An Interview with Bold & Pop Co-Founders Anna Osgoodby & Mallory Musante

Anna Osgoodby & Mallory Musante of Bold and Pop

Anna Osgoodby & Mallory Musante of Bold and Pop

Names: Anna Osgoodby & Mallory Musante
Location: 
Raleigh, NC & Seattle, WA
Business Name: 
Bold & Pop
Established:
2015

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WHAT IS YOUR BUSINESS?

We are Anna Osgoodby and Mallory Musante and we’re the Co-founders and biz besties behind Bold & Pop. Together we help fellow business owners with their branding, Squarespace website design, and social media campaigns. At our business, our focus is really to take these pieces off a creative entrepreneur’s plate so they can focus on what they’re really good at and passionate about

WHAT INSPIRED YOU TO START YOUR OWN BUSINESS?

Something we were both really big on when we started our business was having more flexibility. One of the big hang-ups, when we were job hunting, was that we wanted more flexibility in our schedules and in our locations. At the time, Mallory was living in Connecticut and Anna in New York and being tied to an office with 2 weeks of vacation every year wasn’t going to cut it. Anna really wanted a job that allowed her to be bicoastal to spend more time with family and Mallory wanted the option to be able to travel more. Since launching our business, both of us have moved — Mallory to North Carolina and Anna back to Washington so having an online business was really key to making these changes easier.

WHY DID YOU CHOOSE YOUR INDUSTRY OR NICHE?

Since we already worked in the industry, it was a pretty seamless transition. We had both been working in social media together for years but also had branding and design skills that we were itching to use further so we decided to include those in our offerings. Now we really get the best of both worlds being able to help our clients develop their branding and logo design, create a website that represents their business and then help them reach their target audiences via social media.

DO YOU DO THIS FULL TIME? IF YES, WHAT DID YOU DO BEFORE THIS? IF NO, WHAT ELSE DO YOU DO?

Yes, we are both full-time with Bold & Pop! Prior to this, we both worked at a public relations agency in New York City so we’ve both been in the industry for 10+ years each.

DID YOU GO TO COLLEGE? IF SO, WHAT DID YOU STUDY?

We both did! Anna went to the University of Oregon and studied journalism and public relations and Mallory went to Bryant University and studied marketing.

HAVE YOU ALWAYS WANTED TO BE AN ENTREPRENEUR? WHY OR WHY NOT?

Anna (A): No! In fact, I really never had any desire to start a business of my own. I’ve always liked the team aspect and starting a business just wasn’t really something on my radar. Everything kind of came into place though and when I brought up the idea casually with Mallory one day and she was like, “we should do this” suddenly everything clicked and I had a lightbulb moment of, “oh hey, we reallyyyy could do this!”.

Mallory (M): Bold & Pop is actually the third company I’ve started but up until my sophomore year of college, I thought I’d work in corporate America. That was the year my first business idea came to me, a shoe design business. While neither of my other businesses worked out, they provided invaluable experience for Bold & Pop!

WHAT ARE SOME OF THE BIGGEST LESSONS YOU’VE LEARNED SINCE STARTING YOUR BUSINESS?

Blazing your own path is a big one! We’ve always really set out to do our own thing and that has been so important to our success. Now that we’ve been in business for several years though we’ve watched so many people start and leave businesses that didn’t work because they were trying to follow business trends. If you really want to find success it’s all about trial and error and finding who your audience is and what they need. Following someone else’s path or building your business around business trends just isn’t a sustainable model long-term. That goes along with the lesson that you really need to be adaptable. We don’t think there’s one point where you just reach and suddenly have everything figured out. It’s a process and you need to embrace that whole-heartedly year after year.

WHAT HAS SURPRISED YOU THE MOST ABOUT ENTREPRENEURSHIP?

A: How much the process truly changes you. Going in, I knew it would be an adjustment but it has heightened my self-awareness SO much more than I thought. It's really driving me to focus on self-development and being the best version of myself, which is AMAZING! I didn’t realize how it would affect my personal life too though. When you decide to focus on improving yourself and really go after your goals it can be all-consuming and one day you may look up and realize that things you thought you wanted before don’t align anymore. Not only that, but you may realize that it’s not as easy to connect with people in your life who aren’t on a similar journey. It’s definitely a fork in the road kind of change that is truly transformative and hits every part of your life.

M: In all honesty, I think it’s the way people respond to me when I say I have my own business. I’d always assumed people would be excited for me but that’s not always the case. I’m pretty much always surprised by their response. Either it’s a flurry of questions about Bold & Pop, the ever so frustrating “that’s cute”, unsolicited advice, or excitement. It’s always interesting and I’ve had to learn to not care what people think. It’s my journey, not theirs. I’m proud of all we’ve accomplished and I wouldn’t trade this for a 9-to-5 for all the money in the world!

WHAT IS ONE PIECE OF ADVICE YOU’D GIVE TO ASPIRING ENTREPRENEURS?

A: Plan ahead if you can! I think there is such a trend to “quit your corporate job and follow your passions” and don’t get me wrong, I freaking LOVE that. I want people to chase their dreams and make all of the things happen, but I also think people think it’s a lot easier than it is. People see these “make 6-figures in 6-months” and “replace your corporate income in 3-months” headlines and think, “oh, I’m going to do this and I’m going to do it fast!” and I’m not saying that’s not possible but I think it’s much more the exception than the rule. My advice is if you have the option to save up prior to starting your business, DO it! Work on your business as a side-hustle for a while, get your systems in order and then go full-time. Starting a business is a crazy, exciting, amazing thing to do but it’s also stressful, so if you can alleviate some of that stress by knowing your bills are going to be covered for 6-months, even if you make nothing during that time, then I highlight recommend it.

M: It takes patience and persistence. Nothing is going to happen overnight… No matter how many people look like they’ve “made” it overnight. There will be delays, challenges, and you’re going to have to pivot as you start/grow. But persistence is going to get you to where you want to go and beyond. It’s a balance of being patient as things unfold as well as continuing to push forward and do the necessary work you need to do. I truly believe this combination is the key to growing a successful brand.

HOW DO YOU DEAL WITH SETBACKS AND IMPOSTER SYNDROME?

A: There will always be setbacks and I think at the beginning I struggled with this more. These days, I really try not to dwell on things too much. Business is such a journey and if something doesn’t work or if there’s something that can be done better next time when we take note of that. We’re always focused on the future and improving and less on spending too much time bummed out about what’s going wrong. It’s truly a mindset thing. As for imposter syndrome, I think the best thing you can do is keep putting yourself out there. Keep doing hard things and keep doing things that scare you because the more you do those things and survive (which you will) the more you prove to yourself that your credentials and experience is valuable.

M: Over the last few years, I’ve worked a lot on having a positive mindset. I think this has truly helped with setbacks and given me the confidence to overcome the feeling of being an imposter. I also know that pretty much everything is “figure-out-able” so if I’m doubting myself in the moment, I take a step away to center myself (take a walk, a few deep breaths, or tackle an easier tasks). Then when I come back, I get to work. I know I can find a solution no matter what. It also helps that I have Anna’s brain too and that we help encourage each other no matter what!

WHAT DO YOU LOVE THE MOST ABOUT BEING A CREATIVE ENTREPRENEUR AND DOING WHAT YOU DO?

A: I love what we do because there’s always a new challenge to come up with solutions for. Because we work in both social media and the design industry there’s a lot of variety in projects and what those solutions are too, which is exciting.

M: I think my absolute favorite part is helping others build their brands so they can live their dream life just like I am!

IF YOU WEREN’T A CREATIVE ENTREPRENEUR, WHAT WOULD YOU BE DOING?

A: I always said if I didn’t take the path of going into marketing and design, I would want to be a career coach or counselor. Growing up I was always planning my class schedule and my friends and loveee that so I could see myself doing something like that. Another path of helping others hit their goals! Clearly, you can start to see a pattern of what means the most to me!

M: My career path has always been in marketing so I’m sure I’d still be working in that capacity to some extent. Maybe in a non-profit or another area where I feel like I’m really making a difference!

WHAT DOES SUCCESS MEAN TO YOU?

In one word…impact! We think being successful is a lot more than just making money. It’s about having an impact on the people you are working with. Our business is very personal and being apart of our client's journeys is so important to us! Having them look back and tell us what a difference we made in their business, THAT is true success to us.

WHAT IS YOUR WHY?

Our why started with us both wanting more freedom. Freedom to travel, to spend more time with family, financial freedom…you name it, we wanted it. But since then, it’s grown into so much more. We’re truly passionate about helping other small businesses accomplish their goals as we have ours. We realized we could provide a more personalized and impactful experience on our own rather than through the agency we worked at previously. We truly want to share our skills and expertise with others to empower and support them along their business journey.

IMAGINE IT’S A YEAR FROM NOW AND YOU’RE CELEBRATING WHAT A GREAT YEAR IT WAS FOR YOUR BUSINESS. WHAT WOULD YOU HAVE ACHIEVED?

We’ve set some really big goals for ourselves in 2019 with a high growth rate and we have no doubt that we’re going to crush them. In a year, we’ll be celebrating our biggest year to date in terms of profit and most importantly, we’ll be celebrating the massive growth of our community. The more we grow, the more we try and give back and our goals are all really intertwined with that.

WHO IS YOUR ROLE MODEL/WHO DO YOU LOOK TO FOR INSPIRATION AND WHY?

A: I’m really inspired by other super powerful women in the industry carving out success for themselves. A few people who have inspired me over the years have been Lauren Hooker of Elle & Company, Melyssa Griffin, Sophia Amoruso, Rachel Hollis, and Jenna Kutcher!

M: Not business related but my parents are 150% my roles models and who I look to for inspiration. They’ve taught me so much about working hard, helping others, and living a life with integrity. All of this really bleeds into our business and who I am as a business owner and I wouldn’t change the lessons and values they’ve instilled in me for anything!

WHO HAVE BEEN THREE OF THE BIGGEST SUPPORTERS ON YOUR BUSINESS JOURNEY?

A: I’d say Mallory, my parents (double-whammy), and Kathy who has been a second mom to me. They all support me in different ways and I couldn’t do what we do without them!

M: Obviously Anna, my parents, and three of my closest friends. No matter what’s going on, I know I can turn to them for support, whether it’s talking an idea through, complaining about a difficult day, or even a little humble brag! They’re always happy to listen, offer congratulations or words of encouragement when I need it most.

WHEN YOU’RE NOT WORKING, WHAT DO YOU LIKE TO DO?

A: So many things! I moved back to the PNW about a year ago after living in New York City for almost a decade and cannot get enough of all things outdoors. I love hiking, checking out new parks, kayaking and I even joined a community garden. So many adventures to be had! I also love checking out new restaurants and local breweries — literally so PNW lol.

M: You’ll either find me bouldering at the local rock climbing gym, out hiking, snuggling with my dog, or exploring new restaurants or shops with my friends. I’m not the type of person that can easily shut my brain off to relax (I usually open my laptop if I’m just sitting around my apartment which is a habit I’m working on breaking!) so I usually try to fill my free time with activities that I truly enjoy and will really help me feel refreshed.

WOULD YOU DESCRIBE YOURSELF AS AN INTROVERT OR AN EXTROVERT? HOW DO YOU THINK THAT IMPACTS YOUR BUSINESS?

A: I think I’m somewhere smack-dab in the middle. In general, I’m probably more introverted. It takes a lot for me to put myself out there at networking events and I very much need my own time to regroup and feel rested. In my group of friends, I’m very much one of the louder people who is always chatting it up and introducing friends to other people I know though, which tends to be more extroverted. In terms of affecting our business, I think having a balance is good because I can really adapt to other people’s energy and my appropriate response.

M: I am definitely an introvert. I love my alone time and really need it to feel rested. Luckily, I don’t think it affects our business much honestly. Anna and I really balance each other well and we are always looking for ways to play to our strengths as business owners. For example, neither of us loves in-person networking, so we do a TON of networking online. Finding what works best for us and going for it has been huge in growing our business!

WHEN DO YOU FEEL THE MOST PRODUCTIVE? ARE YOU AN EARLY BIRD OR A NIGHT OWL?

A: Good question! In life, I’m much more of a night owl (which is a problem now that I have to get up super early—west coast living on an east coast schedule is rough) but I think in general I’m just most productive when I have a regular schedule. We try and stick by standard hours 9-5:30 pm EST and by doing so we have our dedicated work hours and more importantly an end time for working. As entrepreneurs, there’s always something you could be doing and working non-stop is actually the killer of productivity. We’ve found we’re much more creative and productive when we shut our brains off and give ourselves adequate rest.

M: I’m a newly converted morning person! I used to work late into the night but recently changed up my routine to go to the gym in the morning. This means I get home at least an hour before we start our workday. This gives me time to relax, catch up on chores, or get a head start on work if needed. Like Anna mentioned, we do try to stick to our scheduled hours but I typically save things I really need to focus on for that morning time where I have absolutely no distractions.

DO YOU HAVE TIPS FOR STAYING PRODUCTIVE WHILE WORKING FROM HOME?

A: I’m big about prepping the night before. If my office gets messy from the day I like to make sure everything is in its place before going to bed. Cluttered workspaces drive me bonkers and can affect my focus so I like to make sure everything is cleaned up so I’m ready to roll each day. Another thing I do is actually put real clothes on. It can be easy to work in your PJs at home and while there’s nothing wrong with that, getting dressed definitely helps with my mindset and overall productivity.

M: I think setting boundaries and expectations with others that you have a set work schedule that you stick to has helped me the most with staying productive. While I can actually set my own schedule and technically can grab lunch or coffee with someone if I want, I find that I’m much less productive when I have things like that scheduled during the day. Now I ask if people can meet at night or on the weekends so I can keep my productivity high during our actual work hours.

A FEW OF YOUR FAVORITE THINGS

WHAT IS A BUSINESS TOOL YOU CAN’T LIVE WITHOUT?

Google Drive and Asana! (Well, and Adobe design products and Squarespace for industry-specific tools.) Collaborative tools like these make our lives so much easier—especially running a business bicoastally.

This is going to sound funny because it’s really not that expensive but Asana was one of the first big investments we made in our business and it’s worth every dollar of the almost $40 a month it is. We were a little hesitant to jump on the digital calendar/to-do list because we’re old-school about our planners but it was one of the best things we did for our business. It’s made us much more efficient, streamlined our processes and has helped keep us more organization with shared tasks.

WHAT IS YOUR FAVORITE INSPIRATIONAL QUOTE OR AFFIRMATION?

A: I really love the quote “hustle and heart will set you apart” because I think in crowded markets, showing your personality and how passionate and excited you are about your work truly does set you apart. People want to work with people they connect with so I think putting both together is really important.

M: “Be a fruitloop in a world full of cheerios.” Like Anna said, it’s easy to get lost in oversaturated markets. I love being able to show off our personalities and be truly unique in who we are as individuals and business owners. It helps us connect with our target audience on such an authentic level and hey, no one ever said business couldn’t be fun and we take that to heart!

DO YOU HAVE A FAVORITE PODCAST?

We are both huge fans of Kacia Fitzgerald’s podcast, EmpowerHER! Anna is also a podcast junkie and loves How I Built This, Jenna Kutcher’s Goal Digger, Rachel Hollis’ Rise Podcast and then the Hollis company’s Rise Together which is just a great one for personal relationships too.

WHAT IS YOUR FAVORITE BUSINESS OR PERSONAL DEVELOPMENT BOOK?

Yessss, some favorites are Rachel Hollis, “Girl, Wash Your Face”, Jen Sincero, “You are a Badass”, Sophia Amouruso, “Girl Boss” and Gretchen Rubin, “The Four Tendencies”.

DO YOU HAVE A FAVORITE BLOG?

We don’t have one particular blog that we follow religiously but we do love to scroll through Pinterest and read anything that stands out to us. We’re also constantly Googling different things we want to learn more about and signing up for webinars. Anything we can consume from a number of different people!


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By Katie Jenison

Katie Jenison is a freelance writer offering copywriting, blogging, and ghostwriting services. She works closely with home builders, remodelers, interior designers, real estate and property management professionals to help them create content marketing strategies, improve their digital presence, generate leads, and engage with their target audience. Katie also helps freelance writers and creative entrepreneurs pursue their dreams of working from home by providing tips and advice, business strategies, and writing tips on her blog, The Quiet Type. Download her free workbook, A Freelancer’s Guide to Setting Rates, here.

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