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Growth Strategies / Partnerships

How a Late-Night Monopoly Game Led to Our Big Deal With Shark Daymond John

You never know when you'll find your next big opportunity.
How a Late-Night Monopoly Game Led to Our Big Deal With Shark Daymond John
Image credit: Maury Phillips | Getty Images
- Guest Writer
Founders of BestSelf.Co
6 min read
Opinions expressed by Entrepreneur contributors are their own.

Sometimes a game-changing business opportunity shows up in the most unexpected place.

At the time, you may be totally unaware of where the door you've opened will lead. You may not feel ready to take the leap of faith that can be required -- especially in the early days of full-on hustle and grind.

Related: Daymond John's Best, Surprising Advice for Entrepreneurs? Get a 9 to 5 Job.

But, our experience shows you've just got to grab those chances when they come. Expect the unexpected. Make the most of the moments and play full-out -- because you never know what will happen next.

For example, one of our most important deals to date took place over a board game!

Here's how it all unfolded ...

Get a seat at the right table.

In just under two years, we've turned a Kickstarter success with the SELF Journal (our flagship planning and productivity tool) into a thriving, eight-figure business. It was thanks, in part, to the relationships we built with our crowdfunding backers and early customers that an opportunity arose to get a seat at the right table.

That's because in 2016 we won the People's Choice Award at Shopify's annual Build a Business Competition. And it was because of our win that we first met Shark Tank judge Daymond John. John was part of the mentoring team for the Shopify winners that year. At a New York retreat, all the winners got to have one-to-one mentoring with some of our business heroes. There was downtime, too, and that's when the board game made an appearance.

Rumor has it that John takes a custom-made Monopoly board everywhere he goes, so when he suggested a game, Cathryn jumped at the chance to join in.

Image credit: Courtesy of Allen Brouwer and Cathryn Lavery


Cathryn remembers it being intense, highly competitive and long! The game extended into the early hours of the morning, but it was during the game that the seeds for an affiliate deal were sown. 

Related: Why Daymond John's 'Overnight Success' Took Years to Accomplish

While playing, Cathryn had the chance to chat informally with John about the SELF Journal and our vision for Best Self. It soon became clear that John loved our product and that there was mutual benefit in John promoting it.

One of the reasons John supported our journal is because it aligns with his own personal philosophy of success. He talks about these principles in his upcoming book, Rise and Grind. John always stresses the importance of waking up, putting your best foot forward and understanding how high-achievers craft systems and process to help them be successful.

John himself is a big believer in crafting success systems and one of his practices is to write down your goals every morning, so he loved that the SELF Journal had these principles baked in.

This is one of the main things we learned from John about affiliate deals. It makes all the difference if you work with people who are super interested in your product because that can pave the way for opportunities that go beyond the initial agreement.

Negotiate deals that benefit all parties.

Over the last year, the affiliate deal has worked brilliantly for us.

John has an audience of entrepreneurs, which is a great fit for our brand. As a result, he's helped us find new customers. He also gave us a high-profile endorsement at a time when the journal was relatively new. Being associated with such a well-known business celebrity was huge for us. It helped to elevate our brand, gained us more credibility quickly and increased the size of the audience who knew about our company.

But, our relationship didn't stop there. Because John loved our product, he got us involved with other opportunities. For example, thanks to John we took part in Miller Lite's #HoldTrue campaign, which gave us more exposure and publicity. He's also helped us widen our circle and network by introducing us to other high-profile business people such as Gary Vaynerchuk.

Related: The 6 Books Shark Tank's Daymond John Wants You to Read

The relationship has brought benefits both ways. When it comes to affiliate deals, we've found the opportunities are magnified and have space to develop when there's a payoff and a benefit for both parties.

We've loved our involvement with supporting John's new coworking space, Blueprint + Co. Based in New York, everyone who signs up gets a bundle of Best Self products to help kickstart their entrepreneurial journey. We've also sponsored some of his events.

Apply John's advice to your business: 

It's crazy to look back and map out all the opportunities that happened just because Cathryn played Monopoly! It was a huge lesson for us. You simply never know what doors will open as a result of the connections you make and the experiences you have. So, just grab those chances when you can and then figure out how you can make them work for everyone involved.

In terms of leveraging affiliates and endorsements, as John advises, find people who love your product. You'll get a much better outcome when you do because it will become more than a cash-generating exercise. Instead, your relationship can morph into one that's mutually beneficial where the opportunities to work together continue to grow.

If you want to scale your business with the help of other brands, the key question to consider is this: Which brand(s) or people could you leverage to help you gain credibility, visibility and new opportunities?

Remember, a bigger business is built on the back of the relationships you make with people. So, have a think about your own business to identify what connections could help you get to the next step.

Related Video: This One Thing Could Have Made Daymond John Even More Successful

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