S4:E65🎙️LIVE with Nick Rackley (Multi Audio Tracks)

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Welcome back to the Leadership and Success Podcast with Coach Beezid. I'm excited for today's episode because we're featuring a remarkable leader like me whose story spans the battlefield, the boardroom, and the tech startup world. Our guest is Nick Rackley, a U.S. Army Ranger, Bronze Star and Purple Heart recipient, and veteran of two combat deployments to Afghanistan. During his 8 years of service, Nick led soldiers in some of the most challenging environments commanded millions of dollars in assets, and embodied the Army principle that the commander is responsible for everything the unit does or fails to do. After transitioning from the military, Nick earned his MBA at Yale, his MS in electrical engineering at the University of Washington, and became a senior corporate strategy manager at T-Mobile, where he helped lead initiatives that impacted over 4,000 employees and reallocated more than $3 billion in resources. But Nick didn't stop there. Today, he's the co-founder of Vibe Otter, an AI-powered platform that lets small business owners create professional websites just by sending a text. His mission? To break down the barriers of entrepreneurship so anyone with a dream can launch and grow a business. Nick is also deeply committed to veterans advocacy as chapter commander of the Military Order of the Purple Heart, ensuring the stories and wisdom of older generations of warriors are preserved and passed down. In our conversation today, we'll explore what it means to lead with radical ownership, how combat lessons translate to tech and entrepreneurship, and why AI is unlocking new opportunities for small business owners everywhere. So grab your notebook because this is going to be a powerful session. Please join me in welcoming Nick Rackley to the Leadership and Success Podcast.

All right everyone, thanks so much for being here with me. This is Coach Bizzy. Sorry we are running a little bit late, we had some issues with technology, but it looks like LinkedIn is up and running now. I can see myself on the LinkedIn monitor. So thanks again for being with us today. I'm going to do what we normally do really quickly in less than a minute. We are going to be grateful, right? So let's take care of our moment of gratitude and For those who's been watching me for a while, you know I do this because in the military, about 21, 22 veterans commit suicide every single day in America. So, I believe when you are grateful, you can be suicidal at the same time. And I think being— having a spirit of gratitude is going to help you improve your mental health. So, I feel like we need this more than ever before. So, if you would please put yourself in your happy place, Take a deep breath if you need to, and think about one thing that you are grateful for today. What are you grateful for? And if you would please type it in the comment and share it with the community. Today I am grateful because I get to speak to inspirational leaders like Rick Wakely. I will be talking to in just a moment. It really is a blessing to talk with other people who inspire you and help you kind of get on with your own purpose as well. So that's what I am grateful for today. Please let me know what you guys are grateful for. So I've already introduced him in the teaser, but again, for those who missed it, Nick Wakely, He's a US Army Ranger, Purple Heart recipient, Yale MBA, tech strategist, and co-founder of Vibe Auto, where he's making it possible for small business owners to build professional websites just by texting to an AI agent. So from leading soldier in combat to leading entrepreneur in tech, Nick embodies resilient leadership, radical accountability, and innovation at the edge. With no further ado, let's bring on to the stage Nick Brackley. How are you doing today, Nick?

I'm good. How's everyone out there doing? Well, yeah, I'm doing great, Bob, and thanks for having me.

Absolutely. So to get started, is there one thing that you are grateful for today?

Yeah, I mean, I think the thing I'm grateful for is the same every day. It's my family, my two kids and my wife. That's, uh, I'm always thinking that. But yeah, I just thought you're like a statement about how like gratitude makes it hard to be suicidal. That really resonated with me. I think there's a lot of depth there.

Yes, exactly. And actually there is another veteran I'm a friend with. He actually does something where he asks people for 21 days to be grateful for one thing. It's like a challenge he has every year. I usually do mine around Thanksgiving time. And then so you're grateful for something today and then you challenge somebody else on your network to do the same thing. So hopefully your entire network will be grateful for the next 21, 22 days. I think it's quite powerful. So what is something about you that most people may not know about?

Just in general? I'm actually a character in a bestselling children's book series named—

Wow.

Yeah, it is based off of me, the character. It's called the Penderwicks. It was the best-selling book behind Harry Potter back during Harry Potter's heyday.

Really?

Yeah. And whenever I deployed, my aunt actually— my aunt's the author and she actually had the character join the military, which actually upset some people.

Are you kidding me? Who is your aunt?

Jeannie Birdsall.

Really? Yeah. Wow. What a small world. That is exciting. Okay. I didn't know about that. That is good to know. Can you tell us about your leadership journey?

Yeah, so I started— I grew up in central Pennsylvania, you know, playing football and doing pretty normal stuff. I joined ROTC at Penn State mainly to pay for college. I didn't really have some deep patriotic motivation at the time. I did ROTC. I kind of developed patriotic motivation, I think, through doing stuff in the Army. And then, yeah, I graduated. I was put in a pretty unique scenario where I deployed— I deployed to Afghanistan as a replacement for someone who got injured 10 months after I graduated.. So like in less than a year, I was in actual combat as a fire support officer, you know, in charge of a team of forward observers and going out with the infantry and supporting an infantry company. You know, I went on 2 violent deployments. That one, a little clip of it was shown. That was my command— my commander's RTO's GoPro, which we didn't even know he had on at the time. But that— I did a second deployment as a platoon leader on a fire base. Both deployments were near Pakistan. You know, I come home, I went to Ranger School, and then I stayed in through Battery Command. Around that time, I got married and decided to get out of the military, basically for my family. I just didn't think that it would be the best job for a family. I got out. Transitioning, I found very hard, so I can definitely talk about transitioning. Initially, like, I was telemarketing mortgages, and then I lucked out and ended up getting into the Yale MBA program and I think MBAs are an excellent way to transition if you can get into one. I did that, became corporate strategy at T-Mobile afterwards, which essentially ranges from like working on multi-billion M&A to advising the C-suite. By the end, I kind of became, you could say, like the CTO's kind of personal consultant on implementing his vision for what 5G would actually be and how to monetize 5G. I ended up quitting my job almost exactly a year ago, really without any idea for a startup. I always knew since I left the Army I wanted to do a startup, but I didn't. I never really got good ideas and I kind of wanted to do a forcing function on myself to just get it together. I felt like I was getting to an age where if I didn't act soon, I probably would never really pursue my dreams. So it's been up and down throughout the past year until I founded Vibotter. Vibotter is getting a lot of traction and it definitely feels like the, the original quitting was probably validated. Yeah.

Wow, what a story! Thank you so much for sharing, and thank you for your service. Uh, it's really amazing. I think America is one of the few countries where you do not have to serve in the military at all. For example, in France, if you are 18 years old, you are forced to join the military for a couple of years before you pursue your education. But anyway, really appreciate that. So going from Army Ranger with the, um, Purple Heart and, uh, becoming a startup founder with an MBA, can you share kind of, uh, the full line of your journey? What has stayed constant in your leadership approach through all of these transitions?

Yeah, I mean, um, like you were saying, like the radical ownership thing, like, you know, it's in like the Army FM on leadership, but the commander is responsible for everything the unit does and fails to do. But it really is true across organizations. I mean, in the military, everyone kind of knows that and does that. I mean, even like a team leader totally internalized and does that. I found it to be a lot more relevant in the civilian world. I feel like that's a much more foreign concept in the civilian world where, yeah, people just kind of go, okay, something wrong is going on. That's someone else's problem.

Yes.

Yeah.

Wow. So how did Ranger School and your deployment shape your definition of resilience and not quitting?

Yeah, so I've been thinking a lot about this. Like, um, when I was saying like the ups and downs of this past year, because, you know, I quit with about a year of runway and I have two little kids, so it is pretty intimidating running out of money and like potentially losing your house. Uh, so I kind of in a way almost have come to think of this past year as like my like entrepreneurship Ranger School. And yes, I recycled it quite a bit, but like, I just see a lot of parallels between how I got to where I am now, where it's starting to go successful, and just psychologically how I remember in Ranger School of like, you don't know if it's going to work out, you don't know if you're going to pass, you might be doing all of this for absolutely nothing and you still meet failure. And just being able to push through that and be like, well, no, I'm just going to continue. And if I fail in the end, whatever, at least I tried my hardest. I think there's a lot to be said for that in Ranger School, in a startup, and really in any meaningful endeavor in life, you know.

Yes. Yeah.

And talking about that, I think, uh, Will Jacko also wrote a book, Extreme Ownership. I think in the civilian world, people don't really get it. So, uh, and no, you've said yourself, right, the commander is responsible for everything the unit does or fails to do. When I was a commanding officer, definitely when the unit did great things, I would share the credit with everyone. And then when they did something that nobody was proud of, then I would take all of the blame, right, as the CEO. So, uh, How does this apply, this, uh, principle of radical ownership, when leading a startup team?

Yeah, so I mean, I think for start— I think most startup founders actually get this. I think it'd be very difficult to run a startup if you haven't internalized that. I, I see it as manifesting in the civilian world. Um, it's a lot more relevant, I think, in the corporate setting. That's where I've seen a lack of it. And I actually— I thought of a really good example because I know there's a lot of cybersecurity people on this podcast. The best example I can actually think of, I actually saw in like the cybersecurity domain at T-Mobile. Essentially like T-Mobile, in the wireless industry, if you're the weakest or the softest target for cybersecurity, you're gonna get hacked all the time. Like they only mess with the weakest target. And T-Mobile was the weakest target for several years. Everyone knew it was a big problem and they brought on some guy named Jeff Simon as like the chief cybersecurity officer. And he just operated completely different than any other civilian I'd seen. And I thought he demonstrated this very well. And tangibly, one thing they did is they started doing micro red teaming. They were sending out phishing emails to employees. And if you clicked on it, it wasn't like you get fired, but it just was like, hey, you clicked on a phishing email. You shouldn't do that. And it became a kind of thing amongst the employees, like, oh, did you click on it or did you report it? It was really, really effective. And to me, it was a great example of actual radical ownership because I think the typical security officer, when they took charge of that company in that position, would've been like, "Oh, we can't possibly stop everyone from clicking phishing emails," which is true, you probably can't. But if you actually in your head say, "No, we're gonna try," you'll probably come a lot closer to the goal. And yeah, I actually looked him up before this. He was promoted to the CIO of T-Mobile now. So he did an incredible job, and I think it was just from having that attitude. He was responsible for cybersecurity, period, dot, dot.

Yes.

Wow, that is really wonderful to hear. What about imposter syndrome? I have quite a few aspiring junior officers who watch my podcast. One day they would like to become a senior officer or a CEO, and also security engineers or analysts who one day would love to have a leadership role in Silicon Valley. Have you dealt with the imposter syndrome throughout your career, and what, what advice would you give them?

Yeah, I mean, I think imposter syndrome for me seems to come from times where I've like kind of like skipped something. So like getting in the Yale, you feel like you're like skipping something, or like doing corporate strategy right out of the military, like you feel like you're kind of like skipping learning something about business. I think that's usually when I feel like it. And I mean, in those situations, and then at the end of the day, the way I've dealt with it, I think the only way you really can deal with it is to really just do your best, you know, do your best to be very open to learning as quickly as possible. Because there's always this simultaneous thing where on one hand you know that you're not fully qualified for what you're doing, but on the other hand, like, the people that picked you probably picked you for a reason, so they know that you're in the ballpark. Um, but then on my startup journey, I'll say that is like probably the biggest benefit of like doing it right, like quitting my job and struggling through everything. Like, I don't feel imposter syndrome at all. Like, I know my startup inside and out. I've coded everything, I've done all the sales to customers. Like, so when you, when you don't skip steps, I think is when you, you don't have imposter syndrome at all.

Wow, that is, that is good to know. And talking about business and entrepreneurship, uh, Vibe Auto, pretty unique, right? You just, uh, send a, a text and then here you have a website. What inspired that idea?

Yeah, so, uh, throughout the past year, like I said, I tried a bunch of things that didn't work. And, you know, pretty much every time you launch anything new, you need to make a website. So I've been using AI to make a website the whole time, every time. And I noticed around in April, um, I, I use Claude Code. That's my big thing, my big tool. And in April, I noticed when the new Claude Code models come out, I, I was making websites and I wasn't actually typing any code by hand anymore. They were zero-shotting websites. So at that point, fast forward, and I know you're going to ask me about my framework, but I laid out a framework of 20 business ideas, and that's why I originally put it on my framework as something to explore. I was like, well, if I can zero-shot it, other people can too. That seems useful. But on the flip side, I was like, surely people are doing this already. So I wasn't actually that jazzed on this idea at all before I did it.

Wow, that is pretty amazing. So as a small business owner, no, usually feel overwhelmed by technology. How do you think AI is changing the entry point of entrepreneurship?

Yeah, so I mean, obviously, like, if I build a website builder, like, I do think, like, almost all businesses need websites. A lot of small businesses, like mom-and-pop shops, don't have them or they have bad ones and they don't really understand how much business they're probably losing from not being on Google. So lowering the cost, making it easier to get a website is obviously an easy way to help help out as a small business. But yeah, just, I think in general, just the ability to do more with less employees is going to continue to manifest as like a bigger and bigger deal for a small business that always is going to have a severe resource constraint.

Wow. And, uh, you've spoken about, you know, two core jobs at any startup, which is, you know, building and selling. How can founders avoid the trap of doing everything but those two.

Yeah, I think it's like a nefarious trap because everyone knows you're supposed to be doing those two, but like a lot of times you get sucked into these holes that are like faster payoff or you think you're seeing faster results kind of thing. Like, I mean, the big hole I kind of fell into this hole over the past two weeks because I've been trying to post on LinkedIn a lot more and like you can spend a lot of time tracking your progress on LinkedIn that has absolutely nothing to do with your business. So that's actually my goal for this week is to start timeboxing myself a lot more with posts to LinkedIn. Yeah, I think you just have to be conscious, like, in the end of the day, like, if you're not actively talking to customers or serving customers or actively building something that, like, a customer has asked for, you kind of ask— got to ask yourself, what are you doing? Because those are the only things that are going to actually move you forward.

Wow. So how did your time at Yale and T-Mobile corporate strategy team complement, uh, what you've learned in the U.S. Army?

Yeah, it was a great compliment. 'Cause in the Army, I mean, the obvious one is like, when you transition outta the Army, you don't know anything about business. So like, any of those jobs and an MBA will at least help you teach the language. Like, the language gap is huge for veterans. Like, when I first showed up at my MBA, I realized there were a bunch of people from other countries who could communicate with like, my classmates a lot easier than I could, just because they spoke the language of business. Even if like, they didn't speak the same actual language that well. So it's like, it's just huge learning the language and it's good for that. Like corporate strategy or any job like that will teach you the ins and outs of finance. I think like learning finance and Excel modeling, it's really useful beyond Excel. Like if you're trying to do entrepreneurship, like just being able to like think of a business model and like really quickly figure out if it's like ballpark gonna work or not, it's a really big deal for ideating. And then, yeah. It's, yeah, I think that's, I think that's probably the biggest ways that it is helpful.

Now, uh, you are deeply involved with the Military Order of the Purple Heart. I believe you lead your local organization there in Washington. Why do you think it's important for young Iraqi and Afghanistan vets to connect with Vietnam vets while we still can?

This is a really recent realization and initiative of mine, but I'm really trying to encourage Iraq and Afghanistan vets to to join a VSO to connect with Vietnam vets. I've come to realize a lot of these Vietnam vets, like, they don't really have that much more time where they're gonna be able to share with you, like, maybe like 10 years. A lot of them, you know, they have been affected by Agent Orange and it's just crushing them. I like, I joined the chapter here actually when I quit my job about a year ago, just because I mostly wanted to just connect with people 'cause I knew I would be coding a lot in the beginning. Um, and yeah, just hearing the Vietnam vets' experiences, hearing— it impressed on me how they kind of talked similarly about how like they had that same relationship with World War II and Korea vets. They'll always talk about what they used to say in our meetings, and it made me realize like, if I'm the only one here and no one else is joining, like, who else is going to carry on like the Vietnam vet and probably by extension the World War II and Korean vet knowledge? So I think it is really important to get out. I mean Active duty people probably aren't going to go to a lot of VSO stuff. I don't think I would if I was active duty, but I really encourage any veterans that are Iraq and Afghanistan to get out and join a VSO and learn from the Vietnam vets before it's too late.

Yeah, I think that is, that is so important. I know I'm originally from Africa. They say when an old person dies in Africa, it's like an entire library that has been consumed by fire. There's so much wisdom we can get from our elders, those who have gone before us. So, uh, how can transitioning service members then translate their leadership experience into startup or tech success?

Thank you.

Yeah, I mean, I think there's like two broad classes of service member. There's like one that like is going to be— they actually had like a relevant job experience. Like, I mean, you're probably a great example of this, class. Like, you pretty directly could translate a lot of your military job experience to civilian sector. Uh, for those people, I would, I'd recommend probably just being about as straight up as possible and communicating your skills. Somebody out there is probably going to get it. Also, just getting in touch with a veteran who can go and read it. Like, there was a guy that applied to the T-Mobile Corporate Strategy one time who, like, he was like one of the people in the Navy, literally, he was the equivalent of like central FP&A for the Navy. And I was just like, whoa, this guy is like hyper qualified to be doing this at a Fortune 500 company. So if you get in front of a veteran, like, they'll immediately see it. The second class of people, the one I fall into, I think is the more like, you know, combat arms operational people who like, you know, I was artillery and the only relevant civilian job for artillery is like shooting cannons at mountains to stop avalanches. You know, people, a lot of people say when you're getting out that like, oh, you were commander, you have all this management experience. In my experience, like, civilians basically don't really care. No matter how you explain it to them, they just have this block in their head that that doesn't count. And I really believe a lot of civilians think most guys in the Army were just walking around the woods with a gun. So how do you deal with that? I mean, I think you have to calibrate your expectations. Like, you're probably not going to start out commensurate with what your experience says it should, which isn't fair, and you just kind of got to get over it. Like, there was a battalion commander at T-Mobile that had gone through SAMS, that was starting out at the same level of me. I thought that was enormously unfair, and it probably was, but that's just the way it is if people don't really want to be open-minded to experiences out of other fields.

Yeah, yeah, that, that, uh, makes sense. Although some people do get lucky, especially if you get one star, uh, usually you are on board of advisors or something. But yes, I definitely see that. So, uh, where do you see AI entrepreneurship aiding in the next 5 years?

Um, I think, I think the next kind of brand of AI-native companies, you could say, I think are going to look very, very different than other companies. It's going to be very low employee, especially I think in the software engineering realm, uh, just because the AIs are— I, I value cloud code at at least like 10 engineers.

Like, wow.

But both in like, it's, um, people really focus on the productivity, but I think what gets underfocused on is the expansion of knowledge because it knows everything. Like, I probably would have at least had to hire consultants or stuff for certain things that I obviously don't know. But like, with AI, every engineer kind of is an expert in everything if they actually know how to use it correctly. So that's huge. And the result is I think you'll have way smaller companies, um, which probably will be a lot more profitable and etc., etc. You have a lot less communication overhead. Since you don't have to have as much management since there's not as many employees. The other interesting thing I think you'll see in AI startups is use of internal tools. So like, we, whenever we have a problem or I'm doing something boring, I always ask like, can I automate this in some way with AI? And because we're already programming and it, you know, it takes me like 3 hours to maybe set up an internal sales prospecting tool to automate something we were doing manually that you wouldn't be able to do without AI. So it's like, I think a lot of these AI-native startups are going to be bizarrely profitable, and eventually people will realize it's because they're applying a bunch of internal tools that really any company could have done, but probably corporations just struggle to overcome inertia that a brand new company didn't.

Now, having said that, put yourself back like when you were in college, right? We have these young people, they aspire to be leaders in tech. Or the military, and now you are telling them that AI is going to take away all of the entry-level jobs. So what would you advise an aspiring tech leader who's not an entrepreneur to kind of do to kind of get their first job in tech like you did?

I think doing projects. So I mean, like, I, I think the more precise thing to say is it's going to take the entry-level jobs that exist that doesn't mean it's gonna prevent entry-level jobs in the future. They'll just look a lot different. So like, I think entry-level software engineering jobs are gonna look a lot like software management. I mean, that's how I interact with AI now. I basically consider myself a software engineering manager, and I think that's gonna be the entry-level job. And the way you develop those skills isn't by like coding a bunch in class or like listening when your teachers tell you don't cheat with AI. It is by using AI to like make tons and tons of different projects, challenge yourself with like the trade-offs of an architecture. And I think if you can develop those skills, I think people would love you as an entry-level engineer, or you also may have the skills to build a startup yourself.

I like that because I really do believe people who do use AI are going to be the one who are going to get promoted and probably take away the opportunities from those who, for whatever reason, don't want to use it. All right, so we are about to switch over to the second half of the show, uh, Is there a question I should have asked you for this first half that I have not asked yet? Anything you'd like to share?

Um, not a question. I will also— the interesting comment is you showed that website I made on Viber of my personal website. That actually was like— that wasn't even intended to be a public-facing site. I'm surprised you found it.

That was—

wow, that was okay. Yeah, actually, let me show the people what you are talking about. I believe you're talking about this one, right?

Yeah, I actually made this just testing the tool. Um, this was a zero shot. I just put my resume in and said, hey, can you make me a personal website if I was recruiting to be a product manager?

That's pretty awesome.

I was really surprised when you brought it up. I was like, whoa.

Yeah, it's because you can see the bug at the bottom of it.

That was before.

Yeah, Google, uh, is, uh, it's indexed in Google. That's how I, I was able to—

yeah, I might need to index on some of my testing sites because I come up with pretty ridiculous testing So it's like I have a site, dog trying to sell bones.

No, it, it really looks professional. Def— definitely this is another reason why, uh, you should have more customers. Definitely do great, great work. It's pretty amazing. So, uh, first, uh, category for the second half of the show, uh, what is the greatest, uh, lesson you have learned so far?

Yeah, I mean, I think, you know, in the military I've known a lot of people who got killed in combat and I think it just taught me the lesson that like every human life really is valuable. You know, we're all truly unique. I've never met anyone in my life that is exactly like somebody else in every single way. Even people that look the same and have the same kind of background usually move differently or have different mannerisms. I think that's a reflection that we all really are unique and that we should be valued. And to be honest with you, I don't really think our world does value life appropriately. You know, we start wars all the time and just throw it away, but Even in the corporate world too, sometimes I think like people get overly focused on just keeping their jobs and not focused on like really accomplishing what they want, which is, if you do that your whole life, that's another way of wasting a life.

Hmm.

So what, what do you think is the secret of your success in the military and in tech?

Um, I think, yeah, like a responsibility and ownership mindset. I always keep coming back to that. I really have always genuinely believed I'm responsible for my own life, not my parents, not anybody else. And, you know, I act accordingly. I always think through the consequences of my actions. And yeah, like, not quitting goes such a long way, I think, in anything. If you're trying to do anything meaningfully difficult, like, there's gonna be a lot of times you want to quit. And if you do, then you're not going to accomplish what you want. It's just that simple.

True. A couple of days ago, I wrote an article about impossible dreams, and I mentioned time I saw this on, right? He tried 10,000 times to create the light bulb. And the way he was thinking about it is, I found 10,000 ways it doesn't work, eventually I will find the way that does. And he did. And, you know, I guess to say the rest is history. But I think that I will never quit and I will find a way. Yeah, that definitely plays a lot with it. So what do you think is the greatest leadership advice you have ever received?

Um, I think, I think take care of your soldiers. And, you know, obviously that could apply in the civilian world, take care of your employees. But it really is like, if you take care of the people that you're in charge of and you genuinely care about them, like, everything will just go a lot better for you. And it's just the right thing to do beyond that. So, you know, in the military, they'll go and die for you. In the civilian world, I think if you take care of your people right, they'll be a lot more creative and just come up with ideas and be willing to say things that they wouldn't if you were you know, trashing on them and you were marginalizing them.

Yes, I know in the Navy we said, uh, mission first, people always. I think the Army says that too. But, uh, yeah, really, in my opinion, the military is a leadership organization. We just happen to have a bunch of hardware, even at the lowest rank, though. I think that's really what makes the difference between us and some of the other militaries around the world, because some of those other armies, if you get rid of all of the generals, everybody's going to be completely lost. But In the US, you can get rid of all of the generals. The chiefs know exactly what to do, and they're going to take care of the enlisted and the officer and so forth. So even when I was a seaman recruit, right, E-1, 20 years ago, even at that point where you are at the lowest rank possible, still the Navy is really teaching you about leadership. You are a leader because, no, in terms of war especially, it could be a matter of life or death. But, uh, It's definitely something I think in the corporate world, in the industry, people need to learn more, I think. But anyway, yeah, absolutely. So, uh, as a leader, what are you learning now? I know, uh, leaders are always learners. What are you learning these days?

Yeah, so I mean, I switched almost from like day to day and week to week, uh, because I, I really got into— I go on long runs and I listen to audiobooks, so I consume really large amounts of books or podcasts. Um, right now I'm trying to learn about search engine optimization because I'm beginning to realize it's a huge— A, I need it for my own website, but B, it's a huge benefit for like these mom-and-pop shops that could be like losing thousands of like visits from Google just because they're not optimized right. So eventually I want to build my AI to just do it automatically for people. Yes, but I'm, I'm having a bear of a time finding experts in the, in the subject. There's a lot of like kind of hand-wavy people. I always look for people that like can demonstrate that they actually did what they said they did, like tactically.

Yes.

And unfortunately, in this subject, it's one that if you, if you're actually very public about beating the system, then Google is going to change their system and probably, you know, de-index you. So I'm having trouble finding the experts there.

Yeah, I guess it's the algorithm is always changing, which by the way, I think LinkedIn has significantly change their algorithm this year because a lot of things that used to work before just don't work any longer. But anyway, so what is the greatest investment you have made in yourself?

Yeah, I mean, I think quitting my job last year without an idea. I think that was, I mean, it was a massive investment, you know?

Yes.

It's like a year's worth of savings. And yeah, I even saw it as like, even if I ultimately fail in this, I will have learned so much, I will be well positioned to go in the future. So it's like, yeah, I just— it's the classic like risky investment.

That is really a great way to look at things because I think for most people they have great ideas but they are afraid or ashamed or whatever it might be. They, they never act on it. I think Les Brown, one of my mentors, said the richest place in any city is the cemetery, because that's where all of the dreams and hopes have gone to die. And many people, they die with a lot of regrets. So I'd rather try something and even fail than not try at all, because then you wonder what could have been.

Yeah, yeah, I never want to wonder.

Wow. So by doing so, kind of like, no, the idea I've learned in Silicon Valley with the way they do, uh, HR tech and software development where they try and cycle so many times because almost every time in the startup world in Silicon Valley, the very first iteration of their product is usually pretty crappy. It's not very, very good. But the thing is they never give up and they get a whole bunch of feedback and then they make it better, better, better. And before you know it, it becomes a really excellent product solving problems that even the founder didn't know it could solve. That's really a mindset I really love here in Silicon Valley. But in order for them to be so successful though, they've had to go through a lot of failure and sometimes people don't think about it. So, and I think I want— we were in the green room earlier today, I talked to you about this coin which I love to see. One side says failure, the other side says success. So two sides of the same exact coin. How has failure shaped your life so far?

Yeah, I mean, I think failure shaped my, my life a lot. Um, I, I consider my biggest failure was a combat failure where I lost a soldier, and I had a lot of, like, you know, anyone's gonna have a lot of survivor guilt from that. Um, and yeah, I mean, I think just, you know, kind of overcoming that, learning your lessons about how, you know, you were an inexperienced lieutenant, um, and that Yeah, you know, you basically, you did your best in coming over it. Uh, it's really helped my life in the long run though, of just the sense of it's made me value people a lot more. I think that's why some of my responses to some of these other questions are always so people-focused. It's like, that's why. It's like, I genuinely do have like just a deep value for all the people I encounter and everyone that I work with. And yeah, it's also like a very— it is like a very big humbling thing that is always going to be with me in a good way. Like, I think it's good to stay humble no matter how successful you are. I mean, I am almost getting to the point where I worry more about success than failure now because I, I like who I am as a person. I don't want anything to ever change that.

Well, I am, I am really, uh, sorry to hear that. I know it's probably going to stay with you for the rest of your life. And once again, thank you for your service. I think most people in the corporate world, they really don't understand what it is like to serve in combat in the military these days. But I think America is only great now because of people like you, people who answer the call, say, "Yes, here I am, send me." Now it's kind of interesting in my life, especially after 9/11, I've been in the military for over 20 years and I've been mobilized to a combat zone of Afghanistan, Iraq, Djibouti, and a few other places 3 or 4 times now, but each time beyond my control, my orders were canceled. I think it's definitely an opportunity I would have loved, but if I did go, I really wouldn't want to feel— to see someone so close to me, you know, lose their life while I was you know, on orders. I think— well, I did see a sailor lose their life when I was deployed on the USS Essex. I was a lieutenant general grade there, O2, and, uh, pretty much committed suicide. He jumped off the platform. When we got him, he was completely purple. That wasn't because of combat or anything, but I think he had received a letter from his wife who decided to mess around with his best friend or something. But anyway, he felt like he didn't have any hope and, and, uh, he just, uh, lost, lost his life. It really affected the entire crew. But, but yeah, that was very, very, very sad to see. I would never be able to get that image out of my mind. But yeah, it's, it's, uh, life, life in the military can be really, really, really tough, whether you are in combat or not.

Yeah, uh, we were talking about that. Civilians aren't aware of how many people actually die in non-combat, not even suicide, but in just in training accidents and stuff. I think a lot of civilians would be shocked to hear the rates of like getting crushed between tanks.

Yeah, but, uh, thank God that these people under my charge throughout my entire career, as far as I know, everybody returned safe to their families. Because as a commanding officer, you know, Sometimes I've had maybe, what, 2 dozen people, I think, in my entire military career I've had to send sometimes in harm's way. No, again, knock on wood, all of them came back to us. But it would be really, really terrible to tell the spouse of one of your sailors, I am sorry, but, uh, you know, he gave his life for his country. Again, we know that's what we literally signed for, but when it actually happens, it is something else. Yeah, but anyway, again, thank you so much for all of the veterans out there, people who are serving their country in uniform. We definitely owe you a huge debt of gratitude. So, uh, can you share what is the greatest fears that you were able to overcome?

Uh, greatest fear, you said? Yeah, I mean, I think my greatest fear is always, uh, change from time to time. I mean, I think a guiding North Star in life has always been I usually try to do something if I'm afraid of it. I found that to be a pretty good indicator of like what I probably need to do to grow as a person. So, you know, when I first was out of college and going to combat, I think my greatest fear was just screwing up something in combat, you know, as a brand new second lieutenant in charge of like all the air power and artillery power. Um, you know, I got over that one just by— I always try to just simplify things when whenever I'm like getting in a really bad situation. Like I was like, in the end of the day as FSO, I only really screw up if I blow up a friendly American or if I blow up an Afghani civilian. As long as I know where all those people are and I don't call for fire on them, like it might not be great, but at least I'm not completely screwing it up. So that was like one. I think getting outta the military was actually a pretty scary time. I mean, and I think that's actually pretty well known. I don't, I don't know really anyone who was like, yeah, I just crushed transit.

Sure. Yeah. And it's also amazing how much responsibility the military puts sometimes in the end of junior officers like you were, or even some, you know, junior enlisted, because I've known some enlisted like first class petty officer who were in charge of quite a lot. And yeah, it's something that normally in the civilian world, you know, you don't see something comparable to that. Sometimes you are in charge of equipment that are worth like millions or even billions. At times, and, uh, you kind of help make those decisions for national security. It's pretty amazing. Uh, so who are some of the people that you know that we should follow? Who are some of your thought leaders?

Um, yeah, so Paul Graham, uh, I've found just everything associated with Y Combinator to be really enormously helpful in the past year. They have like a startup school curriculum that I think that's the best content I've seen for entrepreneurship, and it's completely free. Um, I really like reading Paul Graham's essays. I just feel like he thinks kind of like I do, and it's probably because, like, uh, he was like an artist before he became a software engineer and then started building company in like the '90s. So I, I also, I like to paint. Um, uh, painting has like both helped me therapeutically, but I think it actually has really helped me professionally.

Um, nice. Yeah, well, that is wonderful. When people ask me something about me, most people might not know, I've been playing the piano since I was 7 years old, and that has really served me very, very well. At first I did it just because my dad asked me to, but later on I really got into it. It helps you relax and maybe even be more creative at times, because initially I was reading those scores, like classical music, you played exactly the way it is written. But later on I really loved getting into jazz and blues where you kind of have some boundaries, but you can be more expressive and kind of make up your own, I guess, use your own creative juices or even create a sound that may not have existed before. And I like kind of mixing different sound and instrument and kind of do my own thing. But anyway, that is really, really cool. And what about books? Which books would you recommend to my audience?

Well, yeah, I mean, uh, because we were talking about the benefits of painting and creativity, like, one of the books I recommend to pretty much everyone, especially military veterans, is Drawing on the Right Side of the Brain. Uh, that's actually how I learned to draw and paint. Um, and it's a book that basically just gives you really basic exercises like drawing a picture upside down. Oh, that's Joseph Campbell. Yeah, but drawing a picture upside down, the whole idea is that like we have atrophied right brains because we live live in this left-brain society. And if you can actually actively develop your right-brain kind of skills, uh, through drawing— I think the book does an incredible job. I was drawing like stick figures when I started. I really— off— I was awful at art. And now I can like, ah, full paintings that people actually want in their house. Like, I'm not selling them, but like, people actually— people find them desirable, which blows my mind. The book did it. But the reason why I mention it for everyone is I say it actually helps professionally a lot because I don't know, like, in consulting you're always dealing with these, like, ambiguous problems that are, like, too hard to just draw a decision tree and figure out. And I feel like the right side of the brain thinking, it helps you when you're dealing with problems that there's just so much uncertainty, there's no way you can actually draw a plan to get to where you want to go. Right brain thinking is, like, just start doing something, and then if it doesn't work, go over here, and then here, and then here. And drawing and painting really develop it. I, I find it much easier to deal with, like, you ambiguous stuff in business now that I draw and paint. So that's why I really recommend it to everybody. It's not a quick fix, it takes like 4 to 6 months, but yeah, it's powerful.

Wow, wonderful. Any other book you recommend?

Yeah, I mean, for leadership in general, um, South by Ernest Shackleton. I just call it up because like I didn't know anything about this story until about 6 months ago. It's the most outrageous story of leadership and adventure. Are you familiar with Ernest Shackleton?

No, I, I went to write this this one yet.

So basically, these guys, they decided they wanted to try to be the first guys to go across the South Pole by foot in 1900. Um, they drive their— they drive their wooden ship, you know, down at the beginning— or not 1900, it was right at the beginning of World War I. So World War I breaks out while they're down in Antarctica. They get stuck in ice. Their ship breaks in ice, so it strands them on the ice, and they just go around like floating on ice for like 4 months during the Antarctic winter. It breaks apart. They go in little rowboats boats and go to this ice island. And then eventually the leader actually crosses the most dangerous ocean in the world, the Drake Passage, which pretty consistently has like 30-foot tidal waves going across it in a little rowboat. I mean, wow. And so he actually managed to bring every single one of his guys home in probably one of the, like, probably one of the worst survival situations that I think humans have been in. So yeah, it's just a phenomenal book on leadership. In particular, him, he, he— that's like the graduate level of leadership where I think he He talks about at points where he actually lies to his guys sometimes because he doesn't really think that it would be good if they knew the truth. Like one time they row, they row in the wrong direction when they've been starving and like sleep deprived and everything for like 30 miles. And then he, he was like, they'd probably mutiny if I told them the truth. It dances in these hard situations around like, you know, there is an appropriate time to like not be completely honest with your followers, which I think is like something that I wouldn't have resonated with me unless I had heard that coming from that guy in that situation.

That is quite interesting. I know in my military training, the only thing I would lie about would be classified information, but yeah, definitely need to keep the morale of the troop. But yeah, I don't know, I guess it depends. But in my own experience so far, it seems like people tend to follow you more when you are vulnerable and kind of put yourself at their mercies and tell them like it is. Of course, not everybody is going to be with you. I know from my last command for sure, I probably had about 98% of people with me all the time, but there was that 1 or 2% that just didn't like me for whatever reason, which it does happen. But yeah, leadership is not easy. There's always some something to, uh, to learn and how you deal with, uh, people, right? What, what about this book here, The War of Art?

This one was really helpful to me, I think, actually getting— I don't know, getting off my butt and actually doing entrepreneurship, like getting up every day in the morning. I, I call it this one too because I think this is particularly accessible to a veteran audience. You know, it's by Steven Pressfield, the guy who wrote The Legend of Bagger Vance, Gates of The Fire, a bunch of books that are already— yeah, he was a Marine, so like his brand of like how to do creative art stuff I think is way more accessible to like the average grunt.

Wow.

Than like anyone else, because he was a grunt, you know, and it basically is just be— wake up and be disciplined every day about what you're gonna do.

Yeah, because when you first said it, I thought you meant The Art of War, which is by Sun Tzu. I think everybody in the military has read that one. I'm like, wow, that's So that's pretty cool. And I believe Drawing on the Right Side of the Brain is the one you mentioned earlier. What about this one?

This one's pretty recent for me. It's like kind of percolated a lot through business culture, and I think people encounter it without realizing where it comes from, but it's called The Hero with a Thousand Faces. And it's essentially— the basic thesis is that like every human story, our own lives are stories. And like every story actually follows the same basic kind of structure, even our like personal stories, how we view our own lives. And that it just describes that structure as like the hero's journey. So that's why it's A Hero with a Thousand Faces. Wow. You're the hero of your story. I'm the hero of my story. You know, every great story is the hero of their own story. But I think it's useful to read. It's like, yeah, it's definitely like the PhD of literature. I think the book is even hard to understand sometimes. The first time I I read it anyway because I wasn't a PhD in literature. He goes, he just brings examples from myths all over the world. But I think it's useful directly because, you know, a lot of times people are like, oh, humans love to communicate in stories, but no one tells you if you're not a good storyteller how to tell stories. I think that book gives you an in-depth understanding of story structure and narrative structure. And also it's just actually helped me. It actually has helped me viewing my own journey as a story in the structure.

Yes.

When you, when you get to your big points of failure, it's like, it's a certain key point in the story where failure occurs to help you grow and get past your current boundaries. And that's just universal stories.

I guess controlling the narrative. If you're going to be a business leader, a presenter, you need to be able to tell captivating stories. And that's powerful. And then, uh, one more that you mentioned was, uh, Made in America.

Yeah, so I, I mean, I, I absolutely love reading uh, biographies, and in particular like autobiographies, because I really like hearing from the person themselves. I mean, of course, depending on the autobiography, you have to take it with a grain of salt. Like, if you listen to his autobiography, he has a lot more political motives than like probably Sam Walton did. But I think it's just great. You learn a lot. Like, from that book, like, the one thing I always learned, he always had this like impulse that like the reason why Walmart's costs are so low was because he had this thing in his head that if like his suppliers charged him any more money than they should, it would— he knew it was going to get passed on to the customer and hurt his customer. He was like, he was not totally focused on profit maximization. He was focused on maximizing the customer experience, which to him was like everyday low prices. And when you listen to it in his own words, you absolutely see like that's why Walmart is the way it is, and that's why Walmart helps a lot of people by giving them really affordable goods.

Incredible. Yeah, there is so much, um, we can learn from biographies for sure. Okay, uh, Anything you want to mention about movies that you recommend?

I don't know if I watch deep movies personally.

Good, good. I know I used to not watch movies at all, but I think I was a lieutenant junior grade when one of the best skippers I had started to teach me how to look for leadership lessons in movies. That kind of changed the way I looked at entertainment. Okay, another question for you. If you could choose 3 people to have dinner with, who would you choose and why? It could be dead or alive or even fictional figures.

Yeah, so I mean, you actually talked about one of them, Edison. I think Edison is a pretty incredible individual in the realm of invention. I mean, once I read his biography, I just— so much of our modern world actually comes from him. Beyond the light bulb that we don't talk about, i.e., like the fact you can hear me right now, he was the guy that invented being able to play back There's just so much there and his methods. I think Leonardo da Vinci, uh, he's just a pretty unique character through all of history as far as I can tell in the realm of like invention and creativity. And then yeah, I think, I think the third one actually would be Jensen Huang. Um, I think Jensen Huang is just— what he's doing with NVIDIA is pretty incredible and he's pretty clearly going to become, you know, the Ford Edison-like figure of our time, I think.

Wow, that is wonderful. So, uh, we are coming toward the end. Let me ask you, okay, if you had one and only one day to live, what would you have liked for your final contribution to be?

Yeah, I mean, if only I wanted to live, I would definitely just hang out with my family. I wouldn't really be worrying about a contribution at that point. You know, like I said in the beginning, I really— that's what I'm grateful for all the time. I would want to give my kids just one more day with Dad.

Absolutely. And when you wake up in the morning, what is one problem you would like to solve?

I think it changes every day. I mean, I always try to— kind of from that War of Art book, I try to wake up at the same time every day, which is 5:20, so I can actually be in my seat and doing something by 5:30. And I always just want to solve whatever the actual biggest problem I have that day is. It's funny too, because when I got out of the military, I said I would never get up early. I was completely serious about it. And now I get up at 5:30 every day because that's when my mental energy is the best. I feel like from like 5:30 to like 9-ish, I can just crush the hardest problems.

Wow. And that started when you joined the Army, right?

No, I hated getting up early in the Army. Army, like with a passion. And when I was getting out, I said I'm never going to get up like before 9 as a civilian.

Wow.

And then I just kind of fallen into the rhythm where I'm like, yeah, it's good for discipline to get up early. It really is. And that's why it is.

There are several books written about it. One is The 5 AM Club by one of my mentors, Robin Sharma, and somebody else, Al, um, somebody, The Morning Miracle. Anyway, Oprah talks about it too. But yeah, for me it happened exactly 20 years ago when I went to boot camp as an enlisted RTC Great Lakes in Chicago, Illinois. I've been waking up at 5:30 AM every single morning since. It doesn't matter which time zone, doesn't matter where I am in the US or out of the country, 5:30 AM, I just wake up. And yeah, it's been pretty cool. Okay. Let me ask, ask you this. Uh, we are coming toward the end of the podcast. You've been so generous with your time. Uh, what could my audience do to add value back to you? How could we make a difference?

Yeah, I mean, I really appreciate people trying out Vibotter. You know, we're still pretty early stage startup, so just even getting the word out about us is really helpful. And then, yeah, I mean, for any veterans out there, Iraq and Afghanistan veterans, getting involved in your VSO I really do think it's important, and, um, it's something that's— the clock is ticking. I think learning from these Vietnam veterans, maybe like 10 more years realistically.

Yes, I believe you are, you are right. I remember the very first time I went to a VSO with Vietnam vets. I was an ensign back then, Task Force Alabama. They were so glad to see me because everybody was very, very old. They're like, hey, this is the next generation of, of leaders. And So excited. Yeah, I think you, you also would make a difference in their life just for being in there in their presence and asking about their leadership story and their journey. So, uh, what is the most rewarding aspect of your life experience so far?

Uh, the most rewarding, I think, my whole life experience? Yeah, my family. I mean, I'm always going to come back to that. That's the most important thing to me. I'm definitely not entrepreneur who's like, oh, I love my business more than my family. It also helps that my co-founder is my wife, and that, you know, that's kind of somewhat deliberate. Like, I do want to have— you know, I can't, I can't remember who I was listening to, but somebody was like, if you work with your family, then you get to work with the people you love. Yeah, that like resonated with me.

No, that is so good, especially for those who are in the military. I know some sometimes, you know, military life is is not conducive to family life. I don't know, you know, how many events I have missed throughout my career. And some, some sailors I have talked to, they're like, no, the Navy issues you everything, right? They're like, maybe it's time for the Navy to issue me a new spouse. But I don't know. But, uh, yeah, it's, it's, it's kind of sad though. When you accomplish everything you felt like accomplishing, the rank and all of that, but then you retire, you go home and you are all by yourself. Nobody to share it with. Your kids don't know you. They probably hate you because you've never been around. So that's really no way to live. So family first, for sure. So is there a question I should have asked you that I haven't asked before we end the podcast?

No, I mean, I think that was pretty thorough. I love your questions. Awesome. They're unique.

In that case, this is the most important question for the podcast. This is really the reason why I I do this every single day, talking to aspiring leaders, especially in the military and in tech, which both of us have that experience. What advice would you give to your 17-year-old self standing at the edge of this incredible career you've had? What would you say to them?

Yeah, I would say like focus, focus a lot more like on finding love and loving the people around you instead of like proving, you know, how badass you are or something like that. I think it's super relevant now too because I do, I do see this like kind of conception of masculinity going towards like this like UFC rah rah rah kind of how big are your muscles thing. And like, that's not, that's not manliness to me. Like, yes, I think that I actually make the argument like the ultimate act of manliness would be like something that gets you the Medal of Honor, like giving your life for someone you love. And like, yes. That right there has the word love in it, you know. It doesn't have anything to do with how big your muscles are. You could be the littlest guy in the world if you did that, and that would be the ultimate act of manliness in my mind. So yeah, that's what I would tell myself. I think I wasn't like that. I probably was more bought into the other stuff before, you know. I learned the hard way that that's just not the way it is.

Wow, that is very, very profound. So 3 adjectives that describe you as a child, really quick.

As a child, I'd say, uh, happy, Curious, fun-loving.

As an adult?

As an adult, I would say intense, curious, and fun-loving.

Okay, very good. 2 out of 3 stayed. Very good. Okay, and now this is the very, very end. What is one word that represents our shared experience together on this podcast today?

Sorry, what was that?

One word that comes to mind that represents our shared experience. Today on this podcast?

I think insightful. Yeah. I appreciate some of the insights you've shared about gratitude and everything.

Yeah, I think mine would be grateful. I really, really am. I feel like I'm the luckiest person on Earth to get to speak with people like you. Okay, this is the end of our podcast. It's been 1 hour and 1 minute, and sorry we were a little bit late. And thank you so much for giving me more time. Sometimes this technology doesn't work the way it is supposed to. Thanks again for being with us today, Nick. Really, really appreciate it.

Thanks for having me.

Thank you.

All right, guys, you've had it. That was Captain Nick Rackley. It was such a wonderful time discussing his leadership journey and what he's doing in tech today. So we are going to end again. I didn't see any question on YouTube or LinkedIn, and I triple checked to make sure I didn't miss any. But even if you have a question, during the replay, go ahead and type it in the comment, and we're gonna make sure to get back to you. Thanks again for watching. Please like and go ahead and repost in your feed or tag someone you think might benefit from this discussion. And until next time, this is Coach Bizzy. I'm actually gonna be back here tomorrow where I'm going to have another great interview. So hopefully you're gonna be with me live on LinkedIn and on YouTube. And thanks again for being here. Bye. Bye everybody. This is Coach BZ. Thanks for watching. Until next time, don't forget to like, comment, and share.

Thank you for listening to the Leadership and Success Podcast with your host, Coach BZ. If you like what you heard, please subscribe to our channels and come back for more wisdom nuggets. Nuggets on how you may develop into a better leader and achieve greater levels of success. Leadership is the most critical skill. The world will always need leaders to lead others, deploy the next disruptive technology, or execute a business strategy. You may as well decide on counting yourself among the 21st century leaders. See you right here next time on the Leadership and Success Podcast with Coach BZ.