Early in my amazing real estate career where I rose to being Chicago’s #1 real estate broker, named by the Chicago times and #1 real estate re-development holder for Oprah’s TV studios, I asked my mentor Wes Irvine, who leased the Sears Tower and built 200 South Wacker Drive, “Wesly, how do I know who to trust and who not to trust?”

I didn’t tell Wes, I had too much shame at the time, that I had no trust skills because I was severely abused by my father for 21 years.  I was freaking out.  So much of real estate is based on trust.  You really only have a handshake and millions of dollars in commissions are on the line.

Super broker Wes Irvine had hired me away from the interior architecture world at the tender age of 27 for a hefty draw, unheard of for a real estate rookie.  Wes could spot talent.  And I had broken all RMM Inc. sales records landing over a million square feet of headquarters projects in a single year.

Sadly, my stellar performance was driven by low self-esteem and I never rested.  But Wes was a shrewd New Yorker transplant to Chicago, brought to the Windy City to fill 4 million empty square feet for Sears by Cushman & Wakefield, and he knew he had dynamo in Ken Sheetz.  We both became wealthy together and made his new firm Irvine Associates a force to the reckoned with

Wes seemed not to hear me as we raced up Adams Street with lease documents to shuttle from between landlord and tenant for signatures on my first 6 figure commission.  Though brand new to brokerage I was bringing in huge assignments to represent big tenants right off the bat.  I was a natural salesman with superb training and unique skills as an interior architect no other broker in Chicago could match.  Within a short time I was leading the city as one of the top ten producers of big deals and agencies to represent major new skyscrapers.

But for now I was a wet behind the ears rookie with a lot to learn.  And I was paranoid about losing clients and losing my new home with my wife pregnant with my first child.  So I asked again, “How do I know who to trust, Wes?”

Wes smiled a confident smile and said with his thick Brooklyn accent, “You never know who to trust.  What you do is trust everyone until they fuck with you.  Then you never fucking trust them again.”

Wesly Irvine’s wisdon was pure genius, worthy of the shamans and spirit leaders like the amazing Patrick Flanagan, Father of the New Age, that I meet in my film career of today.  A film career I began after I lost all trust in the system of banking behind real estate and the corporations.  It all shifted I lost trust.

I continue to this day placing my full trust in people until they fuck with me.  Then I move on.  Fuck overs happen even in conscious film work but less so than real estate.  Perfection is an illusion.

Today I love promoting greats like Patrick and his amazing wife Stephanie Sutton and Don Miguel Ruiz, author of the Four Agreements, Tony Camacho of The Gateway, SpiritQuest of Sedona and more.

Take my word for it.  Wes’s Sopranos’s style philosophy, gained from clawing his way to being Chicago’s top broker before me; trust people and organizations until they fuck with you.  Then never trust them again.

You will be vulnerable and you will get badly hurt at times.  Some horror stories for you.  One donor comes to mind who stiffed me on their contribution to my Antarctica meditation and nearly left me stranded at the end of the world. Next a certain ranch owner who slowly kept whittling down our deal of tranpo, food and room until I said “fuck it.”  Then I recall a partner who schemed to take over my skyscraper project who had promised he’d never fuck me.

But worst was an ex-wife who, from my point of view and I acknowledge it as such and I know she sees it otherwise and perhaps rightly so,  took everything we owned from me when we protected our assets from the banks, legitimately and with great care, when the real estate market crashed in 1991 (rents have never come back to where they were after 22 years) by putting all things in her name.  She promised after the danger with the bank had passed to return to sharing our wealth as before we were in Defcon mode.  But she refused and I sought separation.  She served me papers, divorcing me at the low point of my life, rather than trusting I was lost and going through hell.  I loved her like I’ve loved no other woman.  I would perhaps have come back.  We never got that chance.  She moved out of fear taking advantage of advice that the first person to file has the upper hand in a divorce.

But worst of worst of all, my ex poisoned the love and trust of my two dear kids.  I do not resent my ex for she was deeply influenced by the toughest divorce lawyer in Chicago and bolstered the fear of my ex-mother-in-law who hated me for no other than I loved her daughter. My kids will be back one day.  The stuff my ex stills clings I didn’t need anyways.  Yeah, Talk about breaking trust and getting hurt.  Trust is not easy.  And I do not bring up this deeply personal story of the end of an 18 year marriage over broken trust lightly but to illustrate how painful trusting can be.

So occasionally you will get fucked over big time for trusting, severely fucked, but accepting this you will feel less stress and people will rise to your trust 90% of the time.  You will thrive and live without fear and those around you will love you for trusting them.

In 1988 I rose to the top of real estate world on trust.  And built One North Franklin for $162 million, the lobby of which is pictured here.  Pure perfection.  Link to full building description.

t doesn’t happen as much anymore since I’ve been away from real estate nearly 20 years now, but as recent as a couple of years ago I did some consulting on a new skyscraper being built in LA by one of my film backers.  I could walk back into that world easily.  I hope to build again when I find money people with integrity.

One last thought on trust.  Sears walked from their mortgage when the markets crashed in the early 90s that ended my real estate career.  Our whole economy is operating outside trust and integrity now. 

People are all we have left to trust in.  Love and trust them all until they fuck with you and then never trust them again.