We’re excited to introduce you to the always interesting and insightful Anna Osgoodby. We hope you’ll enjoy our conversation with Anna below.

Anna, appreciate you joining us today. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

I have so many answers for this question! At the end of 2020, I actually went through the process of starting over in a lot of ways. So this is a question I pondered a lot during that time. Previous to owning Going Bold Studio, I owned another business and after running that company for 5+ years, my business partner decided to take her career in another direction. After weighing my options, I ended up walking away from a buy-out deal and decided to launch a new company from the ground up. It was a scary decision at the time, especially because we were still in the middle of a worldwide pandemic, but I went for it anyway! With that decision, here are some of the things I focused on that helped jumpstart the growth of my new company and things I’d recommend to others starting out.
Launch sooner rather than later
Planning and creating a business strategy is great (and very valuable, especially further into your business) but it is not the end-all be-all. Progress really is better than perfection when it comes to starting a business. Oftentimes, so many of us have great ideas for our businesses but they stay as ideas because we never actually go after them. We spend weeks, months, and years thinking about our businesses and planning everything out without actually doing anything. Skip this mentality! Get your website up, tell people about the services you offer, get out there! You can always adjust your website, you can always tweak your pricing or packages, but you won’t get far if you don’t take that first step.

Network, network, network!
On social media, in-person or in Zoom meetings… Networking is gold! Get out there, give advice to others, and let them know about your business. It’s definitely a long-term strategy but it’s a strategy that can keep giving years down the road. Some of my favorite ways to network are through local business groups in my city, on Facebook groups and on Instagram. It can be time-consuming, but it’s a strategy that has been really helpful to me.

Another aspect of this is connecting with the people you already know! This may sound simple but make sure the people in your circles know that you started a business and what you offer. I get it, sometimes it can feel scarier putting yourself out there to people you already know… but you already know them! Referrals carry a lot of klout so it’s worth telling others about your business and sharing about it on social media! I can’t tell you how many friends or acquaintances have referred me clients from casual conversations they’ve had with others where a service I offer came up. People can’t refer you clients if they don’t know what you do… so get out there, talk about what you do, share your work and make it a habit of doing it regularly.

Focus on building your portfolio and gathering client testimonials.
This piece of advice is really geared towards those who are service providers. I work in the design and marketing industry and while it’s great to tell people what you can do, showing them will always have a bigger impact. That means building out your portfolio and gathering client reviews so that you can showcase that work to potential clients.

Just starting out? This is one time in your career where it may be worth doing work at a discounted rate or helping out friends and family to build out your portfolio. If that isn’t an option, you can also create concept projects that aren’t actually client work, but showcase different types of projects you’d like to work on – either for made up clients or well-established brands. Of course, if you do end up doing concept work, make sure you are honest that they are concept projects in your case studies. The key here is to get your feet wet and have examples of your work to showcase when you are pitching new clients.

Only Invest in Necessities at the Beginning
Overhead can add up really fast! And while there are certainly awesome tools and courses out there that are 100% worth investing in, when you’re getting started I recommend keeping expenses as low as possible. Everywhere we go we’re told we need this or that, but the truth is sometimes all you need to get started is to… get started. Get scrappy, focus on the essentials you need now and save some of those investments for later when you’re a little further in your business journey.

Focus on what YOU are most passionate about
Following up on always being told we need different products or services… when you start a business there will be so many voices out there telling you what you need to do to be successful. You have to sell courses… you have to have a membership… do this, do that! Now don’t get me wrong, there’s a lot of great advice out there, but it’s also important to remember business is not one size fits all. Instead of chasing trends, spend time thinking about the services and products you want to offer because you’re passionate about them!

Anna, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m Anna Osgoodby and I’m the founder of Going Bold Studio where I help small business owners with branding, Squarespace web design and social media campaigns.
I got my start in the social media industry 13 years ago after graduating from college and soon after made a cross-country move to New York City. There, I worked at a lifestyle PR agency and furthered my career and interest in marketing and design. Then in 2015, I decided to branch out on my own and launched my first business. At the time, I really wanted to be able to split my time between NYC and the PNW, where my family lived and being an entrepreneur gave me that flexibility. A few years after that, I’d later go on to move back to the Seattle area and launch my current company Going Bold Studio.

I specialize in working with entrepreneurs and small business owners and have become known for my bright and colorful style when it comes to my design projects. I really love working with small business owners because I love getting to be a small part of helping them chase their dreams. Truly there is nothing that lights me up quite like the energy of helping others and I really put my heart into all of my work. Because I offer design and marketing services, I’m also able to serve my clients through different needs which is something that I love!

What do you think helped you build your reputation within your market?

I wholeheartedly believe being yourself is one of the best ways to build credibility and connect with your ideal clients. That may sound simple, but in today’s world, there are so many people who are trying to emulate others. The true magic happens when you fully embrace yourself and let that shine. For me, I happen to be high-energy, bubbly, and girly. I know my style or personality isn’t everyone’s cup of tea, but at the same time, showing up as my authentic self on my website and social media accounts has been instrumental in attracting the clients that I want to work with. The clients whose energy matches mine, that have similar aesthetics, and people who I also have shared interests with beyond our businesses.

Have you ever had to pivot?

I’ve had to pivot so many different times and anticipate many pivots in my future too! One example is when the pandemic really started to hit, my business was really affected. I went from one week having a call with my accountant assuring her that things looked pretty good, to losing 80% of my monthly business within a few weeks. It was scary. Offering social media and design services are often considered “extra expenses” so a lot of my clients needed to take things in-house for the time being because they were being hit hard financially too. One thing that I did at that time was pivot to offering educational workshops to other business owners. Which I totally understood, but of course it also had an impact on my business too. One thing I did was launch a workshop on social media engagement strategies. It was only about an hour and a half but it was focused on giving business owners the strategies they needed to make progress on their social media accounts and fast!

Another thing that happened was I noticed a lot of people within the marketing industry being let go from their jobs or laid off. Again, back to marketing/design being one of the first things on the chopping block! While I know it was a scary time for so many, I realized a lot of people were going from being a social media manager at a company to wanting to start their own social media companies. So I rolled up my sleeves and created a workshop specifically for people who wanted to launch their own social media companies. These were two products I never thought I’d offer but pivoting is all about paying attention to the moment and doing what makes the most sense!

Contact Info:

• Website: https://goingboldstudio.com/
• Instagram: https://www.instagram.com/goingboldstudio/
• Facebook: https://www.facebook.com/goingboldstudio
• Linkedin: https://www.linkedin.com/in/annaosgoodby/
• Other: https://www.tiktok.com/@goingboldstudio

Image Credits
Headshot photo credit: Caitlyn Lunsford https://www.caitlynlunsford.com/