Ryan Westwood - Leading With Example, & Mastering Your Niche

(Joel Beasley at 00:00:00) Hello, my friends. Today we're talking to Ryan, the co-founder and CEO of Simplus. And we discuss how to lead with example to reinforce the values of your company, how to find success as an entrepreneur by mastering your niche, and best practices for mergers and acquisitions that Ryan has learned through experience. All of this right here, right now on the Modern CTO Podcast.

(Joel Beasley at 00:00:26) Here we go. This is the Modern CTO Podcast.

(Joel Beasley at 00:00:39) So can you tell me a little bit about your background? Introduce yourself to the audience some.

(Ryan Westwood at 00:00:44) Yeah. So I'm a lifetime entrepreneur. When I was in elementary school, I took my wagon and my cards and went down to a main street in Provo, Utah at a little place called Russ Coin and rented out a kiosk, put little price tags on my stuff, had my Beckett and checked all my cards and started selling cards until my dad finally found me late in the afternoon, kind of upset that I'd left school.

(Joel Beasley at 00:01:17) What kind of cards? Like playing cards or something?

(Ryan Westwood at 00:01:20) Yeah, playing cards. So basketball cards specifically. At the time I was really trying to sell Jordans, and Kobe was a rookie coming up and it was just a lot of fun. So selling cards, and I always had this entrepreneurial spirit. And my dad was a historian and architect, so it didn't make a ton of sense. But my grandfather owned some of the first Greyhound bus stations, owned restaurants.

(Joel Beasley at 00:01:49) Crazy.

(Ryan Westwood at 00:01:50) And was a great entrepreneur. And so it's something that I've always loved and wanted to do. So I've built three companies now, all have become exits. I would say my obsession has been with entrepreneurship. So I've been the entrepreneur in residence at UVU. There's about 32,000 students. I've written a book on entrepreneurship that became a bestseller. I've built three different companies. We've run a public company, private company. We've been in international markets, domestic markets. Our last company grew into four continents. We did seven acquisitions. So I've had experiences on a global level in private and public companies. We've just had an incredible journey with entrepreneurship. I've written for the Wall Street Journal and for Forbes on entrepreneurship.

(Joel Beasley at 00:02:48) Very cool.

(Ryan Westwood at 00:02:48) So basically anything related to entrepreneurship, whether it was writing a book, whether it was being a columnist, whether it was being an educator, being a venture capitalist investor, being an entrepreneur, anything that you could study related to building companies, leadership, and entrepreneurship in every avenue I've tried to do that.

(Joel Beasley at 00:03:12) Wow. That's awesome, man. So what was that last company that you were at where you said you did like four acquisitions and four continents? That's the correct number of acquisitions?

(Ryan Westwood at 00:03:22) That's right. So yeah, four continents, seven acquisitions, and that's my current company, Simplus. We now employ a little more than 800 people, and we are a subsidiary of Infosys. So we're a publicly traded company. We just reported our earnings. We beat both EBITDA and revenue and had a phenomenal quarter. But it's been an interesting journey. We were acquired in the middle of the pandemic on March 13th of last year.

(Joel Beasley at 00:03:57) Oh, that's like right when it all went down.

(Ryan Westwood at 00:04:01) Yeah. So the day the president announced the pandemic was the day that we were acquired.

(Joel Beasley at 00:04:08) Man, that's crazy. What was that like? So you're going through a huge change of getting acquired while also presumably going through the huge change of going fully remote. What was that like?

(Ryan Westwood at 00:04:22) Well, I think this would be a phenomenal Harvard business study, because if you think about this, you have a company based in India and a company based in the United States. So you have two different countries, then you have all the things that come culturally with that. And then on top of that, you have us being acquired and then us having just acquired a company a month before we were acquired. And then on top of that, we did a reverse integration. So the Infosys employees in North America and Australia focused on Salesforce became a part of the Simplus team. So it's not common that you're acquired by a larger company and then they report under your structure. So it was a reverse integration. We were integrating another company while we were being integrated into Infosys. You have the different continents, the different time zones. There's a lot of complexity. When you think about, and then we were a private company getting used to the cadence of being a public company and Sarbanes-Oxley and everything else. So if you talk about adding all levels of complexity all at once, that's basically what we did. And then you have the pandemic and you have everybody in this situation where people don't know what they're going to be doing in the future and what's going to happen with COVID-19. So yeah, it was an interesting year and leading the business through it, I learned a lot of really important lessons.

(Joel Beasley at 00:05:57) So what was your day to day like during that time?

(Ryan Westwood at 00:06:00) You know, at first we were trying to figure out what the impact was going to be, what customers were experiencing and how it was going to impact our overall numbers in our business. So that was pretty complex, just getting through that. Then it was stabilizing the business and talking to the employees about our plan. How were we going to handle the pandemic? How were we going to work through it? And making sure everybody felt like a sense of confidence that things were going to work out and go well. So I think first of all, you've got to assess the situation quickly. And then second, you've got to stabilize the business and give everybody confidence that you know how you're going to react. We didn't know the full extent of COVID and what the impact would be. So every day we were trying to gather as much information as possible on what the impact would be overall. So day to day, we were trying to gather information, stabilize the business, a lot of communication. You know, one of the big beliefs I have is that as a leader, you've got to communicate things at least six or seven times, important messages. Now, oftentimes we pat ourselves on the back. We tell our employees something, whether we're running a nonprofit or a church organization or a company, it doesn't matter what it is. We don't communicate nearly enough usually. And so we were constantly, I was on Slack, I was on company meetings, Zoom meetings, everywhere I could be to possibly communicate. You want to be communicating in the business. And so, and then we started running a special meeting for COVID where we had a weekly update. And I think one of the things that gives employees a sense of confidence is when there's a lot of transparency and clarity around things.

(Joel Beasley at 00:07:51) Absolutely. Yeah.

(Ryan Westwood at 00:07:52) When you don't have that transparency and clarity, people get worried. So we just started running a weekly meeting where we had a town hall and people asked me questions. I presented and we discussed the plans for that week with the global company. Now, we had been in a cadence. We would maybe have one and possibly two meetings during the month where it was a global meeting and we moved to a weekly cadence.

(Joel Beasley at 00:08:19) Was that like an all hands on?

(Ryan Westwood at 00:08:20) It was an all hands meeting every Friday with everybody in the company. And by doing that, it increased the communication between us, and I think it made a big difference during the pandemic.

(Joel Beasley at 00:08:35) Yeah, that makes sense. So to give the audience a little bit of context, can you explain just what Simplus does?

(Ryan Westwood at 00:08:43) Yeah. So we help people with their journey with Salesforce.com. So if you purchase anything on the Salesforce platform, which has now become many different things, we help hold your hand through the process of implementing and getting the business value out of the platform. We specifically made a name around helping companies automate their quoting process. So say that you are Mitsubishi and you've got tons of different SKUs, products, and services, and you want to make sure you get pricing out to customers in a timely manner, we help make that process possible.

(Joel Beasley at 00:09:24) Got it. Cool. So you're like a digital transformation partner specializing in Salesforce.

(Ryan Westwood at 00:09:31) Exactly right.

(Joel Beasley at 00:09:32) Cool. Is that what Simplus always has been since you started it, or has it changed over time?

(Ryan Westwood at 00:09:38) Oh yeah, it's definitely, you know, the way I look at entrepreneurship, and this is kind of interesting. You're trying to feel your way through the, especially the really early stage of your business, feel your way through it and decide where's the right opportunity. And you kind of look at it like a running back in a football game. Running back is sitting there and they take the snap and they're looking for grass. They're looking for an opening and the offensive line breaks open a hole and you take off. And a lot of times you're behind that offensive line and you're just looking for any air, you're looking for anywhere you can go. And so, you know, the early days we were looking at integration platforms, building an integration platform. We were partnered with a company called Workfront, Domo, and Salesforce. So we were trying to figure out who we were. Once we figured out that we were going to focus only on Salesforce, it made all the difference. And I can actually share the story. It's kind of one of those war stories in entrepreneurship. And I think actually teaches a lot of good leadership lessons of how we came to become Simplus. But to answer your question, we were not a quote-to-cash Salesforce business when we started. That has been, there's been a lot of growth to get there. And that was the hole we found in the line to go score touchdowns, but that's not how we started.

(Joel Beasley at 00:11:09) Very cool. Well, can you share that entrepreneurial war story with me?

(Ryan Westwood at 00:11:13) Yeah. So what was interesting is we had taken an investment from the CEOs of Workfront and Domo, and they had supported us. And we had intellectual property where on the AppExchange, we had built their AppExchange integration to Salesforce. So we have shared intellectual property between us. We have the CEOs of the companies investing in our business, and I've made this decision that we're going to cut over and we're only going to do Salesforce. So as you can imagine telling a CEO you're no longer going to bet on his business after he's invested in your company, that's a difficult conversation. We also had, I had my investors who I was about to call and say, "Hey, you know how we built this nice little $2 million business, a million of this, we are going to completely walk away from." So investors, we're going to cut 50% of our revenue. Employees, we're going to let go of half of you. You know, there's 38 of us and 18 of us we're going to let go of. And by the way, investors. So it was like, I was going to upset my investors, my employees and my partners all in one slug. And so I was up. I did not sleep much that month. I was super concerned about it, but I had this view that if we would just focus on Salesforce, we could accelerate the business. So luckily we had very supportive investors and they said, "Look, we trust your vision, the leadership of the company, keep going, and we'll support you." We made the decision that one of the big values that would matter most to Simplus is stewardship. And that meant that we cared about our employees. We care about our customers. We care. It's more than accountability. It's actually really caring. And so I just talked about that value coming out and telling our employees we're letting them go is not exactly showing good stewardship or caring right after that. So what we decided to do is we got a credit line at the bank and we personally guaranteed it as the founders. And we maxed that credit line out. It was a $250,000 credit line. And we floated those employees till they found jobs. And then we actually helped them get jobs. Many of them became employed by Domo and Workfront directly. We talked to the CEOs, we got them jobs, but we maxed the credit line. At that point, when I said that our values meant a lot to us and that we were going to live it, it wasn't like when you walk in, say you go into a Discount Tire store and there's up on the wall 13 values. And you ask the employee...

(Joel Beasley at 00:13:59) Yeah, just a bunch of buzzwords.

(Ryan Westwood at 00:14:01) A bunch of buzzwords. And you ask the employee, "What are your values?" And they go, "I don't know what that is. It's just on the wall." In this case, we picked a few and we were serious about living them to the tune of $250,000 in debt. And so what happened, what I really underestimated when our employees saw that our actions actually met what we said, it was transformational. And so the revenue that we thought would take a year to make up by focusing on Salesforce took about three months. Within three months, we'd made up the million. We'd started hiring again. And about half of those employees, we'd been able to hire that amount back. Focused on Salesforce and we got very, very hyper-focused and it was a lesson for me as an entrepreneur, you want revenue, so you want to do more and more. And it's actually counterintuitive when you really understand entrepreneurship, it's better to get in a sub-niche and get very focused and get very, very good at something before you expand. It's not that you can't expand. People will say, "Well, look at Amazon." Yes, Amazon is an enormous company so they can expand. But when you're a startup, make a name doing something really, really well and have the discipline to stay focused at it.

(Joel Beasley at 00:15:26) Yeah.

(Ryan Westwood at 00:15:26) So in that experience, we made up that revenue and then we started to really take off. And then we looked at Salesforce and said, "Let's only do one piece of Salesforce." And so we bet on their CPQ product and we started ignoring everything else. And we became the best in the world at CPQ until we were signing $15 million engagements at Google. So the lesson I learned is less is more and hyper-focus as an entrepreneur. Now we started expanding at about $50 million in revenue is where we started to say, "Let's do other things." But the first $50 million was on a sub-niche of a sub-niche.

(Joel Beasley at 00:16:06) Wow. Man. I mean, it makes sense. In your reference to Amazon, they didn't expand to be a ton of different business units at first either. They were just a bookstore. Books. So yeah.

(Ryan Westwood at 00:16:20) Yeah, yeah. Yep. Dominated that. Yeah. You're exactly right. That philosophy works. They dominated books before they tried to dominate every consumer product on Earth. But I think people now look at them and say, "Okay, that's what they did," but that's not how they became who they are.

(Joel Beasley at 00:16:38) Exactly. Yeah. You said you had 38 employees at the time, and now you're at over 800 employees. And you're talking about how important those values are to you. How did you keep those values in place and at the forefront of your business as you grew so massively? You said the company is only like six years old, right? That's very fast growth.

(Ryan Westwood at 00:17:02) Yeah, yeah. Now we're just over seven. What I would say that's interesting about this is it takes a lot of work. And I'll give you an analogy to understand it.

(Ryan Westwood at 00:17:13) Most leaders, you go to business school and you learn about strategy. You learn about, you might learn about marketing or finance, accounting, but the soft skills of building company culture and values and leading people in a way that inspires them—not a manager who tells people what to do, but a leader who inspires people to do more and be more and go after something bigger than themselves. In order to do that, it takes a ton of work. And I like the show.

(Ryan Westwood at 00:17:46) I Love Lucy. And this is super retro. I'm gonna take you back. And on the show, Lucy's looking for her earrings and she's looking around on the floor, and her husband walks in and says, "What are you doing?" She says, "I'm looking for my earrings." He says, "Where did you lose your earrings?"

(Ryan Westwood at 00:18:03) And she says, "I lost them in the front room." And he says, "Well, why are you looking in the back room?" And she says, "Because the lighting is so much better in this room." What the tendency for most executives is, is to go where the lighting is good, where they feel comfortable, which sometimes is behind a spreadsheet, which is sometimes behind a marketing campaign or on a profit and loss statement. This culture stuff is difficult.

(Ryan Westwood at 00:18:33) It's the stuff in the room that doesn't have all the light. It's a lot of work to operate a business with a healthy culture. And so I think many leaders also haven't been—they don't quite understand how to do it. So here's some tips. Here's some things that I believe build great company culture.

(Ryan Westwood at 00:18:54) One is if you are a founder or CEO and the values of the company don't match you personally, and you can't live them in a raw sense, you know, there's companies—I was a part of a company fifteen years ago, well, maybe not quite that much, where the CEO talked about working hard and playing hard all the time.

(Joel Beasley at 00:19:18) Yeah.

(Ryan Westwood at 00:19:18) Had this awesome picture on a longboard, him having so much fun. And then I remember one day it was 4:30 on a Friday. I'd closed this big deal. I was exhausted. One of my employees said, "Hey, will you pick up and play some ping pong with me?"

(Ryan Westwood at 00:19:35) And so we started playing ping pong and he gave me a look of disgust. And that was this moment where I was like, wait a minute, work hard, play hard. He says that—he does not mean that. And he lost me. He lost me as a leader.

(Ryan Westwood at 00:19:50) So the first thing is you can never trump your personal actions. People watch you, and you have to realize when you're a leader that everyone is watching you. And that if those values aren't true to who you are, that'll eventually expose you and people will lose interest in following you as a leader. So when I talk about stewardship or caring, if I'm a jerk and I'm talking about caring, it doesn't go so well. Or if I tell the company we work hard and play hard and the second somebody who's been working really hard plays hard, you shoot them a bad look, sends all the bad signals. So the first thing I'd say is you as a leader have to genuinely believe in those values and live them personally. And I think that's where there's a lot of mix up. The second thing is I don't think more than three or four, maybe pushing it, is enough values that people can still remember them all and live them. When you get to this five, six, seven, eight, who wakes up in the morning and chants seven values?

(Ryan Westwood at 00:20:59) You know, our three values: underdog spirit, critical thinking, and stewardship. Very simple. Everyone in the company knows them. All 800 employees, they'll tell you right away. These are the three values.

(Joel Beasley at 00:21:14) So can you tell me about that underdog thinking a little bit?

(Ryan Westwood at 00:21:18) Yeah. So underdog spirit, you know, to me means that no matter what level we're at, there's always more that we can achieve, and we're gonna be tenacious. And we're gonna fight, and we're gonna work hard, whether it's winning a deal or taking care of a customer, we're gonna display that underdog spirit. And we have that underdog spirit as much today, 800 employees, as we did in the early days when we had nothing. And so that value is core to our business.

(Ryan Westwood at 00:21:51) But the other thing is I have to be talking about it all the time. Yeah. I have to be living it. And all of our rewards are centered around it. We have the Underdog of the Month. We have the Stewardship Award where it's all about caring, and we've custom built awards around our values. Our company meetings, we talk about those values. When I'm in meetings, I call out those values and when someone's living it, I call it out. So it has to become something you really, really embrace and live in the day to day of the business. This can't be something you just announce to your employees and put it on the shelf.

(Ryan Westwood at 00:22:32) It's now a part of you and the business, everywhere you go, every meeting you go for as long as you run the business. And those values don't change.

(Joel Beasley at 00:22:44) Yeah. And I think we can boil it down to—you started this call talking about how important it is to over communicate and, like, communicate things over and over again. And when you are living those out and people are watching you, that's a form of communicating them again and again. And those, like, giving out awards for each individual value on a monthly basis, that sounds like a great way to keep in touch with that. So I'm just curious. How do you evaluate the overall health of the company culture and check in on how these values are being adopted and lived out by your employees on a day to day basis?

(Ryan Westwood at 00:23:25) You know, when I started hearing about stories of people living our values and I wasn't involved, and it's like a groundswell and you—I get a call and I hear so and so got cancer in the Philippines. And so we created a GoFundMe and we funded his treatments and he's now cured from cancer. Well, the culture's working. People care about each other. Our employees care about each other and I'm not even involved in that conversation. Or I find out that we have this employee in New Zealand flying into Salt Lake City, and this employee wants to ride on a Harley.

(Ryan Westwood at 00:24:04) And one of our employees in Salt Lake borrows a Harley from his brother and picks him up from the airport to ride in the Rockies. When I start seeing that everywhere, that people are actually caring about each other and living our value of stewardship, then I know that it's happening and you start to see it in Slack. You start to see it on LinkedIn posts. You see people constantly talking about, "Man, I've never felt so cared about by my other employees and counterparts as I do now." So I would just say that I can feel it. I can see it. It's everywhere that I go. When that starts to slow down, you notice there's a little bit of a momentum shift. I also have a group of individuals I call the Change Champions. And every month I meet with a group of kind of culture ambassadors in the company, and I ask them how we're doing and get feedback.

(Ryan Westwood at 00:25:00) And I've done that every month, you know, for years—for five plus years we've been running this group—and it helps me keep a sense of how things are going and understand any water cooler talk in the business.

(Joel Beasley at 00:25:17) Wow. Man, are you guys recruiting? I'm sure people are listening to this and being like, wow, I wanna work somewhere where everyone cares about me and I care about my coworkers.

(Ryan Westwood at 00:25:27) Yes. We are hiring. I believe in this last quarter, we hired nearly a hundred people. So we are hiring and have tons of open positions. So check us out. Go to our career page on simplus.com.

(Joel Beasley at 00:25:42) Very cool. So something that I like to ask about when I'm talking to someone that has recently gone through a merger and acquisition is, at what point did you notice people stopped saying us and them referring to Simplus and Infosys and started just saying we when referring to anyone, whether they're from Simplus or Infosys?

(Ryan Westwood at 00:26:08) That's a really good question. And the honest answer is that takes a long time.

(Joel Beasley at 00:26:13) Yeah.

(Ryan Westwood at 00:26:14) And there's a lot of complexity to that. And because we're doing a reverse integration, we have these Infosys employees joining us, but we're also still a subsidiary of Infosys. And we're in the thick of that. We're now Simplus, an Infosys company. So that's helped.

(Ryan Westwood at 00:26:30) I think the branding piece helps. I think it comes down to the leadership at both the parent company and the company being acquired and them being able to come together at the top. The dominoes fall once those groups come together and all that can happen. And I think also people underestimate the structure of the acquisition—in the merger agreement—can have a heavy impact on when and how that happens. And we're still in the thick of making all that happen in that process.

(Ryan Westwood at 00:27:00) You can imagine the amount of change management and all the things that we're trying to navigate to get to that place.

(Joel Beasley at 00:27:07) So what was the earliest acquisition you went through?

(Ryan Westwood at 00:27:12) The first acquisition we did was a company in the Northwest. We were trying to get a presence in the Northwest and they had a focus on billing software on the Salesforce platform, and we wanted to expand our presence. A lot of the acquisitions we did, they were for picking up either a capability or a region in the world we weren't at. So we kinda dotted—we did the Northwest and then we did the Northeast and the Southeast and the Southwest and the Midwest. And then we went to Australia and we went to London and Ireland.

(Ryan Westwood at 00:27:49) So every one of our acquisitions was to expand the company into a new region we hadn't been in before. But the first acquisition we did, we were probably about two years into the business.

(Joel Beasley at 00:28:01) Wow. Okay. So that was pretty early on. So what would you say are some of the efficiencies you've observed that you've gotten better at over time going through several mergers and acquisitions?

(Ryan Westwood at 00:28:17) Okay. So, you know, we kept a list of lessons learned and with each acquisition, we got better and better at it. I would say that we improved and became more and more efficient with each one. But I think that there's a set of key things that we did that made those successful. A couple no nos to never doing an acquisition is you do not want, when you acquire the company, if your benefits or a 401k or whatever else is not as good or better, you're gonna see a big spike in attrition.

(Ryan Westwood at 00:28:48) Right? So you have to be careful about aligning compensation packages. A little nuance is like when that employee that got acquired had an annual review coming up, say it was in February, but the company that acquired you does them all in March. Are you paying attention to the details to make sure that employee gets their annual review when it was promised to them by the prior company? There's lots of little nuances.

(Ryan Westwood at 00:29:16) And again, it comes down to your values. Do you really care? And in our sense, and our values, we showed those people that we cared about them and we accommodated them. So in that sense, we knew those employees, maybe they had a different time where they had an annual review. We figured it out, then we put them into our process.

(Ryan Westwood at 00:29:36) Right? So there's a lot of little details that you have to pay attention to, and you always have to be talking to employees about how you're better together. You know, you have to be able to communicate. This is why we did it. And this is how we're going to be better by combining.

(Ryan Westwood at 00:29:53) And so if you don't understand that and you can't articulate that clearly to employees, that will be very troublesome.

(Joel Beasley at 00:30:00) Have you written about any of these lessons in your writing on Wall Street Journal, Forbes, or your book?

(Ryan Westwood at 00:30:07) We have written a few articles in Forbes about M&A and about lessons learned from acquisitions. But it's been a while, and I have not written a book, but have written a few articles.

(Joel Beasley at 00:30:23) That's very cool. So what was your book about? You said at the beginning that you wrote one.

(Ryan Westwood at 00:30:28) Yeah. So the concept was, I remember being in our second company and we were trying to become profitable. We were approaching break even. We were making a big move to be profitable. And we had a hundred plus employees and I was extremely stressed.

(Ryan Westwood at 00:30:51) And I remember thinking, you know, we're in this small little sublease, we're struggling to make payroll. You know, we're growing, but this is really hard. And I can't, I don't really feel like the success that I thought I would at this point. And I thought there's more I need to learn. You get to certain plateaus in your career and in your life.

(Ryan Westwood at 00:31:15) And I think it's critical that you find people that are ahead of you, that you get in front of them and you show them you care about them and you listen to them. And so this is a way for me to do that. Basically, what we did is we pulled the list from Dun & Bradstreet of 2,000 entrepreneurs that had built a company of a million or more in revenue.

(Joel Beasley at 00:31:38) Oh, cool.

(Ryan Westwood at 00:31:39) And I sat on the phone, me and a few employees, and we interviewed all these entrepreneurs and we took the summation of those interviews. And we created a book on the five characteristics that stuck out for those most successful entrepreneurs. And that's what the book—it's five chapters about those five characteristics. And I'll just take you to the top of it. The number one characteristic was vision, the ability to see the future and then reverse engineer the steps and then lead people to that place and help them get there was the number one differentiator between an entrepreneur that succeeded and one that didn't.

(Joel Beasley at 00:32:23) Gotcha. Yeah. That's actually kinda how this podcast started. It was our founder, Joel, was interviewing a lot of tech leaders just because he wanted to expand his network and learn how to become more successful because he was a software developer that was writing a bunch of code and watching all these other people around him achieve higher levels of success while he felt he was writing better code, you know. So he realized the reason behind that was that they just had better networks.

(Joel Beasley at 00:32:57) So he started interviewing people more successful than him, and people started telling him to turn it into a podcast. And also along the way, a book came out on those interviews as well and a leadership development platform from all of the learnings that come from talking to all these successful people, where we license some of their content and have trained leaders around the world just based off of candid conversations with successful people. And, yeah, that is just such a powerful, powerful thing and format where when you're just talking to someone candidly, that's where a lot of the best insight comes out.

(Ryan Westwood at 00:33:41) Well, absolutely. And I have to say that in all the different forms of learning, to me, you know, when I did this, I interviewed 60 plus different entrepreneurs, CEOs, whether it was for Forbes and whether it was an Oracle executive, you know, and some of the biggest companies in the world all the way to startups. And the things I learned during that time, I would say, I think I condensed a decade of my career into one year and it made an enormous difference in my life, my mindset, and my skillset. And so, you know, I think second would probably be books. I like to read biographies as a strong second to study people and successful people, but I think it's an incredibly powerful way to learn.

(Joel Beasley at 00:34:31) Yeah, absolutely. When you're talking about learning and leadership lessons, if you were to design the perfect leadership training program for your direct reports and the leaders at your company, what would the top couple concepts be?

(Ryan Westwood at 00:34:48) You know, I do do a leadership training for all the leaders at our business.

(Joel Beasley at 00:34:52) Oh, very cool.

(Ryan Westwood at 00:34:53) To me, at this point in my career, my belief is that a lot of my mission is to create other leaders. I'd love to see leaders all over different companies. You know, at the end of my career, I'd love to be able to point at hundreds of companies and say, "Hey, you know what? I worked with those people, those incredible leaders." And that's the impact that I want to have. I'd love to—you know, hundreds. I really want to set my sights high there. A couple things that I've learned: one is that there's no more powerful leadership than leading by example. People try to dance around that concept, but at the end of the day, you have to be the type of person people want to follow. And you have to live the values.

(Ryan Westwood at 00:35:37) You know, I had another situation where I had a boss who would check in with me and make sure that everybody—he would check the phone system to see when people logged in. He would roll in at 10:00, and then he would chew out employees who rolled in at 08:03 or 08:04 on the phone tree. To me, that's the kind of leadership that we can do without. You've got to have leaders that—he should be there at 07:45 if he wants you to be there at eight.

(Ryan Westwood at 00:36:02) So the first thing I would say is your example. I talked a little bit about communication and my belief around communication. You have to be a great communicator in order as a leader to help everybody see the vision. Another area is clarity. Far too often, leaders do not provide the substance and the clarity necessary for their businesses or organizations to succeed.

(Ryan Westwood at 00:36:27) And then what happens is silos creep up. People start to gossip and they start to talk about the business, and they lose faith in the vision. So it's the job of a leader to provide absolute clarity and a definitive plan for everybody to achieve the goals. And then I would say last would be vision. You have to be able to help everybody see a big, big vision and a big goal, and help them understand how they're going to be a part of it and what's in it for them to actually achieve it.

(Joel Beasley at 00:37:00) What's the vision right now? The future at Simplus.

(Ryan Westwood at 00:37:04) Oh, we want to do a billion in revenue. And so we want Forrester, Gartner, IDC to see us as, you know, visionaries in the top right of the Magic Quadrant. We want to have 300 enterprise referenceable customers. We want to be able to do a billion in revenue, you know, and we're on our way. You know, we're bumping up against 400 million now.

(Joel Beasley at 00:37:28) That's amazing. And when you get there, I'll say I knew you when. So one thing that I saw that was pretty cool is Simplus rolled out a vaccine management solution. Can you tell me a little bit about that?

(Ryan Westwood at 00:37:44) Yeah, it was pretty incredible. We created a solution that helped manage the process of actually providing the vaccines. And we focused on certain state and local governments and helping them get it out and helping people schedule times, helping people get reminders, keeping track of which vaccination they had, how to get the second vaccination, and really just making the process much smoother. And building that platform, we built it in a rapid period of time during the pandemic.

(Ryan Westwood at 00:38:16) And, you know, it's been a lot of fun to see that roll out in certain states here in the US and international.

(Joel Beasley at 00:38:25) So what were some of your strengths as a company that made you the right people to go about doing that?

(Ryan Westwood at 00:38:32) You know, I think that it goes back to our caring culture. You know, our employees—they care, and they care about our community. And they started thinking, "How can we help?" Well, the way we can help is we understand the Salesforce platform and we can build anything on that platform. So why don't we build a vaccine management solution, make a difference in the world, and sell it? And it's good business.

(Ryan Westwood at 00:38:54) It's living our values. And that's the kind of stuff that happens on its own when you have real core values. That stuff just happens organically, and you as the CEO get a lot of credit. But I don't deserve credit for that. It's because our employees were living their values.

(Joel Beasley at 00:39:12) That's awesome. Yeah, I just—I didn't think about, like, obviously in the news you're seeing that there's a lot of challenges with the vaccine rollout, getting it out to millions and millions of people. My first thought wouldn't be, "You know who can help? Salesforce."

(Joel Beasley at 00:39:27) But yeah, and their platform. That's just really cool to see how every nook and cranny of the world can do their part to come together for something like that.

(Ryan Westwood at 00:39:40) Absolutely.

(Joel Beasley at 00:39:42) So I also wanted to ask you a little bit about your investing, because you said you've done some venture capital stuff with startups. What are some things you look for in a startup that are really positive? You're like, "Wow, I need to get in on this."

(Ryan Westwood at 00:39:59) Yeah, I've learned a lot of really good lessons. And I've learned them through my failures. And so, you know, you have certain successes and then failures as an investor. The first thing that I learned is I'm an entrepreneur and an operator. That's my full-time job. So at any stage in my career that I've invested, whether it was six, seven years ago or today, you know, that's not my full-time job. And so I need to understand that and have a certain sense of humility about that. The next thing that I learned is it makes sense to invest alongside institutional venture capitalists. And the reason for that is you do start at a later stage.

(Ryan Westwood at 00:40:44) So you're not a seed stage investor, usually, or pre-seed, because you're investing alongside a venture capital firm that's putting a substantial amount of capital in. What I like about it—you lose some of the upside because you're not involved really, really early, but you decrease risk because now they're well capitalized and you have an institutional firm that is asking them for mandated audited financials. So now the financials are tighter. They're more accurate.

(Ryan Westwood at 00:41:17) You also usually have a stronger management team, and they manage the investment. My job is to be an operator. I don't want to be calling entrepreneurs asking for their financials and bugging them.

(Joel Beasley at 00:41:28) Yeah.

(Ryan Westwood at 00:41:29) I know already how hard it is to build a business. Last thing I need to do is be that person. So the tip that I would give is invest alongside professional investors who look after your investment.

(Joel Beasley at 00:41:43) That makes sense.

(Ryan Westwood at 00:41:45) It makes a significant difference. The second thing that I look for after seeing that they're going to be capitalized and they have an investment round is an entrepreneur or founders that I truly believe in, right? Especially at that early stage, do I believe that they have the fortitude, that they have the vision, that they are going to be able to put it all together to create that success? And usually if I love the founder and they have an institutional investor—they meet those two criteria—my propensity to invest is very high. And I focus on enterprise software primarily as an investor.

(Joel Beasley at 00:42:25) Right. So what are some red flags that if you see, you're out?

(Ryan Westwood at 00:42:30) You know, I think one of them I mentioned, which is—and I don't know if it's necessarily a red flag—but if they're not at a place where institutional investors are involved, I get invitations where they want me to invest pre-institutional investors. Like if they have angels but no institutional investment, that's a reason I would back out. You know, I wouldn't be involved. And another one is, and this I see all too often, the founder's face is on everything instead of the brand.

(Ryan Westwood at 00:43:04) So instead of it being Simplus, it's just constantly the founder, right? And to me, if you're not ready to put the brand first and put your heart into promoting that brand and your employees first, you're not ready to be that kind of founder that takes a business to the next level, because it's still about you, right? If you want to do that, go write a book, go speak.

(Ryan Westwood at 00:43:30) If you want to build a great company, focus on the brand and the company and the organization. And so when I see a founder who's still trying to promote themselves above the company—because if entrepreneurs would realize that if they focus on the company and its success, there's a certain level of success that the brand association brings with it. If you built Pepsi and you're the CEO and the founder, your brand is going to be just fine if you focus on Pepsi. But founders want that. They want to keep their ego high real early on before they've built something, and they want to start telling people how to build the business before they've built the business. And so my view—it really turns me off as an investor when the founder seems more preoccupied with their personal brand than the company's brand.

(Joel Beasley at 00:44:28) And that's hard. It takes a lot of humility to be able to take that step back as you're working so hard and putting everything you have into building this company. Like, I can see the desire to want to have some recognition for that. But that totally makes sense. Like, if you really truly believe in what you're building, you'll just have faith that the company itself and the brand itself will lead you to that level of success you're looking for.

(Ryan Westwood at 00:45:00) Yeah. And if you go to the Forbes list and you look at the wealthiest people, every one of them is associated with one big brand they built. You know, you think of Warren Buffett, you think of Berkshire Hathaway, right? You think of these people—they've all built—you think of Tim Cook, you think of Apple, right? They built these big companies, and that's where their successes come from, is the organizations they've built. At the end of the day, as an entrepreneur, it's hard to really rally and respect somebody who's telling everybody how to do something in a craft that they haven't actually done it at that level.

(Ryan Westwood at 00:45:36) And so even if you're good at self-promoting, at a certain point, people will be exhausted by it because they'll realize this person hasn't actually done what they're teaching everybody to do.

(Joel Beasley at 00:45:50) So you mentioned you learned a lot of your lessons as a venture capitalist from early failures. Can you tell me about one of those and what you learned?

(Ryan Westwood at 00:45:59) Yeah. I had a business that I gave some capital to, and the founders didn't have institutional investors involved. And I was focused on building my business, and they ran through the funds and they did not succeed in growing the venture. And so it was one of those things where I was like, "Man, I can't look after it. I can't dive in and change the business. I'm running my own company. So I'm not going to be able to do that, and I can't look after the day-to-day of this business." And that was when I learned, "You know what? It makes so much sense, unless I'm going to become and dedicate my life to the craft of only investing, I should probably partner with people that are."

(Joel Beasley at 00:46:42) Right. Yeah, I mean, it makes sense. It's just you have to have a really high level of self-awareness of the amount of bandwidth that you're going to have as an investor, the amount of time you're going to be able to put into it.

(Ryan Westwood at 00:46:56) Yeah. And, you know, what I have found in life is if it's my main thing, the main thing is the main thing. And if it's the thing I'm focused on, then I'm going to make sure it succeeds. If it's ancillary, if it's the third or fourth or fifth priority in your life, how much impact can you have? Even if you have bandwidth, how much impact can you truly have if, say, you have a family and you have a big company and you have this nonprofit you're involved in, and then you have five investments?

(Ryan Westwood at 00:47:30) Okay. What level—and then you split your time at those five investments—what level of actual energy and momentum can you bring to those companies, being realistic about it? The answer is you will do very little. And so you have to be real about that and understand that unless you're a full-time investor, it doesn't make a lot of sense for you. You're not going to be the person that steps in and saves their companies. You don't have the bandwidth or the opportunity. Very, very rarely would I say you would have that to be able to do it.

(Joel Beasley at 00:48:07) As we're starting to wrap up, what would you say are you learning right now as a leader?

(Ryan Westwood at 00:48:13) You know, I think that it's an interesting time with the pandemic and all the pressures going on. But one of the things it did for me is it helped me to maybe let off the pedal a little bit. I've always been very, very driven. And since I was a young man, I had this vision of building a big company and selling it. And it was like this tiger that I had to go fight. It was one of those things in life that I needed to do. And since doing that, I have slowed down and spent more time with family and other things. And the realizations that I've had is that by letting off, sometimes I find I gain more clarity as a leader. I actually learn things. And by not being in the middle of work, I can be a better leader. And I'm learning to have more discipline around balance and time away from the business.

(Ryan Westwood at 00:49:11) And I'm finding that it's actually helping accelerate the company instead of decelerate. So one of those lessons—it's something I, you know, there's those things in life where you know it's right, but you're not quite ready to live it. So there's certain leadership principles, and you say, "Yeah, that makes sense. It's great." But you're not fully ready to embrace it as a human being. It could be a lot of things. You could say, "I know exercising makes sense, but I'm just not ready to get off this couch." For me, I knew that that balance would help, but I wasn't ready to fully live that until this last year.

(Joel Beasley at 00:49:48) That's really powerful stuff, man. That makes sense. I think everyone has those things in life where—like you said, it could be anything like exercise or eating right or leadership tips you're reading in a book right now. Yeah, everyone's got those things that they're like, "Yeah, I know that's true, but, you know, I just—it doesn't work for me right now," blah, blah, blah. And everyone's got their excuses, but yes, maybe sometimes it takes something as extreme as a worldwide pandemic to give you the chance to step away, reevaluate, and realize, "No, let's finally implement this for real."

(Ryan Westwood at 00:50:25) That's right. And I hope we all had some moments during the pandemic where there's maybe some reflecting we did, and it changes the trajectory of our lives.

(Joel Beasley at 00:50:33) For sure. So I know you guys have an offering for our listeners if they want to go to Simplus and sign up for a Salesforce optimization check call. We want to make sure we get that out there. Is there anything else we want to get out there before we wrap up here?

(Ryan Westwood at 00:50:48) No. Thank you for your time. It's great to be a part of your podcast. I wish you all great success.

(Joel Beasley at 00:50:54) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn or send me an email: [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.