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Serial entrepreneur Emma Grede & supermodel Ashley Graham on turning a side hustle into a full-time gig

·3 min read

You are the greatest secret to your success.

That’s the key message Co-Founder & CEO of Good American and Founding Partner of SKIMS, Emma Grede, and supermodel and entrepreneur Ashley Graham, who have years of experience starting businesses and growing brands.

The two hosts of Roku’s “Side Hustlers”, produced by Candle Media's Hello Sunshine, caught up with Jack Howard, Ally’s Head of Money Wellness, to share tips on how to turn a side gig into a full-time career.

What's step one for someone who wants to venture out and start a side hustle?

Graham: Make sure you’re passionate about it. It will take everything out of you and will be very hard at times – if you aren’t passionate, you won’t be successful.

Grede: I agree with Ashley wholeheartedly, so much of what can hold you back is what is happening in your head. Don’t let fear get in your way. Get really comfortable with, and accept, that element of risk that’s there, but don’t let it make you fearful.

What mistakes do you think side hustlers or women entrepreneurs may make to keep them from getting to that goal?

Graham: If I’m not a little bit fearful going into something new, then I know I'm not really excited about it. The discomfort energizes me to come in more prepared and you need that grit.

Grede: There are going to be mistakes when you start a business. We have to get comfortable with making mistakes. If you're not making mistakes, you're not doing enough. You’re in constant conversation with yourself, and your mindset matters, believe in yourself. That self-belief is something that is going to take you somewhere, but you've got to truly believe it.

How do you differentiate yourself from competitors?

Graham: You have to understand how to roll up your sleeves and get things done. It doesn't have to be pretty, and it doesn't have to be perfect, and there's no one right way to do anything. Once you get around that, and like Emma said, all the things going on in your head, put that to the side and know you were here to do this! If one of your big ideas along the way doesn’t work, don’t let that be something that takes you down. Use the learnings to find a different path forward.

Grede: You have to find what you do uniquely. There’s a finite amount of new ideas – find how you can differentiate yourself through innovation. Finding your unique proposition is important, and then lean in wholeheartedly.

What are some things – financially – that you've got to have down and aligned before you can advance in your side hustle?

Grede: You've got to understand the finances of your business intimately – inside out – as well as the data and the metrics. You have to be able to read the patterns in the numbers and understand what they mean in six months, 12 months, three years... five years. Many think sales and marketing come first and finance is what happens at the end – finance is what needs to happen first and it keeps your business alive.

Graham: Whether you are a numbers person or not, surround yourself with people that are better than you at it, and then ask them questions so you start learning more and more. It’s OK to not know or understand, it’s not OK to not ask the questions for yourself. Financial literacy is something that is so empowering.

How can having a side hustle be a game changer for women?

Graham: First – just being able to do what you want to do for yourself is a game changer. But even more, women are really wanting to invest in other female-founded businesses. They want to be a part of things and shape the future of female entrepreneurs. It is very much an opportunity to have women supporting women, and they do.

Grede: Starting your own business is not going to be easier than working for someone else. You have to go into it with your eyes open. You also find amazing parts of yourself. You explore and learn a lot about who you are and what you're supposed to be doing - where your strengths are. And this is hard for women, but you have to put yourself first. It’s not about being selfish, putting yourself first lets you think about all the things ahead of you.

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Headshot of Jack Howard, head of money wellness at Ally Financial
Jack Howard
Head of Money Wellness, Ally Financial