Half my deals come via referrals from people I know and trust — mentors, fellow angels, former employees, etc. (e.g., Say:Media, 140Proof, Fab.com). Thank you friends! The other half are deals I find on my own — companies whose products I love and/or entrepreneurs I admire (e.g., Twitter, TheRealReal, MommyCoach)

I’ve gotten to know Giordano Contestabile (@giordanobc) because we’re both early investors in TheRealReal.  We both made very early bets that Julie Wainwright would build the world’s premier online consignment shop and that’s precisely what she’s doing!  SHE IS KILLING IT!  You’ll hear a lot more about TheRealReal in the coming months because Julie is building a break-out company — a unicorn in the making.  Really!

Back to Granify.  In September, @giordanobc introduced me Jeff Lawrence, the CEO of Granify.  Jeff and team are building what I believe will be an ecommerce powerhouse based on a simple mission: help online retailers make more money.  How?  Granify tracks your customers as they travel through your ecomm website, predicts whether or not they’ll buy and if they’re predicted not to buy, understands why, then presents them exactly the right message at exactly the right time.  And BOOM! they convert.  SWEET!  If you talk to any ecomm CEO, she/he’ll say their biggest headache and their biggest leverage point is on-site conversion. #TRUTH

Jeff and I chatted.  I was impressed. I like simple solutions to complex problems.  I like that their dashboard tells you exactly how much you’re making from their service.  I like that they only make money if you make money.  I like companies that productize rather than servicize solutions. The ecomm space is massive.  

BUT Jeff was in Edmonton (that’s in Alberta, Canada —  just a quick 4 hour and 12 minute flight from NYC) and I couldn’t break away to buzz up there and meet him.  It’s also fiendishly COLD in Edmonton (it’s the northernmost city in North America with a population over one million, according to Wikipedia) and I’m a warm weather friend.  (Today Edmonton will reach a high of 10).  Initially, I was concerned that the company was in a relatively remote location. But then I thought about Omniture.  A billion dollar exit.  Built in Utah, not Silicon Valley.  OK.  I started thinking remote might be good — if it’s cold, people stay indoors to write code and mine data. Hackathons and investor pitch contests are not an everyday distraction. OK I’m warming up.  Granify kept coming up.  I had lunch with another NY angel, Jerry Neumann @ganeumann who worked for the private equity firm that took Organic private back in the early 00s when I was the CEO.  He could have been a d*&k back in the day but wasn’t.  In fact, he was — and is — a super nice guy.  It turns out that Jerry is also an investor in Granify.  I figured it was worth another look.  Jeff made a trip to NYC.  His story was even more convincing in person and he closed me on the spot.  Yay!

I’m an art lover and like many NYers I make the rounds to the big shows when they swing through town.  I particularly enjoy the Outsider Art show.  The work is fresh, dynamic, unaffected and unfiltered.  If you like art porn, check out Eugene Andolsek — a true savant (see photo above).  I have a few of his works.  As an investor I’m a bit of a contrarian and certainly an outsider.  I don’t do the cool kid deals because I’m not a cool kid (I never was).  Just sayin’.  

Three of my recent deals are “outsider deals.”  They’re outside the Silicon Valley/Alley bubble.  OfferUp is in Seattle.  Snapwire is in Santa Barbara.  Granify is in Edmonton.  I see a pattern here.  

What do you think?  Do you shy away from OOT deals?  Or seek them out?