Taking Risks and Building Confidence

Tim Ludwig: Heather, thank you for joining me. After hearing some of your story in our previous conversations, I genuinely became an even bigger fan. I was already a huge fan before, and it just increased my esteem for you remarkably. And so now I’m excited to be able to have a chance to share some of those experiences that we’ve talked about with a wider audience here. So, with that, welcome and thanks for joining. 

Heather Endresen: Thank you so much for having me. I always like talking to you and I think this is going to be fun. 

Tim Ludwig: It will be. So, we’re going to go all the way back to the beginning, I mean, not to the moment of your life’s beginning, but back into childhood. And you had some challenges in childhood and had to endure at one point a cross-country move. And so, I thought it’d be helpful to start the conversation by just having you give me a glimpse into what home was like in Virginia and maybe how that changed once you got to Anaheim. 

Heather Endresen: Yeah, so I was born actually in Washington DC. I always think that’s interesting because I don’t have a state I was born in. I was born in Washington DC proper. And I spent my first 11 years there. My parents were really, I don’t think, ever together, so mainly being raised by a single mom and my grandparents basically. So it was like a lot of back and forth, I would say almost 50-50 between where we were living. I went to a lot of different schools. I learned a lot from having to change schools because there’s a skill to that and you learn that very quickly as a child, that you’ve got to find some friends. And there’s a way to do that and a way not to do it. And so you learn the way to do it. And so, a lot of changes, just constant change, I think. And then finally, my mother moved to California without us, actually, for about a year. I have a brother, so without either of us; we were with our grandparents during that time. And then she moved us out. So then, I had one year left, I had sixth grade, I think, left to go there. But we went from having that support system of our grandparents to not, to really being a working mom and just kind of on our own all day into the evening every day. And even before that, we were intermittently latchkey kids, we joke about it now because it is kind of crazy. It’s crazy to think of that. But we were latchkey kids for a while. 

Tim Ludwig: Go back and tell me, you said there’s a right way to make friends when you switch schools and a way that isn’t so right. What were the secrets that you unlocked that made it easier as you got more practice at that? 

Heather Endresen: You needed to kind of show that you were friendly in some ways, just, some smiles and some willingness to participate in whatever conversation or whatever was going on. And then inevitably somebody would befriend you. Somebody would take you under their wing and you needed to be friends with that person or people no matter whether you thought they were really your type or not. Take the friends that are offering friendship to you. And then you figure, after that, you would integrate more and you would eventually find the friends that you clicked with a little bit better. But whoever was willing to befriend you, regardless, those are your new friends. Take them and be thankful that they’re integrating you. 

Tim Ludwig: Have you found that that strategy still works? I can imagine going to a conference or something, maybe it’s the first time there and you don’t know anybody. Do you still take the same approach when you’re in new settings like that and trying to build quick connections with folks? 

Heather Endresen: Absolutely. It is exactly the same thing. And I did something like that in my career where I had spent many years in my earlier career doing SBA real estate loans. A lot of folks in the West do that because it’s easier. The ticket sizes are pretty high. And so, I was very connected to the real estate community, owner occupied real estate. And I switched about 12 years ago to the M&A side, and I started going to conferences where I didn’t know a single person. And I was used to going to conferences where I knew everybody. So it was the exact same thing. I thought, well, this is just like changing schools. I am now in a new school, and I need to make new friends. And of course, as an adult, I think it’s a little bit easier. I think adults are a little quicker to be open and welcoming to new people, but it’s the same skill. 

Tim Ludwig: Yeah. And you mentioned you had a brother. Did he have as much success as you in making new friendships? Was that sort of something that you both shared and learned together, or was his experience different, do you think? 

Heather Endresen: I think he did, too. I think we both- neither one of us didn’t have friends. We always had friends. So, I think he learned the same as I did, like you’re dropped into a new school, it’s time to make friends. But it’s kind of a funny story though, we were only one grade apart and we went to high school, the same high school, and so there was a lot of crossover with friends, but we literally both kind of pretended like we didn’t know each other at school, so people would become shocked that we were brother and sister later on because they knew both of us. I don’t know why we did that, but we did. It was total separation, like I have my friends, you have your friends, oh yeah, there’s a few crossovers, and then they found out and they would be shocked. 

Tim Ludwig: Yeah, it’s interesting. I think a lot of that change can either make you develop those skills and adapt or to sort of turn internally and figure out a lot of ways to be really self-sufficient, and maybe that’s books or video games or other hobbies or just being alone or outside or whatever. So, it’s just interesting to note that you chose the more extroverted path, I think, in seeking that connection. And it sounds like once you got to California, there was a lot of independence. You said your mom was busy and working and this latchkey syndrome. And so, my childhood was similar when I got older. And throughout all that, I think you described to me your personality then was still friendly, fun, but maybe a little bit shy in some ways and certainly not much of a leader, that you tended to be a little bit more of a follower, just go with the flow kind of a person in a lot of situations socially. But at one point, you got up the courage to break out of that and do something that was a little bit braver and try out for the cheerleading squad. And I’d love to hear more about that. 

Heather Endresen: Yes, I think it’s funny that I chose that as one of my moments that was pivotal for me but because I’m not really that kind of person that I think of as being really into that social network. But I was more of a follower, and one day, I was walking along to school with my friend and saw the poster for the tryouts, and I just decided right there, I’m going to try out. And I told her that, and she said, well, I’m going to try out too then. And we did, and it was kind of a social risk because if you did something like that and you didn’t make it, there was definitely some social risk involved. And I think I was just at a point where I had that confidence, that it was going to be fine, regardless. And I wanted to do it. And so, what am I waiting for? There’s only four years of high school, go ahead and try out. So, I did, and I made it. And it was not- like you asked me, was it all you thought it would be? No, I guess it wasn’t. It did raise my social standing a bit. I guess I got to see that it wasn’t the end all be all, but it was important, I think, for me to take that risk of doing something like that. And thankfully it was successful, and I gained a lot of confidence from that. I applied it in other aspects of my life, that it was okay to take those risks and go for the things that you want to do, rather than listen to that voice in your head that’s telling you you can’t or you shouldn’t. 

Tim Ludwig: Even in high school, did it spur you on to take more risks like that, or was that sort of like the one big-? Because you singled it out as the one sort of pivotal moment, and I’m wondering if that was just because it was the first time or it was the biggest time or if there was a pattern that came after that? 

Heather Endresen: Not really in high school. That was it. That was my one big thing there. And really, it applied kind of after high school when I started working and I started realizing that I could ask for a raise or I could ask for the next promotion. And that was just a few years later because I started working right out of high school. 

Tim Ludwig: And that’s almost more, I mean, it’s definitely risk taking, but more self advocacy, too, which I think speaks to that inner sense of confidence that you got to be able to take that first risk to even try out. The other part of that story- 

Heather Endresen: And the independence. Oh, sorry. 

Tim Ludwig: No, no, go ahead. 

Heather Endresen: Yeah, the independence, I think, of having always been so independent, I tell myself you can do it. I don’t wait for my- I didn’t wait for my friends or look for other people to tell me I could or couldn’t do it. In fact, I rarely listened to other people. Maybe that’s not a good thing. But I really listen more to what is going on inside of my head and thinking that I could do it. And so, I think that’s the independence that all that latchkey kid lifestyle got me. 

Tim Ludwig: When you’re talking yourself up like that, is that like a deliberate inner monologue where you’re sort of psyching yourself up or it’s just now it’s so second nature that there’s the confidence there and it’s not like, okay, let’s get ready, let’s go, we can do this or I can do this, it’s just like you just know at this point and you just take action, I think, even before maybe a conscious thought? 

Heather Endresen: Well, it’s a little different for me. For me, it is kind of blocking out the naysayers or the negative voices that might be around you. As a woman, and I think this happens to everybody, but as a woman, you might be surrounded by women in your family, your friends, who aren’t going to choose the same path that you are. And they will tell you, you shouldn’t do this, or you shouldn’t do that, you can’t, you shouldn’t, et cetera, et cetera. So for me, it was more about not believing that, not believing those outside voices that are saying, no, you can’t and really just listening to the one inside that says, I really think I can and believing that one instead of believing the people that are telling you maybe you shouldn’t. 

Tim Ludwig: Yeah. The last part about the cheerleading story that I found really interesting was that it was clearly aspirational, want to be a part of the inner social circle at the high school, sort of elevate your status, which I think for a lot of people, if they achieved it, would then make them want to really like fully engage with that and be as much a part of that community as possible. But you told me that you actually weren’t all that taken in by it once you got there. You sort of grabbed the brass ring and then said, hm, this isn’t all it was cracked up to be. 

Heather Endresen: Yeah, it was too much drama and nonsense, a lot of that, and craziness. I grew up, I graduated in 1986. It was quite a crazy time. And that wasn’t me. I didn’t really want to be fully engaged in that lifestyle. I was proud of myself that I did what I wanted, but I also could kind of not take the part of it that wasn’t a fit for my personality. 

Tim Ludwig: Yeah, and sort of continuing on this theme of independence and being more of a self-starter, after high school, you went right into the work world. You were taking some classes at the local community college, but it was largely a story of work and self-sufficiency, right? 

Heather Endresen: Absolutely. I was on my own from the age of 19 and absolutely on my own with no additional support. And so I was always working. I ended up getting a job in a bank from a friend. The first one was counting cash in a vault at Bank of America. It was horrible. I had no idea how awful it was going to be until I was there. It was like a factory. And so, I was always working and just figuring going to school at night, maybe I’d try to get a degree that way. But it was a struggle, definitely. 

Tim Ludwig: And were you living alone or did you have roommates? 

Heather Endresen: I had a roommate; that was really the only way to do it. I mean, I think it’s even harder for young people now, but at least then with a roommate, you could financially make that work. So that’s how I did it. And I had a little budget and I saved my pennies and I watched every penny that I spent. 

Tim Ludwig: And you really liked working much more than the school part too, right? I mean, you found like, okay, this is something where, maybe not the cash counting part, but as you got to like maybe to the next role… 

Heather Endresen: Yeah, I did. I got so many positives out of my work life. I learned a lot, and I’m someone that just likes to learn by doing. I think school is hard for me in that it’s just so esoteric sometimes. It’s very difficult to- you don’t feel like you’re learning as much. And when I was at work, I felt like I was learning all the time. And I was also getting a lot of really positive feedback from the adults, the older adults around me that felt really good. So, I felt like it was an area where I could excel and feel really good about myself and also take care of myself, put a roof over my head. It was really positive for me. 

Tim Ludwig: Yeah, I think the feeling of earning your own money that came from your own sweat and labor is for a lot of people a real milestone moment where they go, okay, like I get this now, all these things, like this feels really good. It’s empowering. 

Heather Endresen: Yeah, absolutely. So, my friends were still at an age that they were partying and going to different colleges, and I just thought, I’m done with that. I don’t need to party. I don’t need to do any of that. I worked and I liked it and I would sometimes, this is kind of funny, I would sometimes be a little bummed out when Friday arrived because we weren’t going to have work on the weekend, as crazy as it sounds. And I was in my 20s, that’s how I felt. 

Tim Ludwig: How long did you keep up with the school before saying, you know what, this isn’t the best use of my time and it’s not as interesting or as rewarding as just doing the work stuff? 

Heather Endresen: Yeah, I think it was at least a good four years of kind of grinding away at night school. And what was happening is I was getting promoted and I was getting jobs in this little bank that I worked for that you were supposed to have a college degree for, and I was getting the pay of someone who would have, so I was getting to the point where this is, I don’t know what having the piece of paper is going to do at this point, and I’m tired. It’s hard to work all day and go to school until 10 o’clock at night. And so I finally just decided it was okay to stop and I did. But I didn’t like to advertise it because it was something that for my age group was considered like a really bad decision, that you were going to end up, I told you this, we were told as kids, if you don’t go to college, you don’t get your degree, you’re going to end up in a factory. And like the idea of a factory, which is not a terrible thing necessarily, but to us, it was portrayed as like the worst life you could imagine that you’re going to be headed for if you did that. So I never told too many people that I didn’t finish. 

Tim Ludwig: Yeah, they could have said you’ll be stuck counting cash for the rest of your career. 

Heather Endresen: That was my factory experience, and it was not fun. 

Tim Ludwig: And once the banking thing, and I think you got out of the cash room, things really started to click and you had a really quick rise in the ranks there. And so, by age 23, you were a department manager, which is very young. And I imagine, tell me if I’m wrong, but I imagine in the banking world, there’s a lot of stability in a lot of those jobs. And so, you were probably surrounded by and in charge of a lot of people who had a lot of tenure and certainly older than you and had been around the block a number of times. And that must have been challenging. 

Heather Endresen: It was. It was. I mean, I was thrilled to have these opportunities given to me, and I took them very seriously. But at the beginning, I was almost embarrassed to ask my staff to do things for me because they were 10 years older than me. And so I did a lot of please and thank you. I just didn’t feel comfortable at first with how to talk to them about doing things. But I got there. And I think fortunately for me, they were great. The people that I worked with never gave me a hard time and called me kid or whatever they could have done to be offended by my age at that point. So it was a nice group. It was a good way to learn at that age. 

Tim Ludwig: What were the circumstances for that first promotion to the department manager that allowed you to jump the line so to speak? 

Heather Endresen: Yeah, it was crazy. I was in a small bank, the early 90s were- there was a commercial real estate crisis, especially with small banks in California. And they were under a cease and desist. The bank ultimately made it, but they had to cut costs. So, one day they had a layoff, and they kept calling people upstairs, and I figured I was going to get the call because so many people were getting the call. At one point, my boss was called up and he came back down to pack his things. So I figured I’m next. They finally called me at the end of the day and said, oh no, we’re not laying you off. You’re going to be the department manager. And I said, I don’t think I can do that yet. I don’t think this is a good idea. And they said, it’s fine, you’ll be fine. And so, I realized they were choosing the low cost salary there. And the bank was not in good shape, so they kind of didn’t have maybe too many great choices. So, I went home that night and thought, well, what if I fail? That’s not going to look good. But then I thought, at this age, I could bounce back if I failed. I should just go for it and do the best I can. And ultimately, I was successful taking over the department. But it was a little scary for a 23 year old. 

Tim Ludwig: Oh, for sure. At 23 years old, if somebody would have done that to me, I probably would have been excited, but I think that would have been eclipsed by the terror that I felt. 

Heather Endresen: Yeah, I worked, that’s when I really started working longer hours because I would review every file. I wanted to make sure I knew everything that was going on because I was nervous about what I didn’t know. 

Tim Ludwig: And then you got another big promotion at 27, and by 30, you were a senior vice president. So again, like I said, just a meteoric rise in a very short period of time. And something that I’m guessing also was a very male dominated industry, maybe still is, but certainly then I would guess it was. And so just to give me a little bit more perspective, what was banking like as a woman in those years? 

Heather Endresen: For the most part, I think I was treated very fairly. I was expecting or you read stories and I was thinking maybe there would be some forms of discrimination more than there were. There were really very few. There was one where a boss decided to have the team meetings or the team offsite, annual offsite, I guess call it a team building event, it happened to be a charity event that didn’t allow women. It actually specifically said that on the invitation. And that was pretty tough for me. I was the only woman on the team and I found out only in the second year that they were all doing this every year and that I couldn’t attend. So I thought that was probably the most blatant like, wow, that doesn’t seem right. I know that charity does not do that anymore, but they did. So that was probably the worst. I think for the most part, people treated me really well. And what I found, what I learned was the people that are kind of feeling stuck at a lower level and especially in banking, that was mostly women, they were in operations and they felt stuck there for a lot of reasons, they were the ones that would tell me you can’t, you shouldn’t, you won’t make it, all the kind of negative words. The people, whether they’re men or women, at the next levels up that didn’t feel stuck were very supportive and said the exact opposite and said, let me help you, I’ll be happy to teach you. Excel wasn’t even a thing. There was a program called Quatro, and somebody, a man in the bank showed me exactly how to use it, and I created a spreadsheet for one of the construction lenders and he was just floored, it was like magic to him. It’s so funny to think about that now. But a lot of people at that level, men and women, helped me. So I didn’t feel like I was being discriminated against. But if you stayed at the lower levels, it was psychologically hard because they felt stuck so they kind of wanted you to feel stuck too. And I don’t think consciously, but sort of unconsciously, that’s what happened. 

Tim Ludwig: Yeah. I want to ask about what you think were your attributes that allowed you to be so successful through that chapter of your career. And as a part of that, I’m also wondering if you had mentors along the way and if those were people that you cultivated or they just sort of showed up and took you under their wing, or what was it that allowed you to get all the way up to that level by the time you were 30? 

Heather Endresen: Yeah, I mean, the first one was what we talked about already. I just wouldn’t listen to the people who said you can’t. I would just try. Like I’d try out for cheerleading, I would try out for the next job, even if I didn’t have the degree or somebody else said I shouldn’t try, I would just go ask for it. So that was part of it. And then yes, I absolutely had mentors who would sort of take me under their wing. They would say, you’re really smart and you work hard and let me take you out to lunch and talk to you about what you can do next. So I definitely had really great people along the way that just wanted to help me and offered to help me, which I can never thank them enough. So I think you can never do something, no matter whether it’s owning a business and running a business or having a career in banking, you need other people, absolutely. 

Tim Ludwig: I imagine part of it, it sounds like you’re also an extremely hard worker. 

Heather Endresen: I like to work hard. I enjoy it. I think it’s sometimes to my detriment because in banking, everybody’s not that way. That may be a surprise. And it would frustrate me. To be around co-workers that are not hardworking was really something I disliked a lot and it showed, so that was probably, that’s to my detriment. I couldn’t- I was not very accommodating of people who I felt were kind of lazy and not hardworking. And unfortunately banking, it’s a type of career that sort of attracts some people like that. 

Tim Ludwig: Yeah, which is not, again, a bad thing in itself. I think for the right circumstances with the right people, that’s actually a great lifestyle. They can punch in, they can do their job, and then they can clock out at the end of day and enjoy the rest of the things that they’re interested in and be there for their family. And so, I mean, industries need a lot of those people as well. 

Heather Endresen: That’s true. Exactly. It was just very different for me as an individual. 

Tim Ludwig: Was that around the time, I don’t know when you started having children, was it around then or just a little bit later? 

Heather Endresen: Yeah, so at 30, I made my goal of getting to a senior vice president. I successfully started another SBA department for a bank. So, that’s when I had my first child, my daughter, Rachel, who actually works with me now at Viso. So, a lot of people know her now as well, but that was at 30 I had my first child. 

Tim Ludwig: Okay. And did that make you think that you wanted to stay in the work world like that, or did you consider leaving and becoming more of a stay at home mom? I ask because I was talking to a woman just a couple of days ago who was, and I’ve heard it from a lot of women over the years, including my wife, about just the dilemma that that creates for so many women, at least in our culture, about do I want to stay home, do I want to work, do I want to, can I do both effectively? And it just surfaces a lot of emotions. And so, it’s just, for me right now, sort of top of mind since I just had a similar conversation. 

Heather Endresen: It totally- yes, absolutely. I don’t see how it couldn’t happen. When you become a mom, it changes everything. And here I’ve been so focused on work and I was really torn. I didn’t like going to the office. Fortunately, right at that time, it was kind of the beginning of even being able to work remotely from home. There was VPN and you could log in. I was actually logging in just at the end of my pregnancy while I couldn’t go back, go into the office, so I already had that set up. So what I started doing, I had a person coming in every day to take care of the baby while I worked for a few hours. And so, I just didn’t go to the office as much. And I kind of kept it that way. If I did go to the office, it was for shorter periods, and I’d come back and work on my computer at home. So fortunately, that was just becoming available. I mean, if that wasn’t available, I think I would have had a really tough time. And yeah, it does, it surfaces a lot of emotions. You don’t know- for a while there, you feel very ineffective at both. You’re not being a good enough mom, you’re not being good enough at your job. And for a little while I did actually, I took one year and tried to be a stay-at-home mom. I say try because that was a little too much. That was too extreme for me to go from what I had been doing. So I eventually learned that it would actually be better to do what I had been doing, which is take advantage of the ability to work remotely some of the time, have someone in the house to take care of the baby and still have my job. So eventually, I came to that as a good happy medium. 

Tim Ludwig: Yeah, I think everybody has to find their own right fit. I hear more dads also talking about some of these things now, which I think is a good sign. And I know for me, when I had our first child, it was after about six months, I was going into the office every day still, and infants sleep a lot. And so, I would leave in the morning and my daughter would be asleep. And if I came home at a reasonable hour, I might get a half an hour with her while she was awake and then she’d be asleep again. And I thought, man, if this is what parenthood is like as a dad, this is not so great. Like my kid is just asleep all the time. I don’t get to experience all these other things. And it was one of a number of ingredients for me at the time that created a huge shift in how I organized and prioritized my life. And it was a period of a lot of introspection to sort of figure that out, it sounds like in a similar way that you did. I tried different things until I found what was the right balance for me. 

Heather Endresen: Right. And you want to be there, you’re right. Like if you’re leaving and all the time you have with your young child they’re sleeping, that’s a horrible feeling, yeah. So, it’s definitely a challenge, and I’m glad that we have so much more remote work now because I just think that opens the door for moms and dads to do things that make sense for their family. 

Tim Ludwig: So, life was smooth, chugging along, going really well, and then a few years later, it’s sort of this cavalcade of adversity, I think, crept into your life or maybe exploded into your life is a better way of describing it. To me, this is probably the sort of crux in the whole story is this little episode here of things that were going on both personally and professionally. And I’d love to just have you unpack that a little bit. 

Heather Endresen: Yeah. So, my son- so I had my daughter first and my son four years later. And when my son was five years old, he was diagnosed with lymphoma. So, we had to get him in for chemo, the whole works. It was just, it’s a blur to me, as I told you now. Like when I think back, it just was such an incredible event and so scary. But he survived. And I have to add, the year was 2008. And I’m divorced from his dad now, but we were married at the time, and his dad and I both worked in banks and finance. 2008 was the absolute worst time ever to be working for banks. And his dad, my ex-husband, had already been laid off before the lymphoma diagnosis came in. So, I was the only one working, I had the health insurance, and this happened. And so fortunately, the only way I kept health insurance was through my co-workers who literally did the work for me. It was kind of two things happening at once, but in reality, I experienced it only as one thing. I didn’t really realize how bad the financial crisis was becoming, to be honest, until after my son’s treatment, we were out of the hospital, and I went, whoa, this is really bad, I didn’t really realize. Anyway, I had these great co-workers who realized the situation and did my job for me basically so that I could basically stay on payroll, stay on insurance, and not be working and be at the hospital. So we went through this difficult situation. Our son got through the chemo. He was cancer-free and has remained that way since then. He’s now a healthy 21-year-old. But within a few months of ending chemo, there were some other symptoms happening. And ultimately, he was diagnosed with type 1 diabetes. And so that frankly was happening at the same time. They just didn’t realize it until after we got through all the treatment that that’s what it was. So, it was just this incredible like, oh my gosh, now what? And this is permanent, this is not get through the treatment and get to the other side. This is a complete change in really everything. Anybody that’s got a family member with type 1 diabetes, you realize it’s eating, it’s exercising, it’s everything you do, and you have a lot to learn. And so that came immediately on the heels of cancer treatment. So, it was just an incredible shift in my life and our whole family. 

Tim Ludwig: Dealing with that level of stress, how did you manage that? I mean, you said that just life was sort of a blur, but do you remember how, just even day to day, like how do you get through something like that? 

Heather Endresen: I don’t know how I really managed it. I feel like I just survived it. I had real difficulty sleeping. I had a doctor- that’s when I learned about Ambien, unfortunately. That was the only way I could sleep for a while, and I also learned that you really can’t take Ambien as long as I was taking it. So eventually, I had to like find a way to get off Ambien and sleep without it. But things like that, like I just needed support and help however I could get it because it was just so stressful. And I think everybody deals with that kind of stress differently. I unfortunately want to read everything there is to know. So, I would kind of dive into the to the details and maybe too much, maybe like if I were to do it over, I don’t know how I could stop myself from really doing that. But I saw other people getting through their kids’ situation a little more serenely than I did, and maybe that was part of how they did it. But I don’t know. I feel like I just survived. I didn’t really have a good way of managing it. It was very difficult. 

Tim Ludwig: And then with the type 1 diabetes diagnosis, how did you learn and educate yourself and educate your son about that? Was there a community that you plugged into or was it you just sort of going down the rabbit hole again and reading and learning and talking to like professionals?

Heather Endresen: Yeah. So, the hospital itself gives you a lot of training and they have classes, but I actually learned the most from an online community, actually, of parents, kind of a message board and going on there. And there’s just a lot I read and interacted with those other parents. And now they’ve even got Facebook. I’ve got a Facebook group that I still belong to that is like that. And so, it’s a good way to problem solve and realize that everybody’s got the same kind of issues that you do, or if you have a weird one, that there’s going to be somebody else out there that does as well. But it’s kind of all, it’s a huge learning curve. And it’s a lot of- it’s kind of nerve wracking in the beginning, especially with a young child, and they’re growing, and it’s always changing. And I know that it makes you feel a little less connected to your friends and family that don’t have that. Because when you try to relate some of the frustrations or some of the challenges that you’re dealing with, they just don’t understand. How could they? They can’t understand. So they might say, well, doesn’t he just take insulin? Like, yes, it’s not that easy. So it was a little isolating. And yeah, you did sort of have to connect to people, to other parents and kids. And fortunately for my son, he was in first grade, and one of the kids that is still one of his best friends also had type 1 diabetes. So, they had each other all through school, which I think was really, really helpful for him. 

Tim Ludwig: What were some of the ways during that chapter and getting through the cancer treatment process that people provided support that felt meaningful? Because I think it’s something that a lot of people struggle with. I know when I have a friend or loved one that’s going through something tough, to your point, you can’t understand if you’re not really in the circumstance. And different forms of support, I think, feel more or less helpful if you’re the person on the receiving end of that. And you know people are well-intentioned. But what are some things that stuck out to you that people did that really felt like they had the impact that was intended? 

Heather Endresen: Yeah, number one at work, the work network was just fantastic. And they just made it so that I didn’t even need to think about it. So it was great. The neighborhood was fantastic too. They put together like a website, I forget the name of it now, where they not only brought us meals, but they took care of our horses. We had horses in the backyard. So that was another challenge. Like, someone’s got to feed these horses when we’re in and out and not home. So, people I didn’t even know were coming in the backyard and taking care of the horses, dropping off food. It was really great. And some people came and visited at the hospital, which was really nice. So, I don’t think you can go wrong showing your support. I don’t think you can do the wrong thing. The only time I think I ever felt like anybody maybe did the wrong thing was if they took something that wasn’t exactly this experience and said, I understand how you feel. And then you think, no, your daughter’s knee surgery I don’t think is the same thing. That’s about it. But everything else that people did I think was just fantastic. It was very wonderful to have that support. 

Tim Ludwig: But yeah, you don’t want them to turn around and make it about themselves and what they overcame. 

Heather Endresen: Yes, exactly. Yeah, just try to avoid that.

Tim Ludwig: And then I think when you go through great challenges like this, it’s an opportunity for growth. And I think even despite best efforts, it’s impossible not to grow. It’s painful. We don’t like to grow this way a lot of times. We’d rather save ourselves the experience. But what did you learn about yourself getting through that period? 

Heather Endresen: So, I learned that life is going to throw good things at you. It had been throwing a lot of good things at me. And it’s going to throw bad things at you. That’s just life. And that you can get through it. You will get to the other side, no matter how bad it is, you will get through it. If you’re still breathing, you’re getting through it somehow. So, I learned that, I think I told you, I sort of relate it in my head, like playing at the beach. Like as a kid, running out there in the waves and staying out there all day. And once in a while, a big wave would come and toss you and roll you under the water and you don’t even know which way is up, and then all of a sudden, you find yourself at the beach or on the sand again. And so I kind of felt like it was like that. It was like, you know what, the wave did hit, it was terrible, but I’m at the beach again. I’m on the sand and everything’s different, but everything’s okay. So, I just learned you can get through just about anything. 

Tim Ludwig: But there’s a resilience there that you can tap into if you have to. 

Heather Endresen: Yeah, absolutely. 

Tim Ludwig: Going back to the professional realm for a minute here, you had talked in one of our earlier conversations about a lot of banking being commoditized. And one of the things that you gravitated towards was opportunities where you could break that box and find something that was more differentiated. And I think you’ve done it at least a few times. And how did that help to shape and inform your career and your experiences as a professional in the industry? And how did you figure out how to do that? Or did you just sort of stumble into it or were attracted to bright, shiny objects that were new? Or was there method to the madness? 

Heather Endresen: Yeah, so I was able, because I didn’t finish college, one of my banks allowed me to go to banking school. In banking school, there was this really great professor that hammered that point home that banking is increasingly commoditized and you better find a way, if you’re going to be a leader in this industry, you better find a way to differentiate or you’re nothing. You’re a race to the bottom. In my work life, nobody was really saying that inside the bank. But I had that voice in my head from the school going, yeah, I see it everywhere, I see what he’s saying. And I felt kind of handcuffed in the SBA program. I was always an SBA department manager for all those years. And I thought, well, how can I differentiate? I am stuck with a government program that is totally rigid. And it’s the same thing for every bank. We’re all following this rule book. But I kept thinking and thinking and thinking. And so eventually I did see the opportunity to differentiate within that, and that was within acquisition, M&A. I realized that all of our competitors were doing what was easiest, which is working capital or business real estate acquisition, commercial or owner-occupied real estate acquisition. Those are kind of cookie cutter easy, and that’s what I was doing too. And when I started doing a few business acquisition loans, I went, well, these are really actually a lot harder. These are very different. The whole language is different. The type of clients are different. This is going to be a change of ownership. It’s not the entrepreneur anymore. It’s somebody buying the business. And so I realized there was a chance to differentiate by just being good at that. None of us were good at it. I always say, including me, we were not good at it. And I noticed that as well and thought, well, what we need to do is get really good at this by focusing on it. And that’s how we can differentiate. And that’s how I can finally fulfill that mission that that professor gave us all those years ago to be different and not be a commodity.

Tim Ludwig: That seems to be a common thread of success at an organizational level for a lot of companies, but also at the individual level where people specialize and focus and then have an opportunity to become really, really great at a small thing. And if the market is big enough, then that allows you to have a success of some level of magnitude. 

Heather Endresen: Exactly, exactly. But in banks, it was very difficult to be an SBA department serving the retail side of the bank, all the people in the bank and your salespeople and say you know what, I don’t want to do all that other stuff, by the way, the other stuff that’s easy and the other stuff that’s safer because it’s got real estate collateral, I want to do this really hard thing over here and only do that. So, we had to- it was a journey to get to the right bank that would allow us to do that and to find a team that would come with me and do that. So ultimately, the bank was Live Oak, and the team was Lisa Forrest. I tried to get other team members, but it was very hard to get people to switch away from what was easy to focus on this little narrow thing that was hard. But I believed in it, and I knew that it was the one way to differentiate. 

Tim Ludwig: You’ve taken that and now gone out again, another big transition in your life, a year ago plus, you left Live Oak and started Viso. Congratulations, by the way. I think that’s really exciting. And operating inside a mature industry that’s known for being stable and risk-averse, you’re doing these things within the realm of that that were maybe a little bit more avant-garde and risk-seeking. But this was a big jump. How did you reach the conclusion in your own mind that you had enough conviction in the idea and in yourself and it was the right time – I think timing is crucial in these things – for you to branch out and try this on your own? 

Heather Endresen: Yeah, I probably could have done it sooner, but like you said, I’ve been a banker, I’ve been in that safe cocoon sort of, at least mentally, it felt like a cocoon, in these big banks that you’ve got a W-2, you’ve got insurance, all those good things. So I think I was unfortunately falling victim to the thing I was always proud of not doing, which is listening to the negative, you can’t, you shouldn’t, don’t do it. And finally, I saw that the market had grown and matured a little bit. There were a lot more banks than just Live Oak. When I went to Live Oak, I think we were sort of the leader of doing SBA loans for acquisitions that didn’t have real estate collateral and with cash flow lending, and so we kind of pioneered something. But the other banks were getting there pretty well, and there was this kind of broader market now. The market was shifting. So that was one, I saw the opportunity in the market. And two, just in myself, I’m older now and my kids, my youngest is one year away from graduating college. And it was also kind of like, if I don’t do it now, when am I going to do it? I can’t wait any longer. And of course, it’s the easier time in my life to do it because I’m more financially stable. So it also felt like less of a risk for someone like me to go ahead and take. So still at the same time, it still felt very daunting to just go ahead and rip the band-aid off and say, okay, I’m quitting, I’m leaving, and I’m doing this. I will tell you, I was inspired by people on Twitter or X or whatever we’re calling it now, who are entrepreneurs and who really talk a lot about bias towards action. Just do it, quit overthinking, quit building the website too much. And I finally internalized that and said, that’s correct. And I had this longer term plan, I was going to do it a little bit later, and I thought, no, Heather, you’re going to do it now. That’s what you need to do, just start doing it. And so that was how I finally made the decision. 

Tim Ludwig: How did it come to be that your daughter ended up working with you? Is this something she was interested in before? Did you have to twist her arm? How did it end up that you two are working together? 

Heather Endresen: Well, first of all, it’s like a dream come true to be working side by side with my daughter. So that is amazing. But she was just in a job that she wasn’t thrilled with. And she was complaining. I honestly didn’t know if I’d have enough work for her when I started. But I quickly found out that I would or I did. And so, I just started talking to her saying, do you want to just come over and work this time and that time? When are you working? So at first, she just did a little bit for me part-time, and then we just decided, okay, there’s enough here where I can pay you, you can come work full-time. And so that was pretty quickly. I think that was within the first three months, and she loves it. So that was the other thing; she kind of needed to dip her toe in and make sure she liked it and that the family dynamic was working okay as co-workers. But it has worked really, really well. She loves it, and I’m thrilled that that’s a benefit of being an entrepreneur that I never really even thought about until it started happening. So, I’m super thrilled. 

Tim Ludwig: Did you have that in mind that she might be a good fit and that there’s maybe mutual interest even before you launched, or like after you launched, like, gosh, I’m going to need some help and I know she’s not happy and I could see her fitting in here?

Heather Endresen: Yeah, I thought there might be a chance in the beginning. So, I mean, I told her before I made the decision, hey, this is what I’m going to be doing with that in mind. So, just to kind of whet her appetite and she actually did set up our first CRM. Before I even started, I needed something. And so she got in there and she set it up. So she was already doing a little bit of work even at the very beginning, but I didn’t know how it was all going to come together, but happy that it did. 

Tim Ludwig: Oh, that’s really cool. It must be so fulfilling. What about the experience so far have you found most surprising or enjoyable? 

Heather Endresen: It’s enjoyable to me as an independent person just feeling like this is all me. There’s no question, when you’re in a bank, is it them, is it the brand that they have, or their systems, or their support? This feels good because I know there’s nothing else but me. It’s me waking up and making my own decisions, and that feels really, really good. I think it’s challenging to grow. I certainly feel that. When we’re successful and more and more people are coming our way, we’ve got to find a way to serve everybody, and that’s not easy. Growing as a really small company is challenging. So when I talk to people who want to buy a really small company, I can have that conversation with them that there is sort of a benefit to buying something a little bit bigger that someone’s already taken it through that first growth curve. So, I think that’s probably some of the challenges, just learning how to manage growth and do it efficiently, not spend too much to support the growth that you’re seeing. 

Tim Ludwig: I will say as somebody that’s been around a lot of small businesses for a fairly long time, that’s a first class problem. It is a problem, but when you’re talking about growth and how to manage that, you’re in a good place. 

Heather Endresen: Yeah, absolutely. That’s how I felt too. Like this is just so great that the business got traction and people like the service. And so, yeah, I’m in a great position to have those kinds of problems rather than cashflow problems or something else. 

Tim Ludwig: Exactly, exactly. So final question, given everything about your life’s journey so far, what aspect of it has been most surprising to you? Like, if you could rewind as a little girl and then sort of have a glimpse of where you are now, what would be most surprising? 

Heather Endresen: Yeah, I don’t think I would have ever thought I would be in banking with spreadsheets and numbers and that that would have been the thing. I think I would have thought of as a child of something more colorful like a jockey or something. I was into horses. And something more romantic than a banker with spreadsheets and that I would actually love it as much as I ended up loving it. So, I think that’s probably the surprising part.

Tim Ludwig: I love it. Well, and your love for it has always shown through to me. I think that’s part of what makes you really successful at what you do and such a special part of the community that we’re both a member of. So, we’ll wrap it up there. But Heather, thank you again. I really, really appreciate you joining and loved the conversation. 

Heather Endresen: Thank you, Tim.