Thursday, March 2, 2017

A Successful Career--But My Best is Yet to Come!

Posted By: George Deeb - 3/02/2017


& Comment

I recently passed my 25th year of being in the work force.  Most careers span around 50 years, so at the midpoint in my career, I figured I would do a little self-reflecting on where I have been, where I am, and where I would like to go, to see if you guys can help me better achieve my goals in my next 25 years.


Credit Suisse First Boston (8 years).  My investment banking days in New York were pretty amazing.  It really honed my financial, strategic, fund raising and M&A skills.  And, as an expert in the retail industry group, it was exciting to work with the CEO's and CFO's of some of the nation's largest retailers (e.g., Home Depot, Babies R Us, Saks Fifth Avenue, Pep Boys).  It was really a meteoric rise for me, starting as a financial analyst, getting promoted to associate without needing an MBA (the only person in my class to do that) and ultimately rising to the level of Vice President.

I loved the big paychecks for a guy in his 20's.  But, the transactions started to become routine (e.g., the 4th IPO was no different than the first three).  And, all I could think was, I would rather be the entrepreneurial CEO of the companies I was taking public, that grew their business from zero to $250MM in sales, and got a huge financial windfall by taking their companies public.  I was too creative and entrepreneurial, and needed to make a change, even at the expense of cutting off my "golden handcuffs" in terms of compensation.

Overall experience:  A
Overall happiness:  B+

iExplore (10 years).  With the dot com boom in full swing, I figured the timing was right to make my leap from investment banking to building a startup.  I was a passionate adventure traveler, and new the process of booking a trip was very cumbersome, and that the internet can make it better.  And, apparently, we struck a chord with other travelers, as we ultimately attracted over 1.3MM unique visitors per month to our website.  We cut a deep strategic relationship with National Geographic, and powered the adventure travel sections of many large travel sites (e.g., Expedia, Travelocity, Starwood, Fodors, Frommers, Lonely Planet).  My creative and entrepreneurial juices were constantly flowing, and I really loved what I was doing.  It was here where I honed my business, marketing, branding and product skills.

But, the travel industry was very cyclical.  And, when times were bad (e.g., after 9/11/01), they were really bad, making it tough to scale, especially when consumer marketing was so expensive in the crowded online travel space.  And, having raised venture capital from outside investors, I needed to get them an exit at some point.  So, we ultimately sold the business in 2007 to TUI Travel PLC in London, the largest seller of leisure travel in the world, with over $25BN in sales.  I lasted two years with TUI, before the politics, procedures, processes, travel time and slow speed of a big European company tooks its toll, and I moved on to my next business.

Overall experience:  A+
Overall happiness:  A+

MediaRecall (2 years).  I didn't found MediaRecall, a B2B digital video technology and services company.  Their founders had already built a great product and needed help scaling their company.  So, I acquired a third of the business and became their CEO in late 2008.  We had a strategic relationship with Getty Images, around the clipping and monetization of stock footage, and had established customer relationships with many of the large film and television content owners, or their partners (e.g., National Geographic, BBC, Deluxe, Johnny Carson, Oprah Winfrey).  It was here where I built my enterprise B2B sales and SaaS experience.

One of our customers liked us so much, they ultimately wanted to buy the company.  As we were deep in digital services, where their strength was in film services (which was not the future).  So, Deluxe made us an offer we couldn't refuse in 2010, and we sold the company to them (including an earnout with the potential of a 10x return).  I was expecting another five year run when I joined the company, so we sold a lot sooner than I thought we would.  But, I found myself with time on my hands, and not knowing what to do next.

Overall experience: A-
Overall happiness:  B+  (liked B2C of iExplore, more than B2B of MediaRecall)


Red Rocket (7 years).  I founded Red Rocket to find another business to invest in and become CEO, as I did with MediaRecall. I never intended it to become a business.  But, with the success of the blog readership (almost 1,000,000 reads to date), leads started coming in and I have been staying busy full-time helping clients with their growth strategy, execution of financing needs.  I have been approached by over 800 companies during this time--in the $0-$20MM revenue ranges--including the good, the bad and the ugly.  A few bigger clients got me engaged in more longer term, outsourced CMO roles, which were my favorite projects to work on.

But, consulting to CEOs is not the same as operating as a CEO.  As a consultant, (i) clients are typically looking to you for solving a specific project-based painpoint (e.g., 3-6 month fixer upper, not long term engagement), and (ii)  you do not have any control over the upsides or the outcomes, as you are not the one "driving the bus" (which makes taking equity-based roles hard to do, unless you really trust the CEO you are working with).

Overall experience:  A-
Overall happiness:  B


Red Rocket will be a great thing, when I am closer to retirement age and looking for fun projects to stay busy and keep me intellectually stimulated.  But, with me on my mid-40's, I still have way too much energy left.  And, I feel like I haven't done my best work yet.  I am driven to building something really big and great, where there can be a big financial pay day at the end of the build (as I am never going to create long term wealth as a consultant).

So, to that regard, I have been on the hunt to get back into the CEO chair (or CMO chair for a more established growth stage business where I trust the CEO).  I have been exploring all avenues to getting there--buying a company, executive recruiters and working my network of relationships.  I would consider B2B or B2C companies, but as I mentioned above, B2C are a lot more fun for me.  And, as for geography, I would look at acquisitions anywhere, if easily relocatable, and executive roles primarily in the major technology markets.

The goal is to find something where I can get my experience and happiness factors to both score an A+ again.  I need that adrenaline rush again, like I had at iExplore, this time driven with all the business learnings and experience I wished I had had the first time around.


As you can see above, my experiences have been all over the place--investment banker to Fortune 500, CEO of early stage startups, advisor to growth stage companies, outsourced CMO, etc.  Across a wide range of industries--retail, internet, travel, media, services, technology, ecommerce, SaaS, etc.  So, people looking at my background cannot label me in any one bucket, which puts me at a disadvantage versus executives that have only been doing one specific thing over their career.  All, I know is, I am a quick study on anything new I try, and I have been largely successful at everything I have ever done.  My smarts and natural business instincts have always served me well.


Think you or someone you know is building greatness, preferably in the B2C space.  Is your company willing to take on a new growth-driven partner in your adventure, preferably as CEO (or CMO for the right company).  Or, are you willing to sell your company to a new investor group, lead by Red Rocket.  Are you large enough that you are not a broke startup, but actually have over $500K of profits for me to apply my sales and marketing magic to help scale the business, without the need for raising outside capital?  If this sounds like you, let's talk!!  Feel free to email me via the contact form at the bottom of this page.

For future posts, please follow me on Twitter at: @georgedeeb.

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