Dean Clough

June 26, 2023

Portico Darwin: Lottery Winner, Part I


<5 Minute Read
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Happy Monday.  While we certainly had a wonderful time in New Mexico, there is nothing quite like coming back to SF, especially after being away for an extended period.  Quite a change from sunny and 100° to foggy and 60°, and while I certainly enjoy my Pool Boy antics, it is nice to feel that clear, cool ocean breeze once more.

And that leads me to another one of my posts on gratitude, but hopefully, this won't be another maudlin self-searcher.  Instead, while it may first appear to be a ginormous self pat on the back, I present my winning lottery tickets.  In other words, the times - by chance - things turned out really, really well.  I do this not to brag (much), but to encourage you to consider your own winning lottery tickets.

Let me begin by saying that, with the exception of a pretty bad bump at the end, my personal and professional life has been charmed, to say the least.  That is evidenced by the fact this list must span three blog posts.

I have had a number of extraordinary people in my life, and of course it all starts there.  But I've also been very lucky, with a big part of luck being prepared for opportunities when they present themselves.

So let's recount the several times in my life I won the lottery.  At least virtually.  And by that I mean how things could not have realistically turned out better for me.  But a lot of it was chance.  And yes, luck.

And I'd love to hear about any reader's own lottery winners - we all have had them.

1.  Born White.  Born Male.  Born Middle Class.  Born during the Baby Boom in the USA.
The first is the easiest.  There is no bigger impact on one's destiny than where and to whom you're born.  I was certainly no different, and overcome adversity I did not.  Remember that when you think you've hit a home run, yet actually started on second or third base, like me and most reading this.

2.  I Was Not Good Enough for Florida State University
After one year's misguided attempt at becoming an aviator at Embry Riddle Aeronautical University, I got serious and applied to a more general-purpose university.  Except my B average in high school and at Embry Riddle, and the pilot-focused academic standards of the latter, meant I was rejected from FSU in Tallahassee, Florida.

My entire life changed because I was not admitted, as it almost certainly would have meant a life centered in the East, vs. the West.  Nothing that follows would have happened!

3.  I Copied Well
So I went to Embry Riddle for two more semesters, focused on transferable courses, and boosted my GPA.  But what to study and where to do so?  Well, here's a case where the people with whom you surround yourself really matter.  Because my childhood (and we're still close) pal Steven Simon had chosen Management Information Systems as his major at his college, and I figured heck, if that major is good enough for Steven, it's good enough for me.  MIS it was - and that set me on a technology-centered career trajectory that allowed most of my reasonable professional dreams to come true.   Cheers, my friend.

4.  Pictures Matter
But where to transfer and get this MIS degree, and be like my hero Steven?  True story:  somehow, I got a copy of the catalog for the University of Colorado at Boulder.  It had a picture like this on the cover, and let me tell you, this boy raised near a meat packing plant in Albany made his decision quickly.  I applied, got accepted, and the West became my destiny.  But there was no other reason than the catalog photo:  a diff, less appealing photo may very well have meant a town other than Boulder for my next destination - pitiful, but true.

5.  I Met Laura Carson
That's her real name - I don't make up fun names for people I'm pretty sure had my beloved grad gift from my parents, a new, 1985 VW Golf GTI, stolen.   Huh?

Well, you see, Laura was a classmate of mine at the University of Colorado, and we became friends and worked on a couple of senior-level class projects together.  And while it ended badly - see below - if I don't befriend Laura, I don't end up in Albuquerque later.  And no Albuquerque, no nothing of the rest of what I know as my life.

6.  A Most Meaningful Summer Job
If you know me, you know the name of the late Scott Edwards.  Apart from my parents, no single person had more of an influence on my professional life than Scott, and it all began with an internship I landed during the summer of 1985 at his start-up in Boulder, called Sportnet.  After graduation, I took my first full-time position there.  Look at me:  Information Systems Manager!  No one, including me, knew what one did, but no matter!

This idea crashed and burned, and Scott and I literally closed the office door together and shut off the lights at the end.  Later, I started a second company with Scott in the SF Bay Area in the mid 1990s.   

And don't get me started on Scott's ex-wife, Elizabeth "Polly" Michaels.  She's become like a sister and her and her boytoy Primo Harvey, PhD. are great friends of ours.   

7.  The Leasing Agents Flirted More at Spring Park vs. Mountain Run Apartments
After Sportnet failed, my old chum from Boulder Laura Carson reached out and said I'd be perfect at a start-up she was with in Albuquerque.  I interviewed, landed the position and moved to Albuquerque in early 1988.

But where to live?   Well, there were two very nice and new apartment complexes, in the scenic far northeastern quadrant of town.   I came very close to putting a deposit down at Mountain Run.  But in the end, I met Colleen Larkin, a leasing agent at the neighboring Spring Park, and well, she flirted more with me and was more adorable.  Is that sexist?  Regardless, you can see for yourself with this photo, snapped at Grand Central Station in NYC over 15 years later - we became great friends.

But cute leasing agents do not typically equate to winning a lottery.  In this case, however, moving in to Spring Park Apartments meant I would soon meet Kevin Kilpatrick (real name, although we nicknamed him "Kilchubby Head" because he was a goof at times).  And why on Earth does that matter?

Well, Kevin was a marketing rep for Purgatory Ski Resort, in southern Colorado.  Kevin, upon partaking in the rather dynamic social scene we had, said we should start a ski club, and if we did, he could give us free lift tickets and lodging.

So while it was cool to be the founding president of the North Eubank Ski Club, it was even cooler that a young receptionist hottie by the name of Julie Taylor decided to attend a meeting during the summer of 1989, in the interest of landing a date or two.  Boy, did she. 

(Oh, the car.  You see, I did a better job at the start-up in Albuquerque than Laura Carson herself, who had recruited me.  The investors saw that, and let her go.  I am pretty sure she thanked me by having my car stolen; it was found stripped and destroyed on top of a mountain outside of Santa Fe.  A colleague told me he had overheard Laura's husband talking about it in advance.  True story).

8.  Greg Houghtaling (A.K.A. Jay Howling)
I have written about the sad end of our friendship previously, but in 1990, we were still very close and Greg was in the employ of Ernst & Young, the big accounting and consultancy firm, in Houston.  Now, firmly in the clutches of love and a pending wedding, I reached out to Greg - I knew I needed to stop the entrepreneurial dalliances and get real. 

Greg got me in.  Julie and I moved together to Houston in the summer of 1990, and started our lives together.  And the Ernst & Young seal of approval on my ass would prove pivotal, both practically, as well as in schooling me on the type of big projects and programs I'd soon go on to lead myself.

Here we are in Beverly Hills in 2011.   Note me kissing Greg on the cheek.  This boozy habit would prove to be quite an interesting issue just 8 years later.

But how did we end up in SF, in a magical rent-controlled apartment?  What was the winning ticket that brought me to London?  What led me to start Casa Integration, the success of which allowed me to retire at 56, after a kiss on a cheek went way way wrong and The Presidio Trust missed out?   

And what are this week's winning numbers?

You'll have to stay tuned.


Thank you to any one that is reading this newsletter.


Of course, it's the song "Winning" by Santana, easily one of my least favorite songs by him.   

But that's kind of like life:  one must take the bad with the good.  Like "Waves Within", my favorite song by him, and one of my favorites by anybody.

About Dean Clough