Episode 14: The Real BTS with My OBM Shaina Braun

Filed in All Episodes, Business Strategy, Leadership Development — December 14, 2021

About the Episode:

The essence of this podcast is to pull back the curtains behind the scenes of being a mom, a team leader, a business owner, a wife, etc. So who better to have on the podcast today than my Online Business Manager, Shaina Braun! Shaina has been with me for over a year and has seen all of the ups and downs and has helped make so much possible for me, my family, and my business. Today you’ll hear how Shaina and I have worked to have a mutually respectful relationship, handle hard conversations, and Shaina’s tips for other leaders who run teams. 

Topics Discussed:

  • What exactly and Online Business Manager is and how Ash knew this role would be perfect for Shaina
  • Why mutual respect and the cycle syncing aspect helps Shaina and Ash both show up as their best selves 
  • Shaina’s guidance for how to lead as an OBM, working high level in so many women’s businesses 
  • The power, for a business owner, of understanding the synergy of masculine and feminine energy
  • How to have hard conversations with your team members so it doesn’t lead to more negativity 
  • How Shaina has faced all of the changes that have happened in Ash’s business this past year and why she finds it inspiring 
  • What it means to Shaina to be Shamelessly Ambitious herself and work for someone who is also Shamelessly Ambitious 

About Shaina:

Shaina Braun is an online business manager, digital marketing guru, events freelancer, & serial entrepreneur. She believes in purpose & passion and partners with intentional small businesses that are out to make the world a better place. Shaina works to build systems for her clients’ businesses so they can grow and thrive. When she’s not working, she’s also been known to cook, travel, and use Instagram as a living journal to shed light on her experiences with high-functioning anxiety and invites you to follow along if any of those things sound interesting to you.

Connect with Shaina:

Connect with Ash:

Click here for a raw, unedited transcript of this episode

Ashley McDonald (00:25):

I am so excited to have another candid conversation where I actually get to bring in my OBM, which if you don’t know what that stands for it, that is in online business manager. And Shana is someone who has worked with me for over a year. Now, we just recently celebrated one year working together and I brought her on because the essence of this podcast is to pull back the curtains, to pull back the curtains on the real, behind the scenes of building a big business and doing it in conjunction with having so many roles, like being a mom and a team leader and a wife and all the things. And so I figured who better to bring on, and I’ll probably have to bring on my husband now that I’m saying all this out loud, but who else better to bring on than the woman who is seen at all from where I began, when she started with me to where I am now and the ups and the downs and that the good launches and the hard launches and the multiple website changes and all the things that have taken place, because it’s so easy to look in on others and think that it’s so easy.

Ashley McDonald (01:35):

It is so easy to look in on others and think that it’s so easy and it’s so seamless. And it just makes sense. I cannot tell you how many times I have clients who just say like, oh my gosh, that looks like it’s been so easy or that launch, it looks so perfect. And I just always want to be the person who says, here’s what you cannot see. Here’s what you cannot see. And here’s what you deserve to see because the moment that we stopped being human, the moment that we start being untouchable is the moment I think that we stopped truly changing lives. And so I want to be as touchable as possible without getting dirty. Don’t get dirty on me as touchable, as possible by bringing Shana in. So Shana, thank you so much for taking this time to be here on the podcast. Obviously you’ve been a big part of it anyhow, but to actually be live and on the podcast.

Shaina Braun (02:17):

Yeah. Thank you. I’m excited to do

Ashley McDonald (02:19):

This. Yeah. So I want to start with really just how, I mean, you could tell the story better than I can, but how, how we started working together, your experience of me before even working with me and what the business looked like, and then we’ll kind of dig into where we are now.

Shaina Braun (02:35):

Yeah. so I first encountered Ash from a lot of people’s first touch point with her, which was this concept of cyclical alignment and using your period to navigate the rest of your life. And that was something totally new to me. I’d never heard before. And I was somebody who had been on birth control for 10 plus years and Ash told her story and I was like, oh my gosh, I have to go off birth control. What do I do? And so I kind of started navigating that journey on my own. And I had seen her give this great presentation and started following her on Instagram, following her content, learning a ton, went off my birth control. And then Ash presented this concept on her Instagram stories of needing to hire somebody. And she did a bullet point list, just very short and sweet that included everything I’ve done as an independent contractor leading up to this point.

Shaina Braun (03:30):

And I was like, huh, I could learn from her. And she could pay me. This sounds like a win-win. So I reached out Ash and I connected on the phone and I, in my opinion, we hit it off pretty well. The first conversation and conversation flowed really well. And I definitely continued learning like every conversation I’ve had with her from that interview up until now, like I learned something new every time and she feels like not only a boss and a friend, but a good person to have in my corner as a support system and the learning tools. So that’s been a great opportunity and it’s helped not only my own business as an independent contractor to grow and expand my horizons, but we’ve been able to do some really exciting things within her business and kind of take it to a whole new level and call in some new clients that feel really aligned with all the new stuff.

Ashley McDonald (04:24):

Yeah. Yeah. So true. I know it’s been so cool to see you expand your own business. You know, you aren’t independent contractor, but you’re also an entrepreneur and that’s a really cool thing to see you calling in your own clients. Right. And doing the things that makes sense and really finding your groove within this. I know we sort of like created, I remember I was hiring for, I had no other words for it, but like a virtual assistant. I didn’t know what else to call it. And then as I was having these interviews and having these conversations of like what it was I was looking for, I started to kind of build out this idea. And I remember sitting on Google, like putting in these like tasks that I was looking for. Like what, what do you call somebody that does this? So remember I interviewed you as like a potential virtual assistant.

Ashley McDonald (05:06):

And then I circled back around. I was like, I would like to actually offer you, what’s called an online business manager position. And here’s why, and so for those who don’t know, and she and I have left for you to like tap in here as well. But an online business manager is somebody who’s very high-level strategy who looks from that 30,000 foot view and helps you to integrate all the pieces that make up the business. Right. So I remember, I don’t know if you remember me saying this, but I said, I’m essentially needing to hire you because I need a boss. I need somebody to help me manage all the things I’m doing because I am such a dreamer, such a visionary. So like do all the things it’s so exciting. Wow. You know, I needed someone to come in and, and manage me if you will. So what would your take be on an online business manager? What does an online business manager

Shaina Braun (05:53):

Your desire to kind of have somebody manage you was definitely something appealing to me because my type a organized personality, I was like, yeah, you have all the creative ideas. I’ll help you pair them down and make them happen. So it was a good partnership from the beginning, but an online business manager is yeah, really that overview of strategy compared to the doing of the actual tasks, which is where a virtual assistant is going to come in. So I actually like ever since my role with Ash, I’ve created a canvas presentation that I can send out to potential clients that breaks that down a BA versus an OBM. So that it’s really clear because there is that defining difference of, and a price difference of course, for what you’re paying this person. So you want to understand like, well, why would I pay this person this versus this? And yeah, it’s really that person to kind of look at your business from an overview and be a little bit more stepped back from it so that you can be in it as much as you want to be as the owner, as the CEO, and then have somebody who is a little bit less emotional about it and less invested and can say like, well, here’s what I think is a good idea and help you develop that strategy.

Ashley McDonald (07:02):

Yeah, totally. So for everybody’s knowledge here, I did give Shane a full permission to be 100% real and honest before asking this question. Right? So she, she has safety here. She can say whatever she wants to say, and it stays on this podcast, but Shana, what has it been like working for me, both as me as a person, but also in this company and like, what have you seen change? And what does that experience been like? Like really give them, like pull back that curtain.

Shaina Braun (07:33):

Mostly I’ve learned what, what I like in, in a boss and in a partnership and what I, it’s very interesting what I thought I liked about my last job, which I still like have so much love for. However, this is very different, different role and different personalities working together. And it just kind of blew my mind where I was like, oh, these are things that I really appreciate and will now like be non-negotiable for me, moving forward with clients that I was not aware of. So those are things like how much you practice, what you preach. Like, I am always very clear on if it’s a kid’s birthday, we’re not on email and I’m not, you’re not going to respond and I don’t need to expect a response. And same, like the same respect comes to me where if I’m busy doing something ashes, not asking me to be available off the top of the hat.

Shaina Braun (08:28):

Like I, it just, we get the same mutual respect there, which I have always appreciated. There’s also things like how the cycles thinking plays into everything. Like, I really love that we can both plan around our cycles and use that to whether it’s creating content or doing a podcast like this traveling. Like we can use that to our advantage so that we’re both showing up as our best selves, which is really, really cool. There’s things too, like Ash being super ambitious, which is awesome. And that she can speak more to this, but we’re both manifesting generators, which works well for us, but that also means that we want to not be stuck in anything and change ideas and all the things and Ash even more so than me. And so there are things where it’s like, oh, we’re, we’re pivoting, we’re doing something different now. And not that it’s bad or anything, but it has been a learning curve from that standpoint of like, she has no fear, whereas I have fear around certain things. I’m like, oh, we’re going to do this and she’s fine with it. So let’s just, let’s just do it. And it’s okay. Well, I’ve learned a lot there.

Ashley McDonald (09:38):

That’s so funny. And I wouldn’t, I would, I would structure that. I wouldn’t say I have no fear. I just, I have fear while flying. So like I’m more of a jump and then feel the feelings, which has definitely bit me a few times, but it also has brought me so much thrill when I think about like what I want life to look like if I could give it one word and I think of anything, maybe you really saw this until loom. Like, if I could give my wife one word, like if, what I’m really after it’s, it’s thrill, it’s thrilling thrill in my business thrill in my personal life thrill in my day to day. Like how can I just make it more thrilling, even if it means jumping off cliffs or swimming with

Shaina Braun (10:15):

Crocodiles, or I thought I was adventurous

Ashley McDonald (10:21):

And maybe it’s just like, I, I definitely have a addiction to adrenaline. Let’s just say that, that is, that is for sure the truth. So in terms of even just the company as a whole, how has it transformed? What have you seen change?

Shaina Braun (10:36):

Yeah, it’s been really cool to watch the growth happen and be involved in it. So the company has kind of gone from this entry-level woman. Who’s just learning about her own period and the fact that that can even affect your day to day and transitioned into this new woman who will already knows about her period and has already started utilizing that to help her business. And she’s this high level CEO or owner of her own company, and really has the motivation to go after these goals and has more of that personality of having no fear or having the fear after already doing it and just being willing to do it anyways. And it’s just a totally different level of business from the people that we work with that it’s really, really cool and expire inspiring. Yeah.

Ashley McDonald (11:25):

So if you could give guidance, one of the things I would love for people to be able to take away from listening to this podcast is how to lead, right? And I will never, ever, ever stand here and say, I’ve perfected anything in my life. So this isn’t like a, how have I done it that you need to teach them? But like, what is your experience been as someone who works? So high-level, and women’s businesses, mine not being the only one. What are some tips that you would give to a high level CEO of like, do these things with your OBM, with your VA, with your social media manager, with whoever you’ve got on your team, do these things

Shaina Braun (11:58):

Become a therapist,

Shaina Braun (12:04):

But in all honesty, I think that your therapy background like serves you very well as a leader and makes a huge difference in the way you communicate with everybody, whether it’s employees or contractors or clients, whoever. So that’s things like you’re very, very aware of not shaming people for anything, which makes a huge difference because all it takes is one time, right. A feeling like, oh, I messed up. Somebody shamed me for it. And now it’s not a safe space anymore. And so that’s a huge thing. And the other thing that kind of therapy related, but kind of depends on what therapy you’re in is like personality tests and stuff. So, yeah, she’s big in Enneagram and human design. And those were things that we talked about before she hired me and I love things like that. And so it was really cool to have somebody care about understanding my work styles and my personality style and how those would best work together.

Ashley McDonald (13:01):

A hundred percent. I would say, I, I love that you say that because working with people, but even like in marriage, even with my clients, like when my client starts working with me, I want to know what is your Enneagram? What is your human design? What is your love language? How do you receive, you know, any sort of feedback? Like what does that look like for you? Because I fundamentally believe that women in general, but humans overall are such multifaceted individuals and we don’t receive and experience life the same. And that’s a beautiful, beautiful thing, but it can also be very troubling. And I see a lot of these wonderful CEOs that have hearts of gold as being completely different to the people that they lead for no, not any malicious reason whatsoever, but from not really understanding how this person feels and experiences.

Ashley McDonald (13:50):

And I would say that this is, I don’t think you need to be a therapist. However, I would say it’s really powerful to understand the synergy of masculine and feminine energy. I know I talk about that all the time, but understanding there are times to be in that masculine, in that really strong, assertive. I know what I know that I know that I know space and really being able to step into that CEO role and say what it is that you need, but it has to come with the synergy of feminine and the feminine is inquisitive and it’s caring. It’s soft. And I feel like sometimes people get into these leadership roles and they, they believe that they have to live in masculine. Yes. Right. And in living in masculine, it’s dictatorship it’s, this is what you need to be doing. It’s just, like you said, like not honoring those boundaries and things like that, but I needed to know, as soon as you started working for me, what is your workflow?

Ashley McDonald (14:38):

When do you work best? When does it feel good for you? Not only because I want to honor that for you and be able to cultivate a relationship that’s long standing, but because I’m only going to get the best work out of you. If I know how bring that out of you. And to honor that in you, I would also say, this is funny that you’re bringing this up because I’ve had this conversation a lot with people having hard conversations with employees. And we’ve had hard conversations in our time together as well. Like it’s not to say it’s been, I don’t want anyone to listen to this and think, oh, well, this was just the perfect match. You will find people that feel really, really aligned. And you still have to have hard conversations. And that is the masculine side of like, you have to take ownership of your company and where your resources are going and what’s going to feel good.

Ashley McDonald (15:20):

And just the alignment of it. But also like if there’s an issue that issue will persist, unless you can stand in your masculine and like own that. But also, yes, I will say one of my greatest values is never, ever, ever to induce shame, never, ever, ever to induce the shame. And for me, what that looks like is always coming from a space of creating and cultivating safety with the people around me first, before having that conversation and the very simplistic, this is very therapeutic. I teach it to all my clients. If you forced me in any capacity, you’ve heard this. Even the men nannies have learned this, right? You have to operate when you’re having hard conversations through the lens of the compliment sandwich. And the compliment sandwich is essentially to always start with positive feedback. How has this person really benefited you in your life?

Ashley McDonald (16:08):

How has this person done things that really astounded you made you excited? All of these kinds of things. Even in my marriage, I have this, I do this, right. If I have something I want to talk to Jake about it is first where you awesome. Right? Then we give the feedback. And what that does is it basically creates this barrier of safety of like, Hey, I see you. I love you. I honor you. I respect you. I am in the arena with you right now. And also let’s have a hard conversation, right? So it’s, it’s that compliment or that encouragement or that I see you statement. And then it is the here’s where I’m feeling that we need to progress. Here’s where I’m feeling like there’s some hardship. Here’s where I’m not feeling aligned, whatever that case may be, but then always finishing it with more compliments.

Ashley McDonald (16:53):

And so compliment sandwich is a very simplistic way to look at it. But in essence saying, and the reason why I know I can have this conversation with you is because you and I drive really well together or because you and I can have these conversations and still come out the other end on top. And then where the feminine comes in is that inquisitive. Also, I want to hear your feedback, right? There’s a difference between a leader who just says, here’s how I feel. And I don’t care about anything else. And the leader who says, how do you feel now? How do you do those compliments in an authentic way? And it comes off genuine even when you’re frustrated with their behavior. Yeah. Very good. So one big thing, and we just talked about this and laugh about this is I had said to Shana, like I needed to process this.

Ashley McDonald (17:38):

I needed to have, I need to think about this, that I wasn’t responding. I don’t like that. I don’t like to respond from emotional space, correct to myself. Cause I said, that is both baseline. I love responding from emotional space. Everybody was any relationship knows, but it’s very easy to just feel the thing and say the thing. However, I feel like where I falter in marriage, I know I’ve been leadership because I can really pause and know that I need to be emotionally sound. I need to take the time to journal on this to process this, to even go to a mentor. I just had a conversation with a client today who needed to have that conversation of like, how do I, how do I say this in a kind proficient way? Right? That’s so incredibly valuable. So have the people, but do process it first yourself, process it first yourself, because then, and I will say, even in hard conversations that you and I have had Shana that I sit and I do a list of all the things I’m so grateful for. And so appreciative of because our resoundingly guests will always, always, always be so much more than maybe this little area that doesn’t feel good. And that again, can be true of our clients. It can be true of our marriage. It can be true of our kids, right? Like it’s very easy to focus on just what feels hard. It’s very high level leader of you to lead yourself into focusing on what is really great right now.

Shaina Braun (18:56):

It’s almost the personal side of the done list, whereas knowledge and all the good.

Ashley McDonald (19:03):

Yeah. Yeah. So what Gina’s talking about, I think I’ve talked about in the podcast, but I love to create my dead-end list of like, if, if nothing else happens, if nothing else changes, if nothing else grows from this point, what have I accomplished? And just being able to sit in that presence and that gratitude of where I’m at in this moment really allows me to come from a very high level energetic space when I’m launching, when I’m working with clients, when I’m heck even on like vacation, my family, like we all are so much further along than we were yesterday and the day before that. And the day before that, and that is such a beautiful thing that we never give ourselves enough credit for. We never sit in, in, in presence in that. And that’s right, right. I love it. So you’ve seen all these changes more particularly though recently, there’s been a lot of burning things down in my business.

Ashley McDonald (19:48):

You, you, if you’ve listened to this podcast, you’ve heard of a lot of the burning of the things down, and it’s also been very much a theme among my clients, which might be the season. It might be because they’re working with me. I’m not really sure. It just feels like that time where you just got to almost give yourself permission to, to burn it all down. What has your experience been in that state? And we kind of touched on this, but what is your experience been on that state of kind of starting from scratch in some areas, even though you’ve been with me for a year

Shaina Braun (20:17):

It’s really interesting because from a personal personality standpoint, I would think it’s something that I would like have kind of a wall up against and be a little scared of, but in your business and with other clients, even I really, really love it because it means that you’re aligning with what feels best to you, which makes the work better. It makes working with you better. It makes the clients that are like, everything is just better when it’s something that is aligned with you versus something you feel like you’re constantly pushing against because you feel like you should be, or society has told you that that’s the correct way to run a business. And so it’s been really inspiring and cool to see that you can start over. So to say and do things differently and still find success and find success in different ways, because success is going to show up differently for different people, whether it’s monetary or time being time abundant and things like that. So there’s more than one way to do things. And it’s nice that it doesn’t have to be this big, scary thing of like, oh, I don’t know what’s going to happen. If we change things, it’s more of a, let’s try it and see what happens and whatever feels good. And I like to do things that feel good.

Ashley McDonald (21:29):

Yes. I think that’s so true. Like that’s whether you’re burning things down or just changing things up. I think what Shane is saying there, that’s really important to take home with you is when you are energetically aligned, your team feels it. Yeah. Your people feel it, your clients feel it, your audience feels it. Right. I was just looking up on my phone because I saw this post. I think I reshared it recently, but it was like, you, you can make it up as a long, sorry, let me start over here. You can make it up as you go along and still be a raging success. It’s just that permission of like, there is no right or wrong way to build your life, to build your listening business, to build your team. There’s no right or wrong way. It’s are you, are you all there? Are you living in every moment as fully as you possibly can and not only learning, but integrating the learning. Right. Like, I am not, I am not who I am because I just kind of roll with it. I’m who I am because I spent hours upon hours a week, still learning, still growing, still allowing myself to be a newbie. Yeah. Right. Which is probably why I keep wanting to break things down. Cause I’m like, Ooh, so many exciting new things. I’m, I’m evolving so fast that the things I’m creating don’t feel as advanced as I want them to be. And that’s okay too. Like it gets to be exciting in that state. So,

Shaina Braun (22:45):

And then that energy comes through so strong when you’re, whether it’s business or personal, like you can tell when somebody is excited and it feels magnetizing and you want to be involved in it versus when it’s something that you’re just doing to do it.

Ashley McDonald (22:57):

Yeah. It’s so true. It’s so, so true. Funny enough. I totally missed, usually at the beginning, I was so excited to get to this conversation. Usually at the beginning of every podcast, I know, you know, this, I always like to talk about what I’m grateful for and what phase I’m in. And so we’re going to do that really quick. Right now. It’s a little backwards we’re going to do it. So right now I’m grateful. I’m really excited because this is the behind the scenes thing. And I know I’m pulling back the curtains, but this is just something I can’t pull the curtain back. Right. This moment. I’m going to tell you Shana though, after we stopped this call and I’m very grateful for a very expansive realization in business that I had last night growth milestone that I hit without even knowing it, which feels very, very, very exciting. And I’m in my flood Clare phase. So all the creative energy, all that good stuff, this is definitely, I mean, you could probably sense it and how I’m speaking and all the things it feels so, so good. What are you saying? What are you grateful for? What phase are you in and tell us your interpretation. Cause they get to hear mine every week. Your interpretation of the phase that you’re in.

Shaina Braun (23:52):

Yes. I am super grateful for just today. I, well, a few weeks ago I bought myself a vacation and then just today I bought myself a therapist and I was thinking about those two things combined. And I was like, wow, that those feel like the most self care things, like most attractive things to me, I’m like, great. It did, it feels like a win. I’m super grateful. And then I am tail end of my ovulation phase. And so to me that means like good communication speaking comes easily. More energy, more outgoing, more confidence, all the things

Ashley McDonald (24:31):

Because I love it. I love hearing other people’s perspective on it too. Cause it’s, we are, we all have it in us, but it is very personalized, which is really cool. So at the end of every podcast, I love asking the people who are on what it means to them to be shamelessly ambitious. Actually, I want to hear that for you. I also want to hear, so I want a two-fold answer here. I want to hear what it means for you to be shameless ambitious and also what it means to work for somebody who has shamelessly ambitious.

Shaina Braun (24:57):

Yes. Okay. So for me being shamelessly ambitious means it’s kind of twofold being in a space that feels safe to show up in as my complete self. But also doing that shamelessly regardless of the safeness of the space. So obviously the safe space makes it easier, but as I’ve been in those safe spaces, like kind of using those to cultivate the confidence, to do that in other spaces as well. And I’ve always described myself as an ambitious person. I’ve always been, self-motivated intrinsically motivated. I, you know, got good grades in school. Not because my parents ever told me to, but because I felt like I had to and I’ll know where that came from, but it’s a personality thing. And so I’m sure it’s in my human design somewhere, you know, Enneagram any room. Yeah. That’s the one coming out. And so just kind of embracing that ambitiousness and especially as a woman, like being okay with that and especially in the dating world and you know, just seeing kind of how that shows up and doing it shamelessly. Yeah.

Ashley McDonald (26:06):

I love that. And what about

Shaina Braun (26:07):

Working for somebody? Yes. So working for somebody shamelessly ambitious, I think has made all the difference in kind of the, I keep coming back to the word, confidence feels really aligned right now. Competence in myself, confidence in the business and confidence in our relationship working together of seeing you show up wholeheartedly as yourself and shamelessly as yourself and embracing your ambition has made it okay for me to do so and has made it exciting to jump on board with whatever your ideas are because it’s like, yeah, let’s see what happens. And there’s no kind of skin in the game in a negative sense of like we’re in this together and we’ll see how it goes and nobody’s going to be kind of on the chopping block. If it doesn’t go well, we’re learning together. And so it feels really good.

Ashley McDonald (27:00):

I love it. I love it. Well, thank you Shana for your energy for your time for being here. I think this is just a really good conversation for both for people to hear. And the reason why I call these candid conversations is because there’s not necessarily a big lesson I want to teach. I just want to normalize this kind of stuff and what it looks like to build a team, the ups and the downs, the highs and the lows and what it really feels like also for you so that these women can walk away going. Here’s some things I need to activate and learn and grow in in order to really be the best leader I can be for the team that I am so humbly grateful to be able to lead. So thank you so much.

Shaina Braun (27:37):

I love that this conversation was focused on leadership so much because that is a huge part of how we work together and that, that makes all the,

Ashley McDonald (27:45):

It really does. It really does. Well, thank you so much. So, so much again, another episode that pulls back the curtains and hopefully allows you to see just how not alone that you are.


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I am the definition of duality—I swear like a sailor and break rules like it’s my job, but I also hold incredible space for my clients and work my ass off to help them achieve the success they’re after (but faster).

My background in counseling and my experience founding three multi-6-figure businesses gives me a unique perspective on what it means to show up and serve as an ethical and successful CEO. Leaning on my experiences, along with the experiences of the hundreds of women I’ve been honored to work with, I offer founders a psych-backed and human-first approach to scaling their legacies—both in and out of the office. 

I don’t believe in a one-size-fits-all approach to anything, but especially business. Because at the foundation of any profitable, sustainable, ethically sound business is one thing: humans being humans. And to do anything without first considering the human behind the action (i.e., with intention and vulnerability) is to remove our most powerful predictor of success—ourselves.

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