How Lindsey Drennan is helping entrepreneurs tap into their 'Creative Juice'



If there's one thing we've learned from COVID-19 it's that adaptability is key, especially for small businesses. As brick-and-mortar stores move online and the world of e-commerce expands, many entrepreneurs and small business owners are grappling with the task of establishing their presence online.


For most modern brands or businesses, 'content is king' when developing an online presence but content can be expensive. Hiring contract creatives, establishing product shots and developing a social media strategy can be costly and time consuming for many small business owners. So, what's the solution?


Lindsey Drennan is a photographer, producer and 'solopreneur' on a mission to solve the content challenges faced by many entrepreneurs. In January 2020, Lindsey launched We Get That, a video and photography service company that helps brands stand out through impactful content. After working with brands through We Get That, Lindsey recognized she could further reduce the costly overhead of content by simply providing entrepreneurs with the resources and guidance to produce their own digital content. Just last month, Lindsey Launched The Creative Juice Collective, an entirely e-commerce business that teaches female entrepreneurs to create eye-catching social media content to better share their brand story.


Winslow: You've worked as a professional photographer, a content producer and most recently you've started a journey as an entrepreneur. Tell about the paths you took to get you to where you are today. Lindsey Drennan: I knew from a very young age that I wanted to be a photographer, it was something I never questioned. Creating art has always felt instinctual, and this instinct motivated me from day one. When I was in my final year of college, I applied to Vogue Magazine for an internship in their photo department and was told, “Sorry, you would have to come here just for a 20-minute in-person interview just to be considered.” Without hesitation, I responded with “No problem! When should I come?” We arranged a date, I hopped in my car and drove to New York City for a 24-hour whirlwind trip and I landed the position. I was over the moon excited to be the first international student to complete an internship at Vogue. That whole experience showed me that if you want something bad enough, you can have it. Shortly after graduation, I moved to Toronto. I was so inspired that I immediately started curating my own fashion editorials and started collaborating with some of Toronto's best talent in the fashion industry. To this day, it's some of my favourite work. However, in an industry where it can be challenging to make a predictable income, I decided I wanted more financial security. This wasn’t an easy decision, but I knew something needed to change. I took a chance and got a job at a small communications agency where I photographed content for clients and influencer campaigns.


The financial security felt like a relief, I was able to learn new skills and I was exposed to a different demographic than I had been in the past. After a year-and-a-half at that agency, an old contact reached out to me and asked if I would be interested in a producing position at a production company. At this point in my career, I didn't know exactly where I was going, but I knew I wanted as much experience and exposure as possible. I wanted to explore all of my options and opportunities. I wanted to grow. I wanted to creatively evolve in a dynamic industry. As the director of content, I produced, shot, and executed amazing social media campaigns and content for Canada's top brands.


Fast forward to Fall 2019: I was about to leave for Southeast Asia for a 5-week trip to get married and travel and then something hit me it was time to launch my own company. All of the people, jobs and friends up to that point had prepared me to tackle the entrepreneurial world. In January 2020, I launched my first online business We Get That, and just two weeks ago I launched my second business The Creative Juice Collective.


My journey was a zig-zag, and every entrepreneur's story is going to be different. There is no one way to do things or be successful. There is no wrong way, there is only YOUR way. Often we do not fully understand why we are where we are, but we have to have faith in the journey, embrace it, and trust that it will guide you to exactly where you are meant to be. W: As you mentioned, you've just launched your company The Creative Juice Collective. Can you tell us about what inspired you to develop this brand and can you share what The Creative Juice Collective is all about? LD: I am SO excited about this business, and I hope others will be too because I really think there is a need for it and how it supports people. I have been approached by female entrepreneurs for years looking to hire my services, but they just could not afford it, which I completely understand as a new 'solopreneur'.


After helping friends with their brand content over the years, I realized that they actually didn't need me to make great content for them. Instead, with the right coaching and resources, they could do it themselves and save their money. That is what motivated and inspired me to start The Creative Juice Collective a go-to community to empower kick-ass female entrepreneurs to tell their brand story through eye-catching social media content. I provide these entrepreneurs with resources that teach the technical and visual aspects of photography, videography, design and content creation, as well as providing a community for support and feedback. The best part: you don’t need any professional equipment. With the technology we have today, you can create amazing content on your phone anytime, anywhere.

W: Amid the current challenges of COVID-19, many small business owners and entrepreneurs are being forced to pause their projects or close shop altogether. But here you are, launching an entire e-commerce business during a global pandemic! What's it been like to launch The Creative Juice Collective during this time? How do you think you can help other entrepreneurs adapt and improve during this time of uncertainty through The Creative Juice Collective? LD: I actually started working on this project back in January, but because the launch of We Get That was so busy, I wasn't able to spend as much time building The Creative Juice Collective. When COVID-19 hit, all my scheduled photoshoots came to a halt. Suddenly, I had the time and space to nurture and develop The Creative Juice Collective. Truthfully, this global pandemic has been a great opportunity to create useful content for female entrepreneurs because it's needed now more than ever. Like me, these entrepreneurs have the time to focus on content creation and social media and they are realizing the importance of being present in a digital world. I think this is the perfect time for people to get more comfortable, creative and courageous about digital marketing and content creation. Creative Juice is a community that helps women become comfortable with their phones and mobile apps, being in front of the camera and learning about key items like lighting. If they are serious about starting the company they always wanted, or spending more time curating their side hustle, or if simply want to refine their online presence, this is the place for them.

W: Starting a business seems overwhelming for many people at the best of times. Managing invoices and payments, establishing resources and project timelines all of these processes require a bit of a learning curve. What skills and experiences from your past work as a photographer or content producer were you able to leverage when building The Creative Juice Collective?

LD: I think having a production background and working at a communications agency prepared me for business. As a producer, I had to have exceptional attention to detail because I was responsible for executing very large creative projects, similar to a project manager but for execution. I was managing schedules, budgets, teams, locations, insurance, permits, talent, rentals, invoices and everything in-between.


My time at the agency also introduced me to the importance of digital marketing and strategy. I am also constantly learning from other female entrepreneurs, online courses and readings. I used to say how much I hated writing, and now I am learning about copywriting. As an entrepreneur and 'solopreneur', you have to be open and willing to learn things you don't know and be willing to take advice from others to grow, adapt and pivot. You're often wearing all the hats of the company until you can hire a team. I also think that having a community of supportive people around you is key, whether that is online or in-person. You want to have a place where you can share your wins, ask questions and also support others.

W: What has been the biggest lesson you've learned so far during this journey? LD: I've learned that you will always end up where you are supposed to be. Trust and embrace the journey. Comparing your journey to someone else’s is destructive because no two journeys are the same. Stay focused on your path, and it will guide you to where you are meant to be.

W: What advice do you have for creatives or entrepreneurs who may be struggling during this time because their work/business requires them to be in-person? LD: No two creatives are the same, and art is subjective. In these times we are called to be our most creative, so tap into your talent, get creative and have fun. Try to embrace the situation instead of resisting it, because it will make the process easier and more fun. I think we can all agree that life is short, and it is far too short to not have fun and create what you love. If you focus on that, the rest will come. I promise.


You can learn more The Creative Juice Collective here.


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