Interested in starting your own entrepreneurial journey in clothing but unsure what to expect? Then read up on our interview with Colleen Ramage, Co-Owner of Philistine, located in Toronto, ON, Canada.

What's your business, and who are your customers?

My business is Philistine; we're a Toronto-based shop selling a blend of new & vintage clothing, accessories, apothecaries, and lifestyle items for all genders! Our customers are people who value the impact that arts and culture have on clothing and personal style. The ethos behind Philistine is an unpretentious environment where customers can access a thoughtful assortment of contemporary brands and local makers that reflect our current culture. My business partner and I always felt like we were being hazed when shopping in trendy boutiques and made it our mission to create a space where people feel welcome and can allow themselves to be vulnerable – because trying on clothing, expressing yourself creatively through your wardrobe or finding your personal style while accepting assistance from someone you may not really know – can be a very vulnerable process.

Tell us about yourself

When I was in university, I was on a tight budget and really leaned into thrifting. In the days before smartphones, I would use road maps to plot out afternoons or days driving from thrift store to thrift store and finding treasures for myself. I worked at Urban Outfitters then, and my co-workers would comment on my finds, so I started taking down people's sizes and any requests to help offset the cost of my gas. So, my entry into small business began somewhat organically.

I've always loved listening to what someone is looking for, and sometimes they don't even know; you have to ask them the right questions, which makes it like a puzzle. But seeing their reaction when you find that special piece is a rush! There really is nothing like it – and that's what motivates me every day.

What's your biggest accomplishment as a business owner?

Honestly, making it through the pandemic was a huge awakening for me as a business owner. I do all the financials for the business, so making it to the other side while so many more experienced, more established, and had deeper pockets failed showed me that I had all the tools I needed to succeed. Obviously, we're still dealing with some of the 'fallout' from this period, like government loans that need to be repaid, but we're still here and will take it in stride. That grueling experience gave me the courage to reach further when it came to our business and open the second location!

What's one of the hardest things that come with being a business owner?

I would say self-doubt and then measuring your value as a person by the success of your business. Self-doubt can eat away at you, always thinking about what-ifs and thinking that you don't have what it takes to run your business, but no one knows your vision better than you. Measuring your personal value by the ebbs and flows of your business is so toxic and makes life so much harder than it needs to be. There will be ups and downs, but you must remember that it doesn't reflect on your value as a person.

Work-life balance is another thing I struggle with that relates to attaching your personal identity to your business. Just remember that you can take time away, you need to entrust some things to other people, and you won't be able to accomplish anything if you run yourself into the ground or dry out creatively. But this is a work in progress for me, so don't be too hard on yourself!

I would say to anyone thinking about opening their own business to take the chance. We've seen the version of the world that big business offers us. It's boring, it's one-size-fits-all, and it's impersonal. I don't think that's what most people want. To have a vibrant culture with a place for everyone, different people with unique visions need to build it. I think that's what small business does. I believe this is something that matters enough to most people that they will take the time to discover and patronize independent enterprises.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

Starting: Be brave, be organized. People will LOVE to tell you why it's a bad idea to go your own way, but in my experience, it feels like something you need to do – so don't listen to them. Technically, it is a risk in terms of statistics, but that doesn't mean it's a bad idea! Just stay organized, make lists of what you'll need to get started, organize your break even, find out how much financing you can secure, and think about what your location will be (brick & mortar, online, etc.). And then dig deep, and stay brave!

Running: Keep going – it's not a race; it's a marathon. There's time to rejig, revise, and rework; just focus on the things you can actually control that will positively impact your business.

Growing: EDIT - always be prepared, to be honest with yourself about what's working and what isn't. Your creative vision isn't written in stone, and anything you come up with, is inherently authentic to you, so always be willing to workshop the image.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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