Episode 142: The Art Of Letting Go: Build A Better Business By Re-Shifting And Refocusing With Brian Tenney

Letting go is one of the hardest things that entrepreneurs have to do when they’re ready to scale their business. But if you’re to create a better business, you need to be able to take your hand off of the steering wheel and bring in people who will take your business to the next level. However, our collective experience as entrepreneurs has taught us that this is something that’s easier said than done. There is something about being in the middle of action. We crave for that dopamine hit of getting things done and getting results. What if we could keep that reward system going on without necessarily being in the weeds all the time? In this episode, JourneyTEAM CEO Brian Tenney tells us how to do that by re-shifting and refocusing where we’re getting that reward. Join this conversation and learn the way toward a better business without headaches and check out our Business Mastermind Program!

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Welcome, everyone. Once in a while, I want to remind everyone who we’re focused on and what we’re doing here. If you’re in that $1 million to $10 million space or range in annual revenue, this show is for you, especially if you’re trying to grow and you’re bumping into some challenges. We believe that you are an elite entrepreneur if you make it to that million-dollar mark because only 3% of businesses that ever start make it there. You’re in rarefied air.

We’re bringing amazing guests each time in each episode to talk about their journey as they’ve scaled through that $1 million to $10 million space. Not all of them have made it to $10 million and beyond. Our guest has. He has built quite a business, and I’m excited to introduce you to him. Whether you’re growing from $1 million to $3 million, $5 million, or $10 million and beyond, or you just want to build a better business without going crazy, you’re going to hear some great tidbits, practical experiences, and great insights from our guests here.

Without further ado, let me introduce you to Brian Tenney. Brian is the owner and CEO of JourneyTEAM. JourneyTEAM is a technology and business consulting firm. They’re a Microsoft shop, so they specialize in Microsoft products and services. Since retiring after one season as a snowboard instructor, Brian has been working at JourneyTEAM since 2003. He’s had all kinds of roles. It’s every role you can imagine, marketing, sales, project management, technical consulting, and COO. He is now the CEO and the Owner of JourneyTEAM.

During the time that he has worked there, they’ve grown from 8 people to 150 team members. That’s incredible. Some of you are thinking, “That’s a lot of headaches with all those people.” I hope by the time you’re done tuning into this chat that I have with Brian, you’ll come to understand that it doesn’t have to be headaches with more teams. In fact, it can be amazing. That’s why we have Brian here. Brian, thank you for joining us.

Thank you. I am excited to be here.

Tell me quickly about this snowboard instructor stint that you did.

When I was a kid, snowboarding was my favorite passion. I used to get so excited when I’d see that snow in the fall. Before I grew up and had to get a real job, I spent one year up at Brighton Ski Resort as a snowboard instructor. I was on the mountain six days a week and teaching usually new people how to snowboard.

How to carve it up, right?

Yeah, or make it down the mountain safely. It’s either way.

Not to get pulled down the mountain in a toboggan.

There you go.

For those who don’t know where Brighton is, Brian lives and works near the beautiful Wasatch Front in Utah. What is it? Is it the greatest snow on Earth or something like that?

Greatest snow on earth. Especially in 2022, we’ve had an incredible snow year. It was good.

That’s a little bit about Brian personally. Aside from that illustrious career as a snowboard instructor, you spent the rest of your working time in JourneyTEAM. That’s not a business that you started. Is it your father that started it?

My dad started the company in 1993.

It has been 30 years. Did I get that right?

Yes. We’re 30 years this fall 2023.

You’ve been working there since 2003, so 20 years for you. You’ve helped grow this thing from a small team of 8 people to 150-plus or whatever. That’s amazing. Congratulations to you. Let’s get to the meat of this where everybody wants to know, “How did he go from 8 people to 150?” This has nothing to do with the market you’re in, the technology, the sales and marketing, or the positioning. All of that is super important and I congratulate you for figuring out all of that, but we want to focus on your journey as a seven-figure CEO.

You are growing a business from a relatively small team to teams of teams. You have a large organization, or a relatively large one, and have to figure out how to make those transformations personally and as a business. If you think back to those seven-figure challenges, what sticks out to you as 1 or 2 of the key things where it was like, “That was such a sticking point for me or for us collectively. We had a hard time getting through it.”

Probably a lot of those sticking points have been me, honestly. One of the hardest things I learned through that stage was letting go at different times of different things. When you start small, you get to wear all the hats. You get to do all the things. I loved being hands-on. I loved being on projects. I loved selling. I loved doing all those things. At each of those stages, letting go was hard for me. I’ve gotten better at it now, but it’s been through that experience of almost having to do it by force to get to where we wanted to go as an organization that I learned how to do it.

Early on, I was our main salesperson for years. There was a stage where I had to let go of sales and bring in some other salespeople. That was hard because I loved that customer interaction. When you’re building a business, you’re also so dependent on revenue in those early years. In a lot of those early years, you’re scraping by to make payroll. You know that that revenue has to come in. Having that control to some degree of knowing, “I know I can go close some deals. I know I can go drive revenue to get what we need as a business,” gave me a level of comfort and assurance that was hard to let go of.

Having your hands squarely on the wheel of revenue production is one of the hardest things for business owners to let go of. I’ve heard you talk about not only that letting go piece or how difficult that is, but also how rewarding it is. You used the term dopamine hit. Talk a little bit about the dopamine hit of producing results.

For me, at least, chasing a sale or closing a deal is super fun and rewarding. You get a dopamine hit every time it happens. It’s a high reward. It’s super exciting. I had to change where those dopamine hits were coming from. As I shifted from individual contributor to contributing through others, and then contributing through other leaders eventually, each shift required refocusing on where I got my reward, my win, or where that dopamine came from.

I had to learn that it was fun and exciting to see someone else close a deal and see them have that success. It was awesome to see someone else take over the leadership and responsibility, role over that revenue, and see them start to make changes and improvements, and drive things in a way that helped us as a business progress past where I could take it.

The thing about that journey or that transition is every time, I was scared to do it because I didn’t think that we would do as well. Every time someone comes in to replace me in a role, they’ve always taken it to new heights and done better than I ever could have done in that role. Sales have certainly been one of those areas where as I handed off sales to better salespeople, and as I handed off sales leadership to someone who had more experience leading sales teams and running a better sales organization than what I had been in, having always grown up in JourneyTEAM, they do today what I never could have done.

I want to unpack that a little bit more. In fact, I’m sitting here and struggling to keep my mouth shut as you talk. This is all so natural to you. It’s like, “Here’s all the stuff in this journey. Here’s what we did.” I’m like, “There’s another tidbit. There’s another nugget.” There’s so much rich perspective in this gold that you’re dropping there. Let’s back up a little bit and try to catch some of it.

One of the things is in this process of being able to let go, I imagine that part of that was being able to maybe first find somebody that you think could take that for you, and then go through some kind of process personally to be able to trust them. Could you unpack that a little bit? What did you have to go through together for you to be able to hand that off?

That’s probably a great call-out because I take it for granted. I’ve got some of those people in place, but that wasn’t an easy process. It did require first finding the right people. I had to learn how to better find talent and how to better evaluate talent. Even once you find that talent, how do you get them ready for that next step? How do you set clear expectations, and then how do you help position them to lead it? How do you trust them and get out of their way so they can do it? That might have been the hardest part of that.

First, you have to learn how to find the right people. And then once you find that talent, you have to learn to set clear expectations and then trust them and get out of their way so they can do it. Click To Tweet

We’ve talked a lot about finding in the past. It’s probably the thing that I’ve done best for our company. Probably my superpower is finding talent and recruiting talent to come to JourneyTEAM. There are a couple of things that I learned along the journey. One, I’m always watching for talent. Everywhere I go, I’m looking for people that might get aligned with what we’re doing, be passionate about what we’re doing, and want to come join our cause.

A lot of the people I found that took over leadership roles, I found through connections. It was either through my best friend from high school or from someone who lived in my neighborhood when I was first married, and that was in the same industry that I connected to. Those were two of my first early sales leaders. It was through someone I met through a user’s group and a related technology community that we connected with and brought him in. He’s our COO today.

I look for people who show three things. I look for people who are hungry who are taking on more opportunities and looking to grow, do better, and do more. That hungry piece is critical. I look for people who are humble in that they realize they don’t know everything. They treat people with respect and are easy to get along that way. I look for people who have good communication skills or soft skills. They can relate to people and communicate with people clearly. The last one I throw in there sometimes is people who care about more than themselves. Those are people who can care about the cause, the team, and the customer. It’s not just what’s in it for them.

EEP 142 | Better Business

Better Business: We should look for people who are hungry, people who are taking on more opportunity, people who are looking to grow, do better, and do more.


When I find people, whether it be presenting at something, friends I have, or other things that have those qualities, and maybe have some experience or desire in our industry, I keep a list. I now have a recruiter that does it, but we keep a list internally of, “Here’s someone we think would be great that would fit our culture well.” When this type of opportunity opens up a JourneyTEAM, we know that’s the first place we’re going to reach out.

You’re always looking for great talent. This is a little self-serving and I don’t mean to do it this way, but I think there are three main roles for a seven-figure business owner. The first is to set the vision and get clear. Co-create a future with your team. The second is to build the team. We’re talking about that right now. I love that you’ve taken that on. It’s like, “I had to learn how to find the talent.” We can all hire a recruiter or put up a “Help Wanted” sign, but you took it beyond those things. You said, “I got to get good at finding, assessing, and attracting great talent because that’s the only way we build a great team to win.” I love that you put so much effort into that.

It was through pain and almost necessity that I had to do it. We’re in a people business. We do consulting, so our people are critical. That is our product. That probably came naturally to me as a need early on, but it has been huge for our growth and success.

You’ve learned how to find people and attract them. I imagine you do a pretty good job of keeping them. We don’t have to get into that right now. Let’s talk about that other part of letting go, which is being able to trust that they have it. What communication, structure, or process do you go through with somebody to be able to comfortably or confidently hand off to them and say, “You have it now.”

I’ve done it right and I’ve done it wrong. Sometimes, it is somewhere in the middle. At JourneyTEAM, we talk about what we call the responsible transfer of ownership. There’s a process we talk about to give someone the responsibility and the ownership of something in a way that positions them for success long-term.

I’ve done it wrong where I say, “I know I need to hand this off. I’m going to do it. I’m too busy,” so I throw it over the fence to someone and say, “Go do it. Sink or swim.” They don’t always swim. I believe that that’s on me as a leader because I didn’t position them for success or I didn’t responsibly transfer that ownership. Those were some painful lessons I learned early on when I tried to delegate.

What would naturally happen is, “They failed. That’s more evidence to me that I can’t let go and I need to keep it,” so I’d pull it back and I’d do it. That wasn’t the case. It’s that I did it wrong. When I do it right, responsible ownership is a gradual process. You got to make sure you have the right people, but then how do you give them opportunities and at-bats that don’t risk the whole thing? How do you give them some growth opportunities that stretch them and push them?

Maybe they fail at them. That’s okay as long as it’s not a complete failure. They can fail at things. You can step back, do a retrospective, learn from it, and say, “What do we do differently next time? How are we going to get better at this?” Continue to give them more opportunities until they’re clear on the outcomes. That’s the other clear piece. You got to communicate outcomes, what they need to deliver, and not maybe necessarily how to do it all the time. To get into how to do it is a last resort. Communicate outcomes and let them own it. Let them decide how to get there. Lots of times, they come up with better ways to do things than how I was doing it before.

Let’s talk a little bit more about those outcomes. I love the phrase responsible transfer of ownership. You’ll find this to be true as well. I’ve met tons of business owners and tons of small business leaders who say things like, “If only I were better at holding others accountable,” or “Why can’t they be more accountable?” It’s like we want to throw this accountability word around.

I found that if we do this responsible transfer of ownership thing, accountability comes with that. Clear ownership is what yields good accountability, but we often fail as leaders to do that responsible transfer of ownership. I’d like to get as practical as we can here on the outcomes piece because the concept is awesome. I’m going to give clear ownership to somebody. What does that look like? When you talk about outcomes, are these measurable KPIs that then they own and you can both see the scoreboard together? It’s not the how. You said, “I’ll leave the how up to them.” What does that look like?

I’ve done it a bunch of different ways. When we do it well, we have very clear KPIs or measures that we can watch. We can see when we’re off track or on, and then I can offer help and assistance if they need it. I’m never letting go because, at the end of the day, I still own all outcomes. I’m there to help make sure they can be successful. We’re watching on a weekly, monthly, and quarterly basis what the right numbers are that tell us where we’re at and what are the right measures, whether it be behaviors, actions, and results that show what we need to be accomplishing for that role.

Do you have any favorite rhythms, mechanisms, or frequency for checking in on that accountability?

We’ve developed a cadence of accountability. That is what we call it. Each of our teams meets once a week in a rapid-fire meeting where we review KPIs and make commitments on what needs to happen during that week to help with KPIs. As a leader, I can see where my teams are at on their KPIs in one quick meeting. Other team members or I can offer to help if we need to where we make commitments for what needs to change. That’s one of those cadences.

We do a one-on-one every two weeks. It’s a 30-minute one-on-one of where they’re at, how they’re doing, and things that I’ve committed to do to help them or things that they’re working on. I help strategize on what they need to do. We then do a larger quarterly plan with those individuals as well to talk about, “Where are the development and growth areas that they need to work on? What are the outcomes that they want to change over the next quarter? What’s our plan to get there?”

You have a weekly team setting for the dashboard like, “How are we doing against the ownership outcomes?” You’ve got the one-on-one, and you do those every couple of weeks. You have a quarterly review, planning, or development plan type thing that you do as well. Those are great. Whatever the rhythm, I’ve found that the best leaders and best businesses have their rhythm for making sure that everybody is on the same page. They’re giving people the individual attention that they need from a development standpoint and checking in on the ownership standpoint. It sounds like that’s what you’re doing.

I left out a couple of those rhythms. We do an annual strategy planning. We set a strategic initiative for the year, and then we have quarterly leadership check-ins on those as well, where we review KPIs and progress on the strategic initiatives. We have a quick monthly check-in on that stuff as well as a leadership team in addition to that rapid-fire.

That makes total sense. I know why you separated those because we started off talking about that transfer of ownership to individuals. There’s the strategic progress side of the business that you brought in so beautifully with the annual, quarterly, and monthly check-ins. That’s very good. I could talk to you for hours. I’m geeking out. It’s probably like you guys talking with somebody about their technology needs. This is my technical geek-out time.

This is my area too. Nowadays, I’m totally hands-off on the tech stuff. I’m probably the dumbest person in the company when it comes to technology. I had a hard time getting my camera working when we started this interview. I love the business stuff.

That’s good. I don’t know where you were when you started, but I can tell you have a level of mastery around this stuff that’s fun to talk about. I’m going to call out one more thing in the time that we have left. In that $1 million to $10 million, you might not remember the exact point in time, but I’m going to offer it up. It’s probably somewhere in the $3 million to $5 million range. You had to put together a leadership team. Before that, you could hold all the parts together yourself and oversee everything. For sure, by the time you get to $10 million, you got to have a fully built-out functional leadership team.

We’ve already talked a little bit about finding the right talent. What I’d like to spend a little bit of time on is you are starting to bring in a higher dollar and higher horsepower executive leadership into what was a smaller business. That’s a new dynamic. We got new senior people. Not only is that new for us in general, but we got to bring them together and have them work together well as one team. Can you talk to us about what you learned about building that executive team?

There are probably a couple of key lessons there that stand out. The first is the importance of having a vision and a purpose clarified to rally around. I remember early on when we were small, we were in that probably 15 to 20 people and were scraping by. I remember David told me one time, “Eventually, it has to be about more than the money.” I remember thinking, “I can’t think about anything other than money right now. I got to make payroll on Friday. It’s very much about the money.”

One of the most important things in business is having a clear vision and purpose for everyone to rally around. Click To Tweet

As we grew, it had to become less about the money for a lot of reasons. A lot of it is people don’t get driven and excited as much about the money. They get motivated and driven by the purpose. The purpose is what unifies the organization. It’s hard to keep an organization unified around money. Personally, I’ve gotten a lot more fulfillment as I’ve focused more on that purpose or why we exist and the good that we’re doing for other people. That’s one thing. That vision was critical to aligning a leadership team.

EEP 142 | Better Business

Better Business: Vision is critical to aligning a leadership team.


You threw David’s name out there. He’s familiar to both of us. David is my brother. David and Brian have known each other for years and have done some work together. David now works with me. For those of you going, “Who’s this David guy,” that’s who that is.

The other thing was understanding the importance of investing in talent. When you start to build out that leadership team, you need some high-performing players who, to some degree, are only going to take offers or be motivated if there’s enough compensation there. Early on, for us, that was painful and hard as we didn’t have the revenue to always support it. I was learning to view that as an investment in the business and was willing to pay someone at the time quite a bit more than I was making or quite a bit more than I was pulling out of the business.

I was going to ask if you paid somebody more than you. I didn’t want to put you in that uncomfortable spot, but it requires that.

Many times, it requires that. I had to look at it as “This is an investment in the business. In the same way, I was going to make an investment in a stock market or some other deal, I’m going to invest in my own company. I’m going to pay this person to bring them in to help us get to where we want to go.” Probably 5 or 6 times at least, I brought in leaders into the company that I paid way more than I was making at the time, but it paid off well.

It helped us take the organization where it needed to go. It helped take a huge load off of my shoulders from a stress standpoint and a leadership standpoint. To have this part of bringing in those people so you can hand things off, you got to have a level of the person that you can trust that you can transfer that ownership to that they can run with it. You got to comp them well.

That’s very well said. To wrap this up, you said something about the weight that came off of you when you hired those good leaders because of how much they were able to take that translated directly to less weight on your shoulders. Listening to 150 people and growing feels like a ton of weight, especially when 8, 10, or 12 is crushing them.

With 8, 20, or 12 people, it’s like, “I can’t carry all this.” You’re now doing that with 150 people. Logically, we can go, “You have all these leaders. They can carry the weight.” Could you try to put some words into what it’s like to unlock the power of building a great leadership team and what that means to you personally in terms of the weight that you’re carrying?

I don’t know that I feel maybe necessarily less weight today. The weight changes, but things are easier than they were in that $3 million to $10 million or especially that $1 million to $3 million range. I don’t have to do some of the things I had to do in those early stages anymore because I have a team to support me. I don’t work as many hours anymore. I don’t have the same stresses.

When there are problems that come up, I feel like I’ve got people who can tackle those problems with me. It’s nice because I can handle a lot of those problems. I’ve got good enough people. I’ve got an amazing team. It is incredible the way they have learned to clear roadblocks, take things on, and solve problems in a way that it’s way better than what it used to be.

I get hit up with offers all the time to sell. I’m sure everybody does. Most of your audience is getting hit up with people who want to buy their company. A lot of times, I can’t imagine starting over again and putting in that level of work, stress, and effort to get back to where we are at today because it’s so much better where we’re at now. It’s so much more enjoyable.

If I could piece the parts together through our conversation, it sounds like the before and after. Back when there were 8, 10, 12 of you to 20 times that now, you didn’t say more weight, but it was very stressful. You were making less money and working more hours. The whole thing wasn’t as enjoyable. Whereas now, you said you’re working fewer hours. You alluded to making more now than you did then. You’re talking about having this purpose-driven thing that’s much more enjoyable. You have fun building the team and working with those people. It’s a different game. It’s not one that you want to go backward to. You don’t want to go start up again.

I don’t know if I’d have the energy to go do it again. It’s not that everything is sunshine and roses at this stage either. We still got tons of problems and things we need to do better. There are stresses. If you catch me on the right day, I might sell the whole thing for $100, but it is putting the investment in the business and putting the investment into people. Learning to let go of things has certainly paid off from a fulfillment, satisfaction, and quality of life standpoint.

Brian, this has been magnificent. Thank you for spending your time with us. For people who want to learn more about JourneyTEAM or connect with you online on social media or wherever, what’s the best way for them to do that?

JourneyTEAM.com is our website. You get to stuff there. I’m on LinkedIn. I’m not super active on social media, but you can email me at Brian.Tenney@JourneyTEAM.com. I’m always happy to talk.

Thanks again. It was magnificent.

Thank you.

For everybody out there, please keep tuning in. Share and like, and do all those things so that we can help as many seven-figure business owners as possible learn from all these amazing guests that we have in every episode like Brian. They’re sharing their real experience and very practical great insights. All of them would say, “If I can do it, so can you.” keep at it. You can do it. We want to help you as much as we can. Thanks for tuning in. We’ll see you next time.


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About Brian Tenney

EEP 142 | Better BusinessBrian Tenney is the Owner and CEO of JourneyTEAM, a technology and business consulting firm specializing in Microsoft products and services. Since retiring after one season as a snowboard instructor, Brian has been working at JourneyTEAM since 2003. He has served in various roles during his tenure including: marketing, sales, project management, technical consulting, and as COO. Brian has played a pivotal role in the growth of JourneyTEAM, helping the company grow from 8 to 150 employees. Brian finds joy in his role developing his team and celebrating with them in their successes, as well as working with clients and being a part of helping them grow and improve their organizations. As CEO, Brian has one specific purpose in mind, helping organizations simplify and effectively use technology to help create a positive, lasting impact.

In his personal life, Brian enjoys spending time with his wife Erin, and their five beautiful children. They stay busy by attending various kids activities, and spending time outdoors: boating, wake surfing, snowmobiling, and any other fun outdoor activities they can do as a family. If you would like to get to know Brian better, ask him about his passion for employee development and organizational growth or wake surfing!


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