BOSS WOMAN: HAILEY ERIN SILVER

Name: Hailey Erin Silver

Title: Destination wedding stylist, owner of event production and design studio Two Roads Event Co., and co-founder of Northern California’s premier event design showcase FRESHbash

1. What is your business and what do you do?

My business is Two Roads Event Company. We’re event designers, producers, and storytellers who travel worldwide in search of the most beautiful people, the most innovative brands, and the most breathtaking spaces. We cherish tradition, but we’re not overly concerned with doing things the way they’ve always been done. We’re interested in the road less traveled, YOUR road, creating a design that makes your heart beat faster, crafting a moment that brings tears to your eyes. Our specialty is producing events in a way that emphasizes the journey, with a creative, collaborative approach to planning and a narrative-based approach to design. Our goal is to learn about who our clients are and what they love, and showcase their story in ways that are personal, evocative, and unforgettable.

Image by Evynn LeValley. Event Design: Two Roads Event Co. Florals by Burst + Bloom.

2. What is your entrepreneurial journey, how did you become a boss woman?

“The path will reveal itself” has been a mainstay in my life because it’s always been true, and if I’m a boss woman today, it’s because I’ve been tirelessly open. Open to new people, new places, and new possibilities. Perhaps most importantly, I’ve been open to failing.

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 2L 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 photoshoot 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, and 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.

Image by Evynn LeValley. Event Design: Two Roads Event Co. Florals by Burst + Bloom. Catering A Taste of Elegance

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), 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.

IMAGE BY EVYNN LEVALLEY. EVENT DESIGN: TWO ROADS EVENT CO. FLORALS BY BURST + BLOOM. GOWN VERA WANG.

IMAGE BY EVYNN LEVALLEY. EVENT DESIGN: TWO ROADS EVENT CO. FLORALS BY BURST + BLOOM. GOWN VERA WANG.

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 lovely 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.

3. What is the hardest part about running your business and how have you learned to deal with it?

Achieving balance. It’s always the struggle. I’ve learned that you can have boundaries and still be generous. You can draw a line and still give people what they need. It’s something I’ve worked my whole life to understand.

4. What do you do on days you're feeling creatively uninspired?

I go outside. I listen to music. I watch a film, or read a book, or hang with someone I love and have a conversation. Without experience we can’t empathize, and without empathy we can’t create.

5. What advice would you give someone who wants to change their work situation but doesn't know where to start?

Make a list of what your goals are, what you want your daily life to be like, what kind of lifestyle you want to have, what your strengths and weaknesses are, and what obstacles you’re up against. The journey of a thousand miles begins with one step.

6. How do you stay organized? (apps, sites, notebook, chalkboard, etc ...)

Google Drive and my Google calendar save my life on the daily. Aisle Planner and Honeybook are my favorite “wedding world” tools. I use Iconasquare, Instagress and Tweepi for social media. My day planner is the Day Designer by Whitney English.

7. How do you manage multiple clients/jobs without losing your mind?

See all of the above! But really, staying organized, whatever that means to you, is key. Streamlining my business by using all of the necessary tools and creating an established workflow has been a game changer. Also, delegate where necessary. Learning how to trust someone (deserving) to help you with your projects is so freeing.

8. If you could change one business decision from your entrepreneurial journey, what would it be?

It sounds crazy, but without going to law school and learning how to truly stay organized, effectively research and think critically, without my law firm where I learned the best ways to work with clients and make them comfortable, without my knowledge of contracts and liability and employment law, I wouldn’t be nearly as effective as a solopreneur. And I’ve learned so much from my missteps. I don’t know that I would change anything about my journey so far, other than the few times I haven’t followed my gut. If I’ve learned anything, it’s to always follow your gut.

9. Hiring a graphic designer and/or photographer for branding can be daunting for some. What advice would you give them?

With graphic designers I’ve found that timeliness and responsiveness are as key as talent.

10. What is the best money tip you ever came across?

Charge what you’re worth.


Hailey is the owner of Two Roads Event Co. and co-founder of California’s premier event design showcase FRESHbash; an undeniable creative force, with a heart for romance and an eye for detail. She has a passion for storytelling, and for using florals, food, wine, music, and other experiential touches as a vehicle for showcasing who her clients are and what they love.

Both a licensed attorney and a graduate from Wed Prep, the program developed by acclaimed Los Angeles event planning duo Bash Please, Hailey is a unique asset to her clientele– providing the sharp intellect and discretion of a lawyer, combined with the creative energy and aesthetic of an event specialist. Most importantly, Hailey treats her clients as collaborators and friends, making event planning a fun and memorable experience.

Hailey happily splits her time between Los Angeles and Sacramento with her hilarious husband Adam and their equally hilarious rescue pup Shirley by her side. 
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