Bernie Borges [00:00:00]:
What if the fastest way to succeed was to stop trying to be the most valuable person in the room? Sounds counterintuitive, right? Well, in the mid-1990s at Oracle, well-known tech giant, the rule was simple: perform or you were gone. Russ Reader learned to win in that world, but not the way that most people did. He learned to figure out what the people around him needed to feel successful. Then he built toward that deal after deal and company after company. 30 years and 9 private equity-backed companies later, that instinct has been the through line of Russ’s career and revealed something that most leaders miss. Caring about someone else’s success has a way of becoming your own. The most valuable people in any organization are rarely the ones who make themselves indispensable. They’re the ones who make everyone around them better.
Bernie Borges [00:01:02]:
This conversation is about what happens when talented people choose to share instead of hoard, and about a legacy that’s built on making other people successful and in turn being made successful. We’re going to discuss why living to work beats chasing a mythical work-life balance Why making other people successful turned out to be the most reliable way that Russ built his own success. And how one question, what does this person need to feel successful, closed one of the largest deals in Oracle’s history. And why an organization’s most talented person can also be its most dangerous. My guest today is Russ Reader. Russ, welcome to the Life Fulfilled Podcast.
Russ Reeder [00:01:53]:
Thanks, Bernie. Great to be here.
Bernie Borges [00:02:03]:
Russ, let me give you an introduction to my listener. You are a C-suite operator, an advisor, a speaker, and an author. And for over 30 years, you have run, scaled, or rebuilt 9 private equity-backed technology companies across 6 continents, including Oracle, GoDaddy, and OVHcloud. You founded RightsLine, which was later acquired. And today you run KeyDelta, your advisory firm, and you’ve built 2 frameworks that guide how you lead. And at the time of this recording, you are writing a book called Heroes Don’t Scale, Scheduled to come out later this year. Can’t wait for that. And Russ, in this conversation, let’s go beyond your impressive resume and business practices.
Bernie Borges [00:02:52]:
Let’s explore the power of self-awareness in your success, Russ, and how it’s always been tied to how many other people you’ve helped succeed. Now, I know that you have a philosophy in life, and that philosophy is living to work, not working to live. So let’s begin our conversation there.
Russ Reeder [00:03:15]:
Thanks, Bernie. Yeah, I mean, I think growing up as an athlete underneath some great leaders in my family, especially my grandfather, we talked about leadership at the dinner table. I thought that was normal. And when I finally got into the workforce, they don’t tell you how to be successful other than accomplish the task at hand. And really, when I first got into management, I was lucky enough to be promoted at Oracle by the president, Ray Lane, personally. And when I was figuring out like, how am I gonna do this massive job? Here I am in Silicon Valley, in Redwood City, running a large division on the application sales side, and I just started helping my team be successful and really not knowing anything about servant-based leadership. I hadn’t read all the management books yet. I had read some, but learned a lot in college, but never the servant-based type leadership skills.
Russ Reeder [00:04:28]:
And I just kind of felt my way down the road of how to make my team successful, especially in Oracle, when people were trying to win by making other people not successful. And I think it was just that contradiction probably even helped me more.
Bernie Borges [00:04:46]:
Yeah, I remember actually in the ’90s, I knew some people that were at Oracle and that culture was really well known. Russ, you told me that you had an encounter once with an HBO co-founder that really had an impact on you. Can you share that story?
Russ Reeder [00:05:04]:
You bet.
Bernie Borges [00:05:05]:
Yeah.
Russ Reeder [00:05:05]:
So probably about 15 years ago, kind of mid in my career when I was trying to be all things to all people, we had this great CEO dinner. So there was just a handful, maybe 20 CEOs with one of the co-founders of HBO. And he told this amazing story. It was very emotional to me to hear him talk about The challenges, obviously, of starting HBO, which is wildly successful. That was very interesting. But more than anything, when he talked about his personal journey, and like so many of us were hard charging and go to the office and everything about work, but he found out the hard way that he was not giving back to his family how he needed to. And one day, and he got a call from his wife and his son had killed himself. And driving home that night, he pulled over and started crying.
Russ Reeder [00:06:14]:
And he— it really hit him like a brick in the face that he was doing things all wrong. And he was trying to be 3 different people. He was who he was at work. He was who he was with his family, and he was who he was without anyone else around. And he realized that by trying to please everyone, he pleased no one and not even himself. And, and so at that point on, he really tried to focus on being the same person with everyone in every environment. And then he could put that energy into HBO and he had a, you know, he’s had a very successful career and happy life.
Bernie Borges [00:07:12]:
That’s a very impactful story. I can certainly see how that can just impact everybody in the room in that moment. And and really have a meaningful and lasting impact. So, thank you for sharing that story, as tragic as it is hearing, but it’s a good reminder. So, thanks for that, Russ. Now, part of your backstory is you led, I believe, 9 companies in the C-suite. And you mentioned that sometimes, maybe often, you would come in replacing a leader That maybe you were the 5th or the 6th leader in that company. What was your approach each time you kind of parachuted into one of these companies? What was your approach to leading those companies? Most AI initiatives don’t fail because of the technology.
Bernie Borges [00:08:00]:
They fail because leaders don’t plan the human side. There’s a fear tax and a meaning gap that’s draining your team’s performance right now, and most leaders Don’t even know it. Our Human Dividend assessment measures both across 4 dimensions: reducing fear, creating clarity, preserving meaning, and building adaptability. It’s a structured diagnostic that you take online, alone or with your team. It includes a debrief call, a custom report that’s built around your team, and specific next actions that turn insight into ROI. for your business and your people. To learn more about the Human Dividend Assessment, visit the link in the show notes.
Russ Reeder [00:08:49]:
Well, I first want to say that I didn’t start out looking to go run multiple companies. That wasn’t my goal. But after I sold my company in 2006, which helps run a lot of the media companies, Netflix and HBO and many of the others right now, that I said, okay, what am I going to do with my career? And this was in 2006. And so I said, I don’t want to go back to Oracle. I’ve already checked that box and I don’t need another title. And I started calling friends of mine that I had met that when I was raising money for my company and And I started to get a lot of calls back saying, hey, Russ, can you come help this company? Well, I learned pretty quickly, Bernie, that you don’t get a call, at least I don’t get the call that went, hey, Russ, I’ve got this amazing company. It’s going through the roof and we need you to come ride the—
Bernie Borges [00:09:55]:
Ride the wave.
Russ Reeder [00:09:56]:
Ride the rocket here. I didn’t get it, but they were really good companies with good bones that they needed a reset. And there’s a lot of those calls that you get. And for me, I had to figure out which ones to say yes to. I said no to many more than I said yes to. And coming in, I’ve learned of those 9 different companies, I’ve learned something different about management and about people, about customers, and about myself every time. And I think the more I learned through every experience, the more I think the more generous I became with my time and my understanding to people. Like I used to come in thinking that everyone in the exec staff thought like I thought and was looking in the same direction, and the communication broke down.
Russ Reeder [00:10:58]:
And so really understanding, trying to meet those teams, all of the employees where they were, right? You get a new CEO, it’s not like you’re happy about that. And maybe some employees were happy about it in some situations, but they’re nervous nonetheless. And so Really coming in and learning how to have a reset and listen and not scare, but make sure everyone’s aligned on the mission, vision, and values that are the most important thing, and that everyone understand what success means in that role. No matter what you do in life, you want to understand where you’re going, what are the rules of the road, kind of those guardrails, values, And you want to understand what success means. You don’t want to just be working when you don’t know if you’re failing or succeeding.
Bernie Borges [00:11:55]:
Yeah. Now, running those 9 companies, that was after your experience at Oracle, right? Right.
Russ Reeder [00:12:01]:
After Oracle and then after I sold my company, correct.
Bernie Borges [00:12:05]:
Okay. Wasn’t there, if my notes are accurate, Russ, wasn’t there an experience at Oracle that really impacted sort of your approach to how to get things done. I wrote it down in my notes as your $25 million lesson. Does that jog a memory for you?
Russ Reeder [00:12:25]:
Okay. Well, it was a big deal then. I don’t know if those are the biggest deals anymore, but yeah, so I helped close a $25 million applications deal to make Oracle a standard in a company, one of our customers. And But I kind of fell into this, and this was before I was even promoted. I was a young sales executive with multi-billion-dollar accounts. And instead of kind of running through walls and calling people up and telling them what I needed them to do, I was just a sales rep. I couldn’t tell anyone what I needed them to do. This was in 1996, and We had this amazing tool.
Russ Reeder [00:13:09]:
It seems pretty silly to think it’s amazing now, but we did then, and it was the internet web browser, and our HR applications were tied to it, and I could put in anyone’s name and see their org directly up to Larry Ellison. And so if I looked at a deal with a customer, whether it was US Postal Service or Bechtel or Creative Labs or one of these global companies we were trying to close a deal at, I could figure out, okay, we needed some feedback on this feature in the database or this feature or future roadmap for the application, or we needed marketing to step up and do something here. It took a team to close these very large deals.
Bernie Borges [00:14:00]:
Sure.
Russ Reeder [00:14:00]:
And so I would, the person that I knew that normally I would’ve reached out to, I would use the org chart tool and I’d go up like 3 or 4 levels and I would contact them. And first I’d do research to figure out what their role was and what success looked like for them. And then I would pitch what I was trying to do as how it aligned with what they needed to do to be successful. And just, I didn’t read it in a book. It just kind of worked out that it worked when I started going up higher, because when I went lower, I think it was just the culture since it was so cutthroat, people were afraid to make mistakes.
Bernie Borges [00:14:50]:
Sure, sure.
Russ Reeder [00:14:51]:
And so that culture, was not good. You don’t want a culture where everyone’s afraid and stepping on each other.
Bernie Borges [00:15:00]:
Right.
Russ Reeder [00:15:01]:
And so by actually reaching out there and talking about how this would make other team members successful, actually that’s how I got the promotion, that people noticed and it was a new way of selling solutions. I started selling business value to business people with a team behind me versus an individual contributor selling features and functions and row-level locking to engineers.
Bernie Borges [00:15:30]:
Sounds like maybe, Russ, you learned as much about dealing with other people than as you did about closing a large enterprise team sale at a tech giant like Oracle. So, congratulations on that. And you’re probably right. Today, $25 million is not the biggest deal out there, but at that time, I’m sure that was a very— well, you said it was the largest deal at the time at Oracle.
Russ Reeder [00:15:54]:
Yeah, largest application sale. It was fun. Yeah, yeah.
Bernie Borges [00:15:58]:
Let’s shift gears a little bit because a lot of what you’re really discussing here inherently is about your own self-awareness and how it was evolving throughout your career. And as you know, there’s a recent study from Harvard that says that only 15% of people are self-aware, which was mind-blowing when I saw that. Although some people, when I share that, they go, it’s that many? It’s that high? But I want to talk about how that impacts you. Like, what is your own— I know this is going to sound strange— what’s your own self-awareness around self-awareness in your own success?
Russ Reeder [00:16:38]:
Well, the reason why probably it’s so high is because they’re not aware enough. to know that they’re not aware. So they say they are aware, you would think. But for me, I think it comes down to, like, when I was younger, I always thought leaving a legacy was going to have a big name, right? I wanted everyone to know my name, or I wanted a lot of money. And then something turned kind of mid in my career where I wanted to help others be successful. And back in 2012, I started writing a blog. It’s when I really started writing, not to get my voice out there and be someone that people knew. I really started my first blog back in 2012 So if things didn’t work out and I got hit by a bus, my kids would know what I cared about.
Russ Reeder [00:17:41]:
And that’s one of the reasons why I’m writing a book. And it’s how do I take my knowledge? Because I’ve done a lot of things right and I’ve probably done more things wrong. I mean, it is, and I’ve learned every step of the way, but the one thing that I’ve always seen pay back Is that looking out for others and being that good leader. Like, I think that there’s good leaders do win, right? And there’s so many examples. I won’t name any right now that, and some aren’t even on this planet anymore. And so they were just jerks to be around, but they made multi-billion-dollar, trillion-dollar successful companies. But people only worked for them because they then had more money than they could ever think of. And for me, it was always about how do we create something bigger than us and all do it together?
Bernie Borges [00:18:44]:
So you mentioned that you started your blog in 2012 and now you’re writing a book. So clearly writing is something that is a passion of yours. Let’s talk about your book. And I want to begin with the question around the title, Heroes Don’t Scale. What’s behind that?
Russ Reeder [00:19:06]:
Well, like I said, I grew up spending a lot of time with my grandfather, Colonel Red Reeder, at West Point. And he was one of the main officers that helped plan D-Day. He led the 2nd Infantry Division on Utah Beach, about 3,000 men. And on the 7th day, he lost his left leg. Then came after, uh, uh, uh, one year in Walter Reed Hospital, he then went back to West Point and he started writing books. And so my parents got divorced when I was very young. My dad didn’t have much money. And so my sister and I, my, spent a lot of time at my grandparents’ house.
Russ Reeder [00:19:47]:
My dad would come pick us up every weekend and— Bring us to West Point and spend time with my grandparents. And I didn’t even know the lessons that I was learning. And he always talked about the leadership and the war history and his friends like General Eisenhower, President Eisenhower, and General Marshall and Red Blake, Vince Lombardi. I was young. I didn’t know.
Bernie Borges [00:20:16]:
Yeah.
Russ Reeder [00:20:16]:
who these people were then. And as I grew up, I started reading all of his books. And my grandfather told me, you should read autobiographies if they tell the truth, you’re going to learn something. And so I started, I’d read just so much and I haven’t stopped that. And most of the things I read now is I consume via Audible when I’m doing other things. But So for me, it was, I was consuming all of this information. I wanted to start to give back. And so the book Heroes Don’t Scale, when I first said, okay, now I am going to write a book, I, with 30 years of experience, where do you start? Like, I didn’t want it to be an autobiography.
Russ Reeder [00:21:03]:
I wanted to give back. I wanted for people to, at all levels, not founders, not just CEOs or executives, but anyone in any company, could figure out how to be better. And the one learning, like I said earlier, mission, vision, values is very important. There’s a lot of books out there about mission, vision, values. And if you’re lower in the organization, you really can’t affect that. I wanted to have a broader kind of substance. And we all know that people are the biggest asset of any company. But some of them are the biggest liability of some companies as well.
Russ Reeder [00:21:45]:
It’s very hard to deal with. And so time and time again, I would come into a company that couldn’t break through. Something was happening, whether it was in engineering or whether it was in sales or whether it was executive staff. And I saw the pattern repeat itself is that these people were hoarding information and hoarding power. And dealing out information like currency. And you’ve always heard, we all know those people. It’s like, oh, you can’t fire that person. They’re indispensable.
Russ Reeder [00:22:19]:
Or they know every line of code, or they have the relationship with our customers. And then they always usually follow up with that of, and we can’t fire them because they know our customers. And, but what happens is, It stops everyone else around them from growing. And so every company has those people that are trying to hoard information at every level. They’re trying to build a moat around them when it’s really a self-fulfilling prophecy. At the end, those people just don’t survive. And so that’s where I wanted to go through and write a book where people can see How do we identify systems that can help the company scale around or help move out the people that are very successful and maybe some are respected, but have really made it all about themselves versus making it about others’ success?
Bernie Borges [00:23:25]:
So sort of busting the myth that certain people are indispensable. That’s kind of what my takeaway.
Russ Reeder [00:23:33]:
Yeah. I mean, I’ve even read articles recently of make yourself indispensable. Now that AI is here, you have to make sure that it can’t take your job. But I just wrote an article earlier this year about Messi, right? So here’s Messi, World Cup, unfortunately they lost, but Spain did a great job. And But Messi, the all-time leader in scoring, when you look at it, he’s also the leader in passing assists. So, that is the type of leadership that really makes a difference. He is the best in the game because he passes the most.
Bernie Borges [00:24:17]:
Mm-hmm.
Russ Reeder [00:24:18]:
And he scores the most, right? So, you just, We wouldn’t know Messi’s name if all he did was if they gave him the ball, he scored, because his team wouldn’t have won. He’d be a good scorer, but he’s made the team rise up to 2nd place in the World Cup. And those are the type of experiences where I think more management, these are hard decisions. And I think that what I wanted to write about this so people could Help teach them. Like I used to be a hero, right? I mean, and sometimes I probably do try to do more than I should. And when I was running RightsLine, and I remember the day when I was sitting there on a Saturday and beautiful Saturday afternoon and running the sales deals and versus having my sales team do it. I was CEO and founder and I was in the weeds. And I wasn’t really making a difference, but I thought that I was.
Russ Reeder [00:25:21]:
And so the company, once I was able to step out of the way, the salespeople and our CRO, our chief revenue officer, was able to rise to the occasion. So I didn’t discover this without kind of being the person in the room as well.
Bernie Borges [00:25:41]:
Gotcha. So as I listen to your story, Russ, what I’m hearing from you is that there’s 2 of my 5 pillars that are really big for you, and maybe more than that, but this is, you know, my immediate takeaway. So my 5 life pillars are health, fitness, career, relationships, and legacy. And what I’m hearing in these conversations we’ve had is that a lot of your fulfillment has come through your career around your relationships and how you’ve helped other people succeed, which is helped you become very successful. But the other thing that I’m hearing, Russ, and I really want your response to this, is legacy. Legacy is not just about how do you want to be remembered somewhere down the road after you’re gone. And gone doesn’t have to mean that you’re dead. I mean, it could just mean you can be gone from a company, that kind of thing.
Bernie Borges [00:26:29]:
But legacy is also about impact, the impact that you can have today. And I’m hearing that that’s a big part of your fulfillment as well.
Russ Reeder [00:26:37]:
Yeah.
Bernie Borges [00:26:37]:
Comment on that?
Russ Reeder [00:26:39]:
Yes. And you’re totally right. And what I have learned is it’s not about making impact so everyone knew I made an impact. It’s actually making real impact, period. And it means more when you don’t have to go tell everyone about it and post it on LinkedIn and Facebook of like, look at my impact. It’s actually more meaningful when you’re making a difference and making a great significant impact, and then you keep doing it. That’s the most impactful, I think, for me as a person, but it takes confidence. It takes confidence that You’re making a difference.
Russ Reeder [00:27:31]:
No one has to tell me I’m making a difference. I know I’m making a difference. I don’t need this attribution from strangers and others. And I know I’m doing the best I can. And that’s how I’ve been able to be fulfilled.
Bernie Borges [00:27:50]:
Well, that was actually, that was going to be the exclamation point that I was going to put on it, your very last comment. And that is that when you experienced that, You do experience that tremendous sense of fulfillment. And the one thing that I say about fulfillment, Russ, is that fulfillment is almost always immutable. So when we experience fulfillment, there’s nothing that can take that away. And to your point, you don’t have to be bragging about it and let other people know about your impact. It’s the impact that you have that gives you that fulfillment that’s so immutable. That’s enough. Love that point.
Bernie Borges [00:28:27]:
Russ, this is a great conversation. I can’t wait for your book to come out. Can I put you on the spot? Do you know when it’s coming out or you’re not sure?
Russ Reeder [00:28:34]:
Yeah, hopefully by the end of this year. We’re working on it now, working on it with the publisher. And I have so many stories. It’s the hardest part is being able to figure out which ones do I lead with and which ones do I save for later.
Bernie Borges [00:28:48]:
Right, right, right. Stories, that’s what it’s about, the stories. Well, before we wrap here, let me invite you to share with my listener, where can people connect with you and just learn more about what you’ve got going on?
Russ Reeder [00:29:01]:
Yeah, thank you. You can always go to LinkedIn to find me. You can go to keydelta.com, the company that I founded and run with a group of great operators and AI executives. And you can always go to russreader.com as well.
Bernie Borges [00:29:17]:
Fantastic. Well, Russ, my listener knows that those will be linked up in the show notes for this episode. And Russ, I just want to thank you for joining me for this amazing conversation here on this episode of the Life of Phil Podcast. Love what you’re doing. Can’t wait for your book to come out. And in advance, I’ll just congratulate you on the success that I know that book is going to have. So thank you so much again for joining me today, Russ.
Russ Reeder [00:29:41]:
Thanks for having me here, Bernie.
