Are Great Businesspeople Also “Clever”?


When I was younger, I thought being a mega-successful entrepreneur like Richard Branson or Michael Dell was a matter of cleverness. If you were just clever enough to figure out the right market opportunity, then you could make millions.

How wrong I was.

Take Richard Branson. For his very first entrepreneurial undertaking — when he was still just a teenager — he purchased young Chrismas Trees, planted them during the spring, and then resold them at a profit during Christmas time in the winter. I actually do think that’s pretty clever, especially for a kid. But really that’s as far as “clever” alone will take you.


Are You Ambitious or Grandiose?


One of the things I really love about my life is I’ve met more entrepreneurs than I can count. One of the coolest things about entrepreneurs is that they seem to have zero demographics in common. In other words, I’ve met entrepreneurs…

  • From both wealthy homes and poor homes
  • Of pretty much all ethnic backgrounds
  • From pretty much all educational backgrounds
  • Of pretty much all ages
  • In equal proportion from both sexes
  • Of course, as with any group, there are things in common. I guess “traits of an entrepreneur” is destined for another posting.

This post is about a very important difference I’ve seen in all entrepreneurs, and here’s what it comes down to:


Why Do Entrepreneurs Become Entrepreneurs?


I recently stumbled upon It’s basically a documentary, split up into several episodes, that covers the birth of the website by following around the CEO/Founder, Ted, and the PR person, Britt.

PayPerPost (”PPP”) is a weird concept — PPP pays bloggers to write content and sources content from Publishers, and then earns money by charging advertisers to put ads on PPP-sponsored blog sites. It’s been controversial because blogging’s rise to fame is due to its unbiased nature, and paying someone to blog, well, I guess it’s hard for them not to be biased.

But the success of PPP is another discussion. I’m more interested in the man behind PPP, Ted. Based on 10 minutes of watching RockStartup, I defnitely saw some “patterns” I’ve seen in other entrepreneurs.

When I was at Wharton as an undergrad, in my Senior year I took an Entrepreneurship course where you had to build some unique software, come up with a business plan, and then pitch it all to VC’s.

Our idea was terrible. We were going to build a system for people running political campaigns to help them get a sense of how people were planning on voting. We had a barcode-scanner-pen that scanned in a person’s survey responses, and then aggregated all the information so that a campaign director could see how people felt about a variety of issues.


Sometimes, Actually Pursuing a Goal is the Worst Way to Achieve It

general zen

There’s a strange phenomenon I’ve discovered in business and in life: I call them “Counter-Goals”.

So what’s a Counter-Goal? Well, it’s a goal which is achieved best by not pursuing it in the first place. Huh?

Okay, an example. When I was in my first year at Wharton Undergrad, I took a class called Management 100. The concept of the course was (and probably still is) quite novel. I was a member of a group of 12 other freshmen, and as a group we were tasked with completing some kind of major project. One group had to build a playground. Another group had to hold a major fundraising event. Our goal happened to be teaching the basics of economics to sixth graders.


Strange Lessons in Learning How to Sell Well


I’ve never really thought of myself as a salesperson.

I remember when I was younger I interned for GE and they had some career fair at the end of the summer where you met people in all the different “early talent identification” programs. When I got to the sales people, they all just seemed so smooth. I didn’t trust them, and I certainly didn’t want to buy anything from them. I just couldn’t picture myself joining that table over some of the others.

Well, fast forward a few years after I started Omedix and reality struck – I had inadvertently positioned myself as the sole salesperson for our company. Either I sold our product or we didn’t do business; it was that simple. And so I had to start learning how to sell.


When It’s Inconvient for the Company

Recently, I’ve been working on the parental leave policy for Gruntwork. It’s brought up a bunch of interesting questions like how much time should new parents get once a new child arrives? What will primary caregivers receive vs. secondary caregivers? Do we pay their full salary, or a portion of it?

Gruntwork is a distributed team, with about half of us in the USA and the other half in Europe or Africa, so it’s also been an education in how all the different countries of the world handle parental leave. Did you know that in Germany you can legally take up to 3 years of fully paid parental leave for each child, with your full salary paid by the government? That’s quite a contrast with the USA’s “we only guarantee you’ll have a job when you come back” approach!

In an ideal world, our policy would actually offer something like 3 years fully paid leave, but the reality is that, as a team of 12 people, losing 1 person for 3 years and paying them their full salary just isn’t tenable for us. So we have to constrain. And that’s when you start to enter a world where you make trade offs between how “convenient” a policy is for the business and how well that policy reflects your values.

The truth is that any parental leave is “inconvenient” to the company. In our case, losing one person for 12 weeks means ~10% of our entire team is out for an entire quarter. Their salary will continue to be paid, and it’s just a short enough amount of time that it probably doesn’t make sense to hire someone in their place.

And then there’s the reality of cash positions. We only have so much cash in the bank. If too many people are out on parental leave at the same time and we’re spending their salaries but not able to generate revenue from the typical work they do, then an overly generous parental leave policy has the potential to serve the new parents among us at the expense of the other families who work in the company.

It became clear to me that the most “convenient” thing for a business is to discourage people from having kids altogether by offering a minimal parental leave policy. An approach like that is clearly offensive.

…community kitchen containers