Season 2, Ep. 18 | Building What Lasts: A Conversation with Sabrina Parsons Transcript
More Elephant Intro
[00:00:08] Jason Rudman: What does it mean to inherit something and then have the courage to break it?
Today's guest was born in Mexico City, studied history at Princeton, taught in public schools, built a company in London, and then came home to run the business her father started in a garage. She took a profitable, stable Windows software company and told her team they had to change everything or they might not survive.
She was right, and now, nearly two decades later, she's facing the same question again, this time because of AI.
This is More Elephant. I'm Jason Rudman, and Sabrina Parsons, CEO of Palo Alto Software, is here to talk about what it really takes to build something that lasts. Welcome to the podcast, Sabrina.
[00:00:49] Sabrina Parsons: Thanks, Jason. Yeah, that's a great adventure. I don't know that's how I would've said it, but it sounds fantastic.
[00:00:55] Jason Rudman: Well that's what you did. We go with the facts.
And, so much of what we do here at More Elephant starts with what I like to call origin and identity. So I'd love to start in a couple of places. First, you grew up watching your dad build Palo Alto Software from scratch. When you look back at that experience, what did it teach you about risk, about work, and what it means to build something that truly lasts?
[00:01:19] Sabrina Parsons: That's a great question. So, in terms of risk and work, I think that I didn't quite understand it because I was a kid. My dad started thinking about this business and the opportunity for it when he was consulting, and it meant that he had to bootstrap. And, because he bootstrapped, when I was in elementary school living in Palo Alto, California, I was one of four children at the time—I'm one of five, but the fifth was not yet born—and we were in a three-bedroom, one-bath house where all four of the kids were in bunk beds in what was supposed to be the master bedroom, the primary bedroom. My parents were in the small bedroom, and my dad's office was in the third bedroom. And that was just normal, and I don't think I really thought about it when I was a kid. It was just like that's the way we all lived, and it was kind of fun.
Palo Alto is and always has been a very expensive place to live, so I definitely knew that I was like a poor kid. I had friends who lived in enormous houses, and I don't know if any of them shared a room with their siblings.
So I think that for me, it just was part of life and that was just my dad, and he was an entrepreneur, and that meant we lived a little bit differently than other people.
Because he was into software and technology in the early eighties, that to me was the biggest difference, because my dad was always trying to get us to use computers before they were really a thing.
I remember being in seventh grade, and he made me write my seventh-grade essay using a word processor. I don't even think it was Microsoft Word. Maybe. But I don't think anyone else was writing their essays on a word processor. And, I don't know what it is that I did but I deleted the whole thing and had a total meltdown, as a seventh grader would have. You know, I remember blaming my dad, "It's all your fault, the stupid computer."
And then, back when you could do this, my dad going into DOS prompts in the backup of the hard drive and somehow rescuing my essay and watching him do that. So, for me, part of him starting his business was this emphasis in our family on bleeding edge technology and embracing it and using it.
And now, as I think about it and think about the risks and the things that I've had to go through, that's probably part of my DNA, is just knowing that you always need to be using whatever's coming next, and you can't be afraid of it.
[00:04:22] Jason Rudman: A-amazing. And what you described, my follow-up question is as we listen to great guests like yourself, very often it's about exploring nonlinear paths, right?
As I mentioned in the opening, you studied history at Princeton, not computer science. You were a public school teacher before you stepped into a tech company.How did those experiences wire you differently as a CEO?
[00:04:46] Sabrina Parsons: Yeah. I think about it a lot because we have to hire people, so you look at their resumes, you look at what they studied in school. We've definitely hired our fair share of young people either right out of college or a few years out. So you're going to look at what did they study and how does that fill their resume.
And one of the things that I have always valued, and it's been at the top of our hiring list, is valuing college for teaching people how to learn and teaching people to not be afraid of what they don't know because in college, you learn to learn, and that's what you're doing. You have all these classes, and it doesn't matter what the subject matter is, you are learning at a different level, and you're often thrown into these projects, team projects, essays, different things, and you don't know, and that's the whole point of the class.
And so, from that perspective, the fact that I wasn't in computer science, I think I loved the idea of, for me, learning about history and that history actually is in the eye of the beholder. There isn't one truth—that history depends on where you're from and who's telling the story and what perspective they had. And so for me, that's why I chose history.
And then I take all of that and I go, Oh that's, part of what I love about what I do is I've always been on the sales, marketing, business development, negotiation side of the business. And I think history teaches you all these different negotiations and how to make a pitch, right?
That's what happens. We're seeing that right now in terms of what's happening in the world and who's negotiating what and what point of view and depending on where you are in the world right now, you probably have a very different viewpoint on what those negotiations look like and what does the reality that you see look like.
So yeah, for me, I studied history because I love that idea that it isn't actually true. It's just true for that perspective. And I think that is been something that I carry through my leadership and what I've done in business— to always remember that my perspective is very different, and that's okay. And so if you open yourself to what's their perspective and what are they coming to the table with, you probably will have more success, and I certainly feel like I have.
[00:07:33] Jason Rudman: From one history major to another, plus one to everything you said. And then I've got a twelve year old that happens to love history, and we were just talking about how you connect the negotiation skills and the game theory of situations and how that's actually going be useful in real life. Because I think, twelve year olds sometimes are like, "I'm reading this history stuff. Am I ever gonna use it again?" And the short answer is yes, you're going to use it many times.
I also mentioned in my open when you became CEO in 2007, taking over from your father, [the] company was profitable, well-regarded, selling Windows software. And I'm not quoting you here, but, or maybe I am. You in that moment said, "We have to change everything or we'll die." That's my interpretation of the pivot that you made.
Can you talk us through that moment and more importantly, what did you see that others didn't?
[00:08:22] Sabrina Parsons: I think before I really transitioned to be CEO, I was already worried and thinking about it.
So, there was that time to really engage in other technologies. Obviously, my dad is a different generation—the boomer generation—and he had acknowledged that, "Wow, you bring a different viewpoint to technology than me."
For me, I graduated from college in nineteen ninety six, and the internet exploded, so my entire working life has been...even though it was the beginning of the internet, it was the internet, so I've never been in the work world without the internet. And yes, I've seen it transition and grow, and things we thought would be here forever don't exist anymore.
Those of us who remember Netscape Navigator and you know, these companies that we thought would always be there. Even let's go to a company like Yahoo!, right? That was so huge in the late nineties, and my oldest son, who's twenty two now, when he was about twelve, somebody said something about Yahoo!
And my husband actually worked at Yahoo! right out of college. So summer of ninety six, he was the one hundred and first employee at Yahoo!, so early, early days. And obviously, Yahoo! has a place in my heart because that's where my husband started; somehow Yahoo! came up, and at the time, my twenty two year old [who] was twelve, and he goes, "Yahoo! What's Yahoo!" And just him saying that, I was like, "Oh my God, how is this possible that he doesn't even know what this company is?"
So, I think back then in o-seven, I already knew, and I was already worried that Windows is not where it's going to be at. The internet is ready. People are wanting access, and this idea that you could have a platform, a product that you could access from anywhere instead of "I've gotta have the program, and I have to have it installed on my computer, and if I don't have it installed, I can't work on it, and I can't do anything."
We used to live in a world where you brought your computer, and you never had the internet, and you were totally fine.
[00:10:41] Jason Rudman: The days of package software, right?
[00:10:43] Sabrina Parsons: Yes, but we were already on that path of seeing what was going on and products that were being very successful. I remember following Salesforce and their rise very closely; enterprise software, business software, and we do business software, and just seeing that and knowing this is where it's going to be. People are not going to be doing this. And so very much having the conviction to say I believe this so much that it almost, to me, felt like a risk not to do it.
[00:11:18] Jason Rudman: At its core, your company serves small businesses and entrepreneurs and helps them plan their passion.
As somebody in a corporation that has a role and planning is incredibly important. I view it as this living discipline, like it's always on the move.
Most entrepreneurs probably hear business plan and think, "Hey, I've got to generate a forty-page PDF," that they write once for a bank. I think that runs counter to the way that you think about it. So why do you view that thinking as faulty or problematic?
[00:11:53] Sabrina Parsons: That's a great question. And I love that you talk about at a corporate company, you guys are doing planning.
I think there's a myth out there for small businesses, startups, startup founders that you create a business plan to get funded, and that's the only purpose. The reality, and you know this working in a larger enterprise company, is that it's almost everybody else except small businesses embraces ongoing, systematic, regular planning, right?
Whenever we see market reports, and all these public companies are doing their quarterly results, are the actuals compared to the plan. That's what they are. And yet, we don't say that. We say, "those are quarterly results." And when you see Google put out its projections for its earnings; projections are planning, right?
So, part of what I think happens is that small businesses somehow, somewhere along the way, got fed this myth that the business plan is this old document, it's only for this one purpose, and then you never need it again. And is probably why small businesses often struggle with some of those pillars of what it is to run a business, right?
They say to themselves, "I'm a baker. I'm not a business person. I need to be baking these delicious, amazing things. I don't need to worry about the business." But, everybody who's running a business needs to worry about the business, and the reality is the bigger businesses, even private companies, they have boards. The boards require them to do planning.
Everybody else is required to do planning on a regular basis, and small businesses and startups are told, "Nope, you just do it once and it's for funding, and you never look at it again." And then, in the United States, we have this crazy statistic that sixty percent of the businesses, the small businesses, that go out of business were actually profitable. They go out of business because they run out of cash.
You run out of cash because you're not planning.
[00:14:08] Jason Rudman: A few episodes ago, we met with Heather Tuason, who is the CEO and founder of Arena.
Her company is in the fractional CFO space, and she talked about the fact that cash flow is king, and the failure rate is driven by that. So, it clearly aligns with your experience and making sure that fewer fail has tremendous economic and societal benefit. So, to any entrepreneur listening, when you've written the first business plan, that's not the only time that you actually need to plan.
[00:14:39] Sabrina Parsons: Exactly.
[00:14:39] Jason Rudman: More Elephant loves exploring culture and norms as part of what you've built and what you've transformed.
I read your culture piece on your site, and one thing that stuck with me was you've got many values: we solve for the customer; we're transparent; and then, don't ruin it for the rest of us, which I loved.
What does that mean inside your walls at Palo Alto Software?
[00:15:01] Sabrina Parsons: That's such a good question.
So, we hire really smart people. We want people who come in and can really make their own decisions and own their area, own their strategy, and we often say to people, "Ask for forgiveness and not permission."
That only works, though, if people really own that and if people understand that if you're not really deliberate about that, you are going to ruin it for the rest of us. And we are then going to have to have more meetings, and have checkpoints, and have reviews, and have policies.
But, if you're a really smart person and you're working with people and you respect each other, you collaborate, you ask questions. And, that's not saying people are off on their own and they can't talk to anyone. But if we say, "Don't ruin it for the rest of us," then it means, hey, we're putting that responsibility on your shoulders to make decisions as if you own this business. So, you know, you can pick.
We don't have some policy about how you do your travel. You don't have to use some corporate travel agent because people like to use the airline they have priority on. They do different things because it's useful for them personally. So yeah, don't book the five thousand dollar ticket if there's plenty of options under one thousand dollars—but you want to go on that airline because you're gonna get the mileage. And, if you do that, now we're going to have a policy, and now we're going to have to have someone checking it, and you've ruined it for the rest of us. And we all know we shouldn't book the five thousand dollar ticket. We should book the one thousand dollar ticket.
So that's what we're really trying to do there: when you empower and enable people, it does come with responsibility. And the more that our employees embrace that responsibility, the more we don't have to have policies, and the more, we can just say, "Go for it," because we know that people understand what that means.
[00:17:11] Jason Rudman: Yeah. I'm reflecting I work at BECU, it's the nation's fourth largest credit union, and we're working through some of this now.
I had a conversation with my team, and I said at the end of the day, every decision you make, every strategy we attempt to pursue, and it could be at the thirty thousand foot level, it could be at the one thousand foot level. There's two outcomes: value or debt. Choose value, right?
But I think what you're saying is, and I agree with you, because we're humans, we think, oh, on some level your description about the five thousand ticket is if I only do it once, it's probably going to be okay but the one time you do it creates the debt, which means I've now got to create a bunch of “no joy” work to police a travel policy. So let's not do that. Let's go for value.
[00:17:57] Sabrina Parsons: Exactly. Exactly. And if people really buy into the culture, we have found then we don't have to police it.
That if people really, part of that, we say, "We give you the autonomy to be awesome." We let you make your way. We don't put all these policies in place. We also value transparency. We're going to tell you as much as possible. We're going to disclose financials and where we are, customer acquisition costs and revenue and expenses.
The more that we give people, then the ask in return is use your judgment. Don't ruin it for the rest of us. You know, and it's almost, and I think your kids are just... Do you have a teenager yet?
[00:18:42] Jason Rudman: We're almost there where we are. We are T-minus sixty days.
[00:18:46] Sabrina Parsons: Okay. Well, raising teenagers is almost the same way, right?
It is about don't ruin it for yourself, not the rest of it. Make good decisions.Make good decisions.
[00:18:59] Jason Rudman: Yeah, but we have to remember that the frontal lobe is not connected to the back of the brain. But that's a whole nother podcast. I love your—I'm going to steal it shamelessly and I will always quote you, I promise—"We're giving you the autonomy to be awesome." That's so powerful. So powerful.
So I mentioned in the opening that AI is a thing and we're all reflecting on how that's going to change business models. And, before we talk about AI and the future of your business, I think it's important to ground everybody in what your business is, right?
So Liveplan is the core of your business. Would you take our listeners through what it is, what it seeks to do and how it's evolved over the years?
[00:19:38] Sabrina Parsons: Yeah. It's evolved a lot in the last year, and I'll talk a little bit about that because some of it is because of AI.
Live Plan, and even the name Live Plan, is very purposeful. It's this idea that planning is a living thing. It's ongoing. Live Plan helps an entrepreneur, whether they're a startup or an existing business, create the right size plan and strategy for their business. It is aimed at small businesses and most of our audience are people who are passionate experts about their business. They are not MBAs and that is something that they all say.
Oftentimes, "I hate the numbers and all this business stuff. I'm passionate about what I'm doing. I'm an expert in what I'm doing." So, we created a product that not only helps build the right size plan, forecast, and strategy, but also teaches along the way so that if you use the product, you will learn about your business, and you will get better at the strategy and the forecasting.
Ultimately, the biggest benefit you will see—I always say the biggest benefit I see because I use Live Plan for Palo Alto Software—is you will sleep better at night.
You're going to sleep better at night because you're going to make better decisions. If you do plan and you engage in planning, you're setting out that roadmap, and by setting out that roadmap, you have something to follow. Obstacles are going to come in your way and you're going to have to make decisions, to make different turns along the way, but you will have the data. And, by having the data, you will feel better about your decisions instead of what we hear all the time, right? "Ugh, gut decisions. I'm just making gut decisions."
None of us like making gut decisions.
[00:21:36] Jason Rudman: Right. So, let's pivot forward. You mentioned the business has evolved in the last year, the advent of AI.
And, what I'd love to do is try to separate substance from hype on some level.
Business was founded over thirty years ago; you've got thirty years plus of planning data, right? You've got pattern recognition at scale. And it's my belief that's going to produce a fundamentally different outcome than ChatGPT. I think when we were talking about this, you were very deliberate to say, "Hey, I've got an AI-powered assistant in LifePlan, but this is not just...I haven't just bolted it on to ChatGPT and off you go."
With the alignment what's the distinction? And more importantly, why does it matter from your seat?
[00:22:22] Sabrina Parsons: I think that's a great question, and I think the answer will change as we evolve because I've never seen technology change faster. And this is coming from someone who was born into the working world at the beginning of the internet, right? Nineteen ninety six. So I've seen a lot of change. I've never seen this much change this fast. I've never seen people's behaviors online change this fast.
All of you who are listening, the way you searched last year, it is not the way you search on the internet this year, and we all know that. And whether you've recognized that or not, you absolutely have changed the way you search and engage with your search results, and that has never changed faster.
What we're doing with Live Plan, and what we're building, is almost the same things we were doing back when we started Live Plan and even with Business Plan Pro, people would say, "Why do I need the product? I can just use Word and Excel."
Sure, you can, but then you have to know what is the outline, what do I need to include? How do I put the formulas together in Excel? Do I have the expertise or do I want to take the time to understand and learn how to take a spreadsheet and link revenue to expenses? And then building cash flow assumptions so that you actually get a cash flow with AR and AP. Do you have the capability and the expertise?
And most people were like, "No, you're right. I don't." We're almost in that same place now where sure, there's tons of AI tools, right?
ChatGPT, you can tell it, "Write me a business plan," and it will. Then you have to determine, is that the right outline? Is that what my funder wants? Is that what the bank wants? Do I know what the right outline is? How do I recognize that? Did it hallucinate something? I don't know. How do I check that, right?
And then, you have to start cobbling together different AI tools. Now I need to put together a financial model. I've heard that not all the AI tools are good for financial models, so now I have to figure out which one. How do I do that? Can I find one?
And then when it puts together numbers, again, what are they based on? Can I explain them to investors? Do I understand where those came from, right?
So, all of that is almost the same as when people would say, "I can use Excel and Word." We're hearing the same thing. What we've done in Live Plan is we've used our platform and our thirty years of knowledge of what a successful business plan is and our partnerships with SBDCs, with the SBA, with college professors all over the country, and we've built those rails for you.
And the AI that we have, we switch it all the time. We use different models as they evolve. You don't ever have to know which model we're using. We use different models for the financials, but then we are weaving our expertise into all of the prompt engineering so that you don't have to learn it, you don't have to know it. And then, we're also engineering all the checks and balances so that you don't get hallucinated information.
If you've ever gone to ChatGPT and you give it a business idea and you say, "Find me competitors," I will challenge anyone to do that because half of the competitors you get from Claude, from ChatGPT, from Gemini, they're fake and made up. I don't know what it is about the AI engines. That's what they default to, or they are competitors who used to exist, so they find them in Reddit, and then it turns out you go to the website and the website doesn't exist anymore, so that competitor isn't even there.
[00:26:19] Jason Rudman: So much to unpack there. I was talking with a couple of CEO founders, and they were reaffirming some of what you said. And it's interesting because you talked about calculations because I think what you said, and I subscribe to, is if you're generating your business plan in minutes and you're going to assume that AI has got it absolutely right, your point is no.
In calculation, a computer is deterministic and AI is probabilistic. And you can do this today, anybody listening, you can put some sequential calculations into AI, and you may get the different answer than if you put it into a computer and trust the computer because of the way the computer's brain works.
I think [a] couple of other things to pull on. AI can generate a business plan in minutes. I was going to ask you if that worries you or excites you, but I think you actually answered that on some level, which is there's opportunity within that, because when the barrier to creating the plan basically drops to zero, then the quality of the entrepreneurial thinking has to actually rise and I think that is where your company helps.
Did you want to talk about that perhaps in the context of where you're pivoting the company?
[00:27:28] Sabrina Parsons: Yep. Yep, and you're exactly right. And again, it's interesting because we can look back and I can point to things that used to happen that I feel mirror what's happening today with just this different technology, right?
Sure, it can create the business plan in minutes. Is it your plan? Is it right? Do you understand it? At the end of the day, you're going to get funding, even if it's a bank loan, right? Let's say it is an investor because LivePlan, we've had over a million customers and more than a billion dollars has been funded to LivePlan customers. We've had people get fifty million dollars of funding and five thousand dollars of funding. You're going to the VC, you're going to the banker, they're gonna ask you questions, right? It isn't just, "Oh, I'm gonna read the plan and believe it." That's never been the process.
They're going to say, "Okay, I got your plan, now let's go through it. Why do you think you can make this revenue?" And you're going to have to answer it and back it up. You're going to have to say, "I've got the market research. I've talked to customers. I did a bottom-up forecast, and this is what I thought about."
If you didn't think about it at all, like they're gonna know, right? And so, there's that aspect of we always want shortcuts. I don't want to do the reading, I don't wanna do the homework, right? Cliffs Notes have existed for, you know, a long time, and yet at the end of the day, the good students don't use Cliffs Notes because they're going to get bad grades and they're not going to learn.
So, that comes back to our opportunity to help people through this process where, at the end of it, they actually know their business and they can answer questions. And whether you are going to an investor or not, because you know your business, you're making better decisions.
We have, for the longest time, we've always said it, we have five hundred sample business plans and there are people who go to our website and download the sample plan and then search, replace, and change everything, and they turn it in either because they're a student or they're going to a bank loan. And more often than not, it does nothing for them because it's not their plan. That's what you're getting on AI if you just tell it to spit out a business plan. It's really as if you're buying the term paper.
[00:29:47] Jason Rudman: Yeah. I think we've mentioned understanding of the mechanics of how a business works. and what you've just outlined for us is this combination of solutions and tools, but that you do need a human capability to be able to interpret and represent. And at the end of the day, systems will see through that which is just purely built by AI that has no grounding or no foundation to it.
[00:30:12] Sabrina Parsons: And at the end of the day too, I will say the goal that most people have, and this is what they forget, they get lost along the way. The goal at the end of the day is to run a successful business. So why are we taking the wrong shortcuts, right?
Why don't we actually engage and understand? And I get it; everybody wants to do things faster. And, you know, Live Plan is a lot faster today than it was three years ago because it does have AI built in, but you still need to do the work if you want to have the more successful business in the same way that a student needs to read the book if they want to have true understanding of those themes and able to actually write the essay and come away having learned something.
[00:31:02] Jason Rudman: So as CEO, how are you thinking about AI's impact on your own team and operations? And not just LivePlan, the product you sell, but how the company actually itself runs,?
We talked about culture earlier. Are there changes you're making internally that you can share? And are there places where you're deliberately choosing not to automate because to automate would culturally upend what you're trying to create?
[00:31:24] Sabrina Parsons: I will say one of the places we have not automated is we are not using AI chatbots for support. And at some point we'll probably use them for things like forgot my password, very technical support.
But at this point, when people are using our product, a lot of times there's a lot of stress. Starting a business is very stressful. People have a lot of hopes and a lot of fears and emotions, and the fact that they can talk to real people in the chat and get real human answers has been a differentiator for us, and it's very important.
So, that's one example of a place where we could do some AI. We haven't. We will at some point. But right now, a lot of the chatbots are just not there, and people get very aggravated with them.
We've also never outsourced our support. So all of our customer support sits right outside of my office on purpose. I often jump up and help because I can hear what's going on, which I love to do. That is in our DNA, so that's a place we have not.
But, in creating help documentation and new feature tutorials and how we support from a documentation point of view, we absolutely have a few people on our customer advocate team that have used Claude Skills, and we have a new feature and they can plug it into the Claude Skills and get support articles that are really in the right tone and the exact format that we want because we've built these skills and, [in] those places, it's like a no-brainer.
We still have the person then reading through, making sure, does this make sense. So, there is still a human check and a human element, but these are the places where it makes sense. Build those skills. There's no reason not to.
About two and a half years ago, when AI just came out and all of a sudden it was like, "Oh my God, AI," before most people were using it, we began an every other week, two-hour block. Anyone and everyone was invited, and we called it AI School. Initially, it was led by our engineers, but then people who wanted to could bring topics to it, and we just immersed everybody in ‘we have to learn this; we don't know where it's going, but it's going to be a thing and we can't be afraid of it.’
We also told employees "buy the tools, pay the monthly fees. You will get reimbursed." And initially, we also said you don't have to do it just for projects at the office. Use it for home. Use it for personal use. We want you to understand what's out there and how people are using it.
So, we very much embrace just start using the tools and then, two and a half years later, the mission internally is AI should be making your job easier and we should be able to do things faster. It's not going to replace your job. It just means, and we're a small company, that we can get more done. And we've seen that.
The number of features we've been able to release and market in the last year is probably three x the previous year.
[00:34:52] Jason Rudman: I had a connection yesterday with a large part of the member-facing team of BECU. And I said to them that AI is about doing more with the same. The more being you can do more, the same being the same people that are here as we actually upskill and encourage you to use it. We're a larger company than you but that premise that this is about more with the same, it resonated.
And so I’m wholeheartedly aligned with what this is a force multiplier for and that we still need human beings with informed perspectives at the end of the line.
I would love to make a pivot to your leadership, your engagement in community and the bigger picture here.
You're deeply embedded in the civic infrastructure of your state. You've been very vocal about the funding gap for women entrepreneurs. M
Where do you see that we're making progress? And oh, that was a heavy sigh. And where are we still stuck?
[00:35:48] Sabrina Parsons: Oh, boy. It is a heavy sigh because I am Gen X. I am the generation that was brought up with just this fabulous women's liberation movement, right?
Gloria Steinem like, I mean, it just was so empowering. I am also of the generation of you can be Superwoman, which turns out you can't, and that was a little bit of a false promise and false promise, right? You can't do everything and do it all. That's not reality.
And I am of the generation where it wasn't about, wait, how do we facilitate and understand women and how they might do things differently? It was about learn to be successful in a man's world. That's what it was about.
It wasn't… what does it mean to be a woman entrepreneur? It was… how are you successful being a woman in a man's world? Dress like this, pitch like this, ask for this, get a man to be on your team if you're gonna be pitching, right? That was the way I was brought up.
I think I fully embraced the idea that women can do it all. I was like, "Yep, I'm gonna be Superwoman." And then I had a baby, and I was like, "Whoa. You can't actually do that."
And I did begin to embrace a different philosophy and one that really said, "No, I'm gonna do things my way, and that's going to be different.”
And, I am lucky enough to run my own business, so I can do that. I moved into really mentoring women and saying, "Unfortunately, in this day and age, you have to win the boss lottery." And if you win the boss lottery, and your boss understands that you can be super smart and super productive, but that productivity might look differently when you have a one-year-old baby versus a twenty two year old versus no kids… unfortunately, I feel like we're still there, that we still are in a place where we've done some good things.
There's been some advancement, but you look at the numbers, and we just haven't moved the needle much. We just haven't.
[00:38:08] Jason Rudman: Okay. I think that honest perspective is synonymous with a number of women entrepreneurs that we've had on the podcast, whether it be nobody would see me unless my CTO or my COO was a man in the room, like the VCs wouldn't entertain it. It is harder, right?
I think it's about one percent of funding goes to women entrepreneurs still in 2026. And so, the thread I want to pull here is maybe get a little bit more personal if you're open?
So you're raising three sons. You've written publicly as the “Mommy CEO”…
[00:38:39] Sabrina Parsons: Yeah. Yep.
[00:38:40] Jason Rudman: What has that given you? And then what has that transparency would you say cost you?
[00:38:48] Sabrina Parsons: Huh, that's... That second question is really interesting.
I think what it's given me, it's been really interesting. I am one of four girls. So I have three sisters, so I grew up with all these women. It's a silly thing to have thought, "Oh, I'm gonna have girls just because I grew up with girls." That's not how biology works. It just isn't.
[00:39:10] Jason Rudman: That clearly didn't work out, right? No..
[00:39:13] Sabrina Parsons: No. Three children later, all boys. I still feel I think that I have this very one-to-one hands on ability to effect change in these boys who will turn into men.
That is my responsibility raising boys to help them see that different point of view, to help them understand, and for it just to become something that they just hear. And I'll give you an example.
All my boys ski raced. At ski races, for whatever the reason, I don't know why, but ski races would be Saturdays and Sundays. We live in the Northwest. The states are all geographically very big. You drive many, many hours for ski races. So you will drive ten hours and, ski race Saturday and Sunday afternoon, you have to drive back the ten hours. And girls always raced first on Sundays, always. All the way from when my kids were six to they were seventeen and racing.
And, when they were younger and old enough to be like, "That's not fair, the girls all get to leave at noon, and we always have to stay till four o’clock because they race first, and then the course has to be reset, and then we race. Why? That's not fair."
And what my boys always heard from me is, "You know what? Girls for hundreds of years have had to play second fiddle to boys, and so that means we have to leave at four o'clock. You guys need to suck it up and do your part because the world has been in a very different direction for a long time.”
And so I think for me, a lot of what I've done with my boys is to, yes, raise them to be good people, good humans, respectful, consent, all of that, but to also recognize the way things are skewed for men and women, and to own it and be a part of the solution.
Don't complain that the girls are first. Be glad that girls are ski racing and support it.
[00:41:27] Jason Rudman: Yes. My word. My husband and I are raising two mixed race kids and so our son is actually fair-skinned, right? And his sister is darker-skinned.
And we have had the conversation of, exactly where you went, which is doors will be opened for you based on your gender and based on how you present. Your responsibility is to make sure that door stays open for your sister or indeed, let her go first, right?
[00:41:57] Sabrina Parsons: Exactly.
[00:41:58] Jason Rudman: So, from me to you there's an emotional resonance with everything you just described.
You said the second part of my question was an interesting one because you've written publicly about being a mommy CEO and you also talk about integrating family and leadership, which I absolutely agree with.
I asked if the transparency of everything you talked about has actually cost you anything.
[00:42:16] Sabrina Parsons: Yeah. I don't know. I thought about that as I was talking. I don't know If it's personally cost me, because I'm just gonna say that I'm one of those people who is just like, "You know what? If it's cost me something with other people, with other opportunities, I didn't want those people or those opportunities," right?
I am very much one of those who are like, "You know what? I don't need you," and I can suck it up, and I am a strong person, and I can move on with that.
I think for me, it's one of those places where what I really want other women, working women, entrepreneurs, leaders to hear, and I think if we all did this more often, is women apologize a lot for everything. You have people coming from out of town to visit you, and it's raining, and you apologize that it's raining, right?
It is a thing that happens. It is a cultural norm, at least in the United States. And so for me, yes, I'm sure transparency has cost me, and what I say is, "I don't apologize for it. This is who I am. This is who I'm going to be, and you might not like me, and that's okay."
Not everybody is going to like me, and I'm just not going to apologize for who I am, and who I am is someone who will always put my kids and my family first. Absolutely, hands down.
As the CEO business leader, I will always do that, and if people think that means my business maybe could've been bigger, made more money, hired more people, so be it. These are the choices that I've made, and again, as a person who identifies very much as being a mother, I feel like that's what I've taught my kids.
Choices have consequences and that's okay. Make your choices, and that means some people might not like you, and you just need to give them the hand and move on.
[00:44:21] Jason Rudman: I think what you described is incredibly freeing on some level because worrying about what other people think can… I don't think that gets you very far.
So as we close here and, as I reflect on this last question you may have answered it, and if you say, "Hey, I feel like I just answered it," that's fine.
But the podcast, More Elephant, is built on the idea that real change starts with listening. So, in your nearly two decades as CEO, or ‘Mommy CEO,’ I should say, what's the most important thing you've learned by listening, whether to a customer, an employee, or indeed somebody who may have fundamentally disagreed with you?
[00:44:57] Sabrina Parsons: Yeah, that's a great question. I think it comes down to this other question lots of CEOs get asked, right? What's been the hardest challenge as you run a business, what's been the hardest challenge?
And for me, it always comes down to managing people and if you listen to people, that's also part of my philosophy of managing people.
You have to manage people, not employees, and you have to see the whole human. And I have found over the twenty years that really good employees are... you know, you wanna retain them. The longer they're here, the more they have company knowledge. They're here because they're successful. They're here because we have listened to them. They're here because when their spouse was dying of cancer, no one did anything but support them and said, "You go deal with that, and we're not gonna stop paying you because you're gonna come back, and we know that, and you need to be a husband or a wife right now."
During COVID, we had employees with young kids and babies, and that was such a difficult time, and daycares were all of a sudden closed for three weeks, and just understanding and listening and knowing if we listen and we give them this grace, they're gonna come back, and they're gonna be even more loyal, and they're gonna be an even better part of our business.
We have people in our small business here in a tech company who have been with us for twenty five years, and they're not seventy. These are people who are forty who have been with us for twenty years since they were in college and were interns.
So I think that's the biggest thing, is that if you're going to say you're going to listen, you have to be true to that. You have to listen, but you also have to hear what they say, right?
You've got to hear it, and then you have to say, "What am I gonna do with that information, and how am I going to actually pave the path with that trust?
If you're gonna trust me to tell me what you need, then I have to give you what you need."
[00:47:08] Jason Rudman: Yeah. I love that. It's not about listening, it's about hearing.
[00:47:12] Sabrina Parsons: Yeah.
[00:47:13] Jason Rudman: And those are two different things. You have, in the last fifty or so minutes, just given us a perfect outline of purpose, impact and what the work is really all about..
So I want to thank you for spending time with us.
How best to find out more about Sabrina Parsons and the company that you run?
[00:47:33] Sabrina Parsons: Yeah. I would say that check out liveplan.com. We have a unique thing that we do with SaaS software. We have a money-back guarantee. You try the software, you don't like it, we will give you your money back. So I would say check it out and let us know what you think, what you like, what you don't like.
And I will also say email me, sabrina@liveplan.com. I don't mind giving my email address out. I love hearing from people. I love connecting. I find that we as humans and people like to help each other and I'm always happy to hear from someone. And, oftentimes when I help someone two, three years later, we cross paths and they help me.
So yeah, sabrina@liveplan.com.
[00:48:23] Jason Rudman: It's fantastic. So appreciate the time. I'm mesmerized on some level about the journey. And it's given me so much to think about as a leader and as somebody that believes that being involved in community and ultimately trying to build something that's bigger than ourselves is incredibly important.
And, I think you've given me some parental tips as well, unbeknownst perhaps to you. So appreciate your time. Thanks.
[00:48:48] Sabrina Parsons: Thank you.
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