This time on Salesforce Trails and Trials, hosts Jon Cline and Erik Yewell talk with Tyler Cobbett, a tech industry veteran.

Jon Cline has been working in IT since 1998 and is a very curious person. Erik has been in IT for 23 years and done just about everything you can imagine. They share their wins and worse so you can learn with them.

Tyler Cobbett started out with IBM in the early 1980s and has had a long career that moved from sales to solutions, eventually focusing on Salesforce consulting. He’s now moving into retirement, which presents an opportunity to share what’s he’s learned and focus on other interests.

Rather than the typical show notes, we’ll present the entire interview transcipt.

Interview With Tyler Cobbett

Jon Cline: So, Tyler, welcome. We are so excited to have you on this episode of Salesforce Trails & Trials. This is our first opportunity to—as we’re walking up the mountain, somebody is walking down the mountain and can tell us, hey, these are the trails to take, these are the views to make sure to take, the spots to go slow, and here’s what the peak is all about. So we’re really excited to just learn a little bit about your world. And not just the Salesforce world, but how you got into this and the things you love about it. So really excited for you to be with us today. Maybe we start with you just giving us a little bit about yourself, your current interests—just a few minutes so we get to know who is Tyler Cobbett?

Tyler Cobbett: Absolutely. Well, part of my story and my background is growing up outside of this country in Canada, I grew up in Montreal and started my business career up there. And I’ve been in the States since 1997. But, you know, professional life is definitely a big part of what I do. But I also subscribe to skiing, sailing, hiking, coaching, mentoring, and volunteering, and music outside work as well.

Jon Cline: Very nice. I went to Cirque du Soleil and every person I ever met that was part of that circus—guess where they were from? Montreal. Let’s go back, way back in your professional world. I’m curious, what was your first role? What was your first job where you feel like it was a real job, not a paper route necessarily, but something that you feel may have led you to the Salesforce world?

Tyler Cobbett: Jon, I started in the mailroom, literally, at a company in Montreal that was in the glass industry. They made the glasses for use in restaurants and homes. They made glasses for Coca Cola, things like that.

Jon Cline: Drinking glasses.

Tyler Cobbett: Drinking glasses, there you go. Thank you. And I learned how a business function from the perspective of a guy delivering mail to the salespeople, the finance people, whatever. And so that was really my first sort of show up in a suit work. But really my career started at IBM as a summer student for two summers.

Jon Cline: As a summer student? So tell me, what about that role at IBM? What was your responsibility? Was that like an internship? Or was it a part time position?

Tyler Cobbett: Today they would call it an internship, back in the day you were just doing a summer job. Started after after school after high school finished and went through to Labor Day. I was part of the sales organization. I would cover people’s territories while they were on vacation—prime in the six weeks in summer. I was basically getting to be a sales assistant to those people in the sales team.

Jon Cline: Nice. So thinking back on that role—that’s really cool it was in high school, what a great opportunity. So thinking back to that role, give us like an anecdote or some kind of great experience you had there that taught you a really cool lesson.

Tyler Cobbett: Many, very many formative [lessons]… One was that this was a bilingual environment. Another summer student, a guy named Andre, who actually helped write a script for me when I had to do telemarketing for them. And I was calling into rural areas of Quebec where the language was very difficult to understand. And I was coming across as a real newbie speaker, but it was very character building to humbly try to understand the language and function in that language. And, you know, certainly when the tables are turned and you find yourself across the Zoom screen from somebody whose first language isn’t English, it’s thought provoking, and it causes you to be more empathetic to the plight of people who don’t necessarily communicate in English as their first language. I also think that I was inspired to work hard. I saw how professional those people were, how committed they were, how much money they were making, and I decided this is something good really interested in. So I’m going to hustle. And I decided to really go for it and it paid back.

Jon Cline: Very cool. So when you when you say it paid back, did you continue? What was your next role in there? Did you continue at IBM like after the summer?

Tyler Cobbett: Yeah, sure did. When I left college, I only interviewed one place—IBM. I had gotten some good reviews from the salespeople that I helped out and so they were willing to provide references when I was trying to get hired there full time, which in 1982 we were heading into a recession and wasn’t the easiest time to get hired. So it was very helpful to have had that experience. But really, the work that I was doing when I joined IBM full time was similar to the work that was being done by the guys and gals that I was supporting.

Jon Cline: Oh, very cool. So the transition from the mailroom into kind of being sales support—this is just when they were on vacation, you would step out of the mailroom?

Tyler Cobbett: Yeah. Actually, it was two different jobs. The drinking glass company was sort of my first exposure to corporate white collar work. And then moving to IBM was just straight into the bullpen, sitting among the salespeople, and standing at the water cooler with them and telling jokes about hockey and whatever else is happening over the weekend.

Jon Cline: Nice. Very cool. That sounds like an amazing opportunity. What I observed is that both in the mailroom and going into the bowl—you’re inundated right in the mailroom, you’re inundated with stuff, and handwriting you have to figure out and where things go. And then in that sales capacity, I imagine, you’re inundated with lots of different personalities, people, and they must have seen something in you to retain you, especially in that in that tough time—I do recall hearing about those years, right when I was but a wee lad.

Tyler Cobbett: Yeah, it was really important to have had that experience. It gave me a leg up, I think, coming into IBM with just a skinny little undergraduate degree.

Jon Cline: So let’s fast forward a little bit now and talk about how you made your transition into consulting, where you’re now working on specific client projects?

Tyler Cobbett: From the get go back in the day, IBM was really as much in the software industry as it was in the hardware industry, way beyond operating systems. The division that I worked in was selling mid-range computers. And you couldn’t sell mid-range computers without application software to run on them. So they had a manufacturing system, and they had a financial system, and they had a wholesale distribution system. So I got 18 months of training from IBM to learn what a bill of materials was, what a financial statement was, and learned a lot about business so that I could act as a more effective salesperson. In those days, as you as you know, software was very, very simple, it didn’t do as much as it did even a few years later. So that a salesperson was expected to be able to go into a client’s office and talk about business and really talk about relating clients business problems to what the software could do. And so that’s really what got me started as a software consultant. It was only when software started to get so big and so functional that the element of specialization came along. And really, an individual couldn’t wear all of the hats of being both the salesperson managing the sales process and also doing the solution consulting at the same time.

Jon Cline: So that’s fascinating, Tyler. You went in with a sales role, and you were expected to be a well-informed salesperson, who could do some discovery, understand the landscape, and then really sell out of that insight that you had because of your background and training in the software. Did I understand that right?

Tyler Cobbett: That’s right. The basis of really my entire career has been understanding business first and understanding technology second, and the success being in the intersection between those two things.

Jon Cline: What’s great is that in my years of knowing you, I didn’t really recognize you as a typical salesperson, but with an informative, guiding, kind of discovery and question-oriented—I can totally see how you would have knocked it out of the park. So I’m curious, as you think about that role with IBM as a salesperson, was there a point where you saw one side or the other side and said, ‘You know, what, I liked the sales side, but I really liked this aspect of going deeper with the software that I’m selling.’ Help me understand that transition a little bit.

Tyler Cobbett: Yeah, as it turns out, I was not a gifted salesperson, because the gifted sales people, they loved arranging after-work events for the clients, and they loved pulling together meetings with multiple different stakeholders, and they loved going for the close, and they loved asking for the money. I was way more interested in the solution. I really was compelled to try to listen to what the client was after and see if I could find a way to align the software solution with the business problem. My destiny was more on the solution side. So I left IBM after four years and went to an ISV that happened to be in the IBM mid-range space. But they had their own solutions focused on a specific niche in the business spectrum that was wholesale distribution. And I was able to really prolong the ability of being a salesperson, but focused exclusively in this business niche. So I got to do that for a few years, got to experiment with sales leadership in that role, but managed to stay in touch with the problem solving aspect of the job.

Erik Yewell: I had that same dilemma in my career, and I chose the technical path. But there was a point where the question in the interview for the sales role was, what energizes you? And the wrong answer, which I gave, was the solution. That’s the wrong answer. That’s not what a person who is going to hire you for a sales role wants to hear. Maybe it’s solving customer problems, but it’s also like the money. My experience with salespeople is money is openly a key part of what you like, and I’m authentically a solution person.

Tyler Cobbett: You chose wisely.

Erik Yewell: Thank you for reaffirming my life choices through your own.

Jon Cline: Yes, we are all in that fraternity. You had a series of managers along the way, people that saw something in you, people that encouraged you to do something, they were investing in you… I’m curious if there was a moment or an experience you had with one of those managers along the way that really helped to kind of promote this clarity and this series of steps for you.

Tyler Cobbett: There were many. I was really blessed to have managers at different stages, different inflection points. Early on—now we’re talking about this second company that I worked for, this VSP—they were really interested in investing in their people. And they actually went to the extent of giving me access to what I called a business shrink—the person really behaved like a psychologist who gave me the Myers Briggs test and wanted me to understand what it meant to have different aspects of my personality and how they could affect how I interacted with others in the workplace. He held my hand as I went through this leadership training. How is your experience? What was good, what was not good? What did you learn? What do you struggle with? So I think that company, this team—Gary, and Mike were the two guys—by investing in me, showed me a lot about myself, and definitely increased my value to them as well, but they really, really helped me to understand myself and my strengths.

Erik Yewell: I’ve had one of those too and my finding was you need that, for me at least, you need it once, and it sticks. It’s not like you need to go through it more than once. Learning about personality types and how people communicate is so important to moving from individual contributor and sort of not great communicator to great communicator and that’s the path you can keep going on forever. But I love learning about public speaking and these things like Myers Briggs, or, you know, the psychology of work. It’s pretty cool.

Jon Cline: Now, that’s good, because one of the things we wanted to ask about, Tyler, is those people first components. We believe to be a successful consultant at Salesforce, you’ve got to have high empathy, be able to recognize things in people there’s all those intangibles. And so what I hear from you is that the first thing was really understanding, ‘Hey, this is me, let me understand myself better. And if I understand myself better, that gives me the kind of contours and facets that I can begin to see other people and figure out where they are on these fronts, so I can better connect with them.’

Tyler Cobbett: Yeah, you’re right. In a way that experience equipped me with some tools that I didn’t have previously, both to evaluate and manage myself, but also to evaluate and manage others, how to interact with them.

Jon Cline: So when you think about that, whether at IBM or that role at the ISV, was there a particular solution that you had to deliver that just kept you up at night, that was a stressor? What was the insight that you gained from it?

Tyler Cobbett: That’s a good question. Again, I was on the pre-sale side.

Jon Cline: You were a solution engineer?

Tyler Cobbett: No, but delivery aspect of things was different from being on the post-sale implementation side. But still, I was interacting with the implementation team, the project managers in particular. There are many anecdotes from that time. I learned the art of being a project manager. I watched this guy of Jamaican background, his name is Howard Davey. Howard had an amazing sense of humor, he was self deprecating, he was always smiling—but he had huge technical skills. And what was great about Howard was, at a point in a project where things were coming off the rails, Howard would listen carefully, there’d be a deathly silence as the anxiety in the room rose. And then Howard would throw out some Jamaican quip, you know, ‘Boy, this makes me feel lower than a plantain.’ And his genuine sense of humor would defuse the tension in the room and help people focus on this and win scenarios. What I took away from that was it’s important for people to know you—warts and all—in business.

Jon Cline: When did you first discover Salesforce?

Tyler Cobbett: Erik may be the guy or may know of the guy. But I worked for an early SaaS pioneer that had a partner relationship management solution company was called Aegis. We sold cloud-based partner relationship management solutions to Logitech and HP and this long list of pioneers in the early 2000s. Somewhere in the early 2000s, we adopted Salesforce for our internal use. And somewhere in the 2003, 2004, we lost our first deal to Salesforce. And that was where Salesforce got onto my radar. And we lost because the client was less interested in our domain expertise than they were in our architecture. And that was really compelling to me, because I realized that we didn’t have that and we were never going to have that same degree of tailor-ability under the control of an administrator. So that really got my attention. Fast forward to my next role as a sales leader, I implemented Salesforce as one of those accidental admins for a small team of three people and really caught the bug—just loved the flexibility of the intuitive way to work with it. So that’s really how I got into it. The next stage was that I ultimately founded my own company to do sales process consulting and went out to the market saying, ‘Hey, you guys need sales process improvement, if you need sales execution help, I’m a guy with 15 years of sales background, big companies and small, let me help you.’ They were not interested in that offering. But they were interested in figuring out their CRM systems. And so that was really what closed the deal for me to invest in my own Salesforce career.

Erik Yewell: Having that connection with CRM makes your consulting tangible. It’s nice to have a sales methodology, but unless your sales methodology is tied into your CRM, it’s really hard to make people do it. And I can see them going, ‘Yeah, yeah, I just I need you to make it part of what we do every day.’ So I can totally see how tying yourself to Salesforce or pick a vendor of the time—CRM was kind of picking up in small business then because in the ’90s, CRM was an enterprise tool. And there wasn’t a lot of CRM, there was a Goldmine, maybe Act, but really that was an upcoming time for CRM and same for PRN too. PRN started at Salesforce in 2004. And that was just early days and a great way to get people to get the process into something that people actually use.

Jon Cline: So Tyler, I’m curious, as you were a sales leader and that accidental admin, put into that role of taking on this extra responsibility, was that something you were excited about? Or is it a little bit like, ‘Oh, I have to do this, too?!’ What was your attitude?

Tyler Cobbett: I think I was secretly nerdily excited about the opportunity to not only build this thing in my own image, because I had had a bunch of best practice training. So I thought, this is my chance to really build something that will function and give me the reporting that will help me run this sales team. So I think it was probably really, really exciting to me, and it really convinced me of a nerdy aptitude for systems and my sales background.

Jon Cline: There’s a good litmus test there for people who might be considering a Salesforce consulting future, when an opportunity like that does arrive and it makes itself visible, what is your disposition toward that? If you have that curiosity and as you said nerdy enthusiasm, then that might be a good sign that, hey, this Salesforce thing might be a good part of my future. Because if you dread that kind of thing, and all the learning that’s involved with it, then yeah, a Salesforce career might not be a good fit.

Tyler Cobbett: The great thing today is that you can come from so many different backgrounds, clerical backgrounds, in marketing, in supply chain and finance, in healthcare, certainly in sales, of course, and still have those skills be valuable background to draw on when you go into consulting.

Jon Cline: When you when you have that sales team, and you’re essentially managing these people and then also thinking about their own performance metrics and how to kind of keep things moving forward, was there anything you of thought at the time, ‘I wish I would have done this earlier’? Maybe something you did in that moment to help provide for them or do whatever it might be. Was there anything that you look back and you were like, ‘If I would have done this earlier I would have done much better in that role’?

Tyler Cobbett: I think that’s a really good question. Maybe I can take two shots at this one, because what really occurred to me when you were posing that question was that happened to be a battlefield promotion, that happened to be the first of two battlefield promotions that I’ve experienced, in both cases, not because of me, but because of other reasons within these companies. My boss left within the first 90 days that that I worked for those companies and so their jobs were offered to me. And I gladly and gratefully accepted those jobs without asking a single question. So what I would do differently in the future in that situation is just try to draw out the process a little bit to ask questions, not only of the leader who was offering me this position, but also of the peers and colleagues that I was going to need to lead. Because without forging those kinds of alliances with the people that I was going to need to lead, and without really understanding the expectations, and the reasons why my bosses left, I wasn’t able to perform as well as I might have if I had taken more time from the very get go.

Erik Yewell: Did you go from individual contributor on that team to becoming the manager? So are you saying that you would have tried to take a week and sort of shop around the idea to say, ‘Hey, would you ever want to change this team?’ before you let people know you’re about to become manager? Is that the kind of approach you would take? What would what would be some example? Not the stall tactic, but the recovery tactic—the recon?

Tyler Cobbett: I think just as simple as talking to the people that I was going to be put in a position of leading and saying, ‘Hey, are you OK with this? Do you support me? And if you do, great, but what are your concerns, considerations, aspirations, what’s important to you?’ Just sort of engineering the environment, because what was missing was the sponsorship and the support of the person that brought me into the organization. So I was in a political vacuum with no particular means of support. So I think I would have engineered a bit of, ‘We’re all in this together, one of us needs to lead. I’m OK with doing the leadership thing, as long as I have your support.’

Erik Yewell: It’s such a frank conversation. I can see people getting uncomfortable, but at the same time, you can not have the conversation. I think having it’s probably better than not having it. That’s good.

Jon Cline: It’s good. And it probably gives you a little bit of insight into like, ‘Man, this is totally a bed of nails. I’m not going to get into this. I’ll just keep being an individual contributor and let somebody else figure it out.’ Right?

Tyler Cobbett: Absolutely.

Jon Cline: So you had a good crash course in Salesforce with—you didn’t you didn’t even have Trailhead at the time right?

Tyler Cobbett: Nope.

Jon Cline: Talk to me about how you went about that process? You were on a timeline, right? You had to learn the product, figure out how you’re going to deliver it to your team, and then deliver it to your team, and then onboard your team to it all while doing your leadership role.

Tyler Cobbett: Yeah, it was a long time ago, so I don’t remember a lot of the details. I’m sure I’ve suppressed some of the more basic ones. It was a very simple implementation for starters. So there were no security issues to deal with. I don’t even know if Salesforce had much—

Erik Yewell: Profiles.

Tyler Cobbett: Yeah, profiles back in the day. So no, Jon, it was pretty straightforward from a technical perspective. It was more about getting the buy in from the team to put their opportunities into the system and use Salesforce to create the sort of common language or common infrastructure.

Jon Cline: When you had to make the pivot from trying to sell sales process improvement—people are not interested in that, but they are interested in CRM. Was there an element or a method or something that other people might gain from how you went about gleaning all the information you needed to to make that pivot and to begin selling technology services instead of process improvement?

Tyler Cobbett: I think the biggest takeaway is that if you decide to go out on your own, and I highly recommend the idea of starting your own business, it’s been a life changing, delightful experience for me. But if you decide to go out on your own, and I’ve talked to this to other entrepreneurs about this, you can have a thesis as to what the market needs and wants, but you really need to listen to the market for what they are willing to spend money on. And it was clear that VPs of sales in startups really didn’t want to bring in an outside VP of sales to sort of yield that maybe they didn’t have all the answers. It takes a very enlightened sales leader to bring in somebody from outside to make recommendations on sales process. But what they really, really needed was help from somebody who wasn’t technical first, who could speak their own language, who could talk about pipeline, who could talk about wins and losses, and sales cycle lengths, and all of the stuff that was second nature to me, and that could apply it to the technology. So I think the lesson to somebody entering this field is choose an area where you have some business familiarity. And if you don’t, that’s OK. Go get a part time job, volunteer at a place that does the kinds of things that you’re interested in doing, but develop some familiarity with the terminology and the processes so that when that client asks you how would you do this, you can say, ‘Well, when I was doing this particular thing, this is how I solved the problem.’

Jon Cline: I hear that sense of being a contributor, be a contributor in some area where you have that expertise before you go in and consult on people who are also in that area. And I love the second thing you’re talking about, which is just the power of the anecdote, the power of the the story to be able to tell and say, ‘Hey, we have this situation, this is what we did. This is what we learned. And I think that relates to this.’ I think people learn so much better through that storytelling around your prior experience than any kind of abstract features and possibilities and capabilities. I also love how you’re a very relational guy. I’m big advocate for being self employed as well. But I also love that you are a people person. People don’t have to interface with you, they can just talk with you and you speak their language You can engage them on their own terms and lead them at the appropriate pace into learning these additional aspects. I’m curious on that point, as you looked around, and your peers and things like that, did you find that was fairly common in your kind of your endeavors of these various organizations?

Tyler Cobbett: Pretty uncommon, Jon. You are one of the great examples of people that I’ve met. Gosh, I think of other people that you and I have worked with professionally. Crosier is an example of a guy who is a really quick study when it comes to understanding the motivation, the business aspect of things. But yeah, it’s rare. And I think people who have not had the luxury of working in a related field to where they’re doing their consulting, it’s much harder for them to go down a path of discovery when they don’t really understand the underlying nature of the business that they’re consulting to.

Jon Cline: I think the motivations, that’s key. I think the highlight there for me too is just understanding all of this is a means to an end, these things are not ends among themselves. But there’s something beyond this, and there’s something ahead of this. So understanding the bookends of what are the motivations that are driving all of this? And what are the goals and outcomes that we really are looking to seek beyond this? Sometimes somebody wants a promotion, they’re doing this project, because they want a promotion. Or they want to retire. They want to have something that they can pass on to somebody else. It’s not just about the P&L and revenue or things like that. There are very personal concerns that people want. The office manager wants to stop being at every beck and call of the management when they can do these things themselves.

Tyler Cobbett: Well said.

Jon Cline: So after you got into Salesforce a bit and you implemented it the first time, there are lots of additional platforms that have come into the marketplace. You have Oracle, NetSuite, etc. You came from IBM, you did lots of other software stuff, what were the couple things that made you say Salesforce is the platform, even in the midst of all this emerging competition that I’m gonna stick with? And I’m gonna keep going deeper and further with?

Tyler Cobbett: That’s a great question. I had the great fortune to go and work for SAP, a big enterprise software company. And SAP, in the late ’90s, invented a product called R3, which was the first client server, enterprise-wide software system that was available. Because prior to that all of the large systems were based on mainframe types of architectures. Client server was the thing and they had the only game in town and the market embraced them. They couldn’t sell them fast enough, they were so successful they actually had to defer interest from some of their prospects, to the chagrin of those companies, and say, ‘hey, look, we don’t even have time to market to you right now, we’re only after people that can do million dollar deals.’ And so it gave them the perception of being a little aloof and in some cases to not be advantageous. But the bottom line was when I looked at Salesforce and I saw that they had not only the technology but the culture that it was going to take to create a similar level of demand and this wave of of success that SAP had—it was a no-brainer. I said, ‘I’m going to ride this wave as long as I could.’ I never expected it to last with the same intensity as it has for 20 years. It’s just been fantastic. And it’s a huge credit to the leadership of that company to keep growing, to keep their ecosystem healthy and engaged. So that was really what kept me there. I realized that it was really the best solution in the market when you considered all of the different aspects of using systems.

Jon Cline: Now you also had a very unique opportunity, I think you said you did Salesforce school every Sunday morning in your house—I’m just kidding. You’ve had the opportunity to bring in some of your children into the ecosystem. How did that begin?

Tyler Cobbett: My daughter, Kate, graduated from college with a bachelor of science in biology. When you graduate, as a biologist, you have a couple of career paths you can pursue. You can head down the health delivery path, go into the healthcare system, or you can go into more of a lab research oriented path. And so she was really struggling. She was consulting friends and other other advisors to help her decide which path to take. And while doing this, she was working at the Oregon State University bookstore in Corvallis, Oregon, making minimum wage. She got a large promotion so that she was the manager of the bookstore, but still she was making slightly over minimum wage. And so she had complained to me one day about just how hard it was to make ends meet. And I said, ‘You know, I can triple your hourly income in about 90 days. And I can set you up to make a lot of money within a few years. It’s the Salesforce thing.’ And to my utter amazement, she expressed interest and I was able to hire her into my company in stealth mode behind the scenes to help out on a few projects. And she caught the bug and she was damn good at it—turns out the same brain that one gets to remember all the parts of the body is useful in remembering all the parts of the Salesforce system and how they fit together and flow from one to the other. So yeah, that was how she got started.

Jon Cline: That is so fun. I’m sure it’s a dream for many parents to be able to enjoy time with your kids after they become young adults and professionally and to be able to work on a project together. I wonder if you can share a story of a triumph that you guys had together, maybe it was a tough solution you’re trying to work through or a tough client, something that you guys accomplished together.

Tyler Cobbett: One of the greatest triumphs was early on. She had been doing this now for maybe six months or so, not long. She called me up one day and said, ‘Dad, I just don’t understand why people are willing to pay us the kind of money that they do for doing work. It’s so easy.’ She said, ‘I’ve cleaned houses, that’s hard. But they don’t pay nearly as much for cleaning houses as they do for doing this easy Salesforce stuff.’ And it was just such an aha moment that this young woman who had gone through high school in Palo Alto and had gone through this small school—liberal arts, college education—had completely taken for granted, living in the Silicon Valley, the value of her soft skills, her written and verbal communication skills, her problem solving, just her basic get up and go, that those things had value in addition to any technical hard skills that she might have. That was an enormous aha, and still is a great source of just satisfaction for both of us.

Erik Yewell: Did you find that your relationship had changed with your daughter once you have this thing in common? You probably had things before you could talk about, but did this add a whole new dimension to your relationship?

Tyler Cobbett: Oh, gosh, Eric, it’s the dream of I think of any entrepreneur to get up in the morning, go to their restaurant, to their hardware store, to their place of business, and be able to share that experience with a member of their family. And to not only know and see Kate developing as a professional, building certifications and experience, and know her better, but also to have her know me better and be able to see me in action in person, being on the same Zoom call solving problems for the same client is just an extraordinary gift. I’m so grateful.

Erik Yewell: I had not much in common with my dad, he was in sales and I was an IT consultant. But when I became a sales engineer, and he hadn’t used Salesforce, all of a sudden, we had this thing that we talked about at dinner all the time. And to this day, I was visiting this weekend, and he asked me how things were going. As a sales manager, he’s always asking about what’s the sales cycle like, and is the AE doing this? Or is a salesperson doing this? Or what are you doing? It’s just a great thing as a kid to have that in common with your parent. Because I noticed that changed that we had so much more to talk about. Not that we struggle, we’re very close, but there’s something of the enthusiasm, which is shared enthusiasm. It’s like having a hobby in common.

Tyler Cobbett: Yeah, there’s a connection that doesn’t exist otherwise.

Jon Cline: You’ve moved into kind of partial retirement now. What was the driver? How did you know that, ‘Hey, this is time to transition to doing some other things in my world.’ Help us understand that decision.

Tyler Cobbett: That’s a great question, Jon. There’s some really pragmatic aspects of things. Software consulting is hard, it’s grueling. In order to make money in this business, it requires not only investment of time on projects, but in a sustained way over weeks and months. Always putting your clients interests first. That’s hard work. It’s hard, hard work to do. And so having done it for 12, 13 years, I definitely was feeling the accumulated wear and tear that that brings. Now, I say that in the context of letting you know that I didn’t just work, I did everything that I could to bring balance to my life, playing music working out a couple of times a week with a personal trainer, eating well, sleeping well, all of those things. Because you can’t function professionally if your body and your mind are not at 100%. So in spite of doing many of the right things, I just realized, ‘Hey, I’m, I’m 62 years old. I’ve been working for almost 40 years. And I got a lot of things that I want to be able to do in greater quantities.’ And so it was a pretty easy decision, Jon. I’ve got the support of my wife to be able to just say, ‘Hey, I’m retiring.’

Jon Cline: That’s beautiful. Well, we have a few minutes left, so I thought we’d ask the questions that we asked on the podcast as part of our segments. So what have you learned lately? Doesn’t have to be about Salesforce, you can do whatever you like.

Tyler Cobbett: I learned that Ulysses S. Grant was a gifted horseman, whose horse riding ability led him not only to have greater life experiences, but also military experience. It’s one of the great advantages of heading into retirement is you get to spend time learning stuff that you’ve always wanted to learn.

Jon Cline: What what are you most excited about right now?

Tyler Cobbett: I’m on a quest to hike all of the trails in Santa Cruz Mountains here in California. I’m hiking at the rate of 15 to 20 miles a week right now. That’s so exciting, because one, it’s contributing to my fitness and health. But it’s also exposing me to the incredible beauty of this area, and paying it forward that those who envisioned and surveyed and built these trails gave us this incredible gift. It’s an amazing thought and it inspires me to see if I can pay it forward in some ways as well.

Jon Cline: Are you keeping track of that on a map as far as what you visited? Can you show that?

Tyler Cobbett: I don’t have it up, but basically if you envision Highway 9 heading sort of through San Jose, over to the coast, I’ve hiked all of the trails north of Highway 9, along Skyline, which is the spine of the Santa Cruz Mountains, up to almost highway 92. So it’s many many miles so far, probably north of 100.

Jon Cline: That’s wonderful. And so our final one here is are there any tools of the trail that you really love right now? Any kind of tool, whether that’s an app or device, something that’s really, really helping your life right now.

Tyler Cobbett: I can give you three quick ones. This headset. Poly, used to be known as Poly Con, now known as Poly, I just love. It’s so intelligent, Bluetooth, it lets me stream my audio while I’m working. But it also interrupts that streaming when a call comes in or when I place a call. It’s got a long battery life with really good bass response from the earphones and microphone. I love this headset. I love my cordless drill and my cordless saw. I can’t believe that these things have advanced so that I can run them for hours on a single battery charge. I love all trails. If you’re into hiking, if you haven’t decided on a good hiking app, All Trails, it’s pro version is extremely good for recording your hikes.

Jon Cline: Nice. The final one is what inspires you right now?

Tyler Cobbett: I think I’m inspired by the the emerging possibilities of AI. Just specifically in the software technology industry. I think it’s been getting introduced with more fanfare than necessarily substance, but there’s so much that can be done with AI. My personal pet peeve is is the travel industry. You know, why should I have to tell the app where I want to go? Why can’t I tell it my needs and have it tell me like a travel agent would what the facts are that fit into my timeframe and my budget. So I think what inspires me is the possibilities that in the next three to 10 years, AI is really going to become a reality, not only at a retail level but also in a business to business setting.

Jon Cline: Well, amazing Tyler. Thank you for sharing with us as you’ve come down off the mountain, and we look forward to seeing you on a trail sometime soon. Good luck on your goal of accomplishing all of the Santa Cruz Mountains and maybe you’ll have the JMT and the Pacific Coast Trail after that.

Tyler Cobbett: Thank you so much, Jon, for this opportunity. And Eric, it’s great meeting you and chatting with you.