The Art of Being Number Two: Insights from Fractional COO, Ginny Wood | Peter Lohmann's Podcast
In this episode of Peter Lohmann's podcast, Ginny Wood shares her unconventional career path—from programming mainframes in COBOL to becoming a fractional Chief Operating Officer (COO) for PropTech and SaaS companies. She explains how early technical training shaped her data‑driven mindset, and how a 12‑to‑18‑month sabbatical for a full‑stack bootcamp reignited her love for software and led to a series of fractional COO roles, including a stint at LeadSimple. Ginny emphasizes the importance of deliberately choosing the people you work with, taking responsibility for your choices, and fostering an environment where team members can request what they need. She outlines her diagnostic approach when stepping into a new organization: start with financials, identify revenue vs. expense issues, track churn, and implement early operational reporting and forecasting to surface problems before financials do. Ginny discusses leadership communication, drawing on Nonviolent Communication and the Hoffman Process, and stresses confronting conflict directly rather than avoiding it. She shares personal challenges, such as caring for a sister with glioblastoma, and how she uses gratitude, breathing, and self‑care rituals to quiet her inner critic. The conversation also covers the relevance of EOS and its derivatives, the different flavors of integrator/COO roles, and practical advice for property‑management leaders about burnout, automation, and hiring the right COO. Throughout, Ginny balances a warm, supportive tone with candid, self‑reflective honesty.
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My orientation is that I claim responsibility for all of my choices and I choose my people and I, it is vital to my wellbeing that I'm around great people and because that is That is my environment for 8, 10 hours a day, whether it's work people, home people, a partner. You know, I, I get to choose who I'm with, and as a leader, I choose those people. And so somebody said to me once, what is the number one predict factor of divorce. And it's like, well, what? And is it choosing the right partner? Like, just choosing the right people?
Welcome back to Peter Lohmann's podcast. I'm so happy today to introduce Jenny Wood. Jenny, thanks for coming on the show.
Oh, it's my pleasure.
It's really fun to have you here. So Jenny, before we jump into a bunch of really interesting questions that I've been wanting to ask you for a while, actually, why don't we start by just having you give like a 3-minute background yourself, just so the audience is kind of familiar with who you are and your journey?
I started my career, it Being a programmer, actually. And back then it was not a software engineer, it was actually called a programmer. And I programmed mainframes, so that—
Wow.
Will date me. I programmed in COBOL, and I didn't think I wanted to be in a cleaning closet on projects for the rest of my life, which is what was happening, so—
It wasn't glamorous back then.
No, no.
And so—
No, correct. And so I was with a large telecom company and was drafted into corporate finance and worked my way up there and out into marketing and out into sales and back into marketing. And then as that company was stalled because it was being acquired, I just got bored and pushed myself out into a $300 million KKR company. That was wrestling with whether they should take their business online, and they were getting their lunch eaten in print. And took on a strategy role and then got the business funded internally by actually Henry Kravis. And so I was an intrapreneur and partnered with a really outstanding person who was more out in front and I just got the phones up and running and it was what ended up being the value of the company when it sold. Hmm. Because print was no longer and everything was on the web and, and it was actually apartmentguide.com.
So, oh wow.
And newhomesguide.com. So, you know, that's when I started. I, I've been in, you know, interfacing with property managers earlier in my career in kind of early, you know, web 1.0.
Yeah.
And I decided I really liked that number 2 role, building stuff internally and then someone else out front being the face of it. And I really like to hire people, lead people, developed a business model. Work with clients and, you know, did that over the course of, you know, after that, after 2008 when, when I left that company and did some 5, 7-year stints, one in healthcare data company. That was incredibly useful because I got to lead PhD kind of data science stats type of people, so learned a lot about data and probably, you know, had the best— the person who taught me how to do voice of the customer and product development best. And that was incredibly useful. I was also part of a software venture capital firm, an entrepreneur in residence, where I would take seedlings and push them up over the fence. And it was a dev-for-equity model. And so, I was one of the only business people in there with a bunch of software engineers. And at that time, I learned that my software engineering skills were so old and not contemporary that I was not adding value to a product development business engineering relationship. I just found myself being impatient and wondering why they couldn't get things done. And so I decided—
You're like, I could program this in COBOL faster than you.
It's like, come on, what's wrong?
Yeah.
And which is not helpful. It's not great leadership to be tapping your toe and wondering why people can't get stuff done. And I knew that I loved software and SaaS. And so I took a 6-month sabbatical and I went to full stack development school in San Francisco. So 12 hours a day, 6 days a week.
Whoa.
And learned it. And I was the only— I did very well, and I was the only— I was oldest by far person in my class. I, I, I— one of the unanticipated benefits of doing that was to work with 23-year-olds and realize that they didn't want a boss. So, you know, the old paradigm of leadership was absolutely gone. And it was really good for me to be a peer with other learning, you know, developing software engineers who are 23 to figure out how do I lead informally in this environment. And that was a real blessing. So, out of that, then I started doing fractional COO work for tech companies, mostly on the earlier stage, you know, some later, like, you know, did a $200 million company. And as I was doing it, I was pinged by Jordan from LeadSimple and was their fractional COO for a period of time and decided that this was the best group of people I'd ever worked with. And why wouldn't I wanna do more of this?
Mm-hmm.
And so joined the company late in 2023 as COO and then left at the end of December '24. So just recently. Yeah. My sister, who's just a year and a half older than me, was diagnosed with a glioblastoma, which is incurable brain cancer. Mm-hmm. And so I'm just, taking a moment, pausing, and just being with her, staying flexible so I can really enjoy the precious last part of her life. It's really— I'm so grateful. It's a gift.
Yeah, that's a really inspiring story. I, I knew a little bit of that just from you and I chatting here and there through our LeadSimple connection, but fascinating to hear about your early experience with programming. How did that inform the way you think about business relationships? I find that people who pick up programming pretty quickly tend to bring a certain way of thinking wherever they go. And those who can combine that with business skills and business sense are just always rock stars in my experience.
It definitely, it honed my logic skills and developed kind of a construction thought process, how to put something together. It improved my math skills. So, you know, I, I think it made me data-driven. And then when I worked with a lot of database engineers and PhDs in stats, I could meet them on that work. And because we were developing data products, I could think like the business person, but offer suggestions and ideas.
Yeah.
So, it, it helps me generate ideas and kind of geek out with technical people, which enhances the relationship. I mean, it, it, it's the bridge. So going back and doing that in 2017 allowed me to build another bridge so I could understand what they're doing and, and offer ideas, um, for scaling improvement. So it's pretty fun. I think that more people, uh, people could really do it if they want. And I'll tell you, I'm thrilled. I've just been messing around with some of the AI tools. It is awesome.
Yeah.
My daughter and I were just playing with something and, you know, kind of got a baby prototype working.
Nice.
You know, just, it, it's a, it's an exciting time.
Yeah.
I'm, I'm really interested to see, you know, how does a software engineer have to think at a higher level, uh, or get to think at a higher level in order, you know, with the current tools.
Yeah, I think we're all feeling similar, like there's just, it's a new frontier and it's a really, really exciting time to be in it. So it's really cool. So I want to ask, start by asking about your time as a fractional COO or your time at a couple different companies as a fractional COO. I know that you have a lot of experience with EOS and I've got some, some questions there. When you get involved with a company, you know, in this fractional COO basis or in general, when you step into an existing company in a leadership role, how do you know where to get started going to work? Because I feel like the founders or whoever is bringing you on, they probably have these ideas about, well, you really need to start over here because there's an issue over there, right? And I have this intuition that when you actually get involved, It may not actually be what they thought it was. There could be like a deeper level or something else going on there. What do you, how do you decide where to start? Because to me, the idea, because I've had people before say like, oh, you should help us here or get involved. And frankly, I find the idea completely overwhelming to step in midstream to an operating business and try and figure out where the problems are or where the opportunities are.
I start with the financials and it tells me 75% of what I need to know. So how viable are we right now and how many resources, how, you know, money is a resource. What, what do we have to invest here? So that's, you know, how, how are we doing? And then So on the, on the bottom line, you, you know, but also, you know, is it a revenue problem? Is it an expense problem? Where, where is the challenge? And you look at your revenue generation patterns. I look at the revenue generation and, and then, and I look at things like churn and that tells us where we, uh, people opportunity. So Then, you know, I look at how are people measured? You know, who do we have and how are they measured? And we might have really great people who just haven't been asked to show what they can do and, and report in on and forecast. So, so then I implement that, implement operational reporting earlier, early indicators, something earlier than what the financials show you because that is way too late.
Yeah.
And then we start asking leaders to forecast. So when you call your shot, how right are you and how consistent can you deliver that? And that tells you kind of the level of maturity of your leaders. And you can do that with individual contributors too. It's, you know, and all of those metrics should roll up to the company metrics, the metrics that power the business. So they shouldn't be disconnected from the 5 most important things. So that we start stress testing leaders, you know, for a product development or engineering team, it could be on, you know, on-time delivery, value in the market. For customer service, it's, you know, CSAT, churn. The churn's way late though, too late. But then we start having conversations about, well, what's needed to grow the business. And are you, do you want to do that? And are you able to do that? And those are really direct, healthy, heartful conversations. And, you know, there's nothing worse than being in a role that you don't want to do or you're not good at. And, you know, I've been there myself for sure.
Mm-hmm.
Just miscast. And so from there, then make sure, get the right leaders in place and then make sure that they understand how to hire great people. So I think there's a book called Who Not How. Yeah. Is that, is that a book?
It's up on my shelf somewhere here.
Oh, okay. Well, that's it. You know, my role is to create, make sure that the business model's solid. That we have great leaders in place, that I bring an encouraging, positive approach to everything we do, and then, you know, don't hold back on really on things that need to be said. And, and I'm— and encourage that to come my way too, because I'm not done growing. And then measure everything to see what's working, what's not, so we can pivot quickly.
Today's episode is brought to you by my friend Julian Calvo. Before we get back to my conversation with Jenny, I want to take a moment on a topic that every property management leader knows well, and that's burnout. We all see it. Teams working late, juggling emails, texts, and tasks that live in 10 different places. It wears people down and limits growth. This is why I want to highlight someone you may already know, Julian Calvo over at LeadSimple. Julian worked directly with Ginny when she was COO, which says a lot. He helps property management companies put structure in place so the business can run without people burning out. Julian and I recently recorded a conversation on burnout where we broke down what really causes it in this industry and what leaders can do about it. I'm sharing the link to that video in the episode description, and I encourage you to check it out. If you want to act towards reducing or avoiding burnout, I've also included a link so you can book time directly with Julian. He's going to walk you through how you can reduce burnout in your own company while helping your team operate with clarity and confidence. Let me just interject here a personal comment. My team at RO Property Management uses LeadSimple. It does help them avoid burnout, and it's a huge part of what allows me to take a month off from my business every year. Both links are in the description, the conversation on burnout and a direct link to Julian's calendar where you can chat with him. Now let's get back to Jenny. That was awesome. And it reminded me of a lot of what I got to see at LeadSimple during your time there. And I also was totally sensing the programmer background, right? You know, show me the numbers. Right. Everyone needs metrics. Jenny, I've always noticed about you that you have this, like, you're super clear-eyed on what matters and you have like a way of not compromising in those areas, but you have a warm approach at the same time, which is, I find rare. I find that people who have this warm way about them are soft on like the things that matter to me as an engineer, like the numbers or performance, right? And then people who are too far the other way, like they don't bring that warmth or they don't bring that people-oriented, people-first, it's probably a better way to say that, way of relating to the problem. So, and that's exactly what I was hoping to tease out a little bit more because I think it's so effective and it's not, it's not something I hear talked about a lot on the business podcasts. And it's hard to articulate. You're hearing me struggle with it a little bit, but I hope that listeners got a little taste of it just there and hearing you describe your, your approach when you come into a company. Taking you back to something you said earlier, which I really like, you said tapping your toe and saying like getting frustrated that people can't get stuff done faster. You said that's not a good leadership model. And I find that business owners that is their experience, right? They're, they tend to be visionaries. They tend to be hard charging. They tend to be fast and they get frustrated with their teams when they're not able to get things done quickly. So if that's not a good approach, what then should we do when we see an important objective or target or number that we need to hit and we feel like the team isn't, isn't getting after it the way we feel like we would be doing?
My orientation is that I claim responsibility for all of my choices, and I choose my people, and I— it is vital to my well-being that I'm around great people. And because that is, that is my environment for 8, 10 hours a day, whether it's work people, home people, a partner, you know, I get to choose who I'm with. And as a leader, I choose those people. And so somebody said to me once, What is the number one predictor of divorce? And it's like, well, what? And it is choosing the right partner.
Mm-hmm.
Like just choosing the right people. And so that, uh, that's completely within, that's my responsibility to choose good people. And then to give them what they need and to create an environment where they ask for what they need too. And with that dialogue, I mean, like, like you're all in it together. So there's no difference between your result is if you're on my team, your result is my result.
Mm-hmm.
It's our result. But I can't distance myself from that. And then if we can't create that together, then we should not work together.
I totally agree with you. What I feel like the pushback to that would be, if I put myself like as someone who's working for you, wouldn't the person just say something like, well, that's all great, Gini, and that all sounds wonderful, but you're about to go off to your fun leadership meetings and I'm over here actually having to do the work. And so when you say we're in this together, how are we actually in this together? Because I actually have to do the work.
Well, I would ask you, is there a request?
Hmm. Yeah, I like that question.
Is there something you need? Mm-hmm.
It's kind of like you're almost like forcing agency on the person, right?
Yes. And if there was, then I would dig into if there was no request, an unexpressed request that, and we all have trouble sometimes identifying what we want or need. I would share that I experienced some, ask if there's some resentment. You know, you go off to your leadership team meeting and I have to do all the work. And I would ask, are you feeling resentful? So Peter, are you feeling resentful?
Yeah, I think I am feeling resentful. I feel like when things go great, you guys take the credit. When things aren't going well, it's like, hey, why aren't you guys getting this done? And, you know.
Got it. Is there a way I've shown up that would have created that experience for you?
I don't know.
I'm open to hearing that.
Have you, have you read this book called Nonviolent Communication? Yeah, I'm just picking up on a little bit of that. I just finished watching— the author's got some really interesting lectures on YouTube. I just watched like a 3-hour lecture of his, and some of that language is very familiar.
Well, I think I, I read it so long ago, but what I'm doing right now is I'm just here with you. Mhm. And one thing else I would want to know, if you didn't have any requests or, or feedback for me, is whether you're filling your own cup. Because my experience is for myself is I, I feel resentful when I am not getting enough sleep, exercise, the things that I need, and I've given too much, not out of my overflow, but out of my essence. And so I would just ask about that. If there's— are you being, are you giving yourself what you need? Are you giving from, you know, are you running on fumes here and then trying to give it to me? Because that won't really work.
Yeah, that was a really cool, interesting phrase that you used, the giving out of your overflow versus giving out of your essence. It conjures up a really clear image for me of like giving to a team, a company, a partner, out of a feeling of wanting to see it succeed versus a sense of horrible duty and obligation that's like taking from your soul because you're just—
you feel like you have to, or because you're trying to please, or you're trying to get approval, or like, you know, because I couldn't— you know, I, I can't give you all the approval you need. It's like I'm never going to validate you enough, you know. So, so you could try for me.
I don't know, it could be fun.
So you got to fill yourself up in whatever way, you know. If you have to go play pickleball or play with your kids or sleep or cook, you know, like, we're not meant to work all the time.
Yeah, so good. And that leads right into something I wanted to ask you about. So I was kind of reviewing your LinkedIn resume leading up to this interview and you even mentioned it. You said that you took a sabbatical and during that time you went to this coding bootcamp. This idea of a sabbatical is something you— it's like very commonplace in certain domains, academia. It's in, you see it in like a couple other small segments. Or, but it's not a common thing, at least in the circles I run in. And I want to hear from you more about like, where did you even get the idea to do that? And, and you took like, I mean, I'd call my little month off like a mini sabbatical, but you took a significant, a real one. How long was it?
12 to 18 months. Yeah, 12 months at least.
I'd love to hear like where you got that idea, what it was like. Would you recommend it? It's just very interesting to me.
Yeah. Well, I had a little bit of savings and I was so glad that I did that because I knew I wanted to learn some new things and just rest a little bit and watch the flowers grow and stare at a tree and see my kids before they graduated from high school. So it was more like, no, this, like, you know, I'd been working at that point, I'd been working 25 years, and I just needed to learn something new and take a moment and redecide what I wanted to do.
Yeah.
And I didn't start again until I was clear. And I found a way to live on very little. And so it really was regenerative. And, you know, I'm doing that right now for a different reason, but there are times, I think, when your body and your heart tell you it's just, you, you need to stop for a minute. Mm-hmm. And I think it's important. It's been important for me to pay attention to that so I don't end up with like a back that hurts or weird, you know, ailments in my body. I think, you know, people start, it, it has to start hurting your body if you're not doing something that helps you thrive.
Yeah.
So, for me, it was mostly a learning sabbatical, but then it was like, okay, what do I want to redo and what do I want to do differently? And I knew I loved this COO role and I knew that I really loved sprinting. So, I gave myself, and it was even before people called it fractional COO, there wasn't even a name for that, or fractional integrator. I, it's like, I just really like doing this.
Yeah.
And, and it was my dirty little secret was that, you know, with so many different types of companies and challenges, I got paid to learn and it was incredible. So, so I, I, if I hadn't stopped, I'd be, I don't know, probably have some big company, which wouldn't be terrible.
Yeah.
But I'd probably be really bored and not thriving and not learning.
I find that you have a really effective way of framing things. Like, some people, if they didn't have a job for 18 months, they would— first of all, they would be terrified to even do that. And they would also talk about it as like, I don't know what I'm doing, or I haven't found the right role yet. But when you frame it as, oh, I'm taking a sabbatical, I'm, I'm, I'm investing in myself. I'm, I'm, I'm relaxing and finding what's important for me for the next phase. Right. And then you also said like, you got paid to learn. Other people would call that being terrified every day. Like, just like, don't know what I'm doing. Right. But you're like, no, I'm getting paid to learn. Right. And that's a really I think that's not a, it's not a coincidence that you have a way of framing things that are high agency, high self-confidence. So I really like that.
Well, thank you. I don't, I've never had all the answers. So as I've gone into, I could do that fractional work because I believe other people have the answers and my job is just to ask great questions and help synthesize information and pull it together. So I'd say probably the thing that I was really good at that allowed me to do that was just asking for help and not, not, oh, everybody else do the thing, do, you know, I'm not gonna do any work, but it's, I don't understand. So Let's, can you help me understand? And then, and collect information and then, and make sure we're all looking at the same information and then the answer's obvious. So I never had to know the answer.
Mm-hmm. Yeah. That's a great way to relate to unknowns. Yeah. Speaking of unknowns, you've had a few career shifts. How do you know when it's time to move on to a new phase of your career? Like how— so for example, I've been in professional property management now for 12 years and there's certain benefits that come with spending a lot of time in a certain segment or domain. You really get to know everyone. You have this deep knowledge, you're comfortable. But on the other hand, you can kind of start to get a little boring, right? You just, it's like the same conferences and the same people and the same problems that you're wrestling with. Like, what do you, how do you, how did you tune into signals that were helping you make this decision as you bounced around between a couple, you know, large decisions for career-wise?
I always made the decisions based on the people I got to be with.
Hmm. Interesting.
And it just so happened that I was in PropTech because I wanted to be with these people. And you're one of those people, by the way.
Thank you.
Yeah. I mean, I— there you are, gracious. You're so intelligent and you quietly get shit done and you're generous with your feedback and ideas, not just, you know, hey, I got this idea, like, let me, yeah, I'm gonna let, I'm gonna invest time and elaborate it so it's of value to you. Those, you, people like you are the reason that I chose what I do. And it's, so it's who can I be around that has positive energy, trying to get something good done. You know, property managers, I think I've shared this with you before, have, I think, one of the hardest jobs out there. They're, you know, by the way. Say no more. Well, like they're dealing with people who are doing one of the top 3 most stressful things that happen in their life, moving. Into a new home. So they're dealing with home dwelling. And then on the other side of that, and, and, and they're usually getting people at their, probably their worst.
Yeah, it's also their highest monthly bill.
It's their highest monthly bill. And, and they're, they are at, I know that when I've been in the middle of moving, I'm, I'm definitely not at my best. And then, you know, whatever patterns they have when they move in, things that aren't right, whatever, however someone views the world, property management firm gets all of that. And then on the other side with the, you know, with owners, they're managing potentially their largest asset. So it's, you have my money. What are you doing with my money? You know, so whatever an owner, you know, how— whatever relationship they have to money, property management firm gets that too. And so I— it—
it's—
I chose the people in the industry, and I think serving these people is worthy, and taking automating, taking whatever we can off their plate is so critical so that they, they have— there's a possibility they could— they can be present for connection, which, you know, is— I mean, that's the most rewarding part of work.
I love the idea of choosing what to do next based on who you're going to be with. I saw a great quote I think it was yesterday actually, Alex Hormozi surfaced this for me, but it wasn't his quote. It was something about like, people choose what they want to do in their 20s based on the destination. People choose what they want to do in their 30s based on the journey. People choose what they want to do in their 40s based on the company, like who you're going to be with. Very much aligns with what you were saying there. And I found that to be true for myself as well, but I haven't, I don't know that I've actually surfaced it as like a decision-making tool.
Yeah, who do I get to be with? Who am I doing things for? Is that meaningful? Like, and are we in relationship on this thing that's of value?
Yeah. Today's episode is sponsored by Crane's Access Granted live webinar coming up on September 30th. If you haven't heard of Crane, it's a private community for property management business owners who want freedom of time. I co-founded CRANE with Wolfgang Kroski 2 years ago, and the community has grown very quickly with over 170 members. We only open up twice a year to admit new members, and the next application window opens very soon. Our upcoming Access Granted live event is for current and prospective CRANE members. This is our first ever launch event for CRANE, and we've saved up a ton of exciting news and announcements that will affect everyone in the industry. As part of the event, we're doing a 1-year Crane membership giveaway, which we've never done before. We're also going to be announcing new ways to pay for your Crane membership, the location of the next Crane Horizons retreat, upcoming Crane Unplugged dinners around the country where you can mix and mingle with members, and tons more I can't even talk about yet. If you've ever thought about joining CRANE, this is the event to get your questions answered and learn about all the amazing benefits that members enjoy, some of which end up paying for the membership costs multiple times over. To register for the live event, go to joincrane.co or click the link in the description. See you there. You mentioned working with property managers, so your time, you know, at LeadSimple and other companies. You were around property managers. I wanted to ask you, from the perspective of somebody for whom property managers were a customer, what are our blind spots? Like, as property managers, what should we know about ourselves that might not be obvious from the inside, so to speak?
Well, have you— this is extreme, but have you ever been around police officers as a, you know, more than one?
Not really, no.
So, so the way they see the world, it is, you know, very— it's not optimistic because of what they see on a day-to-day basis. I think it would be really easy to have that wear you down over time, seeing crime, you know, seeing people definitely at their worst. And so I think maybe just, you know, they're overly skeptical because of what they see and receive from others day to day. And—
Oh yeah, my sister's sick. I'm going to get you the rent next week. Yeah.
Yeah. And so, gosh, I mean, if you don't have everything possible automated so you could limit the inter— the negative interactions.
Yeah.
You know, and if you're not on your game and following up and delivering as a property man, you're going to get a lot of negative inter— it will be self-fulfilling. Yeah, for sure. And even if you have everything buttoned up, you're still going to get some of that. But I would say it's, you know, I guess my question would be, are you aware, not you, but is it, would, is a person aware that they are, they think things are happening to them, that they, they can't get ahead and that it's a terrible slog. Because if that is so, then they'll feed that back out.
Yeah, that rings true for me. I think there's definitely, you know, among my, among myself and my peers, there's like the skepticism for sure. There's also this idea that like, if it's not perfect, if the tool's not perfect, it's worthless. I sense that a lot when I step back and I'm, and I'm rational. I realize that often an 80 or 90% solution represents an enormous leap forward for my business, even if every single edge case isn't solved. Yeah. And that's hard because property managers tend to be very, it's like we've, we take refuge in policy and enforcement of processes, because that's the only way we can bring order to our professional life. And so, and we're trained that these things have to be 100%. Like you can't waive late, you can't enforce your late fee 95% of the time, but then waive it for 5% of residents because that could be a fair housing lawsuit. They could say, well, why did you waive it for this type of person and not that type of person? So we're, we're trained of like, it's got to be all or nothing. It has to be complied 100%, has to be perfect. So when we're presented with a tool that's maybe still rough around the edges but demonstrably makes our world better, we're looking at those edge cases, sort of preoccupied with them.
Yeah. And, you know, it's fair because it is an incredibly regulated industry and for good reason, but it makes it really complex to navigate and scary to implement new things sometimes just because you don't, you know, you don't wanna be in trouble. So I get it. And I think, you know, one question I have, what, what are the options? Like, continue to slog through it the hard way, you know? I mean, yeah, you know, that's a choice.
Yeah. Did I read or hear right that you were born and raised in Nebraska? Yeah.
Yes. Yeah, Lincoln, Nebraska. And is best place in the world to grow up, for sure. Mayberry-ish. And then I I loved it so much that when my kids were approaching middle school, moved them here so they could participate and have— be free range.
I spent a little bit of time in Omaha, traveled out there 3 or 4 times for the Berkshire Hathaway shareholders meeting. And the reason I wanted to ask you about this is because I've seen you, Ginni, give very direct feedback. I've seen you have very hard conversations in a very direct way, in a respectful way, having moved from— I grew up on the East Coast, so I grew up in New Jersey where I was no stranger to direct conversations with strangers, friends, anyone was not afraid to have a direct conversation with you in New Jersey. And then when I moved here to the Midwest, I'm here in Ohio, those direct conversations were perceived very differently. And so I'm curious, I don't sense that these sort of direct form of communicating was something you learned in Nebraska, or maybe you did, but I'm curious to hear your journey. Is that a way you've always communicated? Where did you learn it? How did you learn it? I'd be interested in that.
Yeah, there's a thing called Nebraska nice, and I was trained to not have difficult conversations or upset— trained to not upset anyone, which is a crazy As if you could control other people's reactions. And the way—
and this was something you're not saying like you went to a school for this, this is just—
it was in the air, it was in the water, in the air, in my family.
And not for nothing, but that's something women are told sometimes explicitly, right?
Be nice. And yes, and don't make waves. Or so the way that I got to having direct conversations was through experiencing pain. And I found that avoiding any conversation that needs to— I mean, any conversation that takes me away from getting where I want to go, or that's outside of my values, or avoiding that, it has, it has always caused me pain and suffering. For example, you know, not getting the result. You cannot get a result if you don't put it on the table and ask people to look at it and ask if they want to get there with me. So like, that's really the approach that I've taken rather than, you know, confrontational. It's just looking at the thing that we, that I wanna do. Do you wanna do that with me? How are we gonna do that? You know, that, that's really it. But I've found that people, when I have either gone too long without having a conversation about something that's not working for me or that's in our way, it has always resulted in surprise and upset with the other person. And so it's a paradox, like in trying to be nice and avoid conflict, I've always created a huge conflict.
So I think it might've been Jordan who told me once this catchphrase, rush to conflict. I don't know if that was him or— yeah, yeah, this idea of like, don't avoid it, rush toward it if you know it's, it's inevitable.
Yes. And you know, one thing that I've learned more recently, I feel so great, is I am responsible for 100% of my 50%. And the way that you react to it is your 100% of your 50%. And I'm definitely open to how, you know, feedback, how I could do that differently, better. But, but I don't— I'm not responsible for your reaction. I'm only responsible for sharing the way I see it, sharing any facts, sharing my feelings, and then you, you can decide how that is for you. But I think, you know, this, this whole like trying to massage it so that you don't react a certain way has always blown up on me. And people can see it coming.
Yeah.
And, and they, you know, they don't trust me when I do that.
Very interesting. This is— so if you're listening to this and you're like, I need to know more about what Jenny's talking about, highly encourage you to read Nonviolent Communication. A lot of themes running through here. I'm on a journey down this same path. I am not as far along it as you are. I'm learning every day, every week more about how to take— not only take accountability and responsibility for my reactions, but also to not take accountability for other people's reactions and not use that as a reason to not bring something up. This is relevant everywhere in life, you know, your family of origin, your business, peers in the industry, your— obviously your romantic relationships, your kids. I mean, so many domains in which this shows up that it feels like something we should all be taught, like in junior high or something, because—
yes, but we don't really care about people in general.
True.
Maybe that's it. I really do, like, I really do care about— if that— if I'm going into every conversation that I care about you, then, you know, the intent is nothing but positive. It doesn't mean you won't react to me though.
Yeah.
You won't react to something I said. And it could be based on what you had for dinner or that your mother used to say it to you that way. And if I still care for you in every moment, then I can sit and hear what you have to say about that. But, you know, not but, and I'm still looking at, you know, we're trying, you know, I'm trying to get here. This is the vision. How can we get there? And sometimes you just have to take an off-ramp and listen for a minute.
Mm-hmm. Very powerful. So it sounds like a very self-taught and, and, you know, messing up a lot.
Messing up a lot. Yeah, for sure.
I run into people who, you know, it was, they went to like a 2-week-long retreat where this was taught, or they, like, I'm currently, you know, consuming this, this author Marshall, the, you know, the nonviolent communication guy. It's so hard though. It's so hard because it's easy to fall back on the patterns that were modeled for us.
Mm-hmm. Mm-hmm. Yeah. I just went to the Hoffman Process.
Okay.
And it's a 7-day retreat. You know, they don't market— they're nonprofit. It was all about automatic patterns.
Hmm.
And it was a life changer for me to develop strong awareness around what my patterns are and how they get in the way of my relationships.
Fascinating. We'll drop a link. I just Googled Hoffman retreat and we'll drop a link in case people want to check that out. And I know I will. Very interesting. Speaking of kind of inner work, I was reading— by the way, you're barely on the internet. I was Googling around trying to find another podcast you're on or something you wrote.
And no, yeah, this is my first podcast.
Well, I'm honored. That's really cool. But there was one article I found where you were interviewed and in it, you mentioned this idea of learning how to turn off your inner critic and how fundamental that was for you. And I know that's something that, so sometimes this gets talked about in this specific phrase of imposter syndrome, and that was something that never. I never felt like I experienced that. I've never felt like I had this imposter syndrome. I've, for whatever reason, I've walked around with this feeling of confidence of like, ah, I can figure this out. But what I've realized is that by dismissing this idea of imposter syndrome and saying, oh, I don't have an issue with confidence. I don't have an issue with the way I think about myself. I did. I was overlooking some important things about the way that I speak to myself. And the way that I perceive myself. And inner critic, I think, is a much tighter, more accurate way of describing that. So I'd love to hear your journey there.
Yeah, so my inner critic developed, you know, when I was a kid, and it's whatever I made up in response to my environment. And, you know, might have also been what my parents criticize themselves for or me. And that voice is, just creates all kinds of suffering and really prevents me from connecting spiritually. And, and that is like, that's where my overflow beat up. That's like the easy, you know, that's easy fuel. And so the more that I'm in— and Hoffman does a great job of taking people through this journey, but man, if you, you know, the intellect is so incredibly powerful, and it, for me, is like a critic and a judge. And You know, really my intellect is here. The power of it is just to be a really good rudder for me, you know. And, you know, most— we're all plenty smart enough. We don't really need to like have that thing going all the time. And so, you know, for me, I get up and I do just 15 minutes of kind of quiet practice at night. I do a 10-minute gratitude and appreciation. It's what I'm grateful for in my life and 3 things I appreciate about myself. And it's like, oh, okay, you know, it's pretty great.
Yeah.
And I think that we forget to notice what we really like or love about ourselves because we just were just so busy. And when we're so busy, then it's so easy to just be like, not doing that right. But I've, I've changed my day just by anchoring it first thing. I don't pick up my phone first and, and then ending the day not on my phone, but that way. And that goes a long way. And it's a total of 20 minutes a day. I don't have to meditate for 2 hours to get that. The other thing that I am doing to stop it is just to notice I'm breathing. And when I notice I'm breathing, it always stops the inner critic.
Hmm.
Like, I haven't found a way to breathe and be thinking something bad about myself at the same time.
Interesting.
Can you do that? I mean, like, I don't know, like, is it possible to like take a deep breath and think like, yeah, you're a piece of crap?
I'll give it a try.
Yeah, I don't think so. It's pretty hard to do. Yeah, but, but I— it's something that, like, this is my, this is my life's work, is noticing that it's there. I can actually feel where it is. Now. Like, I, I can feel it right here between, like, just above my nose. And so I'm getting actual physical cues when I'm not having good thoughts about myself.
Yeah.
I also have really started noticing when I'm judging someone else, that is a byproduct of me thinking that or being scared of that being me. So I'm, I'm really noticing that, like, look at what they're wearing. It's like, okay, well I must be worried about some, like how I look.
Yeah. And it's so easy to identify that in other people, right? Like I've got some judgmental people in my life and when I see them doing it, I'm like, it's so obvious that you're doing that because you have like an im— you know, a problem with your own self-image. But when it's us, you're like, well, no, that's just, they're just stupid. Like it has nothing to do with me. You know, it's like they're just objectively wrong about this.
My daughter Olive, who's great, she's 26, calls it telling on yourself.
Yeah, it's a great way to say that.
Mm-hmm. So I notice when I'm telling on myself too, in thought.
Mm-hmm. So I wanted to make sure we had time to touch on EOS. You've spent a lot of time in that world as a, as an integrator and many, many property management companies. Run on EOS, either pure EOS or they use a modified version. Some of them have self-implemented, some of them have used an implementer. I was curious. So EOS is getting a little long in the teeth now. It's been around a while. Do you find that it's still relevant in 2025? Is it still, is it something you would recommend or like how, how do you, how do you think about it now that you've been around it quite a while?
Mm-hmm. Yeah. The bones are still really good. It has gaps, but the fundamentals of, you know, having an accountability chart, right? People, right? See, measuring. Yeah. I mean, it's, it's so good and basic, and if you just do that, your train's on the tracks. And so I think there are some things that are timeless and, and so the, the core principles. Are timeless. You know, there are people or there are companies that have spun out of EOS, and you know, when you have something good, you're gonna get competition. So there's a system called Pinnacle. They adapted it in different ways, you know, so it's sort of like WebEx versus Zoom. You get to build a new one and it's all a lot better. And So, so they did that and I find it to be a good system also. And they have, they took some of what they wished were diff— was different and filled in the gaps.
Sure.
A, a lot around scaling and efficiency and financial indicators. So I think that's really good as well. I think My experience is wherever it has fallen short, it presents, you know, either if, if I'm not doing it right, I always check on like, how am I, am I doing this? Am I implementing this piece to its full value? And then I ask myself, well, you know, what's not working? And, you know, go out and fill in a gap. So it's no big deal. I don't think that people have to be rigid about using, you know, people talk about pure, you know, you use your business experience and your network and to fill in the gaps. I do think there are visionary leaders who don't give any system long enough to work. And, you know, it, requires some patience because you're changing the way you do things and there's a lot of discomfort in that for people. And often when you create a lot of accountability, people don't like it and they're scared. So a lot of people bail on it before it can work. And there's some leaders who just want a new flavor, or they go to a retreat or a workshop and learn a new thing. And that's, you know, then company gets whiplash. And then the next thing you try to implement doesn't work because people figure if they just wait long enough, they won't really— it won't work and they won't have to do it. So I think that's, that's something to pay attention to.
Yeah, great insights there. I think the number one question that business owners have once they are on EOS and they're bought into the system is, where can I find my integrator, right? That's what everyone, everyone wants an amazing number two. And you said like, hey, I love being a number two. That's such a rare thing to hear. So for people who are asking that question, like what, what do you, how, how would you respond to that?
There is a really good Harvard Business Review article on The COO role, and I hope you can find it and link to it. If not, I'll send it to you. But it basically says there's no one kind of integrator or COO. It is, it depends on what the CEO needs. And so I happen to be a particular flavor, which is somebody who could really run the company and the CEO could be gone. Like, I, I had a CEO when I was fractional take a sabbatical in New Zealand for a couple of months. So, so I— that's one flavor. And so when I read that article, it's like somebody who's looking for a complementary partner. Yeah, that's the type I am. And Jordan and I worked incredibly well together that way. And there were things that he didn't ever want to do that I wanted to do and was good at. So, so we had a great way of dividing up the work, but we were always on the same page in terms of what we wanted together. So there's a lot of ease in it.
Yeah.
And, you know, a lot of humility. So that, that's a case that works really well. So one flavor is an integrator who can basically run it for you and you go, you know, you're out front or like off or starting your next business. Then there's kind of another flavor I would describe as the kind of project manager integrator. I've seen you do, I've seen visionaries hire that type of person and this person doesn't necessarily lead the leadership team. They just connect all the wire— not just, it's hard work and valuable— connect all the wires, get all this stuff done, run the system, but they are not the person holding the team accountable. I guess that would not be EOS pure, but it happens a lot. And, and it is, it is, it happens. TO visionaries hire that person when they're not ready to let go.
Very common, I think.
And it can work. It, I think my question is, what do you really, like, what's your intent? You know, do you intend to be less involved in every single decision day to day? Do you want to empower your team? If you do, don't do that flavor, the project manager. And then there's this other flavor that I've seen, which is really not probably recommended either, that's more kind of chief of staff, really smart admin type of person. So, you know, and this person's just keeping visionary CEO on track through the leadership team, also without the authority, but more administrative. So those are the 3 flavors. How do I find a good one? If you want somebody who can lead the leadership team, then they need to have had several reps and results. That's it. And the results tell the story. That's it. You know, how did you, what was, how'd you grow revenue and what was EBITDA? Yeah. You know, growth. That's, that's it.
How about these, you know, you previously worked as a fractional COO. Is that something you'd recommend for like a property management business owner with, you know, a business anywhere from $500K to $3 million in revenue? That, is that the right size for that or? Is that a path you, you advise?
I would advise a million plus, otherwise it'll just probably be too heavy on the financials.
Yeah.
So that's one thing that I always, you know, really took a look at is, is their financials before they hired me to see, check to see if it would be a burden. And so they should be having that conversation with anyone they might interview. But yes, I think it can work. I think the challenge with a fractional role is most people, as a leader, you're never going to feel like it's enough because they're not on all the time. And you're trying to afford more skill and experience in your company, you're trying to bring in new experience and have some of the weight taken off of you, but it's not going to be the person who's on call. The fractional person, just by nature of the relationship, can't be the person that's called at 10 at night when something goes wrong. And so I think that Just defining the clear results that are expected, I think, is— and agreeing on that is key. And then defining their role. You're going to do this. I'm going to do that. That's how we operate. If it's going to be 2 days a week spread over these hours in the week, just so Nobody gets disappointed, but when you get a piece of somebody, you really do only get a, a piece of them. And I know that can be very frustrating. Mm-hmm.
Well, that, that's very helpful. And you've been really generous, generous with your time today. Thank you for coming on for your first podcast.
Yeah, thank you. And by the way, I think the number two nature of the, I, I really love just to be behind. The scenes and get the stuff done. So I'm not, yeah, I'm not out promoting myself, but I'm so honored to be with you because you're one of my favorite people.
Oh, thank you so much, Ginni. Well, if folks wanna follow along or stay connected with you, I know you're mostly behind the scenes, like you just said, but should they just connect with you on LinkedIn or?
Please, I would love that.
Great.
Yes, I, whoever's listening, if we're supposed to know each other and, I'd love to know you.
Awesome. Well, thanks so much, Jenny.
Yeah, thank you.
If you like the show and want to get connected to the community, you can follow me on Twitter @PSLohmann and subscribe to my email newsletter on my website, peterlohmann.com. I try to share as much valuable property management content as I can on a regular basis. Thanks again for listening and have a great week.
