Q & A with Entrepreneur in Residence Chelsea Bonner

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We are delighted to bring you access to amazing female entrepreneurs who have paved the way for all of us.


The first lady to hold this seat is Chelsea Bonner, CEO of Bella Management. She is a powerful force in her field and available to support, empower and encourage you to reach your business goals.

Chelsea is a true champion for body diversity and size inclusivity for women, ensuring through her business that the images we see through our advertising showcase what real woman look like.

Founding Bella Management agency in 2002 Chelsea was determined to redefine beauty and the boundaries of the fashion industry. Based in Sydney Bella represents male and female fashion models of all sizes including curve and plus sizes.

We are so thrilled to have someone that lives and breaths diversity and inclusion as our first Entrepreneur In Residence at Freelancing Gems. Over the past two months, we collected all of the questions asked from our Gem members and sat down with Chelsea to find the answers.

1. What was your motivation to start your business? Was Bella Management your first concept? I really want to be my own boss but don’t know what to do!

The motivation is different for everyone. People are driven by all sorts of very different goals so I think the first thing to do is figure out your end game. What do you want to achieve in the long term? I wanted to change my industry to be more divers and inclusive. It was a very person goal. I didn’t think that I would make much money, I thought it likely that I would always have a side-job. My hope was that maybe I’d make enough to cover my bills and I would have been totally content with that.

If financial security is what you want then the type of business you get into doesn’t matter as much as the opportunity for growth and profit. There are some amazing opportunities online for that, for example Amazon sales and the like, which are low overhead and high profit margin businesses.

If it’s a hobby or passion that you want to turn into a lucrative business then reach out to the people you admire most in that area and ask for a little bit of their time. Most business owners I know are happy to share their knowledge if they can. Always go to the top for advice and make sure you have a list of questions that are key to your concerns. There are absolutely no guarantees that following someone else’s method with work for you as well but you can create your own plan based on this advice and shape it into something that makes sense for you and your style.

2. How did you grow the business? What was your best investment?

There is no trick or gimmick to growing a business. It is tons of hard work, late nights, and lost weekends. However when you set a goal it is much easier to push through those early years knowing that you will be able to have the lifestyle you want eventually. There are a lot of tools to help you now, such as social media and Facebook advertising which has a proven return on investment for most businesses. Google Ads is another. How you chose to spend your budget needs to closely align with your customer demographic though or you may as well just go throw that money in the bin. So be aware of that in any marketing spend. Finding out exactly who your customer is would be the best startup investment you will ever make as you can shape every decision with that knowledge.

My best investment has been self-education. Reading as much as I can, listening to the experts, sharing that information with my clients and customers through marketing.

People want to know what’s in it for them, how your product or service will benefit them. If you can clearly articulate that, you will be way ahead of the game.

3. Looking back to when you first started Bella Management, is there anything you’d change when you were in the start-up phase?

I often say money. I wish I had have had more start up funds. Saying that however I learned so much from doing it rough. I have such gratitude for my financial success now and really appreciate simple things like I haven’t had to worry about paying a utility bill or phone bill for years. That alone was such a juggle for so long. Being able to go and buy groceries I want rather than what I can afford. I can buy fresh salmon every single day for dinner! Those things still feel like little miracles even though its been a long time since I’ve had those worries.

4. Top 3 tips to getting started? I have the skills but struggle with the confidence of going out on my own, especially in this climate.

Oh boy, what a question in 2020… Okay, so I think these are my top 3 in all times, and I survived and thrived through the last global economic crisis so I must have something right I guess.

1. No never ever means no. No just means give me a better idea. Maybe the timing isn’t quite right, try again, soon. Persist and dig deeper into what your client really needs from you. What problem can you solve for them?

2. When you don’t know what to do, do nothing. This is something my Nana used to say to me. I’m quite high energy and if things are moving too slowly for me I can try to force them forward. I’ve learned (and it’s still against my nature) to be still. Wait for that idea or resolution to come to me organically. Feel it, roll it around in my head and my heart. Look at the worst and best case outcomes to see if I’m comfortable with both ends of that spectrum. Learning this skill has helped me avoid many mistakes but also its helped me to move very quickly on decisions as I’ve learned to trust my instincts rather than make panicked emotional decisions from anger or fear.

3. There is never a right time to open a business. Even in the best of markets it’s a risk. Start small, be cautious of overspending on things you really don’t need. I started my first business and went out and got a gorgeous office space, lovely furniture etc… and the GST came in the following year and wreaked havoc on our industry. If I had have not overspent on those things I would have seen it through, but I had to sell out and go and work for the new owner. This time I started from a second hand computer in my bedroom and worked from home doing appointments out at cafes until I had two years of trading and solid reliable profit before I leased office space and hired staff. I still spent a few years paying $10 for instant cheque clearance! So keep it tight, keep it agile, don’t waste a cent.

5. At what point did you know it was time to take your career to the next level? I feel like I am stuck, my business is successful but I don’t want to plateau now, I want to grow.

Take it there! What’s stopping you? Add a product, add a service, find out which clients or customers you are not reaching and why… Go find them. I’ve found that I have to constantly adjust and adapt to the demands of my industry and, just the world around us, really. There is a quote I read and loved. ‘It is better to create something that others criticise than do nothing and criticise others.’ I believe wholeheartedly that ideas create ideas, work creates work…. Jump in with both feet and don’t hold anything back!

6. Did you test your ideas with the market before launching? If so, what was the concept test approach you took?

No I don’t test, I research what interests me and I figure that I can’t be the only one that feels that way or thinks like I do. I don’t worry about what people think of me personally, you can’t please everyone. I think that once you know that some people will misunderstand you no matter what you do or say, it frees you up to try anything. I don’t look at what my so-called competitors do. What’s the point? If they come up with something I haven’t thought of, good on them! I can only do what I can do to the best of my ability.

Everyone thought I was stark raving mad opening an agency that specialises in diversity and inclusion. Nearly 20 years later I’ve had press refer to me as a ‘thought leader’ and ‘before my time’. So your ideas are valid and there is an audience for them. The important thing is to find out how best to communicate your ideas to your clients.

7. Have you ever struggled with procrastination as a result of feeling overwhelmed or imposter syndrome? How do you get through it?

I’m not good a procrastination, things just have to get done whether you like it or not, right? Some days I do not want to be an adult or a CEO. Some days the decisions I must make feel so hard and heavy I nearly buckle under the load. That’s life though isn’t it? Everyone has those days and I think that’s important to remember. No one knows what they are doing all the time, no one has a magic ball to predict the outcome. When I feel overwhelmed I go for a walk with my dog and remember I am human and doing the very best I can that day. That is all I can do.

Imposter syndrome doesn’t hit me at work, I am very confident in my skill set. I get it in my personal life. Because of what I do for work, people often think I’m a bit fancy but I am absolutely not. I really dislike glossy bars, any outfit that requires boob tape and anything to do with gossip. So I feel like that can throw people and I’m really uncomfortable in those settings. I’m happiest fishing with my dog and cooking for friends at home or having a BBQ on the back of my boat while watching the kids swim around and sharing a G&T with my best friend talking about life.

If you’ve ever watched Frankie and Grace…. I’m Frankie and she’s Grace!

8. What do you know now, that you wish you had known when you started? What would you tell your younger self?

Honestly, this one gets me every time. I don’t know that I would tell her too much actually because then I would have missed out on so many opportunities to learn. Also, ignorance is bliss most of the time. If I knew how hard it was going to be I might never have started!

9. Where do you get your inspiration from?

Women. My female friends, family and colleagues inspire me every day, we are so incredible. My sole desire in life is to make sure every women knows her full worth and owns her power.

10. Did you pivot your business through COVID?

So many things. It will all be going in my next book, but some key decisions and implementations were mostly designed to help our clients get through this. We started virtual wholesale showings for fashion distributors, we helped clients get products to COVID-safe studios so they could keep up with sale and content marketing. We created Facebook videos for clients to help them with targeted sales revenue. We ramped up our content creators and digital talent management so clients could use more models for social media collaborations and many more adjustments. One thing I finally did was record my audiobook Body Image Warrior and I just sold it to Wave sound last week, so that is super exciting!

11. Who do you admire in business?

I mean come on now, Fleur Madden the CEO of Freelancing Gems is one of the most incredible women I have the privilege to know. We met many many years ago now and her work and story is such an inspiration for all of us. A total boss in all ways as a human being and a total lady doing it!

About the Entrepreneur in Residence: Chelsea Bonner

You can find out more about Chelsea and our Entrepreneur in Residence program, included in the Ruby and Emerald memberships, via this page.