5 Confessions of an Entrepreneur - Part 1

In the first part of my “5 Confessions of an Entrepreneur” series, I share the reality of my life over the past 1.4 years. This entry is mostly centered around the experience of my entry into social media.

1. I’ve never been this poor — Indeed, I did “go for broke” to realize the opportunity I created by chance over a year ago, but I didn’t expect to be broke — literally. In all my years of making money, this has been the bleakest period ever financially. In some ways, I guess you could say reality brought my high expectations to a screaming halt.

2. I wanted to quit — and more than once — When I initially launched the Interviews Podcast, it was all about fun and trying something new. I honestly had no idea that I was embarking upon a life changing industry. Within a few months, after receiving high praises for my production work and interviewing abilities, I then realized the “bigger picture”.

Unfortunately, even with the great interviews I was producing with CEOs and celebrities, I wasn’t making any headway with monetizing my work. This left me uninspired, depressed, and sometimes angry.

3. I took some things to heart — In an attempt to better my life and security overall, I started approaching some major companies to sponsor Interviews. I have ZERO experience in sponsorship marketing, but I did have the drive and something of value. My positive outlook and attitude led to a positive reception at Cisco, which liked the idea of Interviews and the people who appeared.

Unfortunately, even after several “thumbs up” within the marketing areas of Cisco, their top marketing guy never even as much acknowledged his subordinates or my inquiry. Suddenly, Cisco was a target for dart practice, and my mostly tamed ego lost control:

“For crying out loud, who is this guy to ignore me and my work? Hell, I’ve commanded the respect of people far more important — and richer than this guy (like Bill Gates, for example)”

“The nerve of this guy to simply ignore me after receiving such a positive response from Cisco’s other marketing people — damn him, and Cisco! They’re not the *only* game in town”

After months of dealing with Cisco’s unofficial and unprofessional rejection by their top marketing guy, I got over it and moved on.

4. I grew tougher skin through rejection — One thing I never dealt well with through adolescence and most of my 20s was rejection. Personally, I always took it as a poor reflection of myself and that people simply didn’t like me for whatever reason — which, primarily, was caused through dealing with women and, indirectly, affected other parts of my life.

Through being rejected by people for major interviews (yes, I tried to secure an interview with Oprah — hey, I always think big, and have succeeded several times — so why not?) and sponsorship, I grew immune (mostly) to rejection. I wasn’t losing sleep anymore, nor did I agonize over being the little guy trying to “land the big fish”.

5. I am still trying to find the perfect balance — 40 great (and major) interviews later, with more than 100,000 downloads, I am still trying to find a balance between doing something I enjoy and realizing a living from it. One thing I’ve learned in my experiences thus far, is not to read too much into people’s “promises”. You’d be surprised by the number of people who have volunteered a number of things to “help out”, but always fell short of on their word.

So, rather than be “excited” about a proposition, I’ve learned to simply “wait and see” before assuming something’s a “done deal”.

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