Why Most Founders Get Marketing Backwards with Amy Winner of Wheels Up Collective

kind of hate what marketing has done to social media social media has just given them a platform to become kind of like cheapened a little bit four out of five posts are brand posts now and it's so inauthentic people are just going to become very numb to add to marketing the volume of ads is going to explode if you were starting a brand from scratch if you are making a first move would it be marketing um Welcome to or welcome back to Founders in Jeans. I'm your host, Emily Jean. And before we get into the episode, I just want to say a huge thank you so much for listening to my podcast. It means the world to me. It is a really special project to me. It's very close to my heart. And yeah, before you get into the episode. And yeah, I just wanted to come on here and say thank you so much. I also wanted to say that if you enjoy the show, feel free to leave a review on Spotify or Apple, wherever you're listening to this, and also to follow us. 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I hope it's a good one and I'll chat to you soon. okay amy winner of wheels up collective welcome to the podcast how are you doing today thank you so much it's great to be here emily we are um it's bright and sunny in south carolina and glad to be here thank you i love south carolina by the way i typically go to north carolina but i've passed through south carolina quite a few times and i think it's an underrated state it's amazing it is it's like a little sleepy small town feel i love it yes exactly well For people that don't know you, why don't you introduce yourself? Sure. I am the co-founder of Wheels Up Collective, which is a boutique marketing agency that helps companies grow. We specialize in early stage tech startups, mostly, or small and medium enterprise tech companies that just need extra bandwidth. And my co-founder and I, during COVID, got the gang back together. We found our favorite people who we had ever worked with, the best marketers that we knew. and started the agency, and it's been a pretty fun ride ever since. And so I know, I have in my notes here, that you started out as a farm girl, and now you are running a marketing agency. So walk me through, what is the story arc there? Well, I mean, my family, I had a third-generation dairy farm in New Jersey, and my dad was an entrepreneur, a different kind of entrepreneur, but that grit and that work hard. a play hard mentality is sort of in our DNA, in the winners, the winner family. And so he always joked that he thought I would start a business sometime or be in charge of something at some point. And it took a little while. I worked in-house at a lot of different companies. I moved to Seattle when I was about 30 and kind of jumped headfirst into the tech startup space and just really kind of found my niche there. It moves really quickly. The problems are changing every day. It's a super interesting space to be constantly reinventing marketing and reinventing what you're working on um and it just kind of clicked and so um when i moved back to the east coast in 2018 it um just kind of fell in my lap things just kind of happened i feel like this agency was sort of like put in our lap by the universe and it's been a fun ride ever since so that's and i wanted to ask where in new jersey did you grow up i grew up in morristown Not Morristown, which is a huge city in North Jersey. Morristown is a tiny town in South Jersey. Everybody always says, oh, I know where that is. And I'm like, no, it's not the one you're thinking of. But it's right outside of Philadelphia. And when I was a kid, it was all farms. And now it's like suburbia, but suburbans for all. But it was all farms. My dad was from New Jersey. We used to go back to Ridgewood every summer. Oh, yeah. Beautiful. Yeah. Actually, next week, I'm going to the Jersey Shore. Oh, good. My grandfather had a house there and the family's always gone there. So I haven't been in two summers, but I'm pretty excited to get back to my roots and LBI. I love LBI. I think LBI is like one of the best. And when I was in elementary school, I wrote a presentation on why New Jersey is the best state or best place ever in the world. It is. It really is. That's a hard sell to a lot of people. It's going to take a little marketing. The Garden State tagline never really caught on, but it's okay. We love New Jersey. I love New Jersey. Note that neither of us live there now. We don't actually love it that much. We appreciate it. That's what it is. We appreciate it. That's totally it. Okay. Well, why don't we jump right in? I have a big question for you. Looking back, what would you say is one career decision that really changed your trajectory the most? Yeah, I think moving to Seattle was and getting into the startup scene because I had worked at smaller companies. I worked at big agencies. I cut my teeth at an agency in New York City. And then I worked at a smaller manufacturing company, actually, for eight or 10 years. But when I moved to Seattle and kind of found my spot in the startup world, I think that I just learned so much that the industry is constantly changing. Space, the B2B. um tech space in particular i think really has embraced marketing technology and marketing data and has kind of been a little bit on like the bleeding edge of that and and has been edgy with branding and has been edgy with you know taking risks and so it was a really wonderful little pond to find you know the the community of marketers is very very tightly knit in that city and um you know everybody's like maybe maybe two degrees of separation apart you know and so it's just a really good community to really develop your your career and your network um you know most of the clients that we have at wheels up are first degree contacts or people who we've worked at who at least my co-founder and i have worked with through the years and um seattle definitely did that it's a great city not as great as new jersey but it's a great city yeah seattle is a good city i feel like everybody's moving there right now too really yeah i mean it's a good place to be yeah um speaking of clients i know that you help both startups and established companies grow can you walk me through a little bit what your approach differs how it differs with different stages yeah absolutely so i think like when we're talking like really early stage you know like a pre-series a seed seed round pre-series a like that that company just needs to find something to like grab onto they need to find some kernel of success to build on, whether it's a really successful customer or a really cutting edge technology. That's where you have to really find something to hone in on and then just hustle your tush off. I think that bootstrapping. at that stage is really valuable from a learning perspective i think a lot of ceos are in a hurry to outsource marketing and it's founder ceos early founder ceos aren't in a hurry to outsource marketing because they don't know it but like if you really can hustle and meet and meet your customers where they are and learn like i think that's some of the most valuable intelligence for an early early stage company i think if you are post funding it's all about micro testing it's all about like how can you figure out what's working and iterate quickly and then throw a little money on it, you know, and see if you can grow. And then for the mature companies, it's all about how do you build sustainable programs and sustainable infrastructures that can pass from generation to generation or, you know, like team to team, because I think that those plans are much longer. You know, you're going to be planning for two years, three years, and you really need like a robust backbone in place to be able to manage that transfer. of knowledge and of power that's going to happen over those long-term planning cycles. I love that. I think that's a very simple and concise way of putting it. I really appreciate that. So if you were starting a brand today from scratch, what is the very first marketing move you'd make? And if you are making a first move, would it be marketing? I think it would really be that like getting as close to the customer as you can and really like understanding who that persona, what that persona is. And, you know, I just spoke with a founder a couple of weeks ago who is building a sales enablement AI tool. And, you know, she has tried every marketing and she's very, very early stage. She's a one shop, one shop, one person shop. And she's tried everything. She's tried cold email. She's tried digital ads. She's tried, I mean, she's tried like the standard toolkit of marketing. She's like, nothing's working. And at that point, those are all scaling tools. And I think that she needs a hustle. She needs to work her Rolodex. She needs to find people who will advocate for her. She needs to find a power user or two and leverage them. And so I think that it's kind of like I'm reusing my answer, but it's a little bit of hustle. It's really like getting in the trenches and learning how you're valuable and how you're different and then exploiting that and kind of like. grabbing onto something that works and repeat repeat repeat repeat speaking with early founders do you find that there is a common thread of mistakes that they're usually making and not even mistakes but like areas they're focusing on that you don't think are the smartest areas to focus on i think a lot of times founders they're they're in a hurry to outsource marketing and they're not ready like the the customers that we have the clients that we have that are challenging engagements is like they don't know who they are They don't know what they're doing. They change the change directions, which you have to do in the beginning. Right. But like wait until you really got it solidified a little bit before you start to pull marketing into it, because, you know, we just spent a lot of time chasing our tail. And so really making sure that before you spend the money and the time, it's not it's not just the money that you're going to put into it. It's the emotional and mental bandwidth that you're going to put into it that you need to make sure that you. you're pretty you're pretty confident in what it is that you're selling and who you're selling to before you start trying to scale it through marketing you know i think about the first um the stereotypical first and second sales people that an early stage startup will hire like they are cowboys it is like wild west they are selling anything to anybody right like they are shooting first and aiming second and you kind of need to do that to find toehold somewhere and really be able to start to build something repeatable from there. And I think that founders will get a glimmer of something and then just want to go to 100 miles an hour. And you just have to really be sure, I think, before you try and do that. It's tough, though, because you're often trying to raise money. You're trying to keep people employed. You're trying not to run out of money. Everybody knows the runway. That is like in the back of everybody's head or the front of everybody's head. It's tough. It's a tough and it's definitely a boiler room environment. For sure. Yeah. Especially, I think everybody is overworked. Nobody has any time. It's a difficult thing. I think that's true for most organizations these days. Yeah. Is there a growth tactic that you love that you think is underutilized? I think one of the things that nobody likes to hear from us, but it's hard we joke it's like dragging people through the glass you know you got to get in the data and you have to really understand it and you have to do postmorts after everything you know like really it's so easy especially when you're at in an early stage to kind of like do something 98 of the way and then like you're on to the next thing instead of finishing it stopping looking at what worked actually learning from it and then iterating everybody kind of feels like they have a gun to their head to move on to the next thing and right there's so much value in in learning what what worked and what didn't and building on that instead of just doing things and so i think that's something like we try pretty hard a lot of our clients are in a hurry to automate everything they want to automate as much as possible i think that like that's tough because you're going to waste a lot of you're going to spend a lot of time and money building the automation and you might be automating the wrong thing so like It's not fun to get in and dig through like your CRM and really understand what the data is showing. But I think it's like time really, really spent well. Yeah, I guess then on kind of the flip side, is there a marketing trends that you have been seeing that you wish would go away, disappear? Am I allowed to say social media? I know that's like a controversial slash. unpopular answer but for like personal societal reasons i kind of hate what marketing has done to social media you know like it was supposed to be where like you connected with your your college friends to like see their kids you know and and it really four out of five posts are brand posts now and it's so like inauthentic and plasticky and i think that it's also like spawned this community of influencers that have really like cheapened that role like the role of like an advocate or an influencer used to be really meaningful it used to be like those champions you know and i think that social media has just given them a platform to i don't know like become kind of like cheapened a little bit and i think that it's a shame that marketing has i mean i understand why brands do it all right so a lot of our brands do it but i don't know that social media is great for society yeah at large Well, I think most people can agree with that. I'm curious to hear from your perspective. Do you still think it is an effective form of marketing? Absolutely. Absolutely. I mean, especially, I mean, the targeting is so good. And I do think there are some really good social campaigns out there. I think that there are brands that are doing it in a really authentic way and connecting with their customers. I just think that most brands aren't, especially most B2B brands. Like, you know, you think about like the, especially like the D2C, the direct-to-consumer, you know, retail brands that have popped up, like they only survive because of Instagram. Like, and they're these small, you know, like one-person companies that are, they're making something super creative, like a wallet or, you know, and what an amazing platform to be able to grow a business like that. But I think. almost most of the large b2b marketing and the corporate you know the enterprise marketing that's on there is like pretty much a snooze fest right yeah i completely agree with that especially when i get on linkedin i'm always like amazed at the hard hard selling constantly constantly hard selling and it's like not even creative or smart it's it's you know and i mean i have to like like i'm gonna out myself here like I have automations running in LinkedIn. I have the automated outreach connections, book a meeting. It surprises me how frequently it works. People are like, oh, thank you so much for connecting. I can't believe you found me. I'm like, yes, I did. I don't know. I guess it still works. It makes me super sad that AI, which is this amazing technology, is being used to automate. spam commenting on LinkedIn posts. Like, can't we use it to cure cancer? Come on, do not drag us down into using AI for bad LinkedIn comments. It does make me really wonder how the general public is going to use AI in the coming years. I'm so curious. I do think actually there will be a time where everything will be AI and then we'll transition slowly back into more human-centered approaches, but I think it'll be a long period before we see that come back around. Yeah. You know, I kind of like vacillate back and forth between being like terrified about it and thinking that it's going to like, the adoption is going to be so rapid. And then thinking about the vast majority of the population that is so slow to adopt changes. So I don't know. I think the new like AI previews and search, the AEO previews and search that Google has. it'll be interesting to see how quickly that you know how how quickly that displaces the regular search rankings like the organic search rankings because most people don't realize that that is different you know that they're getting served information in a different way um but also uh you know that google how's google gonna make money so it'll just be really interesting to see how it how that whole um This week's episode is sponsored by Kaya. Kaya is democratizing women's access to funding while treating the multi-trillion dollar female economy for funding female genius. If you've ever wished you could be part of the excitement of funding and supporting the gorgeous growing businesses you love without being an accredited investor, this is your moment. Kaya is building something entirely new, an ecosystem women can fund founders they believe in. access curated experiences, and learn how to move like investors together. They're now onboarding for the next round of beta and collecting insights from as many women as possible to shape a platform women will be obsessed with. To get involved or join the waitlist, head to kayawomen.net or send Kaya's founder, Haley Handler, a cheeky DM on LinkedIn and step into the future of funding women. I just want to thank Kaya so much for sponsoring this episode. I'm so, so, so grateful to have them as our very first sponsor. They are very much a brand that is aligned with the podcast. And now, back to the episode. For sure. Yeah, either sink or swim, I guess, is like the biggest thing. Yeah. Yeah. Even that new iteration of GPT with the agentic, you know, it can like book a flight for you essentially, and everyone has access to it now. this is, this is the, probably the, that's like been the first time other than the first coming of TouchBT. I'm like, okay, okay, okay. Like things are speeding up. Yeah, yeah, yeah. So I guess there's this thing called the PDOOM, the probability of doom. What probability, what probability do you believe that AI is going to like take over the world Terminator style? And so, you know, when, when they, people in the industry, that's like a number that they use. And like, sometimes my PDOOM is like two, I think there's a 2% chance that, you know, the bots will take over but then other days i'm like oh it's a hundred like it's definitely like the world is going to end because yeah yeah yeah yeah it's tomorrow yes yeah i don't know if i'll be here for it but it's definitely going to end because of because of ai for sure yeah yeah it's um i i saw the other day i was listening to podcasts they were talking about the different types of categories you can fall into in your kind of beliefs surrounding ai and like you're either an ai inevitabilist so like you know it's inevitable and you either have a positive or negative opinion on that or you think it's a trend and yada yada yada i thought that was really interesting they were talking about how it goes back to like caveman days and like people who accept the other and they're like this is inevitable or like no no no we need to protect ourselves yeah right that's how i felt it is inevitable right like there's no avoiding it yeah i i know I'm finishing up my master's right now in my last year of my master's degree. And I had two professors last year who said no AI use whatsoever. And then two professors who said, use AI ethically and kind of had some rules and regulations around that. And then this semester I have the same professor and now he's slowly implementing AI into his course. But every single time he talks about AI, he has probably eight paragraphs before about, how unethical it is and the environmental concerns and then like all of that is so valid but it's like this I hate to see it that's not going to change anyone's if they want to use it it's not going to change anyone's opinion it's inevitable yeah no I think I think you're probably right it has been interesting to see like how schools have adapted to it like even I have nephews who are a freshman and sophomore in high school this year and like they use it we have an intern at we have an intern at wheels up who actually builds all of our custom we do custom gpts for each of our clients and he builds all of them he was great this summer until he had to go back to 10th grade last week and now and i was talking to at least like a week ago and she was like i was asking him for advice like i was actually asking his opinion on things you know and he's 15 so right it's uh yeah it's here it's here to stay yeah I do think it's a great opportunity for people like the bar for knowledge is still fairly low to be knowledgeable in it. Even my friend and I were laughing because the university I'm at got voted for having being the number one university in Australia to be implementing AI in their courses. And it made me laugh because I mean, sure, they're using it a little bit, but like The bar is very, very, very low, very low. I would have assumed it would have been like a technology university or something like that. But no, apparently it's us. And that's just because we are allowed to use Claude. Well, I mean, it's interesting to think about how it's going to like upend the marketing industry for sure. You know, I think that agencies are going to look totally different in three to five years, you know, and, you know, we're thinking a lot about that. Like, how do I? How do I stay ahead of that? How do I stay relevant? How do I help clients navigate? Because every one of our clients is asking us, they're coming to us with, you know, the AI tool du jour that they got a cold email about and saying, should we do this? Should we implement this? Is this, you know, can you do this? Can you spin this up for us? And, you know, I think that I hope there's going to be a space, especially in like the. the pond that we're in with smaller companies or you know they don't have a huge they're not gonna they're not gonna hire a prompt engineer they're not gonna hire an ai engineer to to set up all of their um ai tools for the whole for for marketing and other other departments but i hope there's still a place for marketing strategy to like drive the use of ai at least in like the medium term at least until i want to retire and then it can take over the world yeah yeah no worries No worries. You'll be on a beach somewhere. It's not your problem. That's my plan. What is your opinion then? I want to ask really quickly. Did you hear about, I think it was Mark Zuckerberg, somebody said, they want all of all meta ads by next year to be completely AI run. So basically there's no human hand in it other than saying, this is what we need. This is who we're targeting. What's your opinion on that? I mean... I think it's going to, I think it's going to speed. I think it's, well, I think it's going to get better, but it's not going to be more effective. I think like the targeting is going to get better because really like they're just AB testing faster, right? Like AI can just AB test faster and hone it faster. But you know, the thing that like keeps me awake at night with AI is that there's, the volume is going to explode. The volume of ads is going to explode. The volume of emails is going to explode. And people are already so um glazed over by it you know i don't know how many cold emails you get you every day but i get dozens and dozens and it's going to explode it's going to get to the point where i get hundreds of them every day and right and i think that people are just going to become very numb to marketing when there's like an over proliferation of it do you think there will be any platforms i guess that are any forms of advertising that will then gain a greater foothold given that these ones will be kind of overused. Well, it's funny because I'm on this big like Reddit kick lately for ads. And I think and I was thinking about it, you know, like outperforms every other one of our platforms for our clients and people that read it like that's, you know, like super, super, super niche and it's super. you know opinionated and but that's why it's authentic that's why people trust what's on there and i don't think it's inundated with ads i don't think it's inundated with brand messages the ads aren't quite as um marketing-y there or people don't perceive them that way. So they're effective. And especially with the micro-targeting that you can do in all the subreddits, I think that it kind of goes back to how marketing should be, where it's very personal and it's very relevant and it's very timely. And I think that that's probably the only platform right now that is able to deliver that because it's still content. It's still 100% user-generated content that's valuable. Now maybe the AI. troll bots will come in and it won't be but for now i think that's why it's effective for clients plus it's like so cheap so you know you can run a lot of ads and and still have a pretty good um conversion rate interesting i knew that you could run ads through reddit but i haven't really heard that much about it i guess it's not that surprising given it's very community oriented So these are all paid ads you're running through at it, right? They're like little display ads. Yeah. Yeah. And we found, we have found that like can't jump straight to, you have to market the funnel there. You can't jump straight to like double this white paper because that's like very jarring in a Reddit forum. It has to be a lot of like awareness. It has to be a lot of like knowledge. Here's a, here's a blog post. Here's a, you know, you have to give information that's relevant to the topic and people click on it. People click on it and they read it and you need to. You need to hit them with that three or four or five times before then you start to serve landing pages to them with actual forms where they're asking them to give you their contact information. Interesting. Good to know. I knew that there was a lot of people playing the organic advertising through Reddit game lately, which I think is very interesting, building out these kind of... you know they look like real reddit profiles and then it's basically they're just promoting xyz products yeah because that's what i do like about reddit it's so transparent like you can go to their profile immediately see that they've left 20 comments saying the same thing on a bunch of different reddits but also like the flip side of that is like i think if you do that in a very genuine way like a lot of times it works you know if you're like i am so and so from this company and here's our opinion on this like people respond well to that you know especially if it's not only sunshine and rainbows you know if it's like that you know here's the good and the bad i think people really really respond to that so it goes back to like authenticity and that personal connection building that personal connection with your audience yeah absolutely It takes time though, right? That's kind of like that bootstrapping that I was talking about and the hustle that, you know, you got to get in the trenches and spend the time doing that, I think, to really understand the problem that you're solving. It's a lot of things with AI. I feel empathy slash community-centered approaches are not going to go out of a style. Like people talking about, I'm going to lose my job. But there are certain jobs where if empathy is at the heart of it or community, for example, teaching, nursing, that would be really, really difficult to have a bot replaced. Yeah, I hope. I don't know. I always go back to like the old like sales adage that like people buy from people who they like. They do, you know, like you will buy an inferior product because you love the salesperson right now. So I think that. Right. I don't think that will go out of style. Yeah. Soon. although i do love my chat gpt like a real person i think yeah yeah i'm like really fond of her you know it's so funny there's like all the memes like going around the internet that are like if i'm in the hospital you know like please go delete my chat gpt history like if i'm in a coma like if i die go delete it because i don't want anybody to see what i know i i also am very i'm very picky and then now it's i've learned it's a bad thing they should stop doing it but i always say please and thank you to my chat bt i do too because when those robots take over like i want that to be the polite one that they remember remember i was nice i was nice and my boyfriend hasn't i saw the other day that he doesn't he like bosses chat bt around i'm like it actually feels a bit sexist to me you're saying to robot do this do this write it like this that's not good but wait you're so rude you really need to start saying please and thank you. It's a perfect kind of practice. Although I did find out that it costs a bunch of extra energy and water and all that stuff. Priorities, manners, environment. I'm not ready to give up my humanity and saying thank you and please. I'm just not. Exactly. I can't. It's ingrained now. Okay, let me get refocused here. So you have focused on aptitude and potential over years of experience what made you throw essentially the traditional hiring book playbook out of the window well i i so there's one that's a really good question so there's one year i was at a startup we hire i we hired 100 people in a year and which you know we i think we had 30 when we started we went from 30 to 130 and so it was like all hands on deck with hiring and i think um that year i counted at the end of the year and i had been part of over 100 interview loops and we had like a pretty intense interviewing process where you know there were five people on each loop and there were they had to be in different departments and you had a debrief and you had a pre-brief and you had to like write out your notes i mean it was and i think that um like hiring is a skill that you have to hone some of it comes down to a little bit of like reading people well and gut intuition on people and like learning to be able to spot the talent because like skill doesn't make a team click skill doesn't that's not what success is about especially in a market i think in a marketing organization like it's about like how the team gels together especially in startups where it's like a constant hustle like you need people who care about each other and who care about the product and who care about what you're trying to do and are willing to like stay late for each other or pick up the ball and somebody's out sick or and i think that like finding people who are compassionate and a good culture fit like the same the same they're made with the same you know dna i think that becomes the force multiplier not necessarily like i have these skills you know here's my checklist plus also like a lot of people can bs their way through an interview pretty well so you know i we all know somebody who's been hired because they had a stellar resume and their pedigree was you know not false it wasn't false divided in any way just they they weren't a good you know they weren't going to fit amazing pedigree not a good fit so i think that really like especially in those small teams that move so quickly and and uh the resources are tight time is tight money is tight headcount is tight like you've got to get along with each other and you've got to care about each other so i don't know plus like you spend so much of your time at work like you might as well create a team that people like coming to work right and they like the people who they work for you know we i worked for that company that we grew really fast the ceo you know did and just an amazing job curating people who had the same um socially minded you know dna it was the same that we had the same philosophies on like it's so appreciate but like we're changing the world you know like every every startup ceo is like we're gonna change the world but we really actually thought that we were you know and so um that is you you can't teach that you can't teach that in an mba program you can't teach that you know in college you can really like you either have it or you don't right and so is your team now is it most is it hybrid remote everything in person what's your setup We're distributed by design. We will always be remote. We started in the early, early days of the pandemic. My co-founder and I had kind of like been through the ringer at larger companies, you know, where they're, it just was not like, they were not treating people the way that like we wanted to be treated. And we were like, why are we doing this? Like, this is, this is dumb. Like you spend too much real life at work. It's not worth like the huge paycheck that we were both getting. And so, you know, we started during the pandemic and she was actually, she and her husband, took the year to travel around the country in like a travel trailer and you know or in a camper and um it just that's the kind of life we want to have that's the kind of life we want to have for the people who work for us there are amazing people who are fantastic at their jobs who don't want to sit at a desk from nine to five so build a digital infrastructure so that they can work anytime anywhere they can communicate seamlessly you know a crew, a team of people who, you know, are good together. You know, they're better together that trust each other. And I think that, that, um, I don't know. I don't, I don't miss any. in-person meetings. I don't miss that. I don't think we're missing any magic because we're not in the office bumping into each other at the water cooler. A lot of companies are rushing back to work now or pushing back to the office now. They say, oh, so much magic happens in the kitchen. I don't know. We hop on Slack. We have enough silly threads in Slack that are provoking fun interactions. I don't know. I don't miss it at all. But most of us have worked together before, too. So I think that that really helps. I think that that helps. Changes, yeah. The culture, yeah. Yeah. Yeah, I agree. I've had positions where I've worked fully remotely and also where I've worked in a hybrid model and then also was completely in office. And I do think the obsession now with people going back to in office, I don't know if it's like people are romanticizing it, but I was like... I think one, I am frankly way less productive in the office. And I know not everybody is the same way. But for me, it's like I would then I'm like chatting to my coworkers for most of the day. And I'm like, it just doesn't work as well for me. But everybody's different. I think it works. Most companies, you know, if you think about, you know, the pool of employees. most companies have a couple high performers, a couple middle of the pack people, and then a couple, you know, hopefully them, you know, at least, you know, the majority of them are middle of the pack and then a couple like low performers. And I think that like leadership is obsessed with like the low performers, you know, and if they're in the office every day, they will do more work, you know, and maybe they will, maybe those people will, maybe the middle of the pack people will, but like. Raise your hiring bar. Do a better job hiring people. Do a better job finding people who are already inspired and their job is such a good fit that they want to do it. And then let them set up whatever environment lets them be the most successful. I really believe that you do better work when your life is happy, when you can have kids or a hobby or travel or whatever it is that makes you excited about getting up in the morning. Don't force that. out of the day you know like don't force that to just the weekends let people have that be the majority of their life that that work kind of fits around right right and i i my biggest complaint too about in office work is this eight hours is like a very arbitrary number in my mind is like sometimes the job takes longer sometimes it takes shorter usually it's shorter but if you're in the office from nine to five then you are going to make it take eight hours yeah like no matter what what it is anyways yeah that that it's like that it just i've always felt like they somebody picked that number out of the air and then everyone was like all right and that makes sense now that's it that's how long every single job in the world will take from monday to friday yeah well it's funny because i taught you know people people who are kind of outside of like my world are like, oh, the tech startups, they've got these, you know, remember when, when they, when Google started rolling out, you know, and Facebook, these, these like perks, these crazy perks, like chefs, and you know, like, they'll take your dry cleaning. Okay, first of all, no engineer has dry cleaning. So that perk is like irrelevant. You know, we're like, you can bring your dog to work or whatever. They do that because they don't want you to leave. They want you to keep you there. They do that because they make it easy for you to never leave so that you can work. 10 12 15 hours a day and not even notice it's like when you go into casino and there's like no clocks and no windows it's kind of the same in startups and um i mean you can do it for a little while people can do it for a little while and you can dangle you know the carrot of stock options in front of them but especially as it gets harder and harder to actually have a successful exit as as an employee and make money in a startup like i don't know yeah i don't know how long that lasts Yeah, I completely agree. I have also fallen for this free snacks and the, I'm trying to think, like, you know, in-office gym, all those things. And I still, I won't lie, like now that I work remotely for myself, basically, and I'll hear my friends and they're like, oh, I just went to the pool in my office building. I'm like, oh, that sounds so much fun. But also it's sneaky and it's tricky and I don't like it. Well, who wants to go, like, be in a bathing suit around your coworkers, first of all? Yeah, no. No one. Like, awkward. Awkward. We don't need to get changed in the changing room together. We just don't. Exactly. So I'm curious, have you ever taken a big hiring risk that paid off in a big way? Well, my two, two of my favorite hires of all time, I always talk about these two people because, like, okay, one, I hired a woman to be a... uh a customer marketer who was a nanny she was a nanny of someone who i knew she had just graduated from college with like a business administration degree and she came in as an intern and i mean she didn't she didn't know anything about marketing but i had seen her like run this household like a you know tight ship i was like okay that family is pretty chaotic and i you know those kids are incredibly polite you know she's those kids are always on time like it's hard to um wrangle toddlers and she did an exceptional job of that so i was like we can teach her how to be a marketer and to this day she still works with me you know i think she started recommending she was like 21 or 22 and that was at least 10 10 12 years ago yeah 15 years ago maybe And then the other hire, I hired using community health development. He worked for hospitals in community outreach. And I hired him to be an events manager. And he had never been to a trade show. He'd never been to an event, like a marketing event. But gosh, he just had that warm personality that was instantly likable. Instantly likable. And I was like, you're going to be able to sweet talk people in a booth. You are going to be able to like get to the front of the line of Freeman. And when you don't have your bill of lading, like, and you don't have the right paperwork to your booth picked out, like, you know, like he, he could just sweet talk his way out of anything. Not in like a slimy way. Just, he was just kind and like genuine and sincere. And he's a heck of a marketer. He's, he still works with us too, actually. So they're like two of my favorite people, my dearest friends too. Like they're just really. good people but didn't know a whole lot about marketing when i hired them and people were like are you sure are you sure you want to hire these you know and like the cmo in both of those cases was like okay i don't know how i'm going to sell this to the ceo of the company like they don't have any marketing background you know i'm like i'm willing to like go out on a ledge for them you know i think these are good hires and yeah and they were but but also like you know one of my things is like that only works if you're going to manage you're going to mentor them and manage them and you know i think a lot of times like you know, people want to climb the ladder and they want to be a manager. They want to be a director. They want to be a VP. And like, they forget, like, there's so much responsibility that comes with that, right? Like, you're not just getting a bigger paycheck. You are, you are developing your team. You're in charge of developing your team. And I think that like managers need to manage. Managers need to spend the majority of their time developing talent, not just hiring people and then delegating. Figure it out. Totally. Yeah. Yeah. Completely agree. Well, I want to know, do you have one piece of advice for leaders who want to build teams that actually last? Do not lower the bar because you get into like, yes, do not lower the bar because, you know, it's hard to hire people. It takes a long time. It takes, you know, your attention away from running the business. And I think it's so easy to. you know, just hire somebody who's good enough, you know, and you're like, I think they'll be okay. Like, don't do it. Or this person's cheaper. Don't do it. Like your talent is the most important thing in the company. Like do not lower the bar. And, you know, we used to have like this, like saying at one of the companies that I was at was like, is this person a bar raiser? Is this person better than average in the company? And if they aren't, do not hire them. Do not hire anybody that's below average, you know, because you're just going to drive, you're just diluting the team. I like that. I've never heard that before, but that's very direct and to the point. I think that's a great piece of advice. Thanks. So I have questions. Sorry, I'm looking here to see where I'm going next. Okay, speaking of AI and how the future is a bit uncertain, how do you keep teams motivated when the future feels uncertain? I think you focus on... what you do know and what you do well. Maybe our team is different because we have worked together for a long time and we are really tight, but I'm very transparent with the team. We are all talking about how a lot of people on our team's jobs are going to radically change, especially when you think about copywriters and designers. Those are in the firing line. And so we talk a lot about how do we develop those people into into different roles so that they don't just become obsolete they can grow into a sustainable career in this like new era of ai marketing i think that especially when when things are changing and the ground kind of moving under your feet like people want to feel secure people want to feel safe especially with a paycheck like that's terrifying right like so i think that you know again having a dose of humanity is It's good for everybody. It's, you know, you get a better handle on what they're thinking. You get a better handle. There are less surprises all around. So I think like kind of, you know, circling the wagons and staying close with people and then managing your team, you know, a little bit with some compassion and empathy, I think is, it's going to get, it'll get you through it. I mean, we had two years, two years ago, 2022. I think it was 2022. It was a rough year for us. We had the whole tech recession, remember? Every day, the New York Times had another article about Facebook lays off 8,000 people. Salesforce lays off 10,000 people. And luckily, it didn't percolate down into the larger economy. It was mostly limited to tech companies. But we lost half of our business in a couple months. And we're not huge. So that's kind of hard to swallow. you know we batten down the hatches and we pulled our core team members in close and we all kind of talked about okay this is where we're gonna cut this is how we're gonna stay afloat this is how we're gonna make sure we don't lose the customers that we do have and we got through it we didn't have to lay anybody off you know people took some pay cuts or some reduction in hours but we got through it and then those people were i think even more loyal to us at the back end of it so that now when things are good and we're really busy and we really need to hire more people like they're willing to you know help pick up the slack and you know right yeah i think um a lot of people or at least i've seen organizations companies when times are tough they suddenly cut off all communication i think that's the worst thing you can do blow out yeah and like i think honesty is the absolute most important thing at that time I think that I'm going to go a step further and say it is cruel to do that. It is not ethical to do that. People are worried. It's their income. How are they going to pay their mortgages? How are they going to put food on the table for their kids? I think that leadership has a responsibility to take care of the people who work for them. I can tell you, everybody already knows there's a crisis. If something's bad, they already know. By cutting off communication, you're not keeping it from them. They already know. And if they don't know what's happening, they're going to fill in the blanks on their own. And that never ends well. Right. Yeah. Amy, I don't want to take up too much more of your time. So I want to ask you some rapid fires and then we'll wrap up. But okay, I have some good ones for you. very long-winded so we'll see how this goes okay no worries you can be as long-winded as you want i find that rapid fire is more like not not rapid fire fire um okay i kind of already asked you that is there one marketing buzzword that you're tired of hearing i'll give you three okay love so and these are all like start a few ones but like okay i hate i hate that we're building the plane while we're flying it you know like they like that gets said 10 000 times a day every time somebody says that like an angel investor loses his wings like it really like stop saying that please okay but i also like i think i hate it because it like resonates in my soul like i can visually picture you know like like a wheel falling off as you're flying at 30 000 feet yeah um the the one that i think has gained traction lately these aren't marketing terms but they're just like things that drive me crazy it's like um the juice isn't worth the squeeze like oh like that just i don't know i don't like the mental picture that that evokes like i don't like that for sure it's creepy right it is creepy people say it all the time now and then the other one is like people say this like i don't know if you've heard this like thing one is this and thing two is that and then they like refer to them as like thing one and thing two and you're like just say the things like don't label them as thing one and thing two like dr seuss yeah Exactly. That's interesting. I've not heard that last one or the second one, but I believe you. Now you probably will. You're in Australia. It hasn't caught up yet. Come back to the States and this is all you're going to hear. It'll be like, the kangaroo is not worth the squeeze. And I'll be like, heard that one. Overdone. Yeah. Oh my gosh, that's funny. Best piece of business advice you've ever received. oh gosh well i don't know if it's the best but it sticks with me so i had my very very very first svp was a woman named debbie roush i worked at a big ad agency called apl and she i remember i was on the johnson and johnson account and i was going to my first client presentation my first client meeting you know and i had to put together these binders this is how long ago i had to put together like binders of this presentation we're going to go through and This is so silly as I'm telling this, but like there are all these like you had to put like dividers in it. Like remember the old school dividers before you had Google Docs with like it's built in, you know, table of contents and tabs like when we use paper. And in the supply closet, there were like all these packages of like the dividers and you know, like the little like tabs like line up along the top. Like, well, there were all these like half packages of dividers. And so. i like cobbled together a bunch of different like half packages because i was like trying to save money and like trying to be you know like thrifty and she the next morning because they're super late that night like doing it and we go to the home in the morning to get ready for it and she like ripped into me and was like this looks like a kindergarten like science project this is like this is a you know hundreds of millions of dollar client like you cannot do this and i was just like like you kind of have to i don't i think like that polish that level of like taking everything very seriously when you're client facing and it extends to customers too when you're customer facing like i think that that that level of detail being very detail oriented i think i think it's important because it does reflect poorly on you when things aren't very very buttoned up yes yeah so i like that that's not a typical piece of advice that i would hear either but i can totally see how that's true It's simple, right? But it's so easy to glaze over. What is one skill every marketer should master? You got to sell. You got to be able to sell. You have to be able to sell yourself. You have to be able to sell your plans. You have to be able to sell to the CEO. You have to be able to sell to the board. You have to be able to sell to your sales team. You have to be able to get in front of a group and understand what motivates them and change, be a little bit of a chameleon because pitching to your CEO is a lot different than going to a QBR. you know our sales kick off and like getting this out the sellers excited about whatever marketing you're doing because they don't care but you know i think that you have to be able to sell you can't be somebody who sits in the corner and sends emails right you got to be dynamic and get up and charismatic and you got to sell yeah i love that true which is funny because i went into marketing because i hate selling so like i would be a terrible salesperson but I think that marketing is a, it's a work around selling in a way. Like it's like you're selling, but you are doing it in the softest way possible, I guess. Yeah. Yeah, totally. Okay. My last question is, do you have a book or a course or resource or anything along those lines for people who want to make their own startup or budding founders slash entrepreneurs? I think a lot of the like. For budding entrepreneurs, I think a lot of the tech incubators have pretty good content that they put out. Their blogs are pretty good. I am an avid podcast listener, and I think that understanding culture and where it's going is really important for an entrepreneur, even if you're not a technology company. So I think mixing up your podcast. rotation is pretty good my favorite tech podcast i plug them all the time is like the hard fork podcast from the new york times okay it's all about ai and the culture of ai and how it fits into society and it's a it's a little bit of like tech bros gossiping too but it is definitely it's once once a week on fridays it's usually about an hour and they're funny first of all but um it has really done like a great job of helping me understand like the landscape of ai and how it's evolving so whatever your industry is like find those little specialized podcasts that are out there for sure i don't know i hate to read am i allowed to say that like i hate social media and i hate to read no i had i had a founder said this exact same thing on the podcast yesterday oops i don't know i read all day like i don't want to go like read a book or like read an article i just i don't yeah so yeah i should right now in my life i don't yeah everybody has their own different you know formats and things that work for them yeah i love podcasts i have to listen to them on 2x though like i you know regular speed is like way too fast i'm like 1.5 that's like that's it pretty good yeah yeah 2x is really fast it is really fast i feel like it's like sudoku for your brain though you know like all these all these people say you know like you have to do puzzles to keep your brain sharp i think listening to podcasts on 2x like it keeps your brain sharp yeah i heard somebody the other day said that they listen to youtube videos on 4x i was like i don't think you're actually picking anything up yeah i think you are just hearing gibberish or you're like way smarter than me like yeah right you're actually ai this is what you are well amy thank you so much for joining me where can people find you where can they find wheels up collective all those things yeah we are at wheelsupcollective.com and we're on all the social channels obviously um my email is amy at wheels up collective.com and i i always like so my my favorite thing about my job is when i get to talk to founders and and entrepreneurs and and people who are like building it so i try and leave space in my calendar every week for those kind of like come pick my brain calls and like they're not sales calls and they're not attached to business my business they're just i just like to talk to founders and and kind of i don't know be a sounding board or maybe have an idea or two and so i invite anybody who is uh trying to build something and and wants to pick pick a marketer's brain to like i have time on my calendar the link is on the website you know i would love to i love to check i love that kind of stuff and i think i really think you know like you have to like use your powers for good and i feel like that's like a tiny way to use your powers for good yeah absolutely what a great resource i think that's i think that should be everyone's go-to resource for this episode that's perfect we also have tons of ebooks on the website they're all free and so you know we try and it's funny because people always say like why why do you give away like we give away our plans we give away all of our templates like every one of our templates that we use you can download on the website and because i think that a lot of companies like should do it themselves and also you know it's just like they're the the you know public trainer or the private trainer industry is very robust in the gym you know in the personal personal fitness world because people want somebody to like hold their hands so i think that like we will always have a place to hold hold our clients hands but for people who want to do it themselves like go download it from our website yeah yeah i love that that's great what a good attitude to have okay well thank you so much for joining me this was a great episode i'm so glad i got to chat to you yeah thank you so much for having me of course no problem And that is a wrap.

Why Most Founders Get Marketing Backwards with Amy Winner of Wheels Up Collective
Episode Description
From a New Jersey dairy farm to co-founding a boutique marketing agency trusted by early stage tech founders, Amy Winner has built her career on grit, intuition, and an uncanny ability to spot potential where others don’t. In this conversation, Amy breaks down the real state of marketing today, why early founders consistently focus on the wrong things, and how AI will change (and already is changing) the entire industry. This episode is a rare blend of honesty, strategic depth, and founder-to-founder truth-telling you won’t hear anywhere else.

This episode is a reminder that the future of marketing isn’t about chasing every new tool but anchoring yourself in what is deeply human: connection, curiosity, and conviction. Whether you’re raising a seed round, building your first marketing function, or trying to stay relevant in an AI-powered world, Amy brings clarity you can act on today.

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