Looking for the patterns in your marketing with Kate Bradley

In this week’s episode, we talk about everything from entrepreneurship to employee happiness. (@LatelyAIKately) Kate talks about the pressure on a start-up CEO and how it is compounded by trying to run a successful business and raise money at the same time. Kate reveals one really cool new feature on Lately.ai. (You must listen to the end to hear the big reveal!)

What you will learn from this episode and about Kate

• Passion for floating in a pool and listening to 80s music

• CEO of Lately, an AI that repurposes long-form content

• Focus on making fans, not sales

• Educated on Black American perspectives •

White Elephant in the Room: lack of diversity in podcast

• Advice to never assume what any side wants

• Value of lifting others up

• Making a fan creates a machine

• Marketing is about getting a fresh perspective

• Overuse of words leads to dull communication

• Creative use of language to engage people and make them react

I absolutely think that people who are focused on clock punching rather than performance and outcomes are missing out. Clock punchers are focused on the wrong thing and don’t understand the bigger picture. They don’t see how their work fits into the bigger picture and how it contributes to the success of the company. Performance and outcomes are much more important than just showing up and doing the minimum. If an entrepreneur is focused on performance and outcomes, they will be able to make better decisions and find more success.

Kate Bradley

Kate is the Founder & CEO of Lately. The A.I. that learns which words will get you the most engagement and re-purposes video, audio, and text into dozens of social posts containing those words.

Kate is a former rock ‘n’ roll DJ and served 20 million listeners as Music Director and on-air host at Sirius/XM. She’s also an award-winning radio producer, engineer, and voice talent with 25 years of national broadcast communications, brand-building, sales, and marketing expertise. What she learned in radio about the neuroscience of music helps fuel Lately’s artificial intelligence.


Brent: Welcome to this wonderful episode of lately on Talk Commerce. I have Kaitlyn from lately today. Kate. Please introduce yourself. Tell us your day to day role in one of your passions in life. 

Kate: I formally was a rock and roll DJ broadcasting to 20 million listeners a day for XM. So I have a soft spot in my heart for podcasting, of course. I love the theater of the mind so much. I love radio. I love that you Brent have this I don’t even know if you know that you have it, you have this beautiful power to create what I call a two-way street, even though it’s one way.

Kate: I You wield the microphone here, but people listen and trust you and they lean in because you have this ability to create that magical kind of feeling as though they’re part of the conversation. And so that’s what attracts me to radio and podcasting specifically. And I don’t miss it.

Kate: Cuz can I swear in your show? I don’t know. Yeah. Go for it. I had a shit time. there, there’s great things about radio. I met my husband there and his record was our favorite record of the year. And of course, total job hazard. Cause I dated musicians do not recommend, found the one good one, who’ve cut his hair and wears chinos and now he’s. Sales bless his heart, but radio is a boy’s club, of course. And me too, and all that stuff didn’t even exist. And the rewards you got for participating in sexual harassment were large. It was applauded. And so we all did it, and I, not only, and I was a recipient of course, because, I don’t have a phase for radio.

Kate: Yay. And there’s no women either. So of course, like every day my boss would ask. Bradley or your hands queen, meaning could I hold this Dick while he peed? just, it was just the locker room bullshit. So that. Bizarre because what started happening? I don’t know why I’m going down this thread with you, but Hey ladies, listen up the the sexual harassment turned into a hostile work environment because of course I was great at what I did and I arranged.

Kate: The first ever marketing newsletter for any of the channels, it was ours. And it got all of this. This is before MailChimp. Okay. So I was like in outlook having to send multiple copies because you could only send it to 250 people at a time. Remember that there was like no formatting. And I got us. Just a huge amount of press.

Kate: Just because I’m a bulldog, and I was like I think we should do this. And I’m gonna ask all these people to republish it and forward it, et cetera. And they did. And and then I got shit on for my success. So that was confusing because you’re like, I’m killing it. Why aren’t people excited about this?

Kate: It’s because they’re threatened. And I dunno if that’s why I have my own company and I don’t have to deal with. Ego, except for my own. now , the mountain. What were the other two questions you asked? 

Brent: What is your day to day role and one of your passions in life?

Kate: Oh we might have covered the passion but I think at the moment, my biggest passion is floating. I love the weightlessness of floating in a pool and we have a kitty pool and in text one, thank God for those people democratizing this thing, and we’ve had one for a while. It’s 12 feet by four feet, maybe three.

Kate: And there’s just enough room for two people to float. We built a solar heater out of black hose and a black piece of wood and a there’s a pump. And it does when there’s not a heat wave. It’s usually 88 degrees, which is what I like Brent, and me and my noodles are out there just floating away every day.

Kate: I’m allowed three songs, so I bring the Bose out there and I listen to three songs on the radio. Actually, I can still tolerate live radio and by tolerate, I really mean that cause it’s. Fucking terrible. Really terrible, but there’s this one station here that they mostly play 80 songs with and I’m a child at the eighties.

Kate: So I’m like, Hooters, Eddie grant, Steve Miller. Yes. And sometimes I’m lucky and I get three great songs. Sometimes they throw in some, another seventies, crap like BGS, or I don’t really like Harry Nelson, stuff like that. And I’m just like, I’m just waiting for the next good one. But that’s my passion at the moment.

Kate: And then. Who am I? What am I doing? I’m the CEO of lately lately uses artificial intelligence to repurpose long form content like text and video and audio into bite size social posts that it knows very specifically, which parts will get you the highest engagement. . 

Brent: Yeah, that’s great. And I am a, I’m a user of lately for longly.

Brent: It’s been a great tool for us. I do want to just dip back into podcast guests, because it’s not always a two street. And when people come on as a guest that are, that have an agenda that are trying to. They are not a good guest. And I sometimes just look at the clock and think, oh my God, can this 30 minutes be over?

Brent: And now the 110 guests that I’ve had are thinking, are you one of them? Kate, you are not because this is the second time you’ve been on and I really appreciate you coming on. But it is sometimes difficult and it’s, my, my job is made much easier. when the guest holds the conversation, but it’s not a sales pitch.

Brent: And I, there’s nothing more than I hate in a sales pitch from a guest. But anyways, this is my pitch for lately because it is, it’s such a great product. And I’m falling in love with AI. I just signed up with open AI. I would I want want to get into the Dolly thing and there’s so many fun things happening in.

Brent: That I’m very interested in. But I do wanna talk a little bit about some of the entrepreneur journeys you’ve been going through and also, in our green room, I do wanna just bring up the white elephant in the room, which is me. And we did talk a little bit about, and you brought it up too.

Brent: The fact that there isn’t I don’t have a lot of diversity in my podcast and I would like to work on that. I’m part of the entrepreneurial community here in Minneapolis and Kate. I was just educating Kate, when we, before as well, Minneapolis is a city in the middle of the country.

Brent: And I know people on the coast don’t realize that there’s a part. World that between New York and California, but we don’t have to go into that. So I’m on I do sit on the diversity and inclusion committee. and I always ask myself, why should I be on this? And actually if I had some good guess, and they’ve given me some good answers on why me as a white male should be on this.

Brent: And part of it is just awareness and talking about it, because if everybody doesn’t talk about it, then it becomes something that’s back room. And I think it’s always better if we do talk about it. So not to belabor the point, but I know that there’s challenges in that. There wasn’t even a question 

Kate: in there.

Kate: I have a comment though, if you don’t mind. My friend, please, Jen. God, what’s her last name? Vander something, sorry, Jen. Vander. Awesome. I’m just gonna call her that. So she, we were on a panel once and she. express this in a way that was the first time I got it, which is this, when you are the underdog, you can only be lifted up by those who are on top.

Kate: And the mistake many people make is not including the people who are on top in the conversation and we rely on them to lift us up. So in your case, it has to be white men in the conversation because they hold the power in the world. They. For the most part. And not excluding them is just a stopper right away.

Kate: So I get that on the, just a flip side and we should go into politics cuz that’s dangerous. But I did, I was a marketing consultant for a company called the perception Institute for about a year and their mission in the world or a nonprofit is to change the way that black men are portrayed in the media, black men.

Kate: And. . And so I learned a lot about people, about black Americans specifically and how they feel about white people of intervening in their business. And it was mostly not nice, which was interesting, and the overall reaction was like, stay out of it with your woke perceptions. Because what you think is right is not what we believe at.

Kate: And I’m generalizing. So forgive me there, but just a perspective, like it’s the S U right? You have to never assume what the other, what any side wants. Everybody has to be at the table for the magic to happen for the two-way street to happen. Let’s get back to that. And the second comment I had related to that was.

Kate: You touched on what makes for a good guest, so I believe it or not, I was a terrible interviewer on radio for a long time. I would get very nervous and I was young. And so I didn’t have a lot of experience, doing that. I was, it was the me show. I was great at the me show , I didn’t know how to make people shine or ask the right questions, cuz I was so nervous about pushing all the buttons and getting things right at the same time. Cuz you’re in my day you were managing like the whole show, just like you are with your podcast. So there’s a lot to do behind this in the green room, as you’re saying.

Kate: So to tie in what makes a good guess is when you are able to lift others up. Number one a and that’s I think that goes both ways, but as an entrepreneur. what we say is make a fan. Don’t make a sale right now. The value there might sound corny, but I believe in the long tail, this is the radio that I grew up in is all about the long tail.

Kate: The album cuts, not the hits, right? Get people to buy the records, make fans who are loyal to the death. And I saw the power of those people because when you make a fan, they work for you for free and they can’t help the. And so you get multiple banks for your buck because you make the sale and you make a machine, 

Brent: right?

Brent: Yeah. No. And I really apologize for what I’m gonna say now. because I do feel like now I want to change the name of my podcast to ceiling. Because I would love to get ceiling fans but keep going. I know. I’m sorry, Brent. that was so bad. Hold your nose, 

Kate: everybody. 

Brent: Yeah. So I, my wife and I had this conversation about ceiling, the Mar Marcia Beski talked has a song about a hundred tampon.

Brent: And in, there was there, there was the first lady in space. They gave, she was gonna be in space for a week. So they gave her a hundred tampons and and she has a she’s on Ted. She has a Ted talk anyways. So they, she talked about the fact that she has this song. And then all of a sudden, all these men started berating her about, you shouldn’t make fun of these engineers at NASA.

Brent: Like who knows, like you, you need a hundred tampons right. For a week. And it was, we had a very good convers, my wife and I had a very nice conversation about it. And I, for me, I thought it through and I’m like, yeah, that doesn’t really make sense. I don’t, I don’t know any better, but her point was, there was a lot of men that came out and were.

Brent: Hit Eric making her feel bad that she’d come up with this song or not making her, I don’t know the right words, but sounds funny. They were ham whatever social media, what social media does, that’s what they were doing. 

Kate: I have a segue 

Brent: for this.

Brent: Okay. Yes, we need a segue. Yes, go. 

Kate: So one of my favorite lines is Catherine Hahn in. the, we are the Millers when she calls it a Tanin and she’s from the Midwest. She is in this movie anyways, and so around my house, it’s called a Tanin and we laugh every time cuz it’s so funny to us, but that’s that ability by the way to take so.

Kate: and spin it in a new way, which is really what our jobs are about. This is marketing. How do you get fresh perspective? Whether it’s a hundred tampons in space or throwing a hot dog down a hallway, as she says, right? There’s I love that. I love. we, I just did a post on LinkedIn. I don’t know why I was inspired by somebody on Twitter.

Kate: And I said, words that make you like wanna bar. And I said, I’ll start. And the word was trousers. And so everybody piled on with not only just words that they don’t like the way they sound moist, got a lot of votes. For example, salacious got some. But then also biz lab was all over the place. So people were like partners and utilize at the end of the day, like all that kind of 

Brent: stuff.

Brent: I’ll reach out to you later. Yeah. 

Kate: Yeah. So I was just thinking about the, how we. how we can overuse words to death. So they don’t mean anything like awesome, which I am guilty of as well. All of America overuses. Awesome. But the whole point of communicating well is to don’t only communicate well, but to communicate with meaning.

Kate: and to hear some biz bla drive engagement, to make people lean in is to take something very familiar and just turn it just enough so that somebody is you catch the ear and you make them react. It’s the reaction that we all want. And I love thinking about that. I love so my husband is great at this he’ll he has all these isms one.

Kate: The hammer lane and the granny lane. That’s what he calls the fast lane and the slow lane on the highway. Or dirt nap. That’s like obviously dying 

Brent: dirt nap. Okay. 

Kate: Or booger sugar is cocaine , which we were just watching that Tom cruise movie American made, which is a great movie, by the way.

Kate: Even if you don’t like Tom cruise, it’s a 

Brent: great movie. I agree. I’ve seen it. Very good. Okay. Alright, so let’s move into little, let’s talk a little bit about entrepreneur entrepreneurship. My daughter just got a job with a CRM company called endear and they’re based outta New York, a very young entrepreneur lady who started it with a partner and te.

Brent: Did you have any struggles as an entrepreneur? 

Kate: oh, so many. I think the one that’s ever present for me is it’s, I don’t know if it’s confidence I, I don’t have an imposter syndrome per se, but I take things personally, that, that whole. Bullshit about it being work and business and not personal it’s it is bullshit, to me it is of course it’s personal, it affects people’s lives, right?

Kate: I That’s, it has to be right. And I’ve had to make decisions. I’ve had to let people go. I know how all that, how hard that stuff is. But I,

Kate: the pressure that I put on myself is pretty sprint. I perceive that there’s pressure being put on me by others as well. That may or may not be true, but there’s certainly that there’s that perception whether it’s my customers, like I wanna succeed for you. Whether it’s other women entrepreneurs, my investors, my fam, my family my team, obviously Lauren and Brian and Kristen, Jason and everybody, Kristen and Katie, Greg, I think that’s all.

Kate: Did I forget anyone, Emma Alex , and I, the problem is I don’t know what failure looks like. So let me just put this in the ground for everybody. We’re bringing it down. Brian, my CTO is very good at being positive and PR and practical. He’s an engineer. So he, he, he shoots pretty straight and I’m always.

Kate: wallowing in the negative. And he’s dude, like you have to really understand this, the odds of what lately is. So the chances of startups succeeding at all is already ne it’s negative. The fact that lately still exists. The fact that we have revenue, that we have hundreds of customers, we’ve had thousands before, we’re figuring out how to do it all here.

Kate: He’s like lately should have died a million. So you really need to acknowledge this, but it’s not that I don’t acknowledge it. It’s that the road to getting to the next level, like the levels, the goal post move a lot, which is very frustrating to me. Like I’m trying to figure out Brent constantly not how to win the game, how to beat the machine.

Kate: Okay. That’s all I think about how do I beat the fucking machine? Beat it into the ground. That’s what I. That’s all I see. And it’s not enough for me just to have a nice little business here. That’s not the game I’m playing, right? That’s not this game. And when you do everything that’s prescribed and you do it like to the fucking awesomeness of awesome platinum level superstar, galactic awesomeness, which is what we do.

Kate: And you still can’t hit the milestones. That’s defeating debilitating to me personally. I take it personally, cuz then I think, what’s wrong with me? Why can’t I fucking do this? And I hang my head in shame, honestly. The buck stops with me. It has to be me. It’s not I can, there’s all, there’s the great resignation.

Kate: There’s, COVID, there’s the market. There’s all these things to blame, of course. But I don’t think of any of them. It’s always hard. There’s always some shit out there. So it’s me. I’m the one where that can control. What’s happening or figure it out. And, I think just generally that’s the biggest hurdle is my, is myself in a way.

Kate: I don’t have an off button, cuz I want this. It’s not that I want this so bad, but I know it’s I know it’s not even possible. I know it’s probable. I.

Kate: And so I also, that means, I know all the pieces are in front of me here already. I know that they are, this is a matter of assembling the pieces. I have the right. Is which is a blessing and a curse. It’s right here. But the fact that I can’t figure it out makes me feel like an idiot , and none of that’s true.

Kate: I rely on you. I rely on our customers. We’re always asking for feedback. I’m terrible at taking criticism, but my team is great at it, which is why I had them, and we’re always looking for ways sorry for rambling but entrepreneurs, here’s a great tip. Someone told me, and you get a lot of tips that are garbage, cuz everybody wants to give you some advice.

Kate: But a friend of mine said, look for the patterns. So if you can look for the patterns in everything, whether it’s the way the funnel works or how much MRI you’re making or what customers click first, right? All these little patterns are macro and micro patterns. You can double down or then fix them.

Kate: and my, I joke all the time. My, my great skill is seeing the glass half empty. That’s what I do. I look for problems, patterns of problems, so can you imagine being my husband? He’s a nice guy. 

Brent: yeah I am. I am the glass half full and my wife is the glass half empty. So we actually balance each other out.

Brent: We’re either full or empty at the same time empty we’re empty. So I definitely can empathize with your struggle. And I do of want to talk about as a leader that empathy part that you have to have for your employees do you see a difference in differe? Styles of leadership that work or don’t work, or I don’t know.

Brent: I I see sometimes that some entrepreneurs want to like they assume that your employee feels some way and if you feel differently, it doesn’t matter to what it’s not it, the feelings of your employees don’t matter. And I feel like that I’m I believe they matter, but that some of that empathy isn’t there in a lot of entrepreneurs.

Kate: I had a shitty job, so I know what it feels like to have that kind of panic attack and go to work and dread every day. And I don’t want to any make anyone feel that way. I am very lucky because all of those people on my team are very kind and they’re very loyal and they’re also very smart. I forget sometimes.

Kate: That they can’t read my mind. I try to apologize for that. Luckily they have a high tolerance for my bitch. That’s ano very lucky thing, because I can be an asshole. I can be, of course, and I’m so grateful. I have to surround myself with people who have that tolerance because I.

Kate: Always apologize for it. There’s too much to go on, but I have to also obviously reward and acknowledge. And so I need also the kinds of people who either don’t need that all the time can get it from each other. My re I feel my perception is the reward is to provide a workplace that is fun, which it really is.

Kate: It’s we have like unlimited vacation, no one ever takes a vacation. I don’t know why they don’t, but they don’t. You can, you don’t have to ask to go to the doctor or anything. You just, nobody cares. Get the work done. We don’t really care what you’re doing during the day. If there’s. And everyone is very autonomous.

Kate: There’s, some things I’m a micromanager about. I know this, but my aim is to not be that way and to, to a fault, honestly, like sometimes I’m trying to figure out why these people, these two people, maybe aren’t getting along or hearing each other. And then I realize , I don’t bring them together enough.

Kate: cuz we’re all just out doing our own thing. We’re running and running. And one thing sometimes I forget that. Because we’re, know, we are dispersed and we always have been dispersed and I like that because I feel it’s so much more productive. I hate being in office when people are coming in and talking to me all the time.

Kate: I hate that. I can’t get anything done, and. , I will forget how smart they are. I’m like, shit, Chris has really good ideas. I need to ask him these questions more often and then utilize them, or Lauren is, I think she’s 15 years younger than me. I forget, but she’s younger than me.

Kate: And I forget that she is because she’s so 

Brent: she’s 10

Brent: And I talked to Lauren. Lauren is fantastic by the way. Isn’t she great. Keep going. Sorry. Yeah. She’s didn’t mean interrupt to you. 

Kate: No, I’m sorry for she’s so smart. And my, for all of them, my expectation is I, these people are on a scale of one to 10. They’re twelves. They’re all twelves. And so when they’re only tens, I get on their asses about.

Kate: Shame on me. Because I believe in them I respect them and I’m so impressed with them. And Lauren is certainly one of those people, and but she can tolerate my shit, which I, that this is also what I appreciate. So the way I try to reward, money is not the thing that motivates my team because.

Kate: We often can’t pay each other or the salary isn’t very high, but I try to create a workplace where there’s like a ton of flexibility and a ton of autonomy, because these are the things that I need personally. And I know there’s people out there like me, and I think to providing a safe place, like I call it where people can be themselves.

Kate: Like we don’t, we don’t really have a lot of rules, the golden rule, our biggest rule. And. a lot. We have two meetings a week, one for sales and one for the whole team, cuz we’re small enough. We can do these things still. And at those meetings we have what’s called the rolling agenda. And so the rolling agenda is a Google doc that goes on and on for years and everyone’s name is on it and you’re supposed to write what you’re doing, what you’ve done and what you’re doing there.

Kate: And everyone reads it an hour before the meeting and at the top of the meeting is the actual agenda discussion items. And the discussion items are the things that we all actually need to talk about together. Cuz I don’t need to have a report of what you’re doing and plus I can see it all in slack. Our slack channel is I don’t I poo threads because I want everybody, I want it to bleed over for everybody.

Kate: It saves me the time from repeating myself from silo to silo and it makes everybody sympathetic or empathetic. And so the rolling agenda what’s so funny is there’s almost never dis any discussion items cuz we’ve already had the discussion. So it’s a hang we get on the phone and we find out that.

Kate: Chris’s son, Zach just performed at a comedy club and killed it with amazing jokes. A couple of Dick jokes, in front of his grandparents, but I guess they were killer. Awesome. Katie’s daughter, Ruby just scored some major role in a play. I think it was beauty. The beast she’s the lead, which is pretty great.

Kate: Kristen’s getting ready to go to Paris with her two children. For the, and her husband. So the first family vacation and maybe the last one, cuz everybody’s going to college, this is what we talk about, I love that about them, Brent, how lucky am I? 

Brent: Yeah. That’s building a team like that is, is like the dream of any entrepreneur.

Brent: It I think you’ve talked to a lot about, about that team building and how you’ve been successful in it. What would you. If you were gonna say something to an entrepreneur who was hung up with instead of that mentality that you have for performance I don’t care what you do all day, just so you deliver what we’re expecting.

Brent: The opposite of that is I, all I care about is that you come in and punch the clock. right there. There’s a dichotomy there and there’s a big swing, right? If you’re just assembling something and you’re punching the clock, you know what you get because you’re assembling something.

Brent: But the same thing is you could come in and assemble something very poorly. Or, if you’re not checking, there’s gotta be a balance between performance. I’m a firm believer in performance and the outcome of that. Do you think people that look at clock punching, miss the outcome part? 

Kate: Sure. I’ve been that I worked in retail in the mall.

Kate: I know what it’s like. it sucks. And I hated it. Sorry, dad. I worked for my dad for a while. I love my dad. I think, so like begets, like when you are around other people who are working at a superior level and you’re not, it’s obvious and you feel bad and you want to catch up. So that’s one thing, right?

Kate: And I’ve surrounded myself. I’m very lucky to have these people who are, these are amazing people. Please never leave me please. And I’m always concerned when, like one of them, if someone’s gonna get married, Girlfriend moves in or something like that. I’m like, is my productivity gonna go down?

Kate: It’s so mean, that’s my first thought. Then my second thought is I want joy for this person. Hello. What’s wrong with you, Bradley. But I think that I think we were saying earlier, like the work life balance is bullshit. Like work is life and life is work. And if you’re not having a great time during what you’re doing, you’re not feeling fulfilled and joyful.

Kate: and like you’re doing something to improve the world or yourself, then you really need a different job. I It’s so important. I think, for entrepreneurs, the objective, I always think, and I think about this, especially when I’m like arguing with my husband is what is money? What is the outcome that I want here?

Kate: What’s the outcome. So let’s back into it is the outcome to make someone feel wrong because they fucked up is that the. that you want, you wanna make them feel bad. So then they don’t sell shit for you all day long. Cause they feel bad and they’re done. I’ve done that before. I’ve done that. I like making PE people feel wrong.

Kate: Like I do. I like calling them out on their shit. I’m trying to go to therapy to improve this, but it’s there, it’s the thing. And I, but I’ve learned not to do that because what is the point now? Now sometimes you have to correct someone on what they’ve done in order for them to improve.

Kate: I’m not great at this, but I, that is my aim, Poor Lauren. She, I like people to write copy for me. So we’re always, we work together on sales. And so she is in charge of the follow up with the sale, right? So we have a call. We have to email them, she’ll draft an email and Google I’ll take 95% of it apart and rewrite it and then be like, okay, here you go.

Kate: Now her feeling can be defeat defeated, like thanks for wasting my time. I explained to her, I was like, you don’t know how much time you saved me just by starting this. And my point of taking a part isn’t to shit on you. My, my point is to give myself something to play, where I can move around.

Kate: And I said, this was a, like earlier last year or something. And I was like, I will do. I promise to do a better job of telling you why I’m rearranging these things and what, why I’m putting these things in here. If you wanna learn how to do it better, but at the same time, I have to remember.

Kate: Lauren came from she. So she has a she’s smarter than all of us. She has a master’s degree in psychology analytics. And she came from working at the cancer ward in a hospital, God. And took the first job at lately as head of customer service, which she killed it at. And then she ran our sales team and now she.

Kate: Chief operations officer. So she has some very deep legacy knowledge of the company, but she didn’t come from sales. That’s not her background. None of us actually have come from sales me the most. I have the most experience in sales and we have a 98% sales conversion. Brent, Kristen come from sales.

Kate: Chris comes from radio like me,

Kate: the reason, of course the product is awesome, but we. Fucked up that demo 50,000 ways sideways to Minneapolis. Okay. I’ve seen it. Me too. And the demo does sell itself, but it’s the people, it’s the people that sell it. And it’s because Lauren, her ability to read the room and by the room, any room in a room, an empty room on a camera, in a zoom call or a room full of 85 people at SAP.

Kate: Like she has those nuances. And that, and Chris has the same thing as well. These guys this is about being nice, right? It’s about being thoughtful. It’s about listening. It’s about they know both of them are, I’m talking about them cause they’re my chief salespeople specifically, but like they can stand on stage any kind of stage, whether it’s just a call or actually on a stage and lead a room, they have that capability to do.

Kate: But at the same time they know when to listen. I don’t have that capability. I just like to be on stage and hear the sound of my own voice. Sorry.

Brent: So what would you say to To an entrepreneur then that is that they’re building this team and they’re, they seem to be getting a lot of turnover. Is there a magic formula in that team building model or is there yeah. Something to create community or is there anything that somebody could start.

Kate: I think the first thing is just to really think about how you wanna be treated. That’s just the most important thing. And that’s very hard cuz like you’re trying to get shit done, so you have to be very reflective constantly and to not just how you wanna be treated, but when you’re at your best, when you’re in the zone, right?

Kate: What are people around you doing to facilitate that for you? And then try to replicate that? I think that’s the first thing I. the second thing is to know this is so important. You have to ask people about their fucking lives, right? There are so many times where I just wanna get the meeting on and get stuff done, but I don’t, I make sure, Hey Brian, how was your trip?

Kate: blah, blah, blah, blah, blah. Oh, Hey Jason, I saw that me is on Instagram and she’s like doing this whole abs routine. She looks amazing. What is that about? So he’ll tell me. You have to start that way. People want to talk about themselves. Obviously look at me. I’m someone who talks over people, Brent and I have no patience for people who are offended by that.

Kate: Honestly I believe in passion and I believe in the power to express your passion and that an interruptive culture should be celebrated because people are so excited to share their ideas.

Kate: and I don’t believe in democracy. Lately is not a democracy. I’m the leader. Although you have to make people feel as though they bring listened to right now, you can only do that with people you wanna listen to. So if you’re hiring people, you don’t wanna listen to, then you are an idiot, you’re, you have to really think about who you’re.

Kate: And we’ve made mistakes. Lauren will know, and she rolls her eyes and she tells me every time and I still make this mistake. I constantly think we need an experienced salesperson to come in here. And so I hire these fucking dudes. They’re always dudes. And. some dudes. I love they’re some of them are dudes.

Kate: I love some of them are dudes. I don’t love, and it never works out because they’re probably bold 

Brent: white dudes. They’re the worst 

Kate: is that where, how was, yeah. Or so one mistake we made by the way, which I didn’t know, this was, you cannot hire a salesperson to be both a manager and a salesperson.

Brent: Yeah. Very true. Absolutely. You can’t hire anybody to be either to do dual jobs. They’re gonna do two jobs poorly. 

Kate: Yes. And that is a mistake that I made. I didn’t. I do that. So I don’t understand why someone else can’t do that, to be honest with you. And Lauren does that. There are Brian does that.

Kate: I have superior people in the world who can do that. So it’s of like why, but it’s not everybody’s nature, so I think that’s the first thing a very easy tell for us is this is if your company, if the PE, if your employees aren’t saying. you’re doing something wrong. 

Brent: Yeah. If they’re saying you Kate, that then also you, and I’m, they don’t because I’ve talked to your employees.

Brent: If they are though, just always referring back to you, that’s also could be a problem. 

Kate: I do that by the way on purpose. So I rarely, I don’t like it when people call me the boss, I correct them and say, don’t say that I don’t like. I say we all the time, my team I rarely say my employees, I rarely do.

Kate: I need them and I don’t like the word need, this an needy team is needy, but I cannot live without them. And so they know that

Kate: I send them gifts often, like little surprises, even the. Some T all guys like pocket knives, you can give them endless pocket knives. Am I right there? 

Brent: send ’em a box of tampons. A hundred figure out what to do with these . I do, I want to just go back cuz I you talked about re you’re editing Lauren’s copy when she started it.

Brent: And I think that and it sounds like you explained to her. Why you’re doing it, I’m trying. Cause I think a lot of times a lot of times leaders will jump on they’ll just take it and they’ll do it, but they don’t give any feedback on why that happened. And that just leads to narratives in people’s heads.

Brent: And I think 

Kate: I made that mistake actually, because I assumed that she would understand and know right. And I assume that she would take the time to read it and think about it. But of course, Lauren is busy and she’s just trying to check shit off her list and get, cuz she’s the queen of productivity.

Kate: She knows that. I respect that. And so either one of us weren’t both of us, didn’t want to take the time to do what you just said, which is a very important thing to do cuz who can learn if you don’t do that. And. , know, like I said, why can’t someone read my mind? What the fuck when it’s so obvious to me, but I’m sure at the same time, she’s thinking why can’t Kate read my mind. 

Brent: So yeah, I, I have definitely got, I’ve gotten into the habit of explaining I’m always now trying to play chess with Anticipating the way somebody’s thinking. And I realize that people that are happy are more motivated and that they’re gonna be more productive when they’re motivated and that when they’re happy and productive, they’re gonna get a lot of work done.

Brent: So if I’m gonna be critical of somebody, I would like to explain all those reasons why that’s gonna. and I maybe now do it to, is the word in nauseam or something like that where you do it too much. Yes. Ad nauseum, whatever in nauseum I’m nauseous. Just that, that verbal feedback, because I think we do I also suffer from that same thing.

Brent: Of course, everybody should know what I’m thinking and yes, everybody can do this. Everybody can be a great salesperson. They can also be a developer. I fall onto that trap because I used to be a developer and I would. Of course, you can do that in AWS. I can do it in 20 minutes. Let’s watch me do it.

Brent: And everybody’s oh God, this is the worst time of my life. You can see everybody’s eyes are glazing over and pretty soon, like they’re, anyways, so to read the room, right? Yeah. Read the, yeah. And then it makes it worse on zoom, all everybody’s camera goes off and then you get done with your demo.

Brent: And then, so what did everybody think? And nobody’s there, it’s silence. Everybody’s gone to the bathroom. Oh, I’m sorry. And then one person leaves the mic on and the flush sound comes out and your zoom call was ruined or saved yeah. Or saved exactly. 

Kate: yeah, I think I oftentimes I wish people would ask me why I do.

Kate: and they don’t. And so that, that is frustrating to me because I want the initiative to, to be there and that’s, my problem is that’s why I’m the entrepreneur and these other people are not right. That’s a different skill, so I have to constantly readjust my perspective to reality and think about.

Kate: What’s gonna, what’s gonna get the job done. Like you said, like, how do we get people to be happy and motivated and successful all at the same time? I think that

Kate: it’s important to ask people. Do you like working here? Sometimes you, I brace myself for the answer. You still like working here? Are you leaving? I just wanna know. I think that. knowing what your weaknesses are really important. Like I said I’m not a great cheerleader, but Katie Jordan is, she’s amazing.

Kate: She does it for me. And Chris is great at that. Everybody is there everybody piles on, but you need a cheerleader on the team if it’s not you that bubbly. When, when Lauren’s on vacation, slack is quiet. And you feel that energy gone like that. It’s so important. She she doesn’t even real.

Kate: I don’t know. She realizes that she probably does that. How. Much that energy. Slack is our workplace, right? That’s our work environment. And so it’s the, you can see the thermometer of how things going now. When I like last week, an investor who had hard, committed first to a smaller amount, and then to three times an amount hard commit pulled out for no reason.

Kate: I just was like, mother, fuck. I said every swear word of the thing like that could be. And no, I don’t do it in the general channel. I just did it with Lauren, Jason and Brian because I don’t wanna upset everyone else, but I need them to know cuz they’re my they’re. We are running the business together.

Kate: We’re running the numbers, we’re looking at all these things, but Brian and Jason are co-founders like, they do need to know what happened with this investor. And I need the ability in a place to express. Frustration. I also need them to have sympathy for me because like, when I have to ask them to not have a paycheck, they need to know exactly why, and I’m not doing it on purpose and it’s not cuz I’m selfish or I’m money grubber, there’s a real reason and it’s very painful for me.

Kate: So that sympathy, empathy thing here I think is so important. Like I’m just a person, Brent, I’m trying to do this thing. and they are these people’s lives are in my hands a little bit. Cuz a paycheck is a paycheck. I 

Brent: Yeah I want to just jump on that happiness thing. I had a post on LinkedIn recently that I just put out there.

Brent: I meet with every person on my team every quarter. one on one, just for 15 minutes to get to know them. And we have team members in India and Mexico . I do that and I’ve always had this. I’ve always had a question that I’ve asked and I think I’m asking, are you happy in your job or something like that?

Brent: And I been thinking about it and like I was thinking like does anybody ever ask, are you happy? And period, because yeah. Are you happy period? Because there is. And maybe happy in your job or happy, whatever it’s different. And knowing if you’re happy, if you’re not happy.

Brent: Again, people probably aren’t gonna tell me in that short time, hopefully, maybe over time. In fact I recently did have an interview that I did where he said that I’m very intimidating and it’s hard. Like you had said, you want people to tell you the things that like if they don’t understand something and I think people don’t tell people things because leaders can be intimidating.

Brent: I can get very impatient and then become very I can be an asshole. And and especially when something going the way it should go and. I’m gonna assume you can relate with this. This is something that’s so obvious. Why aren’t we all doing this? Whatever that thing is oh my God, this is obvious. We should know this. You always get French fries at McDonald’s what thing? Yeah. Which I don’t, it’s the thing I don’t, I’m just making the insane, but it’s come on, everybody knows that in. As you’re driving on the freeway and you stop and you get a burger, you get fries, right? You get a Coke and a fries. Everybody does that. What the heck is going on with our team?

Brent: You guys are only getting chicken sandwiches. This is ridiculous. Everybody knows it.

Brent: It’s true. So I don’t know, is there, I think it’s a hard that’s, it’s gotta be one of the hardest things as a leader to give that space to somebody to allow to to open up and tell you, cuz it is a little bit of vulnerability from that person. And and maybe that’s I’m dealing.

Brent: Three different cultures. It used to be four. We used to have an office in Bolivia. But we have three cultures now. So I think culture’s a little different, right? 

Kate: Yeah. I think, one thing is I always, and I’ve said this before, like I expect them to go to to complain about me, to each other.

Kate: I expect that happens to all managers and bosses. That’s part of the role that you’re accepting. And so good. Do it complain to each other, get it out of your system, certainly. The same way how many times you be, are you like fucking Brent? I say that of course, about myself, about, oh, whoever it is that’s just your, and it’s not you mean like you, you have to know that, like to and express a frustration.

Kate: because someone isn’t perfect in this second moment. It’s meaningless it’s just this thing, evaporating the world. And when you have people around me sometimes I’ll complain to Lauren about other people and the company and just cause I need that outlet with somebody and the validation that I’m not alone in this thought, and I’m sure they all, I know they all do this to each other, which is fine.

Kate: And I think they’re, that’s part of the culture that you wanna encourage, right? People are gonna vent it’s. This is human nature. And I think of it as if lately if everything about lately was. Just smooth sailing. Boy, we have no fun whatsoever. This is part of the adventure.

Kate: Are we gonna make it, are we not? So it, that ups and downs, it keeps it interesting. Like I, I think that’s why they come to work every day is cuz they’re wondering what’s gonna happen. I don’t know. 

Brent: That’s it’s often said that without stress, without contention, without arguments, that you don’t move anything forward.

Brent: If everyone is always on the same page you could be going in the right direction, but you may not. And having a dissenter, there is always a, it was always, it’s always a having a dissenter there to ask those questions is important. And I think that essential. Yeah, it’s essential, right? We, as a leader we need to make that space.

Brent: I know that we’ve sent people we’ve sent Indian developers to Germany in onsite to work. And one of their, one of their things that they’ve said was that they were surprised that other team members on the German team would. Hard pushback to the boss in the room. And for them, that was an eye opening thing.

Brent: Cause their culture more is more around. And I’m sure I’m gonna get a whole bunch of Indian developers not telling you. No, it’s not like that here. But their culture is more about doing what you’re told. And you don’t often. It’s not a strong cultural trait to question the boss and to say this I’m a white guy anyways.

Brent: I don’t know, concern that because that’s my perception of the culture. I’m gonna I’m making a disclaimer. I’m gonna put a little asterisks in my transcript. Don’t get back to me on this, but I digress. 

Kate: Yeah, I gotta go do shit, Brent.

Kate: I’ll say this one thing, we just released a new feature where the AI is rearranging what it finds to pull out into wholly new content. Okay. it, we just launched it like the other day. We haven’t told anybody. We haven’t even told our customers like so you’ll just start to see it suddenly the surprise you’ll be like, who wrote this?

Kate: Oh my God. The AI. and it’s pretty good. All 

Brent: right, I’m gonna go try it. 

Kate: Yeah. Keep an eye out. Yeah. 

Brent: Kate, I always give everybody a chance to do a shameless plug at the end of the podcast. So what would you like?

Kate: Oh Jesus, I’m gonna plug forgiveness today. Forgiveness. 

Brent: all right. Thank you. 

Kate: Yeah, I think we all 

Brent: need a little mark. Kate Laly Kate . 

Kate: This is why just so you know, I’m on the air. I stopped saying my name because I mispronounced my own name once in an interview with the guys from we. And so I never said it again.

Brent: Yeah. Did you wean yourself off that? 

Kate: About a thing on me. Oh my God. I love you. 

Brent: Yes, you’re so funny. Kate Bradley co founder of lately, CEO of lately. Thank you so much for being here today. 

Kate: Thank you, Brent. 


  • Brent W. Peterson

    Who is Brent Peterson? Brent is a serial entrepreneur and marketing professional with a passion for running. He co-founded Wagento and has a new adventure called ContentBasis. Brent is the host of the podcast Talk Commerce. He has run 25 marathons and one Ironman race. Brent has been married for 29 years. He was born in Montana, and attended the University of Minnesota and Birmingham University without ever getting his degree.

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