Start With A Win - Cindy Waddle: 2025 Start With a Win Holiday Special

Starting point is 00:00:00 Leadership really doesn't have anything to do with power. It has everything to do with trust, integrity, being a person of your word, and showing that you care. Because if you show your employees that you care, that they matter, that they're smart, that they are killing it, they're going to give you their very best. And leaders just need to open up to the idea that people really, really matter for their mission. Welcome to start with a win where we unpack leadership, personal growth, and development. and how to build a better business. Let's go. Happy holidays. Merry Christmas and all the other holidays we're celebrating this time of year. Coming to you from Area 15 Ventures and start with a win headquarters. It's Adam Contos with Start with a Win. Have you ever met someone who turned

Starting point is 00:00:46 an act of kindness into connecting words into a movement that's changing lives? Seems like a common theme amongst very successful people. Well, today our guest, Cindy Waddle, did just that. After a 38-year federal career, so worked for the government for 38 years, rising to a senior position without a college degree, mind you, Cindy followed her heart and founded desire to inspire, a company built on a simple but powerful belief that words can connect and heal. What started with her writing 365 handwritten cards to comfort a grieving family, which, by the way, I'm a huge proponent of handwritten notes. This has grown into a mission-driven brand, creating inspirational products that bring hope, resilience, and connection to people everywhere. She's been featured as the cover star of Female Entrepreneurs Magazine and continues to prove that grit, compassion, and purpose can redefine success.

Starting point is 00:01:47 Welcome, Cindy, and Merry Christmas. Thank you. Merry Christmas. I see you're all decked out. This is going to be a lot of fun today. We're going to dig into your business because, I mean, frankly, there's a lot of your business being passed around and utilized this time of year. But also, we're going to get into some Christmas trivia at the end of this. So it should be a lot of fun. But I want to take you back.

Starting point is 00:02:11 Government career, you know, government employee, which thank you for your service to our government. You're welcome. You're welcome, I guess, right? Yes. Awesome. So how did you go from, and by the way, I was a government employee, got the entrepreneurial bug and started businesses. as well. But how did you go from being a government employee to being an entrepreneur? Take us through that briefly. Yeah, when I was a government employee, I worked at Peterson Air Force Base for many years, and I decided I need to give back to the community. So I became a hospice volunteer. And my very first patient was somebody that I absolutely fell in love with. She had two daughters in their 20s, and I lost my mother in my 20s, so I knew the pain they would feel. So I went to

Starting point is 00:02:57 the hospital every day after work and gleaned as much information as I could from the patient. And I went home every night and I hand wrote 365 days worth of their family, their traditions, their loves, wisdom, inspiration, quotes for each girl. And I made the cards different. And I didn't tell them I was doing that. And at their mother's funeral, I presented them to them in a beautiful box. And the grandmother called me about a month later and said I changed their lives. She said that the girls called each other every morning and read their cards and that it had really changed their lives. And it wasn't probably a month after that. I can still picture to the day. I was in my bedroom getting ready for work and God shone a light on me and said,

Starting point is 00:03:44 you know what, if you can do this for them, you can do this for others. And my dream began. I retired from the government six years ago and started this amazing company that I'd been thinking about for about 12 years. Wow. It's incredible. And for all of my business friends out there, there's something super powerful here because we always talk about handwritten notes and the connection that this makes with the person you're giving that to, as well as the connection you have while you're writing it. So, you know, you've developed a business called desire to inspire out of this. So what does your business do? And then I want to unpack kind of the psychology behind some of this and why this is so impactful and powerful for us.

Starting point is 00:04:25 Perfect. So unlike the traditional greeting card company, you go in, you buy a card, it has a message for an occasion. We offer card sets in 30, 60, 90, and 365 days. And we celebrate the happy times, but we also touch on the times that are often left unspoken. My husband and my business partner are both veterans with over 20 years of military service. And so we touch on PTSD and depression and anxiety and loss of a cat, loss of a dog, grief, loss of a loved one. We also touch on the happy time, celebrating your mother and your father, not just on Mother's Day and Father's Day, but every day of the year.

Starting point is 00:05:11 And I think it's important. We have them for best friends and just daily inspiration. And I think daily inspiration can change your mind. set words really do have power wow it's it's incredible and you're you're so right about that you know you think about like people getting into reading a bible verse every day or um you know just looking for that particular connecting quote or what have you on social media in fact i mean the most shared liked valued things on social media are quotes so i mean this this is this is powerful but you're not just giving like you said a greeting card okay once a year from something

Starting point is 00:05:51 buddy. That's fantastic. But the reality is most people get like when they get a greeting card, it's like a birthday or a holiday or whatever. And they get like 10 of them. And yours kind of blends in with that. But however, what desire to inspire is doing is you're making a longstanding relationship out of that connection with that repetition. How did you come up with that understanding that, you know, being with someone daily has such a greater impact? So, you know, When I was writing the cards for the girls, I thought that grief starts, you know, when their mother becomes ill. It lasts for a very long time. It lasts for a lifetime.

Starting point is 00:06:32 So I wanted to carry them through the first year as much as I could with that. And I think that, you know, you need that repetition. You need to understand that you need to tell yourself every day that you matter, that you are a winner, that you are empowered, that you can handle life because life is full of challenges. And I think that daily reinforcement is so important. And it also reminds the recipient that whoever gave that to them really cares enough about them to share that inspiration with them. That's incredible.

Starting point is 00:07:10 And you mentioned like veterans with PTSD. There are a lot of people in the public sector with PTSD also. I was in law enforcement for a long time, and it's a real thing. So, but I mean, we're kind of dwelling a little bit on the painful aspect of people's emotions. But you turn a lot of times pain into purpose or create motivation and turn that into, you know, inspiration to go accomplish things. How do we, how do we recognize what somebody needs with this and balance what we're given them? You know, I have, I have customers that say, could you write a set for this or could you write a set for

Starting point is 00:07:49 that. And I've listened to that over the years. And, you know, we currently have 30 sets of cards. And we've determined that those are the most important right now. There are so many topics we could cover with these cards. We just came out with one that I was asked to come up with through the guy that I bought business insurance from. And it's called chill breakers. And it is ice breakers for a corporation, for a family. It's getting to no one in again. I feel like with COVID, we all introverted into the shell, and we lost that connectivity that is so important in life. And I want to bring that connectivity back. That's awesome. What is your, what's your most popular card set?

Starting point is 00:08:37 A lot of them are popular, probably one that is just mainstream, everyday uplifting messages. words of wisdom has been significant, but also we have one called girl power. And it's empowering women to know that they can do this, that this world is for them to go out and conquer. And that's been a big seller as well. That's awesome. I'm going to have to get me a couple sets of those for my daughters. Yes.

Starting point is 00:09:06 So, okay, well, how, let me ask you this. You know, when you look at leadership utilizing a tool such as a quote or inspirational, inspirational statement or something like that. How can leaders really break through this barrier of, you know, I don't want to call it ego, but status and connect people more, you know, connect with who they're leading by the heart. I mean, it's because it seems uncomfortable a lot of times for leaders to give somebody a quote, a card, whatever it is. When it's kind of touchy-feely, you know, you're not, you're not trying to be inappropriate or anything like that, but you're, you're trying to connect emotionally with people because that really, you know, we can get so much more out of ourselves

Starting point is 00:09:51 when we're free to do so. Absolutely. What advice do you have for leaders when it comes to that? You know, we've talked a lot about that. And these cards, leaders, as you said, don't feel comfortable being intimate or, you know, letting their heart open up. But truly, leadership at his core, it's about the people that work for you. It's a people first.

Starting point is 00:10:14 They have to listen before they speak. They have to lead with empathy without losing accountability to make decisions that honor compassion and fairness. Leadership really doesn't have anything to do with power. It has everything to do with trust, integrity, being a person of your word, and showing that you care. Because if you show your employees that you care, that they matter, that they're smart, that they are killing it, they're going to give you their.

Starting point is 00:10:44 very best. And leaders just need to open up to the idea that people really, really matter for their mission. Awesome. And by the way, Cindy is not just coming from a place of selling cards. She's been in HR for decades and is an expert on this type of employee, human development, things of that nature. So listen to what she's saying here. It is impactful. It does make a difference. You know, we we also have to build, you know, performance and accountability into that as, you know, from the world you come from. You know, HR is probably the one who's most interested in performance and accountability. How do we, how can we connect those feelings to that accountability piece and build that inspiration in so that people perform better? Yeah, that's a great question. Accountability is

Starting point is 00:11:34 so important as a leader. You have to provide clarity, but you have to provide consistent. see you have to listen to the issue, understand both sides, show genuine empathy for what people are going through. But at the end of the day, you still have to handle the situation according to policy, according to guidelines. That balance, compassion with expectations is what real leadership looks like. You can extend grace and still set boundaries. You can listen deeply and still make tough decisions. And when leaders lead this way, people don't just comply. They commit. Accountability becomes something people honor, not something you have to enforce. It sounds like you've given this speech before.

Starting point is 00:12:22 This is really good stuff. This is really good. All right. So we have, you know, you have the ability to deliver this inspiration, this, you know, to use a catchphrase here, this desire to inspire What does that do for the relationship between, you know, call it the supervisor and the employee or the employer and the employee? I mean, do you think this helps break down that barrier where you can approach those difficult conversations easier? I absolutely do. I think building that trust and as a leader, showing that you really care about the human side is so critical and so important. um leadership again is really about your people and you have to show them that you care that you hear them that they matter and they're going to follow you and they're going to want to be

Starting point is 00:13:18 their best for you awesome i love it all right so we're on this leadership kind of the topic right now if if you were to write or maybe i'm sure you have a 365 card message set for today's leaders, something that you would give your leader. What do you think one of those good ideas would be that the themes that you come up with? Because the themes that you have on your cards are so amazing. They're inspiring. They get the point across. And I think sometimes we need to read something instead of somebody telling us something.

Starting point is 00:13:56 Because when we read it, it's not necessarily coming from that person. It's coming from within. So, I mean, what would you tell? leaders in their cards set? So it would be that great leadership is defined by compassion, courage, and character. A heart-led approach rooted in integrity, resilience, service, and faith. This theme captures my true core traits of leading with heart, leading with honesty and strength, leading with courage, through all the trials and tribulations that you face as a leader,

Starting point is 00:14:32 leading by lifting your staff, lifting others, and leading to make a difference. In my mind, that's the true theme of leadership. You know, when I was the HR director at the Denver Mint, my staff knew I met business. They knew that I wanted them to perform and to conduct themselves professionally. But I also recognized every time they went above and beyond. And I had what was called a kudos board. and every time they went above, I wrote out a card and I put it on the board and every month I would see who got the most cards and that person won a gift card that I paid for out of my pocket. And let me tell you, that kudos board became widespread throughout the mint and everybody loved them and it was so uplifting and made them want to excel and do better and succeed and make me proud as a boss.

Starting point is 00:15:27 And I truly believe that leadership isn't a thing of knowledge as power. I know more than you. The more knowledge I shared with my staff, the better we looked. So it was always about educating them and letting them know, no secrets, unless I had to keep a secret. But, you know, being transparent and forthright and letting them understand that that's how I was as a leader. Awesome. So, you know, to kind of wrap up the whole conversation on your company, I think one of the reasons why people don't give handwritten notes or give note cards or anything like that to people on a daily basis is they struggle to come up with the quote, the statement, things of that nature. What advice do you have for people?

Starting point is 00:16:18 I mean, it's not expensive and it's not difficult to use this tool that you've created. What advice do you have for people out there, whether or not they're a leader? Maybe they're in sales. I have a lot of friends who are in a real estate space. They're real estate agents. And they want to have a way to connect with people regularly. So they stay top of mind and continue to build that trust because they want people to know they care. What advice do you have for them as an expert in the handwritten,

Starting point is 00:16:48 note and delivering inspiration space. You know, Adam, it's so important because every time I pull out a card that was given to me by my best friend, I remember her. I think that she took the time. She spent the money to give me my own set of cards. And I think of her every day when I read a card, but also it puts you in a habit of transforming your mind. One of my favorite sayings is be ye transformed by the renewing of your mind.

Starting point is 00:17:16 I believe if you get a message every day that is uplifting and inspiring, you're eventually going to believe that you matter, that you're important, that somebody cares about you, and buying a set of cards, I created a set for realtors that it's a little flipbook and it's thanking a customer for buying a home from them. And they have that set for the rest of their life, unlike a bottle of wine or a box of chocolates or a bouquet of flowers that die or get, consumed, you can have this flipbook on a shelf as a reminder that your realtor cared enough about you to give you daily inspiration for 30 days to thank you for being a customer. It's those sort of things that make a difference. That's a great closing gift or add it to your closing gift for that matter. So, you know, agents out there, realtors, brokers, listen up, look up Cindy's website and get something going with that because these things do matter. Cindy, it's the holidays and we have some

Starting point is 00:18:22 holiday trivia here. So are you ready for this? I'm ready. Okay. And all of these have a leadership theme, by the way. Okay. Well, most of them do. So a couple of them don't. But all right, here's the first one. You and I grew up in a generation where we watched Rudolph the Red Nosed reindeer, you know, you got the song, things like that. And there's multiple choice. So who finally recognizes Rudolph's unique value and puts him in the lead, which is a great example of adaptive leadership. You know, he was picked on, you know, couldn't play reindeer games, whatever it is. Right. Was it Comet, Donner, Santa Claus, or Clarice that recognized Rudolph's talent?

Starting point is 00:19:14 It was the person that the hat you're wearing, and it was Santa Claus. There we go. He shifted his mindset to see Rudolph's difference as a strength. What leader shouldn't do that? The most unconventional team member becomes the one who leads you through the storm sometimes. So recognize potential. Totally. That was a, I mean, great explanation.

Starting point is 00:19:39 Thank you, HR leader. That's it. All right. The movie Elf, you know, Buddy the Elf. I love that movie. Buddy says the best way to spread Christmas cheer is what? Sharing cookies, leading with joy, singing loud for all to hear, or giving high fives. Singing loud for all to hear.

Starting point is 00:20:03 It's a reminder that enthusiasm sets the tone. When a leader shows energy, optimism, and authenticity, the whole team can fill it. So sing out loud for your staff. You are rocking it with this. You must take in all the Christmas movies. They're a lot of fun. All right. Here's one that is kind of across the board.

Starting point is 00:20:26 What holiday character was basically the first change management case study? So the first change management case study, resisted to transformation until he saw his future impact, which was it the Grinch? I kind of like that one. Scrooge, Frosty to Snowman, or Kevin from home alone? It could be the Grinch, but it was Ebenezer. And he changed when he was confronted with the ripple effects of his choices. It's a lesson leaders need to learn today. real change happens when you understand the impact of staying the same.

Starting point is 00:21:05 So listen here and change when you need to. You should write a book about this. Leadership lessons from Christmas movies. I love it. Okay, here's another one. When pulling Santa Slay, which reindeer would make the best team leader? So Rudolph, because he's innovative and visible, Dasher, because of speed and energy, blitzin,

Starting point is 00:21:29 because he's reliable under pressure or vixen because of charisma and connection. Who would make the best leader? I'm going to say dasher because he's fast, focused, and dependable. Traits that make you a strong operational leader. My business partner is the visionary and I'm the dasher. I am the go get it, do things done. He's the visionary.

Starting point is 00:21:54 He's the one that sees the big picture. And we're a perfect team because of that. I love that. That's great. Yeah, I mean, it's, I guess you could probably almost pick any of them. I mean, they're all, you know, you have a great winning team. You're going to have a lot of great leadership potential on it. That's right. So that's, that's kind of cool. All right. Last one. This is, this one's a little bit different. And I'm not going to give you any sort of, you know, choices here. You're going to have to pick the answer out of your head here. What popular Christmas beverage is also known as milk. punch. I think it's something that I really hate called eggnog. I think it's yucky. But whether you love it or hate it, it represents a tradition of bringing people together, much like shared values in strong teams, that repetition, that shared ritual is important. But the eggnog itself is pretty gross. Even in like a coffee or something like that?

Starting point is 00:23:00 Yeah, just can't do it. All right. All right. You're one of the few, but, you know, we'll give it to you. What are you put in at brandy or something? I'm down with it pretty much anything in my coffee. Okay. Eggnog, gingerbread, you know, whatever it is.

Starting point is 00:23:18 Okay. Are you gingerbread latte person? Do you have to have your coffee? I do. Yeah, it's right here, right here. Me too. All right. Cheers. Okay.

Starting point is 00:23:27 Everybody, make sure you check out Cindy Waddle. You can find her at DesiretoInspire.com. That's D-E-Z-I-R-E-T-O-I-N-S-P-I-R-E dot com. You can reach her at Cindy at Desireinspire.com. She is local to the Denver area, which not very far from where we're actually shooting this episode. And she's also been featured in so many different guys. great, you know, online or television shows. So some great television interviews, women's entrepreneur magazine, things like that.

Starting point is 00:24:02 Congratulations for all your success. Everybody makes sure, I mean, it's, you don't have to sit down and think of how do I write out 365 days of cards. Cindy's done that for you. So spend a few bucks, get her decks of cards, and share that connection that you have with your customers. Cindy, I do have a question I ask all of our amazing guests. on start with a win and that's how do you start your day with a wind you know adam i start my day

Starting point is 00:24:31 um not even getting out of bed yet um i thank the good lord for the life he has given me um sometimes i question him sometimes i have an autoimmune disease that i've had my entire life i am a family of six that i'm the only one left um at the age of 65 i'm the only one of my family that's left. So sometimes I find myself feeling sorry for myself or asking God, why me? What are you punishing me for? But I have to wake up every morning and realize I'm alive. I can get out of this bed. I have all my limbs. I have all my senses. I have my family. I have God. I have everything I need to make it another day. And just that blessing in itself is what guides me. I love it. I love it. And you built in no excuses in.

Starting point is 00:25:24 that. So that's perfect. You know, you can get up and do it. Cindy, it's been awesome having you on the Christmas episode of Start With a Win. Everybody make sure you check out DesiretoInspire.com and Cindy Waddle. Cindy, you've been a great leader in business and serving our government for many, many decades. So thank you for that. And thanks for all you do to inspire us. And thank you for what you do to inspire us. I appreciate being on. Thank you. Merry Christmas. Merry Christmas.

Start With A Win - Cindy Waddle: 2025 Start With a Win Holiday Special

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