Ep. 37 – AutoLoop COO, Alex Eckelberry

Alex Eckelberry serves as COO of AutoLoop which develops disruptive SaaS solutions in the automotive software space. He has been with several companies as an investor, board member, and a turnaround engineer before joining AutoLoop. He talks about his working relationship with the CEO and how they have complemented their skills for the betterment of the company. Alex highlights how essential it is to work based on trust. He shares how he’s straddled the line between being an entrepreneur and being an operator, but what matters, in the end, is how you get your job done.


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AutoLoop COO, Alex Eckelberry

Alex Eckelberry is a technology CEO but serves as the COO of Autoloop, a fast-growing disrupter in the automotive software space. Before Autoloop, he spent the last few years as an investor, board member and turnaround engineer including being a board member of BlueStripe Software, acquired by Microsoft, a board member of StopBadware, a board member of KnowBe4, a board member of MalwareBytes and chairman of the board of Runaware. Autoloops develops disruptive SaaS solutions that are transforming automotive tech. Their 450-plus professionals are dedicated to providing best in class solutions for major OEMs such as Hyundai, GM, Toyota, Fiat Chrysler, Kia and Subaru, as well as leading edge automotive dealership and large groups. At Autoloop, Alex leads the operational, sales, marketing, OEM and call center activities. He’s agreed to share with us some of his expertise and insights of being a second in command and a leader in the space. Alex, thanks for joining us on the Second In Command podcast.

Thank you so much for having me on. It’s a great honor and a pleasure.

I’m looking forward to this. Why don’t you give us maybe a little bit of background, a quick little helicopter tour of what Autoloop does in the SaaS space specifically? Also, give us a rundown of some of your background that got you to the stage that you’re running as a second in command. I want to find out some of the differences between the COO role and the CEO role that you’re used to playing as well.

Autoloop makes software that helps dealers engage their existing customers and acquire new customers. It’s a marketing automation platform that also has the ability to manage the service sides of the dealership’s business. We started out of automated service marketing, then going into managing the service lane of the dealership. We’ve since moved into having a dealership CRM, a trading value platform, which allows your dealers to value trades and a bunch of other things. We’re the last of the large independent software companies in automotive. Personally, everyone on our scale has been acquired. That’s it. We’re the only ones left. We have now close to 500 employees. We’re at scale with several of the large OEMs. We have about 2,400 dealerships. The business is doing great. It continues to grow.

In terms of how I got here, I’ve been a technology nerd all my life. I started talking over the Commodore 64. I’m 52 years old now. I always wanted to be in technology. I always got involved at a relatively young age, whether it was programming or messing around or building our own computers, that kind of thing. I landed my first professional job at Borland International in 1987. There was a time in Silicon Valley where you could get a free beer anywhere you want saying you worked at Borland. Nobody knows more than you do. Now, it’s not a well-known company.

Back then, it was a big deal.

It was an amazing company to start my career. I thank God that I started there because I got this incredible way of dealing with customers and way of building products that Borland was very much ahead of the curve on how to make products, how to price them and how to distribute them. They were way ahead. Things you take for granted now, for example, a money back guarantee on a piece of software, you think it’s normal. Back in the ‘80s, there were no money back guarantees in software. You bought your software, let’s say you paid for it. It doesn’t matter if it’s $500 or $1,000. Borland introduced a money back guarantee. Borland simplified the process of the end-user license agreement. They simplified a lot of things. They also brought software pricing down to a reasonable realm where it used to be $500, $600 a piece of software became $50.

I learned a lot. My career went off from there. I went to a startup with a bunch of friends back in the late ‘80s. It didn’t do that well. We sold that. We were young. We were stupid. We did it. We did sell out. It was a company called Aegis, which people remember some of the old Mac programs. We were the first in the area of video titling and video software way ahead of our time. After that, I went to work at Quarterdeck, another company which has been forgotten but very well-known back in the ‘90s. Quarterdeck now more as Webex, which was one of our spinouts and also a good part of Semantics products were Quarterdeck products. We were broken up. We went public. I went and did my own startup in the late ‘90s, which I sold to Kroll Ontrack a couple of years later. I went and became a professional investor for several years. I worked at Bulldog Capital. We’ve got ultimately acquired by Monitor, which became part Deloitte.

I went off for eight years in my own software company, Sunbelt Software, which I had joined when the company was pretty small for about $10 million in revenue. I joined them in about $10 million to under $15 million in revenue. I had a very nice exit. I had sold it to a company called GFI. I ran the security business for GFI. GFI was a company that made a lot of IT tools. I left GFI. I’m wondering to do my own thing for a while. I did a lot of work in consulting and turnarounds. It was a lot of fun. I did a lot of travel, which I love to do. A couple of years ago, one of my closest friends, Steve Anderson, who’s the founder of Autoloops said, “Would you come on as my COO?” I joined him. It’s been a fantastic ride.

One of the interesting things for me is that I had never had any strength or expertise in selling very complex software applications that required a lot of integration points. I didn’t have that as my background. I frankly shied away from that throughout my career because I didn’t have the knowledge. Autoloop has definitely handled any issues I had there. It’s a complicated difficult software install. We have hundreds of integration points. This is a platform with seven million lines of code of which half are related to integration, whether it’s Credit Bureau or integrating with the dealer’s backend ERP systems.

It’s as complicated as Salesforce or more so?

It’s very complicated stuff.

How long have you been with Autoloop now then?

Two and a half years.

What was the size when you came in? How many employees were there when you joined?

I don’t honestly remember the number, maybe 400-ish or something like that. We’ve since grown about 20% as a business, a little bit more than that.

What was the genesis of Autoloop? Did it start like an in-house software package for some dealer or was it developed as a SaaS platform to then market to dealers separately?

It was started as an automated telephonic system for dealers, an automated phone system that would call out, “Your car is ready for its service appointment.” That moved into marketing automation that moved into the full platform.

Huge envy that you went from a Commodore 64 to an Apple II. I was never allowed to buy the Apple II. I’m totally jealous that you got one.

I’m not going to oversell myself here. My work with C64 and II was always borrowing other people’s computers.

SIC 37 | AutoLoop

AutoLoop: Borland was very, very much ahead of the curve on how to, how to make products and how to price them and how to distribute them.


Mine was using it at school as well back in the day. You mentioned a couple of things that I think were interesting. It’s how fast some of these companies scaled and then either died or acquired. To have so much experience around that, has that changed your perspective of how to build the company or the companies that we build, do you have any worry that we were building something that is going to be out of business in five years or ten years?

Cameron, that is so weird you say that. I look at so many of the companies I’ve been involved with have been at this 500, 800 employee range. We were well-over a thousand. There’s this range and you hit up against these limits and you do hit these, I wouldn’t say that their ceilings, but there’s this bump, and this is rough, nothing science based. Maybe it’s up to the first $5 million is one bump. It’s maybe up to $20 million is the next bump. It’s $50 million is the next bump. The $75-million or $100-million bump, and then this $200-million bump. I’ve gone through those stages up to about $250 million and that’s the most I’ve gone. I’ve never gotten a $1 billion company. I’ve never done that. Larry Ellison had a fascinating interview. It’s on YouTube. It’s a fascinating interview about when they got to $1 billion, they found out they didn’t have the right people. Honestly, I’m not sure I’d be the right person. I know I’m good at this $50 million to $250 million, $300 million range. I’m comfortable with it. I can sit very comfortably in a crowd of 500 to 1,000 employees. Can I get above that? That’s a whole different game. That’s fascinating. This is what’s so interesting.

It’s a different game for us as executives. It’s also a very different game for the mid-level team. I was talking to the founder of Infusionsoft. He said that “A mid-level team can only go through two consecutive doubles in terms of their revenue growth.” I read in Ben Horowitz’s The Hard Thing about Hard Things saying that, “The mid-level team can only ever go through one triple in revenue before they put themselves for the most part out of a job.” It’s interesting to think through that. I’m also curious about the companies themselves. Do you build a company in the tech space now? Do we build them to sell or are people still trying to build these legacy companies that are going to be around for a lifetime?

Maybe I’m a little bit jaded. I had a great conversation with a very close friend of mine. He built a nice $25 million, $30 million a year business. I talked to him a couple of years ago. I said, “How’s it going?” He goes, “It’s going great. I’ve got my daughter in here. I’ve got my son. My wife is working here. It’s a family atmosphere.” I said, “That’s great.” Three months ago, I get a note on my Google search. He’s already sold his company. It’s cashed out. I’m going, “Come on.” Does anybody ever do that? I wish we did that. I’ve got four kids. I would love to have a place for my kids. My oldest son’s name is Cameron. My son, Cameron, works for Malwarebytes. He’s a developer.

It sounds like you’re at least in an industry in servicing that dealer market or the auto market that you can continue to evolve. If you’re into those channels, you can continue to develop for them. Is part of the strategy then of Autoloop to do acquisitions or to continue building? Where are you focusing?

All of the above. Another interesting thing for me, which is new, not necessarily new, but a little different is Autoloop is not a venture back company. It doesn’t have triple investors although I’ve had those kinds of operations before. In this case, our founders are very much focused on keeping the control of the company and Steve Anderson. We do things that I’ve never done in the past. We use debt for example as a tool to make acquisitions. We’ve done several acquisitions versus raising an equity round, which is typically what I’m more familiar with. I’m not familiar with debt. I have plenty of debt, but literally using debt as your primary method of working capital, primary benefits, expansion capital, versus equity is something that’s also been new to me. We used a combination of the two. Honestly, it’s nice. There are no board meetings.

I think more companies should focus on building real businesses with real revenue, real teams and real business plans versus more equity rounds and build their bus. I think more companies would be able to be built and survive if they ran it like a real business like you guys are. Tell me what did Steve see in you to bring you into the company? What did you see in him or in the company that you wanted to go into a COO role versus the entrepreneurial CEO role?

First of all, I do want to hit back on that point you had earlier about building companies to last and all that because that’s a very fruitful territory there. Steve and I have been best friends for years. We’re literally very close. We both oddly end up working in different areas together. One of my first startups was in the Boulder, Colorado area. He was working in Baltimore. Steve and I were great friends. It’s a perfect marriage. It’s a weird word to use. It’s a partnership. He’s the dynamic entrepreneurial guy and I’m the guy who’s basically making sure that the organization is running in the right direction. It’s very complimentary. I wouldn’t have done it otherwise.

I’m used to being the guy in charge. I’m used to being the CEO. It’s not like I’m stuck with it. I like working. If I’m working for somebody, I respect him. I have no problem taking second in command roles. It’s about moving the ball forward and creating a great game. My goal is to take Autoloop to $300 million, $400 million company, and scale it. I talked about that glass roof that I’ve had personally in my career. I haven’t hit more the $250 million, $300 million in size. It’s great to be able to get above that and move to 500 minds. That’s why I joined him.

I’m curious then what he saw. I didn’t see what you saw in him like best friends and you got that huge trust and cool to be able to work with your buddy. I did it with Brian when we built 1-800-GOT-JUNK? He’d been my best man at my wedding before I even joined the company back in October 2000.

You’ve built 1-800-GOT-JUNK?

I was the COO there. I took them from fourteen employees to 3,100 employees in six years.

I’ve listened to this great interview with Guy Raz. I was like, “What a great business.” That was your partner. He’s so cool.

He’s great. We’re still very good friends to this day. In fact, Guy Raz and I spent about an hour together talking at the TED Conference. That was a good podcast. That was a fun company and a fun ride. I get why you and Steve are doing it because that’s what Brian and I got to do is we got to hang out and build something. It was cool. Only when it got to about a $100 million is when it started to get big for me. In fact, when I left, it took him a year to replace me. They brought in the former president of Starbucks US. She came in and said, “What a cute little company.” I was going, “It’s big.” She’s like, “What a cute little business. Let’s grow this.”

What Brian saw in me was that I had a lot of the franchising background. We’d been in a forum in the Entrepreneur’s Organization together for years prior. He saw that I could build companies. He also knew I had franchising expertise, which he wanted. I’m curious what Steve saw in you because typically two entrepreneurs, I forget what the term Brian use. We were like nitrogen oxide. We blew up in a beautiful way together until it got too big for two entrepreneurs to be running it. I’m curious what Steve saw in you that allowed him to feel like you could be the operational side of a more complex business already like coming in with 400 employees. Are you more of an operator than an entrepreneur then or are you able to straddle that line?

I straddle the line. I’m unusual. I’ve been entrepreneurial. I’ve run companies. The other aspect though is that I got my teething pains out of the way in a larger enterprise. I’m very comfortable and conversant with how to work in larger organizations. That is often considered a potential liability because large company guys will have a hard time running a small company. I’m talking about Borland maybe when I got there was $85 million, $90 million. Back in 1987, that’s maybe $150 million these days. Companies of that size up to $100 million, $200 million or $300 million, those aren’t huge companies. They’re fairly small, especially at the executive level. They’re pretty collegial as you well know. I had that process background. I think trust comes a lot into it. I trust a lot. If you’re an entrepreneur, you’re bringing in somebody that you’re going to hand a bunch of keys to, you’re going to want somebody that you feel it’s not going to screw you. There’s a big push, a big leap for an entrepreneur as you were.

SIC 37 | AutoLoop

AutoLoop: Taking a secondary command role is about moving the ball forward and creating a great game.


You and Steve had that then for sure?


How did you get on the same page with his vision? What part of the business does he still operate and what part do you operate? Walk us through the org chart.

It’s a fluid org chart. I have responsibility for the field organization, for example, which is a pretty big organization. I have responsibility for the customer success part of the organization. The fluidity is that we’re working with a large account, say an OEM, we’ll both work on it together. How else are the OEM team in there as well? It was a big part of our business. In our own way of working with each other, it’s pretty collegiate way passing things back and forth. If you look at what Steve was good at, Steve is a bit of a math genius. He’s fantastic. Even though I’ve got a lot of background in finance operations, he likes to keep that himself.

He likes to keep the finance area himself. He’s very good at it. He’s very smart with money. Frankly in some ways, he’s a little smarter than I am at some things on the money side, I’m more process oriented. The terms of that in the genius of being able to see where the numbers are very rapidly and see a path to profitability that I might not see is very good at that. Whereas I balance some very well known on the process side. It works pretty well. I think people at Autoloop know it’s just Alex and Steve. Two people that I think are hopefully are pretty easy to work with. I’m throwing up right now going, “Alex was so full of himself or with Steve.” I don’t think that’s the case.

Is Alex the iconic leader? In some companies, you have the Howard Shultz or the Ray Kroc or the Brian Scudamore. I’ve always felt that the COO’s job is to make the CEO iconic. Our job is to make them look good. Do you guys play around that area at all?

It is Steve’s company and I respect that. He compensates me very well. I’m very happy. My job is not to take his job or steal his thunder. He is at the helm of the company and the success of a company relies on the number two getting full support to the number one. Anytime it goes anything different than that, you’ve got a disaster in your hands. I was the CEO of a comparably sized company and I had a COO working for me. That COO I always running 100% support from, 100% is the same. It goes both ways. The thing is that these kinds of couplings work well when both parties are comfortable enough to give the power back and forth. He throws me the power. I throw the power back. What is power? It’s not some weird game. Power as he put it to get things done. When you’re giving your CEO the ability to get things done and to give him more freedom to get more things done, then you’re giving value. When I’m happy is when I see him relaxed, confident, walking through the hallways and saying hi to people when I’m nervous is up when I see him stressed because I know I haven’t done my job.

He’s got to have your back as well. You mentioned the CEO has to be there to support the COO as well. It’s got to go both ways. How do you and Steve stay in sync? How do you grow your people, grow your leadership team? How are you growing them?

We’re dancing on the laziest possible way, which is we have lunch every day together. That’s an easy way to keep in touch, keep in sync with your CEO just go to lunch. You’re bound to have to talk about some part of the business. We have lunch almost every day. A few of us will go to lunch because you’re busy. You’re running around. You’re running in the morning and grabbing a cup of coffee, going to your meeting. Sit for 30 minutes and talking about how the business is doing, where things are, do a quick huddle and we go back to work. We don’t have long lunches. I’m saying we get together at least once a day.

That’s in terms of keeping the constant sync of the business and there’s a lot to think about. There’s a lot of things constantly going on. I tried to keep him focused on the strategic versus the tactical. My job I feel is more tactical. His job was the goal setter. In terms of how we develop our employees, we do that in terms of developing the senior management team. We expect a lot out of people and we expect them to step up to the plate. If they stepped up to the plate, we will reciprocate with whatever growth and development they need to get to the next level. I’m not looking to take somebody who’s not showing that initiative to want to grow. I’m talking to the senior executives. We’ve done this where we’ll identify employees that are identified in the organization as eating growth. We’ll identify those people. We’ll work on growing them because we believe that in many cases, we think more of themselves than they thought. It’s very common as you know.

I came out of the company. My genesis back when you were at Borland, I was building a company called CollegePro Painters. I don’t know if you’ve ever seen College Pro, but it ended up being the largest house painting company in the world. We were taking university students 800 a year and training them to be franchisees. They would go out and hire 8,000 students. Between May 1st and August 31st, we’d paint $60 million in houses. Everyone would quit and go back to school. We became a real training machine. It was probably our strength is recruiting and leadership development. Do you have any core areas that you think are important for leaders are important for COO? What soft skills, leadership skills do you think are the most important for you?

First of all, we all know that the term COO is vague. Sometimes it includes a finance function, sometimes it doesn’t. Sometimes it includes sales, sometimes it doesn’t. The name of your podcast being Second in Command. That’s perfect because it’s the deputy. The definition of a deputy is somebody who has all the authority of the person above them. They’re deputized to carry out those activities. I think a critical thing is that you’ve got somebody who can take that. Steve can go out of town, go to the country and people can check sign of it easily. That’s the core idea.

The leadership skills, is there anything that you’re good at that you might even take for granted? You mentioned Steve with his math skills. What are your Yoda superpowers that you go, “Yes but that’s not that big?” Everyone else is like, “You’re good.”

People would say on the math skills side, they’d say I’m also pretty weapons grade. I’m not as good as him. He’s good. First of all, there are the tools of the trade. The tools of the trade in our trade are Microsoft Office, being weapons-grade up at the Office Suite. Excel, for example, is the tool of a COO. That’s your tool and your weapon. I have been blessed very early on with having had a very strong background in spreadsheets. I know it sounds crazy. Before that too, I was part of the Quattro launch team in Borland. I’m telling you that has been one of the most valuable things I’ve had in my career is having a strong background in the Office tools whether it’s back in the old days, Word Perfect and Lotus 123 or modern day’s Microsoft Word, Excel.

I remember the very first computer that I brought to work because they didn’t provide them to us was in 1989. I brought in an IBM 8086. I had Lotus 123 and Word on it. The CEO that I was reporting to is like, “Why do you need a computer? Scott has one next door.” I’m like, “I’m going to do spreadsheets.” He’s like, “For what?” I’m like, “I want to show all our franchisees.” I remember he’s like, “That’s stupid. You’ll never need it.” It was the dot matrix printer days. I remember back when you wanted to print, what we now take for granted in landscape mode, you had to export from Lotus 123 and import it into Sideways 123 to then print it out on a dot matrix printer. I think like that was a fairly early stage. I’m going to say, “I agree.” Excel is one of the weapons of the COO for sure.

Throughout my career, I’ve had this unfair advantage because I have been very good in those areas. I’m so glad you said that because that’s exactly how I would’ve approached it. I walk into my PC with a spreadsheet, word processor and of course, later PowerPoint. It’s one of the great tools. You got your toolbox. You’re good at your toolbox. I see a COO who was stumbling around in PowerPoint or Word Perfect. You can’t build a pivot table. I’m going, “You are losing out a whole lot.” You don’t have to be building Visual Basic Script, but you do need those core things, Pivot Table Slicers, that stuff because that’s how you pull your data together and analyze and start working with it. That’s very volatile.

Other skills, people skills, ability to communicate, ability to message correctly. I’m one of the primary communicators with the company. I have a thing called Loop Love. We first came into the company. It was a lot of confusion. We call Autoloop employees Loopsters. I created this thing called Loop Love, which is we share success stories and happy stories and shout outs to employees. All that communication is managed by me. Steve sets a direction and the vision. Steve says, “We’re going to go out. We’re going to go climb Mount Everest.” We go, “Yes.” Someone’s got to pull the Sherpas together. Someone’s got to pull a mule team together. That’s me. He’s Edmund Hillary and I’m Tenzing Norgay.

Tenzing Norgay’s grandson took me to Everest base camp by helicopter a few years ago. It was cool. It was the two of us who went up to Everest base camp and had breakfast overlooking the base camp. It was his grandson. It was neat.

There it is right there. It’s Tenzing Norgay.

Who or how often do you ever have to tell Steve that Everest is the wrong mountain? Do you ever say, “We’ve got to go do Annapurna instead?” Or that’s the wrong strategy? I think that the COO also has to be if anyone is going to say, “The emperor has no clothes,” it has to be us. If anyone says there’s something wrong, so how do you have the confidence to do that? How do you do that? How do you tell them they are wrong or you believe they’re wrong or you believe there’s a better way?

SIC 37 | AutoLoop

AutoLoop: Keep in touch and keep in sync with your CEO. Talk about how the business is doing and where things are.


They’re strong entrepreneurs. Having working with strong entrepreneurs, they can roll over you. There are several times we had a meeting earlier where I was, “Steve, I think we should do this instead of discussing something in the sales activities. Keep it simple.” He’ll push back or not. Ultimately, this is a company. He’s writing my paycheck. He has the right. I definitely won’t go buy something. I feel ethically and morally, it’s my duty to say something. I’m not a normally a contradictory person, pretty easy person to get along with. I definitely will say something. It’s essential that you have a COO, somebody who worked with you can trust.

Who can say that? We need someone to tell us when we’re blind or that they think we’re blind.

Have you seen Bohemian Rhapsody? There was this one line. It was one line where Freddy Mercury goes off and does a solo career. It’s not that great. He comes back to the band that goes, “Nobody ever said no to me.” It’s exactly what I wanted. If you listen to the solo stuff, it’s pretty awful.

I remember the era too.

This was Queen. When he was in Queen, it was incredible. That’s a dynamic is that these guys are going, “No, I don’t like that idea but let’s try something different.”

You’ve heard the parable of the emperor that has no clothes. One thing I’ve learned, especially with the entrepreneurial CEO, is when you’re going to contradict them or say that you think they’re wrong is to do it privately, one-on-one. You don’t do it in front of them because thankfully they’re very narcissistic often or they’re very strong-willed and they’re going to drive hard. They’re quick starts that if they feel like they’re being cornered, they’ll lash out or they’ll steam over you. When you do it one on one, they’ll hear it. They’ll listen. They trust that you’re doing it for the right reasons for their company.

That’s called common decency and good manners.

I like conflict. I like to have the team openly debating in a team environment. When it’s with the CEO, I sometimes want to take that aside. I want the team to challenge everybody on the team. With the CEO, I like to do it privately. I’m not sure how to stickhandle around that if it’s right.

It’s all based on context. You are in a group meeting. You’re discussing a bunch of things. He’s looking for ideas. You’re there to tell him something. When I’m talking about manners is I’m in a situation where I’m in a meeting, I disagree with them. I’ll play it by ear. There may be a situation where I’m going to want to go, “Let’s take off.” We’ll talk separately. It’s a stupid idea. You’ve got too much in front of the other people. I don’t want an atmosphere of conflict.

You mentioned something interesting around, some COO’s have finance and some have marketing. Harvard wrote an article called The Misunderstood Role Of The Chief Operating Officer. They uncovered seven distinct types of chief operating officers. It’s along that line that some are very inward facing, some are very outward facing, some are operational or engineering, some are processes, some are marketing and outward. It’s cool that we are very different. I think that key is that Yin and Yang relationship, that two-in-a-box or trusted second-in-command. We have to have these different skills. It also frees up the entrepreneur.

It complements the entrepreneur. You could define a COO as somebody who complements the entrepreneur with maybe the things the entrepreneurs aren’t good at or doesn’t want to do. For me, it’s having been in this on both sides. You had the same experience. You had been a COO yourself. That’s very helpful. I’m not looking to sit in his chair. I’m not looking for his job. I’ve been very fortunate to have met a lot of success in my life and financially that’s not my game. I am interested in what can we do to build this company to a great company. He trusts me for that. I get upset when I see him being dragged down in the business because I feel that I’ve failed him. It should be, “I got this. Don’t worry about it.” Sometimes it’s easier to ask for forgiveness than ask for permission. That plays a lot of the job of a COO. Your job is not to sit around and your COO, your CEO, your job is to get shit done. Frankly, it’s like, “What are those bodies doing at the side of that?” Just ignore those bodies.

That’s what I talk about in making the CEO iconic. Our job is to buffer them and pretend that for sure. I’ve got two questions. I want to touch base or talk about an area that you had struggled in the past as a leader and a final question after that. Is there an area that you had struggled as a leader that you’ve had to work hard at or get better at? Maybe a big mistake that you’ve made that you learned from?

I think I remember your screener asked me this question when she first got me. I think the one area that I feel I’ve continually had to improve on is a level of communication with the people that work for me and work around me. Sometimes I’ll move too fast. I’ll be moving out of the whole pack. I have to stop and realize, “These guys don’t know where we’re going.” That’s my responsibility. That’s the discipline of having meetings and process and pulling those things together because sometimes it’s easier to move fast and get out ahead of yourself. That’s probably the one area that I’ve wanted to spend the most amount of time focusing on is making sure that those areas are all pulled together. The other is making sure that goal setting on my own area is being done. I’m great at taking the CEO. It goes from running with them. Sometimes my guys go, “Are we supposed to do that? My bad. I didn’t do it.” Thank God I know that these things need to be worked on.

You don’t clarify it.

That’s my goal.

I want you to give us your parting leadership lesson. Something that you wish you’d known when you were 21, a big leadership skill or a leadership lesson that you wish you’d known when you were a lot younger.

It does work out in the end and doesn’t sweat all the small stuff. I know you’ve heard that before. I wish I’d gotten that. I spent so much of my career warring being worried.

That’s been mine as well. I didn’t get it until I was probably 50-ish that none of us are getting out of this alive. None of these matters. This is what we do to make money. Let’s have fun while we’re doing and not take yourself so seriously.

You nailed it. I would go on a trip and I would go to the city. I would run a hotel room, work on my laptop, get up early the next morning, do my meeting. Try to go to the airport as quickly as possible. I didn’t smell the roses. I didn’t look around. I didn’t say, “I’ll pay for an extra night at the hotel out on my own pocket and spend the weekend here.” See this beautiful city. Some of the most incredible places on the planet.

I’ve gotten a lot better over the years. It’s turning it off. I now finally don’t work on weekends ever. I don’t work after 5:00 PM now because I’m never going to get caught up. There’s always going to be another goal or a bigger business.

SIC 37 | AutoLoop

AutoLoop: A COO is somebody who complements the entrepreneur with the things the entrepreneurs aren’t good at or doesn’t want to do.


I’m deeply envious. I’m always working. I do at least take the time to smell the roses. If people understood the value of pleasure, it is a valuable commodity. When I realized that taking a nice walk in Vienna, or down a beautiful street or those kinds of things, those are the moments that you live back and remember and that you treasure it. They warm her thoughts. Take the time to enjoy yourself along the road because you get to be like me in your 50s and go, “I wasted a lot of time working my ass off.”

I’m going to leave us with that. I’m going to go for a walk. I’d go for a little walk in Vancouver and smell the flowers. Alex Eckelberry, thank you so much, the COO from Autoloop. I appreciate you sharing with us.

Thank you for being on the call. I appreciate it. Thank you.

That was great. Thank you.

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About Alex Eckelberry

SIC 37 | AutoLoop

A Silicon Valley veteran, Alex has been in the technology field for 30+ years. He’s worked at some of the world’s largest software companies and currently sits on the board for Malwarebytes, KnowBe4, and Runaware. Alex is also an avid writer and published author.



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