Female Founders: Cassidy Montalvo Of I’Mperfect Collective On The Five Things You Need To Thrive and Succeed as a Woman Founder
You Don’t Have to Have All the Answers. I often felt overwhelmed by the expectation to know everything about running a business, especially as I have taken on starting a jewelry company. I wish I had understood earlier that it’s perfectly normal not to have all the answers. Another piece of advice my grandpa passed on to me was to never be the smartest person in the room. You always want to be open and willing to learn. Early on, I hesitated to reach out for help, thinking I should figure everything out myself. Eventually, I learned that seeking advice from mentors and peers was invaluable. For instance, when I faced challenges with brand collaborations, I reached out to a fellow creator who guided me through the process, which made a significant difference. When I wanted to start my jewelry company, I went to a friend’s husband who has started many companies and he was able to walk me through the process.
We had the pleasure of interviewing Cassidy Montalvo. Cassidy is a digital content creator known for her vibrant fashion and lifestyle content on TikTok and Instagram. Born and raised in Northern Virginia with five sisters, Cassidy Montalvo grew up watching YouTube stars like Jenna Marbles, and she dreamed of a career in fashion or cosmetology. Fast forward to now, the mom-of-two has garnered a passionate online following of over 3.6 million and counting. Cassidy’s career began in the hospitality industry working in San Diego, California full time as a hotel manager. When the pandemic hit and the hotel was forced to temporarily close its doors and Cassidy was stuck at home, she decided to give content creation a shot — and her videos took off. When her hotel job called her back, she found herself with a tough decision to make, as she tried to balance both jobs in addition to raising her daughter. She ultimately took a leap and left the hospitality industry to pursue content creating full-time. With a focus on expressing personality through fashion, she connects with her growing audience by featuring her unique style and fashion sense, family moments and everything in between. This fall, Cassidy is launching her very own jewelry brand, the I’Mperfect Collective.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Thank you so much for wanting to talk with me!
My journey into content creation started in an unexpected way. I managed the front desk for the Hotel Del Coronado, a role I loved despite the demanding hours and working holidays that comes with hotel work life. When COVID hit and the hotel shut down, I found myself furloughed and at home with an abundance of free time. To channel my workaholic tendencies, I dove into puzzles and projects, but it wasn’t enough. Pretty sure my poor husband was going nuts at this point.
Styling hair for friends and family for special occasions had always been a passion of mine, and as TikTok gained popularity, I decided to film some hair tutorials for fun. To my utter surprise, they started going viral. Around that same time, the hotel called ready for me to return to work, but I was beginning to see the potential of turning this newfound passion into a serious career. Balancing the hotel, my growing online presence and, of course, my family, was extremely challenging, especially as my audience began asking for makeup tips, outfit ideas, and more personal content.
Eventually, I realized I couldn’t fully invest in all paths. With a big move from San Diego to Virginia on the horizon due to military orders, I made the difficult decision to leave the hotel industry. It was a leap of faith, but one that, in hindsight, I’m incredibly grateful to have made. Now, I share my journey as a military wife, mother of two, and dog mom, while blending hair, makeup, lifestyle tips, and everyday moments into content for a wonderful community. Connecting with my audience feels like having the best group chat you can imagine and together, navigate life’s ups and downs.
Can you share the most interesting story that happened to you since you began leading your company?
One of the most interesting experiences since I started my content creation journey happened during a live Q&A session. I was discussing hair tips and makeup hacks when someone unexpectedly shared a personal story about how my tutorials helped them feel more confident after a tough time in their life and how it changed their path.
It really struck me how powerful social media can be — not just for sharing tips, but for fostering a supportive community. It transformed my approach to content, and my emphasis quickly shifted to a focus on the importance of connection and engagement. Honestly, sometimes it feels easy to slip into the role of a “bobblehead” just doing hair and style, but moments like that interview question remind me how thin the line is between the online world and real life. It’s experiences like this that make this journey so fulfilling and meaningful.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Truthfully, I’ve made many mistakes on this journey, so it’s tough to pinpoint just one as the funniest! One memorable moment was when I spontaneously decided to respond to an Alix Earle video. She looked stunning but humorously commented that she felt like a “mom at drop-off.” I thought that was hilarious, so I stitched her video while wearing my own drop-off outfit — complete with no makeup, messy hair, an oversized sweater, slippers, and a cold coffee in hand.
To my surprise, that video ended up being featured on GMA, Rachel Ray, and several other news outlets. It certainly wasn’t my most glamorous moment as a fashion and beauty blogger, but it made me (and apparently a lot of other people!) laugh and showed that authenticity can really resonate!
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
My husband is truly the MVP of my journey. From the very beginning, he was my biggest fan, always cheering me on as I started making videos. When my content began to gain traction and I felt intimidated, he was the first to encourage me to keep going.
Balancing my job at the hotel and creating content was a challenge, but he took on the bulk of our household responsibilities, allowing me to focus on building my dream career. When I needed funds for product reviews and hauls — without compromising my integrity with brand deals — he even sold his sports car to support me.
Through every high and low, he has never doubted me. I can say with absolute certainty that I wouldn’t be where I am today without his unwavering belief in me, especially during the times I struggled to believe in myself.
According to studies, only about 20% of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
I’ve found many women (myself included) struggle with the challenges of imposter syndrome while trying to navigate the balancing act of societal expectations. Even when we have the skills and drive to succeed, it’s easy to doubt ourselves and feel like we don’t belong in the entrepreneurial space. This self-doubt is just another brick on top of the pressures to juggle career aspirations and family responsibilities flawlessly. Unfortunately, we can also be our own worst enemies, harshly judging ourselves and each other, which only fuels these insecurities. It’s something I really believe we, as a society, need to address and change.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
Oh boy, that is a loaded question! I think to really tackle the obstacles women face in entrepreneurship, we need to first work on building supportive networks where we can uplift one another. We all know how much self-doubt can creep in, so practicing self-compassion is key, but can be really hard when you feel alone in your space. On a broader level, we should encourage conversations about the unique challenges women encounter and create spaces where we can share our experiences openly and safely. Men often have access to networking opportunities like golf outings, industry conferences, and exclusive roundtable events that can lead to valuable connections and mentorship — opportunities that may not be as readily available for women. Celebrating female entrepreneurs in the media can inspire others to take the leap. For example: it’s always rubbed me wrong that Shark Tank (a show I really love) has six sharks and usually only one of them is female. And when it comes to government support, increasing access to funding for women-led businesses and promoting family-friendly policies like paid leave and affordable childcare would be such a game-changer.
This might be intuitive to you as a woman founder, but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
Oh absolutely! For one, we bring unique perspectives and experiences that can lead to fresh ideas and solutions that truly resonate with people. I believe women tend to prioritize collaboration and community, which can create a more supportive and creative work environment. Plus, when we step into entrepreneurship, we’re setting an example for the next generation, showing young girls that they can chase their dreams without limits.
What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?
The first is a big one, and it’s what I hear the most. When I first started, I was unemployed; living on credit and a prayer. Many, many people believe you need a lot of money to start a business, but the truth is that many successful entrepreneurs begin with very little and grow their ventures gradually. Another common myth is that you need a perfect plan before you start, but entrepreneurship is all about learning and adapting as you go. It’s okay to begin with just a rough idea and refine it along the way. Then there’s the idea that success happens overnight — most successful founders face numerous challenges and setbacks before they achieve their goals, and it takes time and persistence to get there. Lastly, some think you have to sacrifice your personal life completely. While starting a business requires dedication, sacrifice and hard work, there is a balance that can be found.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
I don’t want to dissuade anyone reading this, but I don’t believe everyone is cut out to be a founder–and that’s perfectly okay. Successful founders often share specific traits. For example, resilience and a thick skin is crucial. The journey of entrepreneurship is filled with ups and downs, and being able to bounce back from setbacks is essential. A strong sense of adaptability is also important — founders need to pivot when things don’t go as planned. If you cannot adapt to your changing surroundings, you will have a very hard time as an entrepreneur.
Another key trait I have found is a willingness to take risks. As entrepreneurs, we very often need to step outside our comfort zones and make decisions without a guarantee of success. Passion is vital too; a genuine love for what we do can fuel the long hours and hard work required to build a business.
I think some people might be better suited for a regular job, because many prefer and value stability, predictability, routine, or find comfort in having a structured environment with minimal personal risk.
Ultimately, both paths are valid, and it’s about finding what aligns best with your strengths, values, and lifestyle preferences. Not everyone has to be a founder to make an impact or be successful in their career.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
1. It’s Okay to Start Small
I wish someone had told me that starting small is not only acceptable but often necessary. When I began creating content, I felt the pressure to have everything perfectly planned out and to launch with a grand vision. Instead, I learned that starting with simple ideas and gradually building on them helped me gain confidence and allowed me to refine my style along the way. For example, my initial hair tutorial video was just me experimenting and was FAR from perfect. My content back then looks nothing like my content now. It’s all a journey! Have fun!
2. You Don’t Have to Have All the Answers
I often felt overwhelmed by the expectation to know everything about running a business, especially as I have taken on starting a jewelry company. I wish I had understood earlier that it’s perfectly normal not to have all the answers. Another piece of advice my grandpa passed on to me was to never be the smartest person in the room. You always want to be open and willing to learn. Early on, I hesitated to reach out for help, thinking I should figure everything out myself. Eventually, I learned that seeking advice from mentors and peers was invaluable. For instance, when I faced challenges with brand collaborations, I reached out to a fellow creator who guided me through the process, which made a significant difference. When I wanted to start my jewelry company, I went to a friend’s husband who has started many companies and he was able to walk me through the process.
3. Resilience is Key
I wish I had been better prepared for the ups and downs of entrepreneurship. There were days when I questioned my choices, especially when content didn’t perform as well as I hoped. I learned that resilience is essential; it’s about getting back up and trying again. Every flop is a learning experience not a failure and should be treated that way.
4. Comparison is the Thief of Joy
In the beginning, I often found myself comparing my progress to others in my niche, which only led to self-doubt. I wish someone had emphasized that everyone’s journey is unique. Instead of focusing on what others were doing, I learned to celebrate my own achievements, no matter how small. For example, when I hit my first milestone of followers, I took a moment to appreciate my growth instead of feeling inadequate compared to others. I may be the only creator that never ever looks at analytics. It’s too easy to play the comparison game and that will ultimately change your authenticity.
5. Balance is Crucial
Finally, I wish I had understood the importance of finding balance from the start. I dove headfirst into creating content, often neglecting my personal life and self-care. Over time, I realized that burnout was real and could impact my creativity. Now, I prioritize time for myself and my family, ensuring I recharge regularly. This balance not only improves my well-being but also enhances the quality of my content. This has also been true for starting a company — it is hard work. I was about to kill myself to make the launch date I wanted. Eventually I had to step back and adjust my expectations — and my launch date — and that’s ok.
These lessons have shaped my journey, and I hope sharing them can help others navigate their own paths with greater ease!
How have you used your success to make the world a better place?
I believe in giving in secret; my grandpa always said that we should do the right thing simply because it’s the right thing, not for recognition. I’m grateful for my success, as it has allowed me to assist particular causes that are near to my heart. I hope my videos also serve a greater purpose by encouraging others to embrace their quirks and unique styles, wear what makes them happy, and forget about societal pressures. Ultimately, I want everyone who engages with my content to walk away feeling empowered and confident in themselves and I hope that has a trickle effect on society as a whole.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be?
If I could inspire a movement, it would focus on embracing authenticity and self-acceptance in a world that tells so many girls they just aren’t good enough. In a world that often pressures us to conform, I believe there’s immense power in encouraging individuals to celebrate their true selves, quirks and all. This movement would promote body positivity, mental health awareness, and the idea that it’s okay to be different.
If I had all the power I would hope to create safe spaces — both online and offline — where people can share their stories, support one another, and learn to love themselves without comparison. By fostering a culture of acceptance, we could reduce the stigma around mental health issues so many women suffer in silence with (PPD survivor speaking here) and empower people to pursue their passions without fear of judgment. Ultimately, this movement would aim to uplift everyone, helping them feel valued and confident in their own skin, which would ripple out to create a more compassionate and understanding society.
Is there a person in the world with whom you would love to have a private meal with, and why?
If I could have a private meal with anyone, it would be Lucille Ball. Her incredible talent in comedy and her trailblazing role as a female producer in a male-dominated industry are truly inspiring. I admire her ability to blend humor with genuine emotion, creating memorable moments that resonate with so many people. I’d love to hear her thoughts on overcoming challenges, the importance of creativity, and how she navigated her career while breaking boundaries for women in entertainment. Plus, I can only imagine how delightful and witty the conversation would be!
Female Founders: Cassidy Montalvo Of I’Mperfect Collective On The Five Things You Need To Thrive… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.