We caught up with the brilliant and insightful Stephanie Bosdosh a few weeks ago and have shared our conversation below.
Stephanie, thanks for taking the time to share your stories with us today What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?
Starting my own company was initially daunting for me. With no prior business background aside from what my father had established over years in the golf industry, it was a challenging leap. In my previous experiences with event jobs, I often felt my voice and ideas were stifled, bound by strict protocols that was predominately in workplace with all men.
However, I knew I had the potential to create something profoundly successful if I could muster the courage to overcome my fear of making mistakes. Inspired by my parents’ success with their Golf Academy, I began by becoming a Venue Coordinator at a local winery to understand wedding planning better.
I gradually expanded my skills by working as a baker, florist, bartender, and event manager (a role I had previous experience in, organizing golf tournaments across the US). I believed that comprehending all facets of weddings would lay a strong foundation for my business.
Despite knowing there would be inevitable mistakes and setbacks along the way, I chose to show myself grace and persevere. I pushed through all my doubts and overcame my fears to take the leap.
With determination and by the grace of God, I launched my business. It took off unexpectedly, and I now lead a team of five dedicated wedding employees.

Stephanie, 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?
My journey into the wedding world was anything but ordinary! Picture this: I grew up in a lively crew of six, with parents who drummed into us the importance of love and quality time with the ones you hold dear. As a high achiever rocking it in both academics and sports (hello, golf!), I was homeschooled by my parents until college.
Being cooped up together so much, I got a ringside view of the real deal on love and genuine compassion. It hit me—I wanted to dive into an industry that brings people together, surrounded by pure joy and love. That’s when the wacky notion of becoming a wedding planner first danced through my head as a kiddo. I used to call it my dream job, but honestly, I never thought it could happen! Life’s funny that way, huh?
The excitement of being a wedding planner intensified as I grew older, fueled by the excitement of watching iconic movies like “27 Dresses,” “The Wedding Planner,” and “Father of the Bride.” One defining day, while on a break from school and wandering through DC, I witnessed a wedding planner orchestrating a traffic-stopping moment to capture the perfect shot of a beautiful bride and groom. Right then and there, I knew I wanted to find a way to make my “dream job” into a reality.
My journey into event planning kicked off in the golf industry, where I taught golf alongside my father, a distinguished Top 100 Golf instructor for the PGA. Through my work, I found myself connected with the United States Golf Association and the Hurricane Junior Golf Tour, organizing and directing golf tournaments that brought together over 300 junior participants. I felt this was the end of my journey in planning because I knew what I was doing was still helping people and finding ways to show a genuine connection with each junior I came across.
Come 2019, I took a leap of faith, diving into the world of wedding planning. I began shadowing any wedding planner willing to impart their wisdom, spanning areas from Baltimore to DC and Frederick. Soon, I found myself as a venue coordinator, and it dawned on me—I was on the verge of turning my dream job into my own business.
And just like that, WedWithSteph came to life, with me starting from the ground up, accepting any opportunity that came my way. As my business grew, so did the praises on Facebook and Google reviews. Now, I am fortunate to have a team of five incredible employees, each with diverse backgrounds in florals, catering, interior design, food and beverage, and planning.
I’m passionate about creating an environment where couples can trust and let go on their big day. WedWithSteph is more than just a business; it’s a celebration of love and a testament to turning dreams into a magical experience.

We’d love to hear the story of how you built up your social media audience?
Building my social media audience initially posed challenges because potential clients often rely on reviews to gauge trust and comfort when hiring a wedding planner. However, I remained steadfast in my commitment to authenticity and my business model.
I prioritized building genuine relationships with my clients, treating them like friends whom I genuinely cared about and wanted to know on a personal level. This approach extended to every wedding I coordinated, creating an atmosphere true to my values.
By staying true to myself and providing exceptional service, I earned honest and trustworthy reviews from satisfied clients. This approach has proven invaluable in building my reputation and attracting clients who resonate with my approach and values.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
One thing I had to unlearn and approach differently was my mindset from teaching golf swings, where adjusting one aspect reliably produces a predictable outcome in the shot and ball flight. In wedding planning, however, making changes doesn’t guarantee the desired outcome.
I’ve learned the importance of preparing multiple plans and backups for potential issues, as outcomes can vary unexpectedly. By meticulously planning and having contingencies in place, I can better manage and mitigate adverse outcomes or unexpected challenges.
Contact Info:
- Website: https://sites.google.com/view/wedwithsteph/home
- Instagram: WedWithSteph
- Facebook: WedWithSteph

Image Credits
Alice Tran
Taylor Webster
Maura Pierce

