  My own parents have a handful of stock phrases down.  My brother and I have even less.

What I like best about Yiddish is that I find it to be a very descriptive and also onomatopoetic language.  I can never verbally describe a Yiddish word without a lengthy description and some examples, and usually some level of gesticulation.  I’ll try to be more succinct below.  But in the end, words mean a lot like what they sound like they should mean.  A lot of New Yorkers who aren’t Jewish end up knowing a handful of Yiddish words because they’re pretty prevalent in the City, but many people outside New York don’t.  So I thought I’d have a little fun here and do something different on the 6^th anniversary of launching this blog (today) and list out some of my favorite Yiddish words and describe them with a business context.  In no particular order…

–          Schmooze – to chat someone up, work them, frequently with some kind of hidden agenda in mind.  Business application:  “She showed up at the charity event just to schmooze Alice, who was a potential client.”

–          Chutzpah – nerve, as in “wow, he has some nerve.”  My dad always said the classic description of chutzpah was the kid who murdered both of his parents, then pleaded with the judge for leniency because he’s an orphan.  Business application:  “He missed all his goals this quarter and asked for his full bonus and a raise?  Now that takes real chutzpah!”

–          Spiel (pronounced schpeel) – a monologue or lengthy pitch.  Business application:  “I’m raising money, so I have to really organize my spiel before I go talk to the VCs.”

–          Schtick – someone’s standard song-and-dance.  Business application:  “I stood up in front of the room and gave my usual schtick about our values and mission.”  Kind of like Spiel.

–          Schlep – to make a long, pain-in-the-ass kind of trip.  Business application:  “I had to schlep all the way to Toledo for a meeting with that guy, and he didn’t even end up signing the deal.”

–          Mazel tov – literally means “good luck” but usually used in regular conversation to mean “congratulations.”  Business application:  “You got a promotion?  Mazel tov!”

–          Noodge – someone who inserts himself into a conversation in a somewhat unwelcome manner.  Related to Kibbitz – to give unsolicited advice from the sidelines. Business application:  “Sally is such a noodge.  She kibbitzes about my unit’s strategy all the time and just stirs up trouble.”

–          Maven – an expert, even a self-styled one, in a very niche area.  Business application:  “You want to figure out what smartphone to  buy?  Ask Fred – he’s the maven.”

–          Kosher (a Hebrew word as well) – completely by the books, originally referring to dietary laws that religious Jews follow.  Business application:  “Ask Marketing if it’s kosher to use our partner’s logo like that.”

–          Verklempt – choked up, overcome.  Business application:  “When I got my review and promotion and raise, I was so verklempt that I couldn’t speak for a minute or two.”

–          Schlock, Dreck, Chazerai, Bupkis – all have slightly different literal meanings (apparently Bupkis means “goat droppings”), but I use all of them somewhat interchangeably to mean junk or something of limited or no value.  Business application:  “That presentation was nothing but chazerai.  What did I get out of it?  Bupkis.”

–          Kvell – to beam or burst with pride, related to Nachus – warm “gooey” feeling of pride.  Business application:  “I had so much nachus when my company won that award for being the best place to work, I was just kvelling.”

–          Mishegas or Bubbamyseh – craziness or self-imposed silliness.  You might have heard the word Meshugenah before, which means crazy.  Business application:  “I can’t get all caught up in his mishegas.  I’m going to make my own decision here.”

–          Kvetch – either a noun or verb meaning complain, in a harpy kind of way.  Business application:  “Frank is such a kvetch.  He is just never happy.”

–          Mensch – a good guy.  Business application:  “Michael is such a mensch.  He always helps his colleagues out even when he doesn’t have to or doesn’t get credit for it.”

–          Fercockt (pronounced Fuh-cocktah) – crazy, messy.  Business application:  “John’s project plan is totally fercockt.  No one can follow it even when he tries to explain it.”

–          Mishpochah – family.  Business application:  “Welcome to the company – we’re happy to have you in the mishpochah.”

–          Tsuris – heartache or sadness.  Business application:  “Boy that’s one client that gives me nothing but tsuris.”

–          Tchotchke (pronounced chach-kee) – a trinket or little toy.  Business application:  “What kinds of tchotchkes are we giving away at our booth at the upcoming trade show?”

Pull one of these out in your next meeting – see what it gets you!

Macroeconomics for Startups

I’m not an economist.  I don’t play one on TV.  In fact, I only took one Econ class at Princeton (taught by Ben Bernanke, no less), and I barely passed it.  In any case, while I’m not an economist, I do read The Economist, religiously at that, and I’ve been reading so much about macroeconomic policies and news the past 18 months that I feel like I finally have a decent rudimentary grip on the subject.  But still, the subject doesn’t always translate as well to the average entrepreneur as microeconomics does – most business people have good intuitive understandings of supply, demand, and pricing.  But who knows what monetary policy is and why they should care?

So here’s my quick & dirty cut at Macroeconomics for Startups.  What do some of the buzzwords you read about in the news mean to you?

· Productivity Gains – This is something frequently cited as critical to developed economies like ours in the US.  Here’s my basic example over the past 10 years.  When I left my job at MovieFone in 1999, there were approximately eight administrative assistants in a company of 200 people – one for each senior person.  Today, Return Path has less than one administrative assistant in a company of the same size.  We all have access to more tools to self-manage productivity than we used to.  Cloud computing is another great example here of how companies are doing more with less. We have tons of software applications we use at Return Path, none of which require internal system administration, from Salesforce.com for CRM to Intacct for accounting. Ten years ago, each would have required dedicated hardware and operational maintenance.

· Fiscal Policy vs. Monetary Policy –  Fiscal Policy is manipulating the economy through government taxing and spending.  Monetary Policy is manipulating the economy by controlling interest rates and money supply.  For a small company that has revenue and accounts receivable, you probably are more inclined to Monetary Policy as it has more to do with your ability to access debt capital from banks through credit lines.  But if you’re in an industry where government grants or support is critical, Fiscal Policy can mean more to you in the short run.  Of course, if you’re losing money as many startups are, business tax credits and the like aren’t so relevant.

· Inflation – As my high school econ teacher defined it, “too many dollars chasing too few goods.”  Inflation may seem like a neutral thing for a business – your costs may be going up, but your revenue should be going up as well, right?  And we can inflate our way out of debt by simply devaluing our currency, right?  The main problem with inflation is that too much of it discourages investment and savings, which has negative long term consequences.  To you, rapid inflation would mean that the money you raise today is worth a lot less in a year or two.  That said, inflation is certainly better than Deflation, which can paralyze an economy.  Think about it like this – if you’re in a deflationary environment, why would you spend money today if you think prices will be lower tomorrow?

· Strong Dollar, Weak Dollar – Sounds like one of those things that’s politically explosive…of course we all want a strong dollar, right?  Why have a mental image of Uncle Sam that’s anything other than muscular?  And yes, it’s a lot more fun to travel to Europe when a latte costs you $4, not $8.  But the reality is that a strong dollar doesn’t necessarily serve all our interests well.  For a startup, sure, you can buy an offshore development team in India for less money than a development team in Silicon Valley, and for a more established company it makes it much cheaper to try and expand to Europe and Asia.  But an artificially strong dollar means that few people outside the US can afford to buy your product or service.  This is related to…

· Trade Surplus/Deficit and Exchange Rates – The net of a given country’s exports minus imports, and how much one currency is worth in terms of the other.  There’s been much talk lately about whether and how much China is manipulating its currency and holding it down, and if so, what impact that has on the global economy.  Why should you care?  If China is articifically keeping the value of the yuan down, it just means that the Chinese people can’t afford to buy as much stuff from other countries – and that other countries have an artificial incentive to buy things from China.  If the Chinese government allowed the yuan to appreciate more, the exchange rate vs. the dollar would rise, and your product or service would find itself with a lot more likely buyers in the sea of 1.3B people that is China.

I’m sure there are other terms of note and startup applications, but these are a handful that leap to mind.

Why Email Stamps Are a Bad Idea

(also posted on the Return Path blog)

Rich Gingras, CEO of Goodmail is an incredibly smart and stand-up professional.  I’ve always liked him personally and had a tremendous amount of respect for him.  However, the introduction of the email stamp model by Goodmail is a radical departure from the current email ecosystem, and while I’m all for change and believe the spam problem is still real, I don’t think stamps are the answer.  Rich has laid out some of his arguments here in the DMNews blog, so I’ll respond to those arguments as well as add some others in this posting.  I will also comment on the DMNews blog site itself, but this posting will be more comprehensive and will include everything that’s in the other posting.

It seems that Goodmail’s main argument in favor of stamps is that whitelists don’t work.  While he clearly does understand ISPs (he used to work at one), he doesn’t seem to understand the world of publishers and marketers.  His solution is fundamentally hostile to the way they do business.  I’m happy to have a constructive debate with him about the relative merits of different approaches to solving the false positive problem for mailers and then let the market be the ultimate judge, as it should be.

First, whitelists are in fact working.  I know — Return Path runs one called Bonded Sender.  We have documented several places that Bonded Senders have a 21% lift on their inbox delivery rates over non-Bonded Senders.  It’s hard to see how that translates into “bad for senders” as Rich asserts.  When the average inbox deliverability rate is in the 70s, and a whitelist — or, by the way, organic improvements to reputation — can move the needle up to the 90s, isn’t that good?

Second, why, as Goodmail asserts, should marketers pay ISPs for spam-fighting costs?  Consumers pay for the email boxes with dollars (at AOL) or with ads (at Google/Yahoo/Hotmail).  Good marketers have permission to mail their customers.  Why should they have to pay the freight to keep the bad guys away?  And for that matter, why is the cost “necessary?”  What about those who can’t afford it?  We’ve always allowed non-profits and educational institutions to use Bonded Sender at no cost.  But beyond that, one thing that’s really problematic for mailers about the Goodmail stamp model is that different for-profit mailers have radically different costs and values per email they send.

For example, maybe a retailer generates an average of $0.10 per email based on sales and proit.  So the economics of a $0.003 Goodmail stamp would work.  However, they’re only paying $0.001 to deliver that email, and now Goodmail is asserting that they “only” need to pay $0.003 for the stamp.  But what about publishers who only generate a token amount per individual email to someone who receives a daily newsletter based on serving a single ad banner?  What’s their value per email?  Probably closer to $0.005 at most.  Stamps sound like they’re going to cost $0.003.  It’s hard to see how that model will work for content delivery — and content delivery is one of the best and highest uses of permission-based email.

Next, Rich’s assertion that IP-based whitelists are bad for ISPs and consumers because IP-based solutions have inherent technology flaws that allow senders to behave badly doesn’t make sense.  A cryptographically based solution is certainly more sophisticated technology — I’ve never doubted that.

In terms of the practical application, though, I’m not sure there’s a huge difference.  Either type of system (IP or crypto) can be breached, either one is trackable, and either one can shut a mailer out of the system immediately — the only difference is that one form of breach would be trackable at the individual email level and the other would only be trackable in terms of the pipeline or IP.  I’m not sure either one is more likely to be breached than the other — a malicious or errant spammy email can either be digitally signed or not, and an IP address can’t be hijacked or spoofed much like a digital signature can’t be spoofed.

It’s a little bit like saying your house in the suburbs is more secure with a moat and barbed wire fence around it than with locks on the doors and an alarm system.  It’s an accurate statement, but who cares?

I’m not saying that Return Path will never consider cryptographic-based solutions.  We absolutely will consider them, and there are some things around Domain Keys (DKIM) that are particularly appealing as a broad-based standard.  But the notion that ONLY a cryptographic solution works is silly, and the development of a proprietary technology for authentication and crypotgraphy when the rest of the world is trying desparately to standardize around open source solutions like DKIM is an understandable business strategy, but disappointing to everyone else who is trying to cooperate on standards for the good of the industry.  I won’t even get into the costs and time and difficulty that mailers and ISPs alike will have to incur to implement the Goodmail stamp system, which are real.  Now mailers are being told they need to implement Sender ID or SPF as an IP-based authentication protocol — and DKIM as a crypto-based protocol — and also Goodmail as a different, competing crypto-based protocol.  Oy vey!

Email stamps also do feel like they put the world on a slippery slope towards paid spam — towards saying that money matters more than reputation.  I’m very pleased to hear Goodmail clarify in the last couple of days that they are now considering implementing reputation standards around who qualifies for certified mail as well, since that wasn’t their original model.  That bodes well for their program and certainly removes the appearance of being a paid spam model.  However, I have heard some of the proposed standards that Goodmail is planning on using in industry groups, and the standards seem to be much looser than AOL’s current standards, which, if true, is incredibly disappointing to say the least.

Jupiter analyst David Daniels also makes a good point, which is that stamps do cost money, and money on the line will force mailers to be more cautious about “overmailing” their consumers.  But that brings me to my final point about organic deliverability.  The mailers who have the best reputations get delivered through most filtering systems.  Reputations are based largely on consumer complaints and unknown user rates.  So the mailers who do the best job of keeping their lists clean (not overmailing) and only sending out relevant, requested mail (not overmailing) are the ones that will naturally rise to the top in the world of organic deliverability.  The stamp model can claim one more forcing function here, but it’s only an incremental step beyond the forcing function of “fear of being filtered” and not worth the difficulty of adopting it, or the costs, or the risks associated with it.

Rich, I hope to continue to dialog with you, and as noted in my prior posting, I think separating the issues here is healthy.

It’s Easy to Feel Like a Luddite These Days, Part II

In Part I, I talked about tagging and podcasting and how I felt pretty lame for someone who considers himself to be somewhat of an early adopter for not understanding them.  So now, 10 weeks later, I understand tagging and have a del.icio.us account, although I don’t use it all that often (quite frankly, I don’t have tons of surfing time to discover cool new content).  And I’ve even figured out how to integrate del.icio.us with Feedburner and with Typepad.

I’m still out of luck with Podcasting, mainly because my iPod and computer setup at home makes it really difficult to add/sync, so I haven’t given that a shot yet.

But today I had another two breakthroughs — I switched from AOL Instant Messenger to Trillian for my IM client, and I started using Skype.  Trillian is pretty cool and of course free.  I’ve never used MSN Messenger or Yahoo Messenger seriously, so the value for me is less in the aggregation of all three clients, and more in tabbed chatting.  Just like Firefox, the client lets you have all your chat windows displayed as tabs in a single window, which is much simpler and cleaner.  But better than Firefox, you can detach a chat window if you want to see it separately.

Skype is really cool.  I understand why the company will be sold for a good price, although I still don’t understand either $3 billion as a price or eBay as a buyer.  For those of you who don’t know what it is, Skype is voice Instant Messenger on steroids.  The basic functionality (for free) is that you can ping someone computer to computer, and have a real time voice chat if you are both online and accept the connection via your computer’s microphone.  If you decline the connection, it saves a voicemail for you.  The extras, which I haven’t tried yet, include SkypeOut (you can dial a real phone number from your computer for $0.02/minute, anywhere in the world) and SkypeIn (you get a phone number to give people so they can call your computer from a phone).  The quality was pretty good — certainly as good as or better than many cell phone connections, if not up to land line or VOIP standards.  Permission and usage/volume controls will be an issue here long-term since this is much more intrusive than regular test-based IM, but when it works, it is a beautiful thing.

Now, just like the vendor mayhem in the blog/RSS world (Typepad, Feedburner, Feedblitz, etc.), we need to get Trillian to incorporate Skype into its client so there’s a truly universal chat application.

Beyond Policy

Policies are an important part of managing employees. Similarly, contracts are an important part of running the commercial side of the business.  But it’s impossible to legislate every potential down-the-road situation ahead of time. That’s why one of the 13 core values at Return Path is

We believe in doing the right thing

I’ll admit that more than most of our values, this one sounds like Motherhood and Apple pie. Who doesn’t want to do the right thing?  The reason this value is an important part of our culture is that when we are in a tough situation, we stop and ask ourselves the most basic, yet thought provoking question — what’s the right thing to do here?

• When you fire an employee immediately before a major block of stock options vest, what’s the right thing to do?  Vest the options
• When you have a client who for some reason can no longer use your product or service or legitimately can’t pay their bill, what’s the right thing to do?  Let them out of their agreement, or at least let them suspend their agreement, even if it’s a long term contract
• When you make a payroll mistake and the employee doesn’t notice it but you discover it after the fact, what’s the right thing to do?  Let the employee know…and make them whole (the reverse is true of course as well, in cases where employees are the beneficiaries of an unnoticed payroll error – the right thing is to let the company know and make the company whole)
• When you have a choice of a car service (price equal) that runs only hybrid cars or more luxurious gas guzzlers for your routine trips to the airport, what’s the right thing to do?  Go green, baby!
• When you make a mistake and a client is adversely impacted but doesn’t notice it, what’s the right thing to do?  Fess up, quickly and thoroughly

I’m sure we don’t always get the tough calls right. That’s part of being a community of humans with emotions and faults. But we know that our reputation as a business goes well beyond following our policies and contracts and try to do the right thing as circumstances dictate.

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

Should You Have a Board?

As I mentioned last week, Fred’s post from a few months ago about an M&A Case study involving WhatCounts had a couple of provocative thoughts in it from CEO David Geller.  The second one I wanted to address is whether or not you should have take on institutional investors and have a Board.  As David said in the post:

Fewer outsiders dictating (or strongly suggesting) direction means that you will be able to pursue your goals more closely and with less friction

Although I have a lot of respect for David, I disagree with the notion that outsiders around the Board table is inherently bad for a business, or at least that the friction from insights or suggestions provided by those outsiders is problematic.

While that certainly CAN be the case, it can also be the case that outside views and suggestions and healthy debate, as long as incentives are aligned, people are smart, and founders manage the discussion well, can be enormously productive for a business.  I recognize that I’ve been very lucky that the Board members we’ve had at Return Path over the years have not been dogmatic or combative or dumb, but I do think selection and management of Board members is something very much in a CEO’s control.

But beyond the issue of who sets the agenda, Boards create an atmosphere of accountability for an organization, which drives performance (and many other positive qualities) from the top down in a business.  Budgeting and planning, reporting on performance, organizing and articulating thoughts and strategy – all these things are crisper when there’s someone to whom a CEO is answering.

As a telling case in points, I’ve known two CEOs over the years in the direct marketing field who have more or less owned their companies but insisted on having Boards.  While I’m not sure if those Boards had the ultimate power to remove the owner as CEO (which is the case in a venture-dominated Board and of course an important distinction), I do know that having a Board served them and their organizations quite well.  The fact that they didn’t have to have “real Boards” but chose to anyway – and ran spectacular businesses – is a good controlled case study for me in the value of this discipline.

Size of Pie, a.k.a. What Type of Entrepreneur Are You?

Mmmm…pie.  A post that Fred had up a few weeks ago about an M&A Case study involving WhatCounts, a company in the email space that I’ve known and had a lot of respect for for years, got me thinking about two different topics.  The first is thinking about types of entrepreneurs.  I’ve always said there were two types:  serial entrepreneurs who are great at starting companies but less great at scaling them, and entrepreneurs who are often part of a group of founders but who go on to continue to run the business for the long-haul.

CEO David Geller’s quote that gets to the heart of this in Fred’s post was:

…a bigger piece of a smaller pie, at some point, is the same as a smaller piece of a much larger pie.  And, donʼt let anyone tell you that baking a bigger pie isnʼt a whole lot more difficult.

Although David is talking about taking in outside capital and founder dilution in pursuit of larger business growth and objectives, he is also getting to the same point about entrepreneur type.  Scaling an organization beyond proof of concept, happy few customers, and profitable to be a $50-100mm business (and beyond) requires a whole different skill set than starting something from scratch and turning an idea into reality.

And in a sense, David is right.  Baking a larger pie can be a whole lot more difficult for some entrepreneurs if they are more of the serial entrepreneur type, or at least it can be far less interesting and fulfilling if what gets you out of bed in the morning is creating new things.  But for other entrepreneurs who are more of the “run the business” variety, getting out of the creation phase and into the scaling phase is more interesting and maybe even less difficult.  Even though businesses are never de-risked and a larger business with more employees just means there are more chips on the proverbial table, baking a larger pie and tending to the things that come with it – people issues, innovating within a platform, solving customer problems – can be less daunting than creation for some entrepreneurs.  (Return Path is in its twelfth year – can you guess which kind I am?)

So David’s right in terms of his core point about founder equity value and how large a slice of how large a pie the founder ends up with.  But whether baking a larger pie is easier or harder is less about an inherent difficulty in pie-making and more about the type of entrepreneur involved.

I’ll cover my second reaction to Fred/David’s post next week.

You Have to Throw a Stone to Get the Pond to Ripple

This is a post about productive disruption.  The title comes from one of my favorite lines from a song by Squeeze, Slap & Tickle.  But the concept is an important one for leaders at all levels, especially as businesses mature.

Founders and CEOs of early stage companies don’t disrupt the flow of the business.  Most of the time, they ARE the flow of the business.  They dominate the way everything works by definition — product development, major prospect calls, client dialog, strategy, and changes in strategy.  But as businesses get out of the startup phase and into the “growth” phase (I’m still trying to figure out what to call the phase Return Path is in right now), the founders and CEO should become less dominant.  The best way to scale a business is by not being Command Central any longer – to build an organization capable of running without you in many cases.

Organizations that get larger seek stability, and to some extent, they thrive on it.  The kinds of people you hire into a larger company aren’t accustomed to or prepared for the radical swings you get in startups.  And the business itself has needs specifically around a lack of change.  Core systems have to work flawlessly.  Changes to those systems have to go off without a hitch.  Clients need to be served and prospects need to be sold on existing products.  The world needs to understand your company’s positioning and value proposition clearly — and that can’t be the case if it’s changing all of the time.  Of course innovation is required, both within the core and outside of it, but the tensions there can be balanced out with the strengths of having a stable and profitable core (see my colleague George Bilbrey’s guest post on OnlyOnce a couple months back for more discussion on this point).

Despite all of this required stability, I think the art of being a leader in a growth organization is knowing when and how to throw that stone and get the pond to ripple — that is, when to be not just disruptive, but productively disruptive.

If done the right way, disruption from the top can be incredibly helpful and energizing to a company.  If done the wrong way, it can be distracting and demotivating.  I’ve been in environments where the latter is true, and it’s not fun.  I think the trick is to figure out how to blaze a new trail without torching what’s in place, which means forcing yourself to exercise a lot of judgment about who you disrupt, and when, and how (specifically, how you communicate what it is you’re doing and saying — see this recent post entitled “Try It On For Size” for a series of related thoughts).

Here are a few ideas for things that I’d consider productive disruption.  We’ve done some or shades of some of them at Return Path over the years.

• Challenge everyone in the organization or everyone on your team to make a “stop doing” list, which forces people to critically evaluate all their ordinary processes and tasks and meetings and understand which ones are outdated, and therefore a waste of time
• With the knowledge and buy-in of the group head, kick off an offsite meeting for a team other than the executive team by presenting them with your vision for the company three years down the road and ask them to come back to you in a week with four ideas of how they can help achieve that vision over time
• If you see something going on in the organization that rubs you the wrong way, stop it and challenge it.  Do it politely (e.g., pull key people aside if need be), but ask why it’s going on, how it relates to the company’s mission or values as the case may be.  It’s ok to put people on the defensive periodically, as long as you’re asking them questions more than advocating your own position

I’m not saying we have it all figured out.  I have no doubt that my disruption is a major annoyance sometimes to people in the organization, and especially to people to report to me.  And I’ll try to perfect the art of being productive in my disruption.  But I won’t stop doing it — I believe it’s one of the engines of forward progress in the organization.