As I transition back into my day job as the CEO of an Internet start-up, I can’t help but reflect on what I’ve learned from the Hillary-Obama Battle Royale. Both politics and business involve a lot of careful strategic planning by very talented people. But in both areas, few of these well-laid plans ever play out as they were originally intended.

For example, both Hillary and Facebook were media darlings a few months ago, before being deemed profoundly “unlikeable” or “untrustworthy” and entering into the fight of their lives. Both seem to have survived these scares, but it’s unclear what the public’s final decision will be in either case.

On a more general level, I think that there are 5 key truths that apply as much to politics as it does to business:

5. When the going gets tough, a lot of investors get going. As soon as it seemed that she might lose the New Hampshire primary after already having lost the Iowa Caucuses, a lot of Hillary’s investors started to get cold feet, forcing the Clintons to have a lot of reassuring chats with their investors. Even in politics, a lot of investors want sure bets. As CEO of a property search start-up, I’ve often been surprised when some VCs seem annoyed that there’s some risk involved with start-up ventures. My advice is that if you are lucky enough to get various offers from VCs or business angels, go with the one who will be around when you face an unexpected setback (like a loss in the Caucuses) or encounter an unexpectedly tough new market entrant that’s generating a lot of buzz. Go with someone who will stick with you through for better or for worse, within limits.

4. Karma is a bitch: Sometimes its easier to take ethical or legal shortcuts, but the truth will eventually come out. And it will take a big bite out of your ass when it does. There are lots of business examples here:

• Enron and their “creative” accounting theories;
• Martha Stewart, who thought she’d save a few dollars thanks to insider trading, but ended up paying a lot more in fines and jail time;
• Marion Jones, who disgraced herself and her fans when she admitted to using steroids. She too will see the inside of a jail cell; and
• Facebook, whose founder Mark Zuckerberg arguably lied and stole from former friends and colleagues to develop his mini-Empire. Some of the negative publicity about Facebook’s advertising platform (Beacon) arguably stems from the fact that Mark Zuckerberg seems a bit slimy.

Note that I didn’t say “Good guys finish last”, because I’m not quite sure I believe that. But the truth has a nasty and persistent habit of being discovered no matter how clever or careful you think you are. Just ask Bill Clinton and Monica Lewinsky.

3. Keep it simple, stupid! One of Obama’s great gifts is that he’s able to communicate controversial and complicated topics — race and poverty — via visual cues and oratorical flourishes. He doesn’t really ever delve into a 100-point plan. There’s no need to. His aim is to sell his vision of America. Great Internet companies like Google use a similar strategy. Both Obama and Google could obviously explain their core concepts in painful detail, but do you really care how Google generates so many relevant results in so little time? Or do you agree that Google’s minimalist home page conveys a simplicity that enhances its user experience. Great communicators — and great products - hide a lot of the complicated stuff , because they know that most consumers/voters suffer from Attention Deficit Disorder.

2. It’s great to be strong and visionary. But sometimes it’s okay to admit that you have weaknesses and doubts. It’s okay to be human. This is one that’s particularly easier said than done for me. A lot of people expect leaders to be emotionless robots. Winners execute exceptionally well no matter what the personal circumstance or obstacle. Displays of emotion are for the weak. But I think that the Hillary crying episode showed that the public resists leaders that appear inhuman and inflexible. In reviewing why people tend to be railing against Facebook all of a sudden, for example, Duncan Riley of TechCrunch explained that Mark Zuckerberg would “be better off relaxing a little more and being more open and honest; Facebook must reach a tipping point this year in growth and people will feel a lot better about supporting him if he was little less robotic, and more importantly more open.” Closed and robotic is out. Open and honest is in.

1. Charisma and “likability” matter, particularly when you want to be the top dog. Hillary is probably very annoyed that, although she has paid her dues, a much more charismatic male candidate is threatening her for the top spot. Although Obama is a lot less experienced than Hillary, voters are willing to focus more on his likability factor. All other things being equal, people like to see nice guys or women do well. In his Digg case study, for example, Nisan Gabbay argues that the Kevin Rose persona has a lot to do with Digg’s success. He explains: “I believe that Kevin Rose’s personality and public persona played a big part in Digg’s success. Initial users wanted to see Digg succeed because they wanted to see Kevin succeed. When Digg was raising its first VC round, some well-respected Internet investors felt that better products were about to be launched that would unseat Digg. However, we have learned that having a superior technical product is not necessarily the determining factor for success. Consumer Internet services are both an art and a science. The Kevin Rose persona was a big contributor to the “art” side of Digg that is impossible to replicate by competitors.”

To paraphrase Hillary’s evaluation of Obama, successful leadership is as much about poetry as it is about prose.