How Curiosity Fuels Business Growth and Leadership With Alana Winter

John Corcoran: 11:59

Entities. Separate.

John Corcoran: 12:00

Okay. No, no. Like the business reason behind it really. But more of a legal reason. Okay. Got it. And did you stay in this? I don’t know if you got out of the business before everything started to change the market classically, you know. You know, I actually had the co-founder of Netflix on my podcast a while back. You know, Netflix movies. Blockbuster is no longer. There’s one left in Bend, Oregon. I’ve been to it. And so were you still in the business when things started to change?

Alana Winter: 12:29

I was still in the business, but a couple of things happened. One is I had worked really hard to open up accounts and supply public libraries and believe it or not, public libraries still carry DVDs and.

John Corcoran: 12:44

Yeah, they do.

Alana Winter: 12:45

Yeah. So that actually was a great business selling to libraries, their wonderful customers. I love libraries. I actually love hanging out with librarians. I love books, so it was really fun. So I had taken in a business partner. I had a whole business partner disaster. But we did wind up selling the business. But that business actually would still be viable just working with libraries.

John Corcoran: 13:10

Got it. Tell me about the business partner. What happened there?

Alana Winter: 13:16

I took in a business partner to run the day to day operations of the business. Who was a competitor who also did the same thing that I did. Did overstock and did resale and distribution liquidations, all that stuff. And we’d known each other for a really long time, and we set up what seemed like a terrific business model to me.

John Corcoran: 13:38

And let’s pause right there. So why at the time that you decided to partner up with a competitor? Why? What was the motivation behind it?

Alana Winter: 13:50

It is a major life lesson. I had gone into this business because it was a great opportunity that was there for me. It was very profitable. It was a great time in the market. The business had nothing to do with who I was or what I valued. My, you know, anything that I wanted to bring into the world, it was just an opportunity. And businesses get hard. And when businesses get hard and they’re not tied to the core of who you are, it becomes a real slog.

And there were days that I woke up in the morning and I pulled the covers over my head, and I did not want to get out of bed to go into my office and run this business that I had run. Right. It was just so it was hard. It was a slog. and I had tried everything under the sun to spark my interest, and I would try creative marketing stuff. I went on a kick where I was. I was hiring young single mothers from. There were some bad areas around my neighborhood in Passaic and areas like that and, you know, to create social programs.

John Corcoran: 15:00

But all of those were kind of initiatives that were good to do for the broader community. But it sounds like they were also you were also doing them to try and find a way that you could rediscover some kind of spark or passion for your own business.

Alana Winter: 15:16

I was trying to find a purpose and meaning for the business. Absolutely. And I had run out of rabbits to pull out of the hat.

John Corcoran: 15:24

Yeah.

Alana Winter: 15:27

And, you know, I had close relationships with some of my competitors. And, you know, we would discuss how we felt about our businesses. And so this one competitor, he said, well, you know what? I’ve got excess capacity in terms of his warehouse space, his staff and all that kind of stuff. And we had some meetings and we came up with a business structure where he would run the business, run all the day to day logistics of it, everything, all operations would be moved into his facility.

And because I had established business with the libraries, which was really hard to get and was really steady, and they were great clients, they weren’t going bankrupt. They weren’t closing like stores where they always paid their bills. They were wonderful to work with. They’re hard to get as clients, but wonderful to work with once you do get them as clients. And we would do a 5050 split of the profit. So he would pay out of his share of the profit, all of the operating costs. I would have zero operating costs but get 50% of the gross profit.

John Corcoran: 16:34

Great Deal. Yeah, so.

Alana Winter: 16:37

That’s why I did it.

John Corcoran: 16:39

So at what point did you notice that this may not be meant for the long haul?

Alana Winter: 16:47

This is a funny story. I called the bank for something and to check on something in the account, and the bank asked me. We had the name of our company in the. And the bank asked me which account, and we had only opened one account. And as soon as the bank asked me, this is back in the old days, when you called, you knew your local branch and talked to the teller.

John Corcoran: 17:14

Yeah.

Alana Winter: 17:15

And as soon as the teller asked me which account, I knew instantly that meant he had opened up another account. And the only reason he would have opened up another.

John Corcoran: 17:23

Account to hide money, because.

Alana Winter: 17:25

He checks into it.

John Corcoran: 17:26

And. And there must have been something else that caused you to instantly know that something was awry.

Alana Winter: 17:35

You’re right. Back up. Right. That’s why I called the bank. Totally forgot about this. Because I was living overseas and I would call him. I’d come in once a month and we’d have meetings. And I called him to set up a meeting, and he was always in the office, so I could just call anytime, be like, hey, I’ll come in on Tuesday. And it was a Friday. And I called him and said, I’ll be in on Tuesday. And he stuttered and stammered a little bit and he said, oh, I’m not sure I’ll be here on Tuesday. And I knew from that difference in the tone of his voice.

John Corcoran: 18:07

Something was up.

Alana Winter: 18:08

Something was up.

John Corcoran: 18:09

Yeah, yeah, yeah.

Alana Winter: 18:10

That’s actually why I called the bank.

John Corcoran: 18:12

So what did you find out? There must have been money missing.

Alana Winter: 18:16

There were indeed two accounts. So when the teller said which account? I said, oh, you know what? Silly me. Right? Of course. Could you just fax me over the statements for both of those? And so I looked at the statements and I realized there were checks going into this other account that were not showing up on our books. Then I, you know, went in electronically to the records, and those checks were not showing up in our accounts.

John Corcoran: 18:46

So I realized.

Alana Winter: 18:47

What was going on? I went and actually physically visited some of those customers because I had the records of checks that they had paid and, you know, just very homey and folksy. Bring a box of donuts. I just wanted to go over your account and how we’re servicing you and what you’re getting from us and collect evidence from those clients.

John Corcoran: 19:09

And then. Wow. So you I mean, there’s a lot of people who would immediately confront their business partner, but it sounds like you took your time to investigate it further. That requires a lot. I mean, a high level of patience.

Alana Winter: 19:25

Well. You know, as you mentioned, one of my businesses, MI6 Academy in Stiletto Spy School Cool.

John Corcoran: 19:31

Now I know the inspiration.

Alana Winter: 19:34

It totally was right. And so I had learned from, you know, those. So those programs are fun fantasy adventures. Come and be James or Jane Bond for a day, but they’re super practical takeaways to these lessons, right? And it’s about how you use the mindset of the spies and special ops to get ahead in business.

And one of the really key lessons from that is being able to see what’s actually going on around you. We tend to as humans, we get a little bit of information and we based on that, a little bit of information, we jump and then we miss so much other stuff. So I had learned from the instructors at Spy School that when there’s something out of the ordinary, you need to pay attention to that, because that is either a threat or an opportunity. So I heard my business partner’s tone of voice change. Oh, something’s out of the ordinary.

My alert went up. That’s either a threat or an opportunity. And what you learn is that when you sense there’s either of those, you don’t blow it up. You investigate to see what’s going on. So it was completely the lessons from spy school that kicked in and that saved me. And that’s why when he reacted that way on the phone, I didn’t automatically say to him, what are you talking about? What’s going on? I heard it, and I just said, oh, okay. Well, you let me know when it’s good. But I knew that I had to investigate, so I investigated. And again, normally what we do is when I found that from the bank, normally what we do is go into explosion mode, right. But that doesn’t serve us very well.

Alana Winter: 21:18

No, no. Also, I had learned from my instructors. Okay, you have to now. Now that I knew I’d been hit. Right. If I’m going to take it to actually the allegory of what we’re learning at Spy School, right? In hand-to-hand combat. You’ve been hit. You don’t fall to pieces on the ground. You go, okay, I’ve been hit. What are my opportunities? What opportunities do I have? What targets can I hit?

John Corcoran: 21:41

And so so you mentioned you learn from your instructors at Spy School, but you’re. I thought Spy School came later. Had, you know, you had already started this spy school. So you already had this business. Coincidentally, when this fraud happened. And so do you. Oh, interesting. So you have. And you learned from your own instructors on how to handle this situation?

Alana Winter: 22:07

Yeah, as I’d been doing training with them before I even launched the program to the public, right. As I’d been investigating and doing training with them. These were the lessons from things like hand-to-hand combat. These were the direct lessons that I learned there that I applied into the business.

John Corcoran: 22:23

How long did you continue to investigate before you confronted your business partner? And how much did you find out was missing?

Alana Winter: 22:31

Oh, it was days. So it was I think it was a Friday that there was that phone call and I called the bank right away, and I got the records from the bank, and I went through them all weekend. And by Monday morning, first thing Monday morning, I was sitting with clients and I spent Monday. I spent all day on Monday gathering all the evidence that I needed. And I went to the police and to the DA. And by Tuesday he was being served with papers and I was sitting. I walked right past him. He hadn’t noticed me walking in. I’d walked right past him, and I was sitting at a desk in the back and sitting at the computer, just downloading files and files and files. And he was being served with papers.

John Corcoran: 23:19

Wow. What was that like emotionally, this period of time for you?

Alana Winter: 23:23

You know, it’s interesting. And again, these were lessons from spy school I had in the past. I had two cases of employee theft before this.

John Corcoran: 23:32

Really? Okay.

Alana Winter: 23:33

Yeah, I had a bookkeeper who embezzled. She took out a line of credit for me.

John Corcoran: 23:37

Name is crazy.

Alana Winter: 23:39

And I had another employee who had come in and cleaned out the warehouse. Again, crazy stuff. And in both of those instances, John, I had this. Really. Incredible emotional volcano inside, right? It was this visceral, like just seeing red. And, I mean, I remember crying and calling them and yelling and this very, very strong emotional reaction. And in this case, and again, this was the lessons that I was learning that are the basis of what the spy school programs were about. You know, you don’t if a Navy Seal is driving his tank and an explosive device goes off. He doesn’t crumble. Right? Right. Yeah.

John Corcoran: 24:27

No, it wouldn’t be the best reaction.

Alana Winter: 24:30

Yeah. Right, right. Like, they don’t have an emotional reaction. It’s just something that happened. And you have to figure out what your best response to it is.

Alana Winter: 24:37

Yeah. So when this happened and I saw this, like, the volcano started for a nanosecond.

John Corcoran: 24:45

And what. You pushed it back down.

Alana Winter: 24:48

Yeah, but I didn’t like it’s not. Like suppressing it. It was like this. Actually, it’s not even appropriate for this situation. Like, this is somebody. My business partner was somebody he. You know, as it turned out, he was under financial pressure. He made some terrible choices that got him into financial pressures. And then he made terrible choices. Seeing an opportunity to embezzle and steal from me, those were really, really bad life choices. And I was not going to sit back and let it happen. I was going to stop him and. But I didn’t like getting emotional about it. Just.

Alana Winter: 25:26

Yeah, really. Didn’t serve like it wasn’t personal. And so taking it personally just didn’t serve. But I didn’t see that before. Of course this was new.

John Corcoran: 25:35

Yeah. So was it the two previous employee thefts that had inspired you to start the stiletto spy school? Like I’m curious, where’s the natural curiosity that predates this business partner who defrauded you?

Alana Winter: 25:49

Yeah. So just as a kid, I watched too many James Bond movies with my dad, and I figured, like, one day I’m going to grow up and I’m going to be like the bond girls. This is a girl who never learned how to ride a bicycle. Can’t roller.

John Corcoran: 25:59

Skate. Like, never learned how to.

Alana Winter: 26:00

Do anything at all. So I was like, but I will be cool like them. One day I will grow up. I will go to the school that they go to because obviously there is a school to learn to be that cool and that confident. How are those skills?

John Corcoran: 26:15

So all right, so you react with composure. You gather all the evidence, you go in, even into the office, download all the data. He’s served with papers. What happens from there? How do you rebuild your life? How do you deal with it? I mean, I’ve seen this happen with others where, you know, simultaneously a business partner, a past client, whatever is being prosecuted is going to jail. They have to deal with that. But they have to put the business back together. So what did you do?

Alana Winter: 26:49

Yeah. It was a journey, you know, I mean, we went through a legal process, which takes a really long time, even when you are in the right and somebody else is clearly as guilty as could be. That was probably about two years. And at that time, I was really reflecting on what was next for me and what I wanted to do next. And so I had started studying hand to hand combat, and I had this kind of idea, but it was vague. I’m big.

I didn’t like there weren’t any programs for the public or anything at all during that time. And what I realized was that whatever I did next had to be not just because it was a good business opportunity and that I didn’t have my heart in it, but it had to be something that I would love, even when times got hard and that it really meant something to me. And what I wanted to bring into the world. So I went on a quest to discover, like, what my true core values were and what that would mean and what that would look like. And I couldn’t find any programs out there. I went to a bunch of them, but I found that most programs that I went to and it’s like, find your core values. You just hand you a sheet of paper and they’re like, pick, pick off of this list. Write, write it out.

John Corcoran: 28:07

Yeah.

Alana Winter: 28:08

You know, and when I did that and I don’t want to diss people who run workshops like that, it’s just that there’s so much that we’re conditioned to that we’re that. When I looked at that list and I circled all these words on a list, I knew that I was circling words that I had been conditioned to think should be my core values. And I knew that there was a deeper question as to what was really me. What was I here to do in this life as opposed to what had I just inherited? So again, like with Spy School, I couldn’t find the school. I couldn’t find the process to help me figure that out. So that’s what I did my deep search on, and that’s what I built, which then became the essence of the coaching work that I do with people.

John Corcoran: 29:01

And were you in an entrepreneurs organization when the business partner defrauded you and what role did that play or what did your forum play in helping you through that period of time?

Alana Winter: 29:17

You know, it’s interesting. One role that my forum played, sort of that set the stage for it when I was taking in this business partner at a couple of forum mates who had done businesses that were like that with a similar kind of structure, and they reviewed my contract and they suggested putting in a clause in the contract that if there was any financial misdoing and they told me I had to be specific and put a dollar value on it. And I put in over $1,000 that I could sue him personally, because when we created a business together we both had LLCs and so our respective LLCs were the partners in this new business. So they said if there was any financial fraud, if I sued him, he would just as if I sued the LLC Collapse’s LLC.

John Corcoran: 30:09

Yeah.

Alana Winter: 30:11

They say that you can sue him personally. So I put that phrase in that closet, and my own attorney said, we can’t put that in. It’ll never pass. And I went back and forth. My own attorney, who I was paying, sent me three versions of the contract without.

Alana Winter: 30:27

It is. Right until I finally, like, lost it on him. And he’s like, okay, okay. And he put it in and we got to the signing and at signing my business partner ‘s attorney says we can’t allow this clause. You can sue him personally. And so I said, oh can I talk to you in the hall.

So we went out in the hallway and I said, listen, just tell me now, do you plan on embezzling or committing fraud? And he said, no, of course not. I said, well, then do you have any problem with putting this clause in? And he said, no, I guess not. So we went back in and he told his attorney to leave the clause in. So because that clause was in there, I was able to sue him personally.

John Corcoran: 31:04

Wow.

Alana Winter: 31:05

So that was invaluable help from my forum that I never would have gotten. My attorney certainly would. Never in a million years have suggested that.

John Corcoran: 31:14

Yeah.

Alana Winter: 31:16

Yeah. When. But you know, it’s funny when. So a couple of things though when this happened, some support that I did get. You know, people just helped me understand a little bit and said, you know, just think about it.

They made me sit down and think about what I wanted to get out of the court process, but also when this was happening I was really glad to share this on this podcast, because there might be others out there. I actually withdrew when that was happening.

John Corcoran: 31:52

It’s not uncommon for people to do that. You know, there may be I don’t want to put words in your mouth, but there could be shame. There could be a lot of different emotions going through.

Alana Winter: 32:01

And I also think there was a belief that I should handle this by myself. I should be able to handle it by myself. And I think that’s a really common thing that people have also is I can’t ask for help. I should know this. I should be able to handle this myself.

John Corcoran: 32:20

Yeah. So looking back on it now, how would you have done things differently with that insight?

Alana Winter: 32:27

Yeah, I would have. I probably would have leaned out for a lot more support. I mean, I felt okay with it. With going through. I mean, I truly never had an emotional reaction. Like, I still don’t really feel anger towards him. I mean, it really sucks what happened. It totally sucks. I had this business I had built up for a really long time. You know, so much of the value of that business was destroyed because of his actions.

So much of my time was taken up. But I actually have just a perspective on it that I think I got from that whole thing of spy school. Like things just happen and you deal with what happens. But after, you know, afterwards, I think it would have been really helpful to reach out and connect with people as I was going through the rebuilding of my life and I didn’t, I really I really struggled through that on my own.

John Corcoran: 33:27

Let’s talk about what we said at the beginning, we talked about leading with curiosity. You know, you demonstrated some curiosity when you called the bank and they said, there are two accounts. Oh, you know, that’s natural curiosity, right? And then you went to the clients and you talked to them and led with curiosity. Let’s talk a little bit about that idea, how leaders can leverage it beyond just hopefully beyond just when you’re being defrauded, but in other instances as well.

Alana Winter: 33:59

You know, John, it’s such a rich topic and it is such a challenge for most of us because we go through life trying to be efficient and we have enormous, incredible to do lists in trying to get through everything on it. And so it is efficient to categorize things and to reach conclusions and to make decisions quickly. But in doing that, we miss so much information. And missed information is the same as getting misinformation. And so whether that is on the 1 to 1 level, when we’re dealing, we’re having a 1 to 1 conversation.

And I want you to think about how that could be a 1 to 1 conversation with a loved one, with your child, with your spouse, with a key team member, with a client. And as we’re listening to them, we’re thinking about what we’re going to say next. We’re thinking about what they’re saying, and we’re figuring out if it makes sense. We’re figuring out. Do we agree with it?

Do we not agree with it? But in doing that, we’re missing so many cues that they’re giving us. And so one of the key things and I learned this, you know, we’re in EO, we’re taught in the forum right. That you’re supposed to when you’re listening to people giving their 5% reflections or giving their presentation to really listen to everything they’re saying. But we’re not what we’re thinking at that time.

So I try to be a forum trainer and then work with forums, right, trying to teach that. And I will say I learned that skill from my spy school experts. I learned that skill from the CIA and the FBI, experts in deception detection. When they’re working with somebody and they’re trying to figure out what’s going on and get the truth out of somebody. I thought, oh, they’ve got these super analytical minds and they’re curious.

John Corcoran: 36:03

Yeah, totally. Yeah.

Alana Winter: 36:05

They have a totally quiet mind.

John Corcoran: 36:09

Yeah. Yeah. And I can verify that because, you know, I worked in the Clinton White House, so I went through an FBI background check and they came out and interviewed me and asked me questions about my background, high school, college, stuff like that. One moment of levity was they were asking me about, like, college or something, you know, which I went to a party school. So let me just leave that there.

And, you know, they’re asking like, what was it like? And I, I’d been advised, like, just lay it all out there. That’s the worst thing you can do is just not tell them about something. So I was like, you know, my college, we were kind of having a party house. We’d have parties kind of frequently, and people would come over and we had kegs and people would drink from it and stuff like that.

And I remember one of them, an FBI agent, looks at me and he says, did you have a drinking problem in college? And I wanted to say, didn’t everybody? I mean, you know, but I didn’t. But yeah, but, you know, their natural curiosity, like, they just would kind of follow through and ask you to ask you about different things around your background.

Alana Winter: 37:06

Yeah. And you probably experienced them too. Then when you finished speaking, they probably wouldn’t jump right in with the next question. They would probably pause for a minute before the next question.

John Corcoran: 37:18

Yeah. Yeah. Wait and see if something else comes out. Because sometimes that Dead Space people will want to fill it and you get some good information out of them.

Alana Winter: 37:27

It’s two things. Absolutely. You let that space sit for a second. But also, if you haven’t been thinking about what you’re going to say while the person’s talking, there will be a pause because you’re taking in what they are saying.

John Corcoran: 37:40

Said.

Alana Winter: 37:40

And then you’re responding to it.

John Corcoran: 37:43

Yeah.

Alana Winter: 37:43

And it was such a learning experience for me. And also when they get a really quiet mind and they just put all of their focus and attention on you, that’s when you can notice the difference in somebody’s voice, the difference in their expression, the difference in their body language. But it’s about taking that time and that curiosity to instead of jumping to a conclusion or filling in what you’re going to say or filling in your mind what you think they’re going to say next. Yeah, really being present.

John Corcoran: 38:14

I’m curious. So I worked for the last law firm I worked for before I went on my own, became an entrepreneur, and was actually embezzled. And the woman that I was the controller had taken over $1 million over many years. And they discovered this about six months after I left. And I know that the managing partner, like, marched in with the proof and confronted her about it.

There wasn’t a lot of thought. I think that went into that, that experience. But, you know, with your business partner, looking back on it now, I don’t know if the lawyers that you were working with advised you against that. But given what you’ve just said about curiosity, do you think that that would have been one approach to take? If you’d had the emotional control to do it, to go into the business partner and see with natural curiosity and see what information you could have gotten out of him.

Alana Winter: 39:09

As you know, at that point, I got the information from the bank and I got information from our clients, and I had all of the company records. And, you know, I mean, he.

John Corcoran: 39:24

Had what he needed. He made a few.

Alana Winter: 39:26

Mistakes because he was all of the records. When I typed into the company system, there were all of our records, but they were also all of his company records and the records from where he was funneling the money. So I had to.

John Corcoran: 39:41

Get all that, all all of that evidence. Right.

Alana Winter: 39:45

I mean, I certainly could have had a conversation with him about why he did it. But to tell you the truth, I didn’t really care.

John Corcoran: 39:51

Like, I knew it was just a bad decision. You know, I.

Alana Winter: 39:53

Knew I could see that his original company was there. Sales were falling off in his original company, so I knew he was under financial strain.

John Corcoran: 40:01

Yeah. So I mean, frequently lawyers will say not to do something like that because they don’t want to risk compromising some other evidence that might come in. So talk a little bit more about some of that work that you do now with forums and with business leaders. Tapping into that curiosity and how they can leverage that, especially now we’re recording this at the end of 2024, on the cusp of 2025. And AI is a big tool that everyone’s talking about.

I know you just did a presentation actually to a group about that. So talk a little bit about how business leaders, entrepreneurs can tap into their natural curiosity as this really disruptive technology is coming right down the pike.

Alana Winter: 40:42

I think the most important thing is to recognize our discomfort. What gets in the way of curiosity? A couple of things get in the way of curiosity. One is judgment. Seriously, you can’t, like, hold judgment and curiosity at the same time.

And the other thing that gets in the way of curiosity is discomfort with uncertainty, right? Because curiosity is uncertainty, and we very much want to know what’s going on. And you talk about AI, and for a lot of people that is scary because it is unknown. And they can’t figure it out. It’s just so rather than getting curious about it, the fear has kicked in because of that discomfort with uncertainty.

And so when the fear kicks in, the curiosity shuts down. So the most important thing is that mindset. And recognizing that and recognizing that as long as we let fear dominate. Right. Fear kicks off everything from the base from our limbic system, the very primitive base of our brain.

And we go into a state of it’s called amygdala hijack. And when you’re in that state, your prefrontal cortex shuts down and your prefrontal cortex is where reasoning is. And language. And collaboration and creativity. So you don’t have access to that when you’re in a fear state.

So I think the most important thing for entrepreneurs and for everyone right now, with the changes that we’re facing with AI, is to recognize that fear and that if we stay in that, we will not be able to function and to find ways to get curious and start to learn. And, you know. And so some of the work that I do with forums, because the communication like curiosity improves communication, right? It’s like what helps us build bridges instead of building walls when I’m actually naturally curious about you, as opposed to judging anything that I think about you, you feel safe or you feel more open, we have a more authentic dialogue.

John Corcoran: 42:57

Yeah. Well, I mean, as someone who is endlessly curious about so many different topics, this totally resonates with me. And I love this idea. I know we’re almost out of time. So Alana, I want to thank you for all of your time here today. Where can people go to learn more about you and connect with you?

Alana Winter: 43:15

My website is alanawinter.com. Easy. And if they want to learn about Spy School, there’s stilettospyschool.com and mi6academy.com.

John Corcoran: 43:24

Yeah.

John Corcoran: 43:24

Go check out those websites. Really cool. And EO and YPO forums and other types of forums can reach out to you about different forum transformations. And I know that you got rave reviews when you came out here to San Francisco. So Alana, thank you so much for your time.

Alana Winter: 43:37

Pleasure, John. Thank you.

Outro: 43:41

Thanks for listening to the Smart Business Revolution Podcast. We’ll see you again next time and be sure to click subscribe to get future episodes.