How I (Almost) Closed a Deal With Mark Cuban, With Only an E-mail

Rodney Gainous Jr.
The Best Publication
6 min readDec 12, 2017

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Hey guys, I want to share with you all the story of how one cold e-mail, turned into a two week negotiation with Mark Cuban.

The Intro

So let’s rewind back about four years ago. I was eighteen working on Runn, an on demand delivery service, with Noah Passalacqua, DAndre Ealy, and Jordan Coin Jackson. This was an exciting time in our lives because although we never expanded outside of Detroit, the amount of knowledge, confidence, and experience we gained outweighed any failures we encountered. One of the many experiences we shared that changed our paradigm of thinking. Hopefully by sharing this, it will shift the limit of what many deem impossible. This is one of many stories I want to share with you all — here we go.

We put 110% in Runn — it was everything, and it showed. We had so much conviction that Runn was the solution to the problem we all faced; getting food delivered on demand. Turns out, it wasn’t just college students this was a fundamental problem everywhere, hence Postmates, UberEats, DoorDash, Tapingo and others. We worked on it everyday, no matter the circumstances. We’d go to school, work, then our office (Bamboo Detroit) every single night. We weren’t solving an easy problem, and it required an everyday work ethic. Faith kept us moving forward. But, when our faith seem to fade every single time life showed us if we continued, there’d be something at the end of the road. Talking to Mark Cuban was one event that kept us moving forward, here’s what happened.

It’d be way too long of a read to highlight every single part of the e-mail chain, so I’ll outline three major points in conversation. What got him interested, working through the details (& a funny tidbit), the ask (& subsequently the pass).

What got Mark interested?

I’ll be straight up with you, at the time I was obsessed with TechCrunch, BusinessInsider, HackerNews, ProductHunt, etc. so I came across tons of content daily. One evening, I came across an BusinessInsider article of how the Box CEO Aaron Levie got an investment deal over e-mail. Simple logic (1 + 1), told me I should try the same thing. So, using my notorious Googling skills I found his e-mail.

How did I, a nineteen year old entrepreneur, from Detroit, get Mark Cuban’s attention?

Well, I’m a pretty straight forward guy so, here’s how it went:

First E-mail To Mark Cuban

That’s it. Now I’d love to say I did something insanely creative, but I didn’t. I understood Mark was a business guy, and his time is limited, so I got straight to the point. Here’s the deck I used: http://rodneygainous.com/download/runn/RUNN_PITCH_DECK.pptx

So, I got a response, but I couldn’t believe it….

Good point.

Not exactly what we were looking for. But, workable. So, what got him interested?

All or nothing.

Looking back, I think 100% of me thought it was the idea. Now that I’m a bit more experienced, I’m 100% sure that I was 100% wrong. I believe it was the persistence, because investors don’t just invest in ideas, they invest in people.

The Details

This chain went on for nine days, so just trust me, I’ll spare you the details and get to the point.

So, what exactly did you talk about?

We’re getting somewhere.

The why, the numbers, the competition. We went back and fourth on these details, but at this point we knew (kinda) that he was interested. This was the most rewarding and stressful experience. On one hand, we were negotiating with someone we looked up to as an investor and tech entrepreneur, but on the other hand, we had no real clue what we were doing. At the time, we were young entrepreneurs figuring out, but I think we did pretty well. We had some help from our advisors, and without them we wouldn’t have gotten very far.

Remember when I said “kinda”, well, at some point we asked him if he was interested. Here was his response:

Oops 🤦🏾‍♂

Oops 🤦🏾‍♂

The Ask

Figured I’d address the elephant in the room right away….

So what happened? What was the ask?
$500k convertible note with a $5m cap, 20% discount in Series A round with a board seat.

:(

Why didn’t you get the deal?
I don’t know. Honestly, I seriously don’t. And to be honest, at the time we were so disappointed it didn’t matter why because we felt we failed. But to be frank, there’s a billion reasons why someone can say no to you and sometimes it’s you, sometimes it’s not — but here’s my theory. It was us, I believe we didn’t get the deal because of the amount, and structure of the deal. The amount we were asking for was way too high, and in hindsight was a bad move on our part. We structured the deal for what was best for Runn at the time, however the deal wasn’t sweet enough. We wanted our cake and eat it too.

The End

Whenever you set out to solve a meaningful problem, it won’t be easy — this is a fundamental truth. But it’s in the pursuit of solving a difficult problem do we grow from experiencing things that you would otherwise assume was impossible. We learned some important lessons: don’t get to ahead of yourself, and only ask for what you NEED. You’re building a business, and you shouldn’t expect a cushion of money to figure things out without TRACTION. But most importantly, we learned we should reach out to anybody and be fearless in our pursuit towards our goals. For us, some young African-American kids out of Detroit and Farmington Hills, we never expected to have the opportunity to talk to Mark Cuban. It was one experience of many before and after, that showed us what’s possible. I hope that you liked this story, and I’m excited to share the others I have.

Thanks for reading and God bless. Mark Cuban if this ever get to you, hopefully you don’t mind, but either way thank you for being down to earth — this made a big impact on our trajectory.

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Rodney Gainous Jr.
The Best Publication

Once 16 making $200K off bots, now the CEO of the best security Safe. Co-host of BeatTheOdds, the best podcast for forward-thinkers.