Veteran Led

What does it take to build a business while raising a family, navigating military life, and refusing to lose yourself in the process?

In this episode of Veteran Led, John S. Berry speaks with Andrea Singsaas, founder and CEO of The Tyne Group, about leadership, boundaries, and building a business that can move with military life. A longtime military spouse and mother of three, Andrea shares how she built her executive coaching company from a master bedroom closet, one client at a time, while moving around the world and back again.

The conversation explores burnout, accountability, decision-making, and why so many leaders struggle to protect their time. Andrea explains how leaders can clarify what matters most, set non-negotiables, and stop saying yes to everything. She also breaks down the difference between chaotic leadership and effective leadership, and why candid communication, strong boundaries, and the right support system matter in both business and family life.

This episode is a practical guide for Veterans, military spouses, and leaders who want to build something meaningful without losing themselves along the way.

Guest Links:
LinkedIn: https://www.linkedin.com/in/andreasingsaas/
Website: https://www.thetynegroup.com
Instagram: @andreasingsaas 

Learn more at ptsdlawyers.com

What is Veteran Led?

Veterans know how to lead. The lessons we learned in the military form the foundation for bigger successes in business, entrepreneurship and community.
Host John S Berry, CEO of Berry Law, served as an active-duty Infantry Officer in the U.S. Army, finishing his military career with two deployments and retiring as a Battalion Commander in the National Guard. Today, his veteran led team at Berry Law, helps their clients fight some of the most important battles of their lives. Leading successful teams in the courtroom, the boardroom, and beyond, veteran leadership drives the firm’s rapid growth and business excellence.
Whether building teams, synchronizing operations, or refining tactics, we share our experiences, good and bad, to help you survive, thrive and dominate.

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[00:00:01.400] - Andrea Singsaas
This is business, not friends, and no is a complete sentence. And the more candid you are with your communication and the more you protect yourself and your time, the more people are going to respect you.

[00:00:16.160] - John S. Berry
Welcome to Veteran Led. Today's guest is Andrea Singsaas, founder and CEO of The Tyne Group. Welcome to Veteran Led, Andrea.

[00:00:22.610] - Andrea Singsaas
Thank you so much for having me. I'm glad to be here.

[00:00:24.700] - John S. Berry
So what does The Tyne Group do?

[00:00:26.130] - Andrea Singsaas
The Tyne Group is an executive and leadership coaching business, and we also do retreats, workshops, and I do some speaking as well.

[00:00:35.510] - John S. Berry
And you have a ton of credentials, but what the audience really wants to hear about is that origin story. How did you develop this company and how hard was it?

[00:00:43.300] - Andrea Singsaas
Exactly. So I was a military spouse for 8 years. I needed something that could travel and support a military career as a military spouse. And I don't want my kids— I have 3 daughters. I wanted them to see that mom could build something and do something alongside this military journey. And executive coaching worked because I could do it virtually from anywhere in the world. We literally moved around the world and back again. And, uh, it started out, uh, once we got back to the States after being in Germany, I was in a master bedroom closet on a box of Easter decorations, had my laptop propped up and just, grit and gumption and one day at a time, one client at a time, built the Tyne Group.

[00:01:24.160] - John S. Berry
And now your clients, are they mostly virtual or in person?

[00:01:27.280] - Andrea Singsaas
Good question. So, I have clients all over. Some are, uh, local, but most are all over the world. You know, that's the nice thing about being part of the military community for so long is my connections, my network is everywhere. And so, I can tune in and connect with them virtually. And then for workshops or speaking engagements, I travel all over. I'm known for traveling quite a bit.

[00:01:50.690] - John S. Berry
And we're at Veteran Edge, and I know I met you at the Military Influencer Conference.

[00:01:53.830] - Andrea Singsaas
Yes.

[00:01:53.970] - John S. Berry
How much do you travel?

[00:01:55.420] - Andrea Singsaas
Oh my gosh, I probably travel at least a couple times a month. So, it just depends on what clients have going on or what their needs are, because I'm here to serve them, right? It has to fit into their schedule and their need, you know, their needs. And I'm here to meet that.

[00:02:10.500] - John S. Berry
And the reason why I ask is because obviously as a parent of 3 children, right, and a mil spouse who's moved a lot over the last several years, it's, it's not easy when people— you have to meet people where they are.

[00:02:22.630] - Andrea Singsaas
Exactly.

[00:02:23.580] - John S. Berry
And, and as, and as a coach, right, as, as a leader, sometimes they need that, that physical presence.

[00:02:29.760] - Andrea Singsaas
Yes.

[00:02:30.100] - John S. Berry
Boots on the ground still matters.

[00:02:31.700] - Andrea Singsaas
Exactly, exactly. And one of the things that I advocate for with my clients is you can build a professional life around your personal goals too. So that's what I'm doing with my business is I travel when I can or when it makes sense for me and my family. But I also put boundaries around the things that are really important to me, right? I'm not gonna miss the last day of school. I'm not gonna miss, you know, donuts with mom or whatever those things are. So, uh, you do have to have those priorities in place because nobody else is gonna protect that for you. And so many people get overwhelmed and stuck in this constant go, go, go that they get lost in themselves. And that's why they get burnt out.

[00:03:11.510] - John S. Berry
I think that is so important for Veterans to understand because it is— hey, you're told where to be, when to be there, and you have this immense sense of duty to the mission. And then you get out of military service and it's that sense is still there. But the problem is you don't have to be there. You actually have the choice, and you can set boundaries. And it's easier to say, I'm gonna set this boundary, but to keep that promise to yourself is, like I said, it's easy to say, hard to do. So how do you coach your clients to set those boundaries and maintain those boundaries?

[00:03:43.280] - Andrea Singsaas
Well, first of all, they have to know what's important to them. A lot of people haven't even taken the time to think through, like, what is truly deeply important to me? They just say, you know, flippantly, oh yeah, my families important. Well, what part of that is really important? Like, get them to commit to, like, write it down on paper on purpose or whatever, on your tablet notes, I don't care where, but get it on paper on purpose that like, these are the things, these are the non-negotiables for me. So often we have non-negotiables in business. You know, there are non-negotiables in every situation, but we don't think about 'em for ourselves or our family, and they end up leading their family poorly. It ends up, you know, everything kind of runs downhill that way. And we're good at it at work, we're bad at it when it comes to leading at home.

[00:04:27.980] - John S. Berry
Yeah, and I found it bleeds over into every area of your life. If you don't set boundaries at work, then you don't set boundaries at home, and you don't set boundaries with other relationships. And inevitably, uh, you get walked on. Yes, because you want— I mean, we're all naturally people pleasers. We all want to keep the peace. We want to make our family happy. We want to make our clients happy. We want to provide outstanding service. But there is a cost, and you can't do all of it.

[00:04:54.490] - Andrea Singsaas
And if you do it all, you're doing it all poorly.

[00:04:57.220] - John S. Berry
Yes.

[00:04:57.530] - Andrea Singsaas
You have to select and be picky and choosy about what's going to be the most rewarding to you professionally and personally. And that's why being able to say no— if you don't know what you stand for, you're never going to be able to say no. You're going to take it all in and try to do it all and then wonder why you're chasing your tail and why you're out of hours at the end of the week. And still don't feel like you have any traction on your life.

[00:05:17.700] - John S. Berry
And it all sounds great, but how do we stay accountable?

[00:05:20.190] - Andrea Singsaas
Exactly. Well, a couple of different things. You have to have a support system in place, you know, whether it's your spouse or people at home. Sometimes they get tired of hearing about that, whether it's a coach or whether it's somebody at your work. You need to have somebody that's going to hold you accountable. Your battle buddy. I don't care what it is, but somebody that's going to look at you and say this. You've been saying this. But you're doing this other thing, or vice versa, you're doing this, but it doesn't align with what you've been saying is important to you. And so, somebody to keep you in check and somebody that's going to regularly check in with you, whether that's once a week, once a month, once a year, that's the way that you're going to really have some of that accountability. You can do it yourself too, but I feel like if you have somebody else that is calling you out or saying, hey, John, you said you were going to be doing this, you said you were going to be at all these kids' baseball games, but I saw you over here on your phone.

[00:06:09.860] - Andrea Singsaas
Is that really what you wanted when you said that that was a priority.

[00:06:14.880] - John S. Berry
Yeah, and it's, it's tough. And I've learned you don't have to respond to every email. You don't have to respond to every text message. You don't have to take every call. And once you set those priorities, like, other people will generally respect it. And those that don't respect your priorities probably don't need to be in your life.

[00:06:30.770] - Andrea Singsaas
Exactly. And the other thing is we get so worried about, like you said earlier, people pleasing and being kind that we forget that there are reasons to get people out of your life. There are reasons to change your circle. It's not that it's a hard pass or you are excommunicating them by any means, but there are going to be some people that are going to be more beneficial to you personally or professionally. And those are the people that you need around you, especially in periods of growth, periods of change. Things get hard. Get the right people around you, that wise counsel, those great advisors. That's what's important.

[00:07:06.960] - John S. Berry
And I find that you are going to outgrow people, right? It's just like in business.

[00:07:10.190] - Andrea Singsaas
100%.

[00:07:10.940] - John S. Berry
The people we've had on our team for a long time either grow— I say if you can't grow with us, you can't go with us because we want to keep getting better. And then the duty is always to our top performers to help them become even better because when we don't, they suffer, their families suffer. So we're always looking at, okay, how do we maintain greatness? And to do that, you've got to prune, right? Everybody can— you have to do that in your personal life as well. You will outgrow certain relationships. There will be certain relationships that are great for a certain season of your life. That are not necessarily going to be relevant later. And there are points where it becomes toxic if you hold on to those relationships for too long.

[00:07:46.380] - Andrea Singsaas
Not all relationships are healthy relationships. We think about that very easily and transfer it to our personal lives. We know when there are relationships that are unhealthy for us, but we don't often do a good job of getting rid of that noise when it impacts our professional lives. And there are some things you can't change, but you're in control of a lot more than you think you are. We just don't take the accountability to make that choice.

[00:08:10.380] - John S. Berry
So, what do you say to the Veterans out there who say, yeah, that sounds great, but I always feel bad when I say no, or I always feel bad if I want to commit to something. Someone asked me for something and I tell them yes, but I know I really don't want to do it. And now I'm conflicted because I don't want to break my word. I want to be true to my word, but I really don't want to do this thing. I just said yes to be polite. To be kind, but I don't want to do it.

[00:08:33.400] - Andrea Singsaas
Exactly.

[00:08:33.670] - John S. Berry
What do you tell people?

[00:08:34.350] - Andrea Singsaas
Well, this is business, not friends. And no is a complete sentence. And the more candid you are with your communication and the more you protect yourself and your time, the more people are gonna respect you, right? If you allow people to walk over you, walk over your time, walk over your boundaries, that's not gonna get you to where you want to go. Especially if you want to be seen as a leader, somebody that, um, others look up to and respect.

[00:08:59.660] - John S. Berry
I think the challenge a lot of times is, as leaders, especially in the military, we are the problem solvers. And you have a business, you have a family, and you become the problem solver. People are always coming to you with their problems. And how do you deflect those and say, you know what, I'm not gonna solve this problem, you solve the problem?

[00:09:13.220] - Andrea Singsaas
Exactly. Well, I mean, as a coach, I'd say, hey, maybe you should go get a coach. But how do you deflect that? So, I would say you do have to make time sometimes. Maybe it's somebody that's on your team, right? Like you're mentoring them, you're coaching them on your team to become better. Say, we have a certain amount of time to discuss this, or we can discuss this at another time. A lot of times your, your time gets sucked up by all these things that just pop up that aren't scheduled and established on your calendar. So that's one way that you can do it. Another way that you can do it is, um, really be upfront and honest about, this is the expectation that I have for you of this business relationship, of this, um, organization or team, and this is what we're working towards. And be really strategic in your communication and be very straightforward. Don't, um, don't let the lines blur too much.

[00:10:05.550] - John S. Berry
I think there's always going to be times where you have to have difficult conversations, and the easy ones that we avoid, right, the easiest ones to avoid are the ones where we can just do it, we can just solve the problem for them again and again and again, as opposed to having that difficult conversation. But in the end, if you have that difficult conversation, it's probably gonna save you quite a bit of time and stress down the road. It's just take the pain now, take the hard pain now, or take a lot of pain over an extended period of time.

[00:10:30.770] - Andrea Singsaas
One of my favorite questions I ask during coaching is, should you be doing that? It is a yes or no question, but oftentimes there's a pause or a hesitation when it's something that is causing them conflict, taking up too much time, taking up too much bandwidth. Well, should you be doing that? Who should be doing that instead? And it kind of makes people think like, oh no, I don't have to do that. We take on so much. We want to solve everybody's problems. We want to do so much for others, but we forget our bandwidth is like a certain level too.

[00:11:02.770] - John S. Berry
Absolutely. And that takes us to the after-action review. Your examples of great leadership and horrible leadership. You don't have to name names.

[00:11:09.590] - Andrea Singsaas
Mm. Great leadership. I can think of poor leadership, and most of it is the leadership that I've experienced, right? It's the manager that is doing too much for themselves. They have poor delegation, poor communication. They overly communicate and they communicate at all hours, setting the expectation and the culture, um, as more of a chaos culture, right? The more collected and pointed and, uh, really efficient you are as a leader, leaders are gonna develop other leaders that look like that. So, you're setting the tone for the culture in your organization. And that leader that I'm thinking of, it was chaotic. Everybody never— nobody ever looked forward to getting an email from that leader. And those emails came in at all hours, all the time. Great leadership are the ones that cultivate, you know, that followership. Like, they are the ones that they're going to tell you the hard truths. You're not always going to want to hear it, but you know that they're going to stand up and do exactly the right thing. For the better of their team, for the better of their people, for the better of the organization. And so, I guess those are some of my really good— and they're not afraid to say, hey, I screwed this up, right?

[00:12:24.120] - Andrea Singsaas
A really good leader will say, hey, I kind of screwed that up this time. Here's how I'm going to own it. And it promotes that culture of being able to fix it, but then also being able to play as a team and be transparent.

[00:12:36.520] - John S. Berry
Yeah, one thing I learned was that We start— when we establish our core values, we would talk about them. We make sure everybody memorized them. Then we would give out awards every quarter for core values. But it wasn't until every quarter where I would say, hey, this is one of our core values and this is a decision I made that did not follow it. And here's how it went badly for us. Once you can really own that, then it's not just the core values are here. Hey, congratulations. You, you were— you earned the most commitments, one of our core values, the commitment award, because you were so committed. That's great. But it's like, no, we committed to this and we didn't follow through with it. And these are the secondary and tertiary effects that harm the business and, you know, that really had an impact that we did not foresee. We thought we were just, hey, this is— we got too much on our plate. We're going to drop this one commitment. And no, we should have stuck it out.

[00:13:23.310] - Andrea Singsaas
The lessons you learn the hard way are your best teachers, right? And you're never going to do it again.

[00:13:27.320] - John S. Berry
Absolutely. So, Andrea, where can Veterans and other people who want to get a hold of The Tyne Group learn more about you and your company?

[00:13:34.870] - Andrea Singsaas
Absolutely. So, I have a website. I'm on LinkedIn almost every day just sharing bits and pieces, leadership lessons learned. And then also I have Instagram and Facebook.

[00:13:50.580] - John S. Berry
Thank you for joining us today on Veteran Led, where we seek to help Veterans build an even bigger, better future after military service. Unfortunately, for some of our Veterans, the roadblock to a better future is that they are not receiving all of the benefits that they earned. If you need help appealing a VA disability decision, Contact Berry Law.