by Scott R. Tucker

July 26, 2021

037 VWS Jason Williscroft

In this episode, we have Jason Williscrof, a United States Navy. After transitioning, he had a series of technology startups that led to a career in data management consulting for global financial institutions. Listen as Jason shares the "you can't do it alone" tips and a couple of tricks on how not to do it alone, and much more. 

Episode Highlights:

  • 09:10- The "smart and safe path" coming out of the military 
  • 12:59- The story behind Ring Knocker 
  • 22:00- What do veterans can do in finding their identity/purpose?
  • 26:00- Leveraging the internet to your advantage 
  • 27:45- The goal for RingKnocker

Key Points:

  1. Position yourself to thrive through anything because nobody knows what's going to happen.
  2. Activate your professional network, network to people who already understand you, and then do business with them 
  3. Leverage the digital skillset to connect to your community, to put yourself out there in the civilian world. 


  • “You can fail at stuff a few times, and it's okay. You can pick it up and try something different.”
  • “Nobody knows what's going to happen, and so it makes a lot of sense to position yourself to thrive no matter what. “
  • “Business is better than charity if you want to do effective things right because money is a strong indicator of whether you're doing the job well or not. “

Transcript of Episode 042   with Jason - You Can't Do It Alone

Scott Tucker: Welcome. Hi everyone. Scott Tucker here again with another episode of Veteran Wealth Secrets w where this show really is about opening the opportunities and the ideas. Whether you're active duty or you're in transition or you're a veteran, you're not quite doing something that you want to do, to see what the other opportunities are out there.

And that's why I'm so excited for today's guest, Jason Willis Croft who enlisted in the Marines in 1998 and then graduated from the Naval academy in 1995. Before he was commissioned in the Navy until two boom. And he was determined to become an internet millionaire, but within 18 months, that thing crashed.

And then we knew what happened with nine 11. So after a series of technology startups that led to a career in data management consulting for global financial institutions, adjacent plays every role from junior developer for hire to fancy pad CEO, as he says, and along the way, Jason picked up a few tips.

Specifically, you can't do it alone. And then he wants to share a couple tricks of how not to do it alone. So right now Jason is talking to us cause he lives on, in, on the island of Bali and Indonesia. So that'll tell you what, going outside the box could do for you, but his latest venture that we're going to get into is ring, knocker a community.

Current and former military officers who meet on a zoom call every Thursday night to redefine the concept of mutual in a lock-in file support. Wow. That is a lot of info to share. Let me bring Jason on Jason, thank you so much for joining us. I'm so excited to hear your story. You started ring knocker.

I think you reached out to me early on. Unfortunately, I had some things going on. I haven't been able to participate, but I saw it just blow up. I've had so many people talk to talk about how awesome it is. So now that my book's done and I can get out there and start promoting that, I want to join it.

But how are you doing, man? It looks like it's getting cold Rama. It looks like you're doing it.

Jason Williscroft: Yeah. Every day is about 80 degrees by 90% humidity and absolutely gorgeous. I love

Scott Tucker: living here. Very cool. I haven't been to Bali. I've been to Vietnam and Cambodia and Thailand, but definitely more beaches, but humid.


Jason Williscroft: About a thousand years. We, we came last December, so we're actually going to hit our one-year anniversary on the 18th of this month.

Scott Tucker: Very cool. Let's just start right there. That everybody's dream go live in a, in an exotic location when you can do it. Was this something you had planned out?

How do you. In Bali, leave it live in the dream. It, yeah, cause I mean that, that's a great place. It's I've heard so many great things about it. I'll just let you talk.

Jason Williscroft: I looked at the work that I do professionally is it's location independent now, right? So you used to be, we'd have to fly and visit clients, sustain hotels and all that.

But after a while they, the the remote tools got better and better, and the clients they'd rather not spend as much as they were spending on plane fare. So for quite a while, I was working remotely from home, which was Chicago for many years. And it just one day I met a guy, I met a guy who was actually retired NASA who splits his time between Chicago and Bali and We had a conversation and I was like, wait, what am I doing here?

I don't need to be, I don't know if you've ever been through Chicago, winter, but

Scott Tucker: yeah, I'm from Ohio. I'm from Northern Virginia.

Jason Williscroft: Yeah. Yeah. My girlfriend and I percolated up for a little bit and finally we decided to give it a try, right? So we came out here last December expecting to spend three months.

With an option to maybe extend a little bit. And there were some stuff I wanted to work on. One of the nice trade offs in a place like this is that a nice quality of life is not expensive. And so you can, if you've got a little bit of money in the bank, if you've got some ideas you want to work out, you can fail at stuff a few times and it's okay.

You can pick it up and try something different and it's, it's not like you're not going to be able to afford the next meal.

Scott Tucker: I have friends in live in Thailand on, on a Villa, on a hill, overlooking a beautiful ocean and they survive not just the rent, but everything, a thousand dollars a month, yoga instructor. And especially in this day and age where I don't know about this last year. Maybe you could tell us w with the ability to communicate, I lived in Europe for 11 years.

And so that was, it was a long time away from my family and the, the assumption is That, being away from that you're making a mistake by not staying in America and the ex-pat life. Maybe not for a permanent thing, but to try it out, like you said, you can make a lot more mistakes.

And cause go down to Mexico and Costa Rica, people think these things are scary, though, it's not safe at all that. Did you have any sort of reservations or based on your travel you probably already

Jason Williscroft: knew. Bob Bali is a different sort of place, right? It is extraordinarily safe.

It's one of the, one of the safest places that you can go. So you get to Mexico and it's gorgeous, like I said, it's not an issue here. For that reason, we felt pretty confident. And when we were still here when Corona virus hit.

Scott Tucker: Yeah. I was going to ask you that.

Did you get

Jason Williscroft: stuck? Yeah. So we're were actually right at that three month point and we were getting ready to to extend our visas. And in our case, what that meant was we had to leave the country and come back. So we had already planned a trip to Malaysia. It's called, we call it a visa run, to go do that. Kuala Lumpur is just a couple hour flight away and. We so neat thing about Bali. And I guess a lot of other places now is co-working centers, right? Like we work with coconuts, so we were doing that, so there was a place where we'd go every day and work, and a lot of other people, great bandwidth connection and all that.

And I was at home and the girlfriend was at the coworking place and she called me up and she was like, I hear all these people talking about this Corona virus thing and how they might close the country. We should leave now. Like maybe we should go like tomorrow, and so I'm like, all right, if he feels so strongly about it.

So we changed our tickets. We went to we flew to Kuala Lumpur on like Saturday morning, got the visas done on Monday less Kuala Lumpur to come back to. Bali on on Tuesday, Malaysia closed their borders on Wednesday, their borders on Friday, and that was it. Everything was locked down.

That, that was the story, right? So after that people could leave, but they couldn't come back. And so the population of foreigners. On Bali dwindled from something like 800,000 to 7,000, right? Yeah, we are Joseph's on Bali. It was pretty quiet for quite a while. And now, things are picking up.

People have figured out they can get business visas and I'm a little concerned, because we're getting yeah. Indonesian traffic is insane. It's just like the scariest thing you've ever seen on a motorbike. Oh God, he's hard on your throat. It was actually like, you didn't notice it for many months, because a lot of people now the traffic's picking up and there's a lot of foreigners. And there's some concern like what's going to happen. Are we going to get them? We haven't had the big coronavirus outbreak. It's been locked down early and hard. It's been really isolated.

I think we've been really lucky. Like we still got to breakfast, You have to wear a mask, but not everybody does. And you're comfortable. Who knows what happens, when the foreigners started coming back. But for the last year it's been

Scott Tucker: beautiful. Wow. I'm guessing part of this also has to do with how you came up with ring knocker, but before we get to that, I want to go back to your story of coming out of the military, like you said, in your bio during era. Yeah, clearly a smart guy knew what he wanted to do. What kept you from going the quote unquote smart and safe path, and, going down a route where you were, you're doing, you getting into startups as risky business, but you build skill sets and network. Pretty quickly I imagine, tell us what that was all like for you.


Jason Williscroft: probably less risk averse than I should be. All so it was I'd have my, my, my service commitment was up then, and I'd had 12 years in uniform at that point. So I was I was going a little tired of it. I was married to my wife and she wasn't really handling the separation well, That was like, it was one of those things where on the one hand, maybe it's time for a change.

We'll see if we can save the marriage. And on the other hand, everybody was like socks and dog food and sock puppets, and everybody was making a fortune doing almost anything on the internet. So I wanted, I was going to become an internet millionaire. I got halfway there. I found the internet.

And I got involved in a like a financial services startup I'm I'm a math guy, right? So I was building a proprietary trading systems and a little bit of a hedge fund involved and and it worked out really well for about nine months. And then very roughly ended.

And we did very well. We broke, even everybody else lost their shirts, but it was time to go. So that was the end of that. And I wound up running a gym in Chicago. That's actually how I got to Chicago gets stuck there for

Scott Tucker: 17. Oh really? I think, it's been 20.

And from that and people forget what boom was. Heck I was a sophomore at west point. Like I don't, I didn't even know it was going on. We're currently at, even with all these shutdowns and stuff it seems to be at least the stock market's doing well.

People have this, I don't know. Do you see that we're any sort of danger similar to what was going on back then? Where people are just. Not looking out for the risks that could be coming when it comes financially. Yeah.

Jason Williscroft: Yeah. Yeah. We can go off in a whole different direction.

I'd recommend. Nassim, Nicholas Taleb has a whole series black Swan and all that strongly recommend picking those up and reading them if you want to, if you want to a very quick master's course in how to think about risk. But long story short yeah we're in a bubble now.

We were in a bubble then two different bubble. I think that the bubble currently is being held open by what we like to call it. Quantitative easing.

The fact is much the same, right? I guess the short answer is nobody knows what's going to happen. And so it makes a lot of sense to position yourself to thrive no matter what, just make it a ring knocker. That's why we're there. The whole point is to. Thrive through anything.

So that's kinda why it's there.

Scott Tucker: Yeah. So how'd Rick knocker co come about? You must have had a lot of help along the way. Clearly you didn't do it alone, even though you're the leader of this it's it seems like it's oh, you might've had a big idea or whatever, but tell us a story.

Of how you came about creating ring knocker. I didn't do it alone, but I tried. That's usually how things start. It's I have this idea. I'll go learn all this stuff. And it's rare when you can really be a true solo for newer.

Jason Williscroft: What happened was a buddy of mine Navy class of 2013.

Sent me a a kid who was getting out of the service. Another Naval officer who's getting out of the service and he was interested in getting into data, which is my neck of the woods. And so just have a conversation maybe help them get oriented in this. And I had, we had a good conversation.

Like I just, I love the experience and I have not been, you mentioned building your network earlier. I'm a terrible networker, right? Like generally not what I do. So I've been mostly disconnected from the alumni community and all that. I've really after I left the service, I just went off, but talk to this kid and had this just a really uplifting.

Experienced. I'm like, oh, a bunch of my classmates had this. So I started a Facebook group and and invited a bunch of my classmates to Facebook has this kind of mentoring thing. Come do this. And the response was astonishing. I got like a hundred volunteer mentors inside of two weeks.

Never had more than two mentees. Okay. So we didn't really help a lot of kids but the message was very clear like you, knuckle draggers really want to help your shipmates. It's really wow. So I was just, we were thinking about like, how do you, how do we do that? How do we get, how do we get the message out to prospective mentees, blah, blah, blah.

And then coronavirus hit. And so it was actually my girlfriend says, why don't you just forget the zoom? Cause I was complaining about, how, what a pain in the butt Facebook wasn't Facebook. So we we decided to call it the ring knocker virtual meetup.

And and we just put out the word and we got 11 participants, and it was, it said Thursday night back in the states, and this is on March 20. And it was, it went way too long, Brightside scheduled, 90 minutes and went they were like two hours and 15 minutes. It was just like, it was completely awkward.

I had no guest speaker or anything. I was like the only person. And it was. Awesome. It was just, it was awesome. It was like this weird kind of class reunion sort of mastermind is a thing. And so we're like, all right let's do that again. So we did it again the next week and that time I think I think I, I actually managed to get speaker by the next week and figured out that maybe I should just keep it to an hour and a half and we just kept on doing it.

We did 35 weeks in a row, five weeks. W what we do here is we capture the video. We we publish like the full video of the call with my notes and deep links to all the speakers, which you can imagine that takes some time. And then we extract clips as people in the videos. Bullshit.

Excuse me. Can I swear here?

All right. Extract clips of people saying cool stuff and showing what they got. And so then we'd take the clips out and put them on the YouTube channel. I spent a lot of work. And at the beginning I was doing all of it. It was rushing. And, as, the ideas kept coming and we kept on doing it and we thought of more and more stuff, the website, all this stuff.

And and yeah, I just all my thing, my idea. So I just kept on doing it all. And at some point my girlfriend went into. Total revolt. You gotta get some help. So then you only went on to Upwork and started figuring out some of this stuff. I guess we'll talk about it in a minute, but that's really how it got started.

The idea was this is good. We're all sitting around at home, like maybe trying to work remotely, maybe trying to figure out what now, and this is what, this is a thing, Scott. We have. Our professional network is different. All right. If you went to Harvard, you took you didn't just take classes.

You had semesters devoted to how to leverage your professional network and your professional network went to hovered. It's it's a thing. But yeah, but if you went to the Naval academy or west point or someplace like that, what happened was you graduated, you went to like surface warfare school or the basic school in the Marine Corps and you wound up, Dragging a backpack or Khan and a ship out.

And that it's a thousand miles from no place. And your professional network was the other knuckle draggers around you keeping your ass alive. You never got that orientation until three months before you left the service and you got, tarp school, tough class. And that's it. That's all, so what you have is a professional network, fire and steel, and you have no idea what to do with it.

Scott Tucker: Yeah,

Jason Williscroft: it was nuts. So I'm like, all right, let's figure this shit out. I'm I'm certainly, I'm no expert in this clearly, right? Like I've literally, I've had the same problem. I never figured that out. What I can do is build machines, right? Like, all right, fine. I can build a networking machine.

My dad is a bunch of hyper-intelligent knuckle draggers onto a zoom call every week. And they're. With a little encouragement from yours truly is to figure out what to do with the opportunity. We mentor the young guys who are getting out of the service and transitioning. We help them figure out where to go.

And sometimes we hire them. And the other guys, we, we do business together. We become one another's client. Employees, sometimes business partners, and it's just the way it's worked at we've done it entirely by braille over the last nine months. And. Yeah that's the story and we're still figuring it out, right?

Part of my deal is I like many people I eat occasionally. So I'm I'm figuring out how to monetize it to a point where I can do that. Yeah. Yeah, honestly, the nice thing about businesses, you get feedback for people who are paying for the privilege, right?

There's skin in the game, in both directions. I'm a firm believer that, that, that business is better than charity. If you want to do effective money is a strong indicator of whether or not you're actually doing your job well. So that's what we're doing. We're, we're trying to figure out how to monetize it.

There's a whole, it's who I am. There's a whole technology platform underneath it, driving the thing that is interesting in its own. But as far as the community goes we are we're out there. With our sleeves rolled up and doing stuff.

Scott Tucker: Yeah. It's been amazing to watch.

I love a story of, Hey, seeing a problem, recognizing, a personal need and saying nobody else has shown me how to do it. I'm going to go figure it out. And you said it, business, there's 45,000 veteran service organizations. They, there are so many free help and advice.

And I've always argued for years then why aren't we solving the problem? It's it there's a lot of good will, but sometimes it gets confusing and stuff. And in veterans don't know where to turn. They get confused. They come to me and say, not only do I not know what I want to do when I grew up, there's too much stuff out there.

And it's you're just sitting around and they're throwing stuff at you like a fire hose and give you the same cookie cutter information that everybody else gets. You need to go out and find people that you want to be like, learn from, maybe work for free, or do some, maybe pay him some money to teach you or to get yourself into stuff.

What are you finding that people come into your group are doing differently maybe or whatever, what kind of feedback have they given where they're like, ah, I'm now I'm having a little epiphany is here and there. What can other veterans do? Whether they're gonna get, join your group, which I highly recommend.

Or otherwise to get themselves to help find their identity, their purpose.

Jason Williscroft: Okay. Let me share another number with you. You said 45,000 VSS, right? Here's another number 17 every year. There are 17,000 brand new. Former military officers every year. And that number has remained more or less stable since well, before the Vietnam war, there are hundreds of thousands and I'm just talking officers here, right? Hundreds of thousands of us out there. We are everywhere. We are at every level of industry. We are at every level of entrepreneurship. We are everyone. And again, that's just the officers, right? Leadership training. And then there's all the enlisted guys out there too.

Are the I don't I'm guessing here, but I would say that our pies are the largest cohesive. Let's call it an affinity group in the United States and we're completely invisible completely. So what does that mean? It means that when you're looking for a job, did you go to target.

Scott Tucker: I was, I got out in Germany and it was just like, it w it wasn't a huge military base. It was just like, yeah, go make sure you sign off on this and this paperwork. But I talk to people everyday. I talk to people everyday going through. And it is what it is.

Jason Williscroft: All right. So here's the deal sorry, I don't even know what tarp stands for but it's a class that's changing it.

Scott Tucker: Yeah.

Jason Williscroft: But everybody's supposed to take before you get out of the service. And it's gonna teach you how to network and how to write a resume and all that other bullshit. So one of the messages that they're going to tell you in tarp class, and you're going to hear it, you hear it all the time, at the meetups is I it's hard to translate.

Really good at operating a machine. Good. Awesome. How does that, how does it translate, right? What does that mean? How do you put that on a risk? And and you can tell the people who came to chart descriptions on their LinkedIn profiles. I'll read exactly the same way. So it's hard to translate that stuff.

And one of the, one of the big Tiffany's here is. If you know enough of us, if you're really connected to enough of us, you don't have to. Okay. Because pick 10 companies out there that you might like to work for, guess what? The hiring manager at two of them, knuckle, dragger, just like you, they already know who you are.

You have nothing to prove to those people. Your measure is already been done. So that's what I'm talking about. This whole idea of activating your professional network. You guys got one professional network in the country of people who I'm quoting my website here. Other people have, they've got experience of promises signed in ink, yours or yours assigned in blend.

Nobody. Absolutely nobody in country, in the world really who hasn't served the way that we've served has the mutual experience of trust and confidence that we do. There's just, if there's a difference between covering somebody's ass in a boardroom and covering somebody's ass in a fighting hole, it's not the same thing, it's qualitatively different.

What I would like to see is more of us instead of trying to explain ourselves to people who frankly couldn't possibly understand. I would like to see us network our way to people who already understand and do business with them. Yeah. And then, yeah, we can explain ourselves with our actions and with our performance, rather than trying to explain to a person who's never touched a gun.

You know what it means to service a machine gun?

Scott Tucker: Yeah. At the end of the day there's no SOP for how to get out of the middle of. But we're living as a veteran in the United States of America in the year 2020. There's never been, there's never been a better opportunity in all of human history.

I believe for a group of people to take advantage of stuff. We're in the internet age, the fact that you and I are having this conversation, we can, Hey, here's two veterans talking that would like to help each other. Gee, you know what, I can't everybody, figure out how to use this, but I actually think a lot of the problems.

Is, as you were saying you, when you, when we're out in the field, we're on a ship, you're not taking we're not getting the digital skillsets. And this is the kind of stuff that you should be teaching in taps class. How do you comfortably you leverage the internet to your advantage?

Nobody talks about it. Senator writing a resume, write a book start a podcast, Vega website, learn to blog like this is how you put yourself out there. So folks can get to know you and then veterans can, share, share info about you. So I love that you're giving people the opportunity and the skill set and knowledge to do it.

Jason, as we wrap up here, what's what do you see evolving as we're, as you're going through here and still. But what do you see? If we're talking three years for now, what's what are you right now? What's your kind of goal of where you see this thing going

Jason Williscroft: well. Okay. So we've got an, a number of people at ring knocker who are, these guys are amazing.

I got. Any ring, knocker meetup and often like a third to half of the people on that meetups, I'm 20 to 40 people have command experience, right? We're talking about people who's built and sold, not just one but multiple companies. And how does the other guys, the guys just getting up the group of people, these people have they got lessons to share and some of them are already sharing them.

What I would like to see and w we're actually we're working on, on, I hope that in fact, I've got a call with one of these guys working on it, working on the first of these right now. Our courses, right? Online courses is a cliche now. How do I do X, whatever X is, how do I get into this business?

How do I get into that business? If I wanted to do this, how would I do it? Lessons. Not just, Hey, sit around and listen. But actual face to face lessons taught by the people who've been where you've been and done what you want to do. So that's the sort of thing that education is definitely a thing now, but it's also the sort of thing that, that can really active.

What we've got to offer on one hand, put those skills to work on the other hand. Just as an example, if I've got, if I've got 20 people going through a course on, how did you government contract. Some of those people are going to found contracting organizations. Some of those people are going to want to work for contracting organizations and guess what?

They went through the same course together. So really just extending that, that, that connection from the meetups, which is primarily into something more directed and more and more directed something, something that they can activate into, careers into employees, into, real business.

So that's that's what I that's coming up for sure. For 2020.

Scott Tucker: Man I love the vision and I actually what I'm thinking and seeing right there, it's like somebody could come in network and take one of those courses to be an employee, but then come right back and eventually, to take to the next level, maybe start a business, that's where I want veterans to think.

Hey, just because you get out and maybe you translate your skills or find some sort of job. Keep exploring, be creatively exploring. And Jason you've clearly done that from your military career. I can't imagine, you're going from enlisted to the academy and then being right in the middle of the internet age, man, you've seen so many different things, so you bring a ton of value.

I'm glad you've come back into the veteran community. And brought that vision and inspiration. I'm looking forward to participate in more and and spreading the word. How do people contact you? Who should be a con who you look into to network with? They bring more, more into a ring knockers,

Jason Williscroft: Fiji, right?

Ring, Just go there. There you go to the meetups page, click the register button, and you're in, we're open to all current and former United States, military officers, regardless of service or commissioning source. We welcome everybody. Yeah. It's probably 80% Naval academy at this point.

We'll give you west pointers a little bit of a hard time, but we got VMI grads, we got coast guard grads. We got merchant Marine grads. We get plenty of ROTC people. It's an awesome bunch of people. My, my oldest attendee was Navy class of 1957 and my youngest attendee Westpoint class of 2020.

Scott Tucker: All right, man. You're killing them all. Wow. That's cool that you're getting, at the bar at the end of the day, this is all we have is zoom right now. So you might as well take up, take advantage of these types. Yeah. Yeah. I'm an introvert at heart. People wouldn't believe that, but when I go to networking events, I like going to conferences.

Cause I see all my online friends.

Yeah. Yeah. And I don't know. If that's going to happen again. And, but Hey, you can communicate with everybody online and still bring groups together. Still make relationships. Let's not be afraid of this stuff. This is the technology always wins, so we might as well learn to use it and embrace it.

Yeah. Jason, thank you again so much for coming on. We're looking forward to seeing what happens in 2021 with rings.

You bet. You bet. All right, everyone. Thanks for joining us on Veteran Wealth Secrets. Make sure you subscribe and share, especially this video. Cause when we're talking about networking, we want to get the word out. It has never been an easier way to do it. So please share and help support our community and yourself as well.

All right. Take care.

Jason Williscroft: Take care.

About the author 

Scott R. Tucker

Scott R. Tucker is an author, speaker and the founder of US VetWealth, a lifestyle and financial consulting brand that helps service members go from paychecks and government benefits to wealth and liberty. He likes to say, "I Help The 1% Who Serve Our Country Become The 1% Who Influence It." A West Point graduate, serial world traveler, military financial expert, and entrepreneur, Scott brings valuable experience and insight to those who have sacrificed so much in service to our country.

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