#129 Welcome to the Families of the Class of 2030

Your son or daughter just earned a Naval Academy appointment and you’re proud, rattled, and unsure what to expect all at the same time. I get it. When a family doesn’t have a military background, USNA can feel like a different planet with its own language, rules, and stakes and your brain naturally jumps to worst-case scenarios even while you’re celebrating a huge win.

I share my own path from a family with zero military ties, the early days when I wanted to leave because it was hard, and the long growth arc that changed everything. We talk about what a service academy education really aims to build: mission, purpose, team, belonging, and a whole-person education that forges resilience through difficulty. I also unpack a problem almost every Naval Academy parent runs into: communication. Midshipmen are overwhelmed and short on time, parents want to help, and it’s easy for both sides to feel stuck between hovering and disappearing.

To make that gap smaller, I point you to resources built specifically for Plebe Summer prep and I-Day preparation, including a Plebe Summer terminology guide and a Class of 2030 families newsletter where I’ll share guidance, interviews, and more private ways to ask questions. If you’re building your support squad for a future midshipman, subscribe, share this with another USNA family, and leave a review with the biggest question you want answered next.

To stay most up to date with Grant, Naval Academy updates, and real estate insights, follow him on LinkedIn

The mission of Academy Insider is to guide, serve, and support Midshipmen, future Midshipmen, and their families.

This podcast is independently produced and reflects the views and opinions of its creators. It is not officially affiliated with, endorsed by, or representative of the United States Naval Academy or its affiliates.

Grant Vermeer your host is the person who started it all.  He is the founder of Academy Insider and the host of The Academy Insider podcast. He was a recruited athlete which brought him to Annapolis where he was a four year member of the varsity basketball team. He was a cyber operations major and commissioned into the Cryptologic Warfare Community. He was stationed at Fort Meade and supported the Subsurface Direct Support mission.

He separated from the Navy in 2023 and now owns The Vermeer Group, a residential real estate company that matches service academy families with trusted real estate teams all across the country.  Text (650) 282-1964 with any real estate questions.

We are here to be your guide through the USNA experience.

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Transcript

Welcome And Who This Is For

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Welcome to the Academy Insider Podcast. If you are a family member of an incoming plebe in the Naval Academy class of 2030, then you are in the right place. Whether you're a mom, a dad, grandpa, grandpa, aunt, uncle, friend, sibling, whatever the case may be, this platform, this podcast will hopefully be your guide just to provide a little bit of context, perspective, and understanding to the Naval Academy journey. I hope you enjoy this episode, which is going to be a brief rundown and the congratulations about this exciting milestone in all of your lives. If you ever have any questions, reach out. Otherwise, I look forward to getting to know you. Thank you so much. Before we get started, I want to make a quick disclaimer to make sure everyone knows Academy Insider and myself, Grand Premier, are in no ways official representatives of the United States Naval Academy, the Navy, andor the Department of War. What I'm doing here again is just trying to provide a little bit of context, perspective, and understanding for the Naval Academy journey. But my use of the Naval Academy and conversation about them does not imply endorsement from the institution. If you ever have any questions directly for the Naval Academy, I encourage you to reach out to them directly and the Public Affairs Office. I appreciate it. Thank you so much. And I hope you have a great listen to the episode. I remember when I was getting ready to accept my letter of appointment to the Naval Academy because it was such a different path for me and my family. I have no family who was military. We had, again, nobody really in our world or lives who had a background in the military. And so I had no idea what I was getting myself into. I just knew two things. Um, one, which was that my dad was so proud. I specifically remember being 17 or 18 years old and just being able to sense the like palpable pride that my dad had that I had an opportunity to attend the Naval Academy. And my dad wasn't military, but he was police for a long time growing up. He was a police chief in my city, the hometown of Mountain View, California, uh in the San Francisco Bay Area for a long time. And so the sense of public service was there. We never really had a military background though. And um it was just fascinating because for me as a young person, all I could really remember was this dichotomy of feelings from my parents. My dad, I had this overwhelming sense of pride and he was so excited for me. And on the flip side, I had a mom who was very um open about the fact that she was nervous about what I was choosing to do, right? And again, for a lot of people who end up going to the service academies, um, that wasn't your only choice, right? Like you had a lot of potentially great college opportunities for you to go to. I specifically remember my mom being like, you could be going to MIT and you're gonna go to the Naval Academy. Like, what are you like, what are you doing? Right. And again, from her perspective, she couldn't uh comprehend because she didn't know. All she thought and all she could think of was that, you know, her son, her baby, was gonna be entering a profession of arms, a day an inherently dangerous um profession and career path and education and all the above. And so um, you know, there are gonna be a couple of things that come out of this that I hope to have a conversation with you. But the first piece is if you're a family who doesn't fully know what the Naval Academy is about or doesn't fully get it yet, and still potentially has nerves, I I totally get it, right? Like I totally empathize with that. My family was very similar. We didn't have a military background, we didn't fully understand it. And I don't know that the nerves, right, will necessarily go away. I think there will always be a worry for the well-being, you know, of your baby, of your child, of someone who you love dearly. And that's totally fair. Um but I hope this episode comes across in a way um where we get to talk through this because at the end of the day, you know, again, I think we have immediate emotional reactions. Uh always our brain goes to the worst case scenario of things, you know, going and we can understand that like this is an incredible thing and I'm excited about it, but you can also have nerves at the same time. And that's totally uh legitimate and totally fair. I want to get across in this podcast episode is just a reiteration to you as a parent that um, you know, despite the immediate reaction, I think what you're gonna discover is that your son or daughter is gonna choose a life that is gonna give them a sense of mission, a sense of purpose, a sense of team, a sense of belonging, um, things that you can only dream uh that your child would have, a real sense of life fulfillment, a real sense of purpose in everything that they do. And then on top of that, they're really gonna get an education of the whole person, right? I'm sure in today's day and age, you have conversations about college and all these, you know, aspects about what's actually happening on campus, what level of education they're actually getting, all these different things. And the one thing that I can guarantee you is that an education at the Naval Academy, an education at the Service Academy is going to be a whole person education. Your son or daughter is gonna grow. They're gonna develop, they are going to turn into the greatest version of themselves through trial by fire, through difficulty, through rough times, through calls where they're gonna be crying on the phone potentially. Um, but it's all worth it. And and I and I promise you that. I promise you that. Um, you know, one of the most difficult things that you may experience as a new parent as well is just a complete lack of understanding, right? A lot of parents don't even fully understand what their son or daughter is doing at normal college, uh, let alone at the Naval Academy. And that's where I come in, right? And I hope this platform Academy Insider serves as a resource in trying to fill in the gaps and understand the context and trying to provide perspective into the experience that your son or daughter may be going through. Right. I know you saw the disclaimer at the start of the video or the podcast. Um, I'm not an official representative of the Naval Academy. I'm not their public affairs office. I'm not advocating on necessarily behalf of the Naval Academy. Um, you know, my story is a little bit distinct. It's a little bit different. Um, I, again, we talked about the fact that I came from a family that had no military background. I didn't know much about the Naval Academy. There were mixed feelings. I showed up at the Naval Academy and uh I did not have a good time at the start. Like I was, I was ready to leave, I was ready to get out of there. I had no interest in staying at the Naval Academy because it was hard, right? And um it was just one of those things that uh, you know, I had a very polar experience to the negative. But as a result, towards the end of my time at the Naval Academy, I probably had one of the most polar positive experiences because I had such an immense growth arc as I started to understand why I was going through what I was going through. And as a result, I was sitting at the Jesuit Retreat Center in Los Altos, California. Uh, it's called El Retiro with my dad uh in the spring break of my senior year. And during spring break, we went up and sat on a bench at the top of the hill overlooking the Silicon Valley, and we were talking about my experience at the Naval Academy. And, you know, we were kind of laughing and joking a little bit about like, man, I can't believe I made it here. I can't believe we were sitting at this moment. Like I thought for sure I was gonna be gone. Like I didn't think it was gonna work out. And um, you know, we kind of reflected and laughed about some of those moments, laughed about the journey. Um, but then my dad asked me uh a really thought-provoking question. He he said, Um, when you look back at your time at the Naval Academy, what do you wish you would have done better? And, you know, I I thought back to it, and obviously at this point I had a really positive feeling about the Naval Academy. And um, you know, I sat and I thought with it for a little bit, and I told them, I responded, and I said, I wish I would have done a better job communicating to you guys about what I was going through. I felt like I had put my parents in a really tough spot, a really difficult position in how to support me and how to love me, because they wanted to be involved, but they didn't want to be overbearing. Every time they tried to ask me questions, I would get annoyed because I didn't have time to explain everything. But at the same time, they didn't want to be so hands-off that they thought they didn't care, that I thought they didn't care, right? And so trying to find that balance was really difficult. And I felt like I put them in a terrible spot of how to support me because like I needed the support. I wanted them around, but I didn't have the time to explain it. And I put them in a really kind of terrible situation where there were it was lose-lose. They didn't know how to behave or react, right? And so um, you know, with reflection, I was like, yeah, I'd like, I'm sorry. I I felt like this is a really difficult situation for parents to be in and try and understand how to support their machinment at the Naval Academy. And after I explained that, he looked at me. And um, you know, again, we were Jesuit educated. Uh, I went to Bellerman College Prep in Northern California. Obviously, we're sitting at the Jesuit Retreat Center, it's a very reflective um, you know, organization, but it's also about action, it's also about service. And my dad had kind of asked me, so the follow-up question to that was what are you gonna do to make it better for the next wave of midshipmen and their families? And that kind of like sat with me, right? That was that was a real challenge, right? It's okay, like, yes, this was an issue you had. You wish you would have done it better. How are you gonna make that better for people? How are you gonna help solve that problem? How are you going to provide and make a positive impact in the lives of a community that you really care about? And uh that was the origin of the idea of Academy Insider, right? I had gone from, you know, being a plebe who wanted to leave all the way to being uh the regimental commander of plebe summer, which is the highest ranking midshipman uh during plebe summer. And so I got to kind of have this almost like hero's journey of you know, the lowest low to the highest high. And um, you know, I just felt like I had a ton of perspective into the Naval Academy experience. Obviously, everyone's journey is going to be wildly different, and this is not an end-all be-all. But I knew that I had enough experience and knowledge to hopefully provide a little bit of perspective and help families. And so, again, as a result, the mission of Academy Insider really became trying to educate, um, have conversation, and do everything that I could to help explain to family members, loved ones, and future midshipmen what the Naval Academy experience is all about and what life in Annapolis is like and what the midshipman experience can consist of. And I'm not here to provide answers, but I'm hopefully here to provide a little bit of context, a little bit of perspective in a way that facilitates discussion and facilitates understanding so you can better relate and support with your midshipmen. And so that's the goal, right? And I'm very excited about that. And, you know, if you're listening to this podcast episode, it's very possible that you've heard other episodes that I've already put out. But if this is your first time, you know, listening to the podcast, first of all, thank you. Second of all, congratulations. I think this experience that you're about to embark on is going to be an incredible one, albeit difficult at times. Um, and third is that I'm here for you for this journey to help answer questions and to do those things. And not only will it just be the podcast, um, but you know, I'll use this opportunity to say, um, you know, and I'll put links to it in the description of the YouTube video. I'll put links to it in the show notes of the podcast. Or if you go to my Instagram page, Academy Insider, you'll be able to find a link as well, a link in the bio to download two things. Again, I've done, uh I've kind of created two guides to start. The first is a pleasummer terminology guide. It's not all inclusive. Will there be things that you hear that are not in that guide? Absolutely, but hopefully it's a good start uh to understanding some of the terminology, some of the things that you may hear, and also storytell through the guide as well to provide context in the case of which you would hear those terms. Um, the second is just uh a landing page for the class of 2030 families. I encourage you to sign up and subscribe for the Academy Insider newsletter. It's my goal to send information directly to you to help for the preparation of Pleep Summer and helping understand Pleep Summer and being a guide and resource throughout the entirety of the Naval Academy journey, but especially Pleep Summer. We'll have exclusive interviews with members of the Alumni Association about I day preparation. We'll have exclusive interviews in conversation and probably Facebook live groups or kind of closed webinars to have conversation and allow you to ask questions without the fear of like a public looking in and answering. Um, and so I will continue to work on that and I just want to offer that as a real opportunity for you to sign up and be a part of this community. I want to really foster and cultivate um, again, the group of uh what you know, what I'll call the support squads of midshipmen. And so um I really look forward to that. So I encourage you to sign up for that. Again, I'll be posting podcasts likely weekly as well to go through it. Uh, but to get a little bit more insight, a little bit more privacy, and some other things, I encourage you to sign up for the newsletter or download that Pleep Summer Terminology guide, and I'll get you included in all the resources that we put out. Now, just for the ending here, uh, you know, I want to keep this episode short. Uh, this is more of an introduction than anything else. Um The Naval Academy was the greatest decision that I um lucked into. Um I know it may some of you may be like thrilled. Both parents thrilled. In which case, awesome. Like you're already there. I'm so excited for you. You still may want this information, which I'm so excited to be a part of. Um I just want to be here to reiterate. Um I truly believe that even if you're not tremendously excited or you've you're even a little nervous, that your son or daughter is entering into an incredible life pathway that is not a four-year decision, it is a 40-year decision. It is going to teach your son or daughter how to have true grit and true resilience. So that way they go through difficulties now, so they are prepared to face even more difficult moments in their life when they're an adult, when they have a family, when they have to provide, when they have to be around. Um, I also think that you're going to be so tremendously proud and excited that your son or daughter, your midshipman is going to live a life of purpose, that they're going to make a positive impact in the lives of other people, that they are going to go above and beyond in service of our Navy and Marine Corps, of our government and in citizenship. One of the biggest things, and I just gave a talk recently at my high school, is that, you know, I think sometimes we associate service with the uniform, right? Like, oh, thank you for your service because you're in uniform. What I love about the Naval Academy is it's going to instill this idea that service is not what you do, is not the uniform that you wear. Service is the value that underpins the ethos of being a man or woman for others. That service is therefore not what you do via your uniform, but rather it is who you are as a human being. And your offspring, your loved one, your person is gonna go through this process, a really difficult process, that is gonna develop them and push them to become an incredible human being who is ready to be of service to our community, to be of service to our fellow human beings. And um I think that's really incredible. I think you're gonna be so tremendously proud. Um, you know, for a lot of you who are getting ready to pony up 250 grand to pay for like an Ivy League education or something like that, too. You may also be pretty juiced about the price tag, in which case I feel you. I know I know my mom and dad were also happy uh about that fact. Um but I think you're gonna be most proud of the human being that they become. This institution produces leaders, it produces warriors. Um and I'm excited for you to get to discover that. And so um, you know, there will be growing pains, there will be tough situations. Is it perfect? No, of course not. Are there things that are hard or maybe not ideal? Absolutely. Are there things that the institution, the Naval Academy, the Navy at large could be better at? Always. Um but they're gonna be in an incredible situation, and I hope you know that. So uh I look forward to going on this journey with you. Please reach out at any time, send me a DM, um, look me up on LinkedIn again. If you want to get a hold of me quickest, go follow me on LinkedIn, send me a message on LinkedIn, it's where I spend the most amount of my time. Um, but I look forward to going on this journey with you. I am so excited. Congratulations. Go download that guide, go sign up for the newsletter. Um, and I look forward to hopefully being with you along this journey. Congratulations. Thank you so much for listening to this episode of the Academy Insider Podcast. I really hope you liked it, enjoyed it, and learned something during this time. If you did, please feel free to like and subscribe or leave a comment about the episode. We really appreciate to hear your feedback about everything and continue to make Academy Insider an amazing service that guides, serves, and supports midshipmen, future midshipmen, and their families. Thank you.