Bob Moesta and Allison Wood: Inside the Mind of an Entrepreneur

Bob Moesta and Allison Wood take a deep, candid dive into her 12‑year journey scaling Da Vinci Education, a SaaS platform spun out from Duke University.

This is a rare, unscripted, deeply human conversation. It covers everything—from intimate personal challenges to strategic business pivots. For software entrepreneurs, it’s not just theory—it’s lived experience shared in real time.

You’ll walk away with tactical insights on leadership, scaling, survival, and reinvention. And you’ll be inspired to lead with boldness, compassion, and clarity of purpose.

In this conversation, Allison discusses:

• Navigating complex co-founder dynamics – she co‑founded the company with her then‑husband, a relationship that evolved from marriage to business partners to divorce.
• Her role of, ‘accidental CEO’, which she grew into the role – learning day by day how to lead, hire, and sell.
• Drawing parallels between parenting and leading a team, Allison underscores the importance of balancing honesty with empathy. Transparency, especially during adversity like layoffs, fosters trust and resilience.
• How crises have prompted focus, eg the pandemic meant her team lost 25% of revenue. By building collaboration features to support remote learning the team was able to build a stronger product.

Allison highlights the themes that have guided her leadership: a beginner’s mind, relentless curiosity, adapting to constant change, and aligning decisions with personal authenticity.

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Transcript

Bob Moesta
I met Allison for the first time today. It might come across that we know each other well, but we just met and this is not rehearsed. I have no idea the questions I’m going to ask, and she has no idea about the answer she’s going to give.

Allison Wood
Set nice, low expectations.

Bob Moesta
Yes, exactly. I’m going to use something I call the time travel interview. This is an interview technique I use to help understand like so I’m going to ask, I want to know through her entrepreneurial career, what would be the one piece of advice she would give her younger self, all the things she knows today.

So how do we distill her whole entrepreneurial career back to what’s the one thing she would have told herself to help her with the journey. That’s what we’re gonna do. So there’s game on and game off. When we go game off, I might ask you guys to help out. So just be wary, or be ready.

Let’s start with Allison. Set the stage, tell us a little bit about you. Where you from? Tell us about the company you’re working with, etc.

Allison Wood
So I grew up in the Midwest, Overland Park, Kansas. And then left, moved to LA, which was where the genesis of this company happened. I have three grown children, 26, 23 and 21 and the company actually is called Da Vinci Education. We offer an enterprise software platform designed to run health science programs like medical schools, nursing schools, dental schools, and we spun out of the School of Medicine at Duke, actually, so built inside the customer.

I think one of the unique things about my story, but also has some universal characteristics, is that I was married to my co-founder, so that is going to probably inform a lot of what we talk about today. The marriage is no longer in existence. He’s no longer with the company. But that’s been a very transformative journey in a lot of ways. So anyway, that’s what got us to Duke.

We were looking for a place to raise our children outside of Los Angeles, and found the opportunity at Duke just to work on a system in house. And I remember him saying, what? Duke School of Medicine is going to hire me? Why would they hire me? And I said, I think you can do this job. And I found the job. So when I think back to the company and the origins of the company, it literally started when I found that job, which was like on Monster or Dice or something. And I like thinking back to this.

Bob Moesta
So did you have the whole idea for the concept? Or the business was already running, and then Duke was your first customer?

Allison Wood
No, no, no. So he has..

Bob Moesta
My job is all this detail between the things you just like, it feels like you went two years.

Allison Wood
I probably did. So this was, we spun the company out 12 years ago. Before that, 2005, my partner had a business background. So he brought a business and systems way of thinking to this opportunity at the School of Medicine, where they were trying to build a solution that could help integrate all the different parts of the educational program. Which in medical schools is much more complex and much more high stakes than a general education program.

So they knew they wanted to kind of build something like that in house, and he knew how to do it from a business perspective. But he didn’t know anything about medical education or teaching or anything like that. So no, he came there. We brought our family to North Carolina, and we’re very grateful that he found a wonderful job at Duke. And he worked there for about five years, until the folks at Duke kind of sat down with us and said, we think other medical schools could use this software too. Why don’t we talk about spinning it out?

So we spun it out in 2011 and I called myself the accidental CEO for a couple of years.

Bob Moesta
How’d the roles break out?

Allison Wood
Oh, good lord. Okay, well, that’s part of the journey. So like I said, he was effectively the CTO. He was the software developer, but he also was the systems administrator. He was the trainer, he was the documentarian. He did the sales calls. I didn’t understand the software. I didn’t know how to talk to these people with all these initials past their names. And so I think I found a lawyer. I set up some meetings, I’m raising our kids in the background, and I kind of stumbled into it. I thought it was exciting to spin this out.

So he worked at Duke for five years, and then we said, Hey, there’s an opportunity here to spin it out. He always wanted to be an entrepreneur. I said, sure, that sounds like fun. And we did it, and I grew into the role. And I have some very key memories of when I finally felt like a CEO.

Bob Moesta
What were those? What were some of those?

Allison Wood
The first one was we had committed to, we probably had about five, we ended up with 10 University clients, and it was him and me, which means it was mostly him, right? And that was nuts.

But one school had big project managers, and everything was on SharePoint. And they wanted to meet with us 50 times a week and we had put all these milestones into the contract for like, $7.50 or something ridiculous. And we kept having these meetings, and I could see him. He kept getting beaten down because they’re like, Well, what about this? What about this? Is this fixed? When is this going to be done? And he’s one guy, and we didn’t really want to tell them that we just had one guy.

So at the end of a particularly strenuous meeting, I got on the phone with the project manager, and she said to me, Allison, can you do this? Can you all do this? What you’ve told us you can do? And I said, No, we can’t. And I said, I hate to say that to you, and I know you’re disappointed to hear it, but I have to be honest with you. And as soon as I said it, I felt so liberated and so liberated on behalf of my partner and I said it, and then I told him, I said it, and I said just told her, we can’t do it. And he’s like, oh, okay, so I think he had eyes bigger than his ability, and he’s a very smart man, but I realized what that meant to suffer, you know, the consequences of, first of all, making a decision that we couldn’t live up to, and then secondly, having to have that conversation.

But the freedom and the liberation from the facade, which I really felt was what we were kind of doing at that point that really stuck with me and has served me well, I think so.

Bob Moesta
So what happened after that?

Allison Wood
So, what happened after that? I think perhaps there was a little bit of a different look in his eye about me. I mean, we always had a very respectful relationship. But I think in a lot of ways, as software developers do, love y’all. When you start the product and you start the company, it’s kind of, it can all feel like it’s about you, and I think both of us were not sure of what my place was in that, and I continued to assume more responsibilities. I learned more about the software. I started to be able to have some sales calls. I hired the people that we slowly but surely were able to hire. We never raised any money. I tried that for a while, and we have a small niche market, and in a tough industry education, and so I said, well, let’s just keep doing what we’re doing.

So as we moved on, I like said he wrote the software, and I built the company, and that was a really transformative experience for me.

Bob Moesta
What way?

Allison Wood
Parenting actually was very helpful.

Bob Moesta
In what way?

Allison Wood
In what way? I’m going to try not to suggest that I am infantilizing anybody who’s ever worked with me, but I think it is about the the people in your care, whether they are your children or your employees or your customers deserve candor, but they also deserve comfort and confidence. And there is a time and a place to be super candid, and there is a time and a place to be strategically candid. And at the end of the day, you want the people that you’re working with to feel like you’ve got their back and you know enough of what you’re doing to get you to the next stage. And so I continually reference that with my children as they were growing up. I just kind of thought about the fact that I don’t have to have all the answers. I don’t have to always be right, but it’s my job to be their mother, and it’s my job to lead this company.

And when my ex and I divorced, and we thought we could stay working together for a while, and we tried that. That was 2019, and it just became obvious to me that, it was very difficult decision to make, harder than the divorce was to say, my obligation, really, at this point, is to this – to the clients and the employees of this company. That’s a much bigger, broader scope of responsibility, especially since we had already separated, and we knew we’re on our way to divorce.

And so when he left the company at the end of 2019, I had never planned to run this company by myself in the top position. That’s where I found myself. And I’m like, man, 2019 really sucked as a year and 2020 better be better.

Bob Moesta
And was it?

Allison Wood
I thought it was gonna be it. Didn’t see how it could be any worse. So then we went through a reduction in force. And again, we were a small company, but as a percentage, I think we lost about 25% of our team. We shut our offices down in a heartbeat. As soon as Roy Cooper said, North Carolina is closed, we just left. Everybody went home and then education. I mean, I’m sure many of us took a hit during COVID, but higher education stopped. They just did. They said, we’re not buying anything. And our clients, of course, are medical schools, so they’re trying to send their students out into clinical environments where nobody knows what’s killing you and what’s not killing you. And buying software was the last thing on their minds. So it was a long time, not a year until we..

Bob Moesta
How did you survive it?

Allison Wood
Cutting force made a huge..

Bob Moesta
You still had paying things, just very few new clients.

Allison Wood
We did and the other thing about us that I think is important, I always forget to mention, is our sales cycle is very long, and so we have annual contracts, multi year contracts. So once someone’s paid for the year, it’s not like we’re trying to. People are churning every month or anything like that.

Bob Moesta
They’re not changing quickly either.

Allison Wood
They’re not changing quickly either. Yeah, so although we did have some schools just say, I’m sorry. I know you’re in our budget, but we can’t pay you. So we lost about $700,000 in revenue that year, I think too. But we kept on and we just doubled down. We said, well, what do we have? What can we do all of our schools, for example, we’re going to remote, and a lot of them, though, we’re not equipped to do that. And so we said, Okay, we have a discussion board function in our software. Let’s just pour a bunch of love into that, right? Let’s make sure that they have the tools to communicate with their students and they really appreciated that. So we worked with what we had.

Bob Moesta
You found what you could within the realm of what was possible.

Allison Wood
We absolutely did. Yeah, we absolutely did, and that helped us. I think it was also very galvanizing and focusing in a way for us. Because I also had to continually remind myself, my team is going home every night, and they’re worried about their spouse and their kids and their grandparents and themselves, and I tend to be somebody who blasts through challenges. And I really had to remind myself that that’s not the way everyone approaches, especially challenges that we’ve never seen before. And we stuck to it. I had the most amazing team ever.

Bob Moesta
So tell me about an investor. You got an investor, and you’re now not the CEO. So you were the CEO for 13 years?

Allison Wood
I was the CEO for, yeah, 12 years. And we sold to a private equity company this spring, and which I’m very, very happy about.

Bob Moesta
I see the smile on her face.

Allison Wood
Thank you. It was part of a strategic merger with our largest competitor in our space. So I’m excited about it, because this PE firm has a focus in our sector. I believe that we all share a very common vision toward what we can do together. And to me, it’s kind of, I’m looking at my little company now and saying, Wow, I think we have the opportunity to really make the kind of impact that I always thought we could so..

Bob Moesta
Did they come to you? Or did you find them?

Allison Wood
Kind of, simultaneously, I have a number of conversations going on, and then these folks came to me, and they kind of stood out from the beginning.

Bob Moesta
Was it time or or were you not looking to sell?

Allison Wood
We had sort of made a decision to shift what our product was doing. We kind of were ready for our platform to emerge into something, more kind of along the lines of data analytics. And so I was going out to raise money to do that, and then these folks came up, and this is a different kind of a growth path, and it turned out to be exactly the right one.

Bob Moesta
So were you excited to basically move on, or were you sad?

Allison Wood
Well, I’m still with the company, so I’m happy about that. And my role is, I’m kind of a bit of a utility leadership player right now, but I love that, because it’s sort of shaping this new entity, but not having to own every single thing I had to own as a CEO. I am fine.

Bob Moesta
What are you loving the most and what are you missing the most?

Allison Wood
I’m missing or I’m challenged by I think, like, how do I fit? Because, the entrepreneur in me wants to contribute and do stuff. The leader in me wants to be a resource to everybody. The enterprise sales person that I grew to become, which is a quite a good one I will say, wants to help with the new sales people that are coming on. But now we’re bigger, and there are teams, and there are specialized functions. And so the challenge for me is, sometimes, is to keep my mouth shut.

Bob Moesta
They got to learn their way, right?

Allison Wood
They’ve got to learn their way to realize that the world will continue to revolve if I don’t contribute to every conversation. And I tend to not, I don’t know that there’s a lot that I really miss. I tend to follow the model of not really having regrets, per se. I think that I’m very proud of the bulk of the decisions I’ve made.

Bob Moesta
What’s the model of not having regrets?

Allison Wood
So Daniel Pink has written a wonderful book called “The Power of Regret”. And it talks about the four different types of regrets that we tend to have in our lives. And I think they’re like, relational, opportunistic, something about the different things that happen in our lives that we look back and go, Gosh, I wish something different, right? And I try to not, once I’ve made my decision, I try to stick with it.

I think of the quote from Scott McNeilly, who co founded Sun Microsystems. This has been attributed to him through many different circuits. He says “As a CEO, I try not to focus so much on making the right decision, but on making the decision I made right.” And I think that’s how I think about regrets.

It’s like I made that decision right, and what did I do to make it the right decision? And then if I did that from a place of authenticity, then wherever that takes me, the next step I take will also be from a place of authenticity. And that’s another thing that I think has translated to my parenting as well with my children.

Bob Moesta
Awesome. So what do you look forward to doing now that you couldn’t do before?

Allison Wood
I am a writer. Well, we haven’t written anything yet, but I really do believe that there is a book in my story of this journey, and it’s a story of not just the entrepreneurial journey, and not just being married to your co founder and then getting divorced, then the evolution of the company. And I thought of loyalty and betrayal and responsibility and love and forgiveness, and there’s so much that comes up for me, and I did a lot of journaling across those years. And I do, I feel like it’s a book that I need to write. And so that’s at the top of the list.

Bob Moesta
That would be great. What’s the one piece of advice that you would have given yourself the very, very beginning of this journey of getting the thing at Duke that you would, now that I’m gonna give you the time machine to go back. And literally provide you one little, small piece of advice.

Allison Wood
Well, aside from, don’t try to start a business with your partner – I think that’s a universal truth, probably, and there was a lot of, there’s long clarity.

Bob Moesta
There’s a lot of hope with that one, it usually doesn’t.

Allison Wood
But I think, and in this is funny, because I’ve thought about this and talked about this with my daughter, actually. I think it would be two words and I would say, be bold. And I think I come across now as a fairly confident, non-afraid person. But I used to think I was shy or cautious, or maybe even a little anti social. And I think what it really meant was I have a ton of passion in me and I am this 1000 watt light bulb, and I held that back. And I don’t know if that was the generation I grew up in, coming from the Midwest, and all sorts of nature reasons you can cite, but I think be bold and lean into make your decisions from an authentic place and then go all in.

Bob Moesta
So when did the imposter syndrome go away? Do you remember, or is it still there?

Allison Wood
I think everybody has a little bit.

Bob Moesta
We all have a version of it, but like, there’s a point where you felt it kind of dip. When did it dip and why?

Allison Wood
Well, I’ll tell you when it was the worst, was around when COVID hit, and I had not been transparent with my leadership team about financials. I just, I don’t think I felt comfortable with the financials exactly with the business. And so everything had to be on the table. And I was like, oh, man, what have I done now? They’re going to see that I just don’t belong in this seat at all. And of course, that wasn’t the outcome. And so, again, opening that up and leaning into it was great. And then I think we had a banner year in 2022, and but I think really, everything that happened after COVID was continually me feeling like, Yeah, I think I belong here. And I love leadership. I don’t always love managing people, but I love leadership and just kind of waking up every day, really, with that a sense of gratitude about that. And what a gift, what a privilege I have to be able to do something that I enjoy, that’s challenging, that’s hard that doesn’t always go well, and I get to do it again tomorrow.

Bob Moesta
That’s when you know you’re doing the work that you love.

Allison Wood
Yeah, absolutely.

Q&A

Bob Moesta
Can we open it up to the floor for questions? So you have somebody who’s been through the journey that you are all on. So my question is that you have somebody who’s on the other side ask some questions, because at some point in time, I know you don’t really know the question to ask, but the fact is you need to know what this journey is like.

Audience Member
First of all, thank you. Do you think if you’d gone back and told yourself two words be bold, that your old self would have listened? And if not, would that change your advice?

Allison Wood
That’s kind of like that’s sort of circular, isn’t? It’s a little bit of an inception question. I would hope she would have been wise enough to listen. But sometimes I think, wow, what would my pathway might have been totally different, right? Totally different. I wanted to write when I lived in LA. I wanted to write for television. I tried doing that for a while, and who knows.

Bob Moesta
But even if it’s not the same, the reality is, be bold. Be bold, right? Bolder, do whatever you want. It’s great advice to everybody, just to be a little bolder. It is everything you do.

Allison Wood
It is, and I will say this, I love my mother to death, but I think my mom was one of those ones who would say, Oh, you love the theater. We can’t really make a living at it. Why don’t you get, what’s your backup degree going to be writer?

Bob Moesta
And that’s a Midwest thing, by the way.

Allison Wood
Total Midwest thing. But I think it also it makes you sort of doubt yourself a little bit. I really believe that we live up to the expectations that others have of us, and I think it’s good to push and I think it’s good to say, yeah, that’s hard. You might not make that, right? Have a growth mindset. You’re doing well because you’re trying hard as compared to you’re doing well because you’re so smart. The day that you aren’t so smart at something, then you feel like you kind of are crumbling so. Because of that upbringing, I think I probably would not have embraced that. And I think there’s also something to be said for being in the era of life that Bob and I are in, which is you’re like, yeah, just go do it. Life is too short not to.

Audience Member
Allison, you’ve had quite a journey of ups and downs. You had all that personal entanglement with the business, how did you stay optimistic through probably a very emotional question period of your life?

Allison Wood
That is a great question, and I think it’s probably two things. One is naive naivete. I just want to do this. I want to I don’t want to fail. That was part of it. And I also, like I said, I didn’t really know exactly what I was doing in the early years, especially.

I think the other thing was, because we were married and we had three children, and this was our way of supporting our children, failure was not an option, it just wasn’t. And I am an optimistic person, though, by nature. And again, the older I’ve gotten, and the more you turn optimism and gratitude, and you blend those two things together. And you start to learn that maybe you’re not this path that you’re on isn’t going to work out exactly this way. But hopefully, you have intelligence and connections and there’s other things you can do. So you tend to widen your lens. I think a little bit is also a good way to stay optimistic.

Bob Moesta
I had a mentor named Dr Taguchi, who reminded me every single day that, and didn’t understand when he said it, but I understand it perfectly now, which is, there’s way more unknown than there is known, and never forget it. And the reality is, whatever I learned yesterday doesn’t mean it’s applicable today, and you have to constantly be curious and learning all the time, because at some point in time, that’s what this is all about, is learning.

Allison Wood
Yeah, 100% it’s important to keep a beginner’s mind, and that’s an uncomfortable place for me to be. I like being good at things, so that’s a really good reminder.

Audience Member
Thank you very much. Allison and everybody here, what was the most surprising thing for you on this journey, and what are you most proud of having gone through it, being in someone on the other side now?

Allison Wood
I think the most surprising thing for me is how, like said, how authentic I feel like this is what I’m supposed to be doing right? Or I was supposed to be doing was leading – leading my family, leading this company.

And then what was the other part of your question? What I’m most proud of is how I led – with compassion, with candor, commitment. And it’s not that, I didn’t like hurting people like my ex husband and by extension, our children when we got divorced, but I feel like there was a clarity to my actions that almost came from outside me. And I followed it and I honored it, and I’m very proud and grateful for that.

Thank you, all.

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