Ep. 027 Scott Dunn: Dominating the World of Entertainment Tourism

Scott Dunn Transformation Blueprint Paul Stennett Dream Weekend

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If you have a great corporate job, and you’re on an upward path, making excellent money, would you leave it all and risk getting nothing? Scott Dunn’s “dream” was too big to ignore, and he’s getting paid massive dividends for jumping off into the deep end.

Scott is the Managing Director of Dream Entertainment, masterminds behind the renowned Dream Weekend event, Xodus Carnival Band, stalwart parties like Twisted Spiritz, Yush, Daydreams and tons more to mention.

In this episode, he shares how a business thrived in a non-traditional business industry as entertainment and grew to contribute billions of dollars per year to the Jamaican economy. Scott is 41 and lives in Jamaica with his wife and 2 daughters.

We also talk about:

  • Finding your unfair advantage and leaving your competition in the dust,
  • The biggest and most overlooked asset young entrepreneurs need,
  • How to keep up with the huge scale of your vision,
  • And so much more!


  1. Build around what you’re good at and enjoy. Very often I hear people say they have no idea what business they would start, when the idea could be sitting right in front of you. Scott was naturally into bringing people together and entertaining since he was in school, and he naturally maintained that interest throughout his life. So, the idea for Dream Entertainment was a culmination of all the time he spent doing what he loved and was naturally good at. If you’re thinking of a new business idea, make a list of the things you love to do, and a list of the things you’re good at. Are there similar line items on both lists? If so, you’re onto something.
  2. Find your unfair advantage. Here’s a huge reality in business: you’re going to have competition. If you’re a big player in your field, you’ll have targets on your backs from smaller players dreaming of taking you down. If you’re smaller, you’re taking aspects of what other companies aren’t doing and carving your differentiator. In order to fend off the competition, you need to rig the game in your favour. For Scott and his company, they execute much harder than a company of their size normally would. Meaning part-time event promoters and newcomers to the space just can’t keep up. How do you find your unfair advantage? Evaluate your customer experience, your production process or the negatives of your industry that everyone is ignoring.
  3. No risk, no reward. Scott made a jump to his business full-time at a period when others might have resisted or been terrified to do that. He was on track for huge promotions and paydays, he was the breadwinner of the family and had a young child. All the modern advice would have said that’s an unwise decision. But it paid off big. Each person has their own risk tolerance, assess yours. But ensure you’re involving the future in your assessment. 5, 10, 15 years working in your job versus the same time growing your business and living life on your terms. To most people who became entrepreneurs, the choice was clear.
  4. Credibility is the real king. When Scott started Dream Entertainment with his partners, they already had a lot of credibility built up from successful parties in the past. So, when they started hosting larger events sponsors and suppliers were happy to come along for the ride and bring even more favourable terms. Before you approach your market, sponsors or suppliers, ask yourself, “what credibility do I have in the market?” If you don’t have any, start small and build up. Maybe offer your service discounted or for free in exchange for testimonials. Or make it a no-brainer for people to do business with you by using aggressive satisfaction/money-back guarantees.
  5. Suspend all your expectations at the start. At the start of your entrepreneurial journey, very little will go according to plan. Think about a baby, they stumble and fall several times before they learn to walk. Do not expect that your launch will be amazing, and you’ll hit all your success target in your first year. Plan for success, work towards it, believe in it, but don’t create any unrealistic expectations around it. Scott’s first event was going to be a success with all the planning that went into it, but he lost all his money when rain had a different plan for his expectations.
  6. Show up with a plan. It is a super important Scott made about sponsors looking for a return on investment. Let’s look deeper at that. This goes beyond an entertainment business and covers sales and customer acquisition in general. Determine what the customer’s wants and needs are before you approach them. Too often, amateur and beginner business people show up with a product they’ve developed and try to sell it without understanding the customer. Flip that on its head and determine what their KPIs are, what ROI is important to them, what pains and problems keep them up at night. DO that and you’re well on your way to a thriving business.
  7. Choose long-term collaboration over short-term revenue. Scott mentioned in this episode that he works with sponsors as a means to add more value to the partygoers. That’s genius. When the patrons feel they are getting more value, they’re willing to pay more. And when they pay more, well, that has a ton of knock-on effects. The patrons actually show up excited, the promoters benefit, the sponsors get the brand awareness and association with a successful event. If Scott was only looking at “how can I make the most money from this sponsor” those benefits and this genius path might’ve been overlooked. If you want to gain more revenue, grow more followers or influence, align your intent with collaboration and find people who’re going in your direction or stand to benefit equally – or even more than you will – from the collaboration.



Scott’s Instagram – https://www.instagram.com/dunnscott

Dream Weekend Website – https://jamaicadreamweekend.com/jm
Dream Entertainment Instagram – https://www.instagram.com/dreameventsja

Xodus Carnival Website – https://xoduscarnival.com
Xodus Carnival Instagram – https://www.instagram.com/xoduscarnival

Dream Weekend Cruise Website – http://dreamweekendcruise.com
Dream Weekend Cruise Instagram – https://www.instagram.com/dreamweekendcruise

Enjoy the episode and thanks for listening!


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