Maxine Cunningham - Pick My Brain

Maxine has quickly become one of my favorite people in the world and this episode was so much fun to make. Her passion for connecting people and sharing knowledge through those connections is easily felt when you talk to Maxine.
We explore the themes of entrepreneurship, collaboration, and the evolving work culture. Maxine shares her inspiring journey from a stable corporate job to becoming a successful entrepreneur, and we discuss the importance of energy, self-belief, and unlocking hidden talents within organizations.
We also touch on the need for a new marketplace that values diverse skills and experiences, and the shift towards a more autonomous work environment. Maxine and I dive deep into the transformative power of conversations, the role of networking, and the potential for platforms that connect kids with professionals to expose them to diverse career paths.
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Summary
Maxine has quickly become one of my favorite people in the world and this episode was so much fun to make. Her passion for connecting people and sharing knowledge through those connections is easily felt when you talk to Maxine.
We explore the themes of entrepreneurship, collaboration, and the evolving work culture. Maxine shares her inspiring journey from a stable corporate job to becoming a successful entrepreneur, and we discuss the importance of energy, self-belief, and unlocking hidden talents within organizations.
We also touch on the need for a new marketplace that values diverse skills and experiences, and the shift towards a more autonomous work environment. Maxine and I dive deep into the transformative power of conversations, the role of networking, and the potential for platforms that connect kids with professionals to expose them to diverse career paths.
Throughout our chat, we emphasize the immense value of human connections and how they can shape our understanding of the world. This is an episode filled with insights, inspiration, and a glimpse into the future of work and entrepreneurship.
Maxine:
Imagine if you could book anyone in the world for 3 months for a package where they just create for you. So You
Kyle:
and I agree. I need a thing. You can do the thing. Why don't you do the thing for 6 months? And then we'll reevaluate in 6 months and see if you wanna keep going or maybe you wanna go do something else.
Kyle:
You're just gonna have so much of that sort of, like, time based contract.
Maxine:
That is really empowering when you get people to be like, what? What do you need? What is possibly I'm like, do you have any jobs are out there? Do you have any people are out there? Do you have any countries that are out there?
Maxine:
Well, it's just there's abundance. It's it's there's goal there's piles of opportunity.
Kyle:
Getting out of your head and getting out of your own space, and then you sort of, like your energy shifts and you're different. And you're like, okay. You know what? Now I'm gonna go do something. So
Maxine:
Being an entrepreneur is a very high energy job selling things. So I was like, okay. I made, like, $3,000 selling coffee and conversations. What else do I sell?
Kyle:
Now, is this the point you buy a domain name?
Maxine:
Hi. Thank you for your patience.
Kyle:
How you doing?
Maxine:
So good. Back home. Home soil.
Kyle:
You're back you literally just did you just slide into the How you doing?
Maxine:
I'm good. I'm good. Sorry. I'm just landing, so I'm like, I'm gonna zone. And now I'm like, alright.
Maxine:
Let's
Kyle:
Tells wait. Let's let's settle home with. Right?
Maxine:
Mhmm. Grounding. Here.
Kyle:
And for all the audio listeners, we're just sitting here. So we're just taking a second. So just sit with us. Where did you go? Where where where was your where
Maxine:
did you go? I was in New York for a month and a half, and then I was in Colorado for about a month and a half. Yep. Oh,
Kyle:
do just all all work work too long?
Maxine:
No. It's always work and play. But, yes, there there was a mission to, introduce New York City's public school system and Colorado's public school system to Pick My Brain's vision.
Kyle:
That's amazing. Way back. That's so good. I will tell you before we before we sort of jump into to your past and to pick my brain, 2 amazing pick my brains this week. So you recommended that I meet Perry or doctor Octopus.
Kyle:
And that was we could have talked forever on just all the things, and it was a very nonlinear conversation as you can imagine Yeah. Which, is is so good. And Charles, that was that was such a good I think we booked 30 minutes, and I think we talked for an hour intake, or something like that. So it was You were gonna
Maxine:
send some more recommendations your way. I love sprinkling brains for people.
Kyle:
Oh my goodness. Well, it's it's so good. And you know what I thought? I thought should have been recording those sessions when I when I was talking to Charles and and Perry, which made me think, we should do a podcast called picking my brain.
Maxine:
Let's there I was I told Perry I even consider putting Riverside as my Zoom link when people book me for pick my brain calls. To be like, listen, we have free time, but I record it, and I am gonna post it. Because this is what I'm ampl this is what I want more of, conversations between people. So maybe what if I turned to all of Pick My Brain? I'm like, anytime you book something here, it will be recorded and shared on the YouTube.
Kyle:
Oh my gosh. Or if yeah. If you could make it an option, and it was basically, like you know? And then you could have clips pulled from that. I think it would be really interesting.
Kyle:
What if, like, what if together or independently, what if we went around and we and we just did random search? And it was somebody you didn't know, and it was somebody I didn't know, and we just set up time and then we were like, hi, who are you?
Maxine:
We used to do a show. I've got this idea so much. Imagine going I'm just like visualizing going to like pick my brain right now if I just like pull it up, you know, like people scroll like
Kyle:
And what if yeah. And what if we were like, okay. Wait. Put in basketball. Right?
Kyle:
And we just and then we pick somebody and we book them and then you and I show up and we're like Oh my god. What do you do? Conversation for you. Tell us about your tell us about your life, you know, and then we just dive in and who knows? It's like spinning the wheel and it's like who knows where it goes.
Maxine:
This is so good. I can see it all the way from the top of the line. I'm awfully I thought of I've always thought of doing a podcast for pick my brain, but I haven't been ready, but I love the, like, Carmen San diego style, like, where you're in
Kyle:
Totally. Yeah. You could literally have an animation that sort of spins around and lands on the person's profile, and then it's like, okay. Here we go.
Maxine:
You know, with all of the gratitude in my heart and embedded into my little brain, I am so loving. My dad always said he's like, Max, I really want, like, almost like a roulette. Like, I pull pick my brains lever and it gives me 3 options. And I'm like, just go talk, you know?
Kyle:
Totally. Yeah. Yeah. Yeah. Oh, it's like, Google's are you feeling lucky?
Kyle:
Like, if you just had a if you had a thing where you basically spun and it just and if your both of your calendars were were synced that it just sort of said, like, great. I just made, an auto date for you and you're gonna talk about and it gave you, like, 3, like, starters.
Maxine:
Like, that's what I want to start my day. People start their day with 30 minute walks or 30 minute adaptations or I, like, really wanna just jam about current events with people around the world or what they're up to or their story. That's I want a little 20 minute, 30 minute connection.
Kyle:
Yeah. Yep. And I'll I'll tell you that, like, I've this week has been a very draining week, and it's one of those that, like, I I think I had I've had 2 mornings of the past mornings that I've, like, just I don't know. Just energy and, like, what what, how you know, and very in my head and whatever. And I'll say that, like, after talking to Perry, I'm totally different.
Kyle:
You You know what I mean? Like and just being able to also get out of the we even talked about it. Like, it's, getting out of the matrix, but but just getting out of your head and getting out of your own space, and then you sort of, like your energy shifts and you're different. And you're like, okay. You know what?
Kyle:
Now I'm gonna go do something. So
Maxine:
I'm so grateful you just said that because as an entrepreneur, your energy is everything, and it is a different energy exertion than anything I've ever done. Being an entrepreneur is a very high energy job, and same, like, I definitely have lulls, and you gotta, as an entrepreneur, figure out how to get your energy back in check because you're, like, constantly out there, and conversations for me do that. I I have to pull out. And then something happens, like, this collaboration of both of our brains coming up with an idea, and I'm like, back in creation. I'm like, cool.
Maxine:
Let's go.
Kyle:
Totally. I had I had that, where yesterday where it was, like, I I was I was kinda feeling sluggish. I even took it, like, a little nap at, like, 10. Like, I was just kinda trying to reset in the morning, and I was and and you start you find one of those days where you're like, I just wanna kinda make it through. I wanna try and get as much done as I can in this sort of space.
Kyle:
And then I had and then after 1 or 2 conversations, I was like, wait. I found juice. I found flow. Like, I put the kids to bed, and I came in here. I put on my headphones, and I was like, put I was up putting, like, Guns N' Roses on, and I was just, like, jamming until the night.
Kyle:
Like, I just, like I'm just, like, getting it. And I I would have never thought I would have been in that place at, like, you know, 9 AM that day. I would have been, like, no.
Maxine:
Oh, you honestly, I wanna sell it as energy. I'm, like, 30 minutes of energy is $50. An hour of energy is a 100. You know? Because it is that.
Maxine:
It's really not what knowledge do you have. We're almost at we're almost reaching this convergence in society where we have we all have access to unlimited knowledge. You know, it it you're Totally. It's just meat and jam. Yeah.
Maxine:
Totally. I'm glad that experience and you shared it.
Kyle:
So where does it come from? Where did it where did the I'd love to go back, like, let's so let's do a TLDR before Pick My Brain started, back in the economy economist periods. What was where was mass, minus 1 year, from Pick My Brain?
Maxine:
I was at a job. I was working at a company called the International Institute of Sustainable Development in Ottawa, the capital of Canada, thinking about international cooperation among countries to stay in alignment with the planetary boundaries, which is a really cool job and a really cool thing to think about. However Mhmm. I had just seen a first policy that had so much energy in it and years of experience, and it get dismantled because of a change in government. And I had this shift, one of those moments of being like, I can't be in policy if I I'd I was too green to know that people could roll back policy, and we're gonna see it happen right now real fast.
Maxine:
Regulation gone. Regulation gone. Department fired. And you realize, like, all the work like, that's a lot. That's I so anyways, I was I was realizing that at the same time I had just discovered Airbnb.
Maxine:
And I was a cold surfer before Airbnb, and I was always saying, you know, someone should come and monetize this thing, and Airbnb did. And I think I was one of the first people in Ontario for sure on Airbnb, like, discovered it very early. And the idea made my mind go like what our beginning of the call was like. I was like, what? I was like, this thing's gonna change the world.
Kyle:
You can see the future. Like, all of a sudden, you see, like, 5 or 10 years into the future and you go like, oh, and you see every little. And what's interesting is that I actually had a great call with Ben for who started Contra. And, Contra dotcom as as the sort of, like, the new where you where you go to find talent and, in creative and and development and writing, all sort of things. And, and very much like Airbnb, I think he also got lots of this.
Kyle:
Like, this is a terrible idea. I think they just raised their series a. It was, like, 46,000,000 or whatever, but we even talked about on the on on that episode, which was, like, think about back to get picked up by a stranger and get taken somewhere. Even even the screen likes it. Or go sleep in someone's in a stranger's room
Maxine:
Right.
Kyle:
In their house. You know, how many people would be like, this is terrible. Like, how are you gonna make money doing this? But what's amazing is I love that your brain sort of saw, like, all the way down the line and and saw where that could go, which is great.
Maxine:
Well, I I think it was because I couchsurfed. I probably stayed on 50 plus couches and had 50 people stay on mine and really understood what Brian was originally starting the company with, which is bringing community into the home, and you are welcome anywhere. And the second thing I saw was from my environmentalist hat, that we're I knew how wasteful hotels were, and to share an asset and get more ROI on it is something that is near and dear to my heart forever or will always be. I was like, yes. This is environmentally sustainable and community driven and trust enabling.
Maxine:
And then the third thing I saw was how fast it turned people into entrepreneurial thinking. You know, I immediately lit house. I was like, woah. This is power. You know, like, I am an entrepreneur.
Maxine:
You know, this is entrepreneurial, entrepreneurial, and people are just gonna think about numbers and marketing and showing their house off and putting systems together. It's a game. That's what will stack. And I and I was, like, this is gonna be done next thing. And and so 1 year ago before Pick My Brain was started, which is about 7 to 8 years ago now, I quit my job a week or 2 after discovering Airbnb and being like, I need to be in that world.
Kyle:
I love those moments.
Maxine:
Yeah. Yeah. So remember talking to the CEO of my company and walking around Ottawa's parliament and telling him, I'm so sorry, Scott. I have to leave our mission. I have to take this year on and discover marketplaces, startups, and tech.
Maxine:
I I I must follow this.
Kyle:
I have seen a vision. The hairs are standing up on you know what I mean? Like, they're gonna be like, oh, that's so good. Yeah. And then that moment, like, was it also, like, was there you know, because a lot I think for a lot of people, that's a that's a hard place to just sort of drop those bags and walk into into the not knowing?
Kyle:
Like, what was your did you feel so strong about that, like, vision and that and that that pull that it didn't you you weren't really sort of thinking about those things?
Maxine:
I think I've always, from the day I was kinda very young and born, I don't have fear of dropping and changing on a dime. I my brain doesn't conceive it the same way. Maybe it's my and also as an economist, I don't conceive it. Like, I'm like, sunk cost. Let's go.
Maxine:
New world. We'll create and I truly believe in my ability to create, and so it's not scary. If you are if you don't have the self belief in yourself, it would be very scary. But I think I have 100% belief that I can create my destiny. So I was like, I'm gonna go on the start up journey and create a start up and become a start up founder.
Maxine:
That's okay. Figured it out. And and I did, and I gave myself a year to play in that space. And I think having done that, it's something I would wish upon the world. You know, a big percent of us go to university.
Maxine:
I really wish of a world one day where a big percent of us take a year to explore our creativity and follow our intuition and slow down and notice and build a deeper relationship with oneself, and you will be so surprised at what you can unlock. That will you forever. Like, 1 year on serves you for the rest of your life. It's a real good trade off.
Kyle:
Totally. And that's, that's really like, if I can if I can give one of the biggest things, you know, I think for me, when I look back at, like, I've, I my mom, my and my dad have both passed and, like, you know, and as the nuclear family sort of leaves, I also think about my mortality and those sort of modes. And I and I think about, like, what could I pass on to, to my kids? And it's not just like a an okay 401k. Like, what I really want is to sort of pass on that idea of the same thing.
Kyle:
I've done that so many times. Like, I've been in a really nice, healthy paying job, and I've seen something where I'm like, nope. That's bullshit. And I'm like, alright. I'm leaving.
Kyle:
And people go, wait. Wait. What are you gonna do? And I'm like, I don't know. And every foot of the office goes like, well, what does that mean?
Kyle:
Like, what what does what does next week look like? And I'm like, we're gonna we're gonna figure it out. And there's such power in being able to sort of just Yeah. Like, listen to your heart, listen to your, like, gut, and then, like, make a change like that. And, also, I think it it expands time because you you spend more time sort of, like, taking things in versus just, like, you know, going down the linear path.
Maxine:
So so true. And I think that is really empowering when you get people to be like, what? What do you mean? What is possibly I'm like, do you know how many jobs are out there? Do you know how many people are out there?
Maxine:
Do you know how many countries are out there? No. It's it's there's abundant. It's it's there's goal there's piles of opportunity. One station unlocks 6 businesses.
Maxine:
Like, it's okay. Like, just calm. Yeah. But it's empowering to give them that moment of contemplation. You know?
Maxine:
It's the power to I think that there is this revolution happening right now. 47,000,000 Americans have left their careers. K. That that's a movement, and I think they've a big percent of them, according to a few surveys, have left because autonomy is worth everything. When I can be and stay at home, when I can go on vacation with my kids, when I can choose, that is basic, you know?
Maxine:
Yeah. What's up?
Kyle:
I can manage my life how I want to, and I don't have to cram it in between, like, 7 and 9 PM or whatever. I also think that, like, you know so I'm 45, born in 79, and I really think of sort of myself as the, like, heart of the Nintendo generation where it was sort of, like, you know, you had sort of, like, parents that were, like, these, like, video games and computers. Like, they seemed like sort of extra toys, but the people who sort of grew up in that, like, Atari, Mario, Duck Hunt, like like, it it actually is more ingrained and then younger. So you're talking about people now who are in their thirties and their forties who are used to sort of working in this way, starting to come in, you know, a lot more into power, which also means then and and management of these companies to where, you know, you're getting, I think, less of what I feel like is that that sort of older what I think of as, like, the bank, kind of, like, we we have suit. Yeah.
Kyle:
And this is what we do. We have the crisp resume, you know, and you have a lot less of that which which starts to and, you know, and now a lot more freedom to to move different places and to work forever because we can do this like this. And I just I love it. I love I love seeing all those
Maxine:
Move through. And I think the the key transition is really more entrepreneurial mindset, more entrepreneurial, living, design, which is nonlinear, and which requires a certain level of self awareness, and capacity, communication skills, free and energy. You know, influence you gotta be able to influence. You gotta be able to, bend your reality. And I think the more people that learn how to play with that simply by starting you don't have to go all in.
Maxine:
It's like you have to go all vegetarian or all entrepreneurship or all Karen Kardonoker. You know, the the you're right. The systems that exist allow you to jump into entrepreneurial mindset and play on the side, and that is empowering. That's still conscious elevating. That is still a faster speed of growth, you know, range a larger range of capacity and, emotions.
Maxine:
So if as I say, I'm like, you know, like, I do agree with Elon Musk. Like, don't do it unless you can't not because it is, like, chewing glass and staring into the abyss. It is it
Kyle:
definitely is what that's where I feel like. I it's like having 10,000 tabs tabs open in your mind, and your computer's going like, hold on. I just I can I see can I just have a minute? Like, I'm starting to overheat. But at the same sense, it's kind of like driving a race car where, like, you feel those moments where you're kinda like, oh, I'm soaked up this.
Kyle:
Well, I'm the only one who sees this thing or and that that is that is so different than I think when when you sort of get into the safer habits of, like, I know how to do this. This is super like, I've I've got this down pat. And my brain always, a second I get to, like, I've got this down pat, I'm like, yes. But what's next?
Maxine:
Truly, it is that it's and I feel like it's, like, for lack of, like, the negative side, it's a disease that takes over. It gets stronger and stronger, and then you're, like, terminally an entrepreneur. Like, oh, shit.
Kyle:
Yeah. Yeah. Totally.
Maxine:
Yeah. I'll never let go bad, but I don't anymore. You know? I don't even know if I wake up.
Kyle:
And I love
Maxine:
talking too. I love not fitting too. And it'll be interesting to watch the world balance that yin and yang, that structured, non structured, linear nonlinear relationship because just this this was it yesterday? I was having a call with an operator, and he's like, you know, he's like, I don't have a visionary bone in my body. And I was like, I don't have an operator bone in my like, you know, I am not an operator.
Maxine:
And yet we both need each other to be successful. And that is the beauty is when you can, like, match freedom, entrepreneurship, visionary, creation to structure. You know, it's it is the pairing, and I find society is, like, we're better than this group or this group's better than this group. We're like, you can't do it without me. And it's just like all this especially after being in the states for 3 months, I'm like, you guys.
Maxine:
Like, oh, it's so so
Kyle:
Totally. Yeah. Yeah. I think it's like, when I think about, like, you know, we were talking about this sort of, freelance, boards where you can go and sort of get, like, a gig job, and I think that is definitely the future where it is less of this, like, I interview you. We are are we agreeing to stay together for 2, 5, 10 years?
Kyle:
You're going to make your career here. You're and then I'm sort of like, what if you don't wanna stay? That it that is all gonna collapse into, like, how about you and I agree. I need a thing. You can do the thing.
Kyle:
Why don't you do the thing for 6 months? And then we'll reevaluate in 6 months and see if you wanna keep going or maybe you wanna go do something else. You're just gonna have so much of that sort of, like, time based contract type work, which allows you also to I love learning different I you know, I've worked at agencies. I was also, like, in the second floor of a house with Kevin Jonas running a start up doing a game on a mobile app. Like, you know what I mean?
Kyle:
Like, that's not a resume thing. Like, are is are you are you fit for this? Like, you just kind of but that teaches you so many different things, which then I think has obviously led to to making entrepreneurial, sort of start up life better because I've seen so many different things and so many different parts and jobs versus, like, being in this one specialty. So
Maxine:
So agree. And that's exciting. And so there's 2 parts of that. I imagine, like, Pick My Brain is at a place where we can support that economy as well, because I don't know if it's as gig. It's too gig and transactional right now for me.
Maxine:
I do want it to be I as you were just saying that I was crafting an offer in my head, which I often do, and I'm like, imagine if you could book anyone in the world for 3 months for a package where they just create for you. So so I don't care who the person is almost, but the 1st month they spend learning me what pick my brain is up to, what our is, and I have a call with them. I'm like, you have potential. You have it. You have the juice.
Maxine:
So let me buy a 3 month package from you and it not be defined with a statement of work and do this many posts, but, like, I'm like, no. I I trust in your ability to add something of value to my company and my mission. And I want you for 3 months, your energy and your consciousness to put whatever it is you wanna work on in my company. In order for me to trust that you can do that, we've already had a 30 minute call and I see it. So commitment made for 3 months.
Maxine:
Here's 10 k, whatever the price is. And I'm like, Kyle, now I want you for a month to just meet me. Learn about me. Ask me about my story. Ask me about all the case studies that put my brain, where we're at, where we're going, my vision for the future.
Maxine:
Get do that for a month with me. And then 2 months, and it can be on your own time. That could be 1 90 minute conversation. That could be 2, whatever you feel. I have no commitment to the and in.
Kyle:
Yep.
Maxine:
In month 2 and 3, I just want you to create something that you think would add value to that. Anything. And if I the 3 you know, and I I'm just materializing this right now. What a beautiful marketplace to shop. And how much does that allow me?
Maxine:
Not I don't wanna hire employees at Pick My Brain. I wanna hire people that wanna add value consistently to the platform in a way that makes sense for their lived story and experience and relationships.
Kyle:
And where they're at from a sort of, like, a flow perspective in their life or in their because there may be moments where they sort of can come in and sort of create something different. That may be totally different a year from now, and so, like, I love that flexibility. So you're talking pick my brain, and then the sister used my
Maxine:
brain? Yeah. I'm like, my dentist call you, like, just so do you want my 10,000 package? I'd be like, yeah. I'm like, you know?
Maxine:
Like, that's it. That's what we should be able to do. We should be able to talk and hang. I gotta write that down.
Kyle:
But you know what's really great about, like, about the sort of use my brain side of things is I think that so many times, even when we're building a company, it you do have to create the matrix. Right? That and and everyone drinks the juice and everyone sort of gets on the same page so that we can create together and we can sort of create that alternate reality. But, also, I don't think we'd I think we're always so so focused about what we do. We we need this thing.
Kyle:
So let me go find this thing and let me fill this thing, but I love this idea of putting this this sort of foreign body in and going, you analyze this and then tell me what you think is could add value or would be different or a different perspective, which then gives me, oh, wait. I haven't even I've been so focused in this one direction. I haven't even thought about, which could then sort of add a totally different value. And so you're almost inviting someone in with a totally different perspective to to sort of give you something to change the color and the palette of what you're doing, versus asking, you're yellow? Okay.
Kyle:
Great. I need yellow. Please come in. Please be a yellow. And then and instead, it's like, why don't we get a fuchsia in here and see
Maxine:
what happens? Yeah. Or and you're that's so so right because even in jobs, we we write an ad for the job that we want fulfilled. We say what we want that person to do. We say what we're requiring, and then we find that person and fit them into that job and get them to do that job.
Maxine:
And I'm, like, I'm I'm all about this is the economy today, and I just wanna swivel it. Like, there's just swivel that needed. Like, let's just for fun swivel it. Totally. So what I realized, and I was interviewing Mitsubishi, for a project a while ago, and they had 80,000 employees.
Maxine:
And what I learned when I interviewed those employees was how many skills that were housed in those employees that were not being utilized because the job wasn't written for it. So I went to this you're born as a hit. You know that you have someone on your team that is the 2nd best saxophone player in the world. You know, Did you know you have people that are doing certifications on leadership design and are not did you even know that a bunch of people are doing that? Did you know that you have Reiki healers in your organization?
Maxine:
Did you know? Like, I just kept listing, like, not a clue because there's no way to enter that. And it got
Kyle:
Yes. But I only need them to do TPS reports. Exactly. Like, no. No.
Kyle:
No. Wait. Wait. Wait. The value you could bring by unlocking these people is amazing.
Maxine:
All of the marketplace. I was like, you build an internal marketplace from Mitsubishi and let all these people trade their extra skills under your roof with permission. You're not gonna have an exodus. That is the best spot you could be in as majority of humans want, stable paycheck in 20% of time to pour into their passion. That's really stable for nuclear family travel consistency.
Maxine:
You know, only the extremos want, like, full time, like, let me go to the market by myself. You know? But what you're saying is, and this offer that we are co creating that's coming into existence, like, what if I just hired someone based on, I'm like, Kyle, you've run a startup, you quit your job, you've designed a product, you spent your own money on something. That's enough for me to be like, let's work together on something. You have enough check.
Maxine:
Right? I just give you permission, and maybe the thing is a podcast. Maybe the thing is an embed on Stacklist. You know? Maybe it's a connection to David from Meetup.
Maxine:
Maybe it's a series of those things, and you're, like, I think that was worth 10 k. And I'm, like, me too. Good doing this.
Kyle:
Yeah.
Maxine:
You know?
Kyle:
Yeah. Totally. Yeah. Yeah. And it's and it's very, like and and whatever the opposite of an S and W is, which is sort of like what?
Kyle:
We made some bullet boy. And dough. Totally. Yes. But, like but but imagine, this this always happens.
Kyle:
Like, how many times have I been in that situation with just, like, Fortune 100 companies where I'm writing an SOW that says, you will abide by these rules and you will hit these guidelines. And then on day 1 in the kickoff, someone goes like, oh, we need to pivot. That's always and all of a sudden, it just sort of changes and, like, falls all and I think, like but having more sort of creative creative flexibility and also not being sort of hemmed in by the outcome and and actually, you know, unlocking with different skill sets towards potentially different outcomes that you didn't even know of. And then, of course, as a leader, you can say, like, that that doesn't fit right now, but I'm gonna put that on the shelf and, you know, and this is, you know but this is maybe the right time to sort of explore that or whatever. And but I think that creative unlocking in my mind, you know, would would do wonders for, for businesses to to just get outside themselves.
Kyle:
Because so many times, I I did a huge project for a very huge company for the CEO, and everybody I met talked about their own internal department agendas, and not one person talked about the client or, like, what the end goal was of what they were trying to accomplish for the user. And it always baffled me to think, like, everybody's trapped in their own sort of little alternate reality. And if you basically had these reality destroyers come and be like, wait. Wait. I got an idea.
Kyle:
You know? And just sort of, you know, that's what that's that's what I think, like, like, 3 m got so right. Right? It's just like, I don't know. What do you wanna go do?
Kyle:
What do you wanna go try? What do you wanna go? Like, you wanna go work in a glue factory for a little bit because you've never done it and you normally earn account?
Maxine:
Truly.
Kyle:
That's amazing. Yep. So from a marketplace perspective, you started looking at Mitsubishi and then what was the, like, what was the what was the week of or the day of or whenever when you went, like, click? Okay. I got it.
Kyle:
I got I got the the inkling of a of of a thing that turns in to pick my brain.
Maxine:
It was so I on this year, I quit my job as an economist. I gave myself this year on. And this year, I my theory my my hype my thought around this year was, like, okay, Max. You went to university for 7 years and you learned a bunch of things. What if you made up your own university for a year to learn everything you need to learn to transition from economist to founder?
Maxine:
And one of my assignments I gave myself was to have a conversation with a 100 people and to check-in and be like, what are you doing? Why do you love it? What is it like? What are you contributing to? How do you feel?
Maxine:
And if I asked a 100 people those questions, I was like, I'm gonna be really knowledgeable about where people are at, and I'm gonna be able to make a better decision. And I was like, man, 20% through that assignment and being like, it it all those conversations were consistently changing my life. Whether they were introducing me to a new piece of content that wasn't in my radar or on my algorithm, They were introducing me to some person who changed the direction or my ideas about how the world worked or who I was or how to build value. You know, whether they implanted an opinion in my head that built roots and changed how I have opinions in this world in perpetuity forever. I was just like I was having this realization, like, 20% through this assignment.
Maxine:
I was like, conversations are like the new currency. Like, this is more valuable than anything. Like, how and as an economist, I'm trying to value it. I'm like, what is the value of someone Yeah. Heading me down another path.
Maxine:
What is that worth? And at the same time, my mom was retiring. She was a successful entrepreneur as well. And she said something that punched me in the face, and she was like, she didn't know how to share her knowledge or pass it back down. And I was like, I thought about it for a second, I was like, oh my goodness, like, first of all, why is that so hard?
Maxine:
She'd have to make a web site, let people know, figure out a strategy. Like and my mom's at the end of her she just wanna do that. And I remember googling that night how many people were retiring daily. And I was like, where is all of that lived experience going? Where is it in Yeah.
Maxine:
Similar to how we wanted to extract emissions from the sky and carbon capture storage, put it in the ground. I was like, I wanna grab the wisdom and plug it back in the system. Right now, it's just emitting. And that stressed me out enough to be like, I must. And and then I had this other thought.
Maxine:
I was like, well, like, what if my mom could let the world know very easily that she's open and available, and I could have a conversation with anybody? And that was the basis of pick my brain. That was really the foundation. And I was like, well, if Airbnb can take a shared room and list it and let anyone come into it, surely, I can take a shared piece of time. List it and invite the world in, and let's see what happens.
Maxine:
Yeah.
Kyle:
Yeah. Unvisible. I love it. Oh, so so you're like, okay. Now is this the point you buy a domain name?
Maxine:
Yep.
Kyle:
That's the
Maxine:
I I wish I was ever I couldn't come up the name of it. I was calling it human stock exchange for about 6 months. K. I was like
Kyle:
Wait. Yeah. And then a federal agency reaches out and goes, we need to know what you're doing here. Like, this is, this sounds
Maxine:
questions for a while. I called it a small town talk for a while. So I didn't have the name, but the next step that I did was and I'm so happy I knew this intuitively because they train this in entrepreneurship, and it's like test the idea before you build anything. So I full circle, was like, okay, well, like, will people do this? Like, I gotta make sure people are are as crazy as me because I couchsurfed and none of my friends did.
Maxine:
You know? So, like, I gotta make sure that I'm not just obsessed with these conversations. So I made a listing to test it. I had to go be like, alright. Let's see if the world would pay for You know?
Maxine:
Let's see. So I used Airbnb, full circle moment, and that was like, you know, I had quit my job for Airbnb and, like, started to go down this, but they had just launched experiences. Okay. I can go list an experience, but it's not gonna be like a typical experience. It's gonna be a conversation.
Maxine:
And the title of my offer was coffee in conversation with a Vancouver startup founder, and I charged $50. And that was my test. I was like, okay. Well, people pay to pick my brain. I'm a nobody.
Maxine:
Right? I'm a Vancouver
Kyle:
How many people did you think were gonna do it? Like, in your brain, did you think, like, 6, 2
Maxine:
Honestly, I'm like, I don't know, like, why like, yeah. Because I had it for money. If I was, you know, I was really interested, but I was like, I'll just throw it up. But, yeah, like, really low if any. But 60 people ended up booking it in 3 months.
Maxine:
And I said
Kyle:
That's a massive
Maxine:
happy conversation like every other day.
Kyle:
You were caffeinated. I was
Maxine:
captivated, and I was and that was my next realization and discovery on the journey, which is the whole point of it, but it was the I was like, I what I learned was that with a $50 offer, and in my description I said, this is for anybody who wants to talk about the future of work, the future of education, or any idea that you're thinking about with a with a founder that just left her job. That was that was the outcome. And so it attracted like, it was 60 of the 60 experiences were 10 out of 10, and that's very rare. And I was like, why would I have 10 out of 10? It was because the people that wanted to talk about that booked it, and paid me, and showed up on time.
Maxine:
And I wanted to talk about those things, and so, of course, we met. Of course, there was coherence. Of course, there was a jam because we had a set time, 45 minutes together to talk about those three things.
Kyle:
And someone on on the other side had value already in that in that thing. Right? If it was just like stop by at noon, and I'm here if you want to or whatever, but they had value to it. And then you knew you needed to come in and and and give value, and so your your energy was in the right place. And so that's that's
Maxine:
so good. There was elements of that that made that so successful, the description, the price, yeah, book here, here, and this is what we're gonna talk about. And those conversations also fundamentally changed my life. And I'll just give you an example of how change my what I mean by change my life, and I'll just talk about the first three calls of the 60. So the very first person that ended up reaching out was this young woman from Brazil who just immigrated into Canada, won it very entrepreneurial by nature, and she booked it for a birthday present for herself.
Maxine:
And I woah. It was like emotional hit. No. I young woman that's reaching out. She's like, I'm buying this as a birthday gift for myself.
Maxine:
I just wanna talk to another entrepreneur woman. I just immigrated to Vancouver. Anything you can share with me of what you've learned living here or being an entrepreneur, I've opened.
Kyle:
Well, my kids And this Yeah. Like, talk about That's a bug about expanding your world. But Like
Maxine:
Honestly, more than Dave. So she books me, and we have this incredible conversation, and I support her as much as I can. And 2 years later, she ends up working for Pick My Brain and launching Pick My Brain.
Kyle:
Oh my gosh. That's amazing.
Maxine:
I am. And, you know, we'll be in we'll watch each other's lives forever. So that was, like, the first one. The second one, I had a gentleman who was a startup founder who sold a company, Book Me. And I was like, why the heck does he wanna talk to me?
Maxine:
He's so neat. He's like, I love meeting startup founders. I love your offer. I I just sold my startup, and I'm thinking about my next idea. Let's jam about it.
Maxine:
Okay. I can book me, and he ends up writing my first $50,000 investment check. Then even though I was like, there's no fundraising that hadn't even consciously planned it. He's like, I wanna be your first investor. And that set me on to
Kyle:
Talk about signal.
Maxine:
Signal. You know, I was like, okay. I guess I'm a citizen's idea. Yep. Yeah.
Maxine:
I'll have a second call. 1st investor after a 30 minute coffee. K. Fastest, you know, that's not how I love, that's how I expect investment to go. You meet me for 30 minutes and you decide.
Maxine:
You if you look at too much, I'm like, it's I'm over it, you know? Next. Yeah. And that's not to say like I I won't share all my details, but you gotta just know, you know? So that happened.
Maxine:
3rd person that booked me. Also another successful startup founder from the province over from me. He's like, I've got 52 employees, I've raised this much money, I'm scaling my company fast, I'm coming to Vancouver for a Google conference because we're a Google partner, and looking to build my network of entrepreneurs in Vancouver. And again, I'm like, my god. This is be a session for me, not Justin.
Kyle:
Yeah.
Maxine:
We end up falling in love immediately.
Kyle:
Oh my.
Maxine:
And she was my first
Kyle:
3 of 60. How how did the rest of
Maxine:
them go? I gotta write a book about it one day. I truly do. Because I ended up in Pakistan last year because of one of them. I went up to Dubai.
Maxine:
I could go on and on. I won't, but just to signal when I express life changing, because that can feel so like but, like, altering. It is an alt it is a bet in my reality as a result of a 30 to 45 minute deep conversation. And I and and then and so that was, like, my next one of being, like, I am all in. I wanna facilitate 10,000,000 of these between the world's people before they die.
Maxine:
That's my legacy. Yeah.
Kyle:
That is amazing. I I gotta take a second on that. It's just it's just so fun to think about, like, you know, putting that intention out there and then getting such good sort of universe synchronously signal, like, you know, and then and then start and and then you I mean, essentially, when you had that that initial tech, then you had juice to to start putting things together. Right? What was the did you did you start with, like, a a remote team, or did you, like, what was the what was the first sort of v one of of how you guys
Maxine:
started? So I'd say v one was the Airbnb listing for the validation. The v two was my partner. My boyfriend at the time was a developer, and or he was in the we did our masters together, but he took a a 8 week boot camp, and I was like, you need to build the first version to pick my brain.
Kyle:
Nice.
Maxine:
And he did. And we drafted it together. We mocked it up, and I was like, it's gotta be like LinkedIn, but way better because we are not our resumes. Okay? So I really like LinkedIn.
Maxine:
I love Reid Hoffman's story. I love how he created LinkedIn. I think it's a gorgeous platform, but I do think we've graduated. I am not my just work experience. Like, here we are.
Maxine:
Like, I'm a multi potentialite, and I have lots of experiences and travel under my belt that aren't being expressed. So Right. No. Totally. Same concepts, put a book me button on it, and designed it, and onboarded myself and my mom into it, and I started playing with other offers I could make.
Maxine:
So that was version 3, and I used that profile to make my first $100,000 on my own before I started scaling. So I was, like, selling things. So I was like, okay. I made, like, $3,000 selling coffee and conversations. What else can I sell?
Maxine:
And I started selling, like, come visit me for a day and let's build a business for you. I started selling, like, hour long deep dive sessions. I sold a dream out loud call. I sold I just got comfortable using our smart contracts and my just creative cap of being like, what do I wanna sell? What what would I what would I like to repeat that coffee and conversation brought me?
Maxine:
And I just tested it to nth degree, and that was version 4. And then I say version 5 was me taking everything I learned doing that and teaching the first hundred people how to do that. I was like, I'm gonna teach you how to do what I just did. And that was, like, another year.
Kyle:
I love that. Yeah. I'm I'm having a bit of a a moment because I feel like it's one of those that even you just saying this and sort of how you went through the process, I know that there are so many pieces of my brain that I have not sort of I've had so many people tell me, like, I'm usually the one who somebody will text me and be like, I've heard you can help people get set up on password managers, the name or whatever. And just like any I mean, anything anything. Like, between, like, website design and development and, like and and and and getting your, I had someone, pay me once to get the contacts between their phone and their computer.
Kyle:
I'm like, I mean, just all those little things. But I never think about all those. And I've had some people, like, you should set up a Kajabi. You could set like, you should make courses or whatever, and I never I'm always like, yeah. You probably you know, you're right.
Kyle:
I should or whatever. But, like, even just hearing you say this, I'm like, you know what? I gotta I gotta figure out, like, that other you know, it's almost like the side job to Stacklist is is sort of having that, having those conversations of being able to take all the I'm all the multi potential, like, generalist random tech knowledge that I have in my brain and being like, I can share some of that with you. So I totally need
Maxine:
to do that. If you ever wanna book a session, it's one of my greatest gifts is, like, scanning and being like, you could sell this, you could sell this, you can sell this.
Kyle:
Amazing.
Maxine:
What you just said, I actually just told my friend, he's one of those that can come into your house and set up your lights beautifully and your sound beautifully and your Wi Fi and your station, and I'm like, I have no idea how to do that. No interest in doing that, but I will pay you to do that. I want it.
Kyle:
Yes. If anybody wants a Philips Hue home automation setup, I am happy to like, I love doing that stuff. It's just making everything connect and then and then having it timed just right. Oh my gosh.
Maxine:
Zillow a package that was worth your time to that 5,000 and limit it, and email all my best friends, and be like, who wants it? I love doing this. I'm only gonna do 20 of them, and then it's done. And just do one of these side things that you just know how to do, and, like, go buy the equipment and do 20 houses, and make a quick 100 k. And that is, like, what I want to do.
Maxine:
Like, that's an epic offer. Boundary it. Do it at a price point that makes you excited about it. Limit it, and just ask your community if they want it. Stop advertising funnel drip blah.
Maxine:
Your first 100 friends, you know. And if you don't have 100 friends, join our program and meet a 100 friends. You need you need a 100 to be a business owner,
Kyle:
you know. Yeah. Yeah. Exactly. Oh my gosh.
Kyle:
It's so great. So what do you like, you you were you were talking and alluding to it earlier, which I I absolutely love because as you were talking about this, I started thinking about the sharing of your knowledge that you were talking about with your mom. And I think about the same thing with, you know, my granddad who lived to, of just shy of a 100 and, you know, and went through the war and, like, was, I worked at AT and T doing, doing all sorts of, telephony and things like that. And and to be able to sort of take that stuff and and give it to someone, which, you know, makes me think of the kids and sort of how you get that stuff to you know, I almost think how how cool would it be if there was a version where I could also, like, have my son as alt as an alternate add on to school, like, have someone once a week or or, you know, or twice a week for 30 minutes in a completely random sort of different, you know, career. And and if you did that for years years years years, you're gonna get a totally different 15, 16, 18 year old than you do with the one who is completely focused on the 10 mile radius around their house and, like, the fact that they love Legos and cars.
Kyle:
And, you know, and it's just that versus, like, talking to someone who built a construction company and talking to somebody who sort of works on satellites or like, you would you would immediately expand that child's mind into, you know, infinite possibility, which is amazing.
Maxine:
Well, it is exactly what we're working on in the public education system right now, and it's prolific how you just thought about it. Because you said the difference between the transformation that would occur between 2 kids that are the same age, one being introduced to a different career every week of their life until they graduate, and one not. K. And right now, the school system that does not introduce you to another career professional. And I pitch one of our projects at Pick My Brain using our marketplace technology is to facilitate 1,000,000 career talks being embedded into the classrooms.
Maxine:
We're gonna start in the classroom first, where a teacher commits to going to a database of vetted professional marketplace and booking any kind of professional that they want to just come share their story with the kids. Full stop. Let them ask some questions. It's not part of the program. What you just also got me thinking about is building a meet the world's people subscription for kids that parents can buy their kids and be like, would you like us to get your kid to stock?
Maxine:
I know they're young. If they're age 5 to 10, do 10 minute talks with whoever they want. If they're age this, do 30 minutes. If they're age this, do 60.
Kyle:
Go away. We can we can POC this with my son. So basically, he's on Duolingo. He he's got my brain, so he already like, he he just turned 8. He's got a MacBook Air.
Kyle:
He's on there playing he's on there playing a farming simulator, and he's like, I just brought the crops in. I need to go sell it so that I can get my Ford F150, and, like, he's doing all the things. But, like but he started doing Duolingo. And the gamification of it is the thing that be basically, he's like, I'm at the Ruby level, and I'm on a 30 day streak. And now all he talks about is his 30 day streak, and he's learning French.
Kyle:
And and, basically, he's in there sort of doing he's in there sort of, like, competing against other people, and it's getting a little bit harder. And then he's like, can I just, like, can I stay up a little bit longer? Because I need to make sure that I get to the 3rd level so that I don't get bumped and demoted down or whatever. But the problem is is that I say, like, I love this one thing, but I feel like we have this one thing. Like, if I if I think about we have, what the the store parental controls on or whatever.
Kyle:
But, like, I would love to be able to say, you have this and you have this other thing. You can do it as much as you want to. You know, like, the games will turn off and the YouTube and the videos will turn off, but you can do these other things as much as you want to. Brilliant. And to be able to sort of, like, I met a dentist today or, you know, I met someone who who builds rocket ships today.
Kyle:
It's so interesting that I think when you when you think about a child's mind of I wanna be a fireman, I wanna be a policeman, usually, it's the sort of archetype of, like, the the toy on the on the cartoon or the whatever. But to be able to sit and talk to someone that's like a data scientist or that, like, you know, builds things or, like, builds skyscrapers or, like, you could you could see it immediately sort of create this, like, oh, wait. I actually talked to someone who did that. Like
Maxine:
Correct. And you you're I would love to test, like so there's 2 things that we're we're gonna pilot here with partnership. Another just like the school one. There's would you be interested as a parent for your kid to talk to other 8 year olds around the world, career professionals around the world, or people just above his age that are change makers, like 15 to 16 year olds that are around the world doing some really cool stuff. And, like, tell me the categories.
Maxine:
I can get that specific with him, you know. And and I and I do I this is a subscription in the making. How can we get and and I want people to subscribe to this as well. I really want the planet to be like, meet 1 person a month. Start there.
Maxine:
Please, for the love of life, pick meet 1 stranger and inquire about their life, and Pick Librarian will set that
Kyle:
for you. We will match you with 1 unique person a month,
Maxine:
but we need you to commit to meeting the world's people. And then bring it down to your kid too. Parents, please plug your kids in because this is the most important thing. If they're too plugged into this and not enough in this, you know, we need to keep the human balance as much as we plug into this equal. Yin and Yang, both are great.
Maxine:
You know? But, yeah, like
Kyle:
And expand expanding the world and also and also collapsing the world in what's possible. When you think about how how it used to be, you know, in the 40 thirties, forties, 50, sixties, the people who could travel to France, to Egypt, you know, and those sort of things. And now it's, like, it's better. I mean, still cost you $5,
Maxine:
so,
Kyle:
like, to fly out there. But but we're, like but to be able to compress the world and talk to almost anybody and sort of learn that knowledge from someone and to start it at such a young age, I think, also would come back. I remembered part of the reason that I want my my boys to sort of we wanna live outside the US for for a while is to give that, like, other perspective so that because sometimes I think there's, I mean, there's a lot of goodness here, but there's also a lot of, you know, Kool Aid and you get in the matrix again just like you do with work or friends or school or whatever. And so living and get it getting a different perspective from somewhere, you know, I say I I remember very distinctly before we had the boys that I saw this Time Magazine article about how, like, teenage suicide was up in rural America and in in schools and things like that. And the first thing that I thought of is is a lot of times, like, that being just such as, like, the world the size of the world is so small that it's like it is what you think is possible and what your, you know, what your your sort of network is is is sort of in this place that being able to sort of potentially how many people could it help to be able to expand your world and go, oh, I don't have to think that this is how things have to be because I met this other person, this other person, this other person, and you start to expand out a bit.
Kyle:
Could just help from a mental health or or world perspective or, you know, change the perspective of someone's trajectory.
Maxine:
I think I think if the world, if I could get a 1000000 people to commit to meeting 10 people a year, oh, the shift. And it's so simple. It's the simplest thing to do, but it does. It expands your awareness, your perspective, your idea of self, your idea of others, how to integrate, how to collaborate, how oh, 3 years ago, I I'm like, oh, I met that person 3 years ago. I'm gonna call them because we had a deep connection, and I can.
Maxine:
But, like, it is a lifeline. It is social security. It is staying somewhere. I got in New York, lost my passport. Oh, just call my network.
Maxine:
Going to pick my brain. Hey. I'm in New York. Hi. Hey.
Maxine:
You know?
Kyle:
Totally. Who's the
Maxine:
It is, it is the one of the most, one of the greatest investments that everyone can make is 10 10 conversations, deep conversations a year with different people outside of your algorithm. You gotta hop off because you know you know your algorithm.
Kyle:
I I know. Yeah. Yeah. I love it. I love I love what you're what you've built and and where it's headed because, it's it's amazing to to think about, you know, building something that's so powerful and and can be so transformative for so many people, but then to also expand that out what feels like 2 or 3 times in in different directions, for, you know, for for both kids, and for for different types of of individuals globally is is amazing and for the workforce.
Kyle:
It's so great. Yeah. So
Maxine:
I'll send you forward. You're gonna just say someone I've learned about you from day. I'm like, cool. I'll give you some more. Just whatever you need them because those
Kyle:
Let's do it. Let's do it. I know. Well, we we have to we we definitely have to, like, figure out some sort of monthly, like okay. Ready?
Kyle:
And and we just, like, record it and we just hit it and we're like, okay. We're yeah. What do you just like and have the ping pong balls just, like, bounce around and they come away. I'm like, okay. We just but, like, there's, like, 5 ideas.
Kyle:
There's, like, 2 business days. So so
Maxine:
No worries. I'm not. And now I'm just, like, designing a program in my head, meet the world entrepreneurs. We will set you up with 1 entrepreneur a month. You can decide which ones you wanna keep cadence with.
Maxine:
But these people you can talk to, these are people you can spit ideas at. Entrepreneurs are a different speed. And in the it's like we require one another to stay on, you know, it's it's so essential. That's therapy to me meeting with you monthly. That's like grounding, you know?
Maxine:
Yeah. So, I'd so be
Kyle:
I love that entrepreneur sign too, especially for for for startups in this, you know, in this phase that I'm at of this sort of 0ed is also this room. But sometimes this room do you know what I mean? Like, it is comfortable, but it's also it gets small. And that's why I mean, I love traveling. It's hard I mean, it's hard being away from the boys and from from from my wife, but, like, it is one of those that, like, it it's so different because you get so many different perspectives and that energy of just, like, creating and making and things like that.
Kyle:
And so, you know, it's you're right. And and I'm gonna I'm gonna I'm gonna go back and and flesh out my pick my brain and and and then try I'm just gonna set up my next 3 and and see what what comes from that. Cool. This is this is amazing. Well, thank you so much for for taking the time, especially coming flying literally right back in and just, like, right into the hot seat and be like, tell me about your life.
Maxine:
Thank you for grounding me. Thank you. I can't tell you how many ideas I got from this session by, like, just jamming. So I'm totally down for the monthly. I'm totally down to just keep clapping.
Maxine:
I'm excited to support your Pick My Brain profile and your introductions to other people. I totally am gonna invite you to meet the world's people as soon as I launch it, which will be in the next month. I totally wanna put a package together for your 8 year old to test it, you and I, just to see. There's a lot more on the table, and, of course, we have the mergers of our platforms.
Kyle:
Yeah. Yeah. Amazing. Well and I and I challenge anybody who's who's listening to to go go to Pick My Brain, like, and sign up and and get get time on Max's calendar or, or Perry's doctor Octopus. Just look up doctor Octopus.
Kyle:
Yeah. You're gonna have the best conversation. So amazing. Well, thank you again, and, I can't wait to talk to
Maxine:
you soon. Look forward to it.

Maxine Cunningham
Founder & CEO
CEO & Founder at Pick My Brain | Marketplace Architect | Facilitator of Global Knowledge Exchange | Creator of Education & Professional Marketplaces