Steve Klebe: Life, Leadership, and Lessons from the Payments Pioneer

Intro: Broadcasting live from the Business RadioX studios in Houston, Texas. It’s time for Houston Business Radio. Now, here’s your host.

Trisha Stetzel: Hello, Houston. Trisha Stetzel here bringing you another episode of Houston Business Radio. It is my pleasure to introduce you to my guest today, Steve Klebe, a payments industry veteran with over 35 years of experience shaping how the world moves money. Steve recently retired three years ago from full time work, but continues to serve on multiple private company and advisory boards. Most notably, he was the head of enterprise payments Performance at stripe, where he led key partnerships and represented the company in global payment associations. Before stripe, Steve served as head of GE business, developed for PSP partnerships at Google, helping grow the platform’s acceptance to over 150 payment service providers worldwide, supporting hundreds of thousands of merchants and millions of transactions. His career spans leadership roles at Verifone, Cybersource and Google, and he’s spoken at dozens of industry conferences about the future of payments fraud prevention and authentication. But beyond the professional milestones, Steve is passionate about giving back, enjoying life beyond the boardroom, and mentoring the next generation of leaders in tech and finance. Steve, welcome to the show.

Steve Klebe: Oh thank you Trisha. I’m really looking forward to the conversation.

Trisha Stetzel: I’m excited about having you. So tell us just a little bit more about who you are.

Steve Klebe: Ah, well, um, you know, I’d like to say that this whole journey was planned, but it wasn’t. Um. Uh. Oftentimes when I’m engaged with my younger colleagues throughout my career and they would look at my career path, um, they would presume that I had planned it all. Um, and I hated to break it to them that, you know, uh, most of it was fate and spontaneous, you know, combustion. Um, so really, um, uh, I, you know, was blessed, um, with, uh, being around a lot of really smart, hard working people. And, um, um, early on became passionate about, um, you know, being involved with products that, you know, actually had a, you know, pretty significant impact. Um, and so, um, I think, you know, in another life, I’ll probably come back as a product manager, um, rather than a sales and partnerships person. Um, because at core that’s, you know, that’s really, you know, what, uh, motivated me most of the most of the time of the journey. Um, but like, for example, I just came back from a trip to New York and, um, I got together with six of my former Google colleagues, and, you know, they’re all like, roughly mid 30s to late 40s, um, and just extraordinary people. And, uh, they’ve all, all but one have left Google. Um, and so, uh, but all through the years I’ve, I’ve had the pleasure of, um, uh, being approached not only to be a industry expert advisor, but to also just, you know, uh, be a career coach, you know, very unprofessionally trained, you know, career coach, um, and, and the like. And now in my role, um, with these various startup companies where I’m an advisor or a board member, um, you know that that’s also something that I really, you know, enjoy, you know, doing, um, blending the career experience and the domain experience with just meeting, you know, new, interesting people who are passionate about something, um, and having the opportunity to help them, you know, has been, you know, fantastic.

Trisha Stetzel: I love that. And we won’t tell your wife that there’s a third chapter to this life. Okay? I promise I won’t tell her.

Steve Klebe: Fair enough, I appreciate that.

Trisha Stetzel: Okay, so I know you mentioned that you didn’t have a plan, but I’m guessing that you made some decisions. Looking back, what was the most pivotal career decision that you made and what did it teach you about risk and timing.

Steve Klebe: Yeah. So I, I, um, the way I normally would answer that question is the first, you know, 20 years. Uh, first of all, I never planned to be in sales. Um, but it just so happened that the very first job I got out of college was in sales. And luckily, um, this was a very small company, but, um, you know, they had kind of co-opted a, uh, a sales training program and, um, you know, gave it to us. And they put us through a pretty extensive sales training program, which was unusual for such a small, you know, company. So I learned some extraordinary skills, um, that, uh, you come to learn later in life, serve you whether you’re in sales or not. Um, so I went from direct sales with that first company over five years to ending up running the sales team. Um, and, um, I did that at a couple of other companies subsequently. But then about midway through my career, I really decided that I was better at product related things and partnerships. Um, and uh, also, uh, didn’t want to manage people any longer. Uh, I realized that that was not my forte, um, that I was much better at, uh, interacting with clients and partners, um, and, um, um, and focusing on working with the product teams to actually, you know, either come up with new product ideas or enhance the products that we had.

Steve Klebe: So, like when Google, uh, reached out to me 15 years ago to recruit me, um, I made it very clear, um, that, you know, I did not want to manage people, uh, and they were okay with that. Um, but along the way, you know, my manager, you know, multiple times, you know, said to me, well, you know, you’re only going to go this far here if you’re going to refuse to manage people. Uh, he finally insisted that I manage one person for about two years. Um, which was easy because he was a friend and a colleague and totally competent, so I didn’t have to, you know, uh, you know, really manage him. It was just on paper only. Um, but, um, so that was an important career, you know, move. It was a conscious decision on my part to move out of direct sales and sales management into partnerships, and then, you know, not to want to manage people. And I was at a point in my career at that juncture where, you know, I could sort of, you know, I was willing to take the consequences, you know, of what that meant.

Steve Klebe: The other thing, I guess I would say is, um, you know, I worked for ten companies across 44 years, and most of them were early stage companies. I was the third employee, the 15th employee, the 35th employee, etc. when I got to Google, I was the 45,000th employee. Um, and I, you know, during the nine years I was there, the company grew to 145,000, you know, people. And the other realization, um, uh, was that I really preferred working, you know, for smaller companies. Not that the Google, you know, journey was not wildly successful. Both, you know, career wise and economically. Um, but, you know, uh, if I had my choice, you know, I’d much prefer to work for a company that had 50 to 1000 people, um, where everybody was focused on a single mission, um, you know, etc.. Uh, Again. Google wild thyme. You know, uh, met some great people that I’ve maintained friendships with. Um, but, you know, the bureaucracy and, you know, especially towards the end, like, getting anything done, you know, was nearly impossible.

Trisha Stetzel: Mhm. I could imagine in a company that size trying to get through the bureaucracy of just one thing. We just need to check one box and it’s really tough. How important was it during your career to build those relationships? I know you mentioned you were you weren’t the guy who wanted to manage people, but I know you’ve done a lot of mentoring and you just mentioned you’re still in touch with people that you’ve worked with. How important is it to keep those relationships?

Steve Klebe: Well, yeah, I mean, thank God for LinkedIn. Um, I have 7000 contacts on LinkedIn and I use it extensively. Um, and it has sort of become my address book. Um, you know, because when you leave companies, you have to leave all that stuff behind. But the beauty of LinkedIn is that you get to take it with you. And I’ve been very, you know, aggressive using it over the years. Um, and I coach people on using LinkedIn, you know, as, as well. Um, so, um, the way I would answer your question with two different, uh, threads, uh, one is that I decided early on that I wanted to go beyond the bubble of whatever company I was working for and get involved in industry, trade groups. Um, and the interesting thing about that, aside from just how powerful that can be, and I would strongly recommend young people get out of their bubble and get involved in their, in their industry. Um, usually when I asked whoever I was reporting to along the journey. You know, if it was okay to go to a trade association meeting, you know, etc., or to volunteer for a committee on, you know, at one of those organizations, they would normally say, uh, Steve, you know, great idea. But like we have to close the quarter out, you know, blah, blah, blah. So this is where I learned not to bother asking and just to go do it. And this is part of my philosophy, which is asking for forgiveness, not for permission. Um, and but those, um, participating in those industry associations was massively important to me and really ended up being important to the companies that I was working for. They didn’t appreciate it at the time, but that’s what led to a lot of speaking engagements, you know, where I was able.

Steve Klebe: And of course, when you’re introduced, it’s Steve Kleeb, you know, Working for, representing Cybersource representing fill in the blank. Um, and so that’s really important. So the other thing, um, was because I grew up in the payments industry during a pivotal time in the industry, and somehow or another, I got to understand at a level of, um, uh, detail that most people don’t get involved with, actually how the plumbing worked. And so and every company I was at, as we grew, we’d be hiring, you know, tens, hundreds of people. And more often than not, they came to these companies knowing nothing about payments. So I always volunteered, um, to do a class or two, um, you know, for new employees. It was never part of my job description, but I also always volunteered to do that. And that was like magic because, um, you know, these were new folks coming in with lots of new energy, wanting to get involved. And I came to become a, you know, like a really important resource, you know, for them. I love doing it. Um, you know, and, uh, so it was as much for me as it was for them. And so, uh, the outcome of that, um, you know, again, has led to lifelong relationships because people really appreciate when people go out of their way to do things that are not part of their job description, you know, to actually, you know, contribute, you know, more, you know, widely. Um, so those are the two things that pop to mind when you, you know, when you asked that question.

Speaker4: Okay.

Trisha Stetzel: So I want to take it just a little bit further, as you think back to three years ago when you decided to retire, and maybe even before that, as you were stepping out of these operational roles or these leadership roles and moving into more advisory roles or being on a board or volunteering, how how did that really bring your retirement to where it is now?

Steve Klebe: Yeah, that’s a great question. Um, so first of all, I, I was on, um, a variety of advisory boards for these industry trade groups throughout my career. So again, I didn’t just attend conferences. I would put my hand up and volunteer to be on committees and things. And, um, you know, several organizations, um, where I became a member of the advisory board, um, you know, that really, um, you know, also led to some independent advisory board, you know, opportunities. So half a dozen companies, even while I was working, you know, I was, you know, sporadically on advisory boards. And again, you know, because they were all early stage companies, you know, it’s not like we had an official board meeting every, you know, every 12 weeks or whatever. It was usually very spontaneous and, and the like. But it was, it was having done that, having done all this coaching, um, having done some, you know, spot angel investing over the years. Um, it was the combination of all of those things, um, that gave me the comfort that, um, you know, when I retired, um, you know, I was, you know, going to be able to continue to contribute, continue to be mentally stimulated, um, you know, and, um, you know, it just it has been actually when I was at this lunch last week in New York.

Steve Klebe: Um, you know, I was sharing with my, these former colleagues that it’s all been very organic. Um, you know, a lot of people, uh, as you approach retirement, um, you know, you hear all sorts of stories about people falling off the deep end and, you know, not knowing what to do with themselves, you know, etc.. Um, and that, you know, has not been an issue. It’s all been very like, sort of just organic and natural, you know. Et cetera. I do expect the other thing that I do quite a bit of, there are these things called expert networks. Um, there’s companies such as Guidepoint G. Um, alpha sites, and there’s about six of them. And, um, I’m registered with all of them. And I do these spontaneous one hour phone consults with mostly investment bankers who are studying a particular domain, and they want to talk to people who have had operating experience. Um, I had done some of those back in the day, but then when I joined Google, they had a policy that you couldn’t do them. Um, so then when I left Google, I was able to start doing them again.

Steve Klebe: And since I’ve retired, like last year, I did 40 of those calls. Um, and, um, they’re really fun. There’s no prep. It’s an hour. They just grill you with questions, and they’re just so desperate to talk to people who actually, like, lived in the trenches and did real work. Um, and so, again, it’s that combination of all of those things between all of those things and playing tennis and pickleball and a few trips here and there, you know, and walking my dog. Um, you know, that, uh, you know, and reading, you know, the one thing I would say that you didn’t ask about is, Um, you know, I love mystery novels. Um, and, um, you know, over my business career, you know, I was mostly compelled to spend most of my time. Not that I didn’t enjoy it, but, you know, reading trade journals and, you know, going to conferences and all that, you know, doing work, work. Um, but now that I’m retired, you know, I got my equivalent of a Kindle with me all the time. And, you know, anytime I don’t have a meeting scheduled or I’m not playing tennis, um, I’m reading a, you know, just a simple, mindless, you know, um, mystery novel.

Trisha Stetzel: Oh. Very interesting. Okay, so before we move into something, I want to take a deeper dive in. I know folks are already ready to connect with you. They’re very interested in knowing more. What is the best way for folks to connect with you, Steve?

Steve Klebe: I think the most efficient way is for people to just attempt to connect with me over LinkedIn. And, um, you know, my profile is readily available. There’s no other Steve Klebe on LinkedIn. Um, so, you know, you can share my LinkedIn profile, you know, uh, URL, um, out. Um, and this gives me a chance to decide whether or not there’s actually a reason to connect. Um, so that, yeah, that would probably work out the best. And like I said, I’m very active on LinkedIn. And, you know, I lean towards accepting outreach when, you know, when I think there’s going to be any meaningful, you know, connection. Um, so, yeah, that would be the best.

Trisha Stetzel: Okay. Fantastic. Yeah. Steve accepted my request. So I feel important right now. By the way, uh, Steve’s last name is spelled k l e b e if you’re looking for him on LinkedIn. And of course, the link for that will be in the show notes, and you guys can just point and click if you happen to be sitting at your computer. You said something I’d like to dig into just a little bit further. Earlier you said ask for forgiveness, not permission, and you gave one example of that. How has that mindset shaped your success overall?

Steve Klebe: Yeah, so not just in the context of, um, that one example I gave you. The other context is, um, just the, um, uh, various some of the most significant initiatives that I worked on in my career, um, took longer than people around me thought they should, but I, you know, felt, you know, really passionate enough about these things. So, um, I would just basically like, you know, just keep going. Whether they knew I was continuing to pursue these things or not. Um, and, um, again, the probably the most profound, you know, achievements that I made in my career, um, you know, uh, came as a result of, you know, just sort of, you know, not listening to the advice that I was getting or the demands I was getting from leadership above me, uh, and, um, and continued to pursue, you know, uh, several of these initiatives. Um, now, I always add an asterisk, though, when I share that expression with people, there’s a responsibility that goes along, you know, that is not just like dumb luck. And it’s not just, um, you know, bravado. Um, it is actually, it requires you to have, um, a, uh, deep belief after doing like real thought and work and research, to decide which of those things are worthy of continuing to pursue without asking for permission. And if you do it right, you never have to ask for forgiveness. Matter of fact, the people who were trying to tell you not to do these things should be asking you for forgiveness because they made a fuss and and didn’t want me to continue pursuing, you know, these, these opportunities.

Steve Klebe: Um, and I could give you specific examples, but, you know, just to, uh, suffice to say, the most profound things I accomplished in my career almost always involved, you know, just not abiding by, you know, the, uh, the doctrine of the moment and, uh, you know, keeping these things alive to through to conclusion and success, even when there were a lot of pessimists, pessimists around me, um, you know, who would say, like, oh, but, Steve, you know, we have to close the quarter. Well, I would close the quarter, you know, I mean, I’d get my job done. I always got my day job. And that was like, for example, at Google, you know, my day job I could do practically in my sleep. And so I spent my energy working on things that, you know, really inspired me, rather than the, you know, the mundane things that, you know, were part of just getting partnerships done. I could, you know, I could do those things in my sleep. Uh, I knew how to do them. I knew the mechanics of keeping the momentum on those things going. And I didn’t have, you know, that was not where I was going to really, you know, get energized by doing those things.

Trisha Stetzel: Yeah, absolutely. I’ve heard some really important things today around building relationships, building community or having community, giving back, taking calculated risks. How do you find the difference between being in big business? I heard you say that you’re working with some startups or on advisory boards and being there. How what would you say to those younger businesses, the people who are in leadership there about the importance of finding ways to build relationships and community and giving back and taking calculated risks?

Steve Klebe: Yeah. Well, this goes back to a comment that I made earlier about LinkedIn. Um, you know, the way I used to use LinkedIn and still do to this day is if I have a meeting scheduled, no matter how that meeting came about. But presuming it’s somebody I’m meeting for the first time, the first thing I do is go to LinkedIn And, you know, look at their background and look for things that are going to be fun and interesting to talk about. Um, and, uh, it doesn’t really matter what it is. I can, you know, an example would be I’ll notice that somebody went to Penn State University. Um, I didn’t go to Penn State, but my sister has taught there for 35 years. Um, and it was like, you know, what a great conversation starter. Um, and, you know, I don’t think there’s anything wrong with that. Matter of fact, I think it’s just the opposite. I think it’s like people really appreciate that you take the time that you notice, you know, etc.. Um, and so, um, you know, the advice that I, that I do give to some of these early stage companies in this regard, um, and some of the founders need more advice in this front than others. Um, but you know, what I normally, you know, would say is, um, to be sincere, um, use LinkedIn like I use it so that you can you have something meaningful to converse with people about.

Steve Klebe: Um, same sorts of things. Get out of your bubble, you know, um, you know, and, you know, some other really basic things which maybe go back to my early sales training, which is, um, you know, just if you promise somebody something, um, you know, jot it down on a piece of paper and make sure you actually deliver on it. Don’t you know there are. So it’s really sad, but true. I think in the business world, um, I’ve come in contact with tens of thousands of people, and I would say that there’s less than 5% who you actually come to respect because they are diligent, timely, responsive, you know, Etc.. Uh, and I think a lot, a lot more people could be a lot more successful, um, if they just were able to do some of those simple things. And back in the day before everything got computerized, you know, I would have three by five note cards. Um, and I would, you know, make a clear list of things that I had promised to prospects and things. And, um, now, you know, there’s lots of tools that you can use, you know, put it on your calendar. Um, you know, there’s an application that Google provides that works across all platforms called keep k P. And it’s like a, it’s a virtual, searchable, uh, post-it note, you know, and we all know the in the old days, post-it notes at one point were magical.

Steve Klebe: But then you come to realize, you know, you walk into somebody’s office and they have 15 post-it notes, you know, staple, you know, paste it on to the outside of their monitor and they can’t remember, you know, can’t figure out which one. And, you know, the cleaning people come in and one falls off, you know, etc.. But now that it’s all, you know, it’s searchable, you know, I mean, it’s just a magic tool. It’s free. I mean, why wouldn’t you use it, right? Yeah. Um, so those are the kinds of things. Um, so again, it varies, you know, dramatically. And that’s what’s good for me because, um, you know, uh, while most of the companies I’m advising either are in payments or they’re peripherally involved in payments, of course, of course I can help them with that. Um, but it’s the other stuff. Um, it’s the more nuanced stuff that, you know, I’m able to help them with, um, around things like get out of your bubble, get, go, go to the trade shows, don’t just attend a conference, get involved, you know, etc. because then people like really come to appreciate that you’re more than just a talking head. You know that you actually, you know, can can contribute above and beyond.

Trisha Stetzel: Yeah, absolutely. Such great advice today. I’ve really enjoyed our conversation, Steve. I have one last question for you as we wrap up. What’s next for Steve Klebe?

Steve Klebe: Well, um, it’s, you know, again, another great question, uh, which is something I learned, by the way, in sales training. Uh, welcome, welcome questions. Welcome objections. Um, yeah, I would say, you know, I’ve expected, uh, now that it’s three years since I’m not no longer operating. Um, I would I had started to expect that, like, this year, like, these expert network call requests would, like, drop off a cliff. Um, but it hasn’t happened, which is somewhat surprising. Um, and so I’ll keep doing those for as long as that lasts. Um, but, uh, you know, for as long as I’m physically able to both keep, you know, my hand out there in the business world, and there doesn’t seem to be any letup in that. I mean, there is. I met with another founder yesterday who wants me to join, you know, his advisory board. Um, and, uh, it’s, it’s more general fintech and, um, and investing rather than, uh, specifically payments. So, um, I’d like sort of continuing to broaden, um, you know, the scope. Um, but really, as long as my body will allow me to play tennis four times a week and play pickleball once or twice a week, and, um, I’m able to travel, you know, wherever I want to go. Um, and, um, uh, so other than that, it’s it’s pretty, you know, it’s pretty much the same.

Steve Klebe: Um, but I know that it doesn’t last forever. Um, so probably like to do a little bit more, you know, traveling, um, you know, over the next couple of years, um, I did a lot of international travel during, uh, for business. Um, but I haven’t done that much for personal, so I would try to take a day, an extra day when I was in Singapore or Copenhagen or Amsterdam, uh, or London, you know, to go see a couple of things. Um, but. Oh, I did take an Alaska cruise, um, this past, um, summer with my two grown children, um, and had a great time. So that kind of stimulated some, you know, thoughts in my head about what comes next. Um, but anyway, for the, for the, for right now, it’s stay healthy, stay active. Continue, you know, enjoying the time with all these, you know, various founders and things. Hopefully have some of my angel investments pay off. Um, because that’s one thing you learn when you’re doing angel investing is it’s like a 5 to 10 year journey. Um, you know, these things are not quick fixes or quick hits. Um, but yeah, just keep meeting different people, stay active, uh, etc..

Trisha Stetzel: Yeah, I love that. Building relationships and community, making sure that we’re still taking some calculated risks even when it comes to travel. Right? Uh, so it all applies here. Uh, and then, of course, giving back what you do so much of. Steve, thank you so much for this amazing conversation. You’re doing such amazing work, post work, and I appreciate you coming on and talking about it with me today.

Steve Klebe: It’s my pleasure. Trisha, it’s been wonderful to meet you. And, um, you know, Feel free to reach out anytime.

Trisha Stetzel: Great. Thank you so much. And you guys, just a reminder, if you’d like to connect with Steve, please reach out on LinkedIn. His last name is spelled k l e b e, and I will put that in the show notes as well. So you can just point and click if you happen to be sitting at your computer. All right guys, that’s all the time we have for today. If you found value in this conversation that Steve and I had, please share it with a fellow entrepreneur, a veteran or Houston leader ready to grow and of course, follow, rate and review the show. It helps us reach more bold business minds just like yours. Your business, your leadership and your legacy are built one intentional step at a time. So stay inspired, stay focused, and keep building the business and the life you deserve.