Bold & Pop : #RealTalk Q&A with Bold & Pop Co-founders on First Two Years as Full-time Biz Owners

Guys, we just hit another milestone in our biz and we are PUMPED up! 🎉🎉 As of this week, we've both officially hit our two-year anniversaries of going full-time with Bold & Pop! Mallory's biz boss anniversary was in November and Anna's was just this week in December! Making the jump from a dream or side hustle to going full-time is such an exciting experience and we'd be lying if we said we're not totally sentimental about this anniversary! Eeeee! 2 years baby!

To celebrate, we wanted to do a post highlighting some of the key lessons we've learned along the way -- good and bad. Even better, we wanted to hear from YOU! We are so thankful that we get to live out our dreams each and every day and supporting our community of fellow biz owners, bloggers, side hustlers, and dreamers is SO dang important to us. Because hey, we're all in this together so better to learn from each other's experiences right?! So we did just that. So shout-out to all of those who sent over ideas and voted in our #BoldBossTribe Facebook group and on Instagram! So let's get down to it.. it's time for some #RealTalk! (BTW, A is Anna and M is Mallory! 👯)

What are you most proud of achieving in your first two years?

A: Honestly, the first thing I'm proud of? Making it through the first two years! There are so many businesses that don't even make it that far, so to hit that milestone really means a lot. We were always determined that we'd figure things out, but you never realllyyy know how things will turn out until you go for it! Along with that point, I'm just really proud of our determination and the partnership that Mallory and I have. Building a biz is hard freaking work and I am so proud of how far we've come both professionally and personally. It's been quite the journey and I love the positivity we try to bring to each day no matter what is on our to-do lists.

M: To be totally honest, I'm most proud of the fact that we're able to make enough money for us both to be full time. I had two previous businesses and neither were even close to making enough money for me to quit my 9-to-5. Not only is this financially satisfying for us but it also shows the impact we've been able to make for countless other businesses with our skills and experience. And that's always our goal for clients and our community... to help them get to a point where they can quit their 9-to-5 (if they haven't already) then grow well beyond that! 

How did you land your first clients?

A: Our first freelance client was actually from a casual introduction at a friend's birthday party. At the time we met, the idea of freelancing hadn't even crossed my mind. When she reached out a few months later to see if I might be interested though, I jumped on the opportunity. We started out by helping her agency with one client and then that quickly grew to several more projects. Even though we'd both been working in the industry for years, there was something about our first clients that made this dream less of a dream and more of a reality check that.. oh hey, yeah we could really do this.

How did you know it was time to go full-time with your business?

A & M: Well, if you aren't familiar with our story, this decision was more of a push than hitting that magical milestone knowing "it was time". After working at our previous agency for years, it was made pretty clear that our department wasn't valued and that our jobs were on the line. I'll spare you some of the details, but the truth is the situation had become pretty toxic. So when news was given that Mallory was going to be laid off, I put in my notice as well. Sometimes that "perfect timing" is masked by a kick in the booty and it was just the kick we needed to take the jump and give Bold & Pop our all.

Bold & Pop : #RealTalk Q&A with Bold & Pop Co-founders on First Two Years as Full-time Biz Owners

What has been most effective in your own marketing strategy?

A: I'd say the first thing has been our branding. From the very start, we wanted Bold & Pop to reflect our personalities so we focused on bright and happy colors, with a casual and conversational tone of voice. We wanted our business to be fun (like us! Or so we think lol) and we wanted our branding to give people a look at what it would be like to work with us. We had a really streamlined target audience and we wanted to make sure we were appealing to them right away, and carry that vibe across all of our channels -- website, blog, and social media. When clients come to us for branding or social media projects, it's the single-most thing I get comments on too. How they love how approachable and fun we've made our brand and how they want that experience to translate for their own businesses with their style. There truly is no better way to market your own services than showing others your work and that you really "get it".

Second, I'd say our blog has been so important to our marketing strategy -- specifically content marketing. We publish fresh content each week and the platform gives us space to share our expertise and journey with our community (like you!). It's probably one of the most time-consuming aspects of our marketing, but we've always been really focused on bringing quality to our community and this is where we're able to shine! It has been really important to our business too because it's how a lot of people find out about us! Whether they end up on our blog from a post in a Facebook group, start reading from Instagram or click through on Pinterest. It's a driving force for our social media content and something that has been really fundamental to our marketing.

M: If you've been following us for a while you've noticed a transition from us hiding behind the brand to finally putting ourselves out there for y'all to see! This has been such a game changer for us. It's given us the opportunity to authentically connect with our community and clients that we weren't necessarily doing at first. Everything from adding photos of us to our About page and email signatures to actually showing our faces on Instagram stories. We've really put a lot of effort into that this year and it has been insanely beneficial putting a face(s) behind the brand and connecting with others. 

It's been a bit of an adjustment but for the most part this has also been pretty easy transition. Mainly because our brand is us and our branding has always reflected that as Anna mentioned above. What works for us might not necessarily work for someone else and vice versa so focusing on what we're good at and being authentic to ourselves has been key to our marketing success. 

What have been some of your top wins?

A: That is such a tough one because we have had so many small and big wins along the way! In terms of one that stands out as feeling like our business had really made it, I'd have to say it was when we signed $10k worth of projects within one week. That was a BIG moment and even more exciting, they were all projects that we were so excited to work on which made that success even better!

Something else I’m super proud of is the #BoldBossTribe! We originally came up with the idea after having a conversation with one of my friends who is a musician. It started as an idea to do a Q&A blog post featuring her talents and quickly grew into a week-long blog series to highlight other small biz owners, bloggers, and artists. We had such a blast with the series but afterward we let it sit on a shelf for about a year before having another idea. As our business has continued to grow we realized how much our community has meant to us and decided we wanted to make it a bigger part of our mission. So we decided to open up the blog series again and start highlighting other biz owners each week. From there, the momentum continued to grow and we decided to also launch a Facebook Group for our members to support each other. Who would have thought a random little idea could grow so much? Now we have over 500 members and it is truly one of my favorite parts of our business.

M: Along with everything Anna mentioned, attracting ideal clients is at the top for me! This might not really sound like a huge win but trust me, it is. This means all our marketing strategies and any adjustments we've made along the way have been effective and we've found our niche. And I know that that as the sky's the limit for us!

Plus, it's really, really fun to work with people you just vibe with! 

What have been some of your failures?

A: If there's one thing I've learned about owning your own business it's to pay attention and make changes when you need to. Luckily, Mallory and I are always working on fine-tuning our processes and making everything run as smooth as possible. One thing we struggled with in year two was going back and forth between feast and famine with clients. Our business would explode (like one of our wins!) and we'd have a ton of exciting projects to work on. Which is great, but because we'd be so busy working on those projects we'd find we didn't have time to consistently manage new business. So when those projects ended, we'd feel like we needed to scramble to sign more projects. Another issue we realized during this discovery was that keeping clients on their deadlines was making this situation worse. We'd have projects that were supposed to take 4-6 weeks that would end up getting delayed by clients, which made it really tough to start new projects.

So we paid attention and decided to make some changes to our systems to address some of the issues we were having. When I talk about changes, we reallyyy thought this out for how we could improve things and we took action, and I'm proud to say that, that failure turned out to be such a positive thing. Because it really forced us to improve what we thought was already a good process to be great. Plus, now that we've streamlined our processes, it's allowed us to plan projects out further in advance and help resolve the rollercoaster issue of client projects.

M: I don’t really look at anything as a failure since we learn A LOT from each situation we find ourselves in but I get where we’re going with this question ;)

If you’ve been following us you may have seen our launch of or signed up for the Bold Boss School Resource Library over the summer, a membership site with access to stock photos, social media graphics, branding elements, etc. We had some bigggg plans and worked our little butts off to launch this. Unfortunately, it was a less than impressive launch. Womp, womp. 

But we stuck with it… adding new resources every month for the members we did have. It quickly became a bit overwhelming trying to keep up with adding new, valuable resources every single month on top of our client work and our own work. We were really worried the quality would suffer and decided to take a step back, reevaluate the Resource Library, and come up with a game plan on how we could move forward to best serve our community without killing ourselves!

Bold & Pop : #RealTalk Q&A with Bold & Pop Co-founders on First Two Years as Full-time Biz Owners

What has been the hardest part of running a business?

A: One word, patience. It's never been one of my strong points to begin with and it's something I've really had to practice since starting Bold & Pop. We've always had such big dreams for our business and sometimes I tend to push the envelope on where we are in our journey. There's so much noise out there about being 6 and 7-figure businesses in your first 6 months, and traveling the world while you're working, and all of this jazz that just isn't everyone's reality. We have accomplished SO much already in our first years as a business and during some of those times when you're feeling less than impressed, I have to remind myself to be patient. Hard work DOES pay off, but it's important to also realize everything is a process and you won't achieve every goal you have overnight.

M: I’d definitely have to say being consistent with our marketing efforts. I’m guilty of getting so wrapped up in what I’m working on that I let our own work slide a little too much. Sometimes, I’m not nearly as active in Facebook groups as I normally am. I’m not engaging on social media like I should be. I have trouble developing creative content for us when my focus is on our clients. Doing ALL the things and wearing ALL the hats can be seriously hard…

What did you think you wouldn't like about owning your own business that you actually enjoy:

A: New business calls. I'm SO not a seller.. In fact, that was one of the things that scared the crap out of me about starting our own business. I'm still not sure I'd say I totallyyyy love them, and I certainly still get nervous sometimes. I LOVE the feeling I have after a call with a biz owner I really connect with though so I'd say that has definitely been surprising. I can't tell you how many times I've hung up with a potential client, dialed Mallory as fast as I can and then tell her about how me and so and so are officially new bffs and I can't wait to put a proposal together for them. 

M: Ditto 👆🏼

How have you managed growth and taking your business to the next level?

M: We are constantly evaluating what is working and what's isn't. Whether it's in our content strategy, on-boarding process or whatever it is, hopping on a call to talk it through has been key in developing new processes or focus to level up. 

For example, this past year we realized our on-boarding process for our web design projects was not serving us or our clients as well as it could have. Projects were dragging out much longer than their intended timeframe, which wasn't ideal for either party involved. So we knew we had to come up with a solution to be able to grow, which led us to look into a project management system and come up with a completely new on-boarding process. And I have to say.. so far, so good! 

Most of the time this starts with one of us mentioning something to the other that we think might need a little tweaking and then we're pretty much off to the races. We sometimes call each other to go over one little thing on a project and end up on the phone for 2 hours coming up with a solution to help us grow further. So not only is our consistent reflection and analysis of our business important in our growth but having each other as a sounding board has been essential to coming up with creative solutions to help take us to the next level. 

What is the biggest change from working a 9-5 to being an entrepreneur?

A: Hmm, there could be a lot of answers for this one. I think I'd have to say having to learn to put work down. We both came from an agency background, so we already trained to "be on" around the clock, but that got worse when we became biz owners. When you're working from home, it's so easy to just keeppppp working, because as a biz owner there is always something you could be doing. Truthfully, we were really bad the first year and a half we were working on Bold & Pop. When we first started, we still had day jobs so we were working on our biz for the rest of hours we were awake after work. Then when we went full-time, we were so busy trying to get our business off the ground that 12-15 hour days just became the norm. It wasn't until this summer that we really decided we needed to cut it out! We realized the only thing we were going to accomplish if we kept at this routine for another year was burn-out so we took a step back to give ourselves some rest. So it's been a long adjustment, but I'd definitely say learning to shut work down has been one of the biggest changes (and struggles!)

M: Since I've had a few other businesses before Bold & Pop, working long hours was already a norm for me (and I'm still VERY guilty of late nights and working on weekends on occasion...) But the biggest change in this particular industry is probably just managing every aspect of the business. We did a lot when working for another agency but add managing all our clients, responding to new business inquiries, writing proposals, updating our finances... you know, alllll the biz things... and WHOA! I mean I did that for my past companies but for whatever reason it seemed much more manageable (probably because they were product-based and B2C businesses so client relations didn't factor in). 

So getting used to handling everything has been a big change and adjustment for me. 

What are your favorite and not so favorite things about being an entrepreneur?

A: Favorite things.. Flexibility with my schedule! At first, this was the flexibility to visit my family for more than a few days. Now that I'm back in Washington, the travel part isn't as big of an issue -- although I do love being able to score deals on flights and fly whatever time I'd like. Just in general though, having that flexibility is a really nice option. I don't think we take advantage of it nearly as much as we should. Literally if one of us signs on 15 mins late in the morning we make ourselves feel guilty.. but it is a nice perk for when you have some things you need to take care of.

Not so favorite part? That's easy.. sorting our taxes and healthcare. In reality, paying quarterly taxes isn't all that bad, especially when you have an accountant to help you out, but it's just something I don't enjoy. I love learning everything I can and like knowing some of the ins and outs of things, and accounting and our tax laws are just confusing. I also could do without picking out health insurance.. Necessary and thankful we can at least sign up for plans, but also not my favorite.

M: I just really love being my own boss. Making my own schedule, calling the shots, being creative, working with clients... all of it! I might not have always wanted to be an entrepreneur but once I got the bug that's all I've ever wanted and I'm so grateful that I'm now a full-time business owner! 

I'd have to definitely agree with Anna on the not so favorite part... Taxes, healthcare and retirement planning are roughhhhh! I've never actually had healthcare or a retirement plan through an employer so I guess that's not a big difference but now that I'm getting older and am solely responsible for my income and these things seem to be a little more daunting. 

Bold & Pop : #RealTalk Q&A with Bold & Pop Co-founders on First Two Years as Full-time Biz Owners

What has changed the most for you from when you started your business to where you are now?

A: I knew starting a business was going to be an adventure professionally, but I had no idea the personal journey it would take me on. Becoming an entrepreneur can be really eye-opening and really forces you to evaluate what’s most important to you and the direction you want to head. It’s kind of like being enrolled in a personal development course on steroids. Being a business owner, you have to make so many decisions that can feel scary at times, but I think the more you make, the more you realize.. I can DO this! And I think that increased confidence gives you the courage to take chances in your personal life that you may have had reservations about before.

When we started Bold & Pop, a big motivator for me was being able to spend more time in Washington with family while still living my life in NYC. I had built a really incredible life in the city but as the years went by I really struggled with missing out on time with my family. As you grow older, so do they and I always had this internal guilt about that. So in my head, I had decided once I was able to spend more time back west, that guilt would diminish and I could have the best of both worlds. And it made me happy for awhile, but then I realized it never felt like enough. Even though I had spent a collective two months of the year home, I still wanted more, which was a really tough discovery. It was a decision I knew was going to disappoint a lot of people, but I finally had the confidence and assurance to know even though it was going to be tough I needed to do it. So I called off my long-term relationship, said goodbye to my friends, and packed my things into a moving truck back to the PNW. Making big decisions like that is tough, but being a business owner has really helped give me the confidence to be unapologetic about going after the things I wanted. 

M: 100% my confidence. I have grown and learned so much in the past 2 years... more than I ever expected to. Not only have I learned new skills but I've also learned more about how I work and what adjustments I might need to make to be a better business owner (and person). I was once so nervous to talk to potential clients on the phone and now I look forward to chatting with them about their goals and vision. I feel like I'm really coming into my own as a creative, business owner, and person (at almost 30 😱) and it's a really exciting time to be full of confidence, know your value, and be ready to kick some serious booty in year 3! 

Have you had any issues with support from family or friends? 

A: Luckily I've always had such an amazing support system from friends and family. They might not always understand what it is I’m doing or the amount of time I put into our biz, but they have supported me however they could along the way. The only tricky thing I’d say I’ve dealt with is people trying to plan things mid-day because I can work whenever. Which is true, and I can certainly have some flexibility, but sometimes it can seem like people don’t take my work hours as seriously as if I worked for someone else. Yes, I get to work from home or wherever I want.. but it's not always as glamorous as people like to portray. We work HARD and if we take an hour off here or there, the work still has to get done. Our clients mean the world to us and we want to make sure their projects and accounts get as much attention as we've promised. 

M: My family and friends have always been really supportive. Although I do think it's been a little bit of an adjustment for them as well. I've definitely had the conversation with my parents about "if you had a job, you'd get healthcare benefits, paid time off, and a retirement plan." Then I have to gently remind them how much more I can get out of being a small business owner. These conversations were more when I first started out and haven't happened in a really long time since I think they've realized I will never not be my own boss! 

I also have to remind friends from time to time that while yes, I can make my own schedule, I can't always just take time off in the middle of the day. Like Anna mentioned, it can be a little frustrating since it can feel like people don't take our work hours seriously but I think I put my own little guilt trip on myself because really my friends are asking and I can always say no if needed (which I have learned to do).

But those have really only been the little adjustments and for the most part, I've been really lucky to have such supportive people in my life! (My mom also helped us land one of our latest clients and has a stack of business cards she hands out! 😂) 

What do you hope to achieve in the next year at Bold & Pop?

A & M: This last year has been all about putting new systems in place and refocusing on some of our core goals and services which has led us to set an overall mantra of, “make an impact while making an income” for 2018. We’ve been working on growing our community but not just to have a community.. We want to be of service to as many people as we possibly can. Even if they aren't clients. We want to share all the things we’ve learned, our expertise, and anything else of value to help make the biggest impact we possibly can for our community and our clients.

What is a piece of advice you'd give to other biz owners and bloggers?

A: Throw the illusion of perfection out the window. No one has it all together. No matter how successful people are. They may look like they have it all together on paper, but the truth is everyone is always learning things along the way. So try not to compare your beginnings with other people’s middle or ends. All of our paths are unique so focus on testing things out in your own business and see what works, what doesn't and continue to learn from both.

M: My biggest piece of advice is to just be you and do what you think/feel is right. Comparison is seriously the thief of joy and nothing feels more icky than not following your own path. Yes, there will be people you don't vibe with and no, not every tactic someone you look up to is going to work for you. And that's completely ok! But the longer you follow your own path, the more these things won't bother you and the more successful you'll be (however you define success!)

P.S. Exciting news! We launched a free #BoldBossTribe Facebook Group and would love for you to join us! Come on over!

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