Today we’d like to introduce you to Megan Caldwell.
Hi Megan, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
The truth is, I never thought of being a florist growing up. I was simply a fourteen year old girl that needed to find a job. I knew that with my young age, options were going to be limited. This is how I ended up job hunting in downtown Los Gatos, California. Originally, I was going to a small plant shop, yet they were not interested and I ended up walking though a flower shop down the road. I lucked out there because I came in during a busy season and I remember the owner saying “we can hire you for the holidays” implying I probably wouldn’t be needed afterwards. As fate has it, I ended up fitting right in. I did everything and anything that needed to be done- kept the flower floor stocked and clean, made wrapped bouquets, organized and tidied the cooler, etc. There was no job I wouldn’t do. In the meantime I was learning from multiple talented florists, slowly getting the hang of different techniques. I had the creative eye for it although I had no official training and did not go to floral design school. As I worked there throughout high school, I never really thought it’s what I would continue to do. I loved it and did dream of owning my own shop, but as I can be a practical thinker, I never thought it would actually happen and it was only just a fantasy.
As life happens, I moved out at seventeen years old for safety reasons. It was unexpected, unplanned, and I had to become an adult sooner than I was prepared for. This led to me needing to shift my career focus into something, I believed, would be more practical. Despite my love and passion for the floral industry, I needed to make more to support myself. One thing I had dreamed of doing was being an interior designer so I found a job with a staging company. With as much hope as I could have, I began the job that ended up just making me a glorified mover. I absolutely hated it. I went from working with fresh flowers to being in a warehouse full of HomeGoods items. I have never been one who can work a job just for the money. It doesn’t matter enough to me, I need to be fulfilled with the work I do. The mix of a job I did not thrive in and living with an awful partner led me to moving to Oregon.
Why Oregon? Well, for as long as I can remember I have always dreamed of having a farm. My grandparents were born and raised in Southern Oregon and at that time were living there. Despite all my family and friends being in the bay area I knew I needed a change.
Funny enough, when I moved to Southern Oregon I had no plans to necessarily stay or to work at another flower shop. Quite the opposite actually. I planned to take my time exploring Oregon to decide where I wanted to end up and to look around for a career that would take care of me. Yet, I found myself falling in love with Ashland. I also couldn’t seem to take much of a break from working as a work ethic was instilled in me since I was born. I applied to any job I could, finding myself interviewed for a physical rehab company, despite having no background or education in it. I distinctly remember them asking in a second round of interviews “what makes you passionate about this position?” That really stuck with me. I know I gave some sort of professional answer but the truth is, I wasn’t. Driving back from that interview, I saw a flower shop and decided to just check it out and maybe get some flowers for myself. I ended up meeting the owner, connecting with her, and finding out she was hiring and hoping to one day soon sell her shop. I remember making a pro and cons list of both of the jobs. I remember feeling like I had to change my career or I wouldn’t be successful. I remember knowing in my gut I was going to be a florist once again.
Working there taught me so much and I am forever grateful for my time there. It was the first time as a florist that I was the lead designer. I learned how to run a shop on my own and get a glimpse of what ownership could look like. Although I did not end up buying that shop, I needed that experience to get where I am. When it felt like a dead end there, I went to a management position at a florist in Medford. Another great learning experience for me. This is where I learned how important it is to treat your employees well. How important it is to care more about the product you sell than making a quick dollar. This is where I met my future business partner.
Since I had been in the floral industry in the rogue valley for some time then, one of my flower wholesalers told me about Penny and Lulu being for sale. At that time, I was feeling so doubtful of my life as a florist. I thought this new job was going to be the answer yet it was just a let down. I was considering moving to Washington with my close friend and starting anew. This felt like a sign to try and see what would happen. Thankfully I had chosen not to go to college since I would’ve had to pay out of pocket and couldn’t justify it. My future business partner also hadn’t. Even though we were young girls in their 20s, we didn’t have debt so we thought we may have a chance.
Getting a business loan was a stressful and difficult process. This time of my life is a blur of emotions. I was doing things I didn’t know how to do, making spreadsheets I didn’t fully understand, and fully going on a whim. This is not something that came easily and it truly was the most stressful moment of my life. Thankfully I was doing it with someone else because there was truly no way I could’ve done it myself.’
When we bought the business, it didn’t get less stressful. People were very hesitant to trust us since Penny and Lulu had such a wonderful reputation. For a while I felt like I was designing for the old penny and lulu, not for my style. Little by little, we began trusting ourselves and making it our own. People began to trust us too.
April 2026 my business partner decided she did not want to continue in this industry. It was shocking for me as we were best friends and seemed to work really well together. Another learning experience for me , you can’t force someone else to communicate and you can’t force passion. When it happened, I fell apart. I didn’t want to do it alone. But we still had a business loan to pay off,and I felt I didn’t really have a choice. Now I am the sole owner and I am so proud of where I have come, and how I’ll continue to grow.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Absolutely not, as mentioned before every part of this journey has had it’s challenges. Getting the business loan at 22 years old, taking over a well known business and having to prove my skills, and now- at it alone without my business partner. I constantly feel unprepared and that I have no clue what I am doing, yet talking to other business owners I realize it’s a common experience. I truly do not believe that being a business owner will ever be easy. I do know that I will continue to learn grow, and find the right people to support me and help me along the way.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I am a florist and have been one for over ten years now! My specialty is unique flowers, sourcing locally grown when in season, and lots of fun textures with complimentary color palletes. I also love fashion, and for me personally, floral design is another way I can express style. I love experimenting with different colors, textures, and flowers. I do not have a traditional website where people chose a photo and I replicate it. I find that limits artistic freedom. All of my options are “designers choice” within a color scheme. This ensures that every bouquet is unique, artistic, and truly special. It allows me to get various flowers and really switch it up, rather than sticking to the same designs/flowers. Supporting the community is huge for me, so I am extremely passioante about sourcing my flowers locally when I can. It is not the cheaper option however it is what I truly care about doing. I have no desire to make a bunch of sub par arrangements just to get them out the door. I create intentional, ethically sourced items knowing that it is the most sustaianble option for our community. With as many challenges as I may face, knowing that I get to support the local economy and small businesses all over truly makes it worth it for me.
Is there anyone you’d like to thank or give credit to?
I am blessed to say that there are so many people that have helped me get to where I am. As I mentioned, all of my collegues have taught me what I know abolut flowers and design. My boss, Kellie, in Ashland pushed me to grow and trusted me with managing her shop which gave me a glimpse into owning one myself. Joan with Le Mera gardens (my main local wholesaler) always offerred a listening ear and words of encouragement. My dear friend, Miyo (who I met working for Kellie) has known me, been there for me, and believed in me every step of the way. She called me daily after my business partner broke the news of leaving, ensuring I was doing alright and giving me words of affirmation. Truly, I do not know what I would have done without her. My incredibly talented social media expert, Valentina, who has helped my shop flourish and is passionate about the business’s success. She truly cares about me and has been a guiding hand through difficult times. My partner, Ben, that has stuck by me though my range of emotions- keeping me sane throughout it all. There are an abundance of people that made this, and continue to make it happen.
Contact Info:
- Website: https://pennyandluluflorist.com
- Instagram: https://www.instagram.com/pennyandlulu/
- Facebook: https://www.facebook.com/PennyandLulu/
