Alright – so today we’ve got the honor of introducing you to Maddy Anderson. We think you’ll enjoy our conversation, we’ve shared it below.

Alright, Maddy thanks for taking the time to share your stories and insights with us today. Often the greatest growth and the biggest wins come right after a defeat. Other times the failure serves as a lesson that’s helpful later in your journey. We’d appreciate if you could open up about a time you’ve failed.

Owning a business comes with a substantial list of pros and cons. A major pro being, freedom, in mostly every context; freedom in picking your own schedule, freedom to be creative, freedom to grow your own passion alongside your friends and family. The pros make it worth it, but cons such as; having to hold yourself accountable, educating yourself on the entirety of your pursuit, and managing personal professional relationships can make running and maintaining a business (solo) complicated.

I have made many mistakes during my short 4 years of being a brand owner. I never educated myself on copyright laws, this led to a cease and desist from the head of merchandising for Jim Morrison/ The Doors. Part of my 20 year old self was terrifying, but majority of my mind couldn’t stop thinking “holy shit….Jim Morrison’s merchandising company knows I exist!”. It is kind of crazy the emotions you go through when you own something that becomes bigger than you ever thought it would be. I removed those items immediately, but I couldn’t have been more grateful for that mistake.

I made the mistake of working with my ex-boyfriend/ex-love-of-my-life. We were amazing friends and both had a similar vision for our future. He originally never wanted to be apart of Bye Hollywood, in fact, he declined to help me when I was in tears and slammed with orders. He wanted to start his own brand, which I respected, but when he wanted quick money to leave the state of Florida- he jumped onboard Bye Hollywood. During our first few months of collaborating, things were actually very copacetic. We wanted the concept to be Bye Hollywood and hello world, because we wanted to be larger than Hollywood, larger than life even. We had the most amazing year in 2022, growing rapidly and overwhelmed with orders–we wouldn’t have changed it for the world. I think through falling in love with our work and the success, we had this undying love for each other, so though we were exes, we continued a somewhat relationship. Love hurts more than anything. I have gone through hell in life, nothing hurts more than heart break. I wanted to get back together with him, and would continuously ask him about where we were going with all this. He always just promised an unclear future by saying things like ‘I love you, but we aren’t good for each other, maybe in the future.’ This was during a time where, yes we were exes, but we were in this unofficial relationship. Months passed and I decided I didn’t want to wait for someone to be ready to completely love me anymore, though I loved him so entirely. I started to date again, and this is where everything fell apart– including Bye Hollywood. I could go into extensive detail about the emotional disaster between him and I, but within weeks I removed him from Bye Hollywood, leaving him with half of the money from the business account and later that summer he threaten to sue me. Which was mind-blowing, because I gave everything I could to him and his family. I could’ve never imagined things going the way they did, I even laughed when people said things like ‘don’t mix business with pleasure’ or ‘never go into business with someone you love’, but here we are. We no longer talk, in fact we don’t even follow each other on instagram. After everything, I genuinely wish him the best.

I made the mistake, of being ignorant when it came to anything tax-related. I handed all my information over to a tax person and trusted he’d do everything for me. That’s what I was paying him for right? Well he never filed any of the sales tax… for 4 years (4 quarters per year), in fact he never told me that it was a side of taxes that he doesn’t handle. I take responsibility for not knowing what any of that was. I was 20 and wanted to make shirts and be creative. I was so occupied with the growth of my brand that I thought it would be safest to hand my tax duties over to someone who selected that as their occupation. I ended up owing $33,000 and some change to the state of Florida. A stress most of my 22 year old friends have not had to endure, which I envy.

This panel discussion question asks about a moment of failure, but I don’t believe I have ever truly ‘failed.’ While others might see these as ‘mistakes,’ I view them as essential learning experiences, for which I am truly grateful. To me, failure is something irreparable, something that makes what’s within a person’s control feel unredeemable. So far, I refuse to fail. I don’t make the same mistake twice, because each experience teaches me something new. A quote by Franklin D. Roosevelt has gotten me through the hardest of times, though it now makes my friends’ ears bleed because I recite it ritualistically: “A smooth sea never made a skilled sailor.”

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I always entrepreneurial. I forced my cousins to do lemonade stands with me every summer, I sold led pencils pieces and parts when I was 9, and I launched a small series tank tops (designed done by a Sharpie) which sold at $10 a piece when I was in the 5th grade. I always wanted to hustle and saw value in almost anything. I started Bye Hollywood back in 2020, after dropping out of high school with a pretty terrifying panic disorder. My body was essentially in complete shock after a medical issue, and I could hardly function. I moved to Oregon to find healing, but at 18 years old with a head full of dreams I knew I had to make something of my life. I always wanted to work in Hollywood, my whole family did; my dad works in sound, my grandpa was a director, my uncle is a producer, etc. I wanted to be an actress or singer, something loud and passionate. After getting sick, I felt I had to give up on all those dreams, so hello Oregon and Bye Hollywood. I knew ordinary was not a part of my identity, despite my limitations. I knew I wanted in the clothing industry at this point in my life. I always had a unique sense of fashion, I even took it as a compliment when people would mock what I was wearing, because hey- it grabbed their eye. I grabbed the name Bye Hollywood on instagram, because it was just so authentically me. I had no idea what I was doing, but I spent everyday designing, YouTubing, googling, learning, creating, and envisioning. With zero dollars to my name, I took a loan out from a friend and released my first set of hoodies, which I only sold 2 of, one to my cousin and the other to my brother. I kept going despite being so upside down. I was scrolling through YouTube when I came across “Cyanotype”. I had never seen anything like it. It was originally an old method to developing film. The process works by combining ferric ammonium citrate or ferric ammonium oxalate, and potassium ferricyanide, then overlaying a negative film sheet in sunlight to essentially cast a shadow and print low contrast images. I knew two things; the whole process was beautifully intriguing and no one had brought the concept to clothes and made a brand out of it.
I had no idea if it would work. I spent the coldest months in a shed in Oregon working with very minimal sunlight, testing and making mistake after mistake. Eventually, I printed the very first Bye Hollywood sun print, which was an image of Brittany Murphy- an underrated actress who deeply impacted my life. After researching her story and others like Heath Ledger, Amy Winehouse, Anna Nicole Smith, and more it brought such a new meaning to Bye Hollywood. Hollywood was a darker place than I realized and some don’t even survive it. I shared my thoughts on their stories along with the short videos of me creating the prints, and that was it. Immediately, so many people were intrigued by the process of sun printing, a term that I feel responsible for coining, as it was originally referred to a cyanotype. I grew instantly on TikTok and then followed my instagram. I was sort of in over my head, and there I times I look back and think ‘how did I manage that by myself, with essentially no guidance.’ Within a few months I was a brand owner, a customer service representative, a book keeper, a shipping and handling coordinator, a marketing manager and content creator + so much more. I was also 20 and learning to be terrified of dying before I get to complete everything I dream, versus being terrified of living which my panic days had me feeling constantly. Each item is handmade, and takes a lot of care to get them just right. I cycle through different options of prints each month, and we occasionally bring back some classic for the die-hards in my direct messages who beg for me to reupload certain items. I also offer a custom sun print option for those who don’t see a print they like, or if they want to have just a personal shirt. While they can be a pain to do, they are also my favorite. I have gotten to see what each person likes and I have made so many beautiful gifts for people to give to their significant others/friends/family. I once made a series of shirts of a man’s aunt who passed away, so he could give his mom these shirts of her sister on them. How emotional and how lucky I am to have had the honor to be apart of that moment. I have also made shirts for. influencers and a few celebrities, though I choose not to work with them. I decline to work with influencers, because I want people to be real. Genuinely love what they wear, support and shop small, don’t ask for free product. Authenticity is incredibly important to me, so I want people associated with my brand to wear it because they love it, not because they were paid to say so. But it is really cool when they actually just purchase them and will post. I am always grateful for that. I am back in Los Angeles now, starting a new era of Bye Hollywood after a devastating issue regarding taxes. I am looking forward to new collaborations, new styles, and expanding.

We’d love to hear a story of resilience from your journey.

I’ve endured a lot of loss during my time as a business owner. I was cutting checks to a former business partner, and taking only enough to cover my bills for months. I was gaslit into thinking this person was owed money, simply because he would tear apart my character and self-image almost daily. My hired CPA never filed my sales tax, leaving me with 4 year and 4 quarters worth debt and interest to pay. The state department of revenue told me my violations would result in me becoming a convicted felon, if this wasn’t handled. With over $40,000 in debt, I was left with no money to own and operate a brand, but somehow and someway, I kept going. Both have had financial and emotional impacts. I even experienced severely high blood pressure at the ripe age of 22 years old. Though I was knocked down time and time again, I kept going, my legs getting stronger each time I had to pick myself back up. I have spent the past month focusing on rebranding and rebuilding, both myself and my business. I shared my story with my followers and the support I received outweighed much of the devastating impact this trying time has caused. Hearing people relate and respond respired my courage and my resilience. It is easy to get lost in overwhelm. Negative thoughts like; ‘why is this happening to me?’ start to inundate the mind and body, but I try to lean into that question in a positive manner. Why is this happening? Because if it didn’t, I would live a life I always feared living, one that is ordinary. I wouldn’t have stories to share about how I fought and how I overcame. I could hardly walk when I was 18, but now I am running– not from something, but towards everything I ever dreamed of.

How about pivoting – can you share the story of a time you’ve had to pivot?

I had to unlearn many limiting beliefs. I was never told to reach for the stars. It was too risky in my family, instead I was encouraged to reach for stability. I think stability is an amazing goal, but once I realized that the stars really aren’t that far, I went for it. When I released my first sun print, it blew up almost immediately and my whole life changed. I really felt this burning inside me that made me feel like as long as I brought my passion behind it, I would be successful. I put out sun prints of things that I loved and was passionate about, and the success continued to follow. I craved that satisfaction; people liking and commenting, sales, and personal direct messages daily. When things started to slow, as they do in business, I shifted my focus towards what the people would want to see, but with that the passion was weaker. This perspective wasn’t what worked for my business personally. I think people fell in love with the initial items I released, because I had such a personal love for it, and people love to feel connected to the owners of brands- especially when the item is being handmade. When I loved it, so did they and that is the most filling thing I’ve experienced. I make sure to stay connected with my audience, so that they feel connected to me and the items they are wearing. When I was in a bind, I would just try to produce items quickly, with no real sentiment behind it, these were always my most unsuccessful drops. It is most important to me to be authentic, so I rebranded in a way that ensure there is no releases that don’t encompass passion as the most valued element of each release. So, reach for the stars, but bring your passion with you like it’s the gas that will get you there.

Contact Info:

• Website: https://byehollywood.com
• Instagram: byehollywood
• Facebook: byehollywood
• Twitter: byehollywoodco
• Other: TikTok: Byehollywoodco