The Peering Podcast

Peering 17 - Building Next-Gen Leadership in a Family Business with Bill & Cassidy Wilson
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[00:00:36] Mike Richardson: Hey, everybody. Welcome back to another episode of the "Peering" podcast. If you want to see the future, the best way is to peer into it together. I'm excited about this one, everybody. I've got two of my favorite people in the world joining me today, uh, on the podcast, and they happen to be father and daughter.

How about that? Or daughter and father, I'm not sure which way around I should really say that, Cassidy. I don't know. We'll find out a bit more in a moment. what do they call that? The tail is wagging the dog. Yeah, I think that's right.

[00:01:09] Bill Wilson: Yeah, okay.

[00:01:10] Mike Richardson: I'm really not.

I'm not calling you

[00:01:11] Bill Wilson: All right. Easy Tiger, easy.

[00:01:14] Mike Richardson: Uh, you can understand already, listeners, why I love these two people dearly. They're, number one, they're fun to be with. Number two, they have a great story, a really great story, and it's only getting better. so we'll get to know them a little bit in a moment. Um, uh, but where we want to go today is I'm really, really, really excited that as part of the REFF peer forums that we're running up here in Temecula Valley, we're about to launch a peer forum specifically for next generation leaders, sons and daughters of, uh, our CEOs, and therefore, no surprise, Cassidy is gonna join that next gen group, and I'm really, really, really excited about having you in that, Cassidy, and journeying on with that together more than you already do.

So I don't know, Bill, can you take us back? I'm a little bit fuzzy, but I think you and I first met around the 2013 timeline. How and you, how and when did you and I first meet?

[00:02:14] Bill Wilson: Yeah, it w- it was about that timeline, um, when I was looking to kind of do some of my own personal coaching for me. And, uh, Vistage, I believe you were with Vistage at the time, and I had a gentleman at Ref that worked up in a Corona group that he invited me to, and he invited me to a, a, um, C-suite all hands meeting or whatever that was called, and met a wonderful gentleman that, um, just blew my mind.

So I'm like, "Yeah, it could be a pretty good organization." And but somebody was in that or two people were in that organization that I knew, and I didn't want to, I guess-

[00:03:05] Cassidy Wilson: Be vulnerable ...

[00:03:05] Bill Wilson: be vulnerable to those two people. Okay. Uh, for... There's for a number of different reasons. We won't get into it. It's very personal, but actually one of them was my very first c- first purchasers of a case of cha- a case of Chardonnay.

So anyway, long story short, um, you know, I was kind of looking at Vistage and then lo and behold, poof, you were gone. But I settled on a personal coaching through, uh, the Gazelles Group with a gentleman by David Chavez, and it was eye-opening, and he gave us all the tools to help us scale, because growth will kill you if you're not prepared for it.

And I was trying to do everything, and I was failing at, at a lot of it, or not doing any of it and then failing on, on those. So anyway, it cau- it taught me that I can't do everything, and as a entrepreneur, the biggest thing and the most important thing you learn is you have to do everything in the beginning, but then it gets to a point that you can't do everything, so don't even try.

So anyway, kind of my journey here a little bit, but, uh, yeah

[00:04:21] Mike Richardson: and Cassidy, so then, I started hanging around Wilson Creek Winery a little bit, bumping into you a little bit, and then I joined the board just about a year and a half ago, and we started interacting more. And, uh, you, you... I mean, I'm not even sure what your title is anymore, Cassidy, 'cause

[00:04:41] Cassidy Wilson: No, I'm actually, as of this week, I'm not sure either. We're, uh, here as family you wear a lot of hats and you have a lot of different titles. So,

[00:04:50] Mike Richardson: And how long have you been work, how long have you been working in the winery? You

[00:04:56] Cassidy Wilson: when people ask me that, I say my whole life, you know, grown and raised on, born and raised on the property pretty much. But, um, officially January 2021 is when I started with Wilson Creek. But prior to that, I think it's important to know, as, you know, in the next gen world, we'll get into that in peer forums, but it's policy for our family that if you are a Wilson, you have to do two years outside experience before coming into the family, so that way you have your resume, you're qualified, um, you get the respect from your peers.

So I went out and did that before prior. So I had graduated from college, did some time with, um, Live Nation for, on national marketing scale, and then I went to work for Southern Glazer's Wine and Spirits, who run our distribution. Um, and then I finally begged them to hire me. I said, "You guys need help. I can see it.

I'm tired of stocking other product on the shelf that isn't Wilson Creek. Please let, let me help." So then I joined in January 2021, um, on our distribution team and quickly became in charge of that

[00:05:53] Mike Richardson: And just keep going, 'cause as of a few days ago, you're now in charge of

[00:05:57] Cassidy Wilson: Yeah, I was like, "Well, there we go." So yeah, as a few days ago, like there's, there's a lot to it. You know, I, I grew on the team and I've really, I've realized my career has been trial by fire. I just get thrown into the fire. Um, when I worked at for a distributor, I got thrown into the busiest season selling wine, so it was just running around like crazy and then quickly COVID hit, so it was crazy time for wine sales in the grocery world.

Uh, and then I joined Wilson Creek, thrown into the fire there because who was supposed to be my mentor, our VP of sales at the time, um, had to go on leave for medical reasons and never returned. So I was just handed a laptop and they were like, "Figure it out." He held a lot of information tight to his chest.

He was great at his job, but he was the only one that could do it, so I had to fill in all the gaps. Thankfully, our distributor was a great partner in that. But quickly, um, got into that system, figured it out how, how to win there. Obviously there's a lot of, uh, headwinds in the wine world outside of that.

But then now the next fire I'm being thrown into, um, we- I'm now taking over our tasting room sales as of this week. So, um, that's, that's what's next right now. Go figure out what's, what's going on over there and see how we can make it better and the best quality for the valley.

[00:07:10] Mike Richardson: Bill, you must already be a very proud father, I think about to become even more so and, and onwards and upwards from there. Um, how cool is it to see Cassidy finding her way?

[00:07:23] Bill Wilson: Well, what's, what's really cool about it is none of this was my decision or my idea. This came from my executive team as we're trying to figure out who is gonna fill what shoe where? And so when it came to the most important, cog in our wheel, if not even the axle, is tasting room, and people all pointed at Cassidy and said, "Cassidy, you should run the tasting room."

And she, eyes open, goes, "I'll do it." "And, uh, don't know what I'm doing, but I'll figure it out." Mm-hmm. And so, uh, yeah, she took it on and, and, and I was just... I kinda, I got goosebumps talking about it right now, but I was like, that was not my idea-

[00:08:12] Mike Richardson: Yeah

[00:08:13] Cassidy Wilson: And- ... but I

[00:08:14] Bill Wilson: like

[00:08:14] Cassidy Wilson: it. Yeah. Let's note that. It's never really been, like the executive team, I'm grateful for all of them.

They have to... He's very anti-nepotism, so people think, you know, you're just here 'cause you're Wilson. Absolutely not. I know I have the biggest target on my back. I have harsher critic because of my last name, so I have to work twice as hard to get half the credit, and that's what it's always been. So the executive team brought me on the executive team.

They said I deserve a spot at this table, and then now they, they wanted me to have that opportunity, so I'm, I'm really grateful for the support and I hope to, uh, knock it out of the park.

[00:08:45] Mike Richardson: Yeah, I can v- I can, I can vouch for all of this, everybody, 'cause, uh,

[00:08:49] Cassidy Wilson: Yes. Real, real stuff. My dad's not paving a golden walkway for me over here.

[00:08:55] Mike Richardson: I joined the board about 18 months ago, so I've been, I've been on the inside of all of this. And indeed, as, as Cassidy said, it's really the executive leadership team that said, "No, no, no, no, we want Cassidy in the room.

We want her having a seat around this table." How could we not? Because everybody, it's no secret that Cassidy clearly is front and center on the succession plan after a development roadmap to become the, the, the next generation CEO. Of course, uh, it's a family business, uh, and has had... And we'll get you to fill in the gap in a moment, Bill, with the story, has had 25 years last year of, of legacy so far, and wants 25 more, and, and then 25 more, and then 25 more.

And so, um, we need that next generation leader. And so at some point, Cassidy, you'll take over from the current CEO. Is he any good?

[00:09:48] Cassidy Wilson: You know, I've got a lot to learn from this guy, from being a, being a dad, being a parent, and juggling it all. I, I look back, and I'm sure he'll get into the story, but he was about my age when he picked up our family with two kids, I have two kids, and came down to Temecula, changed his whole life. And it's kind of interesting 'cause my family, me and my husband are going through the same thing at the same period of time, and he definitely took a way bigger jump than I'm taking.

I'm at least he built the foundation for me to jump into. Yeah. So I have a lot of admiration for what, um, him and the rest of the family built here that I get to be a part of, and hopefully the next 25 years get my kids to be a part of too. So it's very exciting. But, we do it together.

[00:10:28] Mike Richardson: So Bill, I believe if I'm correct, you bought the property I think in 1997, and you opened the winery in the year 2000. Is that right?

[00:10:36] Bill Wilson: The timeline goes, uh, we started looking at another winery to purchase in 1995. He dragged his heels, and we realized that he was never gonna sell in 1996. My father got the bug, says, "I want to do this as a family. I think we'll be very good. I don't wanna start from scratch-scratch with planting grapes and wait seven years.

Let's buy an existing vineyard, and let's build a winery." And, and my, uh, sister's boyfriend, or no, husband at the time, was an architect. And that didn't work out, but anyway, um, long story, let's build was not completely out of the realm of, of reality. So we made the leap and, uh, sold our homes, uh, moved out to Temecula thinking that we're gonna build a home on the property, and we started the construction with, uh, just our own money, uh, hoping that a bank would kick in someday.

And, uh, so we started the proj- property in '97. If anybody knows what happened in '97, it rained like hell, and we have a steel building, so they never showed up. We ran into an incompetent turned criminal contractor during that time. Uh, shut it down in '98. Uh, ended up, uh, resurrecting it in '99 after borrowing money from family, friends, and anything that was nailed down.

We s- we sold it. Very, very humbling time period. That was our... We had peanut butter sandwiches for lunch, and we got to have, have the luxury of having jelly on them.

[00:12:20] Cassidy Wilson: Mm-hmm.

[00:12:21] Bill Wilson: I moved a three-and-a-half-year-old with an 18-month-old into a double wide mobile with no running water, no electricity. We had an outhouse generator and a hose.

And I knew I was in trouble 'cause, uh, my wife, when I got home, I w- get took a shower in the hose. She meets me at the front porch, hands me a training potty and says, "This is not your daughter's." So I had to take- Oh, poor mom ... I had to take it to the outhouse and drop it in the outhouse. And I'm like, "Oh, I better hurry up and get this thing done."

So we worked night and day literally trenching to bring in, uh, electrical and water, and I'm operating a backhoe, doing all the things I've never done before. But, you know, it just, you, you, and you build it with your-

[00:13:07] Cassidy Wilson: Trial by fire, you know?

[00:13:08] Bill Wilson: Trial by fire. Just get in there and figure it out, right? So, uh, yeah, we, we opened our doors in 2000, and our biggest problem ever since is that we're too busy.

And so it's been a really, really great problem to have, but it's been driving us. And as you know, and anybody in the, in the business world, growth will kill you. And so, uh, we are now Almost built out enough. Uh, we're not getting the foot traffic we once were, so, you know, we're not as busy, but yet we are selling more to the people that are here.

We are creating raving fans, so, you know, we just have to weather the storm

[00:13:49] Mike Richardson: Yeah. What a story. What a story, everybody. And, uh, if you get-- if you haven't been to Wilson Creek before, I, I'm sure many of you have, uh, uh, then come on by and visit with us. And if you're in the, if you're in the shop there, there's a, a sort of coffee table sized book that if you just flick through it in the first chapter or two, you'll see all the pictures of Bill pouring concrete and, and, uh, living out, living in the double wide and all of those kinds of things.

So it's a, it's a real entrepreneur story

[00:14:20] Bill Wilson: And these guys riding their tricycles and bicycles through the tasting room and out- Yeah ... and walking naked in the vineyard is classic.

[00:14:28] Mike Richardson: Yep

[00:14:29] Cassidy Wilson: Yeah, which is what my kids are doing now- Yeah. ... when we take the kids to visit. But I think it's really cool that, um, the whole family was involved, right? So like my grandparents came and put everything they had in it.

My grandma's still around. She's 96, so if you come visit, you'll see her probably with her golden retrievers. You'll see my dad with his, his golden retrievers. My brother-in-law's in the tasting room. My cousin's on the facilities team and events team. So it really is family owned and operated, which makes Wilson Creek so special, and what we carry into our staff too, treating them like family, treating our guests like family really is the core of what we do.

[00:15:02] Mike Richardson: Yeah, and, and celebrated 25 years last year, everybody, as you heard. And so 26 years this year, as, as you heard from Bill, the, the winery and vineyard opened in the year 2000. And now, Cassidy, we're, we're talking about, okay, the next 25 years of legacy and, um, how we unfold all of that. And Bill, as part of that, um, you know, a year or two ago, you and the family shareholders decided to reconstitute the board and to, to, to bring on some extra external people.

All part, I think, of the bigger plan of, okay, we've got to shift gears, and we've got to open up a whole new next chapter because, you know, we've got headwinds, right? And we need to reset our sails, as you like to say, and, and we need to, you know, really tighten things up and sail onwards and upwards from here, not least of all to create the hospitality experience more than ever before that really is the biggest differentiator for Wilson Creek.

Tell us a bit more about all of that.

[00:16:07] Bill Wilson: essentially it's a big move when you go from a board of family members out- outnumbering the non-family members. And, uh, we were looking for one additional person to be on the board because my father had passed, and, uh, we put out a search and three people propped up.

Uh, you weren't one of them at first, but then it was like, "Hey," as you, you and I got talking further, I go, "He'd make a pretty good, pretty good board member." Uh, we've got a warehouse, I mean, a wholesale guy, good board member. And another guy who was just a good leadership, good dude, board member. I'm like, "Which one are we gonna pick?"

And we made the bold decision of having two family members step off the board. One is my wife, uh, who stepped off the board. She didn't wanna be on the board because it's intense.

[00:17:12] Cassidy Wilson: Mm.

[00:17:13] Bill Wilson: And two was my brother, he didn't wanna be my boss, and he didn't-- he wanted somebody else to hold me accountable than he did.

So it was, uh, two family members, and now four non-family members. And so, you know, we're in a different

[00:17:30] Mike Richardson: Yeah

[00:17:31] Bill Wilson: mindset going in, and then we got these great people that we are tapping their, their wisdom and vision. We're just trying to get you guys all to understand the hospitality more. We have a previous gentleman that was hospitality, uh, on our board and, and he's the ones that, that agreed with, "Yeah, you know, sales are down," and, "Oh yeah, they're down."

And, "Oh, yes, they're up," or, "Yes, they're down." And so he gave, he gave us a little bit, as much as you could equate our businesses together. Um, he's been on our board since 2010.

[00:18:04] Mike Richardson: Yeah.

[00:18:05] Bill Wilson: So the new guys are trying to kind of throw him in by fire and, uh, in a, in kind of a tough economy. But yet, you know, they're each contributing exactly what we wanted.

Uh, we c- and, uh, we couldn't choose just one, we chose all three. And then a gentleman that was with us for 15 years on the board says, "I'm retiring anyway. it's a long commute. I've been with you, and I'm gonna leave it in the good hands." So hired all three of you. Yeah.

[00:18:37] Mike Richardson: Awesome. So, so Bill just mentioned mindset there, Cassidy. Tell, tell us more about your mindset, Cassidy, as you take on this new role and you continue to sort of evolve your roadmap of, of developing yourself into the future CEO. Where's your, where's your head at with all of that?

[00:18:55] Cassidy Wilson: I love it. I think this is the most involved I've been with the board, especially now being part of the, the executive team. But I'm a huge fan of accountability and, and fair treatment, and I think with a board that, that encourages that is awesome. Um, and it's a board that I know I can grow with. I feel like I have your guys' support, but at the same time, with that accountability piece, if I'm messing up, you guys are gonna, you're gonna tell me and hold me accountable, which I would want.

I would not want people to just say, "Oh, Cassie's doing great," just for the sake of it. Like, I wanna know, um, how I can grow and, and learn because I, I don't know everything, and this new role is something that I'm unfamiliar with. But, uh, I'm confident that I can come into a system and, um, make it more efficient and work with people really well, so I hope that continues the next 25 years.

But I also wanna bring with us the legacy that got us here. So one of the things I've done is I've created a, um, next 25 committee within the winery. So it's a committee focusing on growing the next 25 years. It's all, like, the middle mana- not all, but a middle manager or, or leader in their department.

[00:20:00] Bill Wilson: Youngers.

[00:20:01] Cassidy Wilson: Younger, mostly, from, um, the ne- of around the property. So everyone comes in, and we just talk about, like, what's going on in your department, you know? Everyone's so siloed with tasting over here, restaurant over here, wine club over here. So getting everyone in the room and just hearing, like, what's actually going on on the floor, and how can we make it better?

And then I raise that to the executive team of where our team needs us, and I think that's been really helpful. Um, a lot of insight, and that'll continue to be that way because we do wanna... We know that those people are gonna help me shape the next 25 years, and I want it to be something that we're all bought into.

[00:20:34] Mike Richardson: Yeah. And Bill, you mentioned, um, you know, over the last 25 years that you've been, you know, building and running and b- being the CEO of the, the winery and the vineyard, you've invested in various forms of leadership development over time, and not least of all, latterly, you joined the Ref CEO group that I launched in, in Temecula a couple of years ago.

Um, and we'll come to you in a moment, Cassidy, of joining a peer group. But Bill, what, what's your experience of being in a peer group, confidential, no competitors, half a day a month, um, 15 to 17 people, business, professional, personal life. What's your experience of leveraging the power of a peer group?

[00:21:24] Bill Wilson: Um, this isn't my first peer group. I was involved in a peer group dating back to 2010, uh, with family business, uh, CEOs, with all the, the family part of being, you know, talked about the most. Uh, so this is probably the second, uh, peer group that I'm- I've been in. But bottom line, I was very hesitant to be vulnerable because some of them are my friends, some of them are, are the peers in the valley, and I want everybody to look at nothing but good.

But in those peer forums, you share the tough stuff And when you help somebody else that's sharing their tough stuff, you're helping them solve a problem that you actually know you have. And so you're asking yourself the same question, "What do I do about my situation?" And so as helping them, you, you kinda are humbled and hold yourself accountable and say, "I gotta go deal with my own, own stuff as well."

And then the speakers are fantastic, never is the subject content something that is not important to what's happening as a CEO in our world. And as you say, and as books read and anybody in the CEO, a CEO is a lonely job.

You don't have anybody that you can really talk to about your trials and tribulations. You talk to your wife, you scare the hell out of

[00:23:10] Cassidy Wilson: them. Mm-hmm.

[00:23:11] Bill Wilson: You talk to their friends, you don't, you, you don't wanna let them know that you're struggling. There's nobody to talk to. And the CEO Peer Forums gives other people that are struggling just like you to talk to, but more importantly, the one-on-one relationship that you have with the, the forum leader that, that will extract information out of you that you're not quite yet prepared to discuss.

Yes. And he doesn't let you squirm on... He, he makes you squirm on that hook, so to speak, until you get it out and, and deal with it. So there's no hiding, and that's the best thing you can do as a CEO. There is just, uh, it, it's just full openness, and then when you start being open and, and humble, good things happen

[00:24:03] Mike Richardson: Beautiful. Yeah, beautiful

[00:24:04] Bill Wilson: that well enough without punching you in the face?

[00:24:09] Mike Richardson: Um,

[00:24:09] Bill Wilson: We call it a love-hate relationship,

[00:24:11] Mike Richardson: love-hate relationship, yeah.

[00:24:12] Bill Wilson: Yeah

[00:24:13] Mike Richardson: and Bill jokes with me that I have size 15 and a half feet. so with the help of AI, they've created an image of, of me and my size 15.5 feet, but it's okay. I love,

[00:24:23] Bill Wilson: yeah.

[00:24:23] Mike Richardson: relationship too. And, uh, what Bill said, everybody, is I, I often call these peer groups a hall of mirrors because every question that we ask of another member reflects right back on us, and we're asking it of ourselves, and it reverberates around the hall of mirrors, and it lands on everybody, and everybody's asking themself the same question.

"Oh my gosh, that's a great question. I think it applies to me too." Or every bit of input that we give, a suggestion, a recommendation, a story, an experience, a, an insight, a different way of looking at something or thinking about something, doesn't just land on the member we're giving it to. It reflects right back on us.

It's like, "Wow, that's brilliant. Maybe I should do that myself." And then reverberates around everybody and lands on everybody to some degree. So Cassidy, this is what you're coming into. You're walking into this hall of

[00:25:18] Cassidy Wilson: I see you guys meet up here and I kind of just want to put my ear against it and like, I wanna, I wanna go in there.

[00:25:22] Mike Richardson: You're, you're walking into this sort of hall of mirrors. We're gonna launch this-- We are launching this next gen group in September for sons and daughters of CEOs who, who are on, you know, feature large on the succession plan. Also, you know, rising stars in non-family businesses who also feature large on the succession plan as a future business leader.

what are you looking forward to about being part of a, a peer group, a peer forum, uh, a personal advisory board for yourself? What are you looking forward to?

[00:25:54] Cassidy Wilson: I think similar to him, I mean, it's a very unique situation you're in, right? And it could be taken of two ways. Some people get it handed to them and, you know, it looks to them like, oh, well they're just here 'cause she's the daughter. But if you're really working at getting that respect from everyone, there's, there's a lot of gray lines.

There's... It's not black and white, right? Like, you have your family hat on, you have your management hat on, and for me it's about to get even more difficult 'cause now I have family reporting to me. So my- you know, I'm... Sure issues are gonna arise, and learning how other people in a next-gen forum have dealt with that and how they've grown their own reputation is something I'm looking forward to discussing, uh, because I'm sure I'm gonna come with a lot of those situations in mind now that, uh, I just got- gained a whole bigger team and a bigger spot on the property.

So I'm looking forward to bouncing ideas off, off of everyone, and also just getting more mentorship in, in the area. I'm excited to connect with other businesses for a networking standpoint as well, um, and just getting... We're been huge on community with Wilson Creek, so now it's my turn to, to get involved in the community as well.

It's always been through, like, osmosis through my parents, and now, now it's my turn to make those connections and get my name out there through forums like that

[00:27:05] Mike Richardson: Beautiful. Yeah. And, you know, as, as Bill already said, being a CEO of a complex business, whether it's a winery and vineyard and a distribution system, or it's, you know, uh, an aerospace company like I used to run, or it's a real estate development company, or it's a fast food company, or it's a wholesale distributor company, it doesn't matter, right?

Th- those are all complex businesses and organizations and companies to run, especially when, you know, you've got hundreds of employees and thousands and thousands of, of, of customers and clientele and patrons and all of that kind of stuff. It's complex, everybody. And if you like, filling the hole as a round peg in a round hole as a CEO, that's hard. Like, fully filling those shoes, fully filling that seat is hard, everybody

[00:28:04] Cassidy Wilson: Right. And sometimes my shoes will look different. You know, we, we agree on a lot. We're very similar in a lot of ways, but we also differ in a lot of ways for the better for the most part. So

[00:28:18] Mike Richardson: Exactly.

[00:28:19] Cassidy Wilson: who you ask, I guess.

[00:28:20] Mike Richardson: Yeah. And yeah, and so Cassidy obviously is going to find her own mode as a CEO prog- progressively. She's not gonna try to be a s- a second-rate version of Bill. She's gonna be a first-rate version of Cassidy and bring her own flair to it. And indeed, I actually like to talk about this being a square peg in a square hole, because to be a really effective CEO, you actually need some fairly sharp corner pieces, right?

Where you have a cutting edge around strategy, and a cutting edge around execution, and a cutting edge around, you know, the sort of mental agility and innovation required these days to sort of out, outmaneuver the future, out-invent the future. And not least of all, as you mentioned, a cutting edge around accountability, and that can be one of the most challenging things of all, right?

It's hard to thread the needle of accountability. Not too much, not too little, not too hard, not too soft.

[00:29:30] Cassidy Wilson: Especially in a family, family business where I said we do treat everyone like family. So there's a lot of really close relationships within staff, within executive team that have built off of 25 years, and obviously we wanna keep that and, uh, continue to grow that and make people feel welcomed and encouraged to be here.

But at the same time, we have to hold people accountable because this is a business and we need people to do their job. So, uh, it is walking a fine line, like you said. Hmm.

[00:29:55] Mike Richardson: Yeah. Yeah, what she said. Bill, Bill, if you're watching the video, everybody, Bill is pointing at Cassidy. Yeah, what she said. Um,

[00:30:02] Bill Wilson: Easier said than done, as I said. Stop

[00:30:03] Mike Richardson: and in, in many ways,

[00:30:06] Cassidy Wilson: now

[00:30:06] Mike Richardson: yeah, in many ways, everybody, of course, that all adds up to culture, which then adds up to brand, right? Which adds up to reputation, which is, "Oh, yeah, yeah, let's go to Wilson Creek because I've heard, or indeed I've experienced, or indeed every time I go there, I experience phenomenal hospitality, a phenomenal, you know, experience from the parking lot, you know, all the way through to the restaurant and then all the way back out.

It was just seamless and it was beautiful, and I'm just now, as you said earlier, Bill, I'm just now a raving fan telling all of my friends, 'You have to go to Wilson Creek.'" So that's, that's how this all adds up, everybody. So I'm really excited, Cassidy, about having you coming in, into the forum. We're gonna put this forum together, about 15 people.

We've got two or three people committed already who are just gonna love being together. We've got another half a dozen or so prospects who are in conversation. We'll get started with sort of plus or minus eight initial founding members, and then we'll build this out to sort of plus or minus 15, and it'll be this half-day meeting, confidential, coming together, no competitors in the room, totally confidential, where we're just, everybody's helping everybody become that great leader and ultimately where they feature on the succession plan, become a great CEO, that square peg in a square hole.

It's got that round peg inside of it, right? You've gotta be a rounded person. You've gotta, you know, be that leadership presence, but having those, having those cutting edges as well is really crucial. And this is all part, everybody, of this sort of bigger ecosystem of support that we're putting into place up here in Temecula Valley that I like to call CXO Exchange.

Because I'm on the board of Wilson Creek, uh, we can easily book the ballroom, uh, anytime we want to with enough forward planning, and so we did a big event last year where we had about 100 people in the room, including Bill and, and Cassidy, and we're gonna be doing again, the same thing again this year in November where I, I aim to hit the buffers of the ballroom this time.

It can hold, in theory, I think 200 people, and, uh, that's my plan, to fill it again. And, uh, all the ref members will be there, uh, of all these different groups that we're, that we're growing and, and we'll have lots of guests, uh, from around the valley, uh, coming as well. so what's next, Cassidy? You just got this new job, uh, a new challenge.

Uh, tell us more about, uh, uh, the next few days, weeks, and months.

[00:32:42] Cassidy Wilson: Yeah, I mean, just hitting the ground running for sure. Uh, I don't know what my title is or what I'm called, but, uh, it doesn't matter. Uh, I'm just meeting with our leaders in the tasting room over there, figuring out what's working, what's not. Today we're launching a new product, it's called our Bubbly White Cab.

So my first order of business was to go get the balloon arch up over there. Something so simple, right? But it's the little things. And then really working with the team to make sure they feel supported, they f- they're, uh, confident with me on board and, um, eager to dive in together to make the whole process better.

But, um, I think with me, you know, they know I c- I have nowhere to run. I have, I have no escape plan here, so they're stuck with me, and I, I wanna s- succeed just as much as I want them to succeed. So if they lose, that means I'm failing and I'm losing, and that's not an option. So the next step is just to get in there, get my hands dirty, and figure out, figure out what the next real big step is, figure out what the biggest pressure point is in there, and, again, just hit the ground running.

We have no, no other choice but up.

[00:33:43] Bill Wilson: And, uh, just coincidentally, the, uh, tasting room manager that, that reports to her that is the lead dog over there, it's her birthday yesterday and is on vacation for three days, so-

[00:33:57] Cassidy Wilson: No, like five days.

[00:33:59] Bill Wilson: Yeah. So five days until she's scheduled to come back next Wednesday. So Cassie's gonna be in there.

I, I told her, "Just get your hands dirty. Just start pouring wine, start figuring it out." Yeah. "Just show by example, lead by example." I might not

[00:34:11] Cassidy Wilson: know how to use the cash register, but I know how to talk to people and where to direct them to do so. Yeah. So we'll be great.

[00:34:17] Mike Richardson: Uh, it's the best, it's the best way, right? Just get thrown in the deep end and, and learn how to swim and, and,

[00:34:23] Cassidy Wilson: It's sink or swim and there's no choice

[00:34:25] Mike Richardson: and earn, you know, give and earn respect, uh, you know, simultaneously as you do so, and then magical, magical things happen. Uh, love it

[00:34:34] Cassidy Wilson: Right. And that's, that's the thing with being on the succession plan. Like, I don't, I don't want it given to me, I want to earn it, and I want it to be, um, respected as I, I get there. So I don't want it to just be like, "Oh, tomorrow, you know, here, here you're at. Here you are." Yeah. I want it to be like, "Oh, she's worked really hard to get here.

She understands the business. She's definitely an asset, so we, we want her." I don't... I want to be- Yeah ... the team to want me to be in that position, not just handed, so. And that- This is part of it.

[00:35:00] Bill Wilson: And that's what happened on, on, A, her being part of the executive team. I brought her to a strategy session because she's part of wholesale.

Uh, they said, "She needs to be here every Wednesday to be on our executives team." And I'm like, "Okay." Uh, then she's able to tell me stuff that they are scared to tell me, so, uh, she, she holds me accountable more than anybody else on the team holds me accountable. Uh, and the last person I wanna disappoint is my daughter.

And so there's that dynamic, which I think they all knew that would happen.

[00:35:40] Cassidy Wilson: Mm-hmm.

[00:35:41] Bill Wilson: And then, uh, it was their decision as well to put her in charge of the tasting room as her next frontier, and that we can find somebody that can, can do the wholesale, you know, um, job. The tasting room job is, is an animal, and it's a very, very important animal and, and I believe she is the best person for that job.

At some point she was gonna have to figure it out.

[00:36:10] Cassidy Wilson: Mm-hmm.

[00:36:10] Bill Wilson: Some point she would have to be here, uh, uh, in the thick of it, and that's where it all starts over in the taste room. So I'm super, super proud. It's a little early, but- ... you know, she'll, she'll figure it. She goes, "If I have to commute every single day from Yorba Linda, I'm gonna commute every single day."

Yeah. We

[00:36:26] Cassidy Wilson: forgot to leave that part. I, I live in Orange County, so, uh- Yeah ... I'm driving down the 91 and 15 quite often.

[00:36:32] Bill Wilson: But she still has her room here, so,

[00:36:35] Cassidy Wilson: Yeah ...

[00:36:36] Bill Wilson: which we turned into a, uh, a kid's room, so.

[00:36:39] Mike Richardson: And, and figuring out how to get relocated down here. So actually, uh, tell us a bit more about the family side of life for you, Cassidy. You've got a growing family. Tell us a bit more about that.

[00:36:49] Cassidy Wilson: Yeah, so I have two kids. I have an almost three-year-old, and then a s- a 16-month-old, so they're definitely keeping me busy. Uh, the best part, it, you know, I used to just come down here on Wednesdays 'cause that was our executive team, and Wednesdays was always grandma's day. So I would drop them off at my mom's house, and they literally think this place is Disneyland.

We had an annual pass to Disneyland, and my son was like, "I don't wanna go to Disneyland, I wanna go to grandma's house." And I was like, "That's it. I'm canceling Mickey Mouse, and we're going to the winery." So, um, and then on, you know, Friday nights we're here, the whole family. My son and my niece are dancing on stage together, so it's awesome.

There's, there's- With

[00:37:25] Bill Wilson: grandpa ...

[00:37:26] Cassidy Wilson: with grandpa dancing on the stage. Woo. So there, there's four generations living on the property currently because my sister, and my, my niece and nephew, and my brother-in-law live here. And

[00:37:35] Bill Wilson: my mom.

[00:37:35] Cassidy Wilson: Um, well, yeah, and yep, that's the fourth. And, uh, my grandma living here, so I'm excited to be a part of it hopefully.

I mean, that's gonna be a long process, but my hus- I'm grateful to have a husband that fully supports that dream and knows that this is a legacy that we can both get in, buy into for our whole family. Um, and hopefully something we ... Maybe I'll be sitting in his seat one day and my son or daughter's sitting here, and that's, you know, that's really the end goal.

But right now we're just in the thick of it. We had 202. Um, my, like I said, my youngest is 16 months, so we're getting out of that fog. And doing that as a mom and working and growing my career at the same full speed is a whole different podcast, let me tell you. But, um, we're, we're doing it. You know, I might be, like, changing diapers and on a, on a conference call, but someone's gotta do it,

[00:38:21] Mike Richardson: Yeah. Yeah, and, and you know, that's why I'm really excited to have this next gen group mostly made up of family business next gen, you know, leaders because the, the-- especially working mothers, by the way, I take my hat off to you. I have my whole career, any time I've seen a professional working mother, you know, that's got a professional career as well, I have no idea how you do it, uh, along the lines that you just said.

Multitasking to the extreme. Uh, we've all got something we could learn from that, us, us males. Um, and, uh, so it's gonna be really exciting and, and what we've got to do, of course, is to help Cassidy and her peers in the group, uh, become that square peg in the square hole with the CEO skills that they need, navigate the family dynamics that they're, that they're involved in of these multi-generational businesses, and not least of all, reinvent, reinvent, reinvent.

Out-invent the future, because here we are in the face of AI, here we are in the headwinds ar- around alcohol and younger generations changing their relationship with all of those kinds of things. You know, here we are in the face of economic uncertainty and all, and, and global, you know, politics and all of those kinds of things.

And so there's just this never-ending list of, of issues and challenges and problems and opportunities coming at you, as Bill said, that, that you can't help but struggle with. Uh, and, and being in a peer group, you know, that's confidential just means you can, you know, be transparent about it and be vulnerable about it and just put it on the table with others.

And of course, what you learn is you're not alone. Everybody's struggling with the same kind of stuff. And so, you know, knowing that is half the solution. It's not just you. And so listeners, that's what this is all about. If you are a next gen leader yourself, listeners, and you're here in the Temecula Valley area, uh, then drop us a call.

We'd love to hear from you because you might be able to be in the same group as Cassidy here and some other people who've already raised their hand. And, uh, uh, not least of all, we, we will be meeting fairly frequently at Wilson Creek Winery, so that's not a bad place to be. Uh, final thoughts for our listeners as we, as we, as we begin to land the plane here.

Bill, what else would you, would you offer our listeners on anything at all?

[00:40:51] Bill Wilson: Well, you don't just say, you know, the people around Temecula Valley. I commuted down to San

[00:40:57] Mike Richardson: Yeah, that's

[00:40:57] Bill Wilson: commuted down to Corona, and it was worth it, right? it's not just people here. It's, it's worth it. We have

[00:41:06] Mike Richardson: up and down

[00:41:06] Bill Wilson: home, the CEO, he commutes from Orange County, eventually wanting to move out here.

So, um, yeah, don't, don't, don't put that square peg in a round hole and just being Temecula. Mm-hmm. But, you know, a- again-

[00:41:19] Cassidy Wilson: There's a lot of us in the valley, for sure. There's- A lot of family businesses ...

[00:41:22] Bill Wilson: yeah, the, the professionalism, as you've stated over time is, is, is void in this valley as far as coaching and, and whatnot.

but in, in, in landing the plane here, uh, again, it's so important to be able to share without judgment.

I mean, there might be a little judgment in there, but you're sharing and, and they're all saying the same thing. And I'll remember, and I'll never forget, one of our person's first day, she had an issue, and we all told her, "You have to fire your manager." And she looked at it out of utter holy, "I, I don't know what I would do without this person, yet alone have to go fire her."

And, and if I remember correctly, you said, "Tomorrow."

[00:42:20] Cassidy Wilson: Hmm.

[00:42:21] Bill Wilson: And lo and behold, the next day, the person gave her notice and quit. And I, I said, "Hey, name unmentioned here, just think of what you would have gone through in your head had you not heard from a peer group telling you you had to do something you weren't an- even thinking, remotely thinking of doing at the time, and then she quits.

You would have spun out of control, and here you went, 'Oh, thank God.' I didn't have to, I didn't have to do it. She did it on her own." And, uh, I go, " "That's the benefit of the peer forum,

[00:43:09] Mike Richardson: Yeah, and that's-- that what

[00:43:10] Bill Wilson: She gets rid of her the first day.

[00:43:12] Mike Richardson: Yeah, what, what that's speaking to everybody as a, as a CEO, it's a really hard job on so many different levels, and when you're isolated on your own and you're not in this hall of mirrors, you can easily lapse into denial and you're just not even aware of it.

It's a sort of unconscious denial. How much longer are you going to tolerate this stuff? Is the kind of accountability that you get from a, a hall of mirrors peer group. And so, uh, that was, that was what, you know, we were doing in that moment. We weren't, we weren't, you know, um, relieving the CEO of, of their responsibility.

It's their decision at the end of the day. But when they've got a sounding board of other peers in the room that they trust, I trust your perspective, I trust your experience, I trust your vantage point, uh, then it just helps build self-confidence to do difficult stuff. for sharing that, Bill. Well said. What, what final thoughts, Cassidy, do you have for our listeners?

[00:44:16] Cassidy Wilson: Well, I've enjoyed the, the CXO Exchange to the point that I've been involved in that, and the AI Incubator event was really helpful just hearing from other people. So I'm looking forward to the, the NextGen forum, looking forward to getting more involved with the family business and the board, um, with your help there, and just ready to take on the next chapter of challenges

[00:44:37] Mike Richardson: Yeah. Beautiful, everybody. So there we have it, another episode of the "Peering" podcast. If you wanna see the future, the best way is to peer into it together. If you fancy being in the next gen Peer Forum with Cassidy, drop us a line and we'll, uh, we'll certainly have the conversation. Bill, Cassidy, what a pleasure.

What an honor. You're two of my favorite people. Thanks so much for taking the time tod- We'll see you at the next board meeting. And the listeners, come on back and be with us next time. Thanks everybody.