It’s the dawg days of summer so here is a podcast to enjoy on the beach, long-drives or at the camp site. It’s that simple folks! In this light hearted giggle, there is a serious reflection we all engage in: where did it all start?
Both Jesse Tuttle and myself are very candid how we owe our technology career success to the Apple II in the 1980s. It changed out lives. It was HOME for two guys that wouldn’t enjoy a day job in corporate America.
The Apple II changed the world and it changed us. As you enjoy, ask yourself what was your defining moment?

Showing off the Apple II - Harry Brelsford (left) and Jesse Tuttle (right)
Read more about the infamous James Tuttle HERE
Link with Harry Brelsford HERE
Let’s GET STARTED. Below is the GOOD STUFF!
Harry Brelsford | CEO | SMB Nation & O365nation | 0:04
Hey, Nation, Nation, Harry here. We have a couple of, well, we have a guest and we have a couple of people over in the sound room. So I appreciate Reese and Andres in the sound room helping us out. But our guest is Jesse Tuttle. We'll get to that. But guys, this is a Dog Days of Summer fun podcast. We need more of that in our technology space. And the topic is,
At the highest level, it's how did you get started? But more specific, Jesse and I have been interacting with his lovely wife and his endeavors over in security. And we found we both basically started with the Apple II Plus. So Jesse, how are you doing on a summer Friday?
Jesse Tuttle | AP2T Labs 0:46
Man, I'm loving it. Plating a grill out this weekend, pulling out my professional smoker, throwing a brisket on it. I am so excited.
Harry Brelsford | CEO | SMB Nation & O365nation | 0:55
Boy, that's Texas talk.
Jesse Tuttle | AP2T Labs 0:58
Right here in Cincinnati, Ohio. Yep.
Harry Brelsford | CEO | SMB Nation & O365nation | 1:01
Yeah, you know, I'll keep the light on. Y'all come visit Austin. I'll keep the light on. Jesse, you go first. Please introduce yourself. You've lived in a couple different realms, and then more importantly, the focus today is the Apple II Plus.
Jesse Tuttle | AP2T Labs 1:17
Yeah, for anyone out there that doesn't know me, which is probably most people, Jesse, better online known for a long time as Hacker Jack from the group Hack Wiser. I was a former world's most wanted hacker that turned
It got contracted and compensated to become an intelligence asset, continually hacking government and military systems and helping secure them and bringing modern day compliance and security to the forefront of everyone's mind.
Harry Brelsford | CEO | SMB Nation & O365nation | 1:53
Hey, yeah, hey, Jesse, gang, let's take 5 seconds and start over. I didn't realize I was sharing my screen, which is not what I wanted to do with that artwork. So let's have a five-second pause. I'll edit all this out. So yeah, we'll come back in. Stand by.
Jesse Tuttle | AP2T Labs 2:02
Yeah.
Yeah, yeah.
Harry Brelsford | CEO | SMB Nation & O365nation | 2:14
Hey, Nation, Nation, Harry here. It's a summer day. It's a summer Friday. We're here for fun to talk about the Apple II Plus. I'm with my bud, Jesse Tuttle, who also got a leg up in technology like myself with the Apple II Plus. So, Jesse, how you doing today? It's, isn't it fun? Summer Fridays are the best.
Jesse Tuttle | AP2T Labs 2:37
Dude, I am having a blast. Just been sitting here cutting up with you and your team, but looking forward to the weekend. It's A Friday afternoon. I've already pulled out my smoker and my grill, and we're going to be throwing a large brisket on and having a great weekend.
Harry Brelsford | CEO | SMB Nation & O365nation | 2:43
Thank you.
Yeah, that's Texas talk. I'll tell you, I'll keep the light on. Y'all come visit and bring, you know, we'll have a BBQ contest. But Jesse, the SMB Nation audience may not be as familiar with who you are, and then we'll get to the good stuff. So who are you?
Jesse Tuttle | AP2T Labs 3:11
Yeah, so Jesse Tuttle, you know, online for a long time, I hid who I was, but people that were around in the late 90s, early 2000s, may remember some of the cyber incidents I were involved in, but I went by the name Hackerjack from the group Hackwiser.
Harry Brelsford | CEO | SMB Nation & O365nation | 3:27
Ohh.
Jesse Tuttle | AP2T Labs 3:30
I'm a former world's most wanted hacker and became a US intelligence asset. I hacked government and military systems and helped them secure them, bringing modern day compliance and cyber warfare as relevant subjects in our world.
Harry Brelsford | CEO | SMB Nation & O365nation | 3:44
I.
Yes, sir. And that's a whole other podcast for a whole other day.
Jesse Tuttle | AP2T Labs 3:53
Yes, it is.
Harry Brelsford | CEO | SMB Nation & O365nation | 3:55
So hey, let's talk about how you got, what role did the Apple II Plus play in your career? You go first and then I'll go.
Jesse Tuttle | AP2T Labs 4:04
Oh, no. And by the way, thank you for having me on here with the subject of the Apple II. I travel the world and I speak all the time. Lots of times I even pull up like stories and things from my past. One thing I never typically get to share is how I
Harry Brelsford | CEO | SMB Nation & O365nation | 4:13
Yeah.
Jesse Tuttle | AP2T Labs 4:23
actually got started in technology. And that start was on an Apple II Plus in the late 80s. Yes, it was about 10 years after it came out, 8 to 10 years. My grandpa had an Apple II Plus and then gave it to us when he got a new computer.
Harry Brelsford | CEO | SMB Nation & O365nation | 4:33
Sure.
Jesse Tuttle | AP2T Labs 4:44
And it was totally pimped out. He maxed out to the 64 KB RAM. You know, all this stuff, all the bells and whistles, printer, everything with it. And as a 10 year old boy, Christmas 1989, it was magical. Dialed up to my first BBS and everything.
Harry Brelsford | CEO | SMB Nation & O365nation | 5:01
Yeah.
Yeah, yeah, no kidding. And then what was the progression since then? Did you move on to, did you stay with Apple? Did you go to Commodore? Did you go to the PC? What was your pathway? Because some people stayed with Apple and they still do.
Yeah.
Jesse Tuttle | AP2T Labs 5:22
Yeah. So I lived on that Apple II Plus for, I don't know, about a year. And then we moved. I was going through a hard time in life that I've never really shared or talked about. And that computer helped me a lot emotionally.
It gave me a realm for me to discover and explore. When we moved, all of that just kind of faded away. And then when I got reintroduced to computers, a couple years later, it was on a Packard Bell 486.
Harry Brelsford | CEO | SMB Nation & O365nation | 5:45
I.
Yeah.
Jesse Tuttle | AP2T Labs 6:02
Circa 1993.
Harry Brelsford | CEO | SMB Nation & O365nation | 6:06
Yeah.
Jesse Tuttle | AP2T Labs 6:06
92, 93, right around there. I think it was the CD10 version or CD20. Yep.
Harry Brelsford | CEO | SMB Nation & O365nation | 6:08
Yeah.
Yeah, yeah, no, you're in the zone. Well, hey, I'll go next and then I'm sure we'll have a little bit of dialogue. Folks, we're going to keep it short and sweet because we know you want to go out and BBQ that brisket. So we don't want to, and that's not just Jesse. I know everybody's, you know, Jones into BBQ, but my story is kind of interesting in how I ended up in the Texas Hill Country. I'll go quick.
On paper, I'm from a 7th generation Texas family. Again, you know, nothing like a paper family tree, but my mom and dad met at the University of Texas in Austin, which is why I'm here. And my dad went to law school and studied oil.
And then lo and behold, they discovered Prudhoe Bay, and he became the head lawyer for the Trans-Alaska Pipeline. So that's where I grew up. Nice place to visit in the summer, wouldn't want to live there in the winter. And so I worked on the pipeline in the summers. And
made some coin. The oil industry, you know, that paycheck doesn't bounce. And so when I came back to college, and I think I've been kind of looking at the calendar, I think that was 82, now that I think about it. One fine fall day, I went down to computer land.
and near the college, and bought an Apple II plus, a black and white monitor, 40 character screen, uppercase.
Had to get a floppy Dr. I mean, these are early days, so you had to get the, you know, lowercase to sender, the 80 character card to make it functional. Didn't even have a color monitor. Came back to, at that point I had an apartment, came back to the apartment, set it up, and I was like,
the only kid with a computer, much less an Apple too, and loved it. And Jesse is the same thing. I think with my ADHD, it's like the first thing in the world that understood me, right? It's like, wow, this thing gets me.
Jesse Tuttle | AP2T Labs 8:25
100%, dude, I can relate so much. And okay, I do have a question for you, not to like interrupt or jump in, but one of the coolest things for me, and I wish we still had it in technology, is the manuals where they had printed code in there.
Harry Brelsford | CEO | SMB Nation & O365nation | 8:27
Yeah.
Yeah, yeah.
Yeah.
No, no, no, go ahead.
Jesse Tuttle | AP2T Labs 8:45
and you can retype it, and that's how you learn to program.
Harry Brelsford | CEO | SMB Nation & O365nation | 8:50
I did. Apple Basic. I did Hello World. Hello World in Apple Basic. No, no, that's exactly right. And by the way, it changed my life. It defined my career. And here I am. Everybody's got a story. But my Friday giggle, because the statute of limitations have expired, you know, as a typical college kid,
Jesse Tuttle | AP2T Labs 8:54
Yep.
One 100%, yeah.
Harry Brelsford | CEO | SMB Nation & O365nation | 9:13
You know, well, we'll just leave it at that. Well, we'll get to that. But what I did is in my apartment, you know, the word got out and I was at the University of Denver and you had to sit in the hallway for your time on the VAX machine up at the computer lab, you know, so it might be midnight.
right? It was a thing. And you had to get vax time on dumb terminals. Well, I got a 300 baud Hayes modem, and we discovered that we could sit in my apartment, have a little music on, like the Boulder radio station, if that makes sense. You know, it's all cool.
And people, it was like a time sharing service. The story gets better. Then I discovered, well, maybe I can make money, you know, some time sharing. And then I thought, well, you know, I need to charge for this. And so being college, and this is where the statute of limitations have expired is people started bringing weed over to me to use.
the computer, so they didn't have to go to the computer lab and use the VAX. And then, so that speaks for itself. It was definitely a hoot. And, you know, Jesse, I'll end that story with, I think, a lot of great innovation at that time, and even today in our space,
Jesse Tuttle | AP2T Labs 10:29
Yep.
Harry Brelsford | CEO | SMB Nation & O365nation | 10:35
I'll just say it, is I think a lot of people were stoned. I mean, I think it really resulted in innovation. Back to you, you don't have to catch what I'm pitching. Over to you, sir.
Jesse Tuttle | AP2T Labs 10:48
Oh man, no. So actually, you know, it's a well-known fact that while I was a known threat actor, and this was from circa like 1994 to 2003, I didn't really dabble in weed much, but
I would have a drink. I mean, it would help me loosen up. I would sit back and I had, I'd have creative ideas and, you know, I'm hitting some rum and just enjoying.
Harry Brelsford | CEO | SMB Nation & O365nation | 11:12
No.
Sure. Love rum. Yeah, love rum. Okay.
Jesse Tuttle | AP2T Labs 11:21
It's the drink of the pirates.
Harry Brelsford | CEO | SMB Nation & O365nation | 11:24
Yeah, yeah, yeah, no, you know, and you know, I'll end on this and you'll get the final word, but I'll end my share on this is that it's interesting about the more change things, the more things change, the more they stay the same. And here's what I mean.
Jesse Tuttle | AP2T Labs 11:26
Yeah.
Harry Brelsford | CEO | SMB Nation & O365nation | 11:44
My 27-year-old son does not want to be in the line of work I'm in. So he's doing AI for HPE in the Silicon Valley. He's 5 years into the valley, primarily AI and cybersecurity. Jesse, his first three years were at Fortinet.
So he cut his teeth on cyber and then moved over to AI, which was a smart move. But I don't know, you know, his party habits, but it's just it, well, I have my suspicions in California.
But it's just interesting how it's come full circle, whatever that mean. You know what I'm saying? And it's just, it's different, man. For the kids today, they want AI. The last thing they want is dad, you know, Windows Server and infrastructure are boring. Over to you, Jesse. Take us out.
Jesse Tuttle | AP2T Labs 12:39
Yeah, you know what? I find something very similar because we went through that whole phase. I mean, think of if anyone here has ever seen an apple to screen, you're going to immediately think green. The text is like I close my eyes and I can literally visually see it.
Harry Brelsford | CEO | SMB Nation & O365nation | 12:45
The.
Ha!
Jesse Tuttle | AP2T Labs 13:00
With those 5 1/2 inch floppies, I had two of them. The keyboard built onto the machine, the monitor sitting on top, you know, all of this stuff. I had that full dot matrix Apple printer next to it. I had all of this stuff. And
Harry Brelsford | CEO | SMB Nation & O365nation | 13:14
Oh God, don't get me going. Yeah. And those were expensive. Those printers were expensive, but go on.
Jesse Tuttle | AP2T Labs 13:20
My grandfather was an engineer for GE aircraft engines. And so that's why he originally got it. And then he replaced it and that's how I got it. So I was so lucky to just be so blessed to get every bit of that. But that's where I cut my teeth. And then, you know, going forward, watching everything
Like when I got off that and then I changed school districts, all these things, I ended up with a Packard Bell on Windows 311 for work groups.
Harry Brelsford | CEO | SMB Nation & O365nation | 13:50
Ohh, yeah.
A.
Jesse Tuttle | AP2T Labs 13:53
I then started dabbling into dial-up BBS with that and then news groups. And I watched that whole transformation into like Windows 311 into 95 and 98 and then Millennium. Oh gosh, that was horrible. And then straight in.
Harry Brelsford | CEO | SMB Nation & O365nation | 14:08
Oh God, don't, no, no, don't get me going on me.
Jesse Tuttle | AP2T Labs 14:13
Yup, straight into like 2K server, because I ran 2K advanced server, that was my go-to as a threat actor. And then, you know, XP, and then I watched as, you know, what, Vista and 7 and 8 and 10 and
Harry Brelsford | CEO | SMB Nation & O365nation | 14:29
I don't get, don't get me going on Vista, no sir.
Jesse Tuttle | AP2T Labs 14:32
And it's all this, yeah, it's all this simplification. How do we make it more simplified? But what I see now is there's this huge draw for the super techie, the people that's like cutting their teeth. They want that nostalgic feel. They want that interaction. They want a clicky mechanical keyboard.
They want terminal screens. They want a screen, an interface, even if it's not truly terminal, they want a website interaction interface that feels terminal-like. It's so fascinating.
Harry Brelsford | CEO | SMB Nation & O365nation | 15:08
Yeah, is that funny?
I told you, we've come full circle because that's basically time sharing. By any other name, we've come back to time sharing. Hey, Jesse, thank you so much. And Andres and Risi in the control room, thank you. Stay on the line. Let's go ahead and call it good. And please stay on the line for a minute.
Jesse Tuttle | AP2T Labs 15:14
Yeah.
Harry Brelsford | CEO | SMB Nation & O365nation | 15:29
Oh