Breaking into Cybersecurity - Mike Lossmann

Christophe Foulon: 00:00:27

Welcome to another episode of breaking into cybersecurity,

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where we talk to individuals who have

broken into the field so that they could

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share the tips and tricks of their journey

to help inspire the next generation.

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If you're listening to this show, feel

free to share it after the fact with

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any friends and family that might be

interested in joining the field, because

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we need that diverse perspective.

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In order to tackle the problems of

future generations today, we have

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Mike Lossmann, who's coming from us

from a very interesting background.

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And the reason I say that is

having talked to him before.

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I know we have quite a story in, in, we

have quite a story in tune for you today.

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Mike, do you want to give us a little?

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Mike, do you want to give us a

little background about yourself?

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Mike Lossman: Sure.

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Good morning.

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Good afternoon.

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Good evening.

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Everyone who's listening.

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As Chris said, my name is Mike Lawson.

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I am currently a technical product

marketing manager with forward networks.

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You guys don't know who

forward networks is.

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Think of what we do is we create a digital

twin of your network infrastructure,

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and it allows you to be able to get

insights from your network that you

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were never able to get before and

reduce mean time to recovery and

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meantime to insights dramatically.

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Prior to forward, this is where

the buckle up part comes in.

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I have been all over the place, so

I was a senior network architect.

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For a bunch of fortune one fifties,

one that I'll name drop is the

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Coca Cola company from Coke.

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I went into sales.

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So I was a senior sales engineer

at both person networks and

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Nokia focusing on their S.

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D.

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Wann product line from there.

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Being in sales wasn't crazy enough.

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So I decided to go into consulting.

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So I was a tech consulting manager at

Ernest and Young, where I focused on

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a digital transformation, specifically

SD WAN and helping organizations

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on their zero trust journey and

completely switched careers and

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decided to get into, to marketing.

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Wow.

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Christophe Foulon: Let's

take a step way, way back.

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What got you interested into

tech and security or any of it?

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Mike Lossman: So I've always been

the type of person to tinker with

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something ever since I can remember.

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I remember my mom telling me stories of,

so I'm like originally from New York.

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I don't know what McDonald's looked

like in other parts of the U.

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S.

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But.

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When I was a child, they had this big

metal grimace that looked like a kid

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jail, and it would rock back and forth,

and instead of being in the kid jail

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rocking back and forth, I was under

it trying to figure out how the spring

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worked, how everything actuated when

I was six or seven, I decided to put

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a sign up on our front door saying

that I could fix your electronics

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and just Progressed from there.

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I've always been, like interested in

everything, like technology related.

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And it wasn't back when

I got into the field.

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In early 2000 it was

really hard to get into it.

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To the point where, people were telling me

we don't hire people without experience.

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You need college degree.

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So I went out.

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And did the college thing came back.

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Oh, now I'm overqualified because I have

a master's in in in network security.

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So now it's like, all right, I did all

this because you told me to get a degree.

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Granted, when I do things,

I do, I like do things big.

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I just don't go.

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Oh, bachelors.

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I'll stop.

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I just always go for that next level and

then decided to take the certification

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road, hide my master's degree on my

resume, and wound up probably finishing

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with well over 42 certifications.

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That's not a lot.

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no.

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It's easy weekends worth of work, right?

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So

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Christophe Foulon: if you

weren't overqualified with a

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master's, what did they tell you?

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Mike Lossman: 42 certifications

was over the span before I

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got into the sales world.

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Until I got to Nokia where I did

a couple of certifications there.

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So I started off small, right?

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So I.

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In the enterprise world, I just didn't

walk into a shop and go, Hey, I'm a

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network guy or I'm a security guy.

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This is, what I want to do.

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I started at the ground, so I walked

in, actually, I started at Best

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Buy as a in store tech supervisor

before the geek squad took them over

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when the geek squad took them over.

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I used to be.

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A big dude and they wanted me at 300

plus pounds to fit in that little VW bug.

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And I laughed at them and

said, that's not happening.

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So started out at Best Buy, went

into PC tech roles at several

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law firms where I was exposed to

different parts of the infrastructure.

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So I was exposed to security.

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I was exposed to.

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Server work.

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I was exposed to the system side.

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I was exposed to networking.

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I gravitated towards the networking.

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Security was interesting,

at least in security back in

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like the early 2000s, right?

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We're talking about ideas.

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We're talking about firewalls.

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We're not talking about some of the stuff

that we have to do today with identity and

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advanced segmentation and stuff like that.

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And then yeah.

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Tested as I moved up, working in

working in different areas until I

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found that niche and networking where

a lot of the networking roles I had.

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Were dual split, so it's like

security would set the policy.

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And then we would apply

the policy on the device.

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So the security guys, like we shared

responsibility of a lot of the security

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devices that we were actually playing

around with and a lot of things you

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don't see is you don't see a lot

of network guys and security guys

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seeing eye to eye on a lot of things.

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It was my goal to make sure that any

security guy I spoke to, him and I, or

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her and I had that mutual understanding

that listen, I'm not here to, step on you.

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I would hope you're

not here to step on me.

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Let's try to work together because

at the end of the day, we have

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1 goal and that's to make sure

that our resources are secure.

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And it's not a contest to see, Oh,

because I'm in this part of the

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infrastructure and you're just some packet

jockey, it's like working together.

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And I've always taken that stance

everywhere I've been, and I think that's

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part of the key to at least the success

that I had is don't let your ego overrule.

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Or don't let your ego get in

the way of what other people are

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there to help you with or to help

you get through your daily job.

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That's

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Christophe Foulon: that's so true.

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I think that's one of the things that

I've also tried to do is I go in with

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a coaching approach where we're having

a conversation and we're there to find

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Best mutual solution for that's it what

we're trying to achieve versus one person

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being right and the other one being

wrong and that's it's a zero sum game

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Mike Lossman: It's one of those things

where it's you can be the loudest person

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in like the conference room What's

that going to do for the issue that

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you guys are working on, or the issue

that you guys are troubleshooting,

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you're allowed the security guys loud.

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The infrastructure guys loud.

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You're just going to argue with each

other for hours over who's right.

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Just come to that commonality.

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And figure it out together.

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Christophe Foulon: You're network focused

and you understand that the perspectives

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of security and then why sales?

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Mike Lossman: So one funny thing about

me that very few people know, and a lot

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of people are going to know after today.

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When I was in the enterprise world, so

when I was with, we'll just pick out Coke.

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I was the guy sitting in the corner.

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Just taking notes, nodding my

head, not really saying anything.

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I had always wanted to go into the

sales world because in my mind, I

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had pinnacles set up of my career.

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Coke was the pinnacle of

the enterprise career.

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It's you can't get at

least in like my mind.

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A lot of people may argue with me.

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You can't beat a company where they're

local, sorry, where their logo is

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recognized in every country in the world.

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To me.

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That's the pinnacle.

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I always wanted to get into sales

because I was getting bored.

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Playing around one like infrastructure.

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So it's Hey, let me go into sales.

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The SD Wan world is a amalgamation

of networking and security.

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So let's see what I can

get into in sales versa.

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Versa picked me up from coke.

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Did a lot of cool things with

them, saw Adversa was able to

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help a lot of organizations.

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On their SD when journey when SD

when was still new in people's

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minds, but it was always I've

never been someone to hoard data

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especially if it's a on call rotation.

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And if someone below a tier 2

or a tier 3 guy can do the work.

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I never held anything back.

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It's like you want to learn.

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I'll teach you whatever you want to learn.

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And I think moving from enterprise to

sales afforded that opportunity with

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a little extra stress on the back end

because there's numbers and all that

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other stuff you have to worry about.

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That really wasn't forefront in my head

when I was thinking about doing it.

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But yeah, it's that knowledge

share and being able to talk about

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technology That I'm passionate about

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Christophe Foulon: many people

wouldn't see that as a logical move.

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What were the, what was the

value add in your mind of

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doing this now after the fact?

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Mike Lossman: So now seeing how my

career has laid out, ultimately it was a

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building block to get to where I am today.

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I always had in the back of my

mind, once I got into sales, I

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wanted to do something with, like

technical marketing or consulting.

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It was 1 of those either or type of

things with me and when I went into

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sales and I got that experience, right?

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You're only to me.

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It's, if you're in 1 company,

you're only bound by what that

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1 company wants to do, which.

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Mayor, which like may or

may not be good to me.

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It's wanting to learn everything.

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I could learn moving into sales Starting

to build how to talk to people One of the

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funny stories that I'll share is one of

the first presentations I did it at versa

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was actually to my account manager and Se

number one because they were still a new

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startup when I had joined in 2017 and I'll

never forget my Who the guy who turned

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out to be my account manager sat down with

me after the fact and he looked at me and

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he's Mike, I don't know why we hired you.

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He's you really can't

present to save your life.

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I don't know why you're here.

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I don't know.

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I don't know who you duped to get here.

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He's you were constantly saying

some words under your breath.

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You should have been saying.

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You had some really awkward pauses

during your presentation and you

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loved using the word he's in a

minute span, I counted 77 ums.

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I'm like, oh, all that's a good way to

beat somebody down and let them know

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that they made a wise career move.

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But then with, practice, I honed it.

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And then that kind of that's

that, what led me into Nokia.

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THey came along and they were like,

Hey, listen, we want to take you.

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You're an enterprise guy.

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Similar to what Versa did where

it's I'm, I'm, relatable to the

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network person or like the security

person who's buying the product.

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Let's put you in another role where

now you've got to talk to CIOs, CEOs,

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monster conglomerate people to get them

to understand why they need to invest

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in our, like platform because their go

to market was through service providers

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where Versa was direct to consumer.

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But now it's an even more

completely different world.

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It was fun.

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There was, there was like a lot

of cool things going on there

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that they were working on, but

something just didn't feel right.

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And it, it turned me off

to the sales experience.

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Me personally, and I was

actually they slid into my dms.

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So I get a probably about 2

years into my stay at Nokia.

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I get a a dm on linkedin from, recruiter

and I'm thinking it's fake, right?

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Why would a big four consulting

company come for a guy who has

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some enterprise experience and

has some sales experience zero?

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Zero consulting experience.

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I could spell it.

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That's probably it.

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I've dealt with them before, but so I

had thought that he had wanted me for E.

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Y.

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internal I.

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T.

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and I was like, no, I don't want to

go back into the enterprise world.

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I've already been there.

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He's no.

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He's we want you for a

tech consulting manager.

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And I'm like, oh, so going from someone

who couldn't present to save his life

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to being a tech consulting manager at E.

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Y.

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Like in a, what was that?

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A four and a half year span.

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Really, opened up my eyes as to

what the future could look like.

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And where my future could go.

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Oddly enough, that was one of the

more harder interviews I've had.

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There was one gentleman who

interviewed me who went like

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really insanely crazy into BGP.

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And I'm somewhat confident in BGP

because of what I've done in the past.

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But yeah, it was just a completely

different animal joined.

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Quickly realized that consulting

is good for a lot of people.

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maybe not someone with

the background that I had.

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I did get to talk a lot about

technology without having to

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worry about the vendor side of it.

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So I could talk about SD WAN for what SD

WAN is, not what a vendor spin on it is.

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I could talk about Zero Trust for what

Zero Trust truly is, and not what, certain

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vendors that play in the Zero Trust space

want you to believe that Zero Trust is.

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So that piece was cool.

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Being able to extrapolate the vendor part.

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And actually talk about what it's

supposed to do was, was really cool,

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had a lot of cool projects there where,

I can't get into too much detail on

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this, but I did work a ransomware

recovery, which led me to have a greater

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appreciation for certain security aspects

for certain aspects of zero trust.

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And then I was doing research for another.

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Client that I was working with and I

stumbled across forward because in my

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head, there was a certain platform that

was used before to do things like this.

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And when I Googled forward was

number 1 in Google, and I'm like,

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oh, this company is interesting.

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Let me see what they're about

and fell in love immediately with

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everything that I saw about them.

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Applied for a different role than

the role I got was told, Hey,

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you're overqualified for this one.

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Sorry.

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And I'm like, Oh, right back

again to right back again to: 2004

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Thanks.

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And fortunately.

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He was like, but, hey, we have this other

role that we think you'd be perfect for,

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which is the role I wound up getting

and taking where I started moving up in

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the enterprise world, messing around in

sales, jumping to consulting to learn that

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piece of it to just rehome presentation

skills, talking skills and all that

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now landing where I am at forward.

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This is the culmination

of an 18 year journey.

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It's not something that

happened, overnight.

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I had a I've talked to a few

people who want to get into cyber

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security and they're looking for.

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The quick way to make a buck and I'm like,

that's the stigma that cyber security

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networking programming, you name the I.

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T.

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Discipline.

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That's the stigma that you get with it.

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But that stigma is false.

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And if you go into, if you go into a

career like this with that stigma, where

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I just want to make pockets of cash and

swim around like Scrooge McDuck, you're

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not going to have a rewarding career.

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I switched.

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I switched.

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Disciplines 3, 4 times in my career,

and, there were some good days where

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I'm like, oh, this is really cool.

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There were some, there were

more bad days where it's oh,

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why did I do this to myself?

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But ultimately, it's what turned me into

what I am today and what I'm able to

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talk about with people, a network guy

being able to talk security, a network

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guy being able to talk infrastructure

and then have commonality with them and

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not be in a conference room and be like,

Oh, I'm the guy who build your road, stop

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throwing, this app on it or hey, security

guy, I don't like, the, I don't, I don't

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like the fact that your vulnerability

scanner makes my router tip over every

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night at two o'clock in the morning.

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So

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Christophe Foulon: I guess one of

the things that I love for more

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junior folks to understand is what

a product marketing person does,

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or even a product manager might do.

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in Their, in the overall ecosystem

and why it's such a critical role.

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Mike Lossman: So a majority of folks

you find in this role are somewhat

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technical, mostly marketing focused,

and they go in, and they, not to speak

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bad of folks who are in this role,

but I've heard some product marketing

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people before who were like, Oh yeah,

my widget does things this way and

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they don't correlate it to anything.

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They don't correlate it to

how it'll make my job easier.

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They try to, and they

flash pretty screens.

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You know what I came into this role

doing and forward has been extremely

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supportive with how I want to do it is

taking my background from consulting,

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from what I've learned in sales, from

what I've learned in the enterprise.

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And making it making everything

seem more accessible to the user.

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So it's my job is to educate the

person who's looking at our platform

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and to show them how it could make

their life a thousand times easier.

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But my philosophy in doing it is I put

myself in situations and situations

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that I've been in before where I

wish I had something like this.

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: 00:19:32

And show you that, hey, this complex

hybrid cloud troubleshooting that you

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: 00:19:37

need to figure out where a firewall

is broken or where something is broken

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that could normally take days to figure

out, depending on how tight you are

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: 00:19:46

with the teams that you're working with.

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: 00:19:48

That you could figure out in less than

a minute and being able to articulate

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: 00:19:52

that, show it and actually give examples

that the security guy, the network

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guy and the infrastructure guy could

actually understand, I think, is what

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: 00:20:01

makes a great tech product manager.

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: 00:20:03

Christophe Foulon: I think that's such

an important skill to be able to have

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: 00:20:08

as to step outside the box and put your

mind in the mindset of the user and

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see what you're experiencing, because

oftentimes it's oh, why did they do this?

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: 00:20:20

Why did they do that?

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: 00:20:22

And put the blame on them

rather than thinking.

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: 00:20:26

Why did they do this?

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: 00:20:28

Did they do this because we were

putting roadblocks in their way

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: 00:20:32

and made it too hard on them?

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: 00:20:34

And they did this because they

needed to get their job done.

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And what could we do to help them complete

their job without them breaking security

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: 00:20:43

policies or breaking security rules?

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: 00:20:45

But let's enable them rather than just

use controls as a way to block them.

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: 00:20:51

Mike Lossman: It's having that

level of empathy to understand,

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even in the enterprise space, right?

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: 00:20:58

If you've moved up, the level of

empathy that you need to have dealing

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: 00:21:03

with a help desk guy who's getting

screamed at nine times out of 10,

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: 00:21:08

anytime someone is calling it to the

help desk, because it's never good.

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: 00:21:12

Excuse me, when something's broke.

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: 00:21:14

They're not going to say, oh,

you do such a great job, John.

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: 00:21:16

By the way, my laptop is on fire.

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: 00:21:19

And I don't know why it's on fire.

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: 00:21:20

We need to figure out why it's on fire.

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: 00:21:22

And I can't get my work done.

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: 00:21:23

And, Bill wants his TPS report tomorrow.

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: 00:21:26

And I can't do it because my

laptop is literally in flames.

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: 00:21:29

Nobody calls the help desk

and says, you know what?

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: 00:21:31

You do a great job.

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: 00:21:32

And I just wanted to let you know that.

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: 00:21:33

Goodbye.

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: 00:21:34

Christophe Foulon: Have you tried

turning it on and off again?

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: 00:21:36

Sorry.

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: 00:21:37

Mike Lossman: Say that.

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: 00:21:38

So the old Microsoft

three finger salute or

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: 00:21:41

Christophe Foulon: there was an old

British show about a help desk and

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: 00:21:45

that's all they did with a recorder.

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: 00:21:48

Mike Lossman: Yup.

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: 00:21:48

Christophe Foulon: So Mike.

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: 00:21:50

You've gone through an illustrious career

what tips would you have for those looking

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: 00:21:57

to break in today and what could they do

to take advantage of some of the changes

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: 00:22:03

in the environment, changes in technology

to hone their craft to get in today?

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: 00:22:11

Mike Lossman: I wish I was starting

now is the amount of data that's

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: 00:22:16

out there that will help you.

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: 00:22:18

That's free is insane.

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: 00:22:20

My recommendation and what I tell a

lot of people is don't because you see,

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: 00:22:26

oh, this guy does all this cool stuff

or this guy does all that cool stuff.

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: 00:22:30

Look at it.

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: 00:22:31

So look a technology as a whole.

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: 00:22:33

Watch some networking videos.

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: 00:22:35

Watch some security videos.

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: 00:22:37

Read some network blogs.

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: 00:22:39

Read some security blogs.

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: 00:22:41

Just try to get a narrowed down

view of what you want to do.

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: 00:22:45

It's okay, so now you want to

get into, we'll just say, we'll

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: 00:22:49

pretty much just say security.

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: 00:22:50

What side of security

do you want to get into?

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: 00:22:53

You want to get into forensic security?

390

: 00:22:54

Do you want to get into data security?

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: 00:22:57

Do you want to get into

infrastructure security?

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: 00:22:59

Then from there, start picking out

topics that you want to learn about.

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: 00:23:04

Use LinkedIn to your like

advantage, find people, connect

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: 00:23:08

with them, ask them questions.

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: 00:23:11

A lot of people on LinkedIn

aren't these big, angry.

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: 00:23:16

People that they may, look like a lot

are willing to help, including me.

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: 00:23:20

If you want to come along, shoot me

a message on LinkedIn, be like, Hey,

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: 00:23:23

I'm looking to break into the field.

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: 00:23:25

I need some advice.

400

: 00:23:27

I would definitely help and be like, Hey,

start with kind of what I just laid out.

401

: 00:23:31

Get a foundation of where you think

you want to be and start learning

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: 00:23:36

about that specific technology stack.

403

: 00:23:40

And maybe you're going to like it.

404

: 00:23:42

Maybe you're not going to

like it, and then you move on.

405

: 00:23:45

Look for roles that'll get

you in the door of a company.

406

: 00:23:49

Help desk role, knock role, sock role,

something that will get you in so you can

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: 00:23:53

now that you know where you want to be.

408

: 00:23:55

Now you're starting to understand

how pieces work together,

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: 00:23:59

how tools work together.

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: 00:24:01

Once you're actually in an organization.

411

: 00:24:04

It's a lot easier to move up and

laterally than it is to if you're not.

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: 00:24:10

So once you get into an org, say

you go into a sock role and you're

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: 00:24:15

like, the security operation

center really isn't for me.

414

: 00:24:18

I thought I'd be, like hunting

down people trying to break into my

415

: 00:24:21

infrastructure and all I am is looking

at these splunk reports and sending

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: 00:24:24

them off to, the the identity guys.

417

: 00:24:27

So then.

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: 00:24:28

You take that you learned, and then

you could, depending on the reputation

419

: 00:24:32

you've built for yourself in that

company, by participating in other

420

: 00:24:37

things by having the willingness to

learn by reaching out to peers, then

421

: 00:24:41

you can start navigating around.

422

: 00:24:44

To see where you want to ultimately

end up, 1 of the 1st law firms I was in

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: 00:24:50

afforded me the opportunity to configure.

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: 00:24:52

Non Cisco guy, non network

guy, part of the PC tech's role

425

: 00:24:57

was to configure switchboards.

426

: 00:24:59

On a Cisco switch, so being able to

branch out like, hey, listen, if you

427

: 00:25:04

need me to do this I'm willing to

learn it and then they can give you,

428

: 00:25:08

completely completely choked down

permissions to just do that, that 1 thing.

429

: 00:25:14

So you can learn and the end is just.

430

: 00:25:17

It's a constant learning environment.

431

: 00:25:19

If you're not in it to at least

learn something new every day,

432

: 00:25:24

then this may or may not be.

433

: 00:25:28

Where you want to be, because looking

at 18 years, let's take that 18 years

434

: 00:25:34

and let's shrink it down to the last 5.

435

: 00:25:36

The.

436

: 00:25:37

The tech world has changed

dramatically in the last 5 years,

437

: 00:25:43

and if you're not willing to learn

and keep up with it, or you have

438

: 00:25:46

that mindset of, oh, you know what?

439

: 00:25:48

I know BGP, or, I know how Palo Alto

does, security and all that stuff.

440

: 00:25:54

I don't need to learn the next

newest thing you're going to find

441

: 00:25:57

yourself sitting in the corner.

442

: 00:25:59

My old iPhone.

443

: 00:26:01

My old iPhone five, wondering

why no one's going to hire you.

444

: 00:26:05

Christophe Foulon: That is very true.

445

: 00:26:06

Mike, thank you for coming on sharing your

tips and tricks and absolutely everyone.

446

: 00:26:14

Thank you.

447

: 00:26:15

And be sure to share this with your

friends and family that might be

448

: 00:26:18

interested in breaking into the industry.

449

: 00:26:20

And again, Mike Lossman,

thank you for joining us.

450

: 00:26:24

Mike Lossman: No worries.

451

: 00:26:24

Thanks again.