An Entrepreneur’s Mistake

Question: What mistakes have you made as an entrepreneur?

James Sherman:  There are many mistakes, and I think every entrepreneur would say that they've had a lot of mistakes to manage through.  And hopefully you dodge the big mistakes, and the big ones don't sink the ship, and hopefully it's just a bunch of small ones that you're able to learn from.  And there's no doubt in my mind that you learn more from your mistakes than from all the things that you do right.  In terms of mistakes in our case, I would say -- I think I alluded to this earlier -- I think raising a larger round would have made sense at the time.  We did a round of financing in 2007, Series B, and we did have the opportunity to bump that round up.  And I wish we had done it for a couple million dollars more.  So -- but you know, I don't think anyone was anticipating some of the other hurdles we would face coming up.  But -- so that, I think, is one mistake that I would have done things a little bit differently.

Another is, certainly in the case of our magazine we are an online business; 90 percent of our business is online.  We did something very unusual in launching a print product, both because we believe it will be profitable -- it has a great opportunity to be a solid, profitable business -- but it also reinforces our overall brand and the positioning of our brand.  However, if I were to do things differently, I would not have launched in the middle of 2006.  I would have had us do a prototype for it rather than actual printing of the magazine.  We ended up burning through some cash with actual manufacturing and production of that magazine, and I think we should have done a prototype first and then launched a little bit later.  Which brings me to a general lesson, which is:  think very hard about where you're investing your money, and if you can figure out ways to take smaller steps that are lest costly to prove a concept, do it.  Definitely, you know, consider -- even if you have a large amount of money on hand, treat it as if you didn't have a large amount of money on hand, and see about ways in which to minimize your risk exposure and the use of cash, because if you're going to make a bad -- if you're going to take a bad turn, then it's better to lose a little bit of money on that rather than a lot.

Recorded on October 30, 2009

CEO of Sherman’s Travel Media, Jim Sherman reflects on one major shortcoming when launching his company.

​There are two kinds of failure – but only one is honorable

Malcolm Gladwell teaches "Get over yourself and get to work" for Big Think Edge.

Big Think Edge
  • Learn to recognize failure and know the big difference between panicking and choking.
  • At Big Think Edge, Malcolm Gladwell teaches how to check your inner critic and get clear on what failure is.
  • Subscribe to Big Think Edge before we launch on March 30 to get 20% off monthly and annual memberships.
Keep reading Show less

The culprit of increased depression among teens? Smartphones, new research suggests.

A new study, led by psychologist Jean Twenge, points to the screen as the problem.

A teenager eyes her smartphone as people enjoy a warm day on the day of silence, one day prior to the presidential elections, when candidates and political parties are not allowed to voice their political meaning on April 14, 2018 in Kotor, Montenegro. Citizens from Montenegro, the youngest NATO member, will vote for a new president on Sunday 15 2018. (Photo by Pierre Crom/Getty Images)
Surprising Science
  • In a new study, adolescents and young adults are experiencing increased rates of depression and suicide attempts.
  • The data cover the years 2005–2017, tracking perfectly with the introduction of the iPhone and widespread dissemination of smartphones.
  • Interestingly, the highest increase in depressive incidents was among individuals in the top income bracket.
Keep reading Show less
Photo by Alina Grubnyak on Unsplash
Mind & Brain

Do human beings have a magnetic sense? Biologists know other animals do. They think it helps creatures including bees, turtles and birds navigate through the world.

Keep reading Show less