December 7, 2022

Breaking Into Cybersecurity: The Power of Accidents & Saying Yes To Everything with Jason Tugman, Director of Information Security - Ep. 74

Breaking Into Cybersecurity: The Power of Accidents & Saying Yes To Everything

Thinking Of Getting Into Cybersecurity? Here's How You Can Do It Without a Degree!

Today, we have Jason Tugman, Director of Information Security talk about how to break into cybersecurity without a degree, how he accidentally raised $1m for a startup, how asking the right questions can help your career, and more!

Jason is currently a medical device company's Director of Information Security and Data Security Officer. He has spent much of his professional career developing cybersecurity assessments and programs, including developing a pre-binding assessment and metrics aggregation tool for a $200mm Llyod’s cyber insurance line slip. Jason led the data compatibility working group for the DOE’s Cybersecurity Capability Maturity Model version 2.0 update (C2M2v2) and was a member of the API 1164 Pipeline Security Standard leadership & architecture team. Jason is a veteran of the United States Marine Corps.

In this episode, we talk about:

- How to break into cybersecurity without a degree and relevant technical experience
- How saying yes and asking the right questions can jump-start your career
- How Jason accidentally raised $1m for his startup, Digital Idiots, and his biggest mistakes

Ryan and Jason also talk about why you don't need to be incredibly technical to get into IT/Cybersecurity. Jason also shared his experience working under Oprah!

Enjoy the episode!

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Links and Notes from the Episode

Episode Transcript
Please enjoy this transcript or our episode!

Please note the transcript may have a few errors. We're human. It can be hard to catch all the errors from a full length conversation. Enjoy!

Jason: [00:00:00] Never be the smartest person in the room because the moment that you are or think you need to be, you have ignored all of the talent and wisdom of everybody else that is in that boardroom, in that soccer game, in that whatever you're doing, someone has a different opinion and approach that outweighs and embeds the organization.

Whether again, it's a team or a company or whatever group of friends playing Dungeons and Dragons, right? So never be the smartest person in the room and I walked away with that and I think it really helped my life, really enabled me to go into different fields and to not feel the need to be, well, yeah, I'm in charge, but that doesn't mean I'm the, I dictate, right?

A good leader takes all of the information around them and then congeals it, and then brings a strategy and a direction like a vector, but not, you know, Do this, this way for this reason, for [00:01:00] that. Again, that's a control and you can control yourself out of business. You can control yourself out of wisdom.

And I think that was a big thing that came out of that for me.

Ryan: Aloha folks, and welcome back to Degree Free, where we teach you how to get the work you want without a college degree. I am your host, Ryan Maruyama.

Now, before we get into today's episode, a couple of things. One, we send out a weekly email that has degree free jobs, degree free news, everything that you need to know in order to get a job without a college degree.

If you haven't already go to degree to sign up to get our free weekly newsletter. Second, the biggest thing that we hear is that people don't have a network. And so if that's you and you wanna start building your network, please connect with me. I'll be your first connection on LinkedIn. You can go to

I will put links to everything in the show notes. And without further ado, today's guest is Jason Tugman, director of IT Security. This is a great episode for [00:02:00] anybody that's looking to get into the IT space for sure but this is also a great episode for anybody that is thinking about making any transitions in their life.

Jason has an amazing story that we get into. He went from working on Oprah, being homeless in the Marines, to now director of IT security. It's an amazing story where we can pull a lot of nuggets of wisdom out from we get into saying yes in the power of accidents. If you wanna follow along with Jason's career and reach out to him, you can go to, connect with him on LinkedIn or on TikTok.

And without further ado, please enjoy this very very wide ranging conversation with Jason Tugman.

Aloha folks, and welcome back to Degree Free. I am super excited to have this week's guest on Jason Tugman. Thank you for making the time.

Jason: Absolutely, man. Glad to be here.

Ryan: This is an exciting conversation for me because we talked a little bit offline already and there are a lot of [00:03:00] rabbit holes to go down and so I will try to do my best at making this your very interesting life story as coherent and comprehensive as possible.

But in order to do that, I'd like to kind of just start at the present. Currently. Could you just tell the audience what you do for work, what your title is, and kind of what an average day looks like?

Jason: Yeah, sure. So, I'm the director of information security at a medical device startup based out of Oakland, California.

I live in Seattle, as a remote team. Most of my day is really around coordinating with all the different stakeholders. So we view our customers, which are both internal and external to the customer to the company. So our customers are actual customers, but as. In my title, my job is to really secure the network, secure the people, secure the processes.

And so our customers are also the people within the organization of the different business units. So [00:04:00] as you would imagine, a lot of my day is set up with meetings. I write and enforce policies and procedures, which sounds super boring, but I can get into why I love that so much. I think it's actually amazing.

I mean, I can tell you why in a second, but, and then the soup to nuts of being in cybersecurity, looking at alerts, looking at logs, getting scary, stuff popping up on my slack, saying Go look at this. And, every now and then, a big incident where it's all hands on deck and you have to really be on point and know what you're doing by then. Lastly, all those dividends pay off. If you treat your internal folks as customers, that means that you have a relationship with them. So when you're going to somebody with an emergency, they know who you are. They know your name. They have probably dealt with different processes before.

And if I do my job right, we're all terrified, but nobody's panicking.

Ryan: If you do your job right, you're all terrified, but nobody's panicking. I love that , it's a kind of like a respect for, what could happen. Is [00:05:00] that what you mean?

Jason: Yeah. We're a healthcare company, so we have patient.

Not only what's called PII, you know, identifiable information, but we have PHI people's health records. And so, in our job is very serious, and, so yeah, we just, we have to, we have to make sure that we're doing the right stuff at the right times.

Ryan: Definitely. And I was excited as well because you're actually our first guest on in this cybersecurity space.

And so for our audience, if you wouldn't mind just kind of breaking down, what is cybersecurity? like just at a basic level, because even for me, and I'll just talk for myself as a layman, I'm like ,cybersecurity like I have no idea what that means. I mean, obviously my mind goes to like logins and passwords and that's pretty much it.

Jason: Yeah. Yeah. And look that's a big portion of it, and in all candor, when I got into the cybersecurity space, and I mean this extremely, literally, I went on Wikipedia. What is cybersecurity? And I Absolutely, that is absolutely true but cybersecurity Well, I'll tell you what, it's people think it [00:06:00] is, and I'll tell you what, it isn't.

People think it's, hackers and you're doing cool stuff and digits are flying around. That's what hackers do and there's white hat hackers, there's gray hat hackers and there's black hat hackers, right? We like the white hat hackers because they're doing it altruistically.

And they will come to you with like a bug bounty or something like that with what they found. It's very academic but you see these things on TV and stuff, and I'm sure that exists but my job is the most dangerous person to a cybersecurity in, to anybody in cybersecurity. The most dangerous person is the people, or the most dangerous thing is the people, right?

So yeah, it is passwords. It is, but it's how you manage passwords. It's, is your network secure? Do you have right firewalls and right ports and protocols and things that, by the way, are very too technical for me. So you have to know where you're at in cybersecurity. So I am a cyber risk manager. I deal with risk.

I have very smart people on my team who are [00:07:00] far more the technical people, what I call the fingers on keyboard guys that are securing our firewalls. So people can't just come in, they're securing our email so people can't just come in, but they're also securing our email. So people don't accidentally send bad things out, phishing and, all these things.

But each of those are individual things, right? So, which make up a pro. So you have to put them all together to make a secure program and you can't just secure one thing but also, and this is the most important thing, is you can literally secure yourself out of business, you know? So we as cybersecurity professionals, we have to know what controls to put in place, but we also have to weigh those against the risk, right?

So risk is the potential of loss. If there's no potential of loss, there is no risk. So if there's no risk, Don't put a control in place, right? That's a waste of time, money, and resources. But then also sometimes an organization has to do risky things because we are a healthcare company. [00:08:00] We do different things.

And so you have to understand the objectives of the business, and you can't secure yourself out of business and that's the balance. That's where, again, why I focus on risk is because you have to understand the risk tolerance of your organization and every organization is different, and every business unit is different.

Finance might have a different risk tolerance than say, our data science team, which has different from our engineers, which are different from X, Y, and Z. Right. And so understanding that,

Ryan: Kind of going a little deeper, you said secure yourself out of business. Could you elaborate that on that just a little bit more?

Jason: Sure. Yeah. Look, there's a thousand in one controls, right? You can put a control in place that every time someone wants to send an email, they have to click the encryption button. They have to do this then it has to get processed in the back end by a DLP data loss prevention scan tool and it takes three minutes to send an email and it look in the intelligence community sometimes, hey, that's what you have to do, right?

But we don't work in the intelligence community [00:09:00] anymore. You have to understand like, do we need, for some people, for the people that few people that work in our headquarters, do they need badges? And do you have to have what's called a man trap where it goes and it swivels you in and swivels you out and things like that, that are just dumb because there's no risk there, you know?

Or the risk is very small. We wanna know who's in the building. We wanna know when they entered and when they left, and who their guests are. So if there's a fire or something like that, we know who's in the building, right? Or if a guest comes in and they try to get into our server room, which we don't have, we would have an alarm that goes off, right?

But securing yourself out of business is putting excessive controls in place, and a control is just a rule, right? It's just a thing that you have to do. Your mother probably has controls about you entering the house. You have to take your shoes off, have controls about doing the dishes after dinner, but she doesn't have you clean the house, top to bottom.

Every time you enter the house, that's silly. So controls are just that, [00:10:00] and that's what I mean by securing yourself outta business.

Ryan: Excellent. Now, just getting into a little bit into your background. I know that you currently work at a medical device startup. Is that much different from the other type of cyber risk that you were doing prior and how so?

It seems to me that like when I go to the doctor, I don't want, like, I've gotta rash on my back. I don't want that to get out to people, you know, or like these medical devices. I'm constantly checking my sugar and I don't want people to know that, like I'm pre-diabetic.

Jason: Right. And you know, Protecting people's health information is often the most intimate type of data other than potentially your taxes, right? Or your financial debt. It's very personal data. The way that my job is different working at a medical device company is that we have different regulations.

We have different mandated rules. They're put on us by HIPAA, by GDPR, which is the EU data privacy, PIDA which is Canada. Different things in India and for Vietnam and China and Brazil. I have to know all that stuff. [00:11:00] I don't have to know it all, but I have to be very familiar with it.

Because those are the guides in which we have to secure on top of what baseline, what sec, what we just call maturity, right? Or hygiene, security hygiene. We then have these special rules, controls that we have to do put onto us by the HIPAA security rule or something of that sort. So it's different because the context is different, but at the end of the day, if you know how to read a standard, which is not hard, but people don't take the time to do it.

If you know how to read a standard, you know what basic security hygiene is. Then moving from industry to industry, all you're doing is learning that extra layer, right? So coming from the energy sector into health sector in different, different things. It's just understanding that, that extra piece.

Ryan: Now, this is great because obviously you're at a director level, you know your stuff. We've got the intro to it down, and it sounds like to me that you've been in this space forever. Like this is all you've done [00:12:00] and I know that's not true and I would love to kind of go back to your past and where you come from as early as even the Marines.

I'd love to start there and go from there.

Jason: Yeah. Well, you know, in high school, one, I was the worst student. And when I say the worst, I mean the worst. I probably should brag about this but I graduated high school with the lowest GPA in the history of the school district. I got all Fs and one A and that A was in theater.

Cuz I love theater, but I was just, I was a bad student because I was a bad student on paper. You know? Was I dumb? No. Was I smart? No. Was I intelligent? Yes. And there's a massive difference there. So, I graduated high school, my Marine Corps recruiter went in front of the school board, physically showed up in front of the school board and he put on the strong, if you give this boy to us, we'll whip him into shape.

And he's like, you know, you [00:13:00] know,

he's like, don't worry man, I got you. He like, like give 'em to us and blah, blah blah. And the school district's like, yeah, go to Marines. And I'm like, that's what I wanted to do the whole time. So, you know, but, so yeah, I went in the Marine Corps, but I went in the Marine Corps knowing that I was only gonna be in for four years.

I wasn't gonna make it a career because I knew that I wanted to get out and I wanted to be a theater director. I wanted to be a director of, of films 'cause who doesn't and so I went in Marine Corps, did my thing. I think Marine Corps did some amazing things for me as a person and it gave me courage and dedication and confidence, in all those things.

I will say that when I was a Marine, it's very different than being a Marine today. It's a whole different conversation but it gave me a lot of tools, personal tools and then I got out and I went to college. I know this is the degree free, but I went to college, I was in, I went to Columbia College in Chicago for film, as you would imagine and, first year, freshman year got my film and they got picked to be the top film and go up in this competition, blah, blah, blah and my [00:14:00] teacher was like, no, Jason's film is disqualified. What? It was picked. And it's because he was like, we asked you to make a narrative film and you made an experimental film.

I'm like, I don't think so. It's beginning, middle of end, but he goes, I think you're too, too, too experimental for us. I said, okay. So I went across the street to the school of the Art Institute, which is pretty famous school and I gave him my film and I was like, and they're like, yeah, scholarship.

And I was like, sweet. So my, second half of my, no, no, no, it was my first semester of a sophomore, finished that semester at School of the Art Institute, studied performance art and stuff. Cause they didn't really have a film program, like 40 stuff and at the end of that, they're like, yeah, Jason, we just think you're too narrative for us.

And so they pulled my scholarship and I was like, look, I can't win and I was frustrated and then I was like, well, fuck you and I dropped out. They, it gets a little weird from there. And then I accidentally raised a million dollars for a startup that I didn't have [00:15:00] to. Different story.

And that's when I really dropped out of school. Cause I was like, well, I can do this or I can do that. And at the same time I was working in theater and I kind of got a love for theater. And so my startup was this digital video startup called Digital Idiots. We were around for about a year and a half like everybody else.

But then I did that, and then I left that startup. Jason, can I just interrupt you right there?

Ryan: Sure. You. Right. I have to ask. Accidentally raised a million dollars for, this was for digital. This was for Digital Idiots?

Jason: Yeah. But that's before the company existed. So I made a nonprofit and my whole thing is I wanted to make films the way that people make theater, right?

You can make films that are local 'cause theater is local, and then sometimes an actor and a theater gets famous, like David Schwimmer from The Looking Glass Theater is now David Schwimmer. But he was just a theater guy, in Chicago. We hung out at parties and stuff and then he was like friends.

And then, that was a name drop by the way.

Ryan: Yeah. That. That was actually [00:16:00] a big name drop. I don't know if, I think that for the audience listening to this, I'm not sure that they're gonna know who David Schwimmer is, but

Jason: Ross from Friends.

Ryan: Yes, exactly. it was not lost on me.

Jason: So anyway, so I had this nonprofit and it was a 501(c)(3) and I hired an accountant and I met the accountant at a Starbucks across the street from my house, and it was a Saturday.

And he was like, do you think you could make this into a, like an internet? That was a dot com is the word we used at that time and I was like, I don't know. I've never thought about it. And he said, okay. And I had brunch with him and this other guy named Ray Maga on Sunday and Monday I was in the 42nd floor of one South Wacker in Chicago, working out of Ray Magos law firm, and he started bringing his buddies in.

He was like, Hey, this is Jason, blah blah I didn't have a name for it. I didn't know what we were gonna do. By the end of that week, I had, I probably had $150,000-$200,000 in the bank. No employees. Hired 15 people to do a company that I didn't, [00:17:00] we didn't have a business plan. I didn't. And it was like, name it.

And I was like, well, it's, I'm an idiot. So Digital idiots. As, you know, raise about a million dollars. For a company that I did not want, I didn't, it was just, but I was like, that seems fun. Which is pretty much like the course of my entire life is like, Ooh, that's interesting.

Let's go do that. Ooh, that's interesting. Let's go do that. And so I did that thing, failed miserably, learned a lot, got really depressed. Was homeless for a little while and joined a circus and got my life back on track. So, you know, as you do.

Ryan: Yeah. As one does exactly. That is an amazing story. Thank you so much for.

I'm telling you, there's so much, there's so much in there. Okay. So when you said you failed, like what actually failed of it? Was it just that? Cause I, in preparation for this interview, I did, I went and went on the way back machine and looked at, and like, and so I,

Jason: I [00:18:00] haven't even done that.

Ryan: And it was, that's so fun. Like when people, and we kind of talked about this offline, like about, well I have more to talk about of your past, but when you look at people's past and just see like, What they were doing at the time and where you've come from. What part of that failed?

Was it just that you didn't, like you were a young entrepreneur, you had no idea.

Well, just cause you had the money.

Jason: Yeah. I wasn't an entrepreneur. I was a jagoff that was sitting at a Starbucks talking to an accountant. You know, I'm not a, at the time I was not a business person. I literally worked in theater.

I just didn't know what I was doing and I didn't, I was afraid to ask questions. I was afraid to not pretend. I was afraid to ask because I was afraid to be wrong. And I was afraid, like, oh, I'm the CEO air quoting. My actual title was digital, was Head Idiot. I think it was something like that, because, you know, it's dot com you have to give yourself a little spicy name.

I was like, I'm the head idiot, chief idiot. I was the chief idiot that

I was the chief idiot. Yeah.

But, you know, I just didn't, [00:19:00] I was afraid of not knowing things and at that time, I dropped outta college. I didn't have a college degree and I was just afraid of not knowing. And so that I was gonna get found out, that I was, oh, you're not a businessman.

Well, no shit man and I was just afraid. And I didn't ask the right people, the right questions. And I was surrounded by very smart people, very smart investors. And I just didn't tap that knowledge. And one of the things, an axiom that came out of that for myself and I've lived by this ever since.

It's translatable to every facet of your life. And it is simply never be the smartest person in the room because the moment that you are or think you need to be, you have ignored all of the talent and wisdom of everybody else that is in that boardroom, in that soccer game, in that whatever you're doing, someone has a different opinion and approach [00:20:00] that outweighs and embeds the organization.

Whether again, it's a team or a company or whatever group of friends playing Dungeons and Dragons, right? So never be the smartest person in the room and I walked away with that and I think it really helped my life, really enabled me to go into different fields. To not feel the need to be, well, yeah, I'm in charge, but that doesn't mean I'm the, dictate.

Right. A good leader takes all of the information around them and then congeals it and then brings a strategy and a direction, like a vector, but not, do this way for this reason, for that. Again, that's a control and you can control yourself out of business. You can control yourself out of wisdom and I think that was a big thing that came out of that for me.

Ryan: Yeah, definitely the leadership, the lessons in leadership are huge and I think a lot of people discount it when [00:21:00] maybe, let's say you're working in retail or you're working fast food and you're just like, well, I don't have anybody underneath me. I don't like, how is this leadership stuff, relevant to me?

And it's very relevant. I mean, one, if you can learn to, if you can learn to lead, then eventually you can become a leader but even if you never end up leading a team, if you can put your, if you can have empathy and put yourself in your leader's shoes. You're now thinking two steps ahead and be like, okay, well if I was the boss, I would be thinking this.

I meant I'll go skate to where the puck is going, you know?

Jason: Right, right. You know, they company I'm at now, we just redid our company values. The five things we had our mission statement and I was on that, that selection committee and we worked together. Cause a small team, we had value these five values, but they were made when the company was very small and now the company is, under 200 people.

So we're mid, for startup and, so we redid our values and one of the values was act like an owner with the original one and we [00:22:00] changed that to be a leader because not everybody, to your point, not everybody is an owner right now. In the early days of the company, everybody was, literally. Now, we can't ask, , my junior associate whatever to be an owner.

He's like, of what? But we can ask them to be a leader, because you can lead yourself. You can lead in a room of people far more senior than you. You can lead by example of having a calm personality, of bringing good ideas or just bringing ideas, right? Feeling that, that you can lead yourself. You can lead a conversation, you can lead a project, you can lead an effort.

Even if it's an effort of one, you can still lead that and one of the things about leadership is you can learn just as much from a good leader as you can, a bad one. And by that, you can learn from a good and you can learn from a bad boss because I've never [00:23:00] seen a leader that is bad. I've only seen bosses that are bad, and there's a huge difference there.

So one of the best leaders that I ever worked with was, interestingly not in the Marine Corps, but it was Oprah Winfrey and I had the opportunity to work for her for a while, and I think of some of the simple things that she did that really showed the direction of the organization that trickled down to her managers to their managers and then to me, right, four or five steps down. But it red downed down to us and it set the tone for the organization and it set the tone for how of how we work and how we, our dedication and how we don't work, what we don't do. Right? We don't drive people. We just ask people. And you'll be surprised.

You raise your hand to stay late because you're just as committed to the show as everybody else is, as she is. Right?

Ryan: Absolutely.

And so kind of getting us back on track [00:24:00] with, your story, you kind of alluded to where you end up, but I kinda wanted to just since you threw the nuggets out again, you were homeless for a little bit and then you said you joined a circus.

Did you actually join a circus or ?

Jason: Yeah. No, no, no. Yeah, yeah, yeah.

So there was a small circus in Chicago, ended up accidentally working for, and the word accidentally is, will come up a lot in my life cause I accidentally, people just ask you to do something and you're like, yeah man, that sounds awesome.

Let's do that and just do it. It's super fun. It's a great way to live and yeah, I was homeless. I was sleeping behind this copy machine at this mailbox, et cetera that I used to work at, but I still had the master key so I could, I slept behind this copy machine for a while and, but I was working for the circus, this, which is kind of like in a theater.

It was literally called Where Theater and Circus Collide was the name of the show and, they, this guy Jeff Jenkins, was the form, was the last head of the Wrigley Brothers Clown College where there was actually a college for clowns and he had, [00:25:00] he was a head of that and he went and did this show called Circus Smirkus which is a summer camp for kids.

But it's like, the minor leagues, like there would be like circus scouts that would come in and be like, yo, and they would take Indra and Solano Sattar and they made them into contortionist in Vegas and they took, Andrew and they took a bunch of other people and you now work for Surplus le you now work for whatever.

And so it was very serious and we did, I forget, we did, I used to know it was like 150 shows in seven weeks in 17 towns or something like that. It was some crazy, crazy, crazy number and there was a big top. So we raised a big top back down, but you know, it gave me some money. It recentered myself a little bit.

Went in, went back to Chicago, did a, my buddy, I'm still friends with. he called me one day and he said, Hey man, I'm double booked for this gig, to load in these lights, for this thing, it's called being me a master electrician for a theater. And [00:26:00] he says, can you do this load in for me? I was like, sure.

Who's the lighting designer? He goes, oh, so and so. I was like, well, I've never, never heard of him. He goes, yeah, I don't either, but you know, it's a show, it's big show and it's, you know, so I went, I just did, went in, did my job. It was just he and me and this guy. Cause it's, kind of doing the load end bit.

And I worked for this guy who I'd never heard of. I worked in Chicago at that point for 10 some years and I'd never, and this theater's a small community and, you know, just do a good job as you do. I don't wanna embarrass my friend who brought me into the gig, paid really well. And at the end of the week, the guy was like, Hey, you're a good worker.

I was like, thanks and he says, I'm leaving town. I'm moving to like Vermont or something. It was Connecticut. And he says, I need somebody to take over my role. And I'm like, well, I'm not really a designer. He goes, no, no, no, this, I just do this for fun but I'm in charge, you know, I need to pull somebody forward and, and offer, you know, basically give them my job. And I was like, well, what, what do you do? Like, I've never heard of you. What [00:27:00] do you, and he goes, oh, I on the lighting crew for Oprah Winfrey. And I was like, what? He goes, yeah, we just, we worked really, we just had a great relationship this week and you worked really hard and I think you'd be a great replacement for me at the Oprah Winfrey show.

And I was like, motherfucker. Like, that's how that happens, right? You just, you don't know who you're talking to, you know? And it doesn't matter. You're just doing your job, you're doing a good job and then next thing you know, you're at a coffee shop raising a million dollars, you're working in theater and you're now working for Oprah Winfrey and you're just, you know, you just, I don't know, man.

You do good work. You're a nice person. Don't be a dick. You know? And just be humble. And by humble, I mean, don't be the smartest person in the room. Say what you don't know and ask questions, ask intelligent questions, that's how I got to Oprah Winfrey

Ryan: With now we're at Oprah. You said that she was the best leader that you've worked for. [00:28:00] Could you just give like one example of a leadership quality?

Jason: Yeah. It's my favorite story. It's my first day. It was the last episode of the 19th season and the 20th season. We're gonna rip down the set and we're gonna build this new set, which is the one that she retired on the blue set.

And it was our last day and she took, it was my first day but she took the entire crew, like all the producers, and they went across the street to this bar and they just threw this big, like, celebration dinner. Except for this, my boss, the, one of , project men projecting managers, came up and he was like, Jason, you're gonna work with Bob, right. And so Bob, you're not gonna go to the party, you're gonna stay with Jason, you're gonna take down these curtains and Bob was pissed. He's like, oh, I mean the whole, we're working for like five hours and we're over there just getting drunk and Bob the whole five hours. And I'm like, this is my first day.

You know? And Bob's like tearing down these curtains and he's like, he's grumbling the whole time and blah, blah and he's very five hours . And they all come back in, you know, cuz it's literally across the street. They all come back. , [00:29:00] like hundred of them. And they're like, whoa. We're going like, we're going to Hawaii.

Woo. You know? And this Bob was like, mother, what? And they're all like, we're going and they're drunk. We're gonna Hawaii .And Bob was like, about to lose his stuff, man and so our project man, our program manager came up, production manager, I keep saying, uh, or production manager came up to Bob and he was like, Bob, you know, only people that can go on the trip are people that worked over 500 hours on the show.

And, you know, and he was like, what are you talking about? I did the whole season. I did blah, blah, blah. How can I not be at 500 hours? And he goes, you weren't at 500 hours, you were at 495 hours and you just worked five hours. Congratulations, you're going to Hawaii. You know, and to have that freedom and that ability to recognize the, first of all, the ability to recognize, but then give [00:30:00] people the confidence to make those managerial decisions.

You can't tell Guy why. You just have to kind of trust that maybe he had a plan and maybe they didn't. But in this particular case, they had a plan. And so this guy went to Hawaii with him and his, that one person, they got a credit card with like $2,000 on it for spending money. Everybody flew over, they stayed at the Oprah Mansion thing, and they all went and they had a great time because it was just employees and that's, it was just a great example of when you make a good team, then that team has the ability to make the right decisions for their team and it goes down and down and down until it gets to Bob where he needs to make five hours so that he can go on this trip, which probably costs 10 or $15,000. Oh, she's a billionaire. Billionaires care more about money than you think. That's why they're billionaires.

But you know, that was just a great example and it was my first day and I was like, [00:31:00] huh, this is gonna be an interesting.

Ryan: That is awesome. And I imagine, did Bob get informed, like he got informed right then, like right then and there? Did his whole demeanor just change?

Jason: Oh, of course, because he almost had that look of like, I knew you guys, like he, but I would be pissed too.

He missed the party and he missed his, party with his friends and Yeah, I would've been mad too, 'cause you can't be told the reason because that would be, the cat's outta the bag at that point and so Yeah.

Yeah, he was, he was, he was freaking thrilled. You know, so

Ryan: And so we go from lighting the Oprah set, Right?

Tearing down these curtains and getting ready. I think you worked there for a little over a year.

Jason: Yeah, a little over a year. Yeah.

Ryan: And now we're working in IT.

How does that, how does that happen?

Jason: Yeah. Accidentally, Oprah at the end of the 20th season, she told us that kinda the crew, she says, Hey, look, [00:32:00] I'm retiring at 25, yet 25 years, and this is the end of the 20th.

I'm telling you this now so that you can make your professional plans, and she told us five years in advance or four years in advance at that point. And I knew that if she was gonna go another 10 years, I probably could have been a production manager. You know? I kind of, anyway, and but I knew that in that four years I wasn't, I was just gonna kind of remain this lighting guy and I didn't want to be a lighting guy, you know?

And so I made the decision to, to leave the show and I went and I just got this random job working for this company. I was doing their website, cause I knew how to code, but like really bad, you know? But I, the whole startup thing is because I taught myself how to code. I missed that part.

But, you know, so there's like some layers there. So I taught myself how to code. Weirdly, by reading the big yellow book, you know, the bible, PHP Bible? That's 2000 pages. I read that fucking thing. Who reads it? I did , I cover to cover, [00:33:00] I read it and I just was trying stuff. Anyway, that's how I learned how to code.

So I knew how to code. So I did this thing and I had made this fan website. cause I was playing this video game called Star Wars Galaxies and I made this fan website, loot something, I forgot what I called, it doesn't matter, but, it was just a fan site and I made some money on the Google ads and stuff.

So I was making like 400 bucks a month, and my rent was 425. I had three roommates, which five and so I was like, cool. And I was making this fan website, and I was in this guild of Video Gaming Guild and this guy named Yak, Y A K Yak. He and I are good friends. We've been in this guild together for two years.

Nobody's talked to each other. This is like before the days of like, discord and stuff. So we're just typing in these message boards. We're playing a video game together. And, one day Yak sends me a, hops in my hops in my dms, if you will, and he says, Hey man, I see you're a pretty decent coder I wasn't.

Do you wanna come out to Washington DC and work for me. And I was [00:34:00] like, one, what are you doing? I live in Chicago and no, like, I was kind of pretty happy doing what I was doing. I was making $55,000 and I remember when I got that first salary, they were like, oh, we're gonna pay you $55,000. I ran across my, around my apartment and be like, $55,000.

How could I spend that much money? Oh my God, I'm rich. I'm rich. Bitch like I was. I literally was. I literally was like up and down my apartment. I was overjoyed $55,000. What? And so he was like, he goes, no, just come out to DC, you know? And I was like, well, what are you doing? And he goes, well, we'll get into that.

I was like, that's shady, but you know well, and so they called and like his boss called me and he was like, oh, we got this project we went to work on. I'm like, why me? And it turns out that this project well, so I finally said, yes, fine. They broke me down and it was like July 3rd or something like that.

It was July 3rd. It was [00:35:00] Friday, tomorrow, Saturday was July 4th cause the town numbers work and they, I finally said, yes, they're gonna pay me $72,000. Uh, and. They were like, okay, cool. Be in the office on Monday. And I was like, I live in Chicago and they're like, yeah, and tomorrow's July 4th.

Yeah. Be in the office on Monday. Where am I gonna live? They're like, oh, we'll put you in a corporate condo for three months until you find a place to live. Okay. What do I do with all my stuff? And they're like, pack some bags. Come out here. And they, I swear to you, they said this to me. They're like, how much is everything in your apartment worth?

And I was like, huh? Like, how much is everything in your apartment worth? True fucking story. I was like, and I looked around, I'm a broke fucking artist. I'm like, and I was like, $5,000 or whatever number I gave them, you know what I mean? Was like 1 billion dollars. And I know it was like five fans.

They were like, okay. like, and I just fucking left and this, I'll tell you this because it was fucking fun, man. A friend of mine named [00:36:00] Mattie Johnson, I called up Mattie and I said, Matt, who we worked in theater together. And, I said, Matt, man, I gotta leave. He don't ask questions, it's just whatever.

And, so he's like, what do you need? And so I sent out a, I made a list of everything that's in my apartment, like dishes in the dish drawer, posters on the wall, sheets on the bed, television in the room. Like when I say everything, I mean everything. I just made a list and I sent out an email to all my artist friends and I was like, come over, pick my bones.

But the rule is, only take what you need and at the end of the day, you can take what you want and Mattie, being a good friend on July 4th, sat in my empty apartment and friends would trickle in, oh, I need an air conditioner. Oh, I need this, I need that and for months I was getting emails from friends of mine being like, Hey man, just wanna let you know I just moved in a new place and I took your dishes.

And so every time I eat off those dishes, I think of you, Hey man, I got your air conditioner. And it was just the best thing, man. I just gave [00:37:00] everything away. And so the job in DC. I was working for a company called Mitre. Mitre is a federally funded research and development center.

They make prototypes for the Department of Defense Intelligence Community. All in, yeah, a bunch of other people. And this was a DARPA project. DARPA is the research arm of the army and they needed somebody who knew how to program, somebody who had experience in a forward operating base, and someone who knew what an NLE was, a nonlinear editor.

So they needed somebody to make a program so that platoon leaders in forward operating bases could go on patrol, take all that video. Edit it together and send it back to KOAs continental United States. So what's the population of people in the United States that our former military knew how to program and had a on how to train people to use digital editing systems.[00:38:00]

I don't know the population's. Like two maybe, which makes sense why they were so persistent in calling me. So they're like, do this thing. And so I was like, okay. I got out there and I was like, this is what I'm doing now. And so that was my first office job and I ended up going out to DC.

Sounded cool, so I did, and I was out there for 11 some years. And again, Mitre has the largest population of PhDs of like any organization, right. And of any, research company. Everybody, everybody's a p has a PhD and I'm sitting over here with no degree. I'm sitting over here with like a year and a half of college, and I'm in the same room and I'm giving my opinion and I'm talking to them, and it's terrifying.

You know, and I, I often say, and this, I think this is true, that one, just don't be afraid, but at the same time, if you find yourself, into new waters and you [00:39:00] don't feel terrified, you probably haven't lept far enough. And I can tell you that every job I have had up to and including, Oprah and, working at Mitre, I was terrified.

I did not know what I was doing and I think one of the things that you can do in life is learn how to learn and it gets to that thing at the very top when we talked about standards and we talked about, cyber risk controls and things like that. Well, I learned how to learn and when I tell people, they're like, oh, I could never learn that.

And I'm like, you're right. You you can't learn the thing. You can't learn to be an amazing programmer. You can get to being an amazing programmer. Right. But you learn because you start really small. And I equate it to, X-Men the comic book is how I learn how. This is true. My very first job when I was 13, whatever I was making, , yeah, my first job was at 13.

It [00:40:00] was totally illegal but yeah, I made $10, I made $10 a day at this pet store, cleaning the cages and it was an eight hour day and I made 10 bucks a day, cash under the table cash. And I would take that 10 bucks as 13 year old. And I walk over in the same strip mall and I would walked in the first day and I had my $10.

And I was like, I want some comic books. And the guy's like, sure. So we're walking around and I was like, oh, spider-Man, whatever. And he was like, X-Men, like I've heard of X-Men. He goes, and the guy behind the counter was like, no, you don't wanna read X-Men. I was like, why? He goes, well, they're on like issue 562.

You know, you won't know what's going on. And I was like, Well now you just, I'm gonna do it because, fuck you. So I was a 13 year old and I was like, bet. So I put my $10 down and I got two episodes or two editions of X-Men. And he was absolutely right, man. I opened up that comic book. I, there was plot lines that went back two years.

I [00:41:00] didn't know what was happening and I set that one down thoroughly confused. I don't know who these characters are, who enemies are this Arc, put that one down and I read the next one. Still didn't know what I was doing, but I'm persistent. And so I went back day after day and I got more and I got the next one.

And I got the next one and I got the next one. And about, I don't know, three months into this, four months, it doesn't matter, into this reading, this X-Men, I opened up the issue and I was like, I know that character. Oh, that's that. That's what happened. Oh, that's that bad guy. And I read the next one and I was like, oh.

And then all of a sudden you start to understand because you've moved along the plot. Do you go back to issue one? No. When you start to learn programming, do you go back to the first programming language ever written? No. You start where you are and all of a sudden over time you kind of catch up. And so I view learning and I [00:42:00] tell a lot of people this and tell you and your listeners that too is that learning is like reading X-Men.

You're not gonna know what's going on, but just be persistent, keep reading, and soon enough you will understand the plot line. And that's how you learn. That's in the simplest form. That's how you learn.

Ryan: Amazing. And it's just that persistence as well, right? Like your first two or three issues. Like you said, you have no idea what's going on.

And that's the same thing with anything else. Whether it be theater, lighting or learning how to code. You're like, somebody just tells you, Hey, put that light over there. It needs to be at, it needs to be about 45 degree angle to the subject's face. Like, why did do that? Well cause the shadows and don't worry about it.

Just do it. You, I mean, and like you'll learn the rest. You'll learn the rest later with all of it will be filled in with context. You'll be able to read between the lines later.

Jason: Yep.


Ryan: With, I just wanted to touch [00:43:00] on the Nle. So for those listening non linear editing, is that like Adobe premier?

Jason: Premier? Yeah, in fact it was Adobe Premier, like Final Cut Pro or something like that. you know, we did it for the DARPA project. Just using flash video. You can actually do a lot in manipulating video using flash animation which was interesting and so we did that now about three months into this.

So my first office job, I didn't know what I was doing and about three months into this, they came into my office. You co-share an office person. Shared my office, she was robotics, so there was always like little robots, little on tracks, like running around. Its weird. Mitre was a cool place to work, man.

And they came into my office like, Hey Jason, DARPA project, DARPA funding got cut and I was like, oh, okay. What do I do now? Like, we don't know. Figure it out and I was like, what? Like, yeah, just find a project. And I was like, huh. So I just fucking went knocking on doors. Hey man, what are you working on?[00:44:00]

Oh, nothing. Can I help? Sure. Oh man, what are you working on? Can I help? Sure. You know, or No, go away. Who are you? But you just find your way and the time. This is research company and I moved over. This is one of the things, and I think that one of the, this is from. I think one of the things that happens with people that don't get college degrees is they tend to take a different path in life.

Their life can be a little windy. Their life can have fits and starts, their life can lead them in ways, degrees in which they never knew that they would go in. I never in a million years thought that I would be doing any of this stuff. I thought I was gonna be, working at theater and film for my life and I was gonna be very happy with that.

But I just said yes to really interesting things and I think that one of the powers that we have, in the fact that we have to make our life, our life isn't on a path Is that we think differently. We process differently [00:45:00] and I was in the room with all these PhDs and these are kids, people, you know that did excellent in high school.

They went directly into college and they did excellent. They did probably a master's program or an MBA or something and they'd got a postgraduate degree then they went and got their PhD. Right? And so they've been in school from the time, they graduated high school until, this is their first job, just like it was my first job.

It was their first job, but they had done this path, so they knew how to do robotics really well. They knew how to do whatever they were doing, human language interpreting. They knew how to do all that stuff really well, but they didn't know how to think, right? They knew how to do their thing, but they didn't know how to think or process or creatively approach a thing, right?

We go in, we make stuff up because we have no other [00:46:00] context. And so one of the things that ended up happening is I would be sitting in a room and I'd be like, what if we do this thing? And they're like, yeah, because they've learned how to learn using their guide rails, I didn't and so I got to be known as the creative guy and they would bring me in.

They're like, Jason, we've got this problem. And I'd like, walk me through it. And like, I kind of got this reputation of just like, and I was like, it's not that I was super smart. I was just like, oh, okay and you whittle things down and it's like, well, what we do is X, Y, and Z and I'm like, don't tell me how, I don't give a crap about how, tell me why.

Why are we doing this thing? Oh, well, okay, now walk me through it. And in telling you, once you, once you get to the point of why, then they tell you how. And you're like, well that doesn't match this. Or you're getting off, you're doing it. You're the why is wrong? The why is actually Z. And then once you start [00:47:00] with that, and you can be a creative thinker, ADHD also helps by the way, because, we're bottom up thinkers and, but yeah, I got that reputation and so I very quickly moved over to the intelligence community and I was doing some work.

I spent probably most of my time at Mitre working the intelligence community and I became the department chief engineer and the entire department was made up of mostly PhDs that were working in the intelligence community and I was the department chief engineer. Oh. For the only reason that I, I knew how to think and I knew how to ask why.

Ryan: There's, it seems like one of the things that I try to talk about on this podcast is being willing to fail. It's something that I really have you, I'm not expecting yes but have you ever read that book? Mindset? I think it's Angela Ack. Anyway, there's like a growth mindset and there's a fixed mindset.[00:48:00]

Basically to wrap it up, I was raised in a very fixed mindset, household of Asian people. They say good job for doing something smart, and they don't really say good job based on how much you failed or how much work put into it, right? Like if I win a chess game, good job. It didn't matter if I like tried really hard at it, if I lost bad job, right?

I could be playing the best player in the world playing Magnus Carlson and if I lost, it'd be like, you're a loser. I'd be like, you tried your hardest. So coming from that mindset, coming from that background, , you don't really want to get out there and you don't really wanna fail. And this is something that I still struggle with to this day of getting out there.

And I think it's really, really important for everybody, but especially for people that are degree free, that are trying to live this life without it, because of exactly what you were talking about, of like when you're early in your career and that might even be a cop out, I think at all [00:49:00] times, saying yes is probably better than saying no until you get to like a certain place of which most of these people aren't listening to this podcast but you just have to say yes and know that you're going to fail and that it's okay. You're going to, everything else you're gonna learn along the way and I think that's where you get that out of the box thinking.

Jason: Yeah. I think, I think that people so fail fast, right? That's, the term of art and it sounds really great on paper, but it takes trust, trust in yourself, but it also takes trust in your leadership is, what, how risk tolerant is your leadership and if they are very risk averse, failing, is a viewed as a negative, whereas the way it's not the fact that you fail.

It's how you fail. And when you fail, that [00:50:00] makes fail your good. Fail fast, okay? Try something but you can't just try things. You have to know why you are trying something. What is your hypothesis for this effort? Once you in science prove a hypothesis wrong, you form a new hypothesis based on that knowledge of, ooh, that light bulb didn't work that because of potentially this or that, and you keep trying 500 times until Edison didn't invent the light bulb, right?

So, but that's the story that goes, and so how you fail and what you can bring to the table in knowledge of, you know, , never be the person that only brings problems, bring a problem, and, a potential solution. Hey boss, I'm really struggling with this, blah, blah, blah. Here's what I've tried.

I've tried X, Y, and Z, and I can't seem to make it work. Do you have any [00:51:00] feedback? Do you have any direction that you can give me? If an employee comes to me and says that they are my new best friend, right? I had a, one of the smartest, no, one of the smartest, one of the best employees I ever had, is his first job at Mitre.

And, he would come to me with these really silly questions and I didn't know the answer to them, but I would type it into the old Google machine and that first result was the answer he was looking for. He kept coming to me, kept coming to me, and he kept coming to me. And I got, I started to get kind of pissed off, and I was like, dude, what are you doing?

He goes, well, I just didn't know the answer. And I told him this. I said, the next time you come in my office and you ask me a question, if the first result in the Google machine is the answer, you're in trouble. Right? And what that gave him was confidence to figure things out on his own. He was terrified of making a mistake. Like, dude, [00:52:00] come to me and say, Hey, here's my problem. I've googled this, this is what I've tried. Do you have an alternative that I might should be, that, that might direct me in a better way? That's a great question that every boss will appreciate, you know? And if they don't, that just means that they're a bad boss.

You know? And now you're just gonna learn from a bad boss. When I'm in leadership, I'm not gonna do this. My parents did this to me in chess games. Well, when my kid plays chess, I'm gonna say, you know what, that's amazing. You know, and they say this, don't say, good job. I just learned this.

They say, don't say, wow, you did a really good job. Say, wow, I can see the effort that you put in and that switching of phrases makes it from. Oh, I'm good at this, versus I work hard and this is the result. Right. And it changes the mindset and it's fascinating.

Ryan: Yep. Totally.

Totally. And that's the basis of the, of that book mindset that we were talking about.

And [00:53:00] still to this day, it's a very difficult habit to break. I have a friend who's very successful. He's a process engineer at a very large public company and, he, I was texting him and I was like, Hey, did you see this, whatever is a game, or I forget what it was. I was like, did you get into that?

And he's like, nah, I don't do things I'm not good at. And like, like that was literally his thing. And, you know, we were raised together and I totally understand. That mindset still, like he's still not willing, even though the stakes are super, like it's a social thing, right? Like, he's still not willing to break that frame and go outside of it because he was discouraged from doing things that he wasn't good at for so long.

Jason: So, When I was, so I was in the Marine Corps and I got on the Marine Corps, and I knew that I wanted to be, a movie director.

And at the time I was doing some, like, lighting in high school, and I kind of started to get like little pickup jobs in DC in Chicago, doing some lighting stuff but I knew that I couldn't make the leap from being a [00:54:00] lighting guy to being a director. Like, that's just not a through line. And so I was working at Mailbox, et cetera, before I was homeless.

This is when I was working there. This lady came in, and we got chatting, and I was like, oh, I'm new here. Oh, what are you doing? Oh, I'm, I'm in theater. And she goes, oh, I'm in theater too. I was like, oh, cool. She goes, well, hey, I'm about to start rehearsals, for this play that I'm directing.

What do you do? You know, what do you do in theater? And in that moment, in that half second, I didn't say, oh, I do lighting. I said, oh, I'm a stage manager. She was like, oh, I need a stage manager. And I said, cool. Cause I knew that you can get from stage management to directing, right? But you can't get from lighting.

So in that half a second, I was like, oh, I'm a stage manager. Have I ever stage managed anything? No. Did I know what stage management was? Not really. So what did I do getting to your friend, right? What did I do? I bought a book 'cause you could learn anything from a book and the book was called [00:55:00] Stage Management and when first rehearsal, I read the chapter on first rehearsal.

I love that chapter. You know, like, whatever and I read that chapter the night before and I did the things in the book and and I literally did. That's, I just literally, that's what I did. And I was like, oh. And it's like, here's how you mark up a script for cues and stuff, and oh, here's what you, how you blah, blah, blah.

And oh, tech rehearsal. I read the fucking chapter on tech rehearsals, like in a, opening night and blah, blah, blah. Closing night. I read that book. Just in time, just in time learning. And what had happened was, at the end of that play, she came up to me, she goes, you're the best stage manager I ever had.

And I was like, I was confused. I was like, well, I've never done it before. She goes, you, I've never, I have never had anybody do a script analysis for me and blah, blah, blah. And I was like, that's just what the book said to do. So I just did the, Nope, we don't actually do this. And he goes, no, nobody does that , [00:56:00] but I did.

And so it just got me a reputation in the Chicago who was like, this guy's an amazing stage manager. And so I started stage managing and it's just like, that's, I was like, in the moment, I was like, I'm terrified. I'm terrified. When I read a book and I read the chapter and I went in and I did a good and authentic job.

And, I got good at it. You get a reputation for being good and it elevates and it elevates and, but yeah, it's just, it's a, it's an idea of that, you can not do a thing cuz you're not good at it, but how can you be good at it if you haven't done the thing?

And so, you know.

Ryan: One of the things that people really struggle with, and I'll call myself out here, I struggle. All of the things that I say that people struggle with, I really just talking about myself. They're my own insecurities coming out and like, one of the things was that whenever I get hired for a new role, and not, I'm an entrepreneur now, so I don't really get hired.

But even when I do things in my own business that I've never done [00:57:00] before, like I'm taking business meetings, which is actually even a little bit more, I have nobody to fall back on, right? And so there's a little bit more pressure. I always feel this huge imposter syndrome. Like here I am. Like I, I wouldn't have been able to do what you did.

Like I wouldn't have been able to say I'm a stage manager and then, by a freaking book and then, and then do it. Because I would just, even though I feel like maybe I could have, I could have done it, but, I would just feel like too much of an imposter to do that. Sure. Like how do you get over that?

Jason: You don't? I think that imposter syndrome is so healthy. It keeps you moving forward, it keeps you engaged, it keeps you learning. And the truth is, if you are at a table and you feel very comfortable, you're probably at the wrong table because you might be stagnant, you know? am I good at my job?

Yeah. I'm pretty darn good at my job. Am I in rooms? And I know[00:58:00] act and perform in that room. Of course I do but do I look across the table and I'm like, wow, that person is so accomplished. Wow, that person is so smarter, so much more smarter than me while that person has been doing it far longer.

Oh my god, that person has a PhD in cybersecurity and here I am. Having never gone to school for that, but hey, I've got some nice cert certifications. Imposter syndrome just tells you that you're in the right room and is used as a tool. One of the things that I love is this idea of saunder.

Saunder is this word that doesn't really exist, but it was defined in this book, and it just simply says that everybody is living an equally complex life as you and if you can take saunder, that means that I can look across the table at you, Ryan, and I can look across the table at my boss or whomever.

And I can say, wow, what's going on behind their eyes? How terrified are they? What imposter syndrome do they have? Oh, wait, that person, the cto, [00:59:00] they don't have imposter syndrome. That, and imposter syndrome just tells you that you're in the right spot.

Ryan: Yeah, definitely. And it's definitely something that with so many people that listen to this podcast, they're transitioning from one industry into a completely different industry.

And they're gonna feel that within, hopefully the next couple of weeks, they're applying to jobs. Hopefully the next couple of months they land it and you're gonna be sitting in this new role, kind of just like you at Meder, right? Like you went from Chicago. One literally on Friday, and then on the next day you're in DC and you're working on an NLE and you're just like, I have no freaking clue why I'm here. It's when people are experiencing it, just know that it's normal and that like, you're not alone. Like, and for the most part, it's, and most organizations, people are sympathetic to that, right.

Like, or, or even empathetic to that. Like they, they've all been there [01:00:00] and as long as you're coming, kind of backtracking to what you said, which as long as you're coming to them with, good questions and caring. You're, they're gonna help you out, right? And I think that questions, things that you were talking about is so important.

Not necessarily just in a leadership type of capacity when you're going to your leaders, but also when you're doing outreach or when you're trying to get help from somebody. , like we get a lot of, we get a lot of inbound and we encourage it. People hit us up, comment , email us, whatever we're available.

But a lot of it is, Hey, I want to get into tech. How do I do it right? And it's just like, Dude, you know, not to, beat anybody up cuz I was there but like, we put out a weekly podcast. We've got 70 plus episodes now, hours and hours, our TikTok is full. You know, we, I do this full time.

Like, there's a lot of stuff that in there, but when people are like, Hey, look, here's the context [01:01:00] behind what I do. I'm an older worker. I used to be a teacher. I'm looking to, I want to get, I wanna stop dealing with kids, da da da. Here's the things that I've done. Okay, now I can talk to you.

You know, we can have like a more conversation in there.

Jason: Yeah, I get asked a lot, actually in, in TikTok messages, either in a TikTok that I've made, which I don't really do so much anymore, but , at one time I did. Or just in, like in your channel where I commented about, you know, what I do and what I make and that I don't have a college degree.

I think that one of the things that most people are afraid to do is change. One, change is terrifying but when you look at change or you look at a new industry, I wanna get into tech. Well, that's a big word, right? I wanna get into shoe sales. Oh, you know what I mean? Like, you can't solve that is an unsolvable problem.

One of the, one of the favorite quotes, I, I give a lot of lectures at conferences and stuff, and one of my favorite quotes [01:02:00] is, By a guy named George Polya. He's a 1945 Hungarian mathematician. He wrote a book called How to Solve It. I call it the greatest cybersecurity book that was ever written.

Obviously it's not about cybersecurity. 1944. It's published in 1945. it is a book on how to teach, mathematics to teachers. So teaching people how to teach mathematics. And in that book, he has this quote that says, if there's a problem too big to solve, there is a smaller problem you can solve.

Find it, you know, and it's about decomposition. It's about bringing a problem down to its simplest forms because I can solve a small problem. I can't solve how to get into tech, but I can. What certifications should I be looking for? What soft skills do I have? Is this your first job? No. So do you know how to write a report?

Do you know how to, I don't know, lead children into a class [01:03:00] have recess, where, guess what? You now know how to herd cats. And a thing that a good leader and manager should know how to do is herd cats, right? How to deal with egos in the room, how to deal with the temper tantrum, how to deal. Calm, rational thinking, how to put a plan together.

Teachers are really great at plans. Well, guess what? Maybe getting into tech means that you get your certification in Salesforce, right? Maybe you get your certification in whatever, because it's about leading and about organizing. Getting into tech doesn't mean that you're a programmer. Getting into cybersecurity does not mean that you're a hacker, right?

I go to MBA students and I say, Hey, do you wanna get into cybersecurity? They're like, no, I got an MBA. I'm like, that means that you're a good business manager. Cybersecurity is about business risk. Guess what? You know, you know business. Now all you have to know is this little bit of technology. So now all you have to learn is this, cuz your soft skills surround cybersecurity.

Now all [01:04:00] you have to do is read X-Men for a couple of months and you'll know the right technical terms, right? You're like, oh, I could never get into tech. I could never get into cyber security. Cybersecurity is, there are far more people that work in cybersecurity whose fingers never touch the hacker keyboard, right?

The system. I've never been a system administrator in my life. I couldn't find my way around a CLI if I wanted to command line interface, could never do it right? But I hire people that can hire your weakness, know what you're good at, know what you're not good at, and then hire people that are good at the thing that you're bad at, and then teach them what you're good at and hopefully you can absorb some of the things that they're good at.

Congratulations. You're now a good leader.

Ryan: Totally. Totally. One of the things that the, with Hannah's story, the way that she got into tech was that she got a Salesforce administrative certificate and, then she went from the call center unemployed 30 days later getting the admin certificate and then getting a job.

And [01:05:00] she could barely turn on a computer. She can still, she's still terrible. She, but that's not her job, right? Like, I mean, she was an admin for a little while and she got the cert so that people could, okay, you got the cert. Perfect. That's what we need. But exactly what you said, the surrounding soft skills she used, she used the cert to get her foot in the door, and then she went into places where she was strong and now she's in a great place.

Yep. Where she's doing everything that she's, good at and she doesn't have to do anything she's bad at, you know? For the most part.

Jason: What I can, what I wanna give everybody confidence in is, there comes a point in your career where people don't give a shit what your college degree was like now.

Yeah. If you went to Harvard or something. Yeah, sure. It looks really good, but like, man, I have never, like, have I not gotten jobs because I didn't have college degree on my resume? Absolutely, [01:06:00] absolutely. Could that college degree have been in basket weaving? Absolutely. Absolutely right. Masters in nobody cares, right?

College degree masters or whatever that nobody cares. They just care that you've got this little thing now it weeds you out of a bunch of jobs, but like maybe, and it is frustrating like I did when I finally started applying for jobs. I was very fortunate that you can kind of tell a lot of my jobs, in fact, including the one that I got very first in cybersecurity, I got from friends.

That were doing a thing that I didn't know what they did in life. I didn't know what their job was. They were just a friend. I was playing video games with Yak, a guy named Jay Crosser. I was, playing War Hammer 40k,, the little figurines at the games workshop, with a guy named Lynn, Leonard, and we were playing for War Hammer 40k.

And he was like, oh, I work at Mitre. He goes, oh. And he was like doing some stuff and and he goes, Hey. [01:07:00] So it's a long, it's a weirder story, but I'll truncate it. I was about to hike the app, Appalachian Trail, after I, I left Mitre, worked on an organic livestock farm because I got curious about farming.

So I left this job that was paying me $110,000 a year to be, to make $9 and 75 cents, an hour as an intern, at an organic livestock farm because, Why not? So I did and anyway, I did that for a year, almost a year. I was about to hike the Appalachian Trail went in, my buddy Leonard, Lynn, was like, Hey, blah, blah, blah.

When did this company, they were doing this conference and they were like, oh, you used to work in theater. Can you help us, like jazz up some of these scripts? Cause they're doing like this role play kind of thing. And I was like, yeah, sure. Went in, did the thing. And I walked away. They paid me for a couple of hours, 500 bucks.

I was like, sweet, thanks. And I left and Lynn called me up and he goes, dude, you blew everybody's socks off. Can we hire you? And I'm like, one, I don't [01:08:00] work in cyber security. Two, I'm about to hike the Appalachian Trail and three. No, like, no. And he was like, oh, just can you come back in for another session?

I was like, dude, you're paying me. I'll come back in. And it was like five days before I was gonna hike. Like I'm in a, like in a hotel with my backpack. Like I, my stuff is in storage, like I'm hiking the Appalachian Trail and like three days too, when I was like, I'm leaving like in two days. And they put a fucking offer down and I was like, damnit, I guess I work in cyber security now and that is the day.

And I wasn't joking earlier. I went home and I opened up a computer and I was like, what is cybersecurity? And what I found out is that all of my previous jobs going all the way back to, the military into theater and into working at a., which is my own fault. Doing this, doing that, working at Oprah, working at [01:09:00] Miter, it brought me this enormous amount of soft skills that I could walk in.

And again, all I had to do was read X-Men for a little while and figure it out, and then trust that I had a team of five people that I was now leading who have been working in cybersecurity and information technology. Entire decades, and I'm now leading them. So what did I do? I asked intelligent questions.

I didn't pretend to know it all. I was not the smartest person in the room and I leaned on the strengths of the people around me, cuz that's what a good leader does. And so, yeah, I googled what is cybersecurity, but if, if you learn how to learn, then it's not that daunting, you know? And when I inevitably got fired from that job, which is a funny story, which we won't tell, but, It got fired for the all the right reasons, which is okay.

It is okay in life if you get fired for the right reasons but I [01:10:00] found myself, I got this cybersecurity job because I didn't apply for this job, right? But I now in a position where I have start applying for jobs. I don't have a college degree and I have no certifications to my name. And so I went and I studied just, like you said, I studied for 30 days.

I was unemployed. I had nothing better to do. So I got the big book on the CISSP, you know, chapter one, read it, chapter two. And I read it. I learned about encryption and all these things and I knew the words at that point. Cause I'd worked at this company for a couple of years, so I knew some of the words, but I didn't know how to apply the words.

And so I studied eight hours a day cause I'm terrified at this point that I have to now, you know, one of the worst things that you can do in life. Is make money. When I was an artist living in Chicago, I was making no money. I was barely paying my rent, and I was the happiest I'd ever been.[01:11:00]

But then you get a little taste, you start working for Oprah and you start making some money and you go to DC and you really start making some money. And now it's like, well, fuck, can I go back to not making any money? And, I always say that like one of the worst things you can do in life is start to make money.

It's fascinating the way that works but anyway, so I studied really hard and, I went in and their pass rate of the CISSP for the first time is like 30%. 30% of people, 70% of the people fail it. I studied, I was very fortunate. I passed it the first time. I then got my second certification called the CRISC

I have this out because one of my teammates, one of my employees, is going after certifications and we were chatting this morning in our one on one and I was like, C risk, C R I S C, which is certified in risk and information systems control. So I have a couple of other like, There's only two certifications I have.

I have a couple of certificates on like cloud security and [01:12:00] insider threat and some other things but those are the only two certifications that I have and honestly the only two certifications that I would probably ever have, cuz they're, that's all I need, you know? So, but yeah. And I started applying for jobs and I had that CISP on my resume and you start getting calls.

Ryan: With the certifications. That's one of the things, like it's how we first got connected through, the, our series that we're doing on tech certifications that can make you more than a master's degree. Yep. And we've kind of talked about offline about it and like, We are very glad that the message is getting out there, but I think what a lot of people think is that the certifications are like a silver bullet and like once you get it, you're gonna, you're gonna get the job.

And as we were talking, it's a little difficult to add a bunch of context in 15 seconds or one minute of a video, which is why we do this podcast. So we can add a little bit more context behind it but for those people that are just looking to get into, tech search for IT specifically

From [01:13:00] what I understand, I think the CISSP. That one you need experience behind it.

Jason: Yeah. You have to have a, so to get your CISSP, you have to have a sponsor and that pers, that sponsor has to have the CISSP.. Then you have to have x number of years of experience, like five years of experience.

Now you can still get the CISSP.. If you have a sponsor but you don't have the experience, they just kind of put you in this like temporary, I don't know what they call it. The CISSP the way that it's described is that's like master's school. Like you go to master's, for your master's degree is like getting at the end of that master's degree in cybersecurity, you'll be able to take the CISSP and pass.

That's how they kind of conversate it. Other things like there's smaller certifications. You know, people, a lot of ways that people always start is, I always forget 'em because I don't, I don't work with them very often, but the information security professional or the, oh, I should have been prepared for that, but there's a lot of really smaller certifications that you can study for the weekend and get.

There's [01:14:00] one on information systems and there's one on, on information security and you can start with those. Those, if I see that on our resume, or your Ethical cert, your ethical Hacker certification, which is one a lot of people get, if I see those on the resume, like that's entry level, like you are getting an entry level job, which by the way is not a bad thing, right?

But it is so important for people to know that you do not have to know computers. You don't know how to, you don't need to know how to be a hacker to work in cybersecurity. My sister-in-law, she is about my age and she's a a database administrator, a dba. She works for a bank. , well, part of her job is working as database administrators, making databases, but also taking that data and making queries out of it and doing BI tools, so business intelligence, so like dashboards and stuff like that for this data.

And so she and I were talking [01:15:00] last July 4th, so we, a year and a bit ago and she was like, Man, I'm just really bored. She goes, you know, and I was like, well get into cybersecurity. And she goes, I could never. And I'm like, are you kidding me? You're a database engineer. Yeah. What do you do? Well, I just make really complex queries and I make dashboards and I'm like, let me introduce you to the world of a sim system.

Something. It's this where you get all this, all your logs and all your data, and then like for me, This television, and it's like when that red light goes on, I have to like, something bad is happening. Well, that's a dashboard and all these logs are going into this sim system. And then you have to, I can't make sense of that.

That's just rows of stuff, but she can go in and she can make a really smart query that then every time that red light's going on, it's because she made the dashboard. That dashboard, that light, says that if someone opens a computer simultaneously in the United States and in China, well that can't [01:16:00] happen, right?

So that means that person probably just got hacked, right? That laptop, that employee. And she made that dashboard and she walked in and there's literally a spreadsheet, the little PDF that says, Splunk, which is the software Splunk which is not great, but Splunk is what everybody uses. Splunk for database, database administrators.

So it literally was, Splunk was like, here's education material. If you're coming into a sim as a database administrator, there's literally a manual. She looked at it, she looked at it and she was like, oh yeah, okay, I can do this and boom, she's now working in cybersecurity.

Ryan: Amazing. Amazing. And that's just like, it's very similar, or at least I will make the connection I suppose, to your story of going from like Oprah and being a Marine and having these three different, skills that Mitre needed.

Where you can make a connection and then go work on, Les [01:17:00] for a DARPA funded project, right? So like these intersection of skills, if you can hone in on that, if you can say like, okay, I'm not in cybersecurity, but what I can do is I can dress up this data and make it actionable for somebody that is a decision maker.

And it's like, yeah, cybersecurity absolutely needs that, but logistics, tech, operations, literally every industry needs that same thing. And if you can find those places where your skills intersect, you can make a career for yourself or at least a starting point in that career.

Jason: Yeah, and I think it's one of those things like you're not gonna know what that intersection is until you get into it but what I can promise everybody is that soft skills. I will hire somebody for their soft skills way before I hire a really smart person in that very specific thing that I need because that means they can only do that very specific thing. I can teach that somebody can teach [01:18:00] that, that can be learned.

But what can't be learned is how to lead a team. Well, you can learn that, but what I mean. How to go into a room and have conversations and like there's soft skills around. Life, right? Organization. Well, I'm a stay-at-home mom. Well, I'm sure there's a thousand things that you're probably good at, because you're a stay-at-home mom.

And by the way, stay-at-home moms can make a great living in tech for using and again, I think the Salesforce thing is such a popular one. Cause it's pretty easy to get like, as far as like the barrier for entry but like you're, you can walk into a $70,000-$80,000 job. I don't know. I've never hired one, but like you can make good money.

Right? And this is the thing, and I'll just tell really on money. So first of all, I'm the director of information security. I make $175,000 a year. My total comp, which is very the thing that we say here in the Pacific Northwest cause it takes in like your shares for the company as in bonuses and all that.

So buy up 225,000, but 175 is like the take home. When I [01:19:00] got into cybersecurity. I was working at that company where I just started then the next company where I get the certification, this other company called kw, they're not around anymore. It's a consultant firm. I walked into that interview, got the job, kinda like right then and there they hired me and then they paid me like $115,000.

Right. , I was really happy with that. I didn't have a college degree. I'm pretty happy with $150,000. Cool and I left that job and they took me aside, and I'll never forget this. He took me aside and he goes, Hey man, you know why we hired you so fast? And I was like, cause I'm awesome. He's like, well, other than that,

So other than that, it's because you underbid. Everybody else that was coming in this room was saying their salary requirements were 135, 145, 150,, and we would've paid it but you walked in and said 110, or you know, whatever, which is lower than I was making because I didn't have confidence. I only had this one certification and I had a huge amount of imposter syndrome.

And so he goes, [01:20:00] we hired you because you're the cheapest. And by the way, yeah, you're awesome. So he goes, I'm telling you this, so that you can correct it. And so from that job, the way that you make more money is you don't stay at a job, right? You move jobs, which is a known thing. Everybody accepts it, it's totally fine, do it.

And I went from making that 110 to making the most I ever made in life was $190,000, two jobs ago but they overpaid me and I knew they were overpaying me. It's fine, but you go from one job. So I went from that to a hundred and thirty, a hundred thirty five, whatever, to the next job was 150, 155 whatever it was.

Then I think there was another job that was 155, then 190, then I went down to 155 again, working at my last job and this job is now 175. So also don't have the hubris of be like, wow, I was making $190,000. I went from making 190 to making 155 cuz that was actually fair market value for the role that I was in.

I wasn't a [01:21:00] director at that point but the 190 I was a vp, which kinda makes sense, but then I went down to 1 55. So don't, don't have the hubris to be like, oh, I'm making this, I'm gonna make this for the rest of your life. No, man, you want a job? There's $155,000 a good life living. Heck yeah. Take the job.

Don't be like snobby about it. And then I left that job. Got fired. I got fired from a lot of jobs and I, it's fine. It's totally fine. I'm fine with it and, you know, part of part of having ADHD and being autistic is, is sometimes you don't say the right things. In the right rooms. You say the wrong things in the wrong rooms and people don't like it so.

Ryan: I think that's an important point. Oh, as far as the, don't be afraid to take, make less money and that's one of the things that we see, a lot in people that are especially transitioning because they've worked their sa, they've worked their way up in one industry, and they're a middle manager in, whatever, you know, let's just say they're [01:22:00] a store manager at a small retail company and they're making, $110,000 but it's brutal, other than the owner, they don't have a boss. It's like 80 hours a week and they're like, well, I have to go do something else, but I don't wanna take a pay cut. It's like, it's give and take man. You know, like what about just taking a pay cut for just a little bit while you get, you know, get your feet under you and then transition into a new field?

Jason: Yeah. So you bring up a good point. Right. And it's important that as we have conversations about, maybe as I tell my story, right? It, you have to recognize that switching jobs when you have a family, when you have kids, unlike me, you know, there I don't have kids and so you have to recognize the privilege that you have, that maybe a lot of people don't have.

They don't have that privilege and so when you're talking about taking a pay cut, yeah, look, you can takea 10 or you know what I mean? A 15,000, maybe even a [01:23:00] 20,000 pay cut if you're already making 110. Right? But you can't ask somebody making 65 to then make, you know, 45. Well, that's poverty level, you know, especially if you have children.

And so there's privilege with being able to be flexible, but you can do both at the same time. Right? You can have the job that you know, never look for a job when you don't need a job or when you need a job. You know, always look for a job when you don't need a job and because you can be picky. So get your certification and then find out what the market's like, or find out what the market's like before you get the certification.

Hit someone up on LinkedIn. The thing that this, the thing that people don't realize, maybe they do, is that. Why am I on this podcast? Right? Well, I'm on this podcast cause yeah, I think I've got a story to tell, but I also like to teach and everybody likes to tell their story. And even if that story is how they do their day to day life.

And so you can make bosses [01:24:00] into Champions because people want to help smart and capable people. You don't already have to be awesome at the thing. You have to though Google the first line and say, oh, this is boss. This is what I've done to try to solve this problem. Is there, same thing with, mentors, hit someone up and ask intelligent questions.

How do I get into tech? I don't know, dude, I can't help you. Hey, I'm looking at getting into cybersecurity, but I've got an mba. And I've looked around and I think that maybe I can, I'm really good at risk and understanding risk. What do you think the good place to start is? I don't know. Hired immediately.

You know, so ask intelligent questions. Do a little bit of research so that never say, Hey, can I take you out for coffee and pick your brain? Nobody likes that. Nobody likes that. So that's dead in the water. But if you say, Hey, I saw your resume. You have X, Y, and Z. I'm trying to do one, two, and three. I think I could [01:25:00] learn a lot from you.

Can I have a 15 minute Zoom call with you if I see that? I would probably say yes. Awesome.

Ryan: Amazing. Jason, I don't wanna take up, all of your day. , my last question is if people wanna learn more about you and say hi, where's the best place that I can send them?

Jason: Well, LinkedIn, so you know, Jason Tugman pretty easy.

LinkedIn is always good. I have a website. If you wanna read really dry articles on cyber risk, you can go to Super fascinating. I promise you , or you can hit me up on the old, tiktok machine. I think my name is Saunder LFe I I think maybe you might know better than I.

Ryan: Yeah, I will put least everything in our show notes for everybody.

Yeah. But yeah, Jason, thank you so much. I actually still have like a whole page of notes, of things that I wanted to ask you. , so maybe we could do around two sometime.

Jason: Hey, look, if you wanna have me back, you know me, [01:26:00] man, , I'll always talk about myself. I'm sure I have more stories to tell.

Ryan: Yeah. Thank you so much for the time, Jason.

Jason: Absolutely. Thanks for having me. I really appreciate it.

Ryan: Thank you so much for listening. Before you take off, if you haven't already, please subscribe to our newsletter, It has everything from Degree Free Jobs and how to get hired without a college degree.

If you want the show notes to everything that we talked about, is where you can go to get the links for everything that we talked about. Until next time, guys.



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