We recently connected with Jennifer Stein and have shared our conversation below.

Hi Jennifer, thanks for joining us today. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

In the 18 years I’ve been a business owner I cannot tell you the number of times I’ve wanted to sell the business or just give up and go work for someone else. Each time it’s happened there’s been one thing in common – burn out.

The last time I felt this way was during the pandemic. We had lost more than half of our contracts and were looking at how we could keep the business going with very little money coming in and more money going out. Lucky for us, we’ve been a cash-operated business from the beginning so we had no debt and had money in the bank before everything shut down. Even with that, things looked very bleak. I had to lay off a few key people which resulted in their work getting piled onto my plate. I was emotionally and mentally exhausted by trying keep the business going, motivate the employees I had left and do all the other things the pandemic heaped on people (homeschooling my elementary aged kids, being locked down when I usually travel and have face time with clients and colleagues, not getting to see loved ones and many other things).

At one point I was certain we weren’t going to be able to sustain. It felt as if we were dying a slow death. I met with one of my employees to tell her she may need to dust off her resume but that I would do anything and everything to help her find another job and she looked me dead in the eye and said, “I don’t care if this is the Titanic, I’m going down with the ship.”

I knew right then and there that we would be okay. Here I had an employee who had faith in me as her leader and who was passionate about our business. Those two things pulled me out of that burn out phase I was in and helped me see that we could do it. And I’m happy to report we’re still here and better than ever.

Jennifer, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

For those who don’t know me, in 2004 I started Destination I Do – a media outlet devoted to the engaged destination wedding couple.

When I started the company, we were working out of a bedroom and had just two people who worked on everything. From sales and the website to writing and creating content – we were so green.

As time went on, we learned every lesson the hard way but because we were fearless and had very little to lose (except my lifesavings – but I was 28 at the time, so it wasn’t much lol!).

Now Destination I Do is a recognized brand by engaged couples, venues, wedding planners, visitors bureaus, conferences and wedding vendors around the world. We went from a small publication and website to an internationally known media outlet with a large following. We’ve worked with some of the best wedding professionals in the world and have showcased some of the most stunning weddings.

In 2022 I now host the Destination I Do podcast which is in its third season and we have added a consulting portion of the business where we help hotels, resorts and venues with their content creation – from website copy and social media content to photos and videos that will help them sell to the very couples they’re trying to target.

Can you talk to us about how your funded your business?

When we first started Destination I Do over 18 years ago, we thought we’d be millionaires overnight. My business partner is my mom and when we came up with our initial investment it was pretty naive.

We decided at the very start that we wouldn’t take out a loan or bring on an investor because we didn’t want to be beholden to anyone. I’d just left a corporate job and the idea of being under someone’s thumb financially made it feel as if I was just working for someone else again. So we have been cash operated since the start.

Lucky for us, I happened to be fairly good at sales and we boot-strapped our costs as much as possible. So within 2 years we were breaking even.The entire time we’ve owned the business, we’ve never been tempted to overspend. We do an annual examination of what we’re spending – including subscriptions to different things. It’s amazing how just a few extra line items can add up so quickly.

Because of this mind-set of not getting into debt or overspending, it’s allowed us to persevere in some of the hardest economic downturns I’ve seen.

How’d you build such a strong reputation within your market?

Reputation is very important in the wedding and travel industries. I believe people know me to be honest, hard working, kind and inclusive. They know that I can be trusted and although I have very close friends in my industry, I’m not someone who will exclude you if you’re by yourself at a networking event.

My clients are treated like gold. It doesn’t matter if they have the smallest budget or the largest with us, they will be treated as a valuable partner from the start. If something isn’t working, we work with them to change it so it will work.

We have clients that have been with us since the first issue and they feel as if they have a home with us. The employee turn over at our company is insanely low. We’ve had people who have worked with us from our very first hire and most of our interns get some kind of job with us or we’ll help them find one through our connections. I invest in people with my time and energy regardless if it’s a freelance writer, a sales person, a photographer submitting a wedding or someone I just met at a conference. The entire reason I’m in this business and love it like I do is because of the people side of things. I love media and what we feature (I mean, who doesn’t love gorgeous destination weddings???) but the soul of my business is all about the people.

Contact Info:

• Website: https://destinationido.com/
• Instagram: https://www.instagram.com/destinationido/
• Facebook: https://www.facebook.com/destinationidomag
• Linkedin: https://www.linkedin.com/in/jennifer-stein-2750578/
• Twitter: https://twitter.com/DestinationIDo
• Youtube: https://www.youtube.com/channel/UCWBs5l4izNtMGlzj1wiBNMQ

Image Credits
Dennis Kwan, Valorie Darling, Jenni Summer Studios