We are in the middle of a pandemic, life will not return to “normal.” Now is the time to do the things you are afraid to do.

Now is the time to reach out to the people on your wish list of impossible people to contact.

If not now, when?

As my friend, Paul C. Brunson says, go ahead, shoot your shot.

I took my shot a few days ago. I sent a cold email to Mark Cuban to see if he would let me interview him. And you know what?

He said, yes!

How To Send Cold Emails
Before I get into the interview, let me address the question many readers will ask: How do I write a cold email to someone like Mark Cuban and get him to reply?

Here are three tips to help you send more effective cold emails:

  1. Put the person’s name in the subject. Campaign Monitor says putting a name in the email subject increases the likelihood of it being opened by 26%. And write a compelling subject line to make them want to open the email. My email subject was: Mark, You’re an inspiration to ParentPreneurs.
  2. Include a link to your website or business, so they can check you out if they want to.
  3. And finally, be relevant and get to the point! No one wants to read a novel-length email from a stranger. Or from anyone else, for that matter.

The Interview With Mark
In my email, I asked Mark if I could send him five questions-I wanted him to answer ten but figured I better make my ask something he wouldn’t mind doing, after all, he’s an incredibly busy guy.

Here are my five questions and Mark’s answers, along with a few of my thoughts.

1. I see a lot of gloom and doom on the internet and social media because of COVID-19, do you think this is a good time to start, build, or grow a successful business? If yes, where do you see the best opportunities to do so?

“Best time ever. Most existing businesses are trying to figure out how to bring back their previous businesses. They are not innovating. That is the best time to disrupt any industry or even to start a small business.”

Yep, let’s stop all the doom and gloom thinking and look for opportunities to innovate. General Electric, IBM, Trader Joe’s, and Fed Ex, all great companies that were started during a recession. And we are in a recession.

2. You’ve been hustling since you were a boy selling garbage bags to buy sneakers at age twelve. What do you teach your kids about entrepreneurship?

That in order to get something they want they have to earn it. And since they aren’t old enough for jobs yet, they have to start something they can sell to their friends!

This is brilliant! I was just talking to my seven-year-old twins about starting a business with them and I had no idea what to do. But starting something they can sell to their friends? Brilliant.

3. What’s your favorite book and why?

“The Fountainhead. It fires me up to work harder every time I read it!”

Ok, I was not familiar with this book, but a quick google search shows it was written by Ayn Rand. Here’s the book’s Wikipedia page.

4. What’s the biggest risk you’ve ever taken? How did having kids affect your assessment of risk?

“Good question. Probably leaving Pittsburgh and going to Indiana University site unseen. I waited till after I was financially set before I had kids. I had to wait because I knew I wasn’t good at work-home balance. I was all in on work.”

I can relate to the college decision. I went to Morehouse College from Brooklyn, NY without ever visiting the campus first. And I respect Mark’s self-awareness about knowing how to balance home and work.

5. What’s the best advice you ever received?

Today is the youngest you will ever be. Live like it!

Yeah, carpe diem!

If I were able to ask Mark a few more questions, I would’ve asked him what are his three tips for success in business and what are some feasible side hustles during COVID-19. Thankfully, I found he already answered those questions for someone else!

In this video, Mark’s three tips for business success are:
1. Sales
2. Just do it!
3. Be prepared

As for a practical side hustle during COVID-19, Mark thinks you can make up to $40 per hour doing this:

“I would become an expert in scripting for Alexa and Google Home and Cortana and go to any place that sold devices they supported and show them how much more they could do with a few hours of personalization.”

Read this CNBC article where Mark talks more about AI scripting.

Alright people, now’s the time for all of us to step out of our comfort zones. A comfort zone is a beautiful place, but nothing ever grows there!

So go ahead, shoot your shot. Make that cold phone call, send that cold email, send that LinkedIn connection request (with a personalized note!).

I’m gonna keep taking my shots.

Will you?

P.S., I wanted to use a feature photo that showed Mark as a parent and not him as a business person, but I couldn’t find one with proper usage rights. So I asked him for a family photo and he sent me one. I adore that pic of him and his son at the baseball game. The moral of the story is, simply ask for what you want.

P.P.S., I too am innovating now and starting a foundation to provide $10,000 grants and other resources to help ParentPreneurs be better parents and entrepreneurs. If you’re a parent and entrepreneur visit our landing page to get notified when we launch for a chance to get help.

Feature image credit: Mark Cuban


  • James Oliver, Jr.

    Twin dad, ParentPreneur advocate, Tech entrepreneur

    James Oliver, Jr. is Co-Founder of the world’s cutest twins, Thaddeus and Zoe. James' purpose is to inspire Parentpreneurs around the world to know they can be both a successful entrepreneur and an amazing parent. James is a self-published author of the book The More You Hustle, The Luckier You Get: You CAN Be a Successful Parentpreneur, which is available at amazon.com, and he's a tech entrepreneur at wemontage.com