192: Overcoming Setbacks and Seizing Mega Deals: Rich Strobel's Success Story at Smart Data Solutions

0:08 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram. Today on the Sales Success Stories podcast, my guest is Rich Strobel. Rich is the top sales performer at Smart Data Solutions in Minnesota. Welcome to the show, Rich.

0:33 Rich Strobel: Great to be here, Scott.

0:34 Scott Ingram: Really quick, obviously we're going to start off with that immediate value like we always do and get into the top 3 things that you believe have contributed the most to your success in sales. But first, before we even do that, I'm going to give a quick thank you and shout out to Amber Deibert, who was kind enough to get us reconnected for this. So thank you, Amber. And with that, Rich, let's get into your top 3.

0:57 Rich Strobel: Thanks, Scott. And Amber is incredible. If your listeners have not joined her newsletter at the minimum, let alone worked with her, Strongly recommend it. It's a big part of why I've been able to do what I've been able to do. So top 3 for me, I think number 1 would be tactical empathy, which is a term that I grabbed from a book called Never Split the Difference by Chris Voss. For those that aren't familiar with it, Chris Voss was the top hostage negotiator for the FBI and wrote one of the best books on negotiation that I've ever read. And if you're an audiobook fan, he reads it himself. An East Coast guy and his anecdotes are spellbinding. So I really appreciate that. But the ability to really understand the world from the perspective of the person that you're talking to is critical, I think, in what I've been able to accomplish. The second one would be mindset. And there's a number of things that we can talk about with this. But I think one of the biggest things that steers people wrong today is this idea that you need motivation in order to do the things that you need to do. And I think that's actually backwards. Action creates results, and it's actually those results that create the inspiration and motivation to go deeper and longer. But a lot of times people sit around waiting to be motivated, and that's just a recipe for disaster. And then the third one I think is relationships, but probably not the relationships in the way that most salespeople would think about it. Oh, I got to make sure I get these clients out to dinner and make sure that I'm on a texting basis with my key stakeholders. And those things are important and they'll come into play later. But I think from a relationship standpoint, the support structure that you build around yourself is so very important. And we can spend a lot of time talking about this as we get into the proper podcast, Scott. But one of the things that you and I talked about earlier was the idea of having a personal C-suite. And so one of the things that I've done is sought out and hired various coaches and mentors in the different areas of my life. From a sales perspective, my Chief Revenue Officer, to mindset management, which is where Amber comes into play. If we call that Chief Talent Officer, making sure that we protect the asset, which is yourself, but also a Chief Financial Officer. And the work that I do with Rob, making sure that the strategies that we're deploying are getting us to the goals that Jess and I have long-term for our family. Building out that team is a really critical part of it in order to achieve at a high level, not just once, but multiple times year in, year out.

3:39 Scott Ingram: Love it. Love it. Can't wait to dig into that. I love the concept of that personal C-suite and just surrounding yourself with, hey, here are the people that are going to help me perform well and get to that next level and achieve what I'm wanting to achieve. I think we also had one disclaimer. You said that given your background, maybe you can articulate this better than me, but this may not be kid-friendly all the way through.

4:00 Rich Strobel: Might not be. If you're listening to this in the car on the way to work and the kids are in the back, you might need to do some earmuffs from time to time. What I share with Scott is that I cut my teeth in business-to-business sales working with trucking companies selling supplemental insurance. So I've sat in 18-wheeler passenger seats doing demos. For more time than I'd care to admit. And I have heard pretty much everything. And then to boot, I married a former preschool teacher, which I think behind truck drivers probably have one of the worst mouths.

4:31 Scott Ingram: That must be a trade secret.

4:33 Rich Strobel: I'm not feeling so much restraint during the day that when they get home, man, everything comes out.

4:41 Scott Ingram: Oh, that's so funny. I can't hold the filter any longer. There's just none after the children.

4:46 Rich Strobel: It's called restraint collapse. This is one of the things that I've learned. They hold it together all day. And then they get home where it's safe and it's comfortable and man, everything comes out.

4:54 Scott Ingram: Oh my gosh, that's so funny. When you told me that the first time, I took it the wrong way. I took it as, oh my gosh, you're just totally offensive to your wife. But maybe it's the other way around.

5:05 Rich Strobel: When people find out that I'm not the foulest mouth in my house and to boot, of the 4 of us, I'm the quietest in my family. People have a really hard time conceptualizing what that's like until they spend some time with us.

5:19 Scott Ingram: Oh, that sounds entertaining. That sounds entertaining. But let's move on with our own entertainment and just contextualize this a little bit. Talk about your role and how you got to number 1 there.

5:29 Rich Strobel: Yeah. So I joined Smart Data Solutions about 3 years ago and had pivoted into healthcare technology sales about 6-ish years ago. And when I came to Smart Data, we're in kind of the typical private equity-backed scale-up business. And this is an area that I've landed over the last couple positions. My days of being interested in startups are past. I've got a family now and a mortgage, so I need a little bit more stability. And the exits are never as juicy as you want to believe early on, but at the same time, not really built for big corporate. Spent the first 20 years of my career as a 1099 independent contractor, commission-only sales roles, both in production but also in sales management and leadership. And really don't think I'm built well for a large corporate structure with a lot of red tape and real formal hierarchies. I'm good at selling into them. Apparently, but yeah, don't want to, don't want to live there. Came to Smart Data, sat down. It's wild. I sat down with the co-founder, co-CEO, and the first interview, I didn't expect him to be in the first one, but he asked me, he said, Rich, which position are you here interviewing for? I'm like, say more. Recruiter sent me down for a sales role. He's like, yeah, we've got our new logo guys. We're going to add somebody there, but we're going to hire our first account manager. And I was like, wait a second, you guys have been around for 20 years. How many clients do you have? It's like 400, 450. I'm like, okay, does everybody have everything? No, no. Everybody's got their own combination of different products and different things. I said, well, are they happy? He said, oh yeah, nobody leaves. Attrition's really low. I'm like, when you have a client that wants to add services, what do they do? Oh, they just call the IT help desk and then the engineers capture some requirements and toss it over to Dylan. He writes the SOW and away we go. I said, Pat, I can help. You need somebody that's really strategically looking at it because we sell into really large health plans and navigating the world in a large enterprise environment versus your more mid-market. There's a lot of similar motions, but man, there's a vast world of difference between what those motions look like. I was the first really strategically oriented person to come in. We call them client partners, but where I've landed, a lot of trial and error as we try to build, figure out how to orient the team. But where I've landed is really a key account director, strategic sales. I work with some of the largest and most complex clients that we have. And the bulk of my time is spent cross-sell, upsell, but we all, the client partners, still have responsibility with new logo. So I tend to get tapped on new logo opportunities that are larger and more complex in nature.

8:06 Scott Ingram: Nice. And then quantify your results for us. You're here for a reason.

8:09 Rich Strobel: Yeah. So last year closed $5.3 million against a $4 million quota, which put me in the top spot.

8:16 Scott Ingram: Very nice. Very nice. Let's talk origin story. You hinted at talking to truck drivers. How'd you get into sales in the first place?

8:23 Rich Strobel: How far back do we want to go? Do you want to go to the very first sales role?

8:27 Scott Ingram: Let's talk through the evolution, man. There's a reason I book all this time to have these conversations, right?

8:33 Rich Strobel: It's a winding path, right? Because when I was in high school, actually, this is the '90s, to date myself, and everybody had the car stereo systems. So I was putting in all these subwoofers and speakers in all my buddies' cars, and I'm like, man, I should get a job doing this. So I went down to the old Best Buy And talked to them about getting a job doing install. And the response was, everybody has to start on the sales floor for at least 6 months. You need to learn the products, you need to do all that. So if you can do that, then we can talk about moving you into installation. So I did that, went out, worked in car audio at Best Buy, and was apparently really good at selling warranties. So that's the metric that we were measured on. I was 17 years old, so didn't really grasp a lot of it. But got to the point where I was ready to make that transition, got everything approved by the store manager, the regional manager of installation, the install manager, my department manager. And then in the 11th hour, the sales manager for the store said, nope, you're not taking Rich. No, he sells more warranties than anybody on the floor. I need him there. And this is as a high school student working part-time. And I got frustrated with it because they weren't paying commission or anything. I'm like, so are we going to talk about pay or anything? Because I can make more money doing install than working in here. And he's, no, you're good where you're at. I'm like, okay. So I walked across the street to the… what was called Audio King, later became Ultimate Electronics, but they paid commission. So I walked over there and said, here's my deal, are you guys looking for somebody? And they're like, yeah, for sure. And did really well there and made more money than I thought I could as an 18-year-old, 17, 18-year-old. Then went to college, started my engineering degree, and My first year, I had done a bunch of post-secondary work, so I had more credits than time, right, in college. So I looked like a sophomore on paper, ended up getting this engineering internship for my first summer. I got college credit, got paid. It was an ideal situation. The new graduates were sitting in cubicles out on the floor on the farm, right? But they put, for some reason, they thought it'd be a good idea to put 3 interns in an office with a door. So they had this big office that they put 3 desks in. So they put the 3 of us in there. And then to boot, each of us had a workbench out on the shop floor that we could go build and tinker and experiment. Couldn't have asked for a better scenario. And I was miserable, Scott. Miserable. In that same summer, I had committed to do an orientation for incoming freshmen. So I was like, really appreciate this internship. Do you need me to let you know that I've committed for 2 weeks out of the summer to go back up to campus? And they're like, yeah, that's fine. So went up to campus, exact opposite kind of format, living in the dorms for a week. Fargo gets to be in the 90s during the summer and there's no AC, so we're just sweating. We had to be in the dining center at 7:00 AM every day because all these incoming freshmen look forward to nothing more than getting up at 7:00 AM and going to breakfast before they start their day. But in the odd chance that somebody came down, we had to be there. And then we'd run tours all day. We'd have a little bit of time for lunch when we switched groups, and then the new group would come in and we'd start them in the afternoon and we'd throw a party in the union until late to keep them from going to off-campus parties, and then want to debrief. So it'd be like 2 in the morning before we'd get to bed. And I had the time of my life making $400 a week, which came out to $2 an hour for the amount of hours that we were putting in. And I was like, man, this is crazy. That was what I loved. I was just walking around, talking to people, sharing experiences, finding out what they were nervous about and helping them put those fears aside. And I had an incredible supervisor at this internship. And he sat me down during what I now know as a one-on-one. Didn't understand what it was at the time. We just met every now and then. But he looked at me, he goes, Rich, I can tell you're not happy. Just because you're good at something doesn't mean you need to do it. And I'm so thankful that not just that he shared that, but that I was actually in a place where I could hear that and not be offended by it, but actually see the wisdom in what he was trying to share with me. And so that next summer, one of my good friends from a sorority recruited me to go sell books door-to-door with a company called Southwestern. And that's really where professional selling clicked for me. Brutal, brutal gig. I did it for 7 summers, worked there full-time after I graduated as an organizational leader and manager. And it's 100% commission. They take students and you do like an exchange. So the students from up in Minnesota and North Dakota, we'd go down south. Southern students would come north and we'd work minimum 80 hours a week away from home, full commission, no guarantees. Oh, and you gotta find a place to stay when you get there by knocking on doors too. So like just bananas. And I loved it. I hated it and I loved it. It was really hard, but figured out a lot of things. So from there went into insurance. When I finally realized I had enough of that, I moved to what was a spinoff company that sold insurance, a lot of the same format. But that's where they were largely residential selling, knocking on doors to sell insurance. We wanted to take a different approach. We're burnt out. So we're looking at it going, man, if Aflac sells us to businesses, why can't we? And so we, myself and the 2 guys that I started with who I'd worked with at the previous company, we were the first 3 reps in Minnesota trying to figure out how do we do this door-to-door, or not door-to-door, business-to-business, which Funny enough, still door-to-door, man. Still going and knocking on every business on Main Street. And by the time I left there, gosh, 13 years later, I think we had grown to about 120 agents in 9 different states doing somewhere north of $25 million recurring revenue. Really built that up. And then my position got eliminated, so had to figure something else out. That's when I realized tech was something I was interested in.

14:17 Scott Ingram: Yeah, given that whole story, if you were starting over today, right, like now it's the '90s, you're in college, where do you start? What's the path that you take? What do you do differently?

14:29 Rich Strobel: That's a really difficult question that I don't love because it's easy to look in hindsight and say, oh man, if I just would have done this, or if I just would have done that, all these things would have been different, right? At the same time, I think I would not be who I am today and understand the things that I understand the way that I do if it weren't for that path. I think if I could change anything, I would maybe have not spent quite so long in some of those roles because I tend to be loyal to a fault to companies, and that can not always serve me the best. A lot of those things that I learned… I remember having a conversation with a good friend of mine who runs a business down in Texas, there in Dallas, and I said, Michael, I don't think I'd be good as an employee. I've been independent for all these years, a couple of decades. And he looked at me, he goes, nah, man, you'd actually probably be really really good because of that. You understand business ownership at a level that most people that have just been W-2 can't comprehend. And that really struck me as, okay, and I think that it's easy to look back and wish things were easier or different or better. I catch myself like, man, if I had spent 20 years in healthcare technology, oh man, that would have been really great. But at the same time, I don't know that's really going to make the difference. I think it's important to look for the lessons that we have in the struggles and in the hardships and in the things that don't necessarily go as planned. All those things are building you up towards something. The question is whether or not you're going to capitalize on it.

15:54 Scott Ingram: Yeah, I definitely believe that things happen for a reason, and that answer is probably the most common answer. I had to go through all of those weird twists and turns and do all of those things because I couldn't have been successful where I am now without that background. And you articulated it pretty well, right? This idea of whatever that is, whatever the weirdness is that you're in right now and that you'll continue to go through over the course of your career. It's just, it's looking for the lessons. What am I supposed to learn from this particular bit of strangeness? And you just take it forward.

16:30 Rich Strobel: One of my favorite podcasts to listen to is The Game by Alex Hormozi. Talks a lot about business. Alex has this really interesting perspective. What he tries to do with himself is look through the lens of 20, 30, 40 years from now, I'm sitting in the situation that I've created everything that I ever wanted. And I'm looking back 20 years at this man that's trying to get to where I am. What are the things that I would need to put him through in order for him to develop the skills and the mindsets to get here and actually be this successful? What would I have to put him through? And that's the frame that he looks at when he goes through hardship. I think there's so much value in that. Doesn't make it easy by any means at all. It's hard. It's really hard.

17:15 Scott Ingram: It's not the thing you would voluntarily sign up for.

17:18 Rich Strobel: But man, one of my mantras that I always remind my coworkers with is, man, if it was easy, it wouldn't pay well. So let's just figure it out.

17:26 Scott Ingram: True that. Rich, you've sold a lot of stuff. You've done a lot of different things. What's your favorite sales story from any role, won or lost? But maybe it was the deepest lesson. Maybe it's the most entertaining thing. Like, I'm up for anything.

17:39 Rich Strobel: Do we… how much time you got, Scott? We could talk about this for…

17:43 Scott Ingram: I'll take 2 if you want.

17:45 Rich Strobel: One of the most painful I'll share is from this year. We're in RFP for one of our emerging products, and we were added late with a prospect, a very strategic prospect that we had chased. It was assigned to a different rep a couple years ago. They took a run at it, didn't get anywhere. Conversations started coming back around, and I engaged with them. With the help of my SVP at the time who knew the CRO there. So it wasn't his decision to make by any means. This is a tech purchase, but he at least let us know that there was an RFP happening. So we went into it and against all odds kind of thing became like pole position front runner in the RFP, flew out to Manhattan to do this big onsite with as one of 3 finalists and everything was clicking along really well. And we're looking at probably a $2 to $2.5 million ARR deal. With upsell possibilities. Really excited. This would be a really big win for an emerging product. This would be a big chunk of quota retired really early in the year. And they had us come back to do a demo. And I did not put the level of pressure on my team that I should have to be excellent. And some of the key things that they were looking for, the demo didn't address. In the prep work leading up to it, I think bottom line is as an organization, we got a little too comfortable. To the extent that we were actually removed from the running in the RFP. Like the prospect team was so frustrated at the lack of these key functionalities that they just removed us completely from the RFP. And that was a very difficult thing to swallow. A product owner ended up not having a career here anymore as a part of this. But looking at my ownership in that, I should have done a lot better diligence through that process. And the minute that you start to think that you've got it, It should be a warning signal. That's a good signal to dig deeper, right? So that's one of the most painful, but it's a lesson that I carry with me constantly to not get comfortable. Don't be complacent. Still look at what can we do better and make sure that we're just trust but verify. What's really important when you're working across functions, which in sales, especially at the enterprise level, we have to be really good at not just the client, but also internally working across different cross-functional groups. And I think Trusting but verifying is one of the most critical guidelines that I can think of. Fun one I can share with you. When I came to Smart Data, I think our average deal size is about $42,000 ARR. So not large. A lot of run rate transactional selling occurring, not a lot of strategic transformational deals. In about 6 months into my career, we got a new CEO, which obviously was something that had been in the works for a long time that predated even my hire. But in the course of doing kind of the new CEO roadshow, Sashi and I and one of our other executives had flown out to Philadelphia to meet with one of my larger, not the biggest, they're probably top 25, top 30 client at the time, but meet with a big health plan out east. And I was able to get a lunch put together that had the VPs that work our day-to-day, but their SVP was this enigma. We knew of Tony, but You can never get Anthony in the room. And a new CEO was what it took. So we got him to come out to lunch. I was sick as a dog. I had the flu or something, landed the night before, and just every over-the-counter thing I could think of, I'm just throwing it back, trying to muster this, muster through this. So we go to lunch and we're talking and it's very amicable and everything. They're great. They use just our digital mailroom solution. And as we're getting to the end of lunch, dessert had come out. And our CEO, kind of almost a Columbo moment, not knowing it, but he's, oh, and one other thing capability-wise is we're a full-fledged clearinghouse. And the forks got stopped midair. And this SVP looks over and he goes, what do you mean? Like, actually? Or just… he's, no, we're a legitimate clearinghouse vendor. And he said, we're in an RFP right now. I'm meeting with Change Healthcare, who at the time was the biggest in the industry. I'm meeting with them this afternoon. What do you mean when you say you're a full-fledged clearinghouse? And so my COO is under the table texting the team back home, getting numbers. So in that world, it's about trading partner connections and how well can you actually do the business. So long story longer, they added us to this RFP informally, didn't have to go through the 300 questions that everybody else did because we were an existing vendor and kind of a strategic partner at the time. And we were able to beat the number 1 and number 2 contenders in the industry and do… I think that ended up being like $2.1 million ARR, about $10 million TCV, and we won it. But what we had to become as a company in order to actually win that deal was transformational for us internally. It was the largest deal we'd ever done at the time. And what's so exciting is to see last year I was able to close $3.3 million deal. So a big chunk of that $5.3 came from one very strategic deal that was right down to the wire. You and I were emailing back and forth at the end of the year last year. Is this thing going to actually happen? Is it going to get recognized the way that it should? Because it was just a magnitude bigger than anything we'd done in the past. But now I look at where we are now and I got my work cut out for me to keep the spot because one of my colleagues has closed a $5 million deal this year who we've become as a company. We had to completely reorient ourselves. And my CEO loves to tell all the story that after we got back, we walked out of this restaurant and we're all like on our phones, like calculating numbers, like, this could be big, this could be massive, this could be great. And then we get home and I start talking to my colleagues because again, I'm only about 7, 8 months into my career at this point. I'm still learning a lot about the company and the world of clearinghouses in, in our industry. It's this really funky Co-opetition. Like, all of the different vendors, in order for anything to work, have to work together, but we're all competing for the same contracts. So whoever wins it is going to have to work with the people that didn't to get… what a clearinghouse is, it takes the claim. When you go to a doctor, that claim has to get from the doctor to the insurer to get paid. We're the pipes that get those claims back and forth. In order for that to work, we all have to work together, but we're in absolutely fierce competition with one another for these payer contracts. So who we had to become as a company just shifted dramatically. We had to have executive engagement in the sales process that was reserved for QBRs and that kind of thing. It wasn't really part of the pursuit. That had to change how we carried ourselves, how we prepared for meetings, how we prepared for demos, all of that. I can remember, and it was painful, man. I distinctly remember being on a call leading into the demo, we met at 8 or 9 AM on a Sunday with the whole team and realized that we weren't close. So everybody took time to work on it and we came back together at 9 PM and we were on this call with our new CEO until about 1 in the morning on a Sunday because it wasn't good enough. And he was bold enough to hold us to a higher standard and see what we were capable of versus just what we had done. And that's what I've really carried from that deal is the ability to see what we're capable of versus just what we've done so far. And I think that's a theme that I can trace that back all the way to growing up. I grew up on the east side of St. Paul, extremely blue-collar area. I'm one of the few in my family on both sides that have gotten a high school diploma versus a GED. And I was the first one on both sides of my family to actually go to 4-year school and graduate, let alone graduate, just even go to college. But what I really appreciate about the way I was brought up is that I was always shown that there's things that are possible and this is not the ultimate achievement of what's possible. We've worked hard to do better than we grew up. We want you to do better than the way you're growing up. It's all out there for you, but you got to figure it out, kid, because we can't afford to pay for tuition. So, better get some scholarships.

25:57 Scott Ingram: Yeah, for sure. I think the common theme with both of those stories is just all of the internal collaboration that happens. Let me ask you this, right? As you think about the whole of your job, what percentage of time is with customers and externally focused, and what percentage of time is internal and working with and across your team?

26:21 Rich Strobel: Man, I would say it's probably 60/40 internal versus external, if not more. And that's where I think… I can't remember who, what podcast I was listening to, or it might have just been on LinkedIn, but the conversation was around relationships and how important are these relationships to actually getting a deal done. Once upon a time, it was about who do we take out to golf and who do we take to dinner and all these things, and that's how we really get a deal done. So we got to have that relationship. And I don't think that's as necessary as important. I think those things are important. And for me, what I've seen is it's less about the first deal and more about when things go wrong. Do you have the relationships that are going to buy you the grace to fix it, or are you going to get fired as a vendor? But what I think is critical is the relationships that you build inside your 4 walls of the organization. And this is where tactical empathy comes into play as well, is understanding what is the life of the person that I'm talking to as they see it, not as I see it, as they see it. And empathy is different than sympathy. Understanding what's hard for somebody doesn't mean that I feel bad for them. I might. Doesn't mean that I agree with them as to what's hard. Empathy means I understand that it is hard for them and why. And when you have that understanding, now problem solving takes on a completely different life. One of the things that I learned a number of years ago is that whatever makes things easier for one team almost always makes it harder for another team. So when you really pause and are intentional about the recommendations you make or the ask that you make and you understand that, it allows you to address it versus Just having it come up as an objection or a reason not to move forward. It's, hey, I know this is hard because of this, and I know if we do this, it's going to make this thing over here probably harder for these people. But here's why we would do that. Here's why that would make sense, even though it will make it harder for them. Here's why it makes sense to do it anyways. But having that level of understanding makes a world of difference with deal velocity.

28:29 Scott Ingram: Yeah, I feel like this is such an under-addressed topic, whereas as you scale up into more and more more complex deals, as you get into true enterprise sales, that ratio skews more and more to you're doing more work internally than you are with your customers. And we just don't talk about it. We don't talk about making those relationships work, the skill sets you need to have. I think ironically, a lot of the primary coordination I do is with our internal program project managers, but I feel like the skill set that's important for me is also, it's a lot of project management type of skill set, right? It's really thinking about what are the different things that need to get done, who needs to do them, what are the critical path types of items where if this thing does, if this set of things doesn't get done, these other things can't happen. So just thinking through kind of the order of operations and all of those things. There's an article I came across, actually, I think I probably read this when it was new. I have a link for this because I reference it a lot. If you go to top1.fm/hbr for Harvard Business Review, clearly this is one of my favorite HBR articles of all time. This is from 2006. It's an article on better sales networks. And exactly to your point, when we think of sales network, our default assumption is prospect network. Who do I know that I can sell to that will buy from me? Yes, that is a part of your network. That is an important part of your network. But another huge, just completely overlooked piece is the relationships and the network that you have inside your organization. And Rich, you said you don't like working for big companies. I totally understand that. But I think as your organization is larger, like the larger that organization is, more complexity you have there, the more relationships you need to have to just figure out who in the heck can help me get this thing done. Because I actually believe that part of our job as great sales professionals is wielding our organizations on behalf of our clients. And it's knowing how to get things done for them, especially in a role that you're at, which I think is just wildly undervalued, is like a true account management professional. The biggest deals don't come on the first sale. They come the second or third or fourth transaction because we've built trust. And now the big opportunity is there. And the only way that is going to happen is that we maintain trust and we continue to be able to connect all of these dots for them because it's much bigger. It's much harder. It's not, here's the thing out of the catalog, pick it out, pay me money. There's just a lot more moving pieces.

31:20 Rich Strobel: Well, and I think it's been exacerbated by just the macroeconomic forces at play right now. Look at what it takes to get a deal approved at a client. These days, those thresholds have just continued to come down and down where CFOs are having…

31:32 Scott Ingram: where's the AI that's fixing that, man? Holy crud, is it hard right now to get a deal across the line?

31:37 Rich Strobel: It's brutal.

31:38 Scott Ingram: Hang on, we have to have it go through a 6th security audit because some guy in a corner with a red stapler has questions.

31:45 Rich Strobel: Yeah, and I always used to have the fun banter with my last company. It was strictly existing client sales, and that new logo was a different team. We'd have this back and forth. Well, dude, I got to get an MSA, right? That's going to take forever. I'm like, yeah, Tried talking around delivery issues in order to get a cross-sell across the line because we're not delivering on what we already got. That's a challenge in itself. And that's where those internal relationships become even more important in cross-sell and upsell motions, because you've got to ensure that they're at a point that they're satisfied enough that they'll be open to even having the conversation, let alone making a purchase. Having those relationships and understanding… I think one of the biggest things that I've learned from Jamal Reimer's Masterclass, which as far as a CRO, Chief Revenue Officer, I would put Jamal in that category. But this idea of tying your initiatives to, or tying your sales suggestions and recommendations to existing enterprise initiatives that allows them to get funded. Now you're supporting objectives that have already been prioritized versus potentially distracting from them. That works internally too. You've got to couch your ask in terms of What has this team been tasked with by leadership to go and accomplish? And how can getting this thing done for me move us closer to that? Especially when different companies go through different phases of growth, it might be we just need top line and then that'll shift and it's, oh, we got the top line. Now we need to work on EBITDA. We got to do more profitable deals. And those things start to shift and move as you grow a company. And I think it's really important to just have that understanding of what is it that's important to this person that I'm talking to and how can I help them get that? And in the course of that, get what I need to help these other people get what they need.

33:29 Scott Ingram: Yep. And to me, this is my favorite part, is when you get to that strategic level and you have an understanding of the big picture and those big initiatives. I was working with one of my clients, they're a fascinating company. I won't get into it, but they send a lot of of text messages, probably hundreds of millions. I haven't worked with them to quantify this quite yet. It's a huge part of just the way they execute in their business. Understanding some of the things that they're working through and having gone through and let them articulate, here's the challenges, this is what we're trying to solve for. We've got 40% of it solved for in this path. We've got 60% of it solved for in this path. Unfortunately, those 2 paths don't really go together. And then also understanding some of the strategic things that we are doing on our side, right? Things that my CEO is working on and going, wait a minute, we are doing some deeper development on a product that can potentially support this. So can we put this together? Can we connect the dots between your specific needs and the specific challenges of client company? With the strategic bigger picture initiatives that we are trying to build and more of a SaaS product motion inside of a services company and just being able to connect the dots there. Like really, it's fun. And I think it's work that has to be done at every level of the organization. When you think about what are the things your client is going to need, maybe there's something we need from accounting and finance, maybe there's something we're going to need on the product and delivery side. Maybe there's something we're going to need on the security privacy side. And to your point, and speaking of Jamal, like maybe this is something that needs to be elevated and escalated to the executive level. Have I made executive connections to give me the overhead I need to operate? I know that Jamal, I was just catching up with Jamal last week. He's got a new SaaS solution. I haven't looked at it directly, but it's called Wiser. And he's basically built an answer to get you straight to those points of views that are going to connect the dots between, hey, here are my clients' top initiatives. How do we align our offerings and directly connect to that idea? And it's doing a lot of legwork. So on the surface, sounds amazing. Haven't looked at it, but maybe something worth looking into. And if Jamal's behind it, it's going to be pretty solid.

36:05 Rich Strobel: Guy's got a pretty good track record, man. But that's the thing, when you can capture both sides of that, the enterprise initiatives at a client or a prospect with your own internal enterprise initiatives, and those line up, man, you got lightning in a bottle there. And now things can move in a really material way. But getting there is a lot of work. If you're excited about doing that kind of work, then yeah, enterprise strategic selling, that could fit if that kind of worked.

36:29 Scott Ingram: Yeah. And it is sales, right? A huge part of this, all of that internal work, you've got to get them behind. You've got to get them bought in and sold into, hey, I'm going to need you to work until 1 AM on a Sunday to support this initiative. Like, that's not an easy thing to close.

36:46 Rich Strobel: No, it's not.

36:47 Scott Ingram: It helps if you have your CEO behind you.

36:49 Rich Strobel: It does, yes. Especially a new CEO that everybody's wanting to make sure they make a make a good impression.

36:54 Scott Ingram: Absolutely, absolutely. Rich, what are you most proud of?

36:57 Rich Strobel: Man, this is an easy answer for me. The thing that I am most proud of is the relationships that I've been able to cultivate and keep close to me. First and foremost, my wife and my 2 boys. May sound cheesy, but dude, that's why I do it. That's why I get out of bed in the morning, is to keep them close and achieve the things that are important to us. And they're incredible. The second one though, in an area that I think doesn't get as much attention as it needs to, especially in is personal friends that are like really deep and meaningful conversations had versus just sitting next to each other watching a sporting event and drinking beer. Like, that's fine, that's fun, but actual meaningful relationships and having a ton of them is not important. Having some really quality ones makes all the difference in the world. We were in Denver last week and it was a personal trip, not a business trip for once. But flew down to see a concert that was going to be… it was a band called the Bluestones. So I love drum and guitar. They were coming to Minneapolis this week. They're going to be in Minneapolis, but a bunch of us decided, no, let's fly out and get away from all the distractions. And of course, we're all at points in our careers now where we still end up working way more than we should on a personal trip. But we flew down solely for the fact to spend time with each other. And this band being in town was an excuse. One of the guys has a home there that a bunch of us could stay at, and it really hinged around our buddy Kellen, who lives in Australia. He had business there, so for him it was a work trip that he was able to extend, but that allowed us to get Kellen folded into the mix because between family and everything else, trying to get his time is not easy as a CRO. The reason I bring that up is the conversations that were had in the small moments Drinking coffee in the morning, out to lunch, on a hike at Red Rocks, whatever it might be. The dinners were epic, that's for sure. But the conversations got deep, and it's a group of guys that really genuinely loves and cares for each other. Not afraid to call each other out if somebody's starting to talk some absolute nonsense or avoiding what the real issue is in something, but actually having conversations. About parenting, about marriage, about work life. And I don't think enough people have that caliber of relationship, especially over time as we get older. There's a group of guys that we used to travel internationally together. We would just go on these 3-week epic adventures to… one of them was there was 11 guys, 2 RVs, and we did 1,800 miles of the east coast of Australia from from Sydney all the way up to Cairns, surfing, diving, and sailing. 9 of us went to Africa and did all of it, man. We've rafted the Nile River, we trekked mountain gorillas in Uganda, did the Serengeti and the Ngorongoro Crater, hunted with Hadzabe tribesmen, had a beach villa in Zanzibar. Like, just crazy trips. And that was why at that time in our lives we worked so hard, was to be able to do these like epic adventures. Now we all had kids. And so, man, that's not the most important thing anymore. I can't get away for 3 weeks and just disappear into the wilderness. But to still find reasons to get that group back together and continue those deep relationships is so very important. And mental health started to finally get some airtime as we were coming out of the pandemic. I can remember specific sections from your summit that first year of the pandemic that really focused on mental health and the work that Ian Koniak does talking about addiction. These are things that are super important. And I think for a long time it got swept aside. It was too woo, all that kind of stuff. But I almost sense that there's now a reaction to how much time we gave that and it's fading a little bit. And I think it needs to remain at the forefront. Self-care is not selfish. My wife is constantly on me reminding me about that because I'm one to take care of everybody else and let myself go to pieces in the process. And that does nothing for anybody. Amber talks about you've got to protect the asset. And in this role, you are the asset. You've got to protect that. And you've got to do the things that you need to make sure that you're bringing your fullest self to every single day. It's not easy. But it's so important.

41:20 Scott Ingram: Yeah, I love that you're calling this out. I knew that, first of all, this topic and the idea of the personal C-suite and just surrounding yourself with the… in oftentimes like paid professionals who are going to support you in what you're doing, but also just having friends and having people who understand you. And until I started doing the summit and this podcast and finding some of these people, I this role, it's really hard to find people who understand what we're going through and the value of finding your people who, A, have that understanding and a better level of context. The challenges you're talking through don't seem completely crazy, but who also see you. And to your point, like where there's enough relationship where will you call me out on my bullshit? And, you know, like, yes, Scott, you're talking a lot, but this is garbage.

42:17 Rich Strobel: It's so easy to offend these days.

42:20 Scott Ingram: Yeah. Oh my God.

42:21 Rich Strobel: I think a lot of it's needed, frankly, because we went through decades of having zero consideration for anybody else in how we talk and act and think. But the negative consequences of that is that people don't say what needs to be said. And sometimes, man, there's consequences to saying what needs to be said that I wish weren't there. There's times where I've called somebody out and their reaction was really strong, which is indicative in itself, but that relationship suffered from it. But I care more about the person than I do… this gets talked about a lot… I'd rather be respected than liked. And I'm a people pleaser, so that's very difficult for me. But at the end of the day, I am much more interested in what is right than who is right. And that applies to how I conduct myself internally in my company as well and with my clients. If I've got a client that's abusive to my team, I'm getting on the phone and having a very direct conversation with them. And if that means we don't get to work together anymore, so be it. But I'm not going to stand for that kind of treatment of my team because they're professionals. And in my teams, if we're not, we're One of our core values is to be world-class. That means that certain activities aren't going to cut it, man. You've got to be focused on the outcome, not just the effort. Our CEO is famous for saying, I don't want to hear about hard work. I don't really care. It's about outcomes. That means you have to work really hard or you can just do it. Cool. But outcome is what is important. It's a filter that things have to run through, but it's really critical.

44:00 Scott Ingram: Yeah, absolutely. Absolutely. And it's interesting. There's a recent episode conversation I had where it led us to unpacking this idea that people do business with those that they know and trust. And I went, wait, you know what? Isn't even part of that. It's really trust. And somebody is going to trust you more if you say the uncomfortable thing that they might not like is the truth.

44:20 Rich Strobel: And that's what it comes down to. This idea of being liked by your clients. What I've found is that's the natural byproduct. Of conducting yourself well. I had a conversation with one of my close buddies that was on this trip actually, but this was a couple years ago. And what we were talking about was it almost feels like what really limits people in how far they can ascend, either in organization or just as a professional, is it becomes a degree of emotional maturity. How well can you handle wanting to come unglued at somebody But still keeping your composure, right? And saying what needs to be said in a way that they can actually hear it. Because if you're just always banging your fist on the table and coming over the top in every meeting, people, they start to not hear it or the reaction, the defensiveness happens really quick. And then they're just trying to defend their position instead of actually hearing the message you're trying to convey so that you can figure out a solution forward. It's really critical, and I've recognized that in myself, and there's growth that I've had to do over the last couple years. Well, man, I am getting way more upset than I need to be for this to be effective. So it doesn't mean that I can't be frustrated. It doesn't mean that feeling isn't valid. It's valid. And we have this conversation with our kids every day. Doesn't matter. You're responsible for your choices. My wife reminded me of this last night because I yelled at my son. I didn't want to. And she's, listen, we tell them, you're the damn adult, control your actions. It's so important to just understand that we have these emotions, we have these feelings. That just means congratulations, you're human. That's part of it. You've got to learn what to do with those. Hormozi on his podcast recently was saying, he did a whole talk about how one of the greatest skills is the ability to have an incredible attitude when there's nothing to have an incredible attitude about. It's hard.

46:17 Scott Ingram: Yeah.

46:17 Rich Strobel: Yeah.

46:18 Scott Ingram: I think kids are the ultimate test. Okay. I'm sleep deprived. I'm super frustrated. You are driving me crazy. And the mature adult thing to do would be not to scream my head off, but man, right now it's a… I failed that test many times with my kids when they were younger. The good news is it gets easier. It gets different.

46:38 Rich Strobel: It gets different. Oh, how you frame that's important.

46:43 Scott Ingram: Yeah, for sure. The relationship piece is certainly a strong point, something you're proud of and that works well for you. What do you struggle with? What's the biggest challenge?

46:52 Rich Strobel: For me, I think at this stage of my life, my boys are 7 and 10. My 10-year-old has autism and ADHD, so there's a lot going on with that. For me, it's getting overwhelmed. And that's the reason that I hired Amber. And I've worked with her. We did her kind of her normal offering, which is like a 6-month engagement, took a couple of months off, came back, said, Amber, I need more. Let's do it again. My wife is the biggest Amber Deibert fan of any because of the change that she sees in how I operate, not just at work but at home. And that's just… you need to hire Amber again. Call Amber. We need Amber back in the mix. And so we're, we're working together again. I actually get to talk to her tomorrow, I think. But I struggle with that, man, knowing what to prioritize, because especially an enterprise selling role in the strategic side of things, the to-do list will always exceed the amount of capacity and bandwidth that you have. You need to come to grips with that. And then as you start to earn more and more money, you want to hang on to more and more money. So you got to start doing things like investing and knowing where your money's going. And we own an investment property, so that takes work. And then, like I said, my son requires my time and attention, not just physically being in a room, but like being very intentional with how I'm engaging with him and helping him reframe things and understand his perception may not be reality. It doesn't mean it's not important, but again, how do we Acknowledge that, but then move on to be constructive. Marriage takes work, man. If you want to have a really amazing marriage, you better be ready to work at it. It's a relationship. I'm fortunate that my mom is still alive. I want to be a good son and I want to really enjoy that relationship. I've got a little brother who's like my best buddy in the world. Wasn't always that way. We fought like cats and dogs growing up. How can I show up for him and my nieces? I struggle with that, And it's really easy to get super overwhelmed with all those things and knowing what do I need to do right now and how do I really be present with what I'm doing right now when I've got all these other things that need to get done and I don't physically have the time to get to them? How do I balance that and make sure that I'm still incredibly effective?

49:06 Scott Ingram: Yeah.

49:07 Rich Strobel: Yeah.

49:07 Scott Ingram: I think that's a perfect transition to just pick apart and dissect how you structure your day and your routines and everything else. So I'd love… just give us a day in the life. Alarm clock goes off. What time does that happen? And give us a pretty good blow-by-blow till your head hits the pillow again.

49:24 Rich Strobel: This morning is a good example. I've had a great morning so far, so we'll use today. Alarm usually goes off at about 5 or 5:30, depending on what time I got to bed last night. I really try to prioritize getting 7 to 7.5 hours of sleep, which is not always easy. I had my 7-year-old in the bed at multiple points. Last night, but got him back. And that's something that I had this realization this morning, like just the reframe of that. Because when 5:30 came, I wasn't ready to get out of bed by any means because at 4 o'clock my 7-year-old was next to me, the dog was up on the bed too. And that's really easy to get super frustrated with when you're trying to get a good night's sleep. But the reframe that I thought of this morning is, man, how cool, like how amazing That I am this surrounded with love and connection that even my dog needs to be physically next to me, right? Because they just want to be there. That's really incredible. Alarm went off 5:30. I've just come to grips with the fact that it's going to take me about 30 minutes to get out the door. And I've had this trap many times over my life where it's like, all right, if I get up at this time and then I go do this and this, and I've got this massive plan and I've got 3 hours to do it, but it's 6 hours worth of stuff. So I've come to grips with the fact that it's going to take me a half hour to just come online get out the door to go to the gym. So I try to go to the gym or do some form of activity or exercise. I really shoot for every day. I don't always get there, but try to get to the gym, do something to break a sweat and do some work for 30 to 45-ish minutes, get cleaned up, grab some breakfast. Most days I'm back at the house and then shifting gears into helping the kids and the family just get out the door to whatever's going on. It's summer now. So it's a little less stress than during the school year and the timetable is a little bit different. My wife runs a business now, so she's got more flexibility than I do, but at the same time has a lot of demands on her time as well. So trying to strike that balance, but I'm usually logged into my computer somewhere between 8 and 9 depending on the day and what's on tap. And then life as an enterprise seller is different every day, as we all know. I try really hard. One of the things that Amber worked with me on is this incredible exercise that's so freaking simple. It's a tragedy that we don't all do this more, and I know it, and I still don't do it every day. But sit down and just get a list on paper. Forget about all the apps, just on paper. Write down everything you got to do and just get it all out. And the funny thing is, it only takes about 5 or 6 minutes to completely empty everything onto paper. But it's one of those things that feels really big and overwhelming before you do it. Get in the habit of doing that. Just write it all out and then go through and start to prioritize what's an A, what's a B, what's a C. Revenue generating things. If it's going to move a deal forward, that should definitely be a priority. But again, I am responsible for existing clients. So there's a number of things internally that I need to be aware of and might need to act on in front of doing something that's going to generate pipeline or close a deal. So trying to go through and do that, and then even the A's are going to be more than you can ever get done. So what Amber taught me was of those A's, your top priorities, pick 1, 2, and 3, maybe 4, but pick 3. Write those 3 on a little sticky note and then put everything away. It's right there. You can come back to it. Get those 3 done. You can pick more, but focus on getting those top 3 done for the day. And that's gone a long way to helping, a long way to helping with the overwhelm because then you're not mentally carrying that task that you're like, I can't forget about this. I can't forget about this. I can't forget about this. Your mind frees up space because it's, oh no, we got it. It's written down over there. It's on that list. We're good. We can focus on what we're doing now. So run through that. I wrap my day up typically somewhere between 4:30 and 6, depending on the day and what I've got work-wise, but also what I've got family-wise. And then it's dad mode and shifting gears. Oftentimes my wife has been involved with the boys to some degree throughout that time. And so she's ready for some time to not be engaged with the boys by that time of the night. So it's trying to balance getting something put together for dinner, getting some of this energy out of these 2 animals that we raise.

53:40 Scott Ingram: And the dog.

53:41 Rich Strobel: And the dog too. Yeah. And then try to start winding down bedtime, man, it can be anywhere from 8 to 9:30, and it can be 10 minutes or it can be an hour and a half battle. That's kids these age for sure. And then just trying to get everything buttoned up around the house so that I can crash and get up in the morning and do it over again. I try to get podcasts or audiobooks in while I'm doing things like the dishes or watering the flowers or cleaning the pool or whatever it might be, just to have that. There's definitely, with my media consumption, I think of things as there's books that I might be trying to really study and how I consume that is going to look different than just an IV drip of good constructive things as I'm going about other activities. Yeah. So that's how I balance that.

54:26 Scott Ingram: Awesome. On the book side, so you gave us a pretty good walkthrough of kind of information diet. Anything that has really gotten your attention here recently or made a big impact?

54:36 Rich Strobel: Absolutely. I think to plug Jamal again, the book that he wrote, Mega Deal Secrets, I would not have survived that deal, that first big deal that I did here at Smart Data, without reading that book as I was going through it. And what I mean by that is the emotions of doing a mega deal that's 5x, 10x the size of your average deal or more is something that doesn't get enough airtime. And had I not had that to read it and be like, oh man, this is totally normal, this is just part of it. This means I'm doing the right thing. That was so critical. So I recommend his book really highly. One of my other favorites that your listeners probably… all the usuals, obviously, but one thing that your listeners might not have heard of is a book called Mastery. And I believe the author is George Leonard. And it's not a big book. I've read it a few times now. But the idea of mastering something is something that… it's a concept that here in the West, we just just don't appreciate or really understand all that well. George is… the first book I read of his was a book about Aikido. I mean, he's a guy that back in the '70s was an early adopter of the martial art Aikido. And so he started getting exposed to all these Eastern philosophies, and then he wrote Mastery. It's incredible. But I think that's something that we often don't understand, is if you want to be really exceptional at something, that is by nature a long and lonely And when you can embrace that, it's amazing what you can accomplish. But you've got to understand that going in, because that's one thing that I think it's really easy for us to lose track of, is it's really easy to be frustrated and going, yeah, but they don't, and these guys are able to do this, and I got to sit here and do all this stuff. Yeah, you're trying to accomplish something that they can't even conceive. You want to be the best at something? You want to be number one in your company? That means that you can't compare yourself to anybody else because it's a different path, man. So you've got to take a different approach to that. I really like that book. I think it's incredible. It's a quick read. It's entertaining. I really like Dr. Zinsser's The Confident Mind. He's a West Point professor, but also does a lot of consulting. And growing up in the Southwestern kind of environment, it was great because we had this idea of a positive mental attitude. Attitude, like force-fed into us, pounded into us, drilled into us painfully. But it's so great. But I think that there's layers of mentality that go far beyond just positive mental attitude. And that's something else that we can talk about is this warrior progression of mindset. But I really like the way Dr. Zinsser does that because I feel like even though I've been exposed to a lot more than most, it's one of those things that you just got to keep revisiting over and over because by nature, we tend to be pretty negative and skeptical beings. So I think it's so important to continue to study that and explore that and understand because mindset shifts over time. The things that are important to you today, probably very different than they were 10, 15 years ago, and they're going to be really different 10, 15 years from now. So it's not something that you like can check off the box. Like I've done that continually going back to study that. It's really important.

57:44 Scott Ingram: Good stuff, man. Both of those I think are now on my list. So we'll be checking those out. You'll have to check in on me. But the masterpiece in particular, right? I think you're absolutely right, even though I feel like that's the topic of this show, right? This is truly about sales mastery, but it's still like, how intentional are we really being about that compared to a more Eastern philosophy that is, yeah, mastery is going to take decades? We don't really tend to have that kind of patience and understanding.

58:18 Rich Strobel: And there's some other words I want to throw in here that aren't One of the questions that you like to ask, Scott, is what do you believe that other people don't, or what's something other people believe that you…

58:27 Scott Ingram: yeah.

58:27 Rich Strobel: And just to pull that one forward, I think this concept of do what you love and you'll never work a day in your life is complete horseshit. And it sets people up for really challenging situations because the way I would flip that is Find something that you love so much you're willing to work hard at it. When I think about the things that I really love, like sales aside, look at a marriage, man. I love my wife more than anybody else, brother. That takes work. That is something you have to be willing to work at. One of the best things that I ever heard when I was a young man is actually goes back to Southwestern, but Dan Moore was not president at this time. He was still like chief marketing. But he was giving a talk. He actually used to give this talk called Life 101 because he had this thousands of 18, 19, 20-year-olds captive audience that he could impart some real wisdom. One of the things that's really stuck with me is when it comes to finding your spouse or your partner, choose someone that just by the nature of who they are makes you want to be a better version of yourself, like the best version of yourself for that person. And Jess is 110% that for me. Just who she is makes me want to be the best version possible that I can be for her. That takes work, man. Raising kids, if you want to do it well, that's a lot of work. It's a lot of work. And that's without any kind of special diagnoses or anything else. You add that layer in, now you got to really be intentional about how you're operating. How much do you understand about what this child is dealing And are you studying that? If that's really important to you, are you studying it? Are you learning stuff about it so that you can be the best father or the best mother that you can be for them? These things take a lot of work. These relationships with my buddies that I talked about earlier, dude, that's work. We have to work at it because everybody's so busy now. It's… everybody's either a chief this or owner of that or president of that or self-employed. Everybody's busy. And then you add kids in. Man, it really takes intentionality and work to maintain those relationships, but it's so important. And sales is no different. I love it. Doesn't mean I like it every day, man. There's days where I really question my mental sanity. It's like, why do I continue to sign up for this? This is so hard. But man, I love it. There's nothing better to me than when you actually do it really well.

1:00:54 Scott Ingram: That… we're going to pull that quote forward. So what you said is, I love it, That doesn't mean I like it every day.

1:01:00 Rich Strobel: Dude, I don't like my kids.

1:01:01 Scott Ingram: That's so true about every piece of what you just described.

1:01:05 Rich Strobel: Yeah.

1:01:06 Scott Ingram: That's probably true about your wife. That's probably true about your kids. That's probably true about your job.

1:01:12 Rich Strobel: Yeah. I love my dog. If he poops in the middle of the floor, man, I don't like it. The best part of having a dog, man, they're gonna do stuff like that from time to time. Hopefully not that often. So. It's really about understanding what love means. And I think we don't often give it the full understanding that it deserves. It doesn't mean that it's easy. It just means it's worth it.

1:01:35 Scott Ingram: Yep. Yep. Yeah, I think that I'm maybe reaching here a little bit trying to connect a couple of dots, but this idea of not worrying about the thing that you love doing every day, but going back to kind of what you said about Jess and Maybe it's loving what you're becoming too, right? Setting yourself up on a path and getting into a position where, and again, recognizing getting to mastery is going to be difficult. There are things I am absolutely not going to, but I'm loving what I'm becoming here. I love doing this work. I feel like working out like that.

1:02:16 Rich Strobel: 100%, man.

1:02:17 Scott Ingram: Especially in the gym. I don't know, like, I'm very burnt out on lifting weights. I've been doing it my whole damn life, right?

1:02:24 Rich Strobel: Yeah, you started at like 13.

1:02:25 Scott Ingram: And yeah, I love what it does for me, right? So I might not like the work in the moment, but I love the outcome.

1:02:34 Rich Strobel: It's so important.

1:02:34 Scott Ingram: Peloton's a little different. That I have a better relationship with.

1:02:38 Rich Strobel: But I think there's a lot of value in…

1:02:40 Scott Ingram: I enjoy that suffering a little bit more.

1:02:42 Rich Strobel: That's mountain biking for me, man. Like, to me, there's nothing more fun than just ripping through a trail in my 40s on a bike. Like, it's this kind of childhood excitement and wonderment. And the thing I love about mountain biking specifically is it requires incredible intentionality and focus. Like, you cannot afford… there are very real physical circumstances to getting sidetracked mentally. You will crash and you will get hurt. There's a coach, a CrossFit named Ben Bergeron. He's got a really good podcast that I love. It's called Chasing Excellence. And he talks about this kind of progression of mindset because at the bottom, at the lowest level is a victim mindset. And I'm going to try and paraphrase Ben here. I won't do as good a job as he will, but the victim mindset, we all know these people. Everything happens to me. Why is it always me?

1:03:28 Scott Ingram: Blah, blah, blah.

1:03:29 Rich Strobel: We don't need to spend time on that. One step above victim is negative. We're really cynical people that everything everything's always negative, right? And then above that, you've got the positive mental attitude. And when I was younger, I thought that was the top. You got a positive mental attitude, you find a way, you're in a good mood about it. And what Ben puts forward is that there's actually 2 more levels. And above a positive mental attitude is a realistic mindset. And you got to be really careful with this one. These next 2 levels get slippery. Because the realistic mindset, the correlation that he draws is if you look back to prisoners of war, the folks that survived those prison camps were not the ones that were the most positive. The ones that are like, by Christmas we're going home, man. By Christmas we're going to be out of here. It's all right. We're going to be out here by Christmas. Then Christmas will come and go. All right. By Easter, man. By Easter, we're going to be home with our families. And then Easter will come and go. And the lack of realization of those goalposts became so detrimental that they never made it. The ones that made it were the realistic ones. No, this is hard and this sucks, and I don't see a way out of this right now, but we're going to figure it out. That's a more realistic mindset. The challenge is it's really easy for somebody that's very negative to be in the guise of being realistic. And I had guys on my teams in past careers were like, no, man, we're just realistic. I'm like, no, you're fucking negative. Negative, man. Let's call it what it is.

1:04:57 Scott Ingram: I had a great leader. I think the way that he inoculated against that is one of his sayings was, see the truth, but not for worse than it is. When you're looking at a challenging situation, yes, it's challenging. There are some things wrong, but let's not overdo how bad this is. It's probably not that bad. There's a way through.

1:05:16 Rich Strobel: Yeah. And I think that being solution-oriented is the big difference there of, yes, it is hard. What are we going to do about it? Versus, nah, it's just hard. That's where you start to slip into the negativity. And it's a balance, almost like lifting weights, where in order to really unlock hypertrophy and make your muscles grow, you've got to push through that lactic threshold. It's going to hurt. You got to push through that. But especially now that we're men of a certain age, we have to be really careful about getting injured. That happens a lot quicker than it used to. Knowing where that line is of, no, that's injury, that's not growth. We need to be really careful there and back off a bit. The realistic mindset is similar. Above the realistic mindset is what they used to call it the warrior mindset. That's the way I still call it. I think they've shifted it to the competitor mindset to be a little bit more broadly acceptable. But the warrior mindset is that I know that real growth and real achievement only comes through these things that are extremely challenging. I am going to seek out and look for those challenges so I can dive into it and be intentional about engaging that, because I know that what comes out the other side is what I'm really after. And these are not things where you… again, the rent is due daily, if not by the minute, in these mindsets. It's frequent that I catch myself slipping backwards and having to really be intentional about having the correct mindset for what's at hand. But that's something that I really think about a lot is Is this hard? Yes. Is it the right kind of hard? Is this the kind of problem that I actually want to solve? That's what's valuable in the marketplace. This whole do what you love thing. If what you love doesn't pay any money, I think Brandon Fluharty talks about the Japanese concept of ikigai, right? That perfect kind of Venn diagram of what do you love doing? You're good at it. It's valuable to the market. People will pay you. That's what's really important. And oftentimes that's going to require you enduring hardship and overcoming challenge in order to actually accomplish anything.

1:07:12 Scott Ingram: Yeah, I love it. I love it. I think one of the mindset things I think from that perspective that I think is a good through line for this conversation is instead of it being, this is something that's happening to me, something that's happening for me. Yes, it's a challenge, but it's something I'm meant to overcome. Heck, we get this inside of deals, especially you get into these mega deals, you are going to have that issue. Probably a two dozen times at least. Why is this happening to me? Nope, happening for you. There's something you need to fix in this deal if you're actually going to show the commitment to get it done.

1:07:47 Rich Strobel: Yes, and frankly, that's some of the stuff that Jamal articulated in his book that I'm so glad I was reading it at the time because when it happened, it felt like I was really off balance and like, oh man, this isn't going to go. I'm not going to be able to land this one, instead of seeing it for what it is, just a necessary part of that process and something that's going to happen on this path.

1:08:09 Scott Ingram: Yeah, I had again some more great sales leadership relatively early in my career, and their guidance was, look, in a deal we're going to hear no 3 times. You were looking for it, and again, it was that awareness of what are the things that are going to go wrong. And sometimes it's an explicit no, no, we can't do it because does this. Okay, cool. This is what we have to overcome. Let's get really clear about what this is so that we can fix it. Or it might be just more of a procedural, like there's something else that's broken. So it may not be somebody is saying no to me, but something has gone sideways. But it's all fixable. You just have to stay committed to it. We can overcome this.

1:08:55 Rich Strobel: Yeah. The obstacle is the way. It's, uh, heard that's a book.

1:09:00 Scott Ingram: We're getting very Stoic in this. Rich, are there any other… I mean, you kind of walked us through your day. Are there any other kind of core habits or routines that are key to the way that you operate?

1:09:12 Rich Strobel: From a habits or routines standpoint, I think we've touched on a lot of the really important ones. From a mindset standpoint, I think that it's really important to yourself, what is it that you're trying to optimize for? Because you're going to have to make decisions. And having that kind of framework to make those decisions is critical. If you're good at what you do, you're going to have recruiters reach out to you. And I spent 5 years as a director of recruiting in the insurance business before I left there. And in the course of that time, I interviewed so many sales professionals. And it got to be pretty easy to get my point across. I knew what all the pain points were. The challenge is that the grass isn't always greener, man, on the other side of the fence, right? And I know that there's people listening to this that are gonna be like, yep, I figured that out the hard way. Didn't stick it out, went and left. This place was even more broken than the last one. I don't know if you'd agree with me on this, but the more clients I talk to, the more companies I'm at, the more I realize that Every business has serious challenges once you get under the hood. It's just a matter of figuring out what kind of problems you want to solve as you have to make these decisions about when is the time to leave, when is the time to stay and double down. Is my role in the company the right role for me right now? I think knowing what you're trying to optimize for makes those decisions exponentially easier for me. And I had to share this with my SVP and then later my chief commercial officer. Neither one of them knew that they had this conversation about a leadership role. And I said, no, I'm not interested in that right now. I'm real. I've done it before, done a great job, really enjoyed coaching and mentoring and have that heart. But right now I am trying to optimize for income, flexibility, and autonomy. And both of them looked at me and go, yeah, you're right. You just want to stay an individual contributor. Exactly.

1:11:08 Scott Ingram: 2 out of 3 of those things things, maybe 3 out of 3 do not align with you being in a leadership position.

1:11:14 Rich Strobel: And it's not that I'm not interested in that at some point in the future, especially with my oldest son where he's at in his life right now, the age that my kids are at right now, these elementary years. This time is so fleeting. It's so fleeting. I used to travel a ton, 60, 70% or more. I don't want to do that right now. I want to be around. I had the chance by knocking on doors to meet a ton of families from all across the spectrum, both in ages, professions, lifestyle, level of income. And that really informed what kind of father I want to be. And hey, do we have ketchup here? You don't even know what's in your fridge because you're never there. That's not the kind of dad that I want to be right now. I'm still at the age with my kids where in their mind I'm still still a black belt and basically an Olympic gold medalist when it comes to anything. That's very fleeting. Yeah, the glimpses are coming more frequently now. Ooh, they're gonna catch me on one of these. It's not gonna be good. In those days of being able to wrestle with them and keep up and exceed whatever they're doing sports-wise, there's not a lot of that time left, man. So I really want to be present for it. But that's me, and that's now me. This was not me 10 years ago or 15 years ago. Understanding what is it that you're trying to optimize for in your life right now will make those decisions easier. I think it's important to have an eye towards what do you want to build towards, because that also may play a role. You may want to take a role in order to set yourself up for something in the future. Personally, I don't at this point ever see an interest in being in the C-suite myself. But I know for a lot of people that's a really big aspiration. And hell, man, I think working in sales is one of the best primers you can get because you're so integrated across the different functions of a company. The level of understanding that you'll get when you do this well positions you very well for a C-suite role, I think. But for me, that's not something that I'm really interested in. So taking the steps to get there is just not on my radar at this point. And who knows, man, maybe 10 years from now that'll be completely out the window and that's the path that I'll be on. But for right now, I'm just trying to figure out how do I be the absolute best in this role without sacrificing the other things that are equally, if not more important. Is making $1 million in a year the ultimate goal for me? Not necessarily. If I made $800,000 next year but was present for my family and helped my son get on a good path at school, that would be even better, right? Making a million bucks, but then getting a divorce, your kids not having a good relationship. Like, I think to me, that's a misprioritization of goals for my life. So understand what you're optimizing for, and then secondarily, have an eye towards where you're trying to get and what's really important. I think that makes a lot of those decisions much easier.

1:14:15 Scott Ingram: Yeah, man, I love that framing and then that way to think about it. One of the things that I'm optimizing for right now as I build towards the summit and the way that we're structuring that this year is creating the space for people to think through those things and recognizing, to your point, they change. Like what it was 10 years ago is maybe different than what it was 5 years ago. For me, I'm rethinking a ton of stuff because my youngest is going into her senior year of high school. So I've got one more year and I'm totally committed there. I'm over-indexing on time with her because I know the ride's almost over.

1:14:52 Rich Strobel: Yeah, man.

1:14:52 Scott Ingram: But I also have an eye towards, oh, what's next? This really changes a lot of things, right, for my wife and I, for just where I want to be spending my time, where I'm able to spend my time, because I certainly have way fewer football game commitments and cheer competitions and actually have hobbies. Yeah, yeah, that'll be interesting. Again, I think it's important to not only have different frameworks and lenses like that, but just taking the time to step back and think about, wait, is this where I should be? Am I on the right trajectory? Am I on a path? Am I even being intentional about that, or am I just rolling with the punches and letting the tide take me where it's going to take me? And maybe I want to be swimming. Maybe I want to have a little bit of a direction here.

1:15:49 Rich Strobel: It's difficult because let's face it, there's hardly time to be strategic about our account plans when you're like deep in the day-to-day of just getting the deals done and building the pipeline. To make sure that they're replaced when they close. We used to talk about time spent working on the business versus in the business, and that's something that I've tried to carry forward now that I'm a W-2 of I need to carve out time to step back and really work on my business because I treat my territory… this isn't anything new, but I treat it like I'm a venture capitalist. This is where I'm going to make a massive investment, not of dollars, but of my time, which is even more valuable. That's a lot more finite. Not replenishable, but I need to take time to step back and really work on that business versus just in it day to day. But we also need to take that time to step back and look at ourselves and what is it that we're really trying to accomplish? What's really important to us and how do we get there?

1:16:41 Scott Ingram: Love it. Love it. Rich, do you subscribe to a particular sales philosophy?

1:16:46 Rich Strobel: I do not. No, I really like Sandler's line of questioning. I think that's really interesting when it comes to the med pic, for example. I really like the paper part of that. Because I think that's an easy hurdle that can absolutely crush people if they don't consider it, especially if you're working with larger and larger enterprise. I'm fortunate to work with the largest health plan in the country, but understanding their procurement process, I frequently am advising my business buyers on how to effectively navigate their own procurement shop because I've had to learn some really hard lessons over the years. Years by not accounting for that. I think it's in your latest podcast from when we're recording this. I can't remember the gentleman's name, but you guys were talking a little bit about this, that when you're younger in your career, some of those more formal processes and strategies are really important because you're building up this corpus of experience for you to draw on later. But as you go along, you're likely going to find that I like this part of that, but this other part just doesn't really work me. This part over here I really like from this process. So I'm going to Frankenstein these things together and figure out what works for me. When we were teaching people to sell door-to-door, we'd have these scripts and that now it couldn't be anything farther from how I conduct a sales meeting than going word for word from a script. But what I used to tell when I would hire salespeople from outside the industry that had a bunch of experience, what I would tell them on that is when it comes to your script, I want you to focus in this order. Memorize it, then normalize it, and then personalize it. Then and only then personalize it. Because at first you need to figure out what are the words you're going to say. Because if you don't know that, you're going to be dead in the water. You can't just shoot from the hip. Normalize it means make it sound like it's not a script. Actually deliver it not robotically, but in a conversational tone. And once you've got those 2 skills down, now you can start to really add your personal flair to it. So I think if we look at a sales career, a similar deal, pick something, look to a leader that you trust or hire one and learn something that is fairly structured and then get really good at delivering that and executing it, then you'll be able to find out where your own personal style can really emerge. I think it's too often that we look at tools instead of the skills behind them. And this comes to, from a tech stack perspective to whatever, tools amplify skills. If the skills aren't there, the tool's not going to save you, man. If you don't know how to prioritize your time, I don't care what crazy shiny new app you've got, that's not the answer. You got to figure out the skill set behind it. I love woodworking. I just bought a chisel It was $40. It was a really nice Japanese wide chisel. If I didn't know what I was doing, that chisel is not going to make my joinery any freaking better at all. There's a bunch of skill that needs to be developed, and once you have that skill, now a different tool can really amplify that skill. But you've got to develop the skills first, otherwise you're just wasting your money and your time. So when you think about this tool versus that tool, I think it's really important to think about skills being talent is something that can be really innate, but the knowledge and then repeated application, those 2 things you have to work at. So talent can amplify the skill, but you've got to have the repeated application of it and the just bottom line knowledge of what you're doing. That's what will really develop your skills. And once you have those skills, now you can start shopping for the right tool to really amplify them.

1:20:24 Scott Ingram: Yep. They say a fool with a tool is just a bigger fool.

1:20:28 Rich Strobel: Make bigger mistakes faster. Yeah.

1:20:34 Scott Ingram: So, Rich, we got to one half, one side of the question. You jumped ahead and shortcutted the thing that a lot of reps believe that you think is crazy, that maybe society believes.

1:20:44 Rich Strobel: Yeah.

1:20:45 Scott Ingram: What about the flip side? Is there something that you believe that other people might think is crazy?

1:20:51 Rich Strobel: That's tough to say, man. A lot of the things around… I think that there's been a lot of popularization of some of these things that were pretty contradictory. A number of years ago. I think Brandon has done a really good job of just shining a really bright light on hustle culture and how damaging that is. But I would say something that I really believe that other people might discount is the value of who you are outside of work is a critical component of who you are when you show up to work. If you're not doing the things that you need to outside of your professional life, is going to suffer from it. If you don't have those strong relationships, if you're not spending time taking care of yourself, again, this isn't anything that's super revolutionary at this point, but I think there's still a lot of people that don't quite get it. Like, PTO is really important. And we love to laugh that PTO stands for partial time off because you got your laptop with you and you're probably logging in 8 times over the 4 days. And there's a part of that, like, for Jess and I, the way we talk to each other about it is both of our careers are at a point right now that for us to travel the amount that we like to travel, we can either take less time off and have it be completely like shut off, or we could travel more. And it just might mean that like, Dad's going to work this day of vacation. So we're going to have these couple days that Dad's full-time engaged. We'll have dinner with him this night. And then these days, he'll be fully engaged, but he's going to spend some time working because that's what it takes to keep certain things moving along. I try to balance it out with… there's times where I'm just like up in the Northwoods and there's no reception. That's very intentional. I mean, I need that time to really get centered and replenished. But then there's a lot of other trips that we wanted to take 2 weeks in between Christmas and New Year's a couple of years ago while the kids were off of school. We could do that, but I've got some deals that need to close, and that's a really critical time of the year. So we can do that, but we need to make sure that we're staying in a place that I have really solid Wi-Fi, that I've got a place to actually set up and be productive. And I'm going to buy an external keyboard and a little travel external monitor so that I can get the cockpit going and actually be super productive in a remote location from my normal office. These are just considerations that we have to make if we want to do those things. Things.

1:23:12 Scott Ingram: That's a really interesting idea of making the choice of which one is this, because I have certainly tried to be more intentional on the I'm going to completely check out, but setting up for that, right? So that's giving a heads up to my key clients and my biggest deals, I'm going to be out this period, right? One, it allows me to create some urgency. Okay, we got to get this done by this date. I'm going away. I'm going to create my own deadline. In that way. I think it starts with communication, then there's backup, right? Then there's having team that you can lean on. So who are the people that I'm going to name and give contact info for in my out-of-office message? That if you need this, it's this person. If you need that, it's this other person. If it's this other thing, and if, oh my God, the world is ending, then and only then are you allowed to text me. The brilliant thing is I don't hear from anybody Again, it's setting the expectation. The internal communication is I'm 100% off the grid. If the world is ending, sure, you can text me and I will come up for air. But I think setting up that structure for yourself, it works. And again, being cognizant of the time. To your point, if it's the end of the year and you're on a calendar year, that's probably not going to be like, I'm going to completely check out for 2 weeks. You're also not going to make your number. Maybe that's what's a little easier to do in July or August when I also know my clients slow down.

1:24:39 Rich Strobel: Yeah. And I think being intentional is 95% of the battle in that respect. But I will say this, when it comes to knowing which role and which company, these are things that you should probably think about a little bit. Do you have the support structure? To be able to do that. If you've got unlimited PTO, that's great. Unless your leader is going to hang it over your head every time you take some of it.

1:25:05 Scott Ingram: Yep.

1:25:06 Rich Strobel: Are you going to have… do you have the right team that you can actually be out and you've got people to delegate to? Or are you a one-man show and it's a startup and if you don't do it, it ain't happening? These are other things that I think are important to really consider about the role that you have in the company that you're in that role with. And it's one of the reasons I love smart data so much. Our CEO is the best CEO that I've ever worked with. And part of that selfishly is because he spent a lot of his career in a sales role and he sold really big deals at the highest levels. So he understands it and he's on board with orienting the company to get deals done. That's not everywhere. A lot of times when you have a CEO with that kind of experience, guess who has to close every flipping deal and they got to get involved involved with everything. Having leadership that actually cares about who you are and your family and is ready and willing to help you accomplish those things and do it in a balanced way, I think those things are really critical, but often easy to overlook when you're just looking at dollars and cents. For example, my quota went up and my territory went down, so now I got to go do it somewhere else. You might miss out on some real momentum that you've created If you just jump ship at the first sign of challenge.

1:26:19 Scott Ingram: Yeah, I love the intentionality focus here. Let's carry that over to the advice that you would give to somebody that's just starting in their sales career. How can they be intentional about setting themselves on a path to sales mastery?

1:26:35 Rich Strobel: I think listening to podcasts like this one makes a big difference because you've got to find people. That have done what you're trying to do already and learn from them. The good news is that this isn't the cutting-edge pioneer. We're not exploring deep space here. People have done a lot of what's trying to be done already. And now more than ever, there's platforms where they're just ready and willing to share. And it's not just you're stuck with this certain bookshelf in the bookstore that you got to pick from. And half of these authors have never carried a bag in their life, so they're even know what they're talking about. These are actual people that have done it, and a lot of them are doing coaching. There's a lot of great podcasts, a lot of them write books. So I think developing a thirst for knowledge on that path is really important. And going back to the personal C-suite, it's really easy to think of investing only in terms of what do you plug it into your 401. The next level up is, oh, now you're going to buy some investment property or you know, these other things. And I think a lot of times people overlook investing in the best asset that you have access to, which is yourself. And the reason that I'm so adamant about having this personal C-suite that are on my payroll is because then their loyalties are to me. Nothing against a great manager or a great leader or a great chief of whatever in your company, but at the end of the day, when push comes to shove, Their loyalty has to be with the company, not to you. And you've got to understand that. This is what we signed up for by taking a W-2 role. Our ultimate answer is to the board. So that's where we have to make decisions in the best interest of what's best for the company and best for our investors. That might not be what's in my best interest, right? It's important to find the team that strikes the best balance of that. But I think when it comes comes to your personal C-suite, you need to look outside your organization for that reason, but also for the reason that an outside perspective can make a world of difference. Oftentimes it's easy to just get stuck in what you do every day and how we do things here to miss that it's actually just a slight adjustment, but you're too close to the forest to see the trees. Having that be outside people that have done it before, they've helped other people get to where they want, 'Cause that's important too. The best doers are not the best coaches. I think that's an important one too, is they've done it and now they've helped other people do it. That's what I'm looking for. And that's why I've selected the people that I have.

1:29:08 Scott Ingram: Love it. Does that advice change at all for somebody that's further into their career and is either, yeah, I'm good, but I haven't gotten to great, or maybe they're just dealing with a dip?

1:29:19 Rich Strobel: I think it's very similar to growing a company. What works to get you from $5 million in revenues to $50 million is not going to work to get you from $50 million to $100 million. And that's not going to work to get you to $1 billion. You've got to have oftentimes different leadership, different strategies. All that changes as you get to different levels. And I think it becomes even more important for us as we reach higher levels of accomplishment in our role to step back and reevaluate Is this the right team to get me to this next stage? Because what got me to here may not get me… I can distinctly remember being young and be like, man, once I make $100,000 a year, oh, it's gonna be so awesome. It's gonna be so much money. You get there and you're like, where the hell is all the money? This is not… this is not what I thought it was going to be. And that applies, right? You keep growing and you get there and you're like, man, this isn't quite the way I expected it to be. But what do I need to do to now hit the next thing? And that's part of who we are as just people, right, is we always aspire to more. But I think it's really important to reevaluate who is the team that you have around you, what are the processes and things that you're doing, and does that also need to level up in order for you to hit this next level of accomplishment?

1:30:33 Scott Ingram: Nice, nice. Rich, we covered a ton of ground. Is there anything that we didn't touch on that you hoped we would?

1:30:42 Rich Strobel: Looking at notes here, man. I think we hit on a lot of the stuff that I wanted to make sure that we talked about. There's more stories that we could go into, Scott, but you'll just have to invite me back or something.

1:30:53 Scott Ingram: That's what beers and the summit are for.

1:30:55 Rich Strobel: Dig it.

1:30:59 Scott Ingram: Let's wrap a bow on this baby then. So you know that I always like to make it as actionable as we can coming out of it. So what would you challenge our listener to do over the next 1 to 2 weeks to improve themselves and improve their results?

1:31:12 Rich Strobel: Yeah, I think first and foremost, understand what it is that you're after. What are you actually trying to do? And then start putting the pieces in place to position yourself well for that, because I think it's too easy for us to forget all the things that we do to chase a deal and turn around and apply those things to ourselves and to the rest of our lives. I used to actually spend a little bit of time working with talent and placing them. So I went from hiring salespeople to then placing salespeople before I started with healthcare tech. And it was amazing to me how often I had to say the stuff that you do when you're trying to win a deal, like the account research and knowing your presentation going, you need to do that for this interview. You need to do those same things, understand who you're talking to, what it is you're trying to get across. So just applying those things. Know where you want to go and then start putting the pieces in place. And if finances are a challenge right now, there's a lot out there that you can do that doesn't cost you anything. It's the intentionality, not the dollars that you spend, that will make the bigger difference. So start putting the pieces in place. Start seeking out mentors if you can't afford to hire them. Start listening to their stuff. A lot of them are doing a lot of value-added stuff on LinkedIn and on YouTube. And on podcasts. Start to collect that information. Be intentional about where you're trying to go and what it's going to take to get there.

1:32:36 Scott Ingram: Brilliant, Rich. This is awesome. Thanks for taking the time in.

1:32:39 Rich Strobel: Absolute pleasure, Scott. Thanks for listening to the Sales Success Stories podcast.

1:32:45 Scott Ingram: To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.