Returning to the podcast this week is none other than Jennifer Stein, editor-in-chief, publisher, and co-owner of Destination I Do Magazine, a magazine that can be found online and on newsstands.

Jennifer joins Andy today to explore the journey of building a renowned brand in the destination wedding industry, sharing how she and her business partner started Destination I Do twenty years ago to fill a gap in the wedding industry by showcasing real couples celebrating their destination weddings worldwide. From humble beginnings with an amateurish first issue to becoming sought-after across various platforms, Jennifer reveals the challenges they faced, including financial struggles and burnout. Despite setbacks, they persevered, eventually turning a profit after three years of hard work and reinvestment.

She also discusses their staffing approach, emphasizing flexibility with independent contractors and prioritizing long-term relationships. She shares insights into their decision not to use virtual assistants and how they adapted during the pandemic by listening to clients’ needs and offering tailored solutions. With destination weddings making a strong comeback post-pandemic, Jennifer reflects on the industry’s resilience and the evolving trends that she is observing.

Throughout the interview, Jennifer’s passion for storytelling and commitment to serving her clients shine through, highlighting the invaluable lessons learned over two decades in the business. Andy had such a great time having her back on the show, especially since he feels that their conversations together are always especially animated and electric!

If you enjoy this conversation with Jennifer Stein, then please don’t keep it to yourself! Share it with a few good friends and industry colleagues who might also enjoy it! Andy would also appreciate it if you were to leave a top review wherever you listen to the show because that really helps the show out! Lastly, don’t forget to follow The Wedding Biz on Instagram and subscribe to the podcast so that you never miss a new episode when it drops!

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.



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Time Stamps

[0:00] – This is episode 500, and Andy expresses gratitude for all of his loyal listeners!

[0:51] – Today’s guest is returning guest Jennifer Stein of Destination I Do!

[2:44] – Launching Destination I Do filled a gap for couples seeking more than tropical destinations.

[4:23] – How long was it before Jennifer turned a profit?

[5:55] – Jennifer touches upon how initial setbacks led to learning from mistakes, paving the way for eventual success and growth.

[8:06] – Jennifer reveals how limited resources led to self-financing without investors or loans, navigating challenges like the mortgage crisis.

[10:38] – Flexible staffing, Jennifer explains, includes hiring contractors for roles like sales, creating long-term mutual relationships.

[13:08] – Hear why Jennifer prefers not to use virtual assistants.

[15:24] – Jennifer nearly sold her business three times, prioritizing buyers who understand the wedding industry intricacies.

[16:34] – Despite setbacks and burnout, Jennifer avoided selling her company, realizing buyers misunderstood her situation and intentions.

[19:31] – Jennifer’s realization in 2020 prompted her to pay herself what she’s worth.

[20:53] – Andy reflects on a time when he felt burnt out and found relief by getting a business partner, re-energizing him for success.

[23:33] – Amid the 2020 pandemic, Jennifer prioritized client needs, offering assets and support and fostering valuable partnerships.

[26:05] – Jennifer shares how she and Harmony Walton revamped projects, enhancing storytelling and revenue.

[28:57] – Jennifer, a Gen Xer, learned that success isn’t instant, facing setbacks but finding joy in victories.

[31:09] – Jennifer strongly feels that destination weddings are back with a vengeance!

[32:27] – Learn from Andy where Destination I Do can be found online.



Jennifer’s Previous Guest Spots on The Wedding Biz

Harmony Walton’s Previous Guest Spots on The Wedding Biz


Find Jennifer:


Destination I Do – Website


Destination I Do – Blog

Destination I Do – Podcast

Destination I Do – Facebook Page

Destination I Do – Instagram Page

Destination I Do – Twitter Page

Destination I Do – Pinterest Page

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Title Sponsor: This episode is sponsored by Kushner Entertainment.