The Learning Leader Show With Ryan Hawk - 266: Ryan Caldbeck - CircleUp CEO: How To Build The Frameworks Of Your Life & Career

Episode Date: July 15, 2018

The Learning Leader Show With Ryan Hawk Episode #266: Ryan Caldbeck - CircleUp CEO: How To Build The Frameworks Of Your Life & Career We are hosting a workshop on developing YOUR personal excellence as a leader.  For details and availability, go to RyanHawk.me  The Learning Leader Show "What we look for in a person: Horsepower, Integrity, Work Ethic, Teamwork, Pride." Show Notes: Sustaining excellence: Persistence - regardless of skill, willing to run through unlimited doors with no light at the end of the tunnel. It can be soul crushing Identified focus passion - an understanding of the passion that is identifiable. Drive - A motor. Really good at email and/or communication. Can't take too long. "Have a motor." Always moving Values - "I don't say that lightly." You can't sustain excellence without values. "A framework to understand you." Isn't it hard to know what your passion is? "Yes. I got scared about the treadmill that I saw others get on."  However, people don't think they can leave the corporate job that pays well.  But you can.  Begin by thinking about the framework to make it happen. "Silicon Valley is a hard town to talk about challenges." What it's like to lead 60 employees What mistakes were made in the hiring process? "We took too long to make frameworks." "Frameworks show others what to do." What traits/values do you look for in hiring? "The airport test doesn't make sense to me. I don't have to want to spend a day around them in the airport." "We have crystallized what we look for in a person." Horsepower - intelligence over experience Integrity - don't talk negatively about others Work ethic - must be willing to work hard Teamwork - need to work well with others Pride - Care How to gauge work ethic in a job interview? "It starts with everyone knowing we are looking for that." Advice for the individual contributor making the leap to manager... "Figure out framework for your specific role. Get clarity on what each person's role is." "Learn how to develop empathy for what your team goes through. Sit with them without micromanaging them." "Make sure you have a resource (person) to talk to about being a manager. Hire a coach. Get a peer group outside of your company." Why joining The Learning Leader Circle is a good idea Ryan has a coach and a group of 12 CEO's that he meets with regularly Building culture: Focus on your mission "To help entrepreneurs thrive by giving them the capital and resources they need." Their Values: Do it right Be brave Be a solution Constantly reinforce the vision Most useful advice: Winston Churchill - "Never give up." "Do what you're passionate about" How to have balance at home? Two kids and his wife is a senior leader at her company Mediation after the kids go to bed Online working from 8:30-10:00 Spend time with spouse only Use the "Get To Know You Document" "If you don't keep growing, you will become irrelevant." Social Media: Read Ryan's tweet storms: @ryan_caldbeck Connect with me on LinkedIn Join our Facebook Group: The Learning Leader Community To Follow Me on Twitter: @RyanHawk12 More Learning: Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon Episode 216: Jim Collins -- How To Go From Good To Great Episode 179: How To Sustain Excellence - The Best Answers From 178 Questions Episode 234: Jocko Willink -- Why Discipline Equals Freedom

And so for us, there are a couple key things we look for. Horsepower, I take intelligence over experience any day of the week, and that's a really important thing for us. So horsepower is something we look for. Integrity is a tough one to test for, something that we often ask about. It's like, you know, talk to me about your prior manager, your prior job. And usually when someone is kind of dumping on their prior manager or teammates or job, that is usually, a red flag on integrity, but there's some other ways we test for it as well. Work ethic is another one that we care a lot.

If someone has work ethic, integrity, and horsepower, that's usually a pretty darn good teammates. Welcome to the Learning Leader Show. I am Ryan Hawk. Thanks so much for being here. We are hosting a workshop on developing your personal excellence as a leader. We're putting everything we've got into this over the course of two days in the fall. We'd love to have you. You're going to keep it small so that it's engaging and intimate.

Go to Ryanhawk.me for dates and availability. Go to Ryanhawk. We'd love to have you. Now, on to tonight's featured leader. It's with Ryan Caldbeck, the founder and CEO of Circle Up. It's an investment platform powered by technology. Ryan received his MBA from Stanford and his undergrad from Duke. Circle Up has been named one of the top five.

most disruptive companies in finance by CNBC, also one of America's best entrepreneurial companies by Entrepreneur Magazine and many other awards. Ryan has done some incredible things in a short period of time. A few of the topics we got into the importance for building frameworks based on your values. Then how to find your passion. This came up a few times. Really interesting. Then making the leap from individual contributor to manager and how to avoid the mistakes, both of us have made and then specifically how he designed the culture at Circle Up to be a place where people want to work ladies gentlemen this one is really good with Ryan called back all right Ryan thank you so much for joining us here on the Learning Leader Show welcome thank you very much for having me I became aware of you

maybe like a lot of people I use Twitter as a news aggregator for me to learn from really smart people. And your tweet storms came up for me, probably from them being retweeted by others. And I became a follower of yours. And I thought, I've got to find a way to talk to this guy. So that's, uh, that's how I initially heard you. I really appreciate the fact that you take the time to do that. Thank you. It's, uh, it's been fun. I've only been on Twitter for a couple months. But it's, it's been a really fascinating channel to just get some, get some thoughts out there. Yeah, it's helpful. So I'm, I'm curious. You've, you have spent a lot of time already around. people who have sustained excellence.

And obviously, if you look at your background, which we're going to get into, you have done the same. I'm curious from your perspective, what have you found to be the commonalities among those who are able to sustain excellence? It's a great question. I think that there are a couple that come to mind for me. And I don't know that these are necessarily in order. There are some that link together.

But a couple that pop out to me are first persistence. I think no matter someone's skill or resources, it takes a tremendous amount of persistence to achieve excellence and then even more persistence to sustain excellence. I think you have to run through a seemingly unlimited number of doors with no light at the end. And it's hard. And I've talked before both privately and publicly, it is sometimes really kind of soul-crushing to receive roadblock after roadblock after roadblock and keep wanting to get through it. I think that persistence can be driven by a number of

different things, but I think it is sometimes connected to another quality or trait that I think people that sustain excellence have, which is they have an identified and focused passion. So I think passion in and of itself can be a really powerful thing, but it really needs to be focused and the person needs to understand what that passion is. And that's something that I see a lot of people missing on, particularly those that went to great schools, maybe had great jobs out of school, and kind of were doing what they were told to be doing. Their parents told them to go to the best college, told them what major to have at a college, you know, the career center set, go into consulting or investment banking, but they never really identified or focused on what

makes them passionate. When I've seen someone's sustain excellence, they're able to identify kind of what gives them passion. And that passion often gives them an irrational ability to be persistent and run through walls. So those are two. Two others that come to mind. One is a drive, and that is related to persistence.

but there's kind of a motor that I see from people that sustain excellence. And so this may sound silly, but a trait, a commonality that I see from people that are just phenomenal at they do, is they're really good at email or communication in general. And what I mean is, like, when I email a CEO and a person takes a week and a half to respond, and the response is just, I'm really jammed. I see a pretty good correlation between that delay and that person's ability to achieve or sustain success. Conversely, I've emailed people that are running multi-billion dollar companies, public companies, and they can respond within 24 hours. The ability to just have a motor that keeps going.

And you can demonstrate in a lot of different ways I happen to have a personal bias that emails in a way to see that, but just that motor that they're always moving. They're always trying to push a ball forward in some direction, or push one ball forward, I mean. And then the fourth one I'd say is values, and I don't say that lightly. I find that people can achieve excellence or achieve some success in some area of their life, particularly financial without values. I've never seen anyone sustain it without a kind of core set of values that they live by. Values act as a framework in my experience and it's a framework to more effectively make decisions. It's also a framework for other people to understand you and to understand what you stand for and what you don't.

And I think that those values or being able to identify what values matter to you most and why is an important component both for yourself to make decisions and for other. people to understand the why behind you. Number two, you said identified and focused passion. And then you described the person who went to the good school, who did the job that the parents thought they should do. Were you describing yourself? Yes.

Okay. Tell me more. That's it. Yeah, that's a. Absolutely. And I got some advice when I was in college. I got offers from three consulting firms, Bay and BCG and McKinsey. And I was fortunate enough to get them, and I felt really lucky.

And coming out of college, I got advice from a basketball coach. And a basketball coach said, I was trying to talk to him about, like, hey, what do I do? And he just said, what are you passionate about? What do you love? And in my head, I'll be frank with you, I really discounted that question. In my head, he was fortunate enough to be a basketball coach. And I would love to be a basketball coach, but, you know, I don't think I can do that. So I need to go put food on the table in another way, and I need to go have a career.

And I missed the point of what he was saying. And it took me at least 10 years. Well, actually, can only until circle up, so right around 10, 12 years, to identify what he meant. And what he meant is it's not really about being a basketball coach or not being a basketball coach. It's kind of the why behind being a basketball coach. or doing anything. And the why was always missing for me. Like, why did I go into consulting?

From consulting, I went into business school. From business school, went into private equity. And I kept missing like the, well, what was pushing me? To be candid with you, it wasn't money. Like money is something that motivated some people. I was always uncomfortable with money. With that prospect, I didn't come from a lot of money. I thought none of my friends had money and I was very uncomfortable with it.

But I was missing the what. And so I was listening to feedback from career centers and from people that were older than I was to say, hey, look, you should join this consulting firm. You should go to this business school, go to this private equity firm, et cetera. But I never really identified what I was passionate about. And around mid-2011, when I was working in private equity, my then-girlfriend, now wife and I were in a series of conversations about like, I just wasn't that happy. And my job was like amazing. The money was embarrassing, good. The hours were fantastic.

I genuinely loved who I worked with. I mean, the founder of the firm cried when I left. But what she helped me identify was what I was passionate about. And we went through this exercise that took several months to just really identify, like, what is the, you know, kind of like the five why is. Like, why do you like doing certain things and not others? And then you keep asking yourself, why and why? You kind of drill into, for me, it was helping other people to thrive.

That was something that I just loved. And I saw that at different points in my life, but it took me a long time to kind of recognize that passion. And that's what I missed. And someone, that basketball coach gave me that advice when I was 21. And I, you know, didn't listen. I didn't hear it until much later. Do you think I, I, that story resonates with me because when I was a similar age,

if you were to ask me that. I mean, I was playing football at the time, so I wanted to play in the NFL. But other than that, I didn't know. And I think it takes, do you think,

I remember when I was early in my career, I worked in sales and management and then leadership. And I applied for these, these leadership development programs within my companies at the time. And when I was very early in my career, I remember I got turned down. And I was really upset with the people who turn me down. I thought they were wrong.

and they said, listen, some things just take time and they take experience and you don't have that. You are, you just haven't lived enough. And I, at the time, I thought, that is so stupid. That is not true. However, the more I thought about it, I think as much I don't want to admit it, that there is validity in those statements of saying, in some cases, you just need the reps of life. I use the phrase reps, repetitions, because of my background of, of whether it's true. Repetitions watching film, repetition is playing football, repetitions throwing a pass, develop the muscle memories so you become better, especially when the stakes are high.

And in a way, I thought, they're probably right. I needed some of the reps of just life experiences in general. And do you think a lot of 22-year-olds, even though the 22-year-olds listening don't want to hear this, do you think a lot of them just, it's near impossible to know that answer at that age? Or are you and I just a different case? I think you're right. I think it is near impossible to know it. And I also, you know, I get calls from people that are graduate from college or business school,

but are younger to your point. And I get scared talking about that story that I just gave because I worry that it will lead someone to incorrectly identify their passion. Yeah. And it'll lead them to, yeah, perhaps chasing that dream to be a professional golfer 15 years longer than they should have when they kind of missed, well, what is it about the golf that matters to them? And what is it about what's the common thread between golf and actually teaching someone else and something else? That common thread that is really the underlying passion. So I do worry that people that are 22, 25 might be too young to have enough life-repped to identify it. Having said that, I also get really scared about the treadmill that a lot of them get on that's hard to get off of. you know, when I made a leap and left private equity to start my own company, I got calls from an absurd number of people that were working in private equity firms or hedge funds that on the resume, you'd say this person is set for life.

And the calls were always the same. There was a profound, somewhere between sadness and jealousy. Like, I wish I could do that. phrase, I wish I could do what you're doing, came up time and time again. But they were stuck and they're stuck on this like really hard loop of, well, I've created a lifestyle for myself. And now I can't, I can't just back away from that and identifying what I'm passionate about. Like, how do I even do that? And I've got all these commitments and I'm working 90 hours a week. How can I step across? How can I back away from that to get the mind space to identify all this

stuff? And so I think what I try to encourage folks to do earlier is just to be begin thinking about the framework, perhaps not make those decisions when they're 22, but just have that framework in their head so that as time goes along, they can hopefully, through pattern recognition, spot pieces of different stories that tie together to paint the picture of their passion. But I agree with you. I think when you're 22, 23 years old, you don't have enough life reps to possibly know what you're going to end up being passionate about for the rest of your life. This is really interesting, Ryan.

I didn't actually expect to go this route, but I'm really glad we did because I think this is helpful and can be for people at any age to have these types of thoughts. And it's obvious that you have, you're a really thoughtful guy. And that's why I wanted to talk to you. So let's get into some of your story and what you do and why you do it and then dive into some of your thoughts, whether it's culture, hiring, talent, all of that. So, okay. So when you're at a dinner party and the people there don't know who you are and they ask you to introduce yourself and say what you do, what do you say?

My wife does not like my answer to that. I say that I work at a tech company. I get uncomfortable saying that I'm the CEO. It's a kind of, I get uncomfortable because it's also very hard to talk about unless the other people. are CEOs. It's hard for me to talk about at least. Why? I don't think it's hard for a couple reasons. One, I think the social dynamics in Silicon Valley where I live have kind of led almost every CEO to always say that things are great. You know, I've talked to so many CEOs who told me they're crushing it and then six months later the business is literally closing down.

but it's a really hard town to talk about any challenges. Once you start opening up the commoda to any challenges, then people kind of view that as, oh, things must be really bad if you're talking about that. So that's one. And to be honest with you, it's never perfect. There are always massive challenges. And so I don't like being fake.

So I'd prefer just not to talk about it than to like just say the good stuff or get kind of a side-eyes glance when I talk about some of the challenges. So that's one. Another is because it's kind of one of those topics where I would love to talk about it for two hours. I really struggled to talk about it for two minutes. And 95% of people that ask,

so what do you do? Just want the two-minute version. And it kind of means so much to me that I'd rather just not talk about the two-minute version. So I'd rather just ask them about their life. So my plan wife gets upset when I do that because she thinks that I, and this is true, she thinks that I am robbing other people of the opportunity to ask those questions and for me to like connect with those people, which is true.

And so it's something that I try to work on, but I'm not particularly good at it. So you can do whatever version you want, but I'm asking you, what do you do? What is circle up? What's it about? And what do you do? Circle Up is an investment platform powered by technology. So I founded it six years ago with my co-founder, Rourke. And effectively, what we're doing is we're building a series of algorithms and data sets,

which collectively we call Helio. Helio goes out in the world and finds and evaluates companies. And then we use that information, that knowledge graph, effectively, to invest into the companies, either give them equity or loan the money or credit or to connect them with third parties like large strategic companies. We happen to focus on an industry consumer products and retail companies that is a massive but receives very little capital.

So consumer is an industry that's about three times a size of tech but receives about 150th or 175th investment as tech does at the early stage. investors love this space, but it is really hard to identify the right companies because there is no Silicon Valley, there is no Y Combinator, there is no tech crunch of consumer and retail. Nothing of that scale. And so investors have to fly around the country to network for months and months to find the right company. That math makes a lot of sense if you're going to write $25 million check and a larger company. But typically companies with less than $10 or $15 million in revenue in the consumer space only raise a couple million bucks. And so investors can't reliably or efficiently invest in those companies. So our technology helps to find and evaluate those companies more effectively than humans can do a loan. Why are you guys located there in Silicon Valley? The direct answer is just because this is where Roy and I were living before. But it's a technology.

The reason I ask is just because you said it's a hard town to talk about challenges. Maybe there's better towns to talk about challenges. There are. There are definitely better challenges. There are better talents to talk about challenges. I think this is a difficult technical problem, very, very difficult technical problem. And so hiring engineers and data scientists is core to our success. There happens to be a lot of them here, but there's also a lot of competition here for that talent.

So I think we could have started this elsewhere if we wanted to, but we just happened to be where we lived. Gotcha. Makes sense. So let's talk about how many people work there now? 60 people. And when you started, did you start with just you and your co-founder? Is that how, and you grinded away or how to, what was the very beginning like? We started with my co-founder and I, we raised a seed round. We hired our first engineer, Bryce, who's still here. And, and then started building the product. And first iterations of, of what we did and what we focused

on were very, very different than kind of the current solution. There's been a lot of changes along the way, but that's how we got started. So now you're up to 60. And I mentioned to you before we started recording that, we have a lot of people who are in hiring positions or they will be. They're trying to become in positions to hire others. And you've written a good amount about this that I like and would love to dive deeper. Can you talk about some of the initial mistakes you made?

as a hiring manager or trying to build your company. Yeah, a lot. So we could probably take the rest of the time. So I think probably one of the biggest mistakes I made is it took me too long to create frameworks to make the hiring decision.

I had in my head what I wanted and I never crystallized those frameworks for other people. I think frameworks help people run faster. Frameworks allow two people in the same team to be confident that they're rowing in the right direction without having to breathe down each other's necks. Frameworks prevent micromanaging. If we're following the frameworks, go, just run. And in the case of hiring, you know, I think a lot of people make the mistake of just not kind of crystallizing, well, what are they what are they looking for?

Yeah, I mean, when you say frameworks, do you mean simply documenting what you want and how to get it? Is that what you mean by a framework so that others can say, oh, this is what Ryan wants? He wrote it down. I can read. Or what do you mean by framework? Yeah, so a couple different frameworks.

So one are what are the traits that we look for in a teammate, you know, related to that, like, what are the values we look for? So for example, a lot of hiring managers will say, well, this person was or was not a cultural fit. What does a cultural fit mean? And then I've had, you know, in prior careers or prior jobs, like someone say, well, they don't pass the airport test. The airport test, meaning if I want to get stuck in an airport for five hours with this person, that's never made sense to me. I got some of my best friends in the world would be horrible teammates at Circle Up. It's not, but I'd love to be stuck in an airport with them. And conversely, there's some people that have been amazing

teammates here at Circle Up that we wouldn't have a ton of talk about. We just have a different interests at an airport for five hours by ourselves. So I think crystallizing what we look for in culture is really important. But the framework on, yes, what do we look for as a teammate? Also, framework on just the hiring process itself. Who's on the hiring loop? Who makes decisions? Where do we look? How many interviews are there? Those types of like nitty, gritty things, when it is ad hoc, it is less of a system. There isn't a framework. Then people, move in different directions. When it's ad hoc,

you know, a teammate might decide to hire someone after one interview or two interviews instead of 10. Conversely, another teammate

might want to interview 75 people. When you think you don't need to do that, you can just run. So frameworks help to get everyone row in the same direction.

I think the framework that I've talked a little bit about publicly that I think is just vital is what do we look for in making a decision to hire someone? what are the traits of the person?

And so for us, there are a couple key things we look for. Horsepower, I take intelligence over experience any day of the week, and that's a really important thing for. So horsepower is something we look for. Integrity is a tough one to test for, something that we often ask about. It's like, you know, talk to me about your prior manager, your prior job. And usually when someone is kind of dumping on their prior manager or team manager, or job that's usually a red flag on integrity,

but there's some other ways we test for it as well. Work ethic is another one that we care a lot. If someone has work ethic, integrity, and horsepower, that's usually a pretty darn good teammates. Two other things that we look for are teamwork and pride. And so those things are kind of laid out for the teammates here at CircleUp, both the hiring managers but also the people that are in the hiring loop to begin kind of probing on that.

And so, you know, when you start talking about, like, is it a cultural fit or not, well, let's not talk about that. Let's talk about these specific attributes. If they have these specific attributes, whether the person is an introvert or an extrovert, it doesn't matter. So those are the things we look for. So when somebody interviews, they're always on their best behaviors, the best, for a lot of times it's the best, they're going to bring everything they got, right? And we have gut feelings into intuition to help with that. And I think we build up our gut and intuition. I talked with Liv Boree about this, a professional poker player about how she understands when somebody's lines.

or bluffing. And she says one way to build up your intuition is to get a lot of repetitions like we mentioned before, life reps. So I love those five of what you're looking for, horsepower, integrity, work ethic, teamwork, and pride. And I think that makes a lot of sense. However, how do you gauge somebody's work ethic or their level of pride in the interview process?

I think you tweeted about this, by the way. But I'm curious, how can you gauge this in the interview process? It is exceptionally hard. And by the way, I would imagine that she is much better at it, better at her judging, kind of bluffing than I am. It is exceptionally hard. I think you get better with a lot of reps, like a lot of things in life. We, there are, I think, I think first, though, it starts with making sure everyone's aligned

with that framework. Yep. And so even if you and I are not perfect at identifying whether someone has pride and what they do, the fact that we know we're looking for it, I think, is like 50% of the battle. And that aligning on that first. And also it allows us to align that, you know, it's not important. It's not important whether or not the person is funny. It's not important whether not the person is an extrovert, unless that's relevant for some particular job. Those things are not what's important. So it focuses the conversation. And I find that that allows us as a team

to be a lot more effective at going after that goal than if we don't have that framework. Individually, I'm sure we make mistakes on our ability to identify pride or integrity or other things on that list or teamwork. But when we're, we've got five or six people in the hiring loop in a room talking about it or submitting their feedback anonymously, which is what we actually do. And they're pointing to those traits, that is, that's, that's, a way to like align the conversation and I think eliminates some of the false positives or false negatives. So you know are there questions that we have? Yes there are. They're not particularly

amazing questions. So in the case of pride, we just ask them to talk about something they're proud about. We also ask them to talk about what they've worked on or their team. And you can begin to like identify do they lean forward in their chair? Like how how's their voice? Like does it, you know, What's the passion in their voice? When they talk about their teammates, even if they're leaving the company and they disagree philosophically, are they proud to have worked on something? Are they proud to have been teammates with the people that they were working with, right? Even if the thing didn't work out.

Those are things, if you know you're looking for it, I'm not saying we're perfect at it at all. But I think, you know, after some reps, you get better and better at kind of spotting, trends and the answers. What about that person? And I assume this has happened at Circle All but it's happened for you because you went from essentially having to do all the work as an individual with a very small team. And now you're a manager. You're the boss.

You are the boss. So you probably spend, I'm guessing, but you probably spend more time being a manager than anything else because you're leading 60 people, 59 people. What are. There's somebody listening, like I said, who's about to make that jump from individual contributor to manager. And the reason I talk about this so much, Ryan, is because I will never forget making that jump because of all the mistakes that I made when I made that jump. And I want to help so badly the people in that arena because there's so many that are about to. There's so many that are currently are.

There's so many that did a year ago and they're still fumbling around. So what are some of the pieces of advice if you found a new manager, you see? say, hey, you know, I've been doing this the last few years. Here's some things I've learned from making that shift where I was just kind of working and worrying about myself to now I am leading 59 other people. There's a lot. And I think it's a wonderful thing you're identifying that that is a really big challenge. And I think sometimes people get excited about, wow, I get to manage people now.

Oh, yeah. Without recognizing, like, all of the really big challenges that go along with that. So there are a few things that come to mind for me that I've learned have been important for me and the managers here. So a couple things. First, I know I'm a broken record on this, but just to reinforce like figure out the framework that makes sense for your role and the people around you. And that is particularly important for managers because if they don't have the frameworks right, this is what we're going to do. This is how we're going to make a decision. The clarity on what to do.

Like this is what I do, right? Exactly. It's also what you do, right? So it's what I do what you do. And I think that that prevents micromanaging. I think without that clarity, what happens is you start a quarter or a year. You kind of have a rough idea of where you're going, but it's not really clear, not transparent. And as a result, the two people are kind of rowing in slightly different directions. You extend that out over the course of a month or a year. And over time, they get so far away from where they thought they were rowing that there's a problem.

then the manager has to jump into the team members work and start micromanaging. That would have been prevented with a framework, with a roadmap on this is what we're doing, this is what we're not doing. I think that that's critical. So that's one. I think another is really trying to learn how to develop empathy with your team, whether you're managing one person or 100 people. kind of what is what do they go through on a day to day basis so sometimes sitting on a sales call could be helpful right in a way that's you got to do this in a careful way without micromanaging but like trying to get some understanding of what that person goes through so that as you're making

decisions you're developing the framework you can do it with them in mind that is particularly hard i think for a CEO that's managing either business units or parts of a team that's that he or she has never done. I've never been a data scientist. And so for me to manage a team of data scientists is hard. It becomes easier, but still hard, if I'm able to meet with them one-on-one or a group and get a better understanding of how their day looks,

what they do, what are the challenges and opportunities that they face. I think empathy is a core thing. a third thing that I would say that I have found particularly valuable for me is a resource to talk about the challenges and opportunities of being a manager. That might be other managers like a peer group. I would recommend outside of the same company that you work at so you can be a bit unfiltered. Or it could be a management coach if you have the resources through your company to do that. But it allows you to talk about challenges in a much more vulnerable way than might be. be possible if you talk to another manager or your CEO or whatever.

So those would be some things that I point to. I love that. That last one I would have greatly appreciated whether it would be a coach, mentor, and specifically a peer group. The reason why, Ryan, because one of the things I do in my business now is I host what we call a leadership circle. And this is a group of 12 total people. So we keep it small.

And I facilitate this. It's part of one of the services I offer. and I facilitate it. And none of the people, the one rule is that none of the people can work at the same company. So it's people from all over the country. And similar type roles, not exactly the same, but similar type levels, but different companies. And it's almost, the members tell me, and I feel this way too, they feel like this safe

space because there's the one rule, another rule is you can't take anything outside of the group. Right. Don't publish it. Don't write about it. Don't do any of that. But it's a safe space to share some of the struggles. And you could say it's either happy or sad at times because I learned that there's some people from some incredible companies in this group. But everybody's got challenges. As you've talked about, everybody's got. And some of them are real, real challenges from highly intelligent people. And I think, but it's so helpful that they get to share with each other and have this dialogue and a safe. space and then they get ideas of how to handle some of these situations and it's made the companies where they work better because of it. Yeah. I think being a life, it makes so much sense to me. I love that you do that too.

That's really cool. I think being a leader is a really, really lonely role. And I think that that loneliness can be very unhealthy. And I think we could make it healthier by having folks to talk to who have been in similar positions. Whether or not they're at the same industry, know, the exact problems you're dealing with is less important. Just the concept of like, how do you deal with these types of difficult situations? I find that to be incredibly relieving and cathartic. Do you have a peer group like that? Do you have a coach or what do you do? I have a coach that I go to. I also just started a group of

CEOs just got started recently and they'll get announced. It's kind of an equivalent of like a YPO. So I'm a part of that to when that gets announced later on this year. But it's effectively kind of 12 CEOs getting together once a month to talk about things that are working, not working, whatever. And that's been really, really healthy. I think the coach is helpful too. And I've said this before, but I have a coach to help me with writing, putting a book together based on things I've learned. And I know that I need, I don't think I'm talented enough to do it without the help of someone who's a professional at this.

But what I've learned is that those coaching sessions, they're once a week, those coaching sessions are therapy sessions. They really are. I am just emptying my soul. Everything I've got when I've, what I've learned, what I've gathered, speaking from experience, speaking from what I've learned on this podcast, everything in between. And I am, I'm physically exhausted by the end of them, but I feel a lot better. A lot better about, and I, and I have someone who she's really good at asking quality

questions to get it out of me. And we're, you know, we're making our way and getting it down a paper. And I'm excited about it. But I think it's, even if it wasn't for the practice of writing, it's very healthy to, to be able to have those conversations with, with somebody along the way. Yep. I totally agree. Is that what you're, yeah.

It is funny. For me, my wife is amazing in so many ways, but she always wants to talk about it, about how things are going at Circle Up and the role as a CEO. And she does it in a really, really productive and constructive way. I'm just not always able to meet her. Being involved in kind of this CEO group or going to management coaching helps. me be more effective with her too at home and being able to talk about it in a more productive way because without it, I kind of go home and I've got like this just not of feelings and experiences and it's kind of like hard to unpack it constructively. And sometimes you just need like the hour long management coach like you have therapy dump to be frank. Yeah. Yeah. And that allows me then to go home that night and be a lot more effective in talking to her about like the good stuff and the challenging stuff at the company. Yeah. That's a really good point to put you in a better position for

when you leave. All right. A big buzzword is culture. And you're obviously working hard to build a culture I would imagine to be a place that people want to work. And you tell a funny story about the fact that you bought 60 puffy jackets. And I love it. I laughed. It was really funny. But when you think about culture that you're trying to build. What are, what are some of the keys or actions and mistakes you've made as you're looking to build the culture to be a place where people want to come to work? Yeah. I think some of the good things we've done, it's been a focus on mission and our mission statement is to help entrepreneurs to thrive by giving them the capital or resources that they need. Everyone at the company can recite that and it is not just a line.

It actually informs what we do. That framework. helps. Another good thing I think we've done is really clarify the values that we have and they're unique to circle up. It's not just, you know, honesty, right? It's values that are unique to us. Like what? They're written on a wall. Oh, okay. Here. And that's, that's been another helpful framework, just to inform we hire how we reward people, how we give constructive feedback, what we build, what we don't build, etc. In terms of mistakes, by the way, the values are do it right, be brave and be a solution. And in terms of mistakes, I think one of the big ones is when I would talk about kind of the vision for the company, especially in the first couple of years, I would talk about it and then kind of put it away for a year. And that just did not work. And I could not, it took me years and years to figure out why it wasn't working. I would talk about the vision and then a month later I'd start getting questions.

Hey, I don't know if we have a really clearly defined vision. And in my head, it'd be like, well, what do you mean? Here's the document. I just walked through 30 days ago. Just here it is. Go take a look at it if you have any questions. And I would get frustrated and I wouldn't have, I didn't feel heard. And so I'd put more effort into like this monolithic presentation to walk through our vision.

again. And I just kept missing the mark. And what we changed maybe a year and a half, two years ago, is began to reinforce the vision more frequently, A, and in different ways, B. So it's not just, you know, the one monolithic presentation once a year. It's a more frequent conversation. It's a conversation in different ways, sometimes in front of the whole team, sometimes in smaller groups, sometimes one-on-one. The vision of the company shows up not just for me, but for me and other people, in different channels.

So verbally, but also in writing over email, et cetera. And so we try to reinforce that vision. Our culture took some meaningful hits before we did that. And what it resulted in is people not really sure how things all fit together, because the mission of helping entrepreneurs to thrive by giving the capital and resource that they need, that is nice, but you can do a lot of different things that fit underneath that mission. And the vision is what people needed to help align what they should be working on, what they shouldn't be working on. So we found that when we

weren't reinforcing that vision and when we weren't helping people to see how the dots connected, that they would row in different directions. Then everyone around the table would get frustrated about what was or wasn't getting done, which led to micromanaging or perceived micromanaging from different managers. And that caused problems. So we kind of had this cascading effect because we didn't have the vision. People didn't align around the vision consistently. And so we've made those changes, which has been really helpful.

This is great, Ryan. like every aspect of it. I really appreciate it. Just a couple of quick questions before we take off. Great. What's the, what's the most useful advice you've ever received? That's a really, really interesting question. You know, there's two things that run through my head, so I'm going to say both of them. Okay. One of them wasn't advice from me, or that it was given to me. It was just kind of a, a quote that I just am stealing as advice because it had a big impact on me. I think it was originally said by Winston Churchill, although I probably should be Googling this before saying it on a podcast.

All good. And then I think it was repeated by Hillary Clinton at a commencement address. But the story that I heard was that Winston Churchill stood up and was also giving a commencement address and said, never, ever, ever, ever give up. And then he sat down. And that kind of connects back to the first thing I mentioned around sustained excellence, which is persistence. And that concept is a really, really powerful one for me.

It's also hard because sometimes you need to pivot. Sometimes you actually need to give up. and so it's hard to know when to do that because you don't have the persistence necessary to be successful or when you should be doing it because you're working smart, not hard. But by and large, I have found that that quote, which I steal as advice, has been really helpful. I think the other one that I care or that has had a profound impact on my life relates back to the quote from that basketball coach, which was, you know, to do what you're

passionate about. That was the kind of end of the talk we had. Just find what you're passionate about. And I think that there's a point in your life where you can hear that to your point earlier, and there's an age when it's probably counterproductive. For me, I wish I had heard it, I wish I'd listened to it a bit earlier than I did. But it has, changed my life. And I am just so, so grateful to have gotten the opportunity to change my life and to work on something that I love and something that I'm passionate about. There are days now, it's going to sound corny or whatever. There are days now when I run to work from my car. I park about four blocks away, and there are days when I run to work because I'm excited to get to work.

Really? And it is hard and it is sometimes soul-crushing and everything else. That's difficult, but I also like am really passionate about it and that makes me feel more fulfilled in my life. So those are the two pieces of advice that have really kind of meant a lot to me. Just thinking of that, you mentioned your wife. It sounds like you and I share that trait of being very lucky of finding a great spouse. I'm curious how much of your work do you take home? I mean, both physically like you're on the computer responding to the email because you mentioned that that is a good quality to be able to be responsive.

How many, because I know you've also talked about the importance of getting eight hours of sleep, of having balance in your life. So how do you balance being somebody who's responsive and a good communicator with maintaining health at home? It's exceptionally hard. Yeah. And I wish that I was better at it. You know, our life today is wake up.

We get the kids ready. I've got two kids soon to be four-year-old and a one-year-old. That's about 20, 30 minutes. Then I leave to go to work. I come home, give the kids a bath, read my older one, a daughter. And then I usually do TM Transcendental Meditation for 20 minutes after they go to bed. Get out of that. And then I have dinner with my wife.

But I'm back online. I'm back online at usually from 8.30 to 10 at night, and then I'm asleep at 10. I'm kind of religiously, I desperately need eight hours. I wish that I was better at both being present in my conversations with my wife and giving the conversations more space. I'm proud that I'm trying, but I wish that I was better. Are there, do you have points of contention? Is this a regular topic you talk about? Like, Ryan, let's go.

I know you're the CEO. I know you're working. I know you've got to be online. But we need our space. It's actually a topic that I bring up about 10x more than she does. What does your wife do? She just became, I don't know when this will air, hopefully not today. So she just got the, okay.

She just became a CMO at her company. And that's going to get announced tomorrow. So that's my matter. So you guys are both big time studs at work. So, I mean, that's a lot. Yeah, she's, I mean, she's phenomenally successful. And it's hard.

Yeah, so it's actually something that I bring up. But, I mean, we both have the intention to be better at it. I think that she sometimes gets worried to bring it up because she knows that it, like, it's just, as the CEO, like, there's just sometimes things that rely on you. Yeah. And not that she doesn't have really difficult responsibilities, too, but I think she is worried about being the person to push us to shut the computers off and spend more time together. So it's usually me. Okay.

And I usually am frustrated at myself about that. I wonder if your house looks like mine. So after the kids are in bed, my wife and I often find herself sitting next to each other with our computers working because, well, one, I think we're lucky to really enjoy what we do. So we want to do it. I don't feel like we have to do it. but we want to do it. Is that,

is that, is that how your house looks, uh, 8. Okay. All right. Yeah. It's exactly.

It's exactly. And you're, and for her and I both, it's, we want to be doing it. Yeah. We also want to spend time with each other. Yeah.

And that's, that's hard. So we, you know, we try to do things like carve out time. We go on, you know, trips by ourselves.

Every Friday night, religiously, we have date night without the kids. Nice. Um, but I think we can be doing a better job. And that's mostly on me. In a way,

though, I think it helps to have another intelligent person who cares about you more than anybody else in the world to be a sounding board too. I find that to be, I love that about my wife. And I think it's, I'm very lucky. And I try to do the same for her. And I think, I think that's healthy. I mean, that's a good part. But I'm with you on the getting away from it too.

You can't just be all work all the time. But I think, I don't take that part for granted. I think that we're fortunate to have that, you know. We are so fortunate. I mean, it's, I can, she is smarter than I am. She's brilliant. I mean, Harvard undergrad, Stanford GSB, she's brilliant. And she, I, she helps me with so many challenges and opportunities, but I also feel

comfortable being able to talk to her about anything because I know she, like, she gets it, which is, which is awesome. That's great, man. Well, Ryan, this is great. I know we went a little long, but I really appreciate, um, the conversation. I would love to continue this dialogue as, uh, as we both progress, man. I find someone is thoughtful to you to be, I'm excited just to see all of the growth that

circle up and what you do as a leader as you continue to progress, man. Thank you. Thank you so much for having me on. And thank you for doing this, this podcast, just in general. I think it's a wonderful thing that you're helping to get the stories from leaders and like what works, what doesn't work, helping them to be vulnerable out there. Because I think that's so healthy for other people to hear. So thanks for doing it.

Yeah. And please keep the tweet storms coming. I love it. I'm always on the lookout. Like, I wonder if Ryan's got a 25 tweet storm coming. But it is. They're good, though. They're really good.

How long does it take you to put those together? I'm curious. Are you just stream of conscious going? Or do you really sit back and analyze every single word of every tweet? It depends. Some of them, like the one about the challenges of being a CEO and the mental health one, I really, I spent a couple weeks writing it, to be frankly. Okay.

Because I thought it was, there's some others that I'm really cavalier about that will have a ton of typos. That was one that I thought was, I didn't know how many people would touch, but the people that I thought it would touch, I thought it would be important to write it in the right way and not be cavalier about it. And so it took a lot of time to write that one. Yeah. Speaking of that, where would you send my listeners to learn more about you online?

Circle up or our Twitter account, either Circle Up's Twitter account or my Twitter account. So. What's your Twitter account? Ryan underscore Caldbeck. Perfect. All right, man. Ryan, thanks again for being here. Really enjoyed it.

Great. Thank you so much for the time. All right. Wow. It's evident that Ryan obviously has a lot of horsepower himself, really intelligent guy. I love the frameworks around hiring, around building culture, around values. That was really good. I learned a lot. I hope you enjoyed it. If you did, I would love it. If you would,

write a review, subscribe, and rate the show in iTunes, Apple Podcasts. That's write a review, subscribe and rate it, hopefully five stars in iTunes Apple Podcasts. It really helps spread the message all over the world. Thank you again for supporting this show and giving me the opportunity to do what I love by my passion on a daily basis. It's so much fun. I really enjoy it. All right. I'll see you next week. Can't wait. All right. You still there? I am. Yeah. All right. Thank you so much. That was really good.

Just the depth that you're able to go to on a variety of topics is awesome. I learned so much and I think it'll be helpful for my listeners. I know it will be. It was really good. It's really good. Thank you again, seriously, for doing this for just like the industry of leaders or whatever you to call like the group of leaders because I there's a there's a lot of podcasts that just talk about like someone someone crushing it right and this is this what you're doing is real life and I'm just grateful that you do it so thank you oh I appreciate that that means a lot well I'll um I'll be sure to get back with you and your team when this goes live um we'll we'll send you all the details

but uh I I don't see any edits needed based on on how good you were so we'll probably just slap on an intro and an outro little music and it'll be ready to roll Terrific. Cool. Thanks again. All right. Thanks, Ryan.