The Wedding Biz – Episode 421 STEPHANIE COLE: Making Big Changes and Going Solo

 In All Network Episodes, Events, The Wedding Biz

Andy welcomes Stephanie Cole of Cole Drake Events to the podcast today! Stephanie is the founder and principal planner of Cole Drake Events, a luxury destination wedding planning company. They have been featured in Martha Stewart, Harper’s Bazaar, and the New York Times. Stephanie and Andy talk about Stephanie’s early influences, how she made the transition from having a business partner to running her business by herself, what her process tends to look like with clients, and what kinds of challenges she has faced and how she overcame them. She also shares an interesting story about her favorite wedding, discusses her pricing philosophy, and more.

Stephanie identifies what her personal signature is, revealing how detail-oriented she is. She also reveals that one of the most difficult aspects of her job is having to say goodbye to some of her clients. Andy had such a great time interviewing Stephanie and especially enjoyed getting such a great snapshot of her business. He would appreciate it if you would share this interview with a few people you know who might also enjoy it! Andy would also really appreciate it if you were to subscribe to the podcast if you aren’t already and to leave a top review wherever you listen! That really helps out the show and helps people find it!

Have you heard about Stop and Smell the Roses with Preston Bailey on The Wedding Biz Network? Listen as Preston shares the secrets, tools, and technologies behind his extraordinary ability to create a theatrical environment out of any space. Also, don’t forget about Sean Low’s podcast The Business of Being Creative, where Sean discusses the power of being niched, pricing strategies, metrics of success, and so much more. You can find both shows on The Wedding Biz Network.


Become a patron and support Andy and the show! If you are so inspired, contribute!

Time Stamps

[1:19] – Andy reveals today’s guest as Stephanie Cole of Cole Drake Events!

[2:28] – Stephanie talks about her mother being an inspiration to her.

[5:48] – Stephanie reflects on when she started Cole Drake Events.

[6:21] – Stephanie reveals what it was like to make the jump to entrepreneurship.

[7:09] – Learn about how Stephanie used to have a partner in the business.

[9:37] – Andy talks about how he started solo and then brought on a business partner.

[11:35] – Stephanie identifies her personal style.

[14:58] – Andy directs the conversation toward Stephanie’s process with her clients.

[17:31] – Stephanie gives an example of a process with a client.

[20:00] – Discover what the hardest part of Stephanie’s job is.

[22:23] – Stephanie shares a story with us of a challenge that she had to overcome.

[24:59] – Stephanie provides an example of one of her favorite weddings that she has done.

[27:11] – Hear Stephanie talk about her pricing philosophy.

[29:20] – Stephanie touches upon how she differentiates herself in the industry.

[31:55] – Andy announces where we can find Stephanie online.



The New York Times – “In Napa Valley, a Commitment to One Another, and to Showcasing Diversity”

Martha Stewart – “A Plant-Filled Indian Wedding in Sonoma, California”

Harper’s Bazaar – “The Top 23 Places for a Destination Wedding – According to the Experts”


Find Stephanie:

Cole Drake Events – Website
Cole Drake Events – Instagram Page
Cole Drake Events – Facebook Page
Cole Drake Events – TikTok Page
Cole Drake Events – Pinterest Page

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Title Sponsor: This episode is sponsored by Kushner Entertainment.

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