Meet Jennifer Craycraft | Entreprenuer

We had the good fortune of connecting with Jennifer Craycraft and we’ve shared our conversation below.

Hi Jennifer, how did you come up with the idea for your business?
This is a fun one! If you were to tell me ten years ago where my life was at today, I wouldn’t have believed you. I didn’t think I would be doing something that I absolutely love and that is so not the norm. I started out in the medical field as a nurse in the hospital working long hours and just beginning a family. After about 10 years of working, I was diagnosed with an illness that required life-long treatment and for me to step away from nursing. I went through an immense funk, but fortunately, I have an amazingly supportive husband who helped me get through that dark period. One day while receiving treatment, I decided that I needed to do something that brought life back into me, and that is when The Tiny Umbrella was born. (I have always had a love for all things tropical and my dream destinations are always somewhere sandy with umbrella drinks.)
I first started my company with Instagram and would travel around ordering rum drinks like a pirate and posting the beautiful concoctions from all over for followers to see. After so many umbrella drinks I noticed one thing that was in common with all of them, they all looked so similar. They all had those same old flimsy umbrellas.
Everywhere I went, the drinks were amazing, but the same old boring umbrella. Now you may ask yourself, “So? who cares?” Well, you didn’t know you needed a new umbrella design until you met me! I spent about 6 months researching the design and manufacturing of umbrellas and finally found a manufacturer willing to work with me and make my own designs into retail packages. I have a background in art when I was younger, so this really allowed me to use those skills in making my umbrellas. I started with 10 unique designs, received my first samples, started my website and off I went. Four years later, I now have over 50+ designs, have sold to every state in the US and more than 30 countries. I wholesale my umbrellas to retail shops, restaurants, bars and markets and are in over 150 stores and counting. Recently I have added laser-cut items such as stir sticks and garnish picks which really opened up the market for me.
This company brings me (and others) so much joy. I absolutely LOVE when people send me photos from their events like a wedding, birthday or baby shower and I get to see my products out in the world putting smiles on people’s faces. That right there is why I do it and what got me out of that funk and into something I love.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
It hasn’t always been smooth that’s for sure. Try telling someone you make cocktail umbrellas for a living and see their reaction-they tend to be confused. At the beginning, not many people took me seriously going from the medical/nursing field to starting my own company with no business background. I think it was tough for people to view me as a businesswoman at first and a bit challenging in getting started. I had to overcome so many negative remarks thinking it was my “hobby” or “little business” that it actually fueled my fire to do more and go farther and prove them all wrong. I also was kind of a first in the industry, bringing essentially something new and fresh to the restaurant and cocktail industry. This took some time for people to get on board, but now it has taken off! Getting my products in stores was the ultimate milestone of my business, and that has definitely made me feel accomplished. It is a shining moment when I can see my product in a retail store on the shelf, or used at one of my favorite restaurants!

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Orange County has so many fun options to choose from! I love to bring out of town friends to my favorite food spots and the beach! I love to grab coffee at Coffee Dose in Costa Mesa and Lolas Cafe in Ladera Ranch, sometimes I’ll hit up Urth Cafe in Laguna. The beaches in Laguna, Dana Point and Newport are always a hit, and staying for sunsets is magical. I love to head over to Balboa Island and walk along the shops and boardwalk. We can’t leave without hitting up the Dad’s Donuts for a frozen banana and going to Balboa Candy for our sugar fix! I always love to bring guests across the Balboa ferry to the Fun Zone peninsula and then rent beach cruisers and head to the pier. We always make sure to check out Dory Deli for some amazing sandwiches, or Ruby’s on the pier for that quintessential SoCal experience.
Orange county has so many great restaurant options to choose from that I think I would suggest some fun “experiences” in South OC for guests. The Tea House on Los Rios gives the best High Tea experience in San Juan Capistrano and is very Instagram worthy. Nearby is Trevors on the Tracks where you can dine literally next to the tracks and watch the train cars go right next to you window. El Adobe, also in San Juan, is a local Mexican restaurant and landmark near the Mission and used to be the old Mission jail house. You can request to dine in their one last remaining original jail cell that is slightly underground and has markings on the walls from its old occupants.
It wouldn’t be a proper Tiny Umbrella visit without taking friends to the newly reopened Royal Hawaiian in Laguna. It’s the perfect way to end a night with the best Mai Tais and coconut shrimp!

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
My first and foremost most supportive person would be my husband Brian. I would not be where I am today in life and business without him. He, from day one supported my adventure and transition from healthcare to business owner and always gave me sound advice and never ending support. My daughter Cameron was also right there with him cheering me on, helping me with concepts and designs and the occasional order fulfilling. I have the BEST friend group that has supported me since day one as well. They gave me their ear when I needed it, cheered me on when I was down, and always were great fun to test out some fun drinks with!
My company would not be where it is now without the amazing support of Anne and Joel Tanner at Tikiland Trading Company. I started out as a newbie in the “tiki community” and they welcomed me and my umbrellas with open arms. Never ones to gatekeep helpful information, and always so supportive of small business and artists, I am truly thankful for them!

Website: www.thetinyumbrella.com

Instagram: @the_tiny_umbrella

Other: Faire Wholesale https://faire.com/direct/thetinyumbrella

Image Credits
Photos by myself, Jennifer Craycraft Michael Agudelo Two colorful drink photos with tropical umbrellas