Alana Winter is a serial entrepreneur, creative thinker, and President of Transformative Forum, where she leads retreats, workshops, and one-on-one training to transform business leaders and their teams. She has built and operated several successful ventures, including a fashion accessories company in Australia, three video distribution companies in the United States, and the MI6 Academy and Stiletto Spy School. Recognized for her leadership work with EO and YPO forums, Alana’s innovative programs have been featured on NPR, The Today Show, CBS Morning News, the Wall Street Journal, and more. With a BA in psychology from Wesleyan University and a knack for helping others overcome roadblocks, she inspires leaders to approach challenges with creativity, clarity, and confidence.
Here’s a Glimpse of What You’ll Hear:
- [2:14] How Alana Winter sold a box of scraps to a neighbor at age four
- [8:23] Why Alana’s father fired her for being five minutes late to open the store
- [13:51] The motivation behind partnering with a competitor
- [16:47] How Alana discovered her business partner was embezzling money
- [19:34] Applying lessons from Spy School to uncover fraud
- [25:49] How the Spy School program teaches practical skills for handling business challenges
- [28:08] The importance of finding a business that aligns with your core values
- [29:17] What role did the EO forum play in dealing with the fraud?
- [33:59] How curiosity and active listening can transform leadership and communication
- [40:42] Tackling fear of AI and embracing curiosity to navigate technological disruption
In this episode…
Many leaders struggle with finding purpose and resilience in their professional journeys, especially when faced with unexpected challenges. From burnout and business betrayal to adapting to new technologies, the path to success can feel overwhelming and uncertain. So, how does one transform simple inquisitiveness into a powerful leadership tool?
Alana Winter, a serial entrepreneur, shares her insights on transforming adversity into opportunity. Drawing from her experience in building businesses, uncovering fraud, and creating unique programs like MI6 Academy and Stiletto Spy School, Alana emphasizes the importance of curiosity and emotional control. She encourages leaders to focus on clear-headed decision-making, embrace discomfort as a growth opportunity, and actively listen to uncover deeper conversation insights. By approaching problems with a calm mindset and a sense of purpose, Alana demonstrates how curiosity can unlock meaningful connections and drive lasting growth.
Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Alana Winter, President of Transformative Forum, about the power of curiosity in leadership and business growth. Alana recounts her journey as a young entrepreneur, her lessons from spy-inspired programs, and her strategies for maintaining composure during crises. She also emphasizes the significance of building authentic relationships through curiosity, which can lead to better communication and collaboration.
Resources mentioned in this episode:
- John Corcoran on LinkedIn
- Rise25
- Alana Winter: LinkedIn | Website
- Stiletto Spy School
- MI6 Academy
Related episode(s):
Quotable Moments:
- “It’s about looking at value. One man’s trash is another man’s treasure.”
- “You can’t hold judgment and curiosity at the same time.”
- “Fear kicks off everything from the base of our brain and shuts down our reasoning and creativity.”
- “We miss so much information when we jump to conclusions, and missed information is the same as getting misinformation.”
- “I knew that I did not know enough to know what to do with that money, and that would be a disaster.”
Action Steps:
- Embrace curiosity in leadership: Cultivating curiosity allows leaders to stay open to new ideas and perspectives, which is crucial for driving innovation and overcoming challenges. By actively listening and asking thoughtful questions, leaders can unlock hidden opportunities and create a culture of continuous learning within their teams.
- Reflect on core values: Understanding and aligning with your core values can guide decision-making and provide clarity during difficult times. This introspective process helps leaders remain grounded and focused on their true purpose, ultimately leading to more authentic and impactful leadership.
- Remain calm under pressure: Developing composure in stressful situations allows leaders to make informed decisions and maintain credibility with their teams. Learning to manage emotions and respond thoughtfully can transform challenges into opportunities for growth and strengthen leadership effectiveness.
- Foster open communication: Encouraging open and honest communication within teams can build trust and lead to more effective collaboration. By creating a safe environment for dialogue, leaders can facilitate more meaningful exchanges and ensure that diverse viewpoints are respected and considered.
- Stay informed about emerging technologies: Keeping up-to-date with technological advancements, such as AI, can help leaders identify potential opportunities and mitigate risks. By embracing change and understanding the implications of new technologies, leaders can strategically position their organizations for success in a rapidly evolving landscape.
Sponsor: Rise25
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Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90x, Atari, Einstein Bagels, Mattel, Rx Bars, YPO, EO, Lending Tree, Freshdesk, and many more.
The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.
Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.
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Episode Transcript
John Corcoran: 00:00
Okay. Today we’re talking about the power of curiosity, how to lead with curiosity, and what that can do to drive business growth and leadership growth for you personally inside of your business. My guest today is Alana Winter. I’ll tell you more about her in a second, so stay tuned.
Intro: 00:18
Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built key relationships to get where they are today. Now let’s get started with the show.
John Corcoran: 00:34
All right. Welcome, everyone. John Corcoran here. I’m the host of the show. And you know, every week I get to talk to interesting and smart CEOs, founders and entrepreneurs from all kinds of companies and organizations. We’ve had Netflix and Grubhub, Redfin, Gusto, Kinkos, Zippo, Activision Blizzard, lots of great episodes in the archives. Go check those out on your podcast player of choice. And of course, this episode was brought to you by Rise25, our company where we help B2B businesses to get clients referrals and strategic partnerships with podcasts and content marketing. And you can go to Rise25.com to learn all about it or or email our team in [email protected]. All right.
My guest here today is Alana Winter. And she’s a serial entrepreneur that has starred in a number of different companies, some interesting ones. She’s the President of Transformative Forum, which she runs retreats, EO and YPO forums and workshops. That’s actually how we met, coincidentally at an event she had just gotten done, leading a workshop for a group of entrepreneurs that were friends of mine and so, so excited to have her here on the program. But she’s also built and operated a number of different businesses, including a fashion accessories business in Australia, three different successful video distribution companies in the United States, Founder and President of MI6 Academy and Stiletto Spy School.
What’s that? We’re going to find out in a second. So, Alana, it’s so great to have you here today. And I want to start with this great story of when you were four years old. Okay, you’re four years old. You come from a family that was entrepreneurs in the garment business. And there’s a box of scraps that you turned into profit. I love that. More relevant than ever today. Tell me about how you did it.
Alana Winter: 02:14
My dad had just opened up a new warehouse, and the old tenants had left a box in there. I’m four years old. I go over the boxes as big as I am. I look through it and fashion accessories. Later in life. I was fascinated with them from the time I was four and I said, dad, what’s this? And he said, oh honey, we’re just going to throw that out. I said, oh, can I have it? He said, sure. I dragged it down the hall. I went and knocked on the door of the company next door and said, hi, I’m selling fashion accessories. And the guy looked down at me, a little pint sized me and said, oh, okay, honey, I’ll buy the whole thing from you. And I said, oh great. Wow, this stuff is really easy.
John Corcoran: 02:53
He nailed it the first time out.
Alana Winter: 02:57
He said that I’ll need you to hold it for me. And I thought for a second, and I thought, okay, I said, but I’ll have to charge you for storage.
John Corcoran: 03:04
Oh my God, this is like these are lessons that it takes people decades to learn.
Alana Winter: 03:12
He was like, where are you from? He went storming in, accosted my father. He’s like, who are you? What are you sending your kid out to do? And my father was like, what are you talking about? He’s like, you didn’t send her out to do that. My father said, I don’t even know what she did. And I remember this man looked at him and he said, I want to be your business partner when you grow up.
John Corcoran: 03:31
That is amazing. That is amazing. I mean, let’s unpack that a little bit, like just the fact of taking something that was someone else’s castaways but had value to someone else. There’s lots of people that I talk to that struggle with the psychology behind that. They would convince themselves, I can’t do that. I can’t take something that I got for free and then resell it to someone else. And yet that’s psychology. You didn’t have to overcome that in order to make that sale.
Alana Winter: 04:03
Yeah. It’s about looking at value. Right. And you know that old saying, right. One man’s trash is another man’s treasure. There are so many things that we can do to repurpose things into different uses. I mean, for heaven’s sake, that’s what’s being done to clean up the atmosphere. Right now, people are capturing carbon out of the air and turning it into concrete and building materials to solve a problem and create something of value. Yeah, we have to be able to think that way.
John Corcoran: 04:31
Yeah, yeah. For sure. I mean, there’s been amazing businesses created out of taking something that was some kind of castaway or discharge from one process and then turning it into something valuable in another area. So that’s so cool. So you’re you’re what was it like growing up in your family with a father who was an entrepreneur?
Alana Winter: 04:51
Well, from the time I was probably about four years old. My father just used to ask me, so, honey, what kind of business are you going to start when you grow up? Right. It was the. It was the only option. I actually didn’t know that people who had jobs could make real money. I felt a little cheated later in life by having not known that. So I could have had the option. Because sometimes being an entrepreneur isn’t always the easy choice, but it was definitely the only choice in my family.
John Corcoran: 05:21
Yeah. So you actually started college at 16, which is quite a young age to go away to college. And then when you graduated I imagine probably 19 or 20 at that point, which is pretty young to be graduating from college, you come home and you talk to your dad and have a conversation. What was that like?
Alana Winter: 05:43
So because it was always a given that I was going to start a business, I mean, at one point when I started college, like a week after I turned 16 and my dad was like, okay, you’re young, you should go to school. That’s fine. But when I turned 17, he was like, I’m spending an awful lot on tuition. I can take all that and give you that to start a business now, he said, you’ll never get another dime. So business or college.
John Corcoran: 06:07
You lose it. Yeah.
Alana Winter: 06:09
And I was. Like, I knew that I did not know enough to know what to do with that money and that that would be a disaster. So I was like, I’ll go to college and I’ll figure out how to get money for a business later on my own. So when I graduated from college, my dad picked me up. I had gone traveling. He picked me up from the airport. He was like, so what are you going to do now? What did you figure out in your life? And I was like. And he looked at me. He’s like, you don’t have a plan. I was like.
Alana Winter: 06:40
No, I don’t have a plan. So my dad offered me a job for a month, paying me minimum wage to work at a video store. That was over an hour away from the house and I was like, okay, I’ll take it. So I did that at the end of the month. He called me and he said, guess what? You still have a job. Then I just found out the manager is stealing. So I need you to run the store.
John Corcoran: 07:06
Wow.
Alana Winter: 07:08
So I worked for my dad for about a year. A little over a year. Helped him open up some more stores. He was starting, like, a little chain. And in doing that, you know, at the time, I know this sounds crazy today, but at the time, videos cost like $75 to $100 wholesale.
So opening up a store was really expensive. So we would get in the car and drive around and try to find other stores and ask if they had any inventory that, like, had slowed down for them, that we could buy from them at a discount, give them cash, and we could open our store at a lower cost, which we did, and it was great and it gave us a huge competitive advantage. So after working for my dad for a little over a year.
John Corcoran: 07:50
So was the competitive advantage that you were spending so much less to build up? But I imagine you weren’t buying the premium like the new releases. Then how did you handle that?
Alana Winter: 08:02
Oh, you still had to buy some movies at full price for sure. But your inventory, like the thousands of videos that are filling the back catalog.
John Corcoran: 08:10
Yeah, yeah.
Alana Winter: 08:11
Catalog we were getting for a third of the cost and really nobody else was doing that. They were all going in and buying everything brand new.
John Corcoran: 08:18
Yeah. Smart. Smart. So you do that for a year plus. And then what happened after that?
Alana Winter: 08:24
Then my dad called the store one day and fired me.
John Corcoran: 08:28
Why?
Alana Winter: 08:30
Because I’d hit traffic and I opened the store five minutes late that day. He would call every day. He would be calling every day at, like the store was supposed to open at nine. He would start calling every day at about 8:45 to make sure I was there early.
John Corcoran: 08:44
Was he? So he’s like your business partner. He’s this is his store or you were.
Alana Winter: 08:48
My business partner.
John Corcoran: 08:49
At all. Okay.
John Corcoran: 08:50
He was the owner of the store. And you were the manager. Okay.
Alana Winter: 08:53
I was the manager. Got it.
John Corcoran: 08:54
And so he fired you because you were five minutes late. That seems quite egregious.
Alana Winter: 08:59
Well, you know, dad was strict.
Alana Winter: 09:02
And he was actually, I mean, some of the things that he taught me about business and about, really the way that you had to pay attention to detail and that kind of stuff was good. But yeah, he was strict. It was not okay to be five minutes late to open a store. So he fired me and the phone call was very short. And in that phone call he said, you’re fired. I was like. And he said, you know, by the way, you know, we drove around and we saved a lot of money opening up our stores. He said, I bet there’s a business there.
Alana Winter: 09:33
And I said, okay. And I hung up and it took about ten minutes for that to register. So I called him back in ten minutes and I said, hey, you have some inventory in your stores. That’s kind of slow that you could probably use cash for. Can I take that on consignment and use that to start a business? And he said yep. So my guess is that was his intention from the start. So I was in business by 3:00 that day.
John Corcoran: 09:59
With a new business model. Yep. And so did it expand from there? Did you start to go out to other businesses and be like, you have inventory that’s just sitting there, and I will take it on consignment and go sell it to someone else?
Alana Winter: 10:13
I didn’t do it in other industries. I mean, to some extent, actually, that’s what my dad was doing. My dad was in the garment center, and that’s what my dad was doing in the garment center with fabrics. But no, I did it with, just with, with anything that would be in video stores. So videos, DVDs, all that kind of stuff and turned it into a national business. And I supplied, you know, public libraries and Blockbuster Video and mom and pop video stores. It sounds so antiquated to talk about that now, But they were. They were a thing.
John Corcoran: 10:46
Yeah. And so you ended up kind of like what? Did it become like a distribution company? Were you buying from the studios at that point and then selling to the blockbusters and the retail video rental places?
Alana Winter: 11:01
Yeah, we bought from mom and pop stores, stores that were going out of business. We do liquidations and buy all their inventory chains that were going out of business, excess inventory from studios, stuff from other distributors around the country. And we would supply anything from retail stores to, you know, it used to be you’d walk into stores and you would see the displays of videos for sale for $9.99, like we would put sets of those displays up in all kinds of stores. So really any place that as a consumer, you would have gone to rent or buy a video we were supplying.
John Corcoran: 11:36
And you eventually had three separate video distribution companies. What was the difference between the three?
Alana Winter: 11:42
Well, there was one that focused on libraries, and then there was one where we actually got rights to a movie and put those out.
John Corcoran: 11:50
And why? Why make them different businesses?
Alana Winter: 11:54
You know, liability reasons, whatever.
John Corcoran: 11:56
So, okay.
Alana Winter: 11:58
To separate.