The Real F Word Podcast: Ep 9 with Kortney Osborne

Kortney Osborne: [0:00 - 0:10] I don't really think that the real F word is failure. I think that the real F word is fear. What were you fearing? And what would I go back and not fear? 

Voiceover: [0:11] Welcome to The Real F Word. 

Joe Grover: [0:18] Well, today is pretty fantastic, right? Because Kortney and I run the marketing division, the fractional marketing practice, at Amplēo. Kortney's my partner. 

Kortney Osborne: [0:30 - 0:31] Heck yes, we do. 

Joe Grover: [0:31 - 0:35] And in fact, when I first launched the podcast, I invited you to be cohost, 

Kortney Osborne: [0:36] And I declined. 

Joe Grover: [0:37 - 0:43] So this is your audition, and if you do well, season two, Kortney and I might be doing this together. Kortney is—

Kortney Osborne: [0:43 - 0:48] You know I don't leave my house. This is a big deal for me to leave my house. So for me to have to cohost, I would have to leave my house more. 

Joe Grover: [0:48 - 0:53] I know, but you're funny. So, first of all, let's talk about your comedy. 

Kortney Osborne: [0:53 - 0:54] Okay. Okay. 

Joe Grover: [0:55 - 0:56] Because you've done some standup comedy. 

Kortney Osborne: [0:56 - 1:00] I have done standup comedy. And that is a lesson in failure. 

Joe Grover: [1:00 - 1:03] Is it? No, no. You were successful, right? People laughed.

Kortney Osborne: [1:04 - 1:31] But, you know, in terms of this podcast, comedy is the ultimate “constraints are the path,” because you get up night after night after night, and you iterate, and you fail, and you see what was funny and landed and made a laugh, and then you build on it versus what you thought was so funny and just crickets, you know? So I have done standup comedy. 

Joe Grover: [1:31 - 1:48] I'm reading a book right now, and it talks a lot about comedians: That Jerry Seinfeld, he would stand up in front of a small audience to pressure test all of his jokes. And if people laughed, he'd go back and jot down a few notes and improve it. And if it was crickets? Never made it to the final script. 

Kortney Osborne: [1:48 - 2:16] And it's hard when comedians break through. It's hard for them because that first Netflix special that they had was 10 years of material and failure. And then, all of a sudden, they make it, and they've got a year to turn around another special. And that's hard. But it took—I think he has one: One time I watched this thing, and I think it was his PopTart bit. Took him 10 years to write. 

Joe Grover: [2:16 - 2:18] 10 years. He just kept trying it on?

Kortney Osborne: [2:18 - 2:19] Just kept trying. 

Joe Grover: [2:19 - 2:40] And you're like, “Not funny. Boo.” He's like—that's amazing. But what you're really known for is you're a really proficient market marketer/marketing leader with tons of experience. You spend a ton of time at the most successful tech company here in the state of Utah. Maybe ever. Probably ever. Right? Eight-billion-dollar exit. You were seven years at Qualtrics?

Kortney Osborne: [2:40 - 2:40] Eight and a half. 

Joe Grover: [2:41 - 2:42] Eight and a half years at Qualtrics. 

Kortney Osborne: [2:42 - 2:47] I was one of the first people on the marketing team and then helped grow that to that first exit.

Joe Grover: [2:47 - 2:56] There was a lot of learning over eight and a half years. You saw a ton of transition, a ton of growth. There had to have been failures along the way. 

Kortney Osborne: [2:57 - 2:57] Yes. 

Joe Grover: [2:57 - 3:05] What's a moment that you'll never forget where maybe there was a swing and a miss on a campaign or a new marketing strategy? 

Kortney Osborne: [3:05 - 4:05] You know, when I think of failure, I think the definition of failure or what your definition is, my failure usually isn't swings and misses in regards to marketing campaigns or money lost or anything like that. Most of the time, my initial—you just asked that question, and my initial thought was that time I yelled at that person. My failures, usually we can look at the context of the business or on a personal level, is the times I didn't treat people right. And those are the ones that stick with me. Because you can look at the success, and we can talk about programs specifically, but when you ask that, that was the first thing that popped into mind is that time I yelled at someone. That time I didn't advocate for someone. That time that I didn't—I'm thinking of things specifically—could have put in a better word when they weren't in the room, and those are my failures, personally, is when I didn't treat people right or care enough or communicate properly. 

Joe Grover: [4:05 - 4:07] What did you learn from those moments? 

Kortney Osborne: [4:08 - 4:51] One, to have grace for yourself. Apology goes a long way. And just generally to treat people right. I think what I've learned from those moments is where was the source of me not treating someone right, understanding the emotion I had in that moment and switching it later to go, “I have grace for myself, I can forgive myself, but I do have to actively say sorry.” I've said sorry to you when I didn't say treat you right. And I feel that, and I feel bad for it. So, I don't know. Lots of learnings. But I also am just a human having a human experience. And I can improve. 

Joe Grover: [4:51 - 5:28] I know. The hard part about building a business and growing a company is people, right? It's all the interpersonal issues. It's the partnership issues. Right. It's the disagreements and misalignments and miscommunications. That's what really causes so much friction in the growth stage of any company. I also think a lot about marketing. This is the first time we've had a bunch of founders on the podcast. But what role does marketing play in the success or failure of businesses? Because I've been in some doozies, right? And how would you answer that with respect to Qualtrics? 

Kortney Osborne: [5:29 - 6:44] Ooh. In the perspective of Qualtrics, the success or failure, I think that marketing—I have a Rolodex in my brain going through, so I want to pick the right one. I think that marketing put Qualtrics out over its skis constantly that product had to catch up. And the product was amazing. Jared Smith's visions there were incredible. And he was part of putting us out over our skis. But we were messaging ahead of what we had. And that can be good or bad. It can bite people in the butt sometimes. But we recategorized the company. We would go to these events, and we were hashing things out till two in the morning of what the product roadmap was going to be presented to the entire audience the night before. Right? So then customers would come to us and say, “We want to buy that.” And we'd be like, “Sure,” right? There's scramble, right? You sell it. So in terms of marketing at Qualtrics and what it meant to the success or failure, I think that having that bigger vision ahead of what you currently were is what constantly pushed it forward. 

Joe Grover: [6:45 - 6:52] But you're walking a tightrope. Because I remember when Qualtrics flipped from what I thought was a survey company. 

Kortney Osborne: [6:52 - 6:55] Pedaling surveys over here. They're still pedaling surveys.

Joe Grover: [6:55 - 7:56] Totally. But all of a sudden, they were like this customer experience platform. And the vision was so much broader and higher value to your core customer. And I remember getting on the phone with a sales rep 10 years ago and maybe, probably seven years ago, and they're like, “No, this is like an enterprise solution. It does so much more than a customer satisfaction survey.” And InMoment was in our same building at the time, right? And they do a lot of satisfaction surveys, and they've had success in their own right. But Qualtrics went to $8 billion. And so there's this tightrope as a marketer when you want to sell ahead of product a little bit. You want to share that audacious vision and product roadmap. But if you sell it too soon, you end up having a bunch of customers who are buying vaporware: stuff that doesn't exist. You can't deliver on the promise. How do you gauge how far ahead you should be in marketing versus product? 

Kortney Osborne: [7:56 - 8:57] And part of it was I got to learn from that. And then I got to start doing it myself. So part of it is I got to learn from people inside Qualtrics pushing that. So. But what I learned from that and then continue to do is tie it to the outcome. And that's what I think Qualtrics did is they found this gap. And they talk about the experience gap, ultimately. But the tightrope is “Can you actually deliver the outcome? Can a customer experience survey deliver to a business experience management for their entire business?” And the answer was yes. And so I think pushing the envelope, you don't want to go out and be like—and I did this a few times where I went a little too far and it bit me in the butt. But you tie it to the outcome of what value you're driving for the businesses, and then you can catch up to that. But if you're going beyond what you can already do, then you are going to—it's a tighter rope. 

Joe Grover: [8:57 - 10:00] I once was sitting with a VC in Silicon Valley with the founders of another business, and I built three slides in a cab or an Uber on the way to the meeting with a vision that I thought was really compelling. And I remember we did the whole pitch about what the business was and our traction and the same 15 slides I had done a hundred times. And we got to these three, and I said, “Well, let me show you what's next.” And I remember, all of a sudden, the VC leaned forward and was on the tip of his chair. And he's just super engaged. I just shared this vision that I literally made up and he loved it. And he's like, “Well, how far off? When do you launch that?” And I hadn't even talked to my CTO. He was so upset with me. He's like, “What are you doing? You can't just make up the product vision.” And I was pressure testing a little bit. We ended up not raising money from that particular investor. But I remember at that moment thinking, “Okay, that was a little bit of a failure moment for me, or at least a learning moment.”

Kortney Osborne: [10:00 - 11:05] Well, it’s because you didn’t bring the people along. And so you gotta bring the people along. And I think that the people in the room that are like, “No,” are just as valuable as the people saying yes in the room. But put them all in the same room as you're pressure testing. And, full transparency, when they first came up with the XM model, I didn't love it. I was the person going, “What? XM? Like SiriusXM, the radio station?” Really, I was the contrarian a little bit in the room. And it took me a bit as we figured out what the strike moments of launching this to get behind it. But you, in that case, the vision was probably right, but people don't like not being considered. We talked about this once. Consider the people that are going to do the work, try to bring them along. And sometimes you have to have the moment of, “No, this is what we're doing.” But most of the time, you very rarely have to put your feet in the ground and tell people, “This is what we're going to do,” if you consider them along the way.

Joe Grover: [11:05 - 11:15] I love that. So you had this—there was a vision: an idea for this massive event at Qualtrics. Can you talk to me a little bit about the origins of X4 and what your involvement was there? 

Kortney Osborne: [11:15 - 12:04] I proposed—it wasn't X4 at the time: It was the Qualtrics Insight Summit at the time. And I just saw a vision for me personally of “I want to bring our people together. I want to create a compelling event where our customers can get together, connect, and we can become the thought leaders that this industry needs.” And I proposed it, and that was a lesson in failure. I was told, “No, we don't want to do this event.” And sometimes the failure is just timing. And I had to come back. I had a better advocate for me at the time who then helped me recraft it a year later and then repropose that event and start that process. 

Joe Grover: [12:04 - 12:09] That’s amazing. And this was a big part of your role and focus at Qualtrics. 

Kortney Osborne: [12:09 - 12:11] Yes. Events and campaigns. 

Joe Grover: [12:11 - 12:22] And this was a huge event. So something on your bucket list, right, was to meet Oprah Winfrey. Can you talk about bringing Barack Obama and Oprah Winfrey to Salt Lake City? 

Kortney Osborne: [12:22 - 13:09] That, again, testament to team. That was a huge piece. Mike Maughan, Ryan Smith, Kylan Lundeen, John Johnson, all of them were part of that. And so part of getting celebrities to get to an event is getting one celebrity and then the other ones will come. And so we had this track record of Michael Phelps, Journey, Steven Tyler, where, when you build up a reputation, it's much easier to get other people on board. And so they actually got Barack first is what I remember. It was one or the other, but I'm pretty sure it was Barack first. And then Oprah was like, “Well, okay, I'm interested in knowing what this is. And then I'll come too.”

Joe Grover: [13:10 - 13:11] Did they come the same year? 

Kortney Osborne: [13:11 - 13:12] They came the same year. 

Joe Grover: [13:12 - 13:13] And so you met them both. 

Kortney Osborne: [13:13 - 13:15] I did not meet Barack. I met Oprah. 

Joe Grover: [13:15 - 13:17] It's your happiest moment. 

Kortney Osborne: [13:17 - 13:29] I actually foregoed. I could choose at the time, one or the other. And meeting Oprah Winfrey was number 33 on my life list I wrote when I was 21. I wanted to meet Oprah Winfrey, and I met Oprah Winfrey. 

Joe Grover: [13:29 - 13:30] That's amazing. 

Kortney Osborne: [13:30 - 13:31] And I cried. 

Joe Grover: [13:31 - 13:32] That's amazing. 

Kortney Osborne: [13:32 - 13:35] And she gave me a hug. And it was the greatest moment ever. 

Joe Grover: [13:35 - 13:57] So putting on an event with 10–20,000 people (I don't know how many people registered for that event), there was probably a lot of critical moments during the day. Was there an experience that was high pressure, like a near-failure experience or something that actually failed? Something like a big snafu. A guest didn't show up. Was there any experience that you look back on that was—

Kortney Osborne: [13:58] So many. 

Joe Grover: [13:58 - 13:59] So many, right?

Kortney Osborne: [13:59 - 14:45] Live events are so interesting. You get one shot. And I always gave myself a rule. I got to cry three times during the week of that event. That's all I got. I got three cries. Because it's constant adjustment. One time, I got a call: There was a literal fire. A literal fire started in the hallway of the event. And somebody's like, “There's a fire.” And I was like, “Well, can you put it out, or do I need to come help you?” And that's a lesson of just put out the fire. Any event that you do, there's going to be fires. Put it out and move on. But that's one. Literal fires in the hallways. 

Joe Grover: [14:46 - 14:51] Little and metaphorical fires. Put the fire out. Closest to the hall.

Kortney Osborne: [14:51 - 15:43] Put the fire out in front of you and then move on. It's a lesson in preparation of going through every detail and preparing. And I would do experience walkthroughs constantly of, “Okay, when they walk through here, how do they get to the bathroom?” All of these things. But then the day of, you have to let go, let God, so to speak. You prepare as much as you can, but whatever's meant to happen is meant to happen. No sound on stages. I mean, you could ask. It probably happened. But I always said there's back of house, and there's front of house. And as long as the front of house does not see the back of house and how the sausage is getting made and people running around like crazy—literally back hallways of how we get places—

Joe Grover: [15:43 - 15:44] There’s some chaos, right?

Kortney Osborne: [15:44 - 15:57] Chaos. Coordinator of Chaos used to be my name. That's okay. Presenting to your customer the experience that you want to give them is really important, but you have to know that it's going to be chaos behind the scenes. 

Joe Grover: [15:57 - 16:18] I love to hear that. Because what we see with Qualtrics or X4 or any company that's successful is we just see front of house. And I've always said it never is as good as it feels like when you're watching from the outside. And typically, it's never as bad as it feels like when you're on the inside. But some days, you're just like, “This thing is going to just veer off the road,” right? 

Kortney Osborne: [16:18 - 16:19] Yes. 

Joe Grover: [16:19 - 16:20] The wheels are coming off. 

Kortney Osborne: [16:20 - 16:36] Literally. We're yelling at each other. You know, there's just so many things. There were times when there's customers that cut themselves that you're so—yes. Front of house can't see back of house. 

Joe Grover: [16:36 - 16:39] And that's the case for—that's our job as marketers, right? 

Kortney Osborne: [16:39 - 16:40] Yes. 

Joe Grover: [16:40 - 16:49] Not to be disingenuous, but to ensure that that chaos is corralled and behind the stage.

Kortney Osborne: [16:49 - 16:53] And pretty. And there's a bow. There's a bow on the box. 

Joe Grover: [16:53 - 17:01] What's the single most important learning from those eight and a half years at the rocket ship? 

Kortney Osborne: [17:05 - 17:31] I owe a lot to Qualtrics. This isn't my learning, but I'm very, very grateful. And I think that the learning is the connections. That's it. I remember the night that the acquisition closed, and all of us were very surprised. We were supposed to go public four days later, and then we pretty much got the news when everybody else did. 

Joe Grover: [17:31 - 17:32] They preempted the IPO. 

Kortney Osborne: [17:32 - 18:40] And so the next IPO, my husband happened to be at the company at that as well. Anyway, long story short, I was around this table with some OGs and just talking through. And while, yes, you look, and some of the founders were there, and their bank accounts got really freaking big. But my biggest lesson was how you treat people. I met my husband there. The connection there. I saw people have their first children. I had people go through divorces. And these friendships and connections and learnings that happen in the context of business for me is the biggest lesson. And that Maya Angelou quote, “People rarely remember what you say to them, but they remember how you make them feel”? That's the truth. And so yes, there's really cool professional learnings and skills and all that. But sitting around that table, it's the connections and these friendships that I actually really learned from. 

Joe Grover: [18:40 - 18:59] So I love that. Is there anything you would do different as you look back? It's hard, probably because there was so many positives. But this is a podcast about failure. And so I've always said, “Hey, if I just bring on successful entrepreneurs who it's been up and to the right the whole time, we've robbed ourselves of the richest learning. 

Kortney Osborne: [18:59 - 19:05] It's not been up into the right, that's for sure. Sorry, I interrupted. 

Joe Grover: [19:05 - 19:08] No, no, that's okay. So what would you do different if you were to go back?

Kortney Osborne: [19:08 - 20:09] Start therapy sooner. Seriously, understanding yourself and your things that make you tick is huge and connected that for me personally. I don't really think that the real F word is failure. I think that the real F word is fear. And what were you fearing, and what would I go back and not fear? And so you are constantly out in the future fearing something that never comes true. And so when I go back and I look if there's things I would change, it would be lessen the fear that I was having in those moments, have a bit more of an abundance mentality, because that's the regrets and the moments I look back is usually when I was taking action in a fear-based perspective that I didn't love the outcome of how I showed up in those moments. 

Joe Grover: [20:09 - 20:14] Fear. Why is fear so dangerous as you're building a company? 

Kortney Osborne: [20:14 - 21:02] I think that the frequency of fear puts you in a scarcity mindset. And building a business in general is an act of belief. You have to believe in something. You have to look at it and say, “Okay, I think this can be built to something.” Fear can be good in some ways. It's okay to have constraints and be able to work with constraints. But if you're fearing something, you're going to be in more negative emotions. Shame, guilt, anger, pride—all of those are fear-based emotions, and you will act in ways that really don't benefit you as a human and in the long term.

Joe Grover: [21:02] I think this is so insightful. I think about the moments in my career where my decisions were fear-based. And you’re right. You show up in a different way. And oftentimes, it can cloud your judgement. The fear of failure, sometimes, or the fear of just not succeeding can absolutely drive us to make decisions that are short-sighted and not for our best interest long-term, right?

Kortney Osborne: [21:32] Or the best interests of the people around you. And I think fear almost aligns to a zero-sum game. And success—often, we're like “success and failure”—I actually think you can lose and still be successful. 

Joe Grover: [21:49] I agree with this. 

Kortney Osborne: [21:50] But winning, you can have won and been a failure.

Joe Grover: [21:58] One hundred percent.

Kortney Osborne: [21:59] You'd end up making short-sighted views and decisions that don't align to your personal values. 

Joe Grover: [22:07] Let me give you an example. I had to lay off a bunch of people, and my fear of that moment of significant pain—and I've talked about this in other episodes—led me to not cut as deep as I should have. And I literally did everything I could to preserve jobs. And because I was so afraid of how I would be perceived as a leader and the impact—which is, by the way, this is fair because as an empathetic leader, we should feel pain when someone loses their job because we didn't execute. Right. But the reality is that fear drove me to make decisions that were minimizing the short-term pain. And eventually, I still had to make the decision. I kept people that I cared deeply about because I thought, “Well, that's the right thing to do as a human.” It wasn't the right thing to do probably for the business and probably for them. I didn't do them any favors. It was all about the fear of how people perceive me, that the pain in the moment, I just didn't want to do it. So I put it off. And that's one very specific example of where I let fear dictate a decision when I should have used facts. And like you said, I love that you said that businesses are built on belief, and fear is on the opposite spectrum of belief. 

Kortney Osborne: [23:30] it really is. And you have to believe before you can take action. And if you're afraid before you take action, you're going to not love your decisions. Because I had an experience where it was the opposite. I had to lay people off. And it was the fear of how I would be perceived or fear of not speaking up or fear “I'm a more new executive, so this isn't my place.” Or “I don't understand.” I could have saved some jobs, I feel like. And I could have pushed the envelope to be like, “Why are we doing this?” And so it can be the same exact action that a leader has to have. And I could have had the opposite outcome, but it's still the same. 

Joe Grover: [24:20] I saw fear dictate a lot of decision-making in Silicon Valley and in the VC community when COVID hit, I don't know if you remember this. Sequoia came out with their presentation like this was like the end of business, right? And then all of the VCs, both in California and here in Utah, they were all talking to their founders, and it was all “Batten down the hatches, preserve cash, do the layoffs now. It's all about runway. We don't know what the future holds.” And it was fascinating because this was a moment where we got together as a management team and we're like, “We're one week into a pandemic, and if we lay off 25 percent of our workforce and there's a tailwind because of this in our industry, we're just going to have to go rehire those people, and it's going to disrupt business operations and probably there's millions of dollars at stake. There's also millions of dollars at stake if we don't make the tough decision to do that.” So we decided to sit pat. And my CEO was like, “All the other CEOs in Silicon Slopes are chatting, and they're all laying people off.”

Kortney Osborne: [25:34] Well, they were all laying off. And then it was fear-based. But then they also could look at others to justify their decision. And it was a rough time. 

Joe Grover: [25:44] Wasn't that an interesting moment? And then guess what happened. COVID was a tailwind for lots of industries and a lot of companies. And then it was a scramble to rehire to build out your teams. And there was a lot—

Kortney Osborne: [25:56] And look at all of the cultural impact it had on all those businesses. I don't think even four years later some of the businesses that I saw that made those decisions have recovered from a cultural perspective. They never recovered some of the X factor of why great businesses get built because they made short sighted, fear-based decisions. 

Joe Grover: [26:20] I agree. And there's some herd mentality at work there too. By the way, I broke my hand. So if you're watching on YouTube, I broke my hand in two places skiing. So we'll talk about that in the next Real F Word. That was a big, epic fail for me. So anyway, most people are listening, and they have no idea what I'm talking about. But I broke my hand in two places. So I'm in a brace until it fully heals. 

Kortney Osborne: [26:43] And it hasn't slowed you down one bit, Joe.

Joe Grover: [26:46] Listen, maybe a little. I type a little bit slower. My fingers are chubby. All right, so let's talk about Weave. So you're the VP of marketing at Weave. And you really were preparing for an IPO, but there's tons of turnover in the executive team. Tell me about that experience and what you learned. You had five CEOs?

Kortney Osborne: [27:10] Four CEOs in 12 months. I left before the fifth CEO came in. And I love Weave. I loved my experience there. And now I feel like I'm almost just a self-fulfilling prophecy based on what I just said to now it's like rolling into it. So I'm a little clouded on that fear. That example of the layoff I used and that herd mentality happened while I was at Weave. And watching people not think through beyond themselves and making decisions that they weren't really thinking about what they were building long term and like looking at the future. You don't want to look too far in the future, but you have to have a belief that you can weather storms because you've built something really amazing. And Weave—so, super positives. I think we're talking about failures, so I'm naturally inclined to think there. But Weave was a wild ride, and I don't know what to say because it felt like a fire hose of learnings. 

Joe Grover: [28:38] So what role did the changing of the management and executive teams, how did the company ebb and flow through all of that change? 

Kortney Osborne: [28:47] Not well, in my opinion. I think that we kept building. But for me, it was a giant lesson personally and, seeing it in others, in ego. Your ego and how it can play a role in how you lead others. And I feel like my ego was triggered so much through all the changes that I didn't always show up the way that I wanted to show up and felt combative at times because I didn't have the empathy for others and didn't think that they might be trying to have the best out—they might have the best intentions. And that was a personal failure for me. 

Joe Grover: [29:41] What do you think? What role do leaders play? And, in particular, ego: Let's talk about that a little bit. Because there's a certain amount of self-confidence that is required to be a strong leader, right? You have to be able to make decisions and lead people and be direct and articulate. But if there's too much self-confidence it becomes overconfidence or even egotistical or narcissistic, it actually can be a huge contributor to the ultimate failure or underperformance of a company. What role do you think ego and leaders play in success and failure? 

Kortney Osborne: [30:20] I think that there does have to be, to your point, a certain level of ego. And because there has to be a certain level of self-confidence to become a leader and lead people in all of the things that's going to happen within an organization, you have to have that belief, and you have to have someone that you can believe in. And so there is a level that has to be there. And I look at some of the leaders that have built the best businesses that I was part of. You know, Ryan Smith. That guy has self-confidence beyond. It's awesome. 

Joe Grover: [31:04] He has a presence. You just walk into the room and you can just feel it. 

Kortney Osborne: [31:08] Brandon with Weave, and when I started there, he just has a presence about him. And what I'm going to say is not specific to those two. Those are just two great examples of leaders with really great presence. But what it can do is make you feel like you are the center of the world and you are the center of that company. And what I've seen with that switch is when it gets a little too much is you start thinking that you built the whole damn thing. And you didn't. So you have to have humility while you have self-confidence. Be confident in yourself, be confident in your vision. But you need to have humility to understand that all these people are with you, and let's get everybody rowing together. You might be leading the charge, but you're not the one slaying all the dragons, so to speak. People are slaying those dragons for you, and you need to have gratitude. And so that's why what I'd say is ego is fine. I think it's the humility that balances it, and that's where you continue to listen to those around you, and you won't get stuck in feeling sorry for yourself. Because I've seen leaders feel sorry for themselves, and I just think be humble. 

Joe Grover: [32:26] I was working with an entrepreneur who I quite like. But it wasn't ego in the sense that he thought he was the best person ever, had all the answers, but it manifests itself in the smallest ways. Like “I'm not listening to counsel from others,” being dismissive of that counsel or those recommendations from other members of the team. Not believing that he did have full context all the way down to the individual contributors who were building the business. And that manifests itself in decision-making that actually led the company into a really perilous place. And ultimately, I don't know if the company will survive. And it's not because he wasn't well intentioned, it's just that, over time, over many years, 15 years, he developed this, “Hey, I know this business better than anyone. And so I don't really need to listen.” He would listen, but not actively. And then, guess what? He's also the person who will have the biggest loss if the company doesn't make it out of this. So I've seen that. And so I think ego and leadership in particular are such a key principle in success and failure. VCs know that. They're betting on jockeys, not horses, right? And to balance confidence with that humility and just being rooted in reality that you're building as a team, not as an individual, I think is critical. 

Kortney Osborne: [33:59] And relatability that's rooted in reality. I remember having a conversation, actually, in specific to the layoffs, and a prominent executive was like, “Well, they should have had money in their coffers.” And it was like, “That's not rooted in reality. You make multiple six figures, and you're about to lay people off that make $30K. It's not rooted in reality.” And so you can have confidence and experience, but the ego says, “I am better than everybody, and I have to attack anything that's different than me often.” And so ego might not even be the best word, but the confidence versus cocky and rooting that with humility and reality allows you to bring everybody with you. And that's, for me, success. Did everybody get brought along or were there dead bodies in the street? And I don't view leaders that leave dead bodies in the street as successful. I don't care how much money you made. 

Joe Grover: [35:02] That's cringeworthy. “Oh, I'm gonna lay this person off.” Well, that's on them for not saving more? You've been paying them. They make a tenth of what you make. 

Kortney Osborne: [35:11] And it's just, again, I love what you said: rooted in reality of humility and being willing to sacrifice yourself sometimes a little bit for the good of others. And I don't see leaders do that often. 

Joe Grover: [35:28] So as consultants, we work with a lot of companies that are growth businesses, small and medium-sized businesses, and we've seen our fair share of successes, and we work with companies right now that are in the turnaround, right? And they're trying to figure it out. What is the pattern that you see across these businesses? I work primarily in consumer products. You work in consumer and SaaS and software and services. Let's just have a conversation about what are the patterns that we've identified as fractional executives that we can share with entrepreneurs to say, “Look out for these things.”

Kortney Osborne: [36:03] I think the first that I've seen is what has gotten—I deal mainly with growth businesses. I have worked with some turnaround. And so, from a growth perspective, what got you there is not going to get you there. So I can't remember the exact way to put that. But what got you here should not be forgotten. So don't throw the baby out with the bath water, but you do need to bring in somebody or something that is that next level. And I think so many people—I was just with the company that they've been at it for like 10 years, and they've just been stagnant, and they didn't want to create the plan and do anything different. “Well, this is fine.” Well, what got you here isn't going to get you there. But when I see turnaround organizations, it typically is ego. But I'm thinking of one in particular that we worked on together. And not listening to somebody that might have a different perspective, feeling like this is your business, it's only you, and not saying others might know something, even inside your company—people that have been at it with you for years. Have you asked? Have you listened? And I think that cockiness gets in the way of people, and then they just start going down a rabbit hole, and then they get tighter and tighter and tighter and scarce and scarce and scarce that they can't hear anybody. 

Joe Grover: [37:36] I feel that. I was working with a founder who said, “Hey, there's no need to change this business. We've been doing this, and this model is the right model,” and was so resistant to the idea that we had to pivot or make a really substantive change to our business model to survive that he ended up just doubling down on the same strategy, the same acquisition strategy, the same message, the same business model. And guess what? It didn't work. 

Kortney Osborne: [38:06] Probably didn't work. Right? 

Joe Grover: [38:07] It didn't work. And the resistance to change because you had something so valuable 10 years ago. And I see this—

Kortney Osborne: [38:14] People fear change, which is wild to me, but I also understand it and why I went to therapy for a long time. Because this fear of change, change is constant. It's a day by day, product by product, campaign by campaign, program by program. Change is constant. And so even those that resist change don't realize they have been changing this whole time. 

Joe Grover: [38:44] you went to therapy because—sounds like you've had a relationship with change that has always been healthy. 

Kortney Osborne: [38:50] I remember a boss saying to me, and it was such good advice, but I couldn't even hear it at the time, “Stop trying to white knuckle everything.” And change was one of the themes. 

Joe Grover: [39:03] Oh, that's so interesting. I feel that. 

Kortney Osborne: [39:06] But it's a natural human thing. You want to get comfortable. But change is continuous. And I think with businesses, it's continuous. And I think even because this is connected to it. But they fear this change. They fear this evolution. They fear this, and sometimes they fear the growth. But what they do, instead of just looking at it holistically, they look for a silver bullet. And I see this with marketing: They think, “Silver bullet: We're going to throw a PPC campaign.” And your whole business is 50 dials. You gotta change things here and there. And one silver bullet isn't going to change anything. 

Joe Grover: [39:52] So there's another learning there. I think that, “Oh, it's just this one more campaign or this one change or this one hire is going to solve the problem.” I think that there's this oversimplification of what it takes for a business to be successful is also dangerous. I love that you said there's 50 dials. How many times does someone show them, “I need a CMO. I need more leads. I need more revenue.” And they just think we're going to come in and it's like magic. We're gonna be like, “Yep, okay, let's turn this campaign on. And all of a sudden you have a thousand new leads.”

Kortney Osborne: [40:26] Can you fulfill that with your product? Can you onboard the customer? I don't want to complicate it, because I don't want people to be like, “Oh, it's so complicated.” Because to change, that's not my intention here. It's just don't be afraid, and don't be afraid to look at the whole picture because it might be something you weren't expecting that ultimately leads to the success. And It'll probably be two or three things that lead to the success. 

Joe Grover: [40:52] That's right. Fifty is a lot. 

Kortney Osborne: [40:53] Fifty is a lot. 

Joe Grover: [42:20 - 42:25] Entrepreneurs are like, “Dang, if Joe and Kortney come in—” 

Kortney Osborne: [40:57] I didn't want that.

Joe Grover: [40:59] But let's not oversimplify it either, right? Lots of things have to line up for business to be successful and sustainable over the long term. So other learning/other patterns of failure, one that we've talked about on this podcast is this balance we've talked about of confidence and overconfidence. And I feel like entrepreneurs are overly optimistic in ways that drive decision-making that is sometimes myopic. And, case in point, is every forecast I've ever seen, right? You and I were working on a forecast last night, and I was staring at it, and I started at “$10 million,” then I'm like “$9 million. Wait a second, this is like 263 percent growth.” And now I'm at 7 million. And I'm still wrestling as I'm trying to coach these businesses to just make sure that we're not so optimistic about the prospects of our business that we make decisions based on a plan that says seven when the reality is we might do five or a plan that says 70 when maybe we do 50. How do we balance this optimism that's required and overoptimism that leads to bad decision-making? 

Kortney Osborne: [42:18] Two things came to mind, and one was a pattern as well. The first thing is “Why?” Why do you want to get to seven? So you think you can. I am shocked at how many businesses I talk to when I say, “What's the goal?” they do not have an answer. Or “Why are you in business?” They don't have an answer. “What's the end goal?” Don't have an answer. So if the forecast is really big, that's okay. So first, know why you want to do what you're doing and spending your time doing what you're doing. Money is not your most important resource. Your energy and your time are your most important resources. You can go make money. I believe we could have a whole conversation about my view on money and how it's changed. But they want to go make these things. You need to know why. And that's a pattern I see constantly. People don't know why. They just want to build for building's sake. They want to grow for growing sake. Maybe only growing to four gets you everything you want in life, but you want to go to grow to $7K? Great. You have a good reason. Now at seven, let's go down that path. I think the other pattern that I see is an inability to make sacrifices or change what you were going to do to get there. If you want to get to seven, I can get you to seven. But are you willing to spend 17 percent of your revenue on marketing? No? Then I can't get you to seven. You know, it's this constant “Go forecast big.” But what is the plan? The horizon point is way out in front. What tracks are you going to lay in order for the train to go really fast? Because it's not that you can't get there, it's that there's too much friction along the way that you're unwilling to make changes on that doesn't get you there. 

Joe Grover: [44:07] And you don't lay the tracks. 

Kortney Osborne: [44:08] You don't lay the tracks ahead of yourself. 

Joe Grover: [44:10] I love this. So you and I had this conversation about building our practices where you're like, “Well, why do you want to do it?” And I was like, “Blah, blah, blah.” I had some answer. And I remember you were really incessant. You were like, “No, no, Joe. Why?” Right? And it's interesting because if we define success always by some financial outcome, we could spend our whole lives chasing it, and we will have missed what true success was along the way. The impact we have on people, the joy that we can have, some work life balance. Relationships and connections. And so maybe some of the biggest learning is around failure is it's really how we define success that dictates whether or not we ever failed at all. 

Kortney Osborne: [45:08] Exactly. 

Joe Grover: [45:09] And I think we— just as a society, as a business community, as a tech community—we just define it with revenue and EBITDA and valuations and exits so often that if the end result is not that, then we're just like, “Crap. I'm going to be on Joe's podcast because I lost all my money.”

Kortney Osborne: [45:28] Or even if you do it by revenue and EBITDA and all that, that's even better than most I see. A lot of people are defining their success based on somebody else. They are. 

Joe Grover: [45:42] Oh, that's interesting. 

Kortney Osborne: [45:43] And I think specifically in the tech community—

Joe Grover: [45:46] —they're comparing to another. 

Kortney Osborne: [45:47] They're comparing to another. And I'll say the competition or when you want to do this or this. And so a lot of people, when defining that success, they don't even have their own perspective. They have the perspective of what somebody else is doing. And we saw this a lot in the tech community with valuations and when it got really crazy and people were raising money at crazy multiples. And do you need to raise money? Why are you raising money? And so, yes, I don't think you should define success based on financial outcomes. Financial outcomes are part of us living our lives. But what kind of life do you want to live? When was the last time—and I'll ask you this—when was the last time you enjoyed the life that you were building? You took a day off to sit in the house that you pay a mortgage on, to have lunch from the fridge that you have to pay the energy on? And that, for me, my husband and I, now, we take off every first Friday of the month, and we enjoy the life that we are building so hard to build. 

Joe Grover: [47:02] I love that intentionality.

Kortney Osborne: [47:03] And intention. Does everything you're doing have intention behind it? But then really question yourself: Is it sparking joy in my life? Is building this fun? And on days when it's really hard, we've had some hard days the last few weeks. 

Joe Grover: [47:22] We have. 

Kortney Osborne: [47:23] We have. We've yelled at each other. 

Joe Grover: [47:26] We have. 

Kortney Osborne: [47:27] We have yelled at each other. Well, I've yelled at you. I'm sorry, Joe. Again, I'm sorry I yelled at you. 

Joe Grover: [47:31] You're forgiven. 

Kortney Osborne: [47:32] But the intention of “Is this sparking joy?” Great. And if it's not, why? And is it leading to the thing that I'm wanting to have? I don't think people really know why they're doing what they're doing. 

Joe Grover: [47:50] I think this is so profound. And I'm going to take every first Friday off now. You know this. And I'm going to ask myself, “If it's not sparking joy, what do I change?” Because not everything we do is gonna be like sitting on a beach in the Bahamas. 

Kortney Osborne: [48:07] No, it's not.

Joe Grover: [48:09] Not everything we do is just like a party. But if it's not leading to an eventual moment of joy or a lifetime of joy, then what is the point? That's just robotic.

Kortney Osborne: [48:22] But that's the majority of people. It's just a fear. So we just keep going because we fear something, and we haven't identified the fear, and then we haven't created a path for us to let go of that fear. 

Joe Grover: [48:37] I love this so much. 

Kortney Osborne: [48:38] First Fridays. 

Joe Grover: [48:38] First Fridays. I'm going to take the first. By the way, I want you to know Michelle is probably listening to this. I'm going to take first Fridays off. 

Kortney Osborne: [48:48] Yes, good. But we build and we spend our time—again, which is our most important resource—building and creating wealth and all of this stuff. And we're not actually sitting and going, “What are we building for?” I know, I know. I want to sit and watch a Netflix series with my husband on Fridays? We're gonna sit in our bed, we're gonna smoke something, and we're gonna have a good time in our house that we're buying, that we're building, and we're spending so much time doing. 

Joe Grover: [49:23] I love that. I honestly think that this is one of those things. This is why this is like entrepreneur therapy for me is because I'm learning less about business some days on the podcast, and I'm learning a lot more about life and people and intentionality. And it's always a really, really good reminder to just ask the question, “Why are you doing what you're doing? Is it sparking joy? How do I do it in a way that sparks more joy?” And then quit yelling at your partner. 

Kortney Osborne: [49:56] I'm sorry. 

Joe Grover: [49:56] Just kidding. 

Kortney Osborne: [50:00] No, but to that point, I had to question myself too in those moments, okay, what was the fear? What was I angry about? Why was I angry about? And guess what? It usually is my own insecurities. And living a love-based life, because that's really, for me, the opposite of fear. And I remember—this is just an aside—I remember when I started my job at Weave, I remember writing what was my intention. And my intention was to say that love could exist in a corporate environment. And it's in my work journal, front and center. And it's, “Why am I doing this?” And I wanted to learn how to be a leader. I wanted to learn how to grow a business. Of course I wanted to make money, but I wanted to say I could fully be myself and love people and still have business outcomes. I don't think I succeeded. I don't. I think that I got five steps further. But just have intention. Why are you in the business you're doing? 

Joe Grover: [51:03] I will never forget the lessons we talked about: First Fridays. 

Kortney Osborne: [51:08] First Fridays. 

Joe Grover: [51:08] The real F word is fear. 

Kortney Osborne: [51:11] And the other one. 

Joe Grover: [51:13] And the other one.

Kortney Osborne: [51:13] The real F word is fear. 

Joe Grover: [51:15] And just asking ourself over and over in this entrepreneurial journey—which is hard and a grind and requires personal sacrifice that nonentrepreneurs probably can't fully comprehend and understand—to ask ourselves, “Why? Are we headed in the direction that brings us joy, brings us connection, brings us love, even in the corporate environment.” I think these are all profound life lessons, not just entrepreneurial lessons. 

Kortney Osborne: [51:44] And I think as you look at the why, it's easier then to get back to the present moment of “Okay, I can get myself calm, I can get myself collected, and I can just be right here right now because I know I'm headed in the right direction.” You shouldn't be constantly looking up at the horizon asking yourself why. I look up every couple years, and I'll be like, “Oh, I am in the right way.”

Joe Grover: [52:12] I love that. Kortney. So a parting thought for the podcast: Lots of entrepreneurs and founders are listening, and they're probably wrestling with their own challenges. If you're a founder who's struggling to grow your business efficiently—maybe you've stagnated—what's the one thing that they should do? I know that's such a loaded question, but what's the overarching question they should ask themselves or the one thing they should do other than hiring you as their fractional CMO, which I also do recommend. 

Kortney Osborne: [52:49] Thank you. Thank you for that endorsement. 

Joe Grover: [52:50] That's a nice sales point. 

Kortney Osborne: [52: 53] What's the one thing they can do if they're struggling? Ask yourself, are you struggling? Really? I think that the first is acknowledgement of why? What are you struggling at? Because a lot of people go immediately to the actions of “What are the things I need to do differently?” But are you even struggling? I'm shocked when you're like, “Oh, we only grew 10 percent last year.” Are you struggling? Or do you have some random number that doesn't make sense in the context of you? So that's a really simple answer. But ask yourself, why are you struggling? 

Joe Grover: [53:35] Check yourself. 

Kortney Osborne: [53:36] Check yourself.

Joe Grover: [53:36] Check your reality.

Kortney Osborne: [53:38] And ask your why. Why does it need to be different than what it is right now? Because fear is in the future. That's the real F word is fear. But fear is in the future. And you're fearing some future that you haven't quite defined for yourself. 

Joe Grover: [53:56] So are you cohosting the Real F Word season 2? 

Kortney Osborne: [53:59] If you do it in my house, in my basement. 

Joe Grover: [54:02] We might be filming live at the Osborne residence in 2025, so you're welcome to come on anytime. 

Kortney Osborne: [54:12] Maybe. It really is a situation that I don't like leaving my house. 

Joe Grover: [54:16] I know. I'm just teasing you. 

Kortney Osborne: [54:18] To get in the car—if I could teleport, maybe. 

Joe Grover: [54:22] And if you've been to Kortney's house, it's a nice place. 

Kortney Osborne: [54:25] I have a dope house. 

Joe Grover: [54:26] Why would you leave? 

Kortney Osborne: [54:26] I have a dope house. I have good energy. 

Joe Grover: [54:31] I might just start working there. 

Kortney Osborne: [54:32] Come. I mean—

Joe Grover: [54:33] plenty of rooms. 

Kortney Osborne: [54:35] We've got too much room, and it's like, come and hang out. 

Joe Grover: [54:38] Thank you, Kortney, so much. 

Kortney Osborne: [54:40] I'm Kortney Osborne, and I'm an entrepreneur. And I don't believe in failure. I feel like it's all learning, and through my time at Weave, Qualtrics and now building my own businesses, failure isn't the real F word. Fear is. 

Joe Grover: [54:55] Thanks for tuning in to the Real F Word. The real F word is failure. And remember that failure is a stepping stone. It's not just a stumbling block. Join us next time as we continue to explore the journey of resilience and growth without ignoring the true cost—personally, professionally, and financially—that comes with failure. Keep learning, keep growing, and keep embracing the real stories of entrepreneurship. See you next time.