Before all the ladies called me Papi Chulo, I was just regular Rishi “Ricky” Mathur. Ricky was given to me from the powers at Yext. They discovered for me that to do my job properly, I needed to change my name, Rishi was very difficult to pronounce in the midwest. But Ricky just rolled right off the tongue. Anyway, at that time all I did was exercise, perform stand-up, sell powerlistings and constantly swipe right on Tinder. Neither Ricky nor Rishi knew how to prospect properly. Just to clarify before I am labeled misogynist, I would like the record to show I only swiped right on every girl because I am an equal opportunist (not thirsty). Unfortunately, they did not share my views, they on the other hand were very picky. Aggressively picky, to the point where it felt like there was a conspiracy against me.
How I Prospected My Girlfriend GIF

How You Present Yourself Matters

I went to my coworker, he advised me about his methods of using Tinder. He showed me every aspect of his profile is tailored to show a different side to him. He then showed me two types of pictures:

  1. Proper types of pictures to post 
  2. Pictures which should never see the light of day or as he puts it “these need to burn in the cloud.” This blew my mind, it reminded me of how restaurants would enhance the pictures of their food to seem more appealing.

Every Tinder picture reminded me of a Big Mac or chicken nuggets. So I ventured out to create my own chicken nuggets, I took some amazingly photoshopped photos of myself and posted them up on my profile. Soon enough I received hit after hit. Well, it was only 3 girls. But those 3 girls broke my 22 years of silence.

Initial Interactions Matter:

Before I knew anything about my girlfriend, all I knew was that she loved to travel and she was really cute to me. With all that information to work with, I still feared the dreaded blank bar, the bar that constantly taunts you to write on it.

The more I stared at the emptiness the more terrified I became. "No that's dumb." kept swiriling through my head. No matter what message I sent, I felt it would never be good enough for her. I didn't wind up like my friend Brian.

Text message with no reply

This is essentially very similar to a cold email, if I make it too generic I am no different than any of the other Anthony Weiner's sending messages.

If I make it too personalized then she will think I’m a creep. I need to have this message be witty, charming and personalized enough where it doesn’t seem like I am spamming her.

Even after all that, there is still a high risk she never replies.

Email personalization can increase your reply rate by 100%

“...the average open rates for business emails hover between 14% and 23%”.

Do Not Be Generic

“The key to a Tinder opener is attention. This girl is getting 10,000 "heys" a day from a bunch of schlubs who have nothing to offer her. If you send her another "hey" then what makes you worth talking to? Your winning smile? Newsflash. There are winning smiles elsewhere found in nature.”

After studying many dating app messages, I noticed people are boring. But more importantly each of these messages look very similar to a business cold email. Very bland, trying to look exciting and just nothing but value props. So I decided to take an unconventional route, I decided to study one of the top sales reps.

Sample cold email by Jon Mazza

After studying many cold emails, with their amazing responses. I realized there are 4 traits that make a solid cold message:

  1. Keep it short
  2. Be human
  3. Personalize it
  4. Be Creative

Be You, Be Creative

So after an hour of debate, I sent my crush the inevitable question, “Who do you think could win in a fight Oprah Winfrey or Michelle Obama?” I felt this message was precise, mainly because after doing some digging, I found out that she loves comedy. More importantly, she used to be a recruiter, which means she can smell hogwash from a mile away. Also, at the time her favorite comedian was Hasan Minhaj. Meaning she loved fast-paced speaking, Indian men with the sex appeal of a care bear. So what better way to showcase who I am from those 14 words.

After patiently waiting next to my phone for half hour, I decided to occupy my mind with meaningless activities. I went to work, I performed stand-up, I hung out with friends. Finally after a long wait, I got the message “Hi.”

Dancing GIF

This was incredible. Something about me and my message triggered her enough to want to talk to me. Now what?

Build Your Value

“I got so caught up in getting her attention that I forgot to create the interest I needed to make her return any of my affection. Once you have a prospect's attention you need to do something with it. Build the value.”

Seeing this message I knew I couldn’t respond “Hi” it would kill the conversation, but I also couldn’t ask her about her work in the Education space (when I meant digging, I also researched her LinkedIn).

I knew that whatever I say, it needs to help me lead to an in person meet. So I went back to the drawing board, I began to note down everything, like the types of post she liked, types of pictures she posted and types of events she attended. Basically, I studied her for about 2 hours.

I wanted to make sure my next few messages showed that I had common interests as her and that we would be very compatible together. But after all that digging, I noticed she was a very direct person or so I thought. Sometimes you can misconstrue messages and posts.

Here is an actual screenshot of our messages:


To my defense I thought this would be funny, she did not. But to her better judgement, she didn’t hold that against me.

After constant messaging back and forth I started to see a pattern arise, the more we spoke the more I got to know her and the more comfortable I began to feel. We had a lot of common interests, both of us loved comedy, we both wanted large families, have a very similar upbringing, both have older siblings, have similar life goals and more importantly both of us think Hasan should play Aladdin and I should play Abu.

After a few days, I asked her out again and she obliged. Going back through my conversation with her, I noticed that when I carefully prospected this random girl my chances of landing a date with her dramatically increased. Now I am no longer sending generic messages to every woman. I am now carefully crafting messages to those girls I believe would be of interest to me.

One of the reasons she decided to go out with me was due to the level of comfort I provided for her. More importantly, she felt that this could be a mutually beneficial partnership. All of the sales that I ever made were due to the sentiment of comfort. A prospective client and I bonded over something, more often than not food, which then sparked a friendship. Ultimately, that spark leading to a sale.

Posted by Rishi Mathur
Rishi Mathur
Rishi Mathur is the Content Producer for LeadIQ and is one of the most important voices for this generation. Rishi has on many occasions been compared to the likes of Aziz Ansari and Gandhi based solely on his looks. He has helped with the growth of several different startups and has experience in both marketing and sales. He has been published in many major media outlets such as TealMango,, The Oregonian, and Highland Park Planet. He is a champion at building communities and would love to start his own cult worshipping the different cuisines around the world.

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