Tyler Kupper is a business development executive across sports, media and start-up platforms. He has a proven track record of closing major partnership deals and quarterbacking full-consumer, B2B and small business activation plans. He played Division I college golf and is a 4-time golf club champion.

Tyler Kupper


I’ve always been an entrepreneur.  At age 12, I started a party help company, assisting in any/all tasks at Connecticut dinner parties from cooking to cleaning to valet parking!  In college, as President of the Student Athlete Government at the University of Delaware, I started a charity event called the Pigskin Pass, supporting Special Olympics that has raised $250,000 in 8 years and impacted the lives of thousands of athletes. After graduation upon moving to New York City, I was struggling financially living in Manhattan with my first low paying sports marketing job and decided to start a side business, an on-demand Christmas Tree delivery company called Tyler’s Trees which I sold in 2016.

Tyler’s Trees led to meeting Rick Reichmuth, Chief Meteorologist of Fox News Channel when my tree company was doing a segment on Fox & Friends which Rick co-hosts on the weekends.

Rick and I stayed in touch and about three years ago Rick called me to help him craft the business plan and strategy for this umbrella concept he had been working on for a few years.  Fast forward, I left my Senior level position at USA TODAY Sports / Gannett and went full-time with Weatherman in August 2017 three months before we launched the brand.



You wake up in the morning — what’s the driving passion?

To make a difference.


What was the genesis for the Weatherman?

After years in the field and being in crazy weather situation, Rick could never find an umbrella that could withstand these conditions. Leveraging his meteorology expertise and career covering severe weather, Weatherman was born!


How long was the process from prototypes to finished product?

The process covered about 5 years!  Rick would take apart thousands of umbrellas in his Brooklyn apartment finding what makes the perfect umbrella. When I joined in 2016, we were able to design the golf umbrella collection with my input as former scratch amateur competitor and playing in crazy weather conditions everywhere from the 2002 U.S. Junior Amateur Championship in Atlanta to the World Father Son Golf Tournament in Ireland!

2018 Ryder Cup umbrella design

What separates what Weatherman provides versus your competition?

Product quality and the experience of opening up a Weatherman — packaging, tracker chip, welcome guide, etc. Weatherman truly represents the convergence of technology, engineering and design — not to mention our Bluetooth tracking device that allows you to locate your umbrella where you misplaced it and the IOS/Android Weatherman App notifies you on days you need to bring it with you based on the weather. The golf collection also includes two patent pending features: A mesh pocket inside the canopy of the umbrella for your glove or scorecard and a silicone coated rib so your towel doesn’t slide off and onto the wet ground as well as the highest level of UV protection (UPF 50+).

We believe product quality is why the PGA of America selected Weatherman as the Supplier for the 2018 U.S. Ryder Cup Team and Golf Digest named Weatherman “Best Umbrella” the past two years in their annual Editor’s Choice awards.


Many companies routinely tout customer service. Define the term and the approach Weatherman follows?

As a primarily direct to consumer business model, Weatherman has been able to control the customer experience to ensure everyone has an incredible purchase process but more importantly can proudly take their Weatherman outside in any conditions. What this has done has turned our customers into advocates allowing for rapid growth and brand awareness.

2018 PGA Show set-up : activation

Is the golf market your primary area of emphasis?

While Weatherman’s golf SKUs are not the majority of Weatherman’s sales, they have been a critical part to the early success of Weatherman. We decided to create two sizes of golf umbrellas, 62” and 68”.  We felt like the 68” TOUR size is too big for most amateur golfers so we developed the 62” model which has been selling great and is even the choice of both the 2019 United States and European Solheim Cup Teams coming up in Scotland.


In approximate percentage terms — your sales emphasis in the areas of brick and mortar retail outlets, green grass shops and online?

Our sales are nearly 100% online from our website. We are in a select few Top 100 green grass shops as well as gifting for PGA TOUR and LPGA pro-am events but don’t use sales reps, all from the relationships from across our team.

If you could change one thing in golf unilaterally — what would it be and why? 

Access. Golf needs to be more accessible, not just in terms of public vs. private courses but all-encompassing from the cost of greens fees to affording the latest driver. Golf needs more 3-hole loops and TopGolf’s in this 24/7 connected world.


Biggest short and long term challenges facing Weatherman?

Short term is launching our mini/travel size umbrella later this year which is our first new product since launching the golf line at the 2018 PGA Show. The long terms is navigating international expansion and retail

Best advice you ever received — what was it and who from?

From Barry Hyde (EVP, Wasserman Media Group and former USGA CMO): “If there is an issue and you don’t tell me about it, you have a problem.  If you tell me, it is our challenge.”



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