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About Wil Armstrong

He is an entrepreneur and small businessman whose business background includes start-ups, executive leadership, and active investing in the areas of technology and financial services. He has served as a board director, C-level officer, investor, and advisor to dozens of different businesses. 


Wil is presently Chairman and CEO of Three Tree Capital, a privately held investment company and family office focused on venture capital, early-stage growth companies, and private equity.


Wil believes that growing and developing your team supports the bottom line and growth of your company, and that culture and competency are critical in venture and private equity investing. He places high value on always learning, finding ways to create value for others, and having something bigger than yourself as a purpose.



In this episode, Steve and Wil discuss:

  • A gift and an attitude
  • How to nurture gratitude
  • A winning mindset
  • Making a difference in the world



Key Takeaways:

  • The spark of gratitude is a gift, but there are a lot of ways to nurture it; it is a discipline and an attitude.
  • Here are some things you can do to nurture gratitude: Be humble and ask for forgiveness from who you need to, and write down things you are grateful for both in mountains and valleys.
  • Being able to find success in your career is all about working hard and working smart, being well-prepared, and being a lifelong learner.
  • Make a difference in the world and the lives of people around you, even in small unseen ways. Seek wisdom, and dive deep within to understand who you’re serving.



“Some people think, ‘I’m done with school, so I’m done with learning,’ and I think that’s a recipe for disaster if you seek to prosper in your career. I do think that being an active learner is crucially important.” - Wil Armstrong


Connect with Wil Armstrong:




Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 





Listen to the podcast here


Wil Armstrong: Abundant Mindset

This episode is particularly special for me. It's not often that I get to do an interview with somebody who I think is not only one of the kindest, most thoughtful people that I know but also someone who I've called a friend for many years. I'm eager to be able to draw up some insights from my friend, Wil Armstrong.

Who's this guy you're talking about? I want to hear from him. I don't know what you're talking to me for?

He wasn't available, so we're talking to you.

Thank you.

I am quite excited to dive into this. When I say I'm excited, like you, I've been doing this for a couple of years. Quite honestly, I'm a little nervous. That comes from not really knowing some of the roads that were going to go down. It's partly my job to find thoughtful, insightful people, bring them on the show, and see where it goes.

To that point, Steve, I've certainly enjoyed your show with Jason. It has been insightful to me. I know you're over 100, and so congratulations. I think I told you that before, but it is. It's an encouragement to me. I'm grateful for the work you're doing.

That's very kind of you. As I mentioned to you here, you were one of the first people that I invited onto the show. It's just with our lives and your life and what's going on, it didn't happen until now. That's neither here nor there. It's happening. We're in it. Are you ready to go?

I'm ready.


Life is such that we don't always have. We aren't always happy, but to be thankful and have a spirit of gratitude, is a gift.

There is this concept, Wil, in the greater field of neuroscience that I know you've heard of. It's the concept of having flow. It really stems from the field of positive psychology. We hear it a lot of times in the realm of sports when somebody's in the zone. That's a similar thing to being in flow. You're with me so far?


I know enough about you to know that from time to time, you find flow. Here's what I want to know when you feel that in your life, wherever it is, however it is, what brings you there? What brings you to that feeling of just flow state?

For me, I am an outside-in person. In many ways, I wish I was an inside-out person. What I mean by that is that if my outside world is crazy and nuts, it makes it hard for me on the inside. I'm pretty diligent about trying to care for my inside, my soul. I'm an early riser. I like to read the scriptures in the morning, have quiet time, and often come to the office early and endeavor to have time to work and think. I'm a thinker, and that cares for my insides. When it relates to my outside world, when I'm not organized when I have big challenges that I've not had the time to think through, and so forth. When I'm able to sort of bring both of those together, that's when I have flow.

I'm always hoping this for the show that when people read some of the things that you're saying, and I'm asking about and whatever, is that people have their own insights. Little do people know, I just wonder sometimes if this isn't just for me. I don't know that I've thought of that like that. I literally wrote down the question, what am I doing to care for my inside world?

I'm sure I've thought things like that, but not in that context. I'm really grateful for that. Thank you. In your life, we got to get to who you are and why the heck you're even on our show here, which people that are going to be, “It's a cool thing.” One other last question for you, and that is, what are you thankful for in life?

On that question, the ability to be thankful, or another way to say this is as it relates to joy or gratitude, not necessarily happiness because life is such that we aren't always happy. To be thankful and to have a spirit of gratitude is a gift. I happen to think it's a gift from God. It's a mindset. I'm really grateful because there are people who have everything in the world, and they're unhappy. I spent time in India, in the slums of Calcutta, with people who had joy and gratitude even though the world would say they have nothing.

My first reaction to that question is I think it's a gift and it's something that can be nurtured. Steve, I'm thankful for you. As I was thinking about our time together, I'm reminded that we met during our sophomore or junior year in college, and we've been friends for a long time. In fact, you've been a great friend to me, you've walked through very challenging times in my business life and my personal life, and I'm thankful for that.


Graphics - Caption 1 - TII 116 Wil Armstrong

Abundant Mindset: America is still the great shining city on the hill. It's a country where freedom and personal opportunities still exist.


I'm thankful for my family, my wife, and I married way above my head. She has been a tremendous encourager to me, a great soulmate. My kids, challenges and all, are a blessing from the Lord. I’m grateful and thankful for the country that we live in, even with all the problems, the divisiveness, and the strife that is going on in our country, America is still, in my view, the great shining city on the hill. It's a country where freedom and personal opportunities still exist.

When we see what's going on around the world, I'm thankful that God placed me in America. My great hope, and what I'm most thankful for, is Jesus. I realize this isn't a religious show, but I'm a person of faith. To understand, as I do in the Christian tradition, that I'm a sinful person, but before God, I can stand because of the blood of Jesus. I'm enormously thankful for that. That's an encouragement to me.

You're right. We don't have enough time for you to list all that stuff out. Wil, I'm thankful for that. So many things that you said there. This is why I don't come into this with all these questions. I never get to them anyway. There were so many. By the way, thank you for Kelly. I'm rattled by all that. That's really wonderful.

There is something that you said I'd like to go back to because it felt like a little bit of a paradox to me. I don't know that we need to spend a bunch of time with it because I still want to get to who you are, where you came from, and what you're doing. If thankfulness and gratitude are a gift, and then later on, you said it could be fostered. If it's a gift, and someone doesn't feel thankful or doesn't feel like they got that gift, how would you help them foster that?

There are a lot of things. I don't always walk around feeling grateful, thankful, or joyful, but the kindling of it, the spark of it, is a gift. If you run across successful people all the time, I'm always amazed at the people that I meet, who literally have everything in the world. They're flying around on private jets, they drive expensive sports cars, and fundamentally, they're not happy. They don't have joy. They're not grateful.

I do think that the spark of that is a gift. There are lots of ways to nurture it. The first is to, in humility, make sure you have clear accounts with people. It's hard to be grateful if you're arguing with your wife, and you never asked for forgiveness, if you never express that you may have wronged your spouse, your friend, or your kids. The first part of that is perhaps confession. I've done things along the way where I kept the journal. I've kept a journal for probably 20-plus years, but in seasons when things were challenging, I would actually write down things for which I am grateful. That's pretty powerful.

When you go back and you look at things that happen in the past, if you're in a valley, if you can go back and look a few months or a few years before when you were maybe on top of a mountain, and remember that, that's powerful. A lot of it is attitudinal. It’s like I'm going to work out or I'm not going to work out. I'm going to try to endeavor to find the good in things to have an abundant mindset, and otherwise, be thankful.

That's so good. One of my mentors, Jack Bevilacqua, who has, by the way, been on the show, asks a question, and I'll ask it of you. That is, what are you grateful for today that you weren't grateful for when it was happening?


To be a learner is just an absolutely crucial skill to success. 

I ran for Congress in 2008 and lost narrowly in a four-way contested Republican primary where 70,000 votes were cast. I lost by a few thousand votes. I'm trying to find those few thousand people, by the way. I hate the fact that I lost, but in retrospect, Steve, in many ways, I was able to make a difference in a way that I hadn't imagined on August 13, 2008, the day after my primary election defeat. In particular, it has to do with my son, who struggled in the following years.

If I had been on an airplane 80 times a year back and forth to Washington, DC, from Denver, Colorado, or if I had been distracted by the power of politics game that gets played in Washington, DC, I might not have been able to be the husband and father, my key roles as a man in my life and this stage in life. I wouldn't have been able to be there for my son, my wife, and my girls.

At the time, I hated it. It was it was painful. I put a lot of my own money into the race. I ran a great race. I won with the people that voted on election day. I just lost early voting badly. I thought I was going to congress. It was very disappointing. By the way, I felt like I had the Lord leading in it, too, but the reality was that wasn't the plan. That wasn't what happened. I was horribly disappointed, but as I looked back, even in the last years, at some of those family struggles, I'm enormously grateful that I didn't win. That something better was in store for me. I'm grateful for that.

That's so powerful. I would like to get us to what is in store for you and what was in store for you. If you don't mind, and if you've read the show before, Jason likes to do this. It's a wonderful thing that he does. Sometimes he'll read people's CV and their bio and talk about it. As best you can, if you are going to take 3 or 4 minutes to say, “What's nuts to soup about Wil Armstrong?” What brought you here? What do you do for work? What are the key things that you would tell about us? Get us current. Where are you? Where'd you come from? Who's Wil Armstrong?

I am defined by the family from which I come. I was fortunate to grow up in a household where my folks loved me to death. As it turned out, after college, after you and I met, I got into business with my dad, a world-class entrepreneur. Vocationally, what has really been the great pleasure of my life is to be in business with somebody I admired, respected, cared for, and loved.

To then actually, get out and get to do a whole bunch of different businesses. I was in twenty different businesses with my dad for over 30-plus years, some of which was okay in terms of financial success. Some were unmitigated disasters, and a couple of were just absolutely terrific. That has been my life's work is to be an entrepreneur and an investor.

My business purpose is I want to help other entrepreneurs become wildly successful through culture, competency, and capital. What's been fun for me about that is that I focused a lot of my career on financial services. I was in the mortgage banking business. I've been in the technology business. I've been in the commercial banking business. I'm in a slew of venture capital and private equity investments today. I'm active in the public markets as an investor.

I've always enjoyed finance because finance was the foundation of all business in America. I don't want it to sound trite, but the financiers in our country's history are really what built up America and made America exceptional. This great experiment that we've had and the experiment parenthetically of free enterprise and the markets at work.


Graphics - Caption 2 - TII 116 Wil Armstrong

Abundant Mindset: My business purpose is to help other entrepreneurs become wildly successful through culture, competency, and capital.


Getting to be involved in a lot of different businesses, see a lot of different things, get to know a lot of different people, and learn a ton, has been compelling to me business-wise. It was fun to do that with my dad. Perhaps someday I'll do that with my kids, but family matters. The fact that I got to do business with my family was really a highlight for me.

Wil, thank you. The thing that's come into my mind is, not only have you done a lot of these businesses, what you're not going to say about yourself, which I do get to say, is I find you to be one of the greatest students of business. Being around you, I've gone out to lunches with you, and I thought we were going to get a hamburger, and you're on the back of a napkin taking a note about something. Always be thoughtful about how you capture things. I've found you to be almost a collector of thoughts, good ideas, and good strategy. I don't know if you were taught that, but that's at least something that I saw in you.

You're good to say that. Being a student, my youngest is about ready to graduate from college. Some people, probably not the readers of your show, Steve, think, “I'm done with school. I'm done with learning.” That's a recipe for disaster if you seek to prosper in your career. Being an active learner and being a reader are crucially important, mostly because I know I'm not the smartest guy in the room all the time. Some smarts, but coupled with hard work and being well prepared and understanding, I'm a long thinker. I'm a strategic thinker. It's important to me to have that time to think.

To really be a learner, which is part of the reason finances is so interesting, and particularly venture capital and private equity is so interesting, is just absolutely a crucial skill that has been, to the extent that I've had a measure of success, has been an important contributor to that. It's certainly something I'm trying to pass on to my kids.

I was at a funeral. The person that was being eulogized lived to be 98 years old. They were investors in things. They were a doctor. They had ten children. It was crazy. I was sitting there listening to the eulogy, which by the way, was beautiful. I thought, “How crazy is it to try to summarize a life in just even a few minutes?” How do you do that?

I don't know how we even summarize some of the stuff that you do, Wil. One of the things that I would like to know is that you told me that you're endeavoring to do some radio and video work. I don't want to put you on the spot for that or roll something out before it's time, but it had to do with positivity and optimism, if I'm not mistaken.

You don't have to talk exactly about that, but you and I could sit around. We have, by the way, talked about the war in Ukraine and talked about economic things. There's a lot. I don't want to wax philosophical and certainly, paint some coat of paint over reality. I want to know from you, given all these businesses you're in and how you look at the world, what are you hopeful about in our country?

As you alluded to, that's something that I'm interested in. To your point, it's easy to look out and see inflation. The markets are down, housing challenges, rising prices, harder to qualify for loans, and on and on. The poor are getting poor. For me, it was important to answer your question that I made sure that I was looking up. That I wanted to find ways to be hopeful because people know something is wrong in society and the world. How can we be more hopeful?


Politics follows culture.

A part of that was I wanted to uncover stories that I could tell, that I could learn myself about people that are making a difference and changing the cultural narrative. My father was a political figure. People think, “You're talking about politics.” Politics is important, but politics follows culture. What I was more interested in is how do we impact and change culture? How do we think about improving the lives and giving people hope given all of the challenges that we have? That's something that I have been exploring.

I'm hopeful for lots of reasons. One is I do believe America is the greatest country on Earth. Despite the political divisions, economic challenges, a growing government state, and on and on, it is still the world's greatest country. There are lots to be hopeful about because there are a lot of people, and we'll never know their names, who are making a difference in the lives of the people that they're engaged with.

Steve, you know that I went to work when I was in college. About the time I met you, I spent a summer at Mother Teresa's. Everybody knows who Mother Teresa of Calcutta is. They know that she started this wonderful organization to care for the poor of Calcutta. It spawned out and became worldwide. There are Mother Teresa's Missionaries of Charity all over the world now.

I would argue that there are 1,000s and 10s of 1,000s, maybe even 100s of 1,000s and millions of Mother Teresa's out in the world today that we’ll never know their name, but they are caring for the least of these. They are caring for people, not just the poor, but the poor of spirit, the broken-hearted, and the challenged.

That actually gives me great hope and great comfort that there are a lot of people who really are trying to make a difference right where they are. They're using business. They're using their platform as teachers, doctors, or maybe even farmers and ranchers that are figuring out ways to make a difference in their community. That's inspiring to me. That's encouraging to me. It keeps me looking up.

I've got so many questions that I'm asking myself. I wrote one down, what am I doing in the small, unseen ways to help people? Here I am on a show with you, and we do business and you're this entrepreneur, and I'm running his business and, I hate to say it, Wil, but so much of what I do is a direct attempt to grow influence and be seen. Yet, I wonder if some of the greatest things we do and some of the most thoughtful people are people we’ll never hear. They're not going to be on the radio. They're not going to be in the news. I got one more for you. I'm not trying to ask you anything that's going to intentionally knock you off your guard. Here comes one, ready?

I’m ready.

Your son, just for kicks, we’ll call him Jack, comes to you and says, “Dad, I really want to go into business.” It doesn't matter what the business is, but you have an opportunity to share with him 3 to 5 key principles about being in business that you believe is all that you've seen and read and what you continue to learn. If you were going to synthesize the smallest list you could make of the key things that you've seen to be successful in business, what would you teach him?


Graphics - Caption 3 - TII 116 Wil Armstrong

Abundant Mindset: Our true legacy is not the businesses that we build, the cars we drive, the homes we have, or the trips we take. It's our family. It's the relationships.


There’s not a better question you could ask, Steve, because the reality, you made the point about the eulogies and it's hard to eulogize people. Most people are familiar with the tombstone that has the year you were born and the year you died, and in the middle is the dash. What did you do with the dash? It's quick. Our true legacy is not the businesses that we build. It's not the cars we drive, the homes we have, or the trips we take. It's our family. It's the relationships.

Your question is important because you're talking about my son, and he's my legacy. My son happens to be named after me. He's the fourth and I'm the third. To me, that's super important. Steve, you may know that I'm actually fifth generation father and son working together. We didn't have any one business through five generations. That is a very important subject for that matter as well, with all that you asked me, what were the things that I would teach him? I'm always trying to teach him.

You’re this thoughtful guy. He might be sitting there with a pad and paper he wants to write down. “Dad, give me the nuggets.” I've been to your house. I know what your library looks like. I’m just curious off the top of your head. What would be the 3 to 5 things that you would say, “Do this?”

They may be more simple than you might otherwise think. The first thing to be successful in business and in life is to understand who your master is. Another way to say it is to understand who your Lord is. Was it Bob Dylan, “Everybody's got a master?” You're the song guy, Steve.

Don’t be putting me on the spot. That's my job for you. We're going to go with Bob Dylan on that.

Second, I would say, learn how to love people. In this social media age and the influence age, before all that, the people who were leaders who were able to make a difference and get things done in an organization were the ones who loved people. They knew how to care for people. They knew how to create culture. They knew how to make a difference. To me, that's something that I would teach.

The other thing that I actually have encouraged my son in as well is to read. Specifically, the book of Proverbs from the Hebrew Scriptures. I happen to think that the book of Proverbs is the single best business book that has ever been written. I would presume that ever will be written. It's funny because any one little section from the book of Proverbs will get a nugget that you'll inevitably run across in your day's activity that resonates and makes sense.

What I've encouraged my son to do is to read daily the book of Proverbs. It has 31 chapters. You can read a chapter every day, but fundamentally too, as the elder Forbes wrote, when he began publishing Forbes magazine, seek wisdom. That's important. As we get older, we hopefully garner a little wisdom. Those would probably be the three things that I would say to Jack.


To be successful in business and life is to understand who your Lord is.

In the last couple of weeks, or even just off the top of your head, what individual proverb is something that you've honed in on?

It’s not a proverb, but it's from Psalms, and it says, “Lord, teach us to number our days are right, that we may gain a heart of wisdom.” That was something that actually, in our friendship, you turned me on to. My dad passed away in July of 2016. As it turned out, I happened to be born on his birthday, 30 years apart. I'm somewhat cognizant of the fact my dad passed away just after his 79th birthday. I've got 24 or 23.5 years. I'm not morbid about it. I hope I will have longer. I could certainly have shorter, but I'm cognizant of the fact that the dash on my tombstone is getting smaller and smaller.

What I'm trying to figure out how to do is I'm very ambitious from a business standpoint, I want to be Colorado's best venture investor in the state, but that's not the end game. The end game is that I want to find ways to make a difference in people's lives. It's why I'm involved at Colorado Christian University. It's why I'm involved with our family foundation and our work in India, and our work with business missions like Vivoblu, Water For All and things that are caring for people.

Business is this wonderful platform that I've been able to use and for the good of my fellow man and for the glory of God. By the way, I see you doing that and I see lots of people doing it. People in the mortgage business are helping others achieve the dream of homeownership. That's noble work. That is awesome. That serves people. That's what I want to do. I realized that again, I hope I live longer than my dad did, but the reality is that I want to figure out a way to make a difference here and now.

Was there anything as we got onto this that you were hoping I'd ask you that I didn't?

There were some things, some stories from college, that I was hoping you would.

Wil, if you can imagine, it goes so fast. I got 100 more questions for you. You and I both know that less is sometimes more. We dove into the deep end here pretty quickly. Your thoughts on being thankful and grateful. What that mindset is like, you looking up. What am I doing to look up? What am I doing to care for my inside? These are some of the insights that I'm just walking away with.

I love that you're uncovering stories of people that make a difference. It makes me keep asking, where are we making a difference? Where can we change the narrative? I love that. That was really great. All the way down to I love the idea of the legacy. Our legacies are our relationships, but if I understood you correctly, understand who your master is and learn, how to love people and then seek wisdom.

Not to mention just a very direct place to go do that in the book of Proverbs. Thank you. That's probably enough. My hope is that people reading this will step back and do what you do and reflect, listen, and maybe take some notes. What we learn and some of the insights we get to have as a result of people like you are incredible. Little do people know, this is probably just for me, but I suspect lots of people are going to hear this and be thankful for you and what you've brought.

Thanks. Again, thanks for all that you're doing on this front. Your work really matters and is as important. You've made a difference, as I've mentioned, not only in my friendship with you through the years but in my work life. I'm grateful and grateful that you put this show together because it has been an encouragement to me over the last couple of years. Thanks for all you and Jason are doing.

You’re great. I have no doubt that I got to have you on again, much like the eulogy, there's so much more to draw out. I'd love to ask you about politically where you think we're going. Even though you said this or that, you have some really incredible insights there. What you've seen and a lot more about entrepreneurialism. You've just done so many great things. I'd love to ask you more questions. For now, we'll leave people hopefully to their own insights because it doesn't matter what my insights are. It doesn't matter what yours are. It matters what ours create in others. As a reader, what are your insights? Wil, thank you so much again.

Thanks, Steve.

Thanks for being part of it. See you next time here on the show.



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