Starting A Business And Raising A Family Like A Pro With Dana Malstaff

 

Being a mother and entrepreneur at the same time is probably one of the toughest things anyone could do. It entails a whole lot of back and forth between prioritizing family time and providing for them. A great living example of someone who has found the balance as a working mother is Dana Malstaff, CEO and Founder of Boss Mom. In this episode, Dana lets us in on her journey towards figuring out how she could raise a business while nurturing her family at the same time. She shares some of the struggles many who are in this path are facing and gives great know-how on how she got through it like a pro. Join Dana in this interesting conversation about having the life you want to build.

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Starting A Business And Raising A Family Like A Pro With Dana Malstaff

My guest on the show is Dana Malstaff. Dana, how are you doing?

I am doing great. Thanks for having me on the show.

I’m excited to talk to you. For those of you that don’t know, she’s the CEO and Founder of Boss Mom. She is a mother, author and business strategist, podcaster, blind spot reducer and movement maker. We’re going to talk all about that, how she scales her businesses and how she has Facebook group of over 40,000 engaged members. First, let’s take a gigantic step back, what were you like growing up as a kid? Were you a straight A student? Were you a rebel? Did you always know you wanted to be an entrepreneur?

No, I was not a straight A student. All of the best entrepreneurs were not straight A students mainly because I’m a problem solver. From the onset that I like fixing things, I like solving things and figuring things out. I always loved puzzles. My family, we called ourselves the MacGyver family. Why buy it if you can build it? I remember us getting cardboard boxes and my mom would cut it open we’d make into cars. Cardboard boxes were our favorite toy. Which is why when I had kids, one of the first books that my brother gave me was called Not a Box. It’s a whole book about everything a box could be that’s not a box. I love it. It’s very creative.

My parents used to tell me when I was growing up, they’re like, “You can cuss, but only lazy people cuss.” Be more creative than that. We would try to be like, if you were angry or you stubbed your toe, we’d come up with funny terms to use. We’d be like, “Peaches and gravy,” or like, “Boulder dash,” or whatever those things are to get the creative juices flowing. Think of things that are new. We do things where we go on road trips and we’d seek a carful of people. We’d all have to come up with a scenario of who that family was, where they came from and where they were going.

My stepdad was a writer. My dad owned an auto body shop and was an artist, air brusher in magazines. My mom was a nurse but who was an illustrator on the side. My brother is a legit artist that teaches at the University but also has pieces in airports and different places like that. I am not visually creative at all, I became a writing creative. I got a journalism degree. I’m all those things. A lot of it stems from growing up in a family where the imagination, curiosity and creativity were highly rewarded. The more fun, silly, outgoing and crazy we were about thinking of what things were or could be, the happier we were and I think that has served me well as an adult.

It’s scary to have a baby for the first time because you have no idea what it’s going to be like.

As an adult, what was your first real entrepreneurial endeavor? Not the lemonade stand that a lot of entrepreneurs had as kids, that first endeavor.

I’d say corporate jobs, although I feel like I always worked for startup companies. The first thing I ever did is a website design work, which is funny. I feel like there are so many people that are like, “You can design somebody’s website.” Back in the day, when nobody knew how to design websites, there were no DVDs, there were no things that were super easy to do. I remember thinking it was fun, my brother needed a website for his art and so I made him a website. Somebody saw that and liked it and so I did some website design. I was a broadcast journalism major, so I had experience in design as well as writing and everything.

From there, it just putted out and I didn’t do a whole lot. It wasn’t until later that when I started my actual business, I quit my job and said, “I’m going to try to be a consultant and have a business,” before I knew what it was. One of the very first jobs I had, which I loved was I had an author come to me and they wanted me to take their book and turn it into 250 different pieces of social media. My whole job was reading the book and then pulling out how we were going to leverage it in social media. I had so much fun writing the content. That’s when I realized content strategy was my love. Once Boss Mom was born, we merged the two and we’ve never looked back.

Talk to me about that first year of Boss Mom, what was the original concept? How did that first year play out?

When I quit my job, I was in a position where the husband and the wife who owned the company were getting a divorce. There was this schism that was happening. Everybody that he had hired was being shifted out, which made sense. I proactively went to the person that was managing the shift. I said, “I see what’s happening. Could we give me 90 days? I’ll find another job. We’ll make sure my team’s intact. It gives me time.” We worked out this severance deal which was my first experience in negotiating, like proactive negotiation and it was a blast, I felt empowered by it. I went out to find a job and couldn’t find anywhere I wanted to work.

There was one place where I thought, “This is the only place I want to work. If I don’t get this job, I’m going to start my own business.” They called me up and they were like, “Dana, we love you but there’s one person that has this piece of experience you don’t have and we’re going to go with him. If you’re ever doing general projects that we wouldn’t hire you for but we hire you the project, let us know what you end up doing.” That’s when it dawned on me like, “Instead of finding a job where somebody has to hire me full-time, these people would pay me money to hang out with me for a little bit of time and take a little bit of my brain.” That’s when all of a sudden, the shift from like, “I need a job,” to, “Why would I ever have a job when I could just hop around?”

I get bored easily. I’m one of those people where my house gets moved around a lot. The couch changed positions. I’ve flipped bedrooms if my kids are ready, once from living here a year. I get stagnant. All of a sudden, I was like, “I could work with all sorts of companies.” I got super excited and then I immediately got pregnant. We had been trying and my body was saying, “You’re working too hard.” When I stopped working it was like, “We should probably have children.” I was in this weird position where I wanted to start my business. I wanted to build a website. I wanted to come up with a logo. I wanted to figure out what my positioning was and who I was going to work with while having morning sickness.

For something I’d never experienced before, it’s scary to have a baby for the first time because you have no idea what it’s going to be like. I found that I was surrounded by nobody that I knew, that understood me, and related to me. Nobody understood why I would quit my job. None of my friends had babies. I felt alone and isolated. We ended up moving back to California. We were in Columbus at the time where I’m from. We moved back here and all of a sudden there were tons of moms who had a business. Everybody was an entrepreneur. I realized that surrounding yourself with the right people does make the biggest of differences. I ended up being in a Mastermind in my first year into going into my second year of trying to have a business that wasn’t making a whole lot of money.

He was a book coach and I said, “I want to write a book.” I’m a journalism major. I always wanted to write a book. We sat down and what I thought was going to be a content strategy book ended up being Boss Mom. It caught fire so fast. Everybody was excited about, not the space that was empowering to be like, “Be a mom, be an entrepreneur,” but to be like, “Stop feeling guilty that you want to send your kids to school and do good work. Stop feeling bad that you were not meant to be a stay at home mom.”

There are so many of us that are like that, for as many women that wants to stay with their kids and have seven of them and home school all of them like, “Yes, I want those to be around in the world but it’s not going to make me feel bad that I don’t want that.” Boss Mom was born and like a good entrepreneur, I fanned the flame and then merged everything. Instead of trying to have multiple brands, Boss Mom became the way that a mom should start a business. We’re getting into calling what we call the Boss Mom Method, which is, there are very specific things that you have to put into your business, and ways that you have to grow your business. You’re not a twenty-year-old that has 40 hours a day that can go and live a laptop life on the beach. You like to be able to pee by yourself

Surrounding yourself with the right people does make the biggest of differences in your life.

It’s a different life and we’ve proactively chosen that life. We shouldn’t be made to feel guilty that we’re not able to build a business that creates some freedom we’re never going to have. People loved it. We built a business around it, a lucrative business around it. We intend to grow it as big as we can so that every mom who wants to start a business or freelance business or have extra vacation money or build the next empire, has the resources to do it in a way that doesn’t make her feel like she’s sacrificing her family, her life or what she wants to build. Also, have a business that’s financially viable.

If there’s a mom reading that either wants to be an entrepreneur or is an entrepreneur, what are some tips that you can give them in terms of balancing, in terms of running their business?

One, there’s no such thing as balance. It’s a thing that in my opinion, you shouldn’t even want it. Think about Indiana Jones, he’s got to find the exact amount of sand that weighs the exact amount, so the huge rock doesn’t fall on him. Balance implies that there’s this perfect evenness, which to me is super stressful. Nothing in your life is even. There are times when your business is going to require you to stay up until 2:00 in morning. There are times when it doesn’t matter if your kid has a fever, you have to show up, live to that thing. That’s like that, whether you have your own business or not. There are times when you say, “No, this is more important. I’m going to come over here. My dad’s sick. My kids are here. I need to do this. I need a vacation.”

There are times when you say, “No, everybody leave mom alone or leave me alone. I need some alone time because everybody’s stressing me out.” Balance to me, causes stress. I like to talk about what we call conscious integration, which is everything in your life is mixed. Stop trying to pretend work is something you separate from your kids. Your kids are going to have to grow up and understand what money is. They’re going to have to grow up and understand what solving problems are. They’re going to have to grow up and understand what failure looks like. Why not show them how that’s happening with you? Don’t hide your tears from your kids. Don’t hide your happiness. Don’t hide your frustrations. Incorporate them into learning what that is and find out what their interests are.

 

My daughter, who’s much more of an introvert than an analytical person, we have a little keyboard for her. Sometimes when I’m doing work and she’s home. She’ll come over and I’ll say, “Mom’s got to write some emails and help some people today. How about you write some emails and help some people who you’d like to help?” She’d be like, “My teacher seemed sad today. I’ll write her an email and tell her that she’s great.” That’s an awesome idea. I’ll have things like something I’m going to work on with a client and I’ll print out an extra version for her and I’ll say, “Can you mark this up? Why don’t you highlight all the Ds?” There’s an integration of how that’s working.

I feel the same way about when we work out, how we eat, and our hobbies. Our kids have to become adults and they want to be like us. Why not stop trying to balance everything as if there’s a yin and yang. In my first book, I talk about loving your business doesn’t mean you love your kids less. There’s enough of your love and affection for all the things that you enjoy. Stop trying to separate them and recognize that when you are conscious about the decisions you are making when you say, “I have a live launch that’s coming. For this week here are the parameters, unless my child has to go to the hospital, I have to create an ability for somebody else to take care of it because this is important.” The week after that, I’m going to create some space where I can consciously be part of my family and then you don’t feel guilty.

The problem isn’t balance, we just feel bad. You feel bad that you don’t call your friends. You feel bad that you are up at late and you’re not going to sleep when your partner is going to sleep. Your kids don’t get the attention you want because you are doing something you don’t know if you’re making the right decision to do that thing. If we consciously said, “My life is a big freaking hot mess. I’m going to organize it and prioritize it to the best of my ability.” You’d stop feeling guilty about the decisions you make and then balance is irrelevant. It’s a life that you’re leading and you’re consciously deciding every day how you’re going to lead it.

With Boss Mom, who is the first person you hired and how did that go? What was their role?

One of my favorite programs that I promote is Matt Johnson is who connected us, who produces both of my podcasts. He has a program called the Podcast Pitch Assistant and what I love is, I built Boss Mom by being featured. My internship was at a radio station. I’m a massive believer in leveraging other people’s audiences. About us being on each other’s podcast and you create relationships that way. One of my favorite stories is that my first hire was a virtual assistant for two hours a week to promote me on podcast.

Stop trying to pretend work is something you separate from your kids. Your kids are going to have to grow up and understand what money is.

When I came up with the Boss Mom idea and I wrote the Boss Mom book was the first thing we did. She pitched me five shows every single week. I was on 2 to 3 shows every single week for an entire year. I honestly believe that Boss Mom grew so quickly and then caught fire because that my stance and all it took was two hours a week from her to do that. To be honest, if I would not have hired her, could I have written emails and pitched myself? Yes. Would I have? No. Would Boss Mom have grown as fast as it did? Probably not.

I’ve been on 200 podcasts and probably 150 of them were from a VA that pitched it and reached out. That same mentality, could I do it? Of course. Is it a great use of my time? Would I do it consistently every single day? Probably not. Can you let us behind the scenes of what your structure is? Do you have internal staff? Do you have VAs in the Philippines? Do you have team leaders? What does that look like?

I do have internal staff. Nobody is full-time. I remember being seven months pregnant on a panel for an event where it was all about the future for Millennials. The hilarious part was I was the only even cusped Millennial I would call myself. Everybody else was in their 50s and I was 35. I’m right on the cusp. Everybody else was talking about how they were buying buildings and hiring all these staffs and I was like, “My number one goal is to never have a full-time contractor.” In 30, 50 years, we will not have contractors. The entire economy will be contractor-based. We will be our own companies. That’s the way that it’s all going and I’m happy about that.

I remember afterwards, everybody came up to me and they were like, “What will you have?” I don’t want to be responsible for 500 full-time contractors. I’ve stuck to that. I don’t have any full-time contractors. I usually hire Boss Moms, although it depends on, I don’t want to discriminate, but none women and none moms. I do find that those are the people who get my brand and understand me the most. That naturally is who I end up hiring.

The structure that we have here at Boss Mom is, I have a director of operations. Amy is amazing and she works, I would say about twenty hours a week is probably what I have her as. We doubled her time because she’s so amazing. She manages all the projects. She’s like my HR and she manages people so that’s amazing. I have Sam on my team who we call her my girl Friday. She does all of the different things but she’s my tech and branding. She does a lot of design stuff, creates templates for us and does website stuff, does our membership site back end. Jen is my funnels person. We use Ontraport. She builds all of my email funnels and everything like that. Mallory writes all of my emails and does my social planning.

Melissa takes my ideas and turns those into all the workbooks for things that we want to create. Matt’s team produces my podcast so that’s the one thing that I outsource to an agency. Everybody I have in my team is stateside. Marilyn is my community manager. She helps manage our local meetups and the Facebook group and keeps that finger on the pulse of the community, what’s happening, what’s going on. Janet is my executive VA. She manages my email, people that are wanting me to get on their show, pitching me on shows, all the things like, “I’m about to do a collaboration. I need you to listen to all of the videos from the course we made together,” and tell me what I promised people. We deliver what we promise and random things like that.

 

That’s the main core team. I have a lawyer on retainer. Boss Mom is a trademark I have to protect very much because not everybody knows that I have the trademark in five areas and they can’t use it for a lot of things. I also have a cease and desist person who’s a virtual assistant, who every month sends out cease and desist to people who try and start a podcast called Boss Mom or things like that. We’d have consultants we bring on for things that are specific like, “I need to get a better Pinterest strategy. I need somebody to help with the Facebook ad,” or something like that. I’ve had somebody to help me with Chatbox, things like that. Other than that, that’s the main core team. There are 6 or 7 of us. We’re all very close-knit.

I have had a turnover. My dad used to always say, “The worst contractors is the contractors that never leaves.” He’s like, “You want to have the people that are so good at what they do. That they either get priced out of what you’re doing or they go and start their own thing or do their own thing.” I love the idea that I have a two-year turnaround where it’s like, “I want you to be a part of this team. I want to be a part of this team to grow your business so much that you need your own team.” That’s the goal. I love my team but we also want to create systems so that if they leave me or when they leave me, that we can replace them with somebody just as awesome.

You were telling me before it’s like, “You don’t want people to leave but if they do, you can replace them with that system.” What do you look for in a hire? What does your perfect hire look like?

One is, I want somebody who’s not scared to share ideas. My business is not a dictatorship. I don’t want to have all the ideas. I’m a big believer that my team should have better ideas than me or I’m not doing my job right. I think better if somebody tells me something and then I go, “No, I don’t want that that, I want this,” or, “That’s amazing, it makes me think of this.” My stepdad was an entrepreneur for a long time and I remember doing work for him. He’d say, “Put this together.” I’d be like, “What do you want?” He’s like, “I don’t know until I see what I don’t want.” I remember being so frustrated but then I started my own business and I was like, “You’re right, I don’t have time to figure everything out. I’m hiring you to figure everything out.”

When I look at contractors or team members, I think more of them as team members. When I look at them, I want somebody who is going to give me ideas. Someone who says, “I want to take this problem and I want to tell you how I would solve it.” We have a discussion about what that looks like. I want people that want to take the lead. I want people that do work. I want to be able to give them very minimal and have them at least proactively move it forward and then come to me and I can go, “I was thinking in this different direction but I love this. Let’s keep this. Let’s move this.” It becomes a discussion. If they’re waiting for me, then I will always be the bottleneck because if I had time to do everything myself, I would do everything myself. The number one is pro-activeness. Be proactive and don’t be scared to be wrong because even if I don’t love what you did, it’s the starting off point. You can’t move unless there’s a starting off point. I like people that aren’t scared to start somewhere.

I’m assuming you’ve had bad hires, we all have. Is there anyone bad hiring experience or story that stands out?

There’s enough of your love and affection for all the things that you enjoy.

I haven’t had any horrifying stories. I have had a couple, one in particular that comes to mind where the communication was terrible. This is what I tell everybody I was like, “Don’t wait for it to be done. Don’t wait for it to be perfect.” There’s nothing of a worse feeling than feeling like you’re not in the loop. If you have clients or you’re working with people and I have this with my clients it’s, “I’m not done with that thing, here’s where I’m at,” or, “There’s a delay here.” The radio silence is the worst. Think about dating and you’re seeing somebody, there are some expectations and then they don’t talk to you for three days. That would feel horrible. It’s the same thing.

I’ve had an experience where there were these things that kept happening and we had no idea what was going on. You don’t want to hire somebody new because you think, “What if there’s something legitimate going on,” and then it ended up there was nothing legitimate going on. They weren’t telling us what was happening. For me, the worst experience was projects aren’t moving forward. I’m potentially losing revenue for these areas. I don’t want to let go of this person because I don’t know where we’re at, but they’re not telling me where they’re at. It’s a bad feeling and I don’t like that. I tell everybody, communicate, over-communicate, even communicate that nothing has happened and that we’re still exactly where we are. Keeping people in the loop that have hired you is one of the number one best way to keep clients.

I completely agree. What does your day look like? As the CEO of Boss Mom, what are you spending your time on?

It’s taken me a couple of years to get this way, but I don’t take any clients or calls or anything on Mondays or Fridays. Monday is my one weekly call with my operations director. Other than that, I’ve worked hard to create the potential for a three-day week. That doesn’t always happen because I love doing what I do. It does give me that flexibility and that makes me happy. Monday is usually strategy day where I’m on my whiteboard working things out, making sure my team has what they need. It’s also by the pool in the afternoon, happy hour. I love to work at happy hour, I eat and have a glass of wine with my computer up at happy hour with my headset on. I’m that person. All the happy hour places know me here in San Diego.

Tuesdays are client calls. Wednesdays are my group coaching and my membership calls, Thursdays, usually interviews. Friday is completely off or if there’s work that’s spilled over that needed to get done. Normally, I’m out networking. I have clients coming into town. I’m going to be going and speaking in event. I’m speaking at Pat Flynn’s event, but I’m a secret. He’s not telling anybody. He’s going to bring me up on stage and interview me. I’ve been friends with Pat for years and he’s amazing, has me doing a secret cameo as if I’m special enough that people are going to give a crap that I’m a secret cameo-like, “That sounds pretty awesome.”

I’ve structured my weeks that way so that I can have the flexibility to either work or not work. It took me about a year to get to that place. I have a Trello board with my week. This is the thing that makes all the difference. I have a Trello board and the way we’ve set it up is Monday through Sunday and then the automated system of it is that it creates a new Monday card every Monday and a new Tuesday card. I’m archiving the days as they go. It’s never stagnant. It always requires movement from me which I love. I throw in. I don’t use paper anymore. I throw into this Trello card on my phone or my computer, “Talk to this person, do this thing, brainstorm this thing,” whatever is coming in my head.

My operations director, every single day looks at the board, takes stuff off and assigns it to people and only lets me do what I make the most money doing myself. That’s been a massive thing. I used to hold things close to me and be like, “I’ll do that, and I’ll brainstorm that.” She’s like, “Why are you listening to that? Somebody else is going to listen to that and tell you what it is. We’re going to transcribe that. This is somebody else’s job.” We’re the worst at trying to do too many things. She is worth every penny that I pay her to make sure I only do the things that my talents make us the most money doing.

What advice do you have for entrepreneurs out there, mom entrepreneurs and dad entrepreneurs? You’ve been doing this for a while and what would you tell them?

The idea of trying to do everything yourself is a total recipe for disaster.

I would say you are not an island. The whole movement that we’re solopreneurs has some indicator that we should do everything ourselves is a horrible way to think about growing a business. If we were back twenty years ago and you were doing the traditional go find funding, start a business, the very first thing you would do is you would find somebody who’s a project manager. You would find somebody to do your marketing. You would find somebody to do your tech. You would find somebody to do your sales. You’d figure out what you’re best at, and that would be whatever role you fill. You’re the visionary person. That would be the exact way you do it, the idea of trying to do everything yourself is a total recipe for disaster. You’re not meant to be good at sales and marketing and all of the things that you do. Find the thing that you’re good at and then hire other people to do it.

Here’s the indicator for me. If you are going to hire somebody, say my first hire was the two people or the two hours that I hired for that person to pitch me. I have to know exactly what I’m going to do in those two hours every week that is going to ten times my revenue for the amount I’m paying that person. Otherwise, you spend a bunch of money and don’t make any money. If you have to be conscious that if I’m going to hire somebody and they’re going to take two hours off my plate, what am I doing with those two hours that is going to make me money and make me way more money than I’m paying that person. That’s to me where the magic happens with the team or where the magic happens with growing a business.

This has been great. Where can people find out more about you and what are you most excited about?

Boss-Mom.com is the best place to go. It will take you to our podcast, to our Facebook group, to all of our free resources, to all of the goodness. The thing I’m most excited about is we’ve been digging into what we’re calling the Boss Mom method, which is it’s not just about here are some ways to grow a business. It’s that, if you’re a mom entrepreneur and I would say even a parent entrepreneur, we specialize in the mom side. If you’re a mom entrepreneur there is a specific way you should be growing your business. In a specific way, you should have a team, a specific way of the things you should do and the progression of how you establish your business.

Otherwise, you will get burnt out because your business has to be simple. Your life is complex and your business has to be consistent because your life isn’t. Those two truths about being a parent means that if we don’t build our business with the Boss Mom method, then you’re going to get burnt out, feel guilty, or miss your kid’s childhood, get divorced or any of those things that can happen when you become a workaholic, which is exactly why you started your business was not to be a workaholic, to build a life that you like.

I’m most excited about that. We’re going to be adding an entirely new section to my original book that came out in 2015 and re-releasing the Boss Mom original book with a whole new section about the Boss Mom method. I’m pumped about that. Even though I’ve had this business for a while, that it’s still growing, becoming its own human being. At some point, will hopefully be a grown-up that goes off and leaves me as an empty nester, nice and wealthy. Impacting people’s lives makes me happy, progress is good.

Thanks so much for coming on. Have a great rest of the day.

Thanks for having me.

Important Links:

• Boss Mom
• Boss-Mom.com
• Facebook – Boss Mom’s Facebook group
• Not a Box
• Matt Johnson
• Ontraport
• Trello

 

About Dana Malstaff

Dana Malstaff is the CEO and Founder of Boss Mom. She is a mother, author, business strategist, podcaster, blind spot reducer, and movement maker.