Risk and Reward: A Q&A With Marketing Industry Leader & Author Kip Knight

Kip Knight’s four-decade career has taken him to over 60 countries, where he’s held a variety of marketing and general management roles at prominent corporations including P&G, PepsiCo, YUM Brands, H&R Block, and eBay. Mr. Knight currently serves as Operating Partner at Thomvest Ventures, a $500M evergreen fund based in San Francisco that specializes in Fintech, MarTech, and Cyber. In addition, he’s founder and CEO of CMO Coaches, which coaches current and aspiring marketing leaders. Mr. Knight is also the co-author of Crafting Persuasion: A Leader’s Handbook to Influence Minds and Change Behavior.

In his latest book, Learn to Leap, Mr. Knight draws from lessons learned in his professional and personal life to inspire readers to take educated risks and reap the rewards. Mr. Knight recently spoke with The Bliss Group about the difference between taking a risk and taking an educated risk, what he considers the most important virtue for success, and more.

Q: What’s the difference between taking a risk and taking an educated risk?

A: It’s the difference between taking the time to do your homework versus hoping you are lucky.  “Look before you leap” means just that – what are the expected upsides and downsides of a major decision you’re about to make?

Q: What are the most important factors to consider when weighing the pros and cons of a particular risk?

A: I’d put risk factors into three primary groups:

  • Financial Risk – How much money are you going to be investing vs. the potential upside (and what’s this assessment based on)?
  • Effort Risk – How much time and effort will be needed to make this happen and is it going to worth the “opportunity cost” (i.e., what you are NOT going to be able to do because you’re working on this idea)?
  • Reputational Risk – If this succeeds, is it going to be something you will be proud to be associated with (vs. something that’s successful but hurts your personal brand)?

Q: How confident should you feel before you commit to taking a risk?

A: If you wait until there is no risk, either someone else will have already done it, or you will have invested more into the effort than it’s worth.  My rule of thumb is if I feel I have at least a 70% chance of succeeding, I’m going for it (and figure that even if it fails, the resulting lessons learned will be my reward).

Q: In the introduction of your book, when you tell the story of your trip to Seoul, you talk about how “the beauty of a low base” made the rest of your trip a pleasant and productive one compared to its harrowing start. How much does managing expectations factor into taking a calculated risk?

A: Getting into the right frame of mind is key if you’re doing something that’s challenging or unknown.  I like to do a 100-mile bike ride every September from the Amtrak station in Irvine to the finish line in downtown San Diego. One of my favorite shirts the bike riders wear is “It’s Supposed To Hurt”.  If your mentally prepared for what you’re undertaking, it makes it a lot easier to deal with setbacks and surprises.  

Q: To write the “A Moment of Zen” segment that closes each chapter, you asked friends and colleagues what advice they’d give their 25-year-old selves. What advice would you give your 25-year-old self?

A: I’d give myself three tips:

  • Be wide open to new experiences – you never know what’s going to come your way (such as the invention of the Internet or rise of e-commerce)
  • Get back on that horse – even if things go to hell in a handbasket, you’ll have learned something valuable.  Keep going!
  • Your “brand” (reputation) is your most precious asset – be true to your brand values.

Q: Do you consider failure or success to be a more effective teacher?

A: Failure is a much more powerful teacher – just so long as you don’t keep making the same mistakes!  The Latin phrase “Memento Mori” is worth keeping in mind – “remember you have to die” – so don’t waste a lot of time on regrets.  Learn from whatever happens and move on to the next challenge.

Q: From courage to respect to helpfulness, each chapter in Learn to Leap is dedicated to a virtue. What, in your opinion, is the most important virtue for success in business and life in general?

A: That’s a tough call but I’d have to go with perseverance.  You are going to have setbacks (and the bigger your dreams, the bigger the setbacks).  Unless you’ve got an abundance of perseverance, none of the other virtues are going to get you to your “better place”.

Q: Do you think our current climate rewards or discourages risk takers?

A: There has never been a better time than right now to try something new or different.  Technology has made starting a new business easier than ever and you can reach huge audiences with minimal investment.  It’s never going to be easy to break through all the competing ideas, but if you have the right focus and perseverance, I like your odds of success.

Q: Is there anyone in the public eye who you can point to as an example of someone who took a risk that paid off?

A: There are plenty of examples, especially in the business world.  Richard Branson.  Anne Wojcicki. Steve Jobs. Sara Blakely. Oprah Winfrey.  Every one of these founders had to overcome a huge number of skeptics, but they persisted, and eventually achieved remarkable results.

Q: What advice would you give to someone facing criticism from naysayers on a risk they are thinking of taking?

A: Recognize that skeptical people are not going to add a lot of value to a conversation.  If they have some legitimate concerns or objections, make sure you take the time to listen and understand their perspective.  But after that, go spend your time with the people that are going to help turn your dreams into reality rather than ones who enjoy sending negative energy your way.

The Bliss Group thanks Mr. Knight for taking time out of his busy schedule to answer our questions. Learn to Leap is available on Amazon, Audible, and through other booksellers.

Photo Credit: Kip Knight