Andy Cunningham shares the mindset she adopted and grew that allowed her to desire, then follow her switch from PR to tech marketing and positioning leader. And, the two mentors, Regis McKenna and Steve Jobs, who opened her eyes along the way.

Andy Cunningham Mindset Shifts

MKJ (00:00.76)
Hello, hello, CEO Mischief Makers, Mary Kathryn Johnson here. You can call me MKJ. And if you don’t know my guest today, you are going to be in for a treat because I have the amazing Andy Cunningham joining me on the conversation today. Welcome, Andy. How you doing?

Andy Cunningham (00:17.559)
Hi Mary, thank you. Nice, very nice to meet you. MKJ.

MKJ (00:22.587)
It’s easier, know, people are like, Mary Kathryn. I can’t just be a Mary Johnson, right? I just can’t. That’s just not an option. So I had to put in the Kathryn in there and then nobody can spell it. So I’m like, just do MKJ. We’re good. Well, welcome to the conversation. I really appreciate sharing this time with you. Let’s just kind of…

Andy Cunningham (00:24.827)
No.

Andy Cunningham (00:29.115)
I get that, right.

Andy Cunningham (00:37.819)
That’s great.

MKJ (00:46.328)
just debrief everyone on who you are and what you do, just in case there are people who don’t quite know much about you yet. So tell us a little bit about who you are what you do.

Andy Cunningham (00:55.589)
Sure, so I’m Andy Cunningham. go by Andy, but my real name is Andrea and I’ve always gone by Andy. I started my career in public relations and so I evolved that into marketing strategy and now I do positioning strategy. I’ve been in the agency business my whole life. I’ll get into that story in a little bit, but that’s who I am. I love working with multiple clients because I get the opportunity to learn all kinds of new things. I focus on the tech industry.

So I’m deeply right now engaged, as you can imagine, in artificial intelligence and some healthcare stuff. It’s very fun and software and all of that. I have a small team. I went from having a large agency of about 260 people to I sold that business and kind of bought back a piece of it and now I have just a tiny group of about six people. And I really love working in an intimate situation like that with people I trust and love and it’s great.

MKJ (01:53.228)
Yeah, yeah, how wonderful.

Andy Cunningham (01:53.881)
including my kids, they both work for me. And so does my husband.

MKJ (01:57.656)
Isn’t that great? Isn’t that wonderful? I know I when mine were younger, I had them working for me. And then they that was just kind of an idea for them to see what’s possible and how they could use some of their innate skills, the way they look at the world to to explore how they can, you know, potentially join the workforce with their innate skills. It was so fun. It was amazing. I had my my oldest editing and and producing my podcast.

Andy Cunningham (02:03.707)
Yeah.

Andy Cunningham (02:21.155)
It is fun.

MKJ (02:26.554)
Since he was like 16, right? It was it’s amazing. It’s wonderful now He’s got his own Pontus production business that of course I have to pay him a lot more now He still does it yes, it’s wonderful and that was my goodness that’s nine years ago now That he started that it’s coming up to a decade. my goodness that I that blew me away just now that realization anyway

Andy Cunningham (02:26.896)
that’s great. Wonderful.

Andy Cunningham (02:37.337)
He still does it for you though, right? That’s great.

Andy Cunningham (02:45.648)
my gosh, wow.

Andy Cunningham (02:50.127)
Wow.

MKJ (02:54.458)
Let’s talk about mindset. So I know you have been on an incredible journey working with some really incredible, talented people, as we all hopefully get to do throughout our working lives. But you have specific stories to tell. So you said agency, you’ve been in pretty much your whole working life, but you grew an agency, which of course, well, let me ask you this first. Were you an accidental agency person? Did you just accidentally fall into agency work or did you plan that?

Andy Cunningham (03:23.419)
No, well, I guess it’s sort of accidental I was actually wanted to be a writer and I was working in the in a trade magazine Publishing company in Chicago when I graduated from college and the pay was terrible. Absolutely terrible and I needed to make more money and so I went I Found a job interview at you know, the magazine called playbill magazine I don’t know what they call it’s made it’s when you go to a play and you open it up and you you know learn all about the actors and all that

MKJ (03:46.617)
Yes?

Yes. Yep.

Andy Cunningham (03:51.771)
I interviewed with the editor of that magazine back 100 years ago and she was willing to offer me a job but she said I can’t pay you much more than what you’re already making and it’s probably below where you actually are in your career. So do you mind if I introduce you to a recruiter that I know? And she did and he said you need to be in PR and I hated, I hated PR because I was a you know a trade journalist who basically was being called 95 times a day by PR people trying to sell me stories on their

engines and oil and transmissions. wrote for a truck magazine. So, but anyway, I went on the meeting and I walked into two agencies. got me interviews with, one was called Edelman and one was called Burson Marsteller. And the minute I walked into those places, I knew I was in love with the business. The buzz, the energy, the creativity that you could see around, was fabulous. So I ended up getting an offer from both, but I took the one at Burson Marsteller.

and ended up in their technical group because I had been writing a lot about technical stuff and so that kind of introduced me to the whole world of technology and kind of I went from there.

MKJ (05:02.456)
Isn’t that amazing? through a through just a conversation, a relationship that you developed with Playbill with them saying, okay, we can’t really pay you. like you, but we can’t really pay you that much. So how about if I introduce you to a recruiter who can maybe get you a job somewhere else that can supplement what you’re doing here? And now you’re in an agency and that basically hits, it starts the trajectory of your entire life. Isn’t that crazy?

Andy Cunningham (05:18.33)
Yes.

Andy Cunningham (05:28.279)
Yes, and it doubled my salary too. Believe me, I was making nothing in the trade journalism space. So doubling it was still not much, but was at least I could live and eat. So, yeah.

MKJ (05:33.494)
Thank

MKJ (05:40.216)
Yeah, and it’s a path, right? Like you said, it was, you loved the energy. You loved, I love that too. I love being able to, you know, I’m a person who, I’m not as much a maintenance person, just not, right? Yes, I make my bed. Yes, I brush my teeth, right? So I do the things that typically we need to maintain. But if I, once I get bored, once I master something and it’s no longer exciting, I need something else. And agency work completely opens that up for you, right?

Andy Cunningham (05:45.008)
Yes.

Andy Cunningham (05:51.13)
Yeah.

I

Andy Cunningham (06:09.731)
It’s a wonderful, I love it because you get so many clients, you can do so many different things, so many different industries. It’s never the same thing over and over again. It’s very stimulating and you’re never constantly just working for the same person all the time. It’s different people as well, so it’s great.

MKJ (06:27.022)
Right? Yes. Yes. Yes. So now you started working in that agency and you were what were you? You were account manager. Were you an actual copywriter?

Andy Cunningham (06:35.289)
I was, yeah, I was an account manager and I got a couple of promotions. I worked there for two years. But what happened is that Burson Marsteller, which is a big international PR firm, they were opening up an office in Silicon Valley and my colleagues there knew that I was in love with technology. And I’ll just to back up and give you a little story. One of my clients was a company called Bell and Howell, which I know you’ll remember.

MKJ (06:58.564)
Yes, I do. Yeah.

Andy Cunningham (06:58.831)
But many of your listeners may not. It still exists as a company, but back in the day, it produced educational hardware. know, projectors and overhead projectors and other kinds of stuff like that. And anyway, they did a deal with Apple, and the only company that ever did a licensing deal with Apple. They licensed the Apple II. They took the beige cover off the Apple II. They replaced it with a black cover, because that was the Bell and Howell color. And it was known in the industry as the Black Apple.

And it was sold to schools, sold to educational. So they were my client, my first client. And I had this incredible opportunity. They gave me one of these computers. This was like in 1981 or something. Yeah, 81. They gave me one of these computers. And I brought it into the office. And the librarian and I just had the most fun you could possibly have at work.

MKJ (07:43.012)
goodness.

Andy Cunningham (07:52.699)
playing with this computer and figuring out what it could do. And it could not do that much back in 1981, believe me. But anyway, I fell in love with it and all my colleagues knew that I was in love with this computer. And so they would put articles of what was going on in Silicon Valley on my desk every morning and just talked about it a lot. And then finally the company decides to open up an office in Silicon Valley. So I said, know, hey, can I interview out there? Because I was in Chicago.

MKJ (07:58.01)
Right, right.

Andy Cunningham (08:22.555)
And so they flew me out and I met with the guy that was running the office and I just kind of knew immediately I could not work for him, which was really sad because I loved the company. But he was just one of these, what we would call today a tech bro. And I knew back then I just couldn’t work with him. So I took the rest of the afternoon and went to every other agency that I possibly could find in Silicon Valley on short notice like that and I said, hey,

I’m here from Burson Marsteller and I’m interviewing at Burson, but I’d love to also chat with you if I could. So I got like four more interviews that day. And the very last one of the day was with a firm called Regis McKenna. And I got to meet with Regis himself. And Regis at the time was the marketing guru of Silicon Valley. He was Steve Jobs’ father figure and mentor. He did Intel’s work. did every, Microsoft, all these companies were his clients. And he is still amazing. He is still around and he is still amazing.

He’s got amazing intuition for marketing. So anyway, he offered me the job on the spot to run the Apple account for the launch of Macintosh, which was like a dream come true. I couldn’t even believe I was hearing this. And there are a lot of circumstances for why he did that. But the biggest one of which is the company had just launched the Lisa computer. And the Lisa computer was an abominable.

failure in the market. did pave the way for Macintosh, but it was a huge failure. And the whole team at Regis McKenna that had launched that product quit because they were tired and they were weary. so they, yeah, they quit except for one young woman named Jane. And Jane and I kind of paired up as a unit, if you will, and wrote the Macintosh launch plan and…

MKJ (09:57.656)
Yeah. Disillusioned.

Andy Cunningham (10:12.673)
She and I pretty much did the whole thing almost by ourselves. We were allowed to hire a couple of other people. So we had a very small team of really great people. And she and I did the whole thing from a PR perspective. Of course, there was a great ad agency in Shia Day. There was a great marketing team at Apple. Steve Jobs was very, very difficult to work with, but also amazing, really great marketing insight. I learned a ton from that experience.

MKJ (10:42.18)
I got it. got to say. you go from a Chicago PR firm agency. And of course, everybody knows you love tech. You have a client who is the only licensee of a Mac and they give you a black. Excuse me, an apple too. They give you a black apple. Is that what you called it? A black apple? Yeah. So they give you a black. I just that’s crazy. The name.

Andy Cunningham (10:57.741)
Apple II, Apple II.

Andy Cunningham (11:06.946)
Thank

MKJ (11:08.28)
So they give you a black apple and you get to play with it. You’re all excited. And the firm is like, yeah, this is cool. You know, sure. Go out and we’re opening up an office. so tell me you as a person, you go from that to working for another firm, getting out there and just deciding I’m going to find another firm because I want to be here. I want to be in the middle of this. And this is in the 80s and

Andy Cunningham (11:30.895)
Yes. Yeah.

Yep.

MKJ (11:35.694)
You’re like, I want to be in the middle of this. What shift was that from writer for a playbill to PR agency? Yeah, I love this work. I love the energy to I’m in Silicon Valley and I want to work for one of these firms. Tell me, how did you do that? How? How did you just decide to do that?

Andy Cunningham (11:42.949)
Bye!

Andy Cunningham (11:57.381)
Well, I was young and single, although I was engaged. my husband at first didn’t want to move out here, because he had a career and a job in Chicago. But we finally ended up coming to an agreement that we would do that. So there was that. But aside from that, this is where it was happening. I mean, in the world that I was falling in love with, which was technology, everything was here. Semiconductors were here. Personal computers were here. Apple was here. It was just where everything was.

I was like such an incredible honor to be in the middle of all of this. I I grew up here in Silicon Valley, essentially. I became who I am today because of all of that. And it’s just an amazing place where one of the biggest thing I noticed, speaking of mindset shifts, biggest thing I noticed is back in Chicago, I had actually wanted to start a company there, not an agency, but a different kind of a company.

And it became apparent after I went around talking to people that it really wasn’t going to happen for me there. I was too young. I was too female. And Chicago is an old boy network kind of town. And I didn’t know any of those people. So I decided if I went to Silicon Valley for a few years and learned how they did the entrepreneurial thing out there, I could come back to Chicago and I’d have more credibility. Well, the minute I got out here and started

playing around with Apple and I had another client called Digital Research, which was a big competitor to Microsoft back in the day. I said, I’m never going back to Chicago. Because you can be anyone in Silicon Valley. You can be whatever, anything. You could be a Martian. Nobody cares about anything about you except for what you can do. And that was great.

MKJ (13:38.97)
That’s it. So you went from, have to find a way to gain the experience and knowledge to fit into this world, to have me fit this world in Chicago. But when you went to the place where you thought you needed to gain that knowledge, you realized, screw that. You don’t need to fit into anybody else’s world. You can create your own world.

Andy Cunningham (13:47.002)
Yes.

Andy Cunningham (13:53.275)
Yeah.

Yes, and I can do it best here in California. it’s a, it is still a mindset shift being in California. It’s not like the rest of the country, especially here in Silicon Valley. And so it’s a, it’s a, it’s, still, I know there’s, there’s been a lot of complaints about the bro culture and a lot of other issues like that, that we’ve had to face, but it’s still a place where changing the world matters a lot.

MKJ (14:11.917)
In what way?

Andy Cunningham (14:25.197)
and that’s really what people want to do. Now they also want to make a bunch of money with that, which is fine. But at the core of what they’re trying to do, they are really trying to change the world. Almost everyone who’s here is trying to do that. And that is just very inspiring. Some of them do it better than others, of course. I was lucky to have worked with the best, with Steve Jobs. But it’s still kind of the underlying ethos of this place. And also, be anybody you want to be. You can be…

anybody you want to be and you can come from anywhere. no one is looking at your anything, your skin color, your religion, your sexual preference, your gender. Nobody’s looking at any of that. They’re just looking at what you can do for the most part. And I think that’s just so refreshing. And Steve Jobs was 100 % like that, even back then. He had no other agenda, none, other than just changing the world with this product. So it’s very refreshing.

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