How to Pitch Mark Cuban via Cold Email

Advice from founders who got investment, Mark Cuban himself, and my own personal experience.

Hello 👋

Martin here. Welcome to another edition of Founders’ Hustle!

I produce content about the “hustle” of entrepreneurship and building startups.

Today I’m sharing insights on pitching billionaire Mark Cuban for investment via cold email!

  • Founders have secured funding commitment after a “quick” email exchange. 📩

  • Simple steps will increase your chances of a reply dramatically. 📈

  • There’s one thing he absolutely can’t stand that’ll get you blocked. ⚠️

It’s no secret Mark Cuban welcomes entrepreneurs to pitch him via cold email. 

As a self-confessed “grinder at heart” he appreciates the hustle and regularly makes investments in founders who send them.

My email is pretty public, so I get pitches… and I’ll respond directly” 

Mark Cuban

With a pretty broad appetite across many industries and funding-stages, the founder of and current Dallas Mavericks owner attracts all kinds of proposals.

Interestingly, sometimes he ‘cuts a check’ without even speaking to founders outside of an email exchange — it’s the most efficient use of his time.

On the occasions where he’s not “fully versed” on a particular market, someone in his team (with appropriate expertise) will pitch in to scrutinize the opportunity.

This approach has led to investments in companies that became very successful. Notably Box (albeit with an early departure), Datanyze, FiscalNote, and The Zebra.

As a ‘household name’ billionaire and possibly the most famous investor in the world, he receives a lot of email pitches per day — 750 to 1,000

That’s some pretty incredible deal flow.

Pretty phenomenally, he claims to read them. 🤯

Well, at least the first one or two paragraphs. 

It takes him two seconds to decide whether to reply to an email or not.

I’ll read the first paragraph or two and if it is something that catches my attention, and is interesting and I think is forward-thinking, then I will just start peppering them with questions.” 

Mark Cuban

The vast majority of cold emails are deleted:

I only respond to about five percent of them. And to five percent of those, I ask follow up questions.

 — Mark Cuban

Cutting through this intense noise and establishing a two-way dialogue is the first important step towards securing investment from him.

Ultimately, the Shark Tank star will only put money into companies in which he believes in the founding team and idea. But, there are a number of things you can do to improve your chances of receiving a response from him to verify that (or not).

I experimented with this personally some time ago. 🧪

Previously, I shared a template I often use to cold email highly successful people. But for Mark Cuban, I utilized a different — direct — approach. 

More like a quick pitch than an ‘ice breaker’ or ‘conversation starter’. I’ll explain why.

First of all, Mark Cuban likes emails that “get right to the point”, as he explained on the Raising The Bar podcast. Removing unnecessary fluff, backstories, and pleasantries is key.

Grandiose non-sensical claims like “the next Uber” are turn offs, as is persistent emailing day-after-day if you don’t get a reply. The latter behaviour will end up with you added to his Gmail auto delete filter.

Also, make sure your email copy is straightforward and ‘stage-appropriate’. 

All you need to do, initially, is break the ice. Discussing ‘in the weeds’ detail like your current agile sprint or latest marketing campaign ‘right off the bat’ is likely overkill and confusing. 

My initial email objective was simple. Illicit a response. That’s it.

Going in with the objective of ‘closing’ him would have lead to a lengthy and bloated first email — a mistake that many passionate founders make. There’s just simply too much ground to cover to do that.

So, I drafted a short email and fired it off to his Gmail account. 

But, he didn’t reply. 🤔

I waited a couple of weeks and sent another reworded email. 

Again, no reply. 😬

Just over two weeks later I sent another reworded email.

Third-time lucky? Nope, no reply. 🙁

I also tried other corporate email addresses. Each time I altered the presentation, angle, and language used. This includes the title also.

I left it a little while longer and sent another reworded email.

Success! This time I got a response. 😁

The title I used was one of those ‘X for Y’ startup analogies. For example ‘Airbnb for pets’ or ‘Stripe for health’. 

The body of the email was a handful of punchy short sentences. 

1st sentence: Problem (15 words)

2nd sentence: Solution (16 words)

3rd sentence: Why it works (13 words)

4th sentence: Progress to date (10 words)

5th sentence: Market size (10 words)

6th sentence: Question (7 words)

His response was brief. And, basically a polite no. 

The exact words used were “a solid maybe”. This was less subtly reaffirmed as “a solid no” when I circled back later.

That was helpful and I appreciate he took the time to reply.

Obviously, it was not the most ideal outcome, but I had an answer and could move on. After all, most investors founders contact do not invest

Minimizing the time spent chasing folks who have no intention of investing increases productivity materially. 

Since I didn’t make it beyond an initial reply, I’m going to share feedback and experience from founders who cold emailed Mark Cuban and went the full distance by securing investment from him.

One theme I noticed across all of them was serendipity. Numerous founders emailed Mark Cuban around the same time he was already thinking about the problems they were working on fixing. ⚒️

First up is Adam Lyons, founder of The Zebra. His advice:

Be yourself. After launching his company in a friend’s basement, where he crashed while living off unemployment checks, The Zebra founder conveyed his personality and the ‘casual’ way he usually operates from the very first email. He didn't try to be ‘someone else’.

For example, the email title he used was informal: “Wanna disrupt the insurance industry?” 

With an investor or somebody you are… going to spend a lot of time with, you want to get along with them.

If you are dedicating your life to a project, then you are obviously pretty excited about that project and you believe in it, so how would you articulate and share that with somebody? That’s the goal.

Adam Lyons

He also said you should demonstrate progress and not just rely on a vision:

A lot of folks want to talk about an idea that they have. 

Well, everybody has an idea. You want to talk about what you have done, and the progress you have made.” 

Adam Lyons

Adam Lyons reached out to Mark Cuban at the perfect time. ⏰

The tech billionaire had already been thinking about how the market The Zebra was tackling was ripe for innovation. 

Next up is Tim Hwang, co-founder of FiscalNote. His experience:

After building a prototype with his founding team and signing some beta customers, he went on Google, searched for Mark Cuban’s email and sent him a simple and short email (from a Motel 6!) that went along the lines of:

Hey, Mark. I’m working on this idea. I feel like it could really change the way that the world understands laws and regulations.” — Tim Hwang

Mark Cuban responded within 45 minutes and asked a bunch of follow up questions. Quickly, the CEO of FiscalNote had a lead investor and a check for $740,000.

“ [The whole process]... was a bunch of emails back and forth. I think it was one phone call with somebody on his staff, and it basically took a couple of days. Mark moves quickly, and I think he knows what he wants.” 

Tim Hwang

Next up is Ilya Semin, founder of Datanyze. What happened:

The now exited founder of Datanyze cold emailed Mark Cuban about his B2B business intelligence solution and attached his pitch deck. But, he wasn’t “really expecting a response back anytime soon”.

Within an hour there was a reply in his inbox. 📩

Definitely interested — Send me more details.” — Mark Cuban

This became a $2 million seed round with IDG Ventures and Google Ventures also joining.

The biggest lesson I learned was: If you want advice, ask for money. But if you want money, ask for advice.”

 — Ilya Semin

Next up is Aaron Levie, co-founder of Box. What happened:

Aaron Levie picked up a $350,000 check for his company Box after cold emailing Mark Cuban about a marketing opportunity, not investment. 

This was back in 2005 when the tech billionaire had “one of the more popular blogs on the Internet”.

So we actually saw him as a sort of marketing and awareness channel for the product…you know… ‘Hey Mark, can you write about this company that we are building’.

And he responded, saying he’d be investing. 

It was really serendiputous that he had been thinking about the space a bit, and we got lucky that it sort of aligned with his interest.

Aaron Levie

Three more case studies

Tim Ellis, co-founder of Relativity Space, cold emailed Mark Cuban and picked up a check for $500,000 after two months of due diligence. 

He used the email title “Space is sexy: 3D printing an entire rocket” and believes he got a response because of his founding team’s strong professional pedigree (ex-Blue Origin and SpaceX engineers). 🚀

Reggie Renner, CEO of ZergNet, raised $30,000, then later a lot more, after sending a cold email in the middle of the night.

Mark Cuban “loved the idea” and said “[Reggie] was very detailed in his response”.

Apparently, the tech billionaire originally said “no” to ZergNet, but, after some negotiation, changed his mind because of the valuation. The round was “cheap”. 

Dhruv Ghulati, CEO of Factmata, a startup that’s fighting online misinformation and uses AI to provide a quality score for content, cold emailed Mark Cuban pre-revenue. 

It was a strategic move, he shared on the Growth Leap podcast.

The UK-based founder deliberately chose to approach Mark Cuban because he was “a political figure” who had “showed some interest in the election and had been involved in the conversations around Trump”.

Due to this, he thought “Maybe [Mark Cuban] would get what I’m trying to do and would be willing to give it a shot without much diligence and actually just back the vision and idea that we had”.

It seems there were some “hard questions” around monetization, but a well-articulated plan explaining how they would explore and establish a sustainable and scalable business model sealed the deal. 🤝

It ain’t over till it’s over

Remember, if you get a “no” from Mark Cuban initially, it’s not a ‘forever pass’!

He is open to you circling back later with an update on the progress you’ve made, assuming it adds credibility to your vision and plan.

If you can come back and make the idea better, or you’ve learned something, it’s not a bad thing to say, ’Ok, when I first emailed you last year … we didn’t have a prototype, or we didn’t know this yet

 — Mark Cuban

Until next time!

Martin 👋

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