Source Pain

Making ends meet during graduate school at NYU, I took a part-time job at this small company on 23rd street in NYC called “PC Learn” where I worked for two years. I was their sales rep for selling conference space to people who needed external rooms. I learned that companies of all sizes had constant space needs, despite having huge office spaces. I learned how to understand their needs, all the complex logistics involved and learned how to sell. Eventually, I brought on Kaplan as one of their biggest customers.

This was a rare career experience that didn’t fall anywhere on my career spectrum. My full time job was investing, my previous job was investing and next job was, yup, you guessed it, investing. I dont think I have ever mentioned this experience in any job interview or client pitch since then. But it was a big part of my life.

Since college, I’ve spent the last 15 years hustling. I started my own firm at 25 years old and survived for the last 10 years. As a VC investor, entrepreneur and small business owner, I’ve always had one constant: the need to play a little bit bigger than I really was.

I believe this is the aspirational theme that all of us Americans share. We all play a little out of our league and shoot a little higher to get to where we want to go. As I constantly tried to do this, I kept finding one place of solace: luxury hotels and restaurants. With their immaculate finishes and service, luxury brands always provided the setting for aspirations. Whenever I had meetings at hotels, I always felt more empowered. Unencumbered by the limitations of my surroundings at my office, when I was at a hotel, I always knew that whatever I needed was just one quick request away.

One day it all came together. I was in Mumbai working on my last Jina Ventures deal and needed to pitch a major investor and get them over the hump. I knew that no other setting would suffice — we needed to hash this out, look at the materials and just dig in. We couldnt do this in public space. So we decided on asking the hotel for space. It was a big pain, but several hours, emails, phone calls and a signed contract later, we got our room.

It made all the difference.

It was a beautiful symphony of a meeting. It started with ice water and coffee to perk everyone up, print-outs hand delivered to the room, and some sweets to get the blood flowing. As we in the throes of battle, club sandwiches and french fries lightened the mood. Someone put on some light music. Then, session two. As nightfall came upon us, someone broke the ice and ordered the whiskey. Joy was upon us all. Meeting was adjourned. We didn’t close the deal that night but we got damn close. We closed it a week later.

All I kept thinking since then was that this should be easier. This should be accessible and made available to everyone, and it shouldnt take hours to put together.

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