Business Thoughts

Web Entrepreneur 2.0 10 Characteristics of New Internet CEO's

Haven’t worked out in 2 weeks. Finally, at a conference in Vegas, I got a second to hit the Gym (only at hotels in Sin City would you have to PAY additional to do something healthy). On my way back from the Gym, I bumped into Kris Jones of PepperJam who was recently voted an Inc 500 fastest growing company. I was on a panel with Kris a year or so ago and was very happy to see him in the lobby and congratulate him on this achievement. He briefly introduced me to shoemoney, who I never met but I read his blog all the time!

That got me thinking about something… new entrepreneurs are different. We actually congratulate our competitors from time to time (Kris – I hope to make it on the list too, buddy). Today, there is all this talk of web 2.0 (since when has making things valuable and easy to use been a REVOLUTION? But that is a different post).

Lets talk about the new entrepreneur and what they often look like. Now of course before this there are a slew of characteristics like focus on profitability, cash flows, etc.

But I want to focus on the other things. And may I say that the inspiration from this post comes from 2 events:

1) Meeting Rand Fishkin, the founder of SEOmoz, who I aspire to have SEER emulate in SO many ways, but he takes some of his openness to an extreme I just can’t do yet but wholly respect!! His posts on hiring people, revenues, etc. are just amazing and well VERY open. Not to mention his answer to someone on Online Reputation Management showed his true ethics to everyone at a panel he was on at Pubcon. I wish there was a video of that snippet.

2) Craig Newmark of Craigslist (Missed the Stern event) who is totally fine with not making Craigslist more profitable by adding things to the site that could earn even more revenue. Wall Street’s collective jaw dropped when their CEO told them “Nah, maximizing revenues isn’t part of our equation!” That’s a tough pill to swallow.

What are the top 10 characteristics of “New” Web Enterepreneurs?
So I thought I’d start the list. Please add yours as well. Let’s see where it goes, ok?

1. Love what they do – The use of the word “Fun” is heavy in their rotation

I have found that time and time again the new Internet CEO talks about what they do as “Fun” as much as they talk about profitability, competitors, etc. The feeling that they wake up and say “Yeah, I got 3 hours of sleep last night, but man was it better than that last job!” is part of it.

2. Honesty – The new Internet entrepreneur is brutally honest

They aren’t scared to be honest with themselves, their employees, and their clients. Faking the size of your team (bringing in consultants to fill the office on the day of a big presentation) is LAME! Saying, “We’re good at what we do and whether we have 3 people or 30 lets focus on results” is more typical.

3. Less Fluff – Using words like “global leader”or “best of breed” is for chumps

These guys and gals are much more likely to be overly modest (sometimes to their own detriment). They often let the results speak for themselves. Saying “best of breed” and proving “best of breed” are two totally different things. If they have marketers or PR firms, they fire the ones who want to use overly sales speak.

They don’t use words like “proprietary” or “world-class” to talk about themselves & their companies; they talk about the value they add to organizations / people. You’ll see them use words like:

  • Adds value
  • Helps people do (insert here)
  • Makes things easier for (insert here)
  • Return on investment

4. People – They actually care about them!

The new Internet CEO (who, by the way, is less likely to call themselves CEO / President) understands people. People aren’t looked at as widgets or “human capital” but are looked at as beings. Beings who work for a reason – they work to buy first row Duke tickets, to have time to buy a new bike and ride that bike to Chicago, to surf their life away (not on the web but in the ocean), to be great parents, to be there for recitals and coach sports events.

They do not work to make you rich.

Employee 2.0 knows what they are worth. The new CEO doesn’t forget that. They probably started their companies because their old bosses forgot that employees worked to achieve their own dreams. The new CEO gets that people work so hard for their own reasons and builds flexibility in the business to allow this to happen.

5. Get big fast – NOPE – Stay profitable & add value

The new Internet entrepreneur could care less about getting big quick! They are passionate about what they do (see #1). So if getting big and taking major capital expenditures results in them going back to work for someone else before THEY chose to, they would be pissed. They focus on profitability! The thought process is, “If I can stay profitable, I can do this for as long as I want to, on MY OWN TERMS.” That is a good thing. If getting big is part of MY plan, then sure, I may want that too.

6. Frugality – No Herman Miller Chairs!

Those new CEO’s who lived through the first bubble and work at large companies remember seeing the big boardrooms being built, brand new Herman Miller Chairs being rolled in, and Bose speakers being installed in that boardroom – all while their companies went down the tubes. The new CEO knows that the right client doesn’t make purchasing decisions on the types of chairs they sit in. Actually having the Herman Miller Chairs could have the opposite effect, making your prospect say, “Wow, maybe my bill would have been 10% less, but I guess I have to help pay for their overhead.”

Lets consider the effect this has on employees. Nothing like buying 20 chairs for $20,000 and doling out 4% raises in the same year to keep morale high and turnover low. That kind of thinking always makes people feel valued, doesn’t it?

People marketing to the new CEO, remember this: they are frugal. They got to where they are because their office furniture was bought off of Craigslist and at IKEA LOOOOONG before it was Steelcase or Knoll. They bought refurbished monitors, servers, and laptops long before they did a big lease of 50 new machines.

If Herman Miller chairs MUST be bought, used is the way to go, right?

7. Thought leadership, if it happens, is “somewhat” accidental

New entrepreneurs don’t start blogs because they are “supposed to” or because they want to be thought leaders. They start them because they have something they want to share with the industry, with the community, clients, etc. Now, are they pushing a bit? They should, but they also gain popularity because their blogs time and time again provide VALUE.

Very often these new CEO’s open up code to be edited by others in contests. They build tools to share with the industry. Take Aaron walls’ keyword tool (my favorite). He offers it on his site, but then offered up the source code for others to put on their sites. (I bet old thinking CEOs will copy the code put it on their sites and act like they developed it, chumps!).

If they have blogs, I also think that they have no problem linking to others who are in their space! Clients don’t expect you to know it all in this information drenched world. So stop faking it! New CEOs can be honest on their blogs and give shout outs to people who they could compete with someday. But they don’t look at it that way. They link to sources of information for people reading their blog (AHEM…ADD VALUE to their readers, see #3).

They never refer to themselves as thought leaders, experts or GURUS. That’s for tools.

8. True to themselves – No apologies for being them (outside the boardroom)

They realize that client meetings require a certain dress, but if you bump into these guys and gals on a regular day, be prepared. The suit is gone, the suit jacket is gone, and all are replaced with cut offs, shirts with stupid sayings, or whatever they are comfortable in. And they like it that way. They “keep it real.” They keep it so real that the new CEO says if someone chooses NOT to work with me because they saw me dressed like a bum or saw a picture of me on flickr with one too many drinks at the last conference, well maybe they aren’t the right type of person for ME to work with. See the picture of one of the Google founders dressed like a woman (complete with wig & dress) by searching for Sergey Brin.

9. Do what is right

This is a mantra, not that is posted on some silly mission statement on the way in – that is SOOOOOOO 1995. Instead, they do what is right and the folks they work with in turn know that. No one needs to post it to a welcome page on an extranet or on the way into the office. Their mission statement is a part of who they are, and as a result it doesn’t need to be visible for everyone to see. Everyone who interacts with them knows what they are all about.

How do you think open source took off and has threatened companies as big as Microsoft? People believe in the power of sharing and online communities and giving back to communities they have taken things from.

10. Focus – think Google (now I get SEO on you for a second)

Google didn’t INVENT the search engine, you realize that right? The new CEO makes things better. While the Excite, Yahoo!, MSN, Altavista, Lycos, Webcrawler, and Northern Light’s of the world were there first, none of them focused on making the lives of people BETTER with information retrieval as well as Google. Instead, they focused on horoscopes, fantasy football, entertainment sections, weather, etc. FIRST. Instead, Google stuck to search (this was and still is evident by the fact that their homepage is just a box – no sports scores, no local movie listings, no “kids” sections). While Google is branching out a bit, I think if they stick to their core and build new services off of that core they’ll be in good shape. Only time will tell.

So there is the list. Please add to it. My first comment will list what I’ve done to try to do these things… it is HARD, but would you be willing to list out what you’ve done this year to embrace the above? I need a little inspiration.