Why Leadership, Culture, and Mindset Decide Business Success

Welcome to the Legacy All-Stars Podcast. We feature inspirational stories from people who dedicate themselves to helping others. Here is your host, Alan Pavlosky.

Welcome back to Legacy All-Stars. This is part 2 of a special 2-part episode of Legacy All-Stars Podcast with Sabrina Parsons, CEO of Palo Alto Software. I hope you enjoy the show. Yeah, I can fully corroborate that from my own personal experiences. So that's great. You often talk about, and this is right along that same subject matter, but you often talk about an integrated life instead of work-life balance. What does that look like in practice?

Yeah, I mean, I guess it's, you know, it's one of those things. And for me, it really came, I sort of had an aha moment actually with the Sheryl Sandberg Lean In book where I read it. I very much look up to her, right? She was COO of this enormous company, obviously very accomplished. I didn't— lean in didn't resonate with me. This idea that you lean into what has been much this corporate world built by men for men, and that to be successful as a woman, just lean in, that's all you have to do, rather than, wait a minute, why don't I just be me, work just as hard but on my terms, don't apologize for being a mother, for having children, but have some different kinds of flexibility? Because balance, when they say work-life balance, right? It's like you've got the two scales. Well, with that idea of balance, the more you work, the more you— like, it doesn't make sense. How, how does that work? If you have more work to do, then you're supposed to do more over here. And that's like, it's like this idea that I think many women my age who grew up in the, you know, '80s and '90s, this idea of Superwoman. You can do it all. Well, you can't really, right? Our society isn't built for that. But if you can integrate, if kids can come into the office, if your babysitter's sick or your daycare closes and you've got a 7-year-old, a 7-year-old's not gonna scream all over the office, right? You can bring them in, they can have things to do. We have board games, we have coloring books, we have reading corners for kids, we have Nintendo PlayStation. Like, if I can bring in my kid, then I'm not worried about them. I don't have to take the day off. I can still come to work. And in our company, we don't care if the 7-year-old is in the meeting. You know, obviously there's obvious caveats to like they have to behave, etc., etc. But we've had dogs in the office for years and that's always been okay. But God forbid a kid comes into the office like that is not okay. And so that's really my philosophy around integrated life is just Own we are, you know, full humans that have other lives and we are not slaves to our jobs and no one is. And if you've got a sick mom at home that you're worried about, you're not focused on your job. If you've got a sick child, you're not focused on your job. So let's just own that and give people the flexibility and the permission to really own their lives and do the work when they are able to take time off when they are able to bring in their kids if they have to. And at the end of the day, you retain people for longer and people are less stressed out. And when you're happy, you're also more innovative and productive.

That's right, for sure. What are the most common mistakes entrepreneurs make when developing their business plans? And I know I'm going to get into more granular detail about the software and what it does and how it helps people. But that's my first question centered around that.

So lots of— I can go through a list of 10 common mistakes. A couple of the biggest ones we see. Number 1, people will initially do a forecast and set everything up and they will not include their own salary to pay themselves. And when, you know, when I work with them, when I mentor them and we look at everything, I say, where's your salary? Well, I'm investing. I'm investing like This is my investment in the company. It's like, okay, you still have to put it in because the company has to be viable with this salary because you are the founder and the entrepreneur. So you still have to put it in. And if you can't pay yourself initially because you're going to be self-funding, then put it in and then make sure you're applying your salary to equity because if in a few years you take on a partner or you go out to angels or something, you need to have something on the books. So I would say that's one of the number one things we see is that entrepreneurs, especially in a startup when they're trying to bootstrap and be scrappy, they don't pay themselves and they have to, even if it's just debt or equity that they're putting in the company. And then the other thing I see that can really kill a company is not actually understanding the difference between profit and cash and not doing a cash flow forecast that accurately helps you understand the cash side of things because the bank balance and the profits on the P&L are not the same. And it's really hard for people to understand that. Yeah.

Couldn't have said it better myself. What habits or disciplines consistently show up amongst founders who do succeed?

You know, I think it's like one of the old adages, and I find myself sounding like my parents and my grandparents because now I have a 21-year-old and a 19-year-old. And so I say this to them: 90% of it is showing up every day. Yeah, you just, you got to do the hard work. It sounds very romantic and glorious, and I'm going to be a startup and I'm living my dream and it's the American dream. It's a lot of hard work. It's a lot of just suck it up, show up, and be willing to do anything and everything. That I would say is my number one piece of advice, which sounds so simple and old school, but it still rings true. It's been an interesting tie-in. Sons, all three of them are great students but also very good athletes. Both my boys in college are D1 athletes. Throughout, especially in high school, as they were excelling, they're rowers. Um, rowing is a very demanding sport, very physical, lot of hours. And a lot of the times they had frustrations with teammates who wouldn't do the work, who wouldn't show up. Because in our house, that was a huge thing. It was, hey, this is your thing. I'll support it, but you got to be the one showing up. You don't have to do it, but if you commit to it, you better be doing the work and showing up. And I think that more than anything is what brings success in life. You just have to show up every day.

100%. And, you know, I have a background in sports, so a lot of the athletes that I've worked with over the years, they can translate those skills and those habits from athletics athletics into their business life. And I think I've, I've seen some really great examples of those that have been able to do so effectively.

Yeah, I saw some of that in your background, and I was curious because it's been such a big part of my kids' life and our family life. And I also think, I mean, my kids are the COVID high school generation. It's been a very— it just was not the normal high school experience, and there's still ramifications, right? So my Oldest son is a senior in college. COVID hit at the end of his sophomore year in high school. Just a really tough time. My sophomore in college, he was in 8th grade at the end of 8th grade. So his first year of high school, he never stepped on campus as a high schooler, like never was able to go to the school. So a lot of ramifications of that, some of which being both of my boys have lots of friends who went to college and ended up coming back. College was really hard for them. They just couldn't really— like, it was lonely. They didn't know how to connect with people. They felt isolated. I think a lot of it coming out of COVID obviously compounded by all the social media and all these screens. My boys didn't have that at all because they went to college And day one, first of all, they went early because they had to for practice. And day one, they had a community. And it was all these super focused, disciplined athletes. And from the moment they got there, they had this friend group that extended from freshmen in college all the way to seniors. And this community of athletes who supported each other and made sure everybody showed up and everybody was there for each other and just this completely night and day experience than a lot of my friends and their kids have had, where they've had to bring their kids back. The kids have ended up living at home and going to school nearby or community college, but most of it had to do with not finding a community because of all this weird COVID stuff. And for my kids, it's the athletics and the academics have just made it just this completely different experience, and it's been the greatest thing that's ever happened to them.

Yeah, awesome. I want to get back to LivePlan, and especially with the advancement of AI tools, what are you seeing in the SaaS industry today?

Oh, that is— well, every day is different. So the number one thing we're seeing is you better be in there, you better be using these tools, you got to just be in it. You cannot step back for a moment. I think what we're seeing is it is very important to understand how to really, at least for us in LivePlan, really think about AI and the expertise we bring to the table and building those in and integrating them together. AI by itself, if you don't have the knowledge, if you don't know the prompts, if you don't know what a business plan is supposed to look like, You don't know if the AI created something that's good. Did it hallucinate? Is it facts? Like, you don't know. That's what we're bringing to the table with LivePlan. We're saying, hey, we've got 30 years of business planning experience and we're bringing that knowledge base and then we're adding all the facts you know about your business to our guardrails that are going to keep you actually building what you need. It's correct, it's professional, it's done right, and it'll teach you along the way. But it's a struggle every day, right? I mean, I think you and I have both lived in life where we've heard about, you know, every year technology is going to move faster and faster. And now we're at a point where I feel like every week, it's not even every year.

I'm somewhat of a power user when it comes to AI. If for my age bracket, I'm I'm probably in the 99th percentile of AI implementation. But I mean, I feel like it's every minute is changing. I mean, it was a couple of days ago when ChatGPT 5.4 came out. First of all, 5.3 came out a day or so beforehand, and then 2 days later, 5.4 comes out to compete with Claude. And it's just, it's a ride right now. It's a roller coaster.

Yeah. And I think that, you know, you think back to all those times when like people were afraid of all kinds of things, right? Computers. Phones, all these things. And, you know, obviously we're on the other side of it and it's the same thing. There's a lot of fear with AI right now and people who don't want to use it and are afraid of it. And it's like, this is here to stay and you better embrace it and figure out how to use it because it's moving too quickly and it's going to leave you behind.

For sure. I say that to people every day. Let me ask you this. Is SaaS threatened by AI or enhanced by it?

I think both. I think both. I think there are certain kinds of things, tools that are going to be more threatened and things that are super simple. I mean, I think there's been, you know, stories about companies like Monday. They have project management software and then, you know, some engineers vibe coded a Monday competitor in like 2 days, right? I think in some instances, if you have a tool that is maybe a little bit more simple, more straightforward, those are the software tools that are just process-oriented without the expertise that are going to be more challenged by AI. I think tools that have their knowledge-based tools that are educational, where you really need to bring expertise and knowledge into them. I think AI enhances it. Yeah, definitely. You know, and then we'll see. And like by the summer, you and I probably have a different conversation about—

And we might have to do that. But how do you see tools like LivePlan actually evolving alongside AI? I know it's tough to tell because of the rapid evolution of AI on an almost daily basis, but how do you see it right now?

Yeah, I mean, I think one of the things is like not being afraid and really allowing our engineers to explore and build and embrace. And like I said, for us with LivePlan, the tool is, you know, this is not just a project management tool, right? It is a tool to help you think strategically, to help you build marketing strategy, sales strategy, forecasts. We give you financial analysis. It's a very, there's just a lot to LivePlan. It can seem overwhelming to people. I think for us, AI has been awesome because we can help reduce the overwhelm while still guiding and leading and putting up those guardrails so that you can bring your ideas to the table and we've got everything else. Kind of like when spell checker came to like word processing, right? And teachers just about had a fit. No one's gonna know how to spell. And it's like, oh my gosh, it was the best thing that ever happened. So for LivePlan, I think it's a great opportunity, but you know, we're in there, we're innovating, and we're allowing our developers to have a lot of time to play because it allows us to feel like we can keep on top of all the new innovations, right? We don't necessarily need to be bleeding edge, but we need to be leading edge, and that means we're gonna explore things, we're gonna do things some of our tests are going to pan out and some of them are not, but we're not afraid to really just jump in.

Right, right. So I'm going to shift gears a little bit because this show is definitely about legacy. It's about helping others. It's about impact. And I want to talk to you about what you've done at the Oregon Growth Board and the role that you play there.

Yeah, that's been such a fun opportunity for me. So Oregon Growth Board is A board that is appointed by the governor of Oregon, got to be also voted upon by legislatures. And what we do at the Oregon Growth Board is we work with the Business Oregon Group, which is the state staff for Business Oregon. So everything to do with business in Oregon that's run by the governor of Oregon. And we are lucky enough to get lottery funds. And we get about $30 million every year. So not tons, but enough. And we invest those lottery funds into funds that invest in Oregon entrepreneurs. And so we get to play a little bit of a role of saying, hey, because what a lot of people probably don't know, but lottery funds are managed by investment consultant companies, right? Management consultant companies, and they invest that money. And that money returns. And that's how, you know, you do the right thing for the state of Oregon. You don't just have lottery funds sitting in a savings account. They're invested. And so in Oregon, a group of legislators said, well, why don't we take $30 million and let a board specifically focused on economic development and entrepreneurship take those funds and invest them in funds that will then support Oregon entrepreneurs. And so as my role on the board, I'm actually currently a co-chair of the board. We hear pitches from funds and we evaluate those funds on their returns, the industries they're in, how diversified does that make our portfolio. But one of the number one things we evaluate them on is their pipeline of Oregon entrepreneurs. Where are they finding them? Who are they funding? And are they truly funding Oregon entrepreneurs? We need returns because the legislature isn't going to just give us the money if we don't get returns. So we have to make good investments, but we want to support economic development and grow entrepreneurship in Oregon. So it's been a really interesting space to be in where at Live Plan, I'm working you know, directly with the people who start the companies. And at the Oregon Growth Board, I'm at that level where I'm working with people, you know, who have funds, who will fund the companies. And that kind of exposure just gives me a different perspective and different viewpoints. And yeah, it's just been great to be part of it and then to see entrepreneurship growing in Oregon and to feel like, oh, I had a little bit of a part to play in that.

Yeah, for sure. What excites you most about the future of entrepreneurship?

Oh, so many things. Um, you know, I think what excites me most right now is the way the technology is democratizing tools. I mean, that's been happening since the dot-com era, but it's happening faster and faster and faster and faster now. The way that you don't need $15 million to start a company anymore, that technology really has democratized it. You need knowledge, you need expertise, you need to find good founder partners, but you don't need the same type of money anymore. And so, you know, as we think about diversity, equity, inclusion, you know, what we all need to make sure is that we're educating young people so that they understand And I think it's opening paths where an entrepreneur doesn't have to follow that traditional path anymore, right? Go to an Ivy League college, be a management consultant or an investment broker, then go pitch Sand Hill and get venture capitalists. And that's the only route you have to be a successful entrepreneur. That's not the case anymore. Maybe college, maybe not. Maybe there's other things. And I think it opens up so many more opportunities for people who maybe don't see themselves in these very rigid kind of linear lives that they're not sure, is college for me? I'm really excited about this other thing. Technology is making accessible to more people what they can do and the kinds of companies they can start.

Yeah, and you know, I think The mold was broken kind of a long time ago when Bill Gates dropped out of first year of college and founded Microsoft. So, I mean, I think there's a lot of examples, even historically, in not only recent past, but in some fairly distant past where there was some people started to break that mold a long time ago.

Yep. Yep. And I think it's just going to happen more and more. And we're going to see some really interesting, innovative things happen from people and places that we haven't seen before.

Yeah, for sure. All right, this is one of my favorite questions that I always ask. What legacy do you hope your leadership ultimately leaves behind?

Oh, that's a great question. So the legacy of my leadership that's most important to me is what I do professionally and in my community and the way I have led my company and been in leadership leadership roles in my community has modeled leadership for my 3 boys. I am a mom of boys. I don't have daughters, but I have lived a life where I'm often the only woman in the room as a tech CEO. And unfortunately, the numbers have not changed the way we would have hoped by 2026. I oftentimes am advocating for women in sports. Particularly youth athletes, girls, they drop out at a much higher rate than male athletes. I talk about it with my boys all the time. I hope and, you know, help them. And sometimes I think they think I'm lecturing, but I think they get it that, you know, it's really important for them, but to understand the privileges that they still have as men and white men and male athletes. It's important for them to understand the context that women still have to fight in ways that I think a lot of times we all think that's not the case. I mean, case in point is this whole debacle with the U.S. men's hockey team and what they did. And, you know, I think I talked to all three of my boys that they all said, Mom, we would have said something because you would have killed us. And I was like, that— I will take that legacy. I mean, yes, you would have also done it because it's the right thing, but if it means that I have impacted that decision, I'm really— that is the most important legacy for me, is that I raised 3 male people who understand and live in a world where they expect different things out of themselves than what you've seen in sort of the normal, you know, male in America.

Yeah. Wow. It kind of brings me back. And just to dovetail off that, I had a previous episode where I interviewed my friend Clementine Painter, who was in charge of the initiative that was in partnership with Adidas in globally to help encourage and support female athletes to participate and to stay in the game rather than to leave it prematurely. It's a very important topic, and I think it's really poignant that you brought it up and that you are making an impact on that, even if it's just on the influence of your boys to make sure that they continue to advocate for that. I have two girls and two boys. I have a grandson. But, you know, I'm always trying to teach those lessons to them as well.

Exactly. Yeah. You know, like I said, it's 2026. There's some lessons I wish we had all learned, but we haven't yet, and that's okay. So we just have to keep fighting that fight. And the more people who bring a different kind of empathy to the table, I think the better off the world will be for that.

Yeah, for sure. Sabrina, this has been such a meaningful conversation. I'm so excited that we had a chance to sit down and talk. Behind every great tool is a philosophy about what business can do for people. The missing ingredient is always people. The work that Palo Alto Software has done over the years has helped countless entrepreneurs transform ideas into real businesses, businesses that create jobs, support families, strengthen communities. Before we go, how can our audience learn more about your work?

Um, if they want to come check out liveplan.com, they can see what the tool does, and if explore it. We have a 60-day money-back guarantee so they can try it. They can get their money back if they didn't like it. We don't want to take your money if it doesn't work for you. We very much believe in bringing value, and if we don't, then we don't want to take your money. So check out LivePlan.com, and we really are always there to just make sure that we're helping people succeed in business. That's our mission. We want to help people succeed in business.

I love that. Thank you again for being here. It's been amazing.

Great. Thank you, Alan. I really enjoyed it.

Yeah. Thank you. To our audience, thank you for joining us on Legacy All-Stars. Our mission is simple: to highlight leaders who are using their talents, influence, and resources to make the world a better place. If today's conversation inspired you, please share this episode with someone who believes that success is most meaningful when it creates opportunities for others. Until next time, I'm Alan Pavlosky, reminding you that the greatest legacy we can leave is the positive impact we make in the lives of others. Have a great day.