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Featured Planner: Two Roads Event Co.

Aisle Planner Two Roads Event Co.
Photo courtesy Susan Yee Photography

Over the past couple years, I have had the absolute pleasure of interviewing dozens of wedding professionals. But, I have to say that this one was a bit different – because I think Hailey might be one of my doppelgangers! Not because we look alike but because of her personality (hello my Type A/Type B twin), her story (investing a lot in an education and landing somewhere else), and a shared love of Lucy Lawless.

So today, I am excited to introduce you to Hailey of Two Roads Event Co. Read on to learn about this attorney turned planner, how being simultaneously neurotic and laid back is a thing, and why you should never come between her clients and a contract!


Aisle Planner Two Roads Event Co.Tell us about your path to becoming a wedding planner.

My journey to Two Roads Event Co. has been anything but linear, but then again I’ve always been a strong believer that with patience, hard work and resolute openness, the path reveals itself.

At ten years old following a run-in with Lucy Lawless (Xena Warrior Princess anyone?) where she told me I should be her talent manager (quite seriously, I’m sure), I decided with childlike optimism that I wanted to follow my family into the entertainment industry.

I spent every summer during high school and throughout most of college working in various facets of entertainment, from management firms to agencies, studios to motion picture advertising houses. Fast forward to my sophomore year at UC Davis, and I was studying abroad in Madrid when a girlfriend in LA suggested over Skype that I take the LSAT with her. Once I was back in the states I decided to take the plunge and study for the exam, reasoning that going to law school and understanding contracts would make me a much better advocate for my clients when working with their agents.

I moved from Davis down to Los Angeles to attend Southwestern and, around my second year, four important events occurred that would ultimately shift my path: my mentor passed away, the preeminent management firm I’d built my contacts at tanked, the legal market became heavily saturated making it near-impossible for most of my colleagues to find a job, and I decided that I didn’t want to spend my whole life in Los Angeles (a serious problem for an aspiring talent manager.)

I was feeling a bit lost when a chance meeting at a photo shoot found me chatting with the impressive founding partner of a high profile, predominantly female family law firm. We had a great conversation ending with my offering “if you ever need any help…” and before I knew it I was clerking at her firm.

I felt like I’d found my home amongst powerful, impressive ladies who made men shiver in their Armani suits, and I felt like a rockstar that these women thought I was one of them. When I passed the bar exam and the partners made me an associate attorney, I was overjoyed. The walls of the office were decked in beautiful artwork; I had an assistant at 26, a view of the entire city, and a sizable salary. Life was good.

A few months into my promotion, I realized that something wasn’t right. In fact, it was so wrong that I couldn’t ignore the feeling of dissatisfaction gnawing at my gut every day. I didn’t feel connected to the community of attorneys, despite how impressive they were. No matter how much I worked, no matter how little personal time I had, I never seemed to be working enough– and I found myself pinning the Tom Petty quote “You belong somewhere you feel free” onto the corkboard above my desk without realizing the irony. Most days I wouldn’t see the sun– I’d literally go from my apartment to its underground parking garage, sit in 30 minutes of traffic to drive four miles just to traverse into my office building’s parking garage, take the elevator into my office, work through lunch, and leave with the moon. Never mind that my apartment was huge and on Montana Avenue in Brentwood, or that I was driving a brand new Lexus. The money and the flash and meeting my adolescent picture of success wasn’t sustaining me. I knew that I needed to make a change.

When I finally left the firm and moved up to Sacramento to be with my then-fiancé now husband, away from the beautiful apartment and car and the job I’d worked so hard for, I knew that I needed to make the sacrifice worth it.

So, I got really honest; made myself vulnerable in a way I’d never truly been before. I got out a pad of paper (old school) and wrote down my strengths and my weaknesses. I allowed myself to dream big. I took my time. I wrote down notes about the kind of life I truly wanted to live. I got in touch with my priorities. I got back in touch with myself.

I was as shocked as anyone when I went through my lists, my feelings, and my goals and realized that I wanted to be an event producer. I’d experienced a lifetime of watching my dad, (who was the worldwide head of public relations for the Universal Studios theme park group at the time), throw incredible, large-scale events: the opening party for the Jurassic Park ride where he flew a T-Rex over the 101 Freeway, a birthday party featuring the world’s largest cupcake for King Kong’s birthday, the world’s largest drum roll for the opening of City Walk’s Hard Rock Café. To me, my dad’s job was magical, and I wanted to create that kind of magic in my own career. It terrified me to think that I had no event experience. But I thought– what’s the worst that could happen? And I allowed the answer “you could fail” to drive instead of paralyze me.

A few years ago, after deciding that failure was better than never trying at all, I sat in my pajamas all day like a woman possessed, crafting my business cards, building my website, and designing my logo by hand. I reached out to friends and family until I found a client willing to take a chance on me. I met with hundreds of vendors for coffee dates, and realized pretty quickly that I’d finally found in the creative event community what I was lacking in the legal community. THIS was my tribe. My place. These people were worth leaving behind my past life and moving forward into the unknown for. And they inspired me to build a career that worked for me as much as I worked for it.

As I’ve gained tremendous experience, more confidence, and found my identity as a designer I’ve begun to attract the types of clients, creatives, and opportunities that excite me and fuel my innovation more and more. And perhaps most importantly, I’ve found the resolve to continuously embrace the path I’m on. I think it’s really important to be brave when you’re an entrepreneur. There are a lot of roadblocks, a lot of missteps, and you get the door slammed in your face sometimes. The word “passion” gets thrown around a lot… but in my opinion, being brave is just as crucial. You’ve got to roll with the punches.

Aisle Planner Two Roads Event Co.
Photo courtesy Susan Yee Photography

You took the time to fine tune your planning skills by attending Bash Please’s Wed Prep years ago. What did you learn that still resonates with you today?

That relationships are everything.

We found out that you are an attorney (!). How does that influence your approach to running a business and working with clients?

My legal education and experience has practical value in that I draft my own contracts, negotiate on behalf of my clients, and ensure that their contracts with other professionals are sound. But perhaps the greatest value in hiring someone who is a unique combination of attorney and event producer is that you get the whole “right brain / left-brain” thing. I’m an easy going, creative “type B” and a neurotic, detail-oriented “type A” all at once– and it’s absolutely perfect for this job. I like being my clients’ advocate. I like that being an attorney has taught me to see both sides of an argument. Finding the gray is really important, even if it’s just the argument for whether to go with a velvet runner from La Tavola, or a gauzy plant-dyed one from Silk & Willow.  In all seriousness though, problem solving is huge.

Favorite fall palette?

Mustard, Navy and White (with tons of greenery!)

How do you spend the morning after an event?

Sleeping in with my chiweenie Shirley and my husband Adam. Then brunch with lavender mimosas, preferably followed by a foot massage. Everything hurts the morning after a wedding!

Where did the name “Two Roads Event Co.” come from?

My irritatingly creative father.  After debating on a business name for weeks, I called my dad and he came up with it instantly. (Of course.) It’s a beautiful allusion to my experience in choosing event production as my “second road.” It’s also about what we want in our clients. We want clients that take the road less traveled– clients who really know themselves and want to create something bigger and more interesting than “an event.” Symbolically, two roads coming together is love. Two roads separating is creativity. Choices.

The types of creative projects and events that you work on is wide ranging. What do you love doing the most and what do you hope to book more of?

I’ve always been drawn to narratives and storytelling – whether for a brand or a bride. This season we were fortunate enough to design a Wes Anderson’s “Moonrise Kingdom”- glamping-inspired event for Sunset Magazine in Napa. It was a high note. And we worked on the 2017 Emmy’s this past week (no big deal right?)

But I have to say (for the most part), weddings are my jam. I love learning about what makes my clients tick. About their favorites, their memories, the little things that make them who they are, what they love about each other. Crafting experiences and honing an aesthetic that tells that story is such a high. I’d love to continue booking clients and projects that care about digging deeper and really saying something with the way their events are constructed- I value bravery in design, yet find immense beauty in simplicity.

We love your video portfolio! Knowing you love storytelling, do you often get to be involved in the video production process?

I’m flattered. We direct our cinematic partners to the various vignettes and moments we’ve crafted, but we feel strongly in the importance of each individual talent having the freedom to create their art the way they see fit. Though being part of the video production process sounds really fun!

Aisle Planner Two Roads Event Co.
Photo courtesy Margaret Austin Photography

Do you remember how you found out about Aisle Planner?

Honestly I don’t– but I will say that discovering Aisle Planner has been a game changer.

Since you have a legal background, do you have any thoughts on why it is important for wedding professionals to use our new Proposal and Contract feature?

In my view, having professional, clean and automated proposals is incredibly important. It lessens or eliminates friction in the signing process and allows you to put your best foot forward with a potential client during a crucial juncture in the process.

How would you describe your style?

Organic. Romantic. Clean. Innovative. Magical.

What are your goals for closing out the year and what do you hope to accomplish next wedding season?

My goal is to make sure that we execute amazing events for our remaining 2017 clients. We’re lucky to be producing events all over California in the coming months.

This week marks the beginning of our annual “explore to create” period, where we travel abroad to gain inspiration for our designs and meet with event industry professionals in other parts of the world. Iceland, Germany, Austria, Italy and Sweden are on the itinerary, with a particularly interesting project in Venice. Next year, I hope to push myself and my team to continue delivering rad designs and seamless event execution for our clients, to gain more design inspiration during our 2018 trip to Bali, and to absolutely slay our first International wedding in Whistler, Canada.

Want to see more from Hailey? Check out her website tworoadseventco.com

About the Author

Tayler Cusick Hollman
Tayler Cusick Hollman

Tayler is the Creative & Marketing Director at Aisle Planner. She is obsessed with color and pattern, notoriously cooks everything from scratch, and can sometimes be seen cruising around on a skateboard. Follow Tayler on Instagram @taylrd_designs

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