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  • Writer's pictureCory Cleveland

Consider This: Observations of 100+ Interviews

Insights from interviewing over 100 CEOs and financiers


My name is Cory, I am the President of Creative Return and the host of The Insider’s Guide To Finance. The following are my insights and learnings from the interviews and dealings I have with talented entrepreneurs, operators, and financiers. I hope you find them valuable in your endeavours.


We are now well over 100 interviews on the Insider's Guide To Finance podcast.


From bankers and financiers to CEOs and highly successful founders; hosting this podcast has surfaced insights that are worth sharing. Here are a couple...


First, let's recognize the power of the red recording button and the opportunity it is hiding. Without fail, when we hit record, the demeanor of every guest changes. For some, it has the power to make them fumble words, for others, it turns on a calculated 'media mode'. Most all the on-record conversations have been interesting and informative, but it is the elusive pre and post-recording conversations where the unique (by definition of the word) person shows up.


The guests who are media-trained know that when the red light is on, the script is in play. Even a respectfully probing layup of a question is responded to with a rote response that fails to convey any real personality. Sigh...


Is this media mode a bad thing? I argue yes.


In today's fast-paced, hyperbolic media environment there is a dearth of authenticity. In that lies an opportunity to differentiate. It is to aim to be human again, embrace imperfection and show some vulnerability. We are inundated with fabricated looks and statements of success.


So what would happen if you recognized failure, shared real lessons learned, and conveyed the quirks of your personality? Some of our guests have done so and magic happens. If I use our listener feedback as a proxy, people are far more interested and supportive of those who put themselves on the line.


Next, let's talk about what I now call "the Common Thread".


Throughout our interviews with some highly successful entrepreneurs and CEOs, the Common Thread is that of a nonchalant intolerance of obstacles and a devotion to direction.


In their tone and their words, you can hear a confidence that nothing is insurmountable; rather an embrace that obstacles can actually be opportunities.


Next, using different words, they all expressed their commitment to an articulated destination supported by espoused beliefs. To sum this up is business 101 - Vision and Values. This combination of pursuing vision while sticking to values creates a level of confidence that, as I see it, enables remarkable success.


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