We recently connected with Natalie Osborn and have shared our conversation below.
Hi Natalie, thanks for joining us today. Alright, so we’d love to hear about how you got your first client or customer. What’s the story?
Thanks for having me! I guess the most obvious thing you notice when you first meet me, is I have a pretty unique accent. I’m Australian! I’ve called San Diego home for nearly a decade and I’m grateful to have the opportunity to build my life and career here.
Proposals of San Diego’s first client was, I believe, a sign from the Universe that we were on the right path. For someone who has high expectations for herself, it cemented the most important lesson I’ve learned in work and business; “Done is better than perfect.”
We had NO website. We had NO prior experience. We had NO business goodwill. We had NO decorations. What we DID have was a pin on google maps… and my cell phone number. It took one week for Marco to call me with an idea in his mind, and two months for us to find ourselves at Mission Bay, designing our very first surprise proposal for his gorgeous fiance Lara.
I hung up the phone and immediately panicked. I thought “what have we DONE??” I don’t know how we pulled their event off, but there were many lessons learned that day. Budgeting and knowing your value within your industry are crucial to the success of any business. Marco and Lara got the proposal of their dreams and I think we were lucky to make $5. Since then, we have designed many unique and beautiful proposal packages, but the Dreamscape Canopy, an adaptation of the original design Marco gave us, is still our most popular proposal.
Natalie, 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?
I am the owner of boutique proposal planning company “Proposals of San Diego.” On the occasional weekend when I am not bringing a lucky someone’s engagement dreams to life, you can find me having adventures with my main man Panda the Sheepadoodle, scuba diving in La Jolla or sending it with the San Diego Onewheel Riders.
I feel like I found myself in the event planning industry almost by accident. A beautiful friend and I were walking our pups on Coronado Island in January of 2021, admiring those luxury “pop-up” picnics which really took off during the pandemic. “I’d love to do something like this!” I said, “…but there’s so many companies already, and I don’t think we could do it better than them.”
Continuing our walk, we encountered this poor guy setting up his own marriage proposal; a strong wind had come up, insane crowds gathered to stare, he was sweating and very clearly stressed. The “Marry Me” balloons were the only thing being swept off their feet. It was my lightning bolt moment. We looked at each other and simultaneously screamed “POP UP PROPOSALS!!!”
In this moment, Proposals of San Diego was born. Now, I aim to bring a truly unique, San Diego experience to marriage proposals. I create moments that reflect the unique love story of each couple.
I take great care to bring my client’s vision and personality out in their proposal. I know this city intimately, and love working alongside other young, dynamic vendors and local artists to guide clients in bringing their ideas to life. By handling the details from start to finish, Proposals of San Diego ensures that when the big moment finally arrives, all the clients need to remember is to keep their cool, and get down on one knee.
The biggest concern I hear from my clients leading up to the big moment is managing their partners expectations against their budget… and keeping it all a secret. To solve this, Proposals of San Diego offers “All-Inclusive Proposal Packages” with the goal of taking the stress and pressure out of planning, so when the big moment arrives, all you need to do is keep your cool long enough to get down on one knee. Everything else is already taken care of! Each package can be reviewed, and scheduled directly through the website, offering clients an affordable alternative to traditional proposal planning. Events can be arranged at short notice and allow the flexibility to customize personal details to make the experience truly unique for each couple. With upfront pricing, Proposal Packages are ideal for the person who wants to pop the question in a truly special manner, but may not have the time or means to put it together themselves. It’s a radical departure from traditional proposal planning services, which require clients to inquire directly with a planner and then build an event from scratch.
I have been planning unforgettable engagements for two years now, and the next adventure, which I am excited to announce here(!) is the introduction of our online store. We have already started to offer customizable keepsakes such as etched champagne glasses, engraved ice buckets and floral arrangements to elevate our client’s proposal events. Stay tuned over the next couple of months to see what we have in store to celebrate “The After Party.”
What sets me apart from others is my commitment to working personally on every single event. I’m most proud of building a business where I get to work directly with my clients; from the planning stage, right through to execution. Now I’m beginning to build a team of amazing event decorators who are also committed to handling the finest details. We will be right by your side to offer you our experience, local knowledge and advice, every step of the way. When the big moment arrives, we get to share in that experience and meet people on what is the BEST day of their life.
What matters most is my couple’s satisfaction. Seeing happy tears or beaming smiles is what makes me keep coming back to the crazy, day after day.
As the No.1 San Diego proposal planner, I want my clients to know that my entire goal is to support them to make their proposal exactly as they dream it. My team and I will be with them every step of the way to provide insight, guidance and support. I’m a romantic at heart with a passion for the classics. I love to read about how people meet and are swept off their feet with the most romantic experience imaginable. That’s why when you call me, the first thing I’ll ask you is “what’s your partner’s name… and how did you meet!?” And I am fully expecting to receive the Disney version of your love story.
For people who may not have the confidence, means or flexibility to do it themselves, I get to help channel their inner romantic. Believe me when I say EVERYONE has a romantic side. I was once the girl interviewed for an article about how awful dating culture can be in San Diego… Since then I’ve experienced dozens of “they said yes” moments. I have the privilege to build people’s imagination and fulfill their dreams of a happily ever after. Despite personal experiences both positive and negative, I believe there is always joy to be found in other people’s romance, and I remain supremely confident in the power of demonstrating love.
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
It started with “The E Myth” by Michael E. Gerber. Its not a sexy business book, but its one return to over and over. I recommend it for anyone considering entrepreneurship as this book shows how to work on your business, not in it. It demonstrates how to systematize, and how to get your team to work without your interference, so you can do the work you love rather than the work you have to do.
The hardest lesson for a budding entrepreneur to come to terms with (myself included) is no longer working in your business but on it. The book uses the example of a woman who just adores cake decorating, so she decides to make a career of it, and opens a bakery. Once the bakery is open for business, she is so busy running the business of a bakery that she never decorates a cake ever again. The lesson here is if you have a passion for decorating cakes, get a job in a bakery. If you have a passion for entrepreneurship, start your own business.
It’s been two years of hard work, but I have finally gathered a wonderful team around me and am able to focus on the work I love. The single best resource to get me to this point has been SCORE. They are a 501(c)(3) nonprofit and a resource partner of the U.S. Small Business Administration (SBA). SCORE has the nation’s largest network of volunteer, expert business mentors, and are solely dedicated to helping small businesses get off the ground, grow and achieve their goals. The best part… It’s completely FREE!
I will shamelessly champion SCORE and the invaluable advice I have received from my mentor, Beverley. Check them out at www.SCORE.org
Any thoughts, advice, or strategies you can share for fostering brand loyalty?
Social media! I don’t use it too much to bring in new clients, but Instagram in particular has been a fantastic way to keep in touch with past couples. It has been so exciting to see my couples move ahead in their lives; seeing photos of engagement parties, weddings and even a new baby or two. It’s a rare privilege to even have the opportunity to share in such an important milestone as an engagement, but another thing entirely to continue keeping in touch after the fact, and one I am truly grateful for.
Contact Info:
- Website: https://www.proposalsofsd.com/
- Instagram: https://www.instagram.com/proposalsofsd/
- Facebook: https://www.facebook.com/proposalsofsd
- Linkedin: www.linkedin.com/in/natalie-osborn-19327749
Image Credits
Andi Priego Photography Lani Quinn Photography