The Accidental Entrepreneurs

Ep 20: What was the leadership style like at your company?

Ira Gordon & Stacee Santi

Ever thought about how leaders adapt as their startups morph into the real business world? Stacee and Ira pull back the curtain on their evolution from the early days of winging it with their teams, to mastering the art of delegation and trust in a growing company. We get real about the gnarly bits of meshing with larger corporate beasts post-acquisition and why having your ducks in a row with processes can save you from a world of hurt down the line.

Special shout outs:
Mike Fisher
Fish Food for Thought newsletter
Dani McVety

Tips of the week:


Stacee:

Well, Ira, here we are at another episode.

Ira:

Again at last.

Stacee:

Again. Okay, so I wanted to tell you about an email that came into my inbox just this morning. I follow this guy. His name is Mike Fisher and he has a newsletter called Fish Food for Thought, which is so brilliant. Just there. I was so jealous because I, like I, wish I had a cool last name I could do something with. But in his newsletter today he referenced a study that was done by a professor, a photography professor at the University of Florida, and for his class for this semester, half of his students were told that their grade would be based on sheer volume of pictures submitted. So if you put, if you submitted like a hundred pictures, you got an A 80 to 90, you know, you got the next level down and so forth. And the other half of the class was graded on one picture. They only had to send in one picture for the whole year and it was to be their best picture and that would be their grade.

Ira:

Would much rather be in group one.

Stacee:

Yeah yeah, much rather be in group one, yeah yeah. So fast forward and what ended up happening is the best pictures of the whole class were from the people that were taking hundreds of pictures. They dominated in producing the highest quality. So isn't that interesting when you think about iterations and mistakes and failures and trying, trying, trying that you're really getting better.

Ira:

A lot of swings to hit a home run.

Stacee:

Yeah, yeah.

Ira:

All right. Well, what is our topic for today?

Stacee:

All right. The question of the day is what was the leadership style like at your company?

Ira:

So this evolved substantially along the way for us, because we truly started our business as a bunch of idiot students that wanted to play around and build something cool, and so we had almost no real leadership style at the beginning, aside from just a very collaborative and wanting to build something that worked and worked well sort of attitude.

Ira:

I think really a collaborative leadership style would have been where we started and then, as we grew and expanded into having a bigger team, I think that became a sort of very trusting leadership style, in part because of necessity it was kind of our additional side hustle, if you will although I don't know if that was a term back then and so we brought on people that we just felt really sort of got us and got our style and would fit well and could operate pretty independently and would come to us for guidance and we certainly were always happy to get our hands dirty and kind of dive into whatever needed to get worked on or fixed, and so maybe to some extent kind of that willingness to feel like no job is not mine or beneath me in some way, and I think that that was certainly an attitude that would never have flown at at our business Cause when you have a small team, you know any problem we don't have, like a person whose job title is solely dedicated to addressing that problem, like everybody has to take on the ownership of, um, you know, trying to both prevent and fix problems.

Ira:

So that's, that was sort of our approach. I think it does get really hard to maintain that style of leadership at some size of company. I don't know what the magic number is, but I've kind of felt like somewhere between like 20 and 40 people at the businesses when, like, it just gets really hard to have that type of connection and relationship with all of the people that can facilitate that sort of you know. Just, you know deeply trusting and know that you know somebody's going to come find me if they need me and I trust them to do a great job in the meantime and we'll connect, you know, on whatever cadence to just sync up and make sure that we're on the same page. But I think that does get hard once you go from being small to, I guess, what most people would think of as a sort of more medium sized.

Stacee:

You know you're so right, because one thing I struggled with a lot when we got acquired was taking my small 30 person company and putting it into a 300 person company, and I was so unprepared for this I hadn't even thought about what that would feel like and it turned out to be a big problem for me because, um, you know, when you're used to cross-functioning and you just do whatever the people on my team were so multi-skilled across the different sales force, or zoom, set up a marketing set, set up a webinar book, a hotel, we could all do all these things and then when we try to go into this big company and we perceive it as being super slow, it is like trying to turn a cruise ship around versus a little speedboat and you have to go through all these channels to do this what seems to be the simplest of things and, uh, it became so frustrating for me and I ultimately I couldn't hang in that company because I couldn't stand it, and of course it has to be that way.

Stacee:

I realized at first I was like you guys are like what I don't.

Ira:

what are you doing here? Yeah, you don't know what you're doing this is going to take.

Stacee:

any of us over here could do this in like 15 minutes and you're telling me it's going to take four weeks, you know. But what I realized is you start, when you start just randomly doing things that just because you can you do know how to do them, is you start throwing all these wrenches into the equation that trickle down way far in the future to more problems, and so it is necessary to have these processes in place and these oftentimes silos where work is getting done, and I mean it was so hard for me I couldn't actually do it.

Ira:

Yeah, I mean, you said the P word and I have found myself at times just being like like the enemy, of wanting to focus on process, because in the early stages it's so inefficient to build processes, because those processes change all the time and so the amount of time you spend building them feels really wasted. But I think similarly at some size of team, ultimately for people to really understand how you want things done. Actually, what you aren't building are solutions to individual problems, like you need to be building the process or processes for people to do that themselves, and that's a big mindset mindset shift. I oftentimes find myself actually needing to rely on people that are really good about thinking about things deeply in terms of process when, when we need to get there, because it's really not my instinct. I even sometimes find myself disliking people that, uh, really like to emphasize process, um, and you're all.

Ira:

You're so stupid, you're so why you wasting so much time, like we can fix this right now. How about you, stacey? What was sort of the leadership style at Vet2Vet?

Stacee:

So my leadership style when I started Vet2Pet actually this was something I was pretty passionate about because I was working in this vet clinic that had been acquired by a big corporate group and I had gone from, you know, kind of a small family owned clinic to like now I'm part of a bigger organization and at first it was no big deal because in this kind of business structure when the clinic's making money for the mothership, they leave you alone. But then when the recession hit and we started seeing decline in visits and the money wasn't coming in so much, they start trying to help you and I put that in quotes and that means more processes coming down and you start setting up a culture where people are not so much inclined to be free thinkers anymore and in the clinic itself, remove a corporate entity from that. But in a veterinary clinic, hospital situation or any hospital situation, you do have to have a lot of processes in place. I mean, people can't just be willy-nilly doing things all day because you're especially if you're like running anesthesia. You have to have a process on that.

Stacee:

But what ended up happening in that clinic is people felt that they were not smart enough or empowered enough or good enough or whatever, enough to make decisions, and they were coming at me constantly with all these. Hey, I have a quick question Can I do this? Hey, can we do this? Can this client do that? And I'm like come on, just make a decision, you can make this decision. And I realized I had set up a culture, or was part of a culture that wasn't cherished or valued or promoted, and so my intent with Vet2Pet was to do the opposite. I wanted people to feel empowered and capable of just making good decisions, the best you can. So that's the culture I set out to build.

Ira:

That's great and I think it's super important. It reminds me of in our relatively well sort of not earliest of days, but fairly early on, we had student representatives, students at each school that would help tell their classmates about the product offerings that we had. And we had one of our very first employees was my brother-in-law, and we wanted to get shirts for all the student reps and we'd like played around with a few ideas for different designs of the shirt and like he just sort of like made one up that he thought was was really kind of funny and cool and he ordered like a bunch of shirts without running it by anybody and and it was actually like it was really funny. But we were, we were sort of like a little bit worried about whether it might be like a little bit too cutesy and offensive, but essentially, like on the front of the shirt it's like what animal is this? And it's sort of just like a shadow outline of, like you know, a dog, a cat, a horse and a cow or something Right, it's like and, and then like under, it's like you know, vet prep, making board exams this easy, you know, since, whenever, right, and I'm like, oh you, you know, like we thought it was like really, like he's not a in the field, right um and um, like yeah, like I don't we don't really know how people are going to sort of take this as it's sort of like trivializing the fact that, like this is like the biggest exam they've ever taken in their life and it covers like everything and it's really hard.

Ira:

Or are people going to kind of see the humor and honestly, like if we debated it, I think we never would have done it. But like, since he'd ordered the shirts and spent the money, like we're like these are the ones we're not doing it again and like, thank goodness, like everybody loved them and I think we still.

Ira:

they might still make them today, like 10, 12 years later. But um, yeah, it was kind of one of those reminds like Like, yeah, I guess we kind of had this culture where if you feel like you've got an idea or a solution, like just go for it, you don't need to ask permission for everything, and every once in a while I guess that could get you in trouble, but this one didn't.

Stacee:

Well, I will tell you, it is a hard culture to implement. It's an easy culture to say you want, but when the rubber hits the road, it turned out to be very hard to actually build and apply. And one of my first experiences with this going to total hell was okay, picture it. We don't have a ton of money Of course, we didn't raise a lot of any money in the beginning and we're trying to market ourselves and everything's very tight, like when we go to these conferences and these trade shows, we're sharing rooms and we're sharing dinner. We're like trying our hardest to save money.

Stacee:

And so I had, at this point I think I had like maybe 10 people on the team and two of the employees came with me to a conference in California. I think we were in San Diego and we had a booth there and I was speaking there and you know we're working and hustling and and I had to go to a business dinner one night and my two employees went to get dinner. All right, fast forward, like a month down the road, I get the visa bill and I'm like what is this? There's like a charge for $300 for dinner and I'm like charge for $300 for dinner and I'm like, well, that wasn't me, because I I'm like being very conscious about not spending money. And uh, I reached out to my two employees and I'm like what happened here? And they said well, we just went to dinner? And I go well, what'd you eat?

Stacee:

And they said well, we had you know oysters, and we shared a bottle of wine and we had like a really it was amazing restaurant. And I had looked up the restaurant and I knew how like this is a nice restaurant. I'm like, what were you thinking? How could this possibly make sense, that you should be dining, fine dining, on our budget? And they said, well, we didn't know the. You never told us what the per diem was. And I'm like, okay, that is true, I didn't tell you. But how can this make sense?

Stacee:

So it starts uh, trickling down to like we need a process. Of course, they course it's not their fault, they didn't know how much to spend, and so how can you hold them accountable when there is no guideline? So we start to craft this process of this protocol or like here's the per diem, here's how much a logical breakfast, lunch and dinner is. I mean all this crap. And then I started thinking, all right, we have this policy now and someone moi is going to have to enforce this policy, which means I have to now review every decision that people are making.

Stacee:

And up until this point, we had not had anybody feel inclined to go spend a $300 at dinner. And so I stopped and I said, no, I'm not going to have that policy. So I put it in the shredder. I went to my two employees and I'm like, did you have a funny feeling when you were ordering the oysters and the bottle of wine? And they're like, well, kind of I'm like all right. That's the problem is, you kind of knew it was not a cool move and you did it anyways and I need you to treat this company like it's your company and I need you to understand where we are financially and help me build this company by monitoring our expenses and being like normal about it.

Ira:

I would hope like they didn't say anything either until the bill came and you saw it, like you'd hopefully be like hey, you know, we went out and we got a little carried away, like you know. Hey, just so you know, or I'm really sorry or hey, if that's not OK, I just I'm happy to reimburse you.

Stacee:

Like you know, there's a whole bunch of things that could have said or could have done.

Stacee:

Exactly and, and so at that point I told them they're like well, just tell us what a normal amount is. I said you know what? I'm not going to tell you because I hired you because you're amazing. I hired you because you make good choices. I hired you because I have a lot of confidence. You had a rough little patch here, but let me see what other decisions you can make in the future, because I'm not ready to parent you. And it worked out fine. It worked out fine, but I had to kind of set the tone there. The easier path would have been for me to lay down some big protocol which, to your point, works fine when it's a small company, but you cannot do this inside a three, or can you do? You think you could actually do this in a large company, to tell people to just be an adult here and treat this company like it's yours?

Ira:

I think it's really hard to do. I think I mean, there's a lot of theoretical ways of sort of implementing that that usually sort of come down to like well, how do you sort of build kind of small teams within a bigger team right, so that they can each sort of be managed with you know their own levels of sort of true ownership? But it's certainly I just think it gets really hard to do at that sort of scale, and I think I mean some of these things just become cultural. You mentioned sort of like you know, sharing rooms and all that stuff and sort of like we were the same way, like we're like why in the world would we waste money on, like having our own hotel room? That's like seems so stupid, like who cares, right? Um, and even as we kind of initially grew the company, you know like like our, our, you know, the person that was really the main manager of like all those things for us was this lady Katie, and she was, like you know, more worried about managing the company's budget than even the founders were Right and um, and so, like you know, she would, you know she'd stay with that Like it wasn't a big deal, like it was just kind of the way things operated.

Ira:

And then I remember we once um operated and I remember we once um we started hosting this um innovation competition for vet students called the idea, and we had these like mentors that were like helping the different student teams that were working on their ideas. And we had this event and we invited the mentors of like the teams that were in the finals to come and um, and she was gonna like not book them their own rooms? And we're like you know, like, why not? I was like no, no, like you know, like these are people that are, you know they're doing this because they want to treat them like really well.

Ira:

And and um, all the rooms that like the hotel that she'd been reserving rooms from got like booked up, oh, no and yeah, and so she's like okay, no problem, like there's other hotels there, I'm just gonna book another hotel for them. And we're like great and um. And then, like a couple weeks later, we're looking like how come you got this room at this like shitty hotel? And she's like, well, like the other ones were like 500 bucks a night and like that was the only one that was affordable. Like well, who's staying there? She's like it's Dani McVety like the co-founder of Lap of Love.

Stacee:

You put her up in a shitty hotel?

Ira:

And I was like, oh, my God, we can't do that. But we're like, okay, well, now what do we do? Like you know, like she's already like emailed her the hotel information and I was like, I mean, like I would trade rooms, like like, but I'm staying with the other, like I don't have my own room you're sharing I was like well, if you'd like to stay at a nice hotel, you could stay with mauricio and steve, uh and um and so she was, so she was probably totally understood you know, like, well, this is like a confession, like I don't think I've ever told anybody this story, really Like, like we just like we're like well, I mean, like we like hopefully it's not that bad, and like you know, like let's just not make a big deal about it.

Ira:

And she never complained, of course, but, like you know, we went to go like pick her up, you know, for whatever it was, and like it wasn't as bad as we sort of imagined it might be, but, um, it was just sort of one of these things like, yeah, like you know, certainly we didn't feel the need to micromanage any of those decisions, but you realize, like, oh, yeah, like the way that we've kind of done business internally, like once you're sort of like a little bit bigger and like there's different people, like maybe it would be really weird for somebody to say like, oh, of course you're gonna share a room with somebody, or you know, um, have you know people that are not, you know, both of the same gender in the same?

Ira:

like you know, I like people oh yeah, it starts getting complicated I do need to say, just in case she listens or finds out about this I'm really sorry, Dani. I lost a lot of sleep over the fact that everybody else was staying in this nicer hotel and you got put up in the other one. I tried to think of some way to sort of resolve that issue and I've been embarrassed about it for probably eight years, so hopefully you'll forgive me.

Stacee:

You need to buy a room at the Hyatt for the upcoming movie Like the Ritz or something All right. Well, now we're at the part of the show where we'll share a favorite tip, tool, quote person insight. What do you have for us today?

Ira:

Continuing the trend of embarrassing and exposing myself.

Ira:

I want to mention a tool that I think everybody else in the world probably already knows about, but, for whatever reason, I never really used it much until the last month or so, and it's because one of the things I'm not any good at is anything related to trying to make something look nice, and so I've always had people that are good at making things look nice make things look nice when I need them to.

Ira:

But, for whatever reason, I have had a number of projects that I've started doing in Canva and I was like, oh my God, like this is actually pretty easy for a design list nerd like me to make something that certainly doesn't look as nice as an expert can make it look, but makes it look a lot nicer than anything else I would build in, you know, powerpoint or any similar sort of tool, and it's actually kind of fun. So I've been having a good time doing a lot of things in Canva, and I speak very highly of it, and so if you, like me, are like I don't do that type of stuff, I don't need Canva, you might want to check it out. It's actually, you know, sort of. It probably has more value to people like us than to people that are actually really good at design.

Stacee:

Oh, it makes it so easy for beginners. I mean, they really set you up for success in that program. They even tell you what color schemes to use together, so you're not left to your own devices. Tell you what color schemes to use together, so you're not left to your own devices. My tip this week is going to be a software tool called Tango, and if you Google it it's tango. us, not com. And what Tango is is it allows you it's like a plugin for your Chrome and you just turn it on when you're doing a task on your computer, like maybe you're going through how to set up an account for something, and it automatically captures screenshots as you click your mouse and puts the screenshots in sequence with the URLs. So if you're flipping webpages or whatever, it builds out a workflow for you.

Stacee:

So when we're talking, about processes today and you need a process, or you even just need to document how to do something for because you're cross-training a colleague or you're trying to help a customer out it just is so quick and magical, and then at the end you get a URL that you just kick over to someone and it's basically here is the recipe and here are the steps to getting the cake. So that's a great one.

Ira:

Pretty cool, all right. Well, I suppose we need to spin the wheel of names to figure out what we'll be talking about next time.

Stacee:

All right, let's do it. How did you gather feedback on your product? And iterate.

Ira:

Great question feedback on your product and iterate. Great question. Super important to do and sometimes hard to get from the right people. So good question. Happy to talk about that.

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