Rude VC: Outsmarting the system vs. Cheating


Two distinct incidents in the sporting world stood out last month that caught my attention in their contrast on a similar theme.

Undoubtedly the most prominent was the United States Anti Doping Agency’s (USADA) stripping of Lance Armstrong’s seven Tour de France championship titles. Quick recap: USADA alleged that Lance had used banned substances during certain periods of his professional cycling career. Even amid nagging questions about its juridiction and motives, the anti-doping agency had apparently assembled ten former teammates as witnesses and was preparing to submit Lance’s indictment to binding arbitration. Despite Lance’s proclamations of his innocence, on August 23 he decided to no longer fight the charges stating that, “Enough is enough.

Another seemingly less discussed incident that also took place in August was the UK’s performance in the men’s triathlon event at the Olympic Games. To sum up the Brits’ performance in one word: dominant. The UK’s Jonathan Brownlee earned the bronze medal, and his older brother Alistair won the gold, clocking in a breathtaking record time of 1:46.

Only the Spaniard Javier Gomez proved anywhere close to keeping pace with the Brownlee brothers, taking the silver medal (which the younger Brownlee would have won were it not for a penalty delay).

The Brownlee brothers have proven their mettle as phenomenal triathletes on the short distances (they’ve raced a number of triathlons in France too). They ranked among the favorites to finish on the Olympics podium, and they didn’t disappoint.

However, the UK triathlon team employed a tactic that definitely gave them a marked advantage over the other athletes. Specifically, the two Brownlees’ lighting-fast 10k run splits of 29 minutes stemmed in part from the energy they conserved during the bike segment just prior. This is where the teamwork element came in. Stuart Hayes, the third member of the UK triathlon team, played the role of ‘domestique’. In order words, Hayes, who finished in 37th place overall, served to drag along the Brownlee brothers during the bike segment (a rider drafting behind a lead rider can economize as much as 30% energy).

The UK triathlon team drew inspiration from the Tour de France, and in applying this tactic to the Olympics, they caught the other riders off guard. Unlike gaining an edge from banned substances, the British triathletes’ drafting technique was perfectly legal and legitimate. But in both this case and Lance’s alleged doping, one could argue that the atheletes gained an unfair advantage by not competing on a level playing field.

Successful entrepreneurs do this all the time

In many ways, the UK triathlon team’s actions resemble what disruptive entrepreneurial ventures do. They essentially changed the rules of the game (my guess is this practice will become more prevalent in the 2016 Rio games). Entrepreneurs by nature tend to defy rules and conventional wisdom. Moreover, as VCs, we actively seek out companies that have an unlevel playing field tilted in their favor. So when does the rule-breaking go too far ?

I’m convinced that an ability to act first and seek forgiveness later, rather than requesting advance permission, is an astute practice of successful entrepreneurs. But of course this reasoning can be carried too far. Would YouTube have emerged as the worldwide leader in online video without its early abundance of unauthorized music videos ? Would Badoo have scaled so quickly without its allegedly fictional profiles of hot women ?

At what point does an entrepreneur cross the line from resourceful to immoral…

  • Inflating revenue projections ?
  • Exaggerating product benefits in a sales call ?
  • Padding a technology application for an innovation subsidy ?
  • Posing as a prospective customer to gain competitive intelligence ?

It’s an age-old question: when, if ever, does the end justify the means ?