How Can I Serve You? With Greg Greenwood

Sep 6, 2022

Leaders need to look for ways to serve their people and build a trusting workplace to elevate performance. Greg Greenwood talks about the value a “who are we” statement can bring to your business.
HITC Greg | Serving Others




Our guest has a mantra that I believe all of us entrepreneurs and founders can benefit from and should adopt. Greg Greenwood has a philosophy and a mantra of, “How can I serve?” He has served so many entrepreneurs and founders over the years with his incredible business acumen, his kind of spirit and his gentle way. I was one of those recipients back in 2017. I had a terrible tragedy and my business was on the point of bankruptcy.

At the time, Greg and I were strangers and even as a stranger, he reached out and said, “How can I serve?” I wouldn’t be here now if it hadn’t been for that moment. Greg is the Founder of so many businesses, I don’t even know where to begin. He has been an entrepreneur since the ’90s to weather the dot-com boom and bust.

He was back on the battlefield and weathering another recession in 2008 and 2009 and thought, “Maybe we need to go about this different. Instead of feeling like we had to compete, what if we came together and served each other?” Sure enough, all those businesses survived, including him and he ended up building a community out of it.

This community came together for me and it came together again during COVID. We were all able to help support each other through those hard times. I feel honored and almost a little bit emotional to introduce my friend, my brother from another mother, Greg “Woody” Greenwood. Welcome to the show.

Thank you, Kendra. It’s a pleasure and an honor.

Let’s talk about your journey. Tell us the backstory. What were you like as a young entrepreneur?

Success is a great encourager, while failure is a great strong educator. Click To Tweet

I was overzealous, to say the least. Aspirational, idealistic, hopeful and aggressive. At times, too aggressive. It worked for quite a while until it didn’t and that’s where the lesson started. It’s because success, I’ve learned over time, is not a great educator. It’s a great encourager, but failure is a strong educator, especially when we sometimes don’t see the warning along the road. There’s a lot to it. That’s the beginning.

What were some of your biggest teachers in failing?

The one that has repeated itself a few times that has gotten in my way until the last company I built, by accident, was being fully transparent about what was going on in the business. In the first iteration of my IT infrastructure business building, we caught this wave of networking connectivity and anything we touched made the wave bigger and longer. It was fun. When we had our first hiccup in the late ’90s that you alluded to, I started to realize, “What got us here isn’t going to get us there.”

I was forced to look in the mirror around who I was being as a leader. I was into doing and micromanaging and a little bit too much oversight. The doing got in my way and through that a-ha, I realized in my next business-building experience that I was going to back up, create space and provide resources, encouragement and clarity. Also, give people the autonomy to perform. In those two lessons, I saw something flourish under people’s power versus my own struggle to harness something myself.

When we start a business, we feel we have to do it all because it’s our baby, but when we hire people, they want to do great work too. They just need clarity on what is it that’s expected of them. Tell them the goal, budget, resources, timeline and the general direction you want him to go. Course-correct a little along the way, but let them go do it their way. It might not be our way, but their way may be even better.

When they get ownership, I’ve found that they achieve more than expected. They find some efficiencies that can be leveraged across the organization, which is fun when the team starts to take better practices amongst each other, like the old saying, “All boats rise.”

HITC Greg | Serving Others

Serving Others: Be a leader who’ll back up and create space for your people. Provide them with encouragement and give them the autonomy to perform.


What were some of the demons that you fought along the way in terms of transparency? What were some of the things where you’re like, “I don’t know if I should be transparent about that,” and then you tried it and it worked? Do you have any examples?

Yes. It’s more around strategic direction long-term where we’re talking about partnerships or capital raising or exit strategy. I held that too close to the vest. At times, I masqueraded as what it was and used language that was clear but confusing. What I’ve learned since then is to tell everyone the truth all the time. They can handle it and they can hold confidentiality if you ask them to and trust them. It’s the big difference in my post-SpiralMethod life versus my pre-SpiralMethod.

Life is this container of confidentiality where we build trust, deepen the relationship and we elevate performance through full transparency, authenticity and vulnerability. It’s sharing the truth even though it’s scary. I was scared. I lived with fear for a long time around information sharing. You know my story with CTLF and Blackstone. If everyone knows, that’s all the better as long as they know what’s team-only and what can be shared outside of that. That’s the clarity I’ve tried to provide after those lessons.

What is it like for you when you sit down as a mentor to someone like me? When we sat down with the group back in 2017, you were all so generous and called to serve me even though we didn’t know each other at al. What was that experience like for you? Give me insight into what it was like to hear my vulnerable story and see the fear. You’ve done this with so many people over the years. What goes through your head in those moments?

It’s one word, empathy. Father told me if there’s one thing I give you and he’s told me so many things, but the one thing I remember around this was put yourself in other people’s shoes. If you can understand that, then there’s a connection or alliance. What I was thinking was, “I know you look fearful, scared and about to raise the white flag.”

I’d been there. I raised the white flag and I was like, “You’re not even close to the white flag. You’re doing great. Let us help you get a few things in order.” I remember Mike Larkin and being in there and being a tremendous White Knight for year-round sales, sales funnel and prospecting. It’s going to be okay because I’ve been here and it’s tough, but it’s not the end. Even if it’s the end, it’s not the end.

We Wave is an initiative to spread kindness and connection on life's trail, wherever you are. Click To Tweet

You have founded so many businesses and now we’re on a new one, which I want to talk about here. Do you think it’s fair to say that as an entrepreneur, you were always on the rollercoaster? You never get off of it. It never gets to a place where you feel like you can just cruise. It’s going to go up and down always and it’s how you weather those downs that make the ups possible. How do you feel about that when I say that?

I think it’s mostly true. I will say the more that I didn’t do, delegated and became more of the being leader versus the doing leader, I did find some coasts and I don’t mean coasts like, “We’ve made it. I mean like, “I’m in my office. Everyone’s doing what they should be doing and then some. What do I do now?” I remember Andy Work who was our VP of Product and Technology. I’d come in and go, “Do you need me to do anything?” He goes, “Yes. Go ride your bike and think of some cool strategies for where we can go next.” I’m like, “Okay.” That’s the only moment where I felt like, “It’s not an up or a down. It’s a slow rise.” Yes, as soon as I deployed one of those strategies, it got scary again.

We started going up. We had a failure. “Pull the reins in.” We are looking at the financial projections going, “We can put a little bit more towards this to see if it’s going to rise or not.” It did or didn’t. We decided to or not to. I live a little bit on that fringe, anyway. I liked the edge, that little bit of fear and not without caution. With a little edge that says, “We’re making a difference here. This is exciting.”

You got to have some reason within that and good people around too to keep the lows not being too low and the highs not being too frothy in realizing that there’s no good grounding underneath them. Because sometimes the market pushes us without a lot of our own effort. Our timing can be good and be like a false foundation underneath us. I think you’re mostly right. It’s cool when you’re not a little bit of coast while there’s a little bit of a rise.

One of our fellow CEOs says, “The sign of a good CEO is somebody who could go on a lot of vacations and their business thrives.”

I never got quite there, but close.

HITC Greg | Serving Others

Serving Others: Be clear on your “who are we” statement so that if something goes wrong, just go back to the statement and look where there is a misalignment.


It’s having that good team in place that has the autonomy and the clarity. Who knows what they need to do and feels that trust from you. All of those things got you to that place of being able to coast a little bit.

I think there is a bit of a secret formula that I worked with my business group around this, which is that clarity and alignment. What we’ve developed in the 2008 timeframe for comCables was a, “who are we” statement. “Why do we exist? Where are we going? What’s our mission? How are we going to do it? Who are we going to be while we’re doing this business and go in that direction?”

What I found is that if the people have clarity around the who and the who is a belief system to value set. It’s an alignment of an agreement that this is who we’re going to be in this business that we’re in. When that’s clear, if something goes wrong, we come back to that agreement as I say, “Where are we out of alignment? What what’s missing? Did we sacrifice a belief or a value? Did we get off course to where we’re going? Did our goals get misaligned? Did we chase something that was not true to our goals?”

If that’s there, that’s the culture element and when we’re bringing new people into it, that’s what we’re sharing. The job is clinical. The who part is so essential. When you are adding new team members, having real clarity around those things I described allows us to add people in a really powerful way and the team happens because we’re aligned before we start.

Tell us what you’re doing right now. Let’s go through your history a little bit because you sold your business. You had an amazing exit. All of us founders want is that amazing exit. It was a rough patch to get there, but let’s start there. What happened when you were able to exit? What did you do after that, then?

You said it was an amazing exit. I’ll say this. It had a strong financial component to it. Not magnitudes but enough because my wife at the time and I agreed that we wanted to focus on our marriage and our family and our future versus the business. Both were a little bit in crisis. We sold 60% of the company to a private equity group out of Boston. They talked us into a platform company.

Serve others by just acknowledging them with a wave or a smile. Click To Tweet

It was a very large business and they were hell-bent on their exit. They had a certain EBITDA. They were chasing a certain multiple they wanted to get. They had certain buyers that were already there. Our belief systems and our values did not align. Even though they said they did, when it came down to day-to-day actions, it didn’t. Less than a year later, they made a very aggressive move. They fired my wife out of their agreement that I could operate the company as long as we were on target and inside budget, which we were.

I held up my commitment to my relationship over staying with the company that I’ve built. We left the company very abruptly. It’s very difficult. They bought us out of the balance of our position in the company within like three weeks. I called Leslie Jones, my now partner and said, “I’m not okay.” The balance sheet looks great, but my emotional and psychological state is not okay. My mental fitness was not well. With that, I leaned on her and you might know the story of bringing a number of people around, sitting in a room in Golden Colorado, helping me create a closing around that chapter of my life from an emotional standpoint.

We put a bow around it, cast it off from the dock, and let it go so that a new future could happen. That session with Leslie and a lot of friends became SpiralMethod. That was the iteration of how to moderate a facilitated group in a way where we deepen trust, deepen the connection and build relationships for a lifetime. Through that, team performance elevates. That SpiralMethod. It’s crazy how it all happened. I would have never known it was coming to this.

SpiralMethod is amazing. You also have a new business as well, We Wave. Tell us about that.

We Wave is, by definition, a for-profit because it’s very difficult to manage the not-for-profit 501(c)3 and we’re probably headed there. We Wave is a movement. During the pandemic, we were pulled apart and putting masks on. We were avoiding each other in grocery stores on sidewalks. It got to me. As a very people person oriented human being, I struggled with it.

As you know, I love to go mountain biking, hiking and going out on the trails. We’re saying hi to people because it was exciting to see someone else. Some people were like, “Why are you talking to me?” We’d come home and go, “People aren’t as friendly as they were. How come they don’t wave back? We’re only trying to say hello and create a connection.”

HITC Greg | Serving Others

Serving Others: The Spiral Method is to moderate and facilitate a group in a way where trust and connection are deepened, and relationships are built for a lifetime. And through that method, team performance elevates.


I went out for a mountain bike ride 1 or 2 weeks later and I came back. I’m like, “The same thing happened. I see these mountain bikers and we’re all sharing this common interest, but I can’t get engagement. I’m waving. It’s easy like, ‘We wave. Let’s wave.’” It became this thing where we’re like, “Let’s put it out in the ether.” We Wave as an initiative to spread kindness and connection on life’s trail, wherever you are, the sidewalk, hiking, boating, biking or skiing, you name it. Acknowledge one another through physical acknowledgment and look at each other with a smile and a wave.

Bridget, my wife, has been an amazing supporter and she’s a writer. She’s writing these incredible stories about inspiring people that do great things in life around human connection or whatever they’re trailing like this. Also, Paige, our cofounder, is running the back office of it all. She is putting some products together so that we can proliferate this message wherever people go.

What can we do for you as a community? How can we now serve you?

I think it’s about serving one another once again, but just wave and acknowledge each other. Take a minute. We have a little icon. This is designed on 99designs. Spread kindness and connection on life’s trail, wherever you are, because physiologically, there is science behind smiling, grinning and acknowledging one another that’s good. It builds immune system strength as well. I would say spread the wave. Not the serving wave, but the kind wave.

Was there any final nugget you’d like to leave with our audience other than that beautiful waving and creating a connection together? Any final words for our fellow entrepreneurs and founders in terms of what they can do for their folks, their people?

One element that’s served me significantly throughout my career and I got it from a fellow entrepreneur back in Arkansas before I moved out West in the ’80s, was to surround myself with peers, be in a community and be authentic in that community. It started for me in YPO, then Vistage, and CTLF. Now, the group through the SpiralMethod. If you don’t have a bunker of people you’re being real with and you can talk about any challenge you have in your life, not just business, get one and stick to it. Show up, be on time, stay until the end and be real because there’s magic in-depth with the connection.

Greg Greenwood, thank you so much for your time with us. We can always benefit from more wisdom. We’ll reach out again soon and get an update on how everything is going with SpiralMethod and with We Wave. We will reconnect with you again to see how you are.

Thank you so much, Kendra. It’s been a pleasure to spend some time with you and hopefully, it’s valuable to everyone that comes along and witnesses it. Thank you for all the great work you do.

Thank you.

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About Greg Greenwood

HITC Greg | Serving OthersHITC Greg | Serving OthersGreg Greenwood (nicknamed “Woody” since childhood) is the CEO Emeritus of BEN Colorado. A veteran Coloradan entrepreneur, Greg has founded several companies including those in technology, manufacturing, distribution, motorsports, retail, services and non-profit—and like all entrepreneurs, has seen a variety of successes and failures to keep him humble. Greg’s entrepreneurial energy was passed on to him by his father at the age of eight years old when he started his first business mowing yards and selling hanging baskets and bags of kindling firewood in his Little Rock, Arkansas, neighborhood.

Greg most recently sold comCables, a network infrastructure manufacturer and low voltage distributor he founded in 1999, to The Audax Group, a multi-billion dollar private equity firm based in Boston, Massachusetts. He is the founder and CEO of Idella Wines, a boutique winery in Napa Valley, California, and is the co-founder and CEO of Colorado Thought Leaders Forum. Greg is a current Board Member of Wish for Wheels, serves on several private company boards of directors, and is a former board member of Colorado Companies to Watch. While Greg is passionate about his business endeavors, his other life interests include building community relationships, investing in inner-city-at-risk youth, cycling, SUP surfing and enjoying wine.