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.

Highlights

  • Why founders should stop outsourcing marketing too early

  • The one career decision that changed Amy’s entire trajectory

  • The real reason most startup marketing fails (and how to fix it)

  • Why AI will make marketing louder - but not better

  • What it actually takes to build a team that lasts

  • Reddit ads: the most underutilized growth channel today

  • How to micro-test your way to product-market clarity

  • Why hiring on pedigree is overrated and hiring on potential wins

  • The “drag people through the glass” part of marketing that no one wants to do

  • The future of creative roles in an AI-driven marketing world

  • The leadership mistake Amy believes is deeply unethical

  • The one thing early founders should obsess over (hint: it’s not automation)

Time-Stamped Guide

00:00 - Emily opens with thoughts on the state of social media
02:07 - Meet Amy Winner of Wheels Up Collective
03:07 - From dairy farm to tech marketing
05:53 - The career move that changed everything
07:16 - How marketing strategy differs across company stages
09:16 - Amy’s first move if she started a brand today
10:37 - The biggest mistakes early founders make
12:25 - A growth tactic most startups overlook
13:55 - The marketing trend Amy wishes would disappear
15:04 - Does social media still work?
16:36 - AI, spam, and the future of marketing noise
17:44 - How AI previews will reshape search
19:41 - The probability of AI doom (Amy’s take)
22:36 - How AI will upend marketing agencies
23:53 - Ads fully run by AI - smart or scary?
25:19 - Why Reddit ads outperform for early brands
28:52 - Why empathy and community still win
30:47 - Throwing out the traditional hiring playbook
39:29 - The biggest hiring bets that paid off
42:18 - How to build teams that actually last
43:32 - Leading through uncertainty
47:14 - Marketing buzzwords Amy never wants to hear again
50:43 - The one skill every marketer must master
51:39 - Amy’s favorite resources for founders
54:04 - Where to find Amy and Wheels Up Collective

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.


⭐⭐⭐⭐⭐
If you loved today’s conversation, please rate, review, and subscribe to Founders in Jeans - the podcast celebrating women claiming their worth in business, leadership, and life.

💌 Build the life you deserve - on your own terms. Subscribe to the Founders in Jeans newsletter, the no-BS guide to startup life, consumer brands, and becoming your most confident, successful self, written by Emily Jean. Join 50,000+ women redefining wealth, community, and growth: https://foundersinjeans.beehiiv.com/subscribe

Follow Emily:
https://www.instagram.com/emily.jeans/
https://www.linkedin.com/in/emily-jeans/

Follow Founders in Jeans:
https://www.instagram.com/foundersinjeans/

Follow Amy Winner & Wheels Up Collective:
Website: wheelsupcollective.com
Instagram: wheelsupcollective
Email: amy@wheelsupcollective.com

SEO Keywords 

female founders, startup marketing, early stage marketing, B2B marketing, marketing strategy, Amy Winner, Wheels Up Collective, Emily Jean podcast, Founders in Jeans, tech startups, seed stage growth, Series A marketing, founder mistakes, how to market a startup, marketing for founders, growth strategy, go to market, GTM strategy, bootstrapping marketing, customer persona building, founder-led sales, marketing data, marketing analytics, micro testing, marketing iteration, AI marketing, future of marketing, AI tools, AI automation, search AI previews, Google AI search, social media marketing, social fatigue, influencer fatigue, digital ads, Reddit ads, startup hiring, hiring for potential, culture-first hiring, distributed teams, remote teams, managing remote teams, startup leadership, founder advice, startup recession, marketing downturn, building resilient teams, authenticity in marketing, sales enablement, startup branding, marketing mistakes, marketing trends, founder resilience, startup community, startup empathy, customer discovery, product market fit, early adopters, startup storytelling, brand building, B2B growth, content marketing, CRM data, marketing funnel, awareness strategy, retention strategy, early founder advice, female entrepreneurship, hustle culture, work life balance, startup culture, remote work, startup HR, startup team building, startup layoffs, founder transparency, startup uncertainty, startup fundraising, marketing channels, Reddit marketing, niche marketing, community building, empathy driven marketing, AI doom, AI ethics, tech culture, podcast for entrepreneurs, business insights, startup journeys, women in business, founder challenges, startup experiences, leadership EQ, startup hiring mistakes, nurturing talent, creative careers in AI era, future of work, startup authenticity, marketing playbook.


Transcript: 

Emily Jean (00:00)

I 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 gonna become very numb to marketing. The volume of ads is gonna explode. If you were starting a brand from scratch, if you are making a first move, what would it marketing?


Emily Jean (00:23)

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. You can follow us on Spotify, of course. You can follow us on Instagram at FoundersinJeans You can also find me on Instagram at Emily.Jeans.


or you can look me up on LinkedIn. I'm always happy to connect with people on there and I have a lot of good conversations from listeners. Also, you can always leave a bad review for us. I'm totally fine with that. And in fact, I think that's exciting. I would love to know what we can do to improve. So you can also leave comments below and let me know what you enjoyed, what you didn't enjoy. I actually do read every single one.


We also have a newsletter that comes out once a week so you can get all the updates from us. also put in


some weekly business and marketing updates in there, as well as some personal notes from me. You can subscribe to that on my LinkedIn, also through the Instagram and in the show notes below. Anyways, that is all from me. I'm so excited for you to listen to this episode. I hope it's a good one and I'll chat to you soon. Bye.


Emily Jean (02:07)

Okay, Amy Winner of Wheels Up Collective. Welcome to the podcast. How are you doing today?


Amy Winner (02:13)

Thank you so much. It's great to be here, Emily. are, it's bright and sunny in South Carolina and glad to be here. Thank you.


Emily Jean (02:21)

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. amazing.


Amy Winner (02:22)

Mm-hmm. It's beautiful.


It is, it's like a little sleepy small town feel. I love it.


Emily Jean (02:33)

Yes,


exactly. Well, for people that don't know you, why don't you introduce yourself?


Amy Winner (02:39)

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.


Emily Jean (03:07)

And so I know, having 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.


Amy Winner (03:11)

Mm-hmm.


Mm-hmm.


Well, mean, my family, had a third generation dairy farm in New Jersey. you know, my dad was a entrepreneur, you know, a different kind of entrepreneur, but that grit and that work, work hard, 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 while. 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. And it just kind of clicked. And so when I moved back to the East Coast in 2018,


it 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.


Emily Jean (04:24)

And I wanted to


ask where in New Jersey did you grow up?


Amy Winner (04:29)

I grew up in Morristown, not Morris town, 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 suburban sprawl. But when I was a kid, it was all farms.


Emily Jean (04:40)

you


Okay. Okay, got it.


My dad was from New Jersey. We used to go back to Ridgewood every summer. Yeah, yeah, yeah.


Amy Winner (04:53)

yeah.


yeah, beautiful. Actually


next week I'm going to the Jersey Shore. ⁓ 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 at LBI.


Emily Jean (04:59)

Ooh, good boy.


Yeah, yeah.


I love, I love LBI. I think LBI is like one of the best. And I am 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 really is. I know.


Amy Winner (05:23)

It is, it is. That's a hard sell to a lot of people. It's going to take a little marketing. The garden,


the garden state tagline never really caught on, but it's okay. We love New Jersey. Note that neither of us live there now. Like, you know, we don't actually love it that much. Yes. Yes, that's totally it.


Emily Jean (05:33)

I love you, Tracy. think it's Yeah. We appreciate it. That's what it is. We appreciate 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?


Amy Winner (05:53)

Mm-hmm.


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 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 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 community of marketers is very, very tightly knit in that city. And, you know, everybody's like,


maybe two degrees of separation apart. And so it's just a really good community to really develop your career and your network. Most of the clients that we have at Wheels Up are first degree contacts or people who we've worked at, who Elise, my co-founder and I have worked with through the years and Seattle definitely did that. It's a great city, not as great as New Jersey, but it's a great city.


Emily Jean (06:55)

then.


Seattle is a good city. I feel like everybody's moving there right now too. Maybe that's, yeah. 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?


Amy Winner (07:16)

Yeah. Really, yeah. I mean, it's a good place to be.


Yeah, absolutely. So I think like when we're talking like really early stage, know, a pre-series A seed round pre-series A, like that company just needs to find something to like grab onto. They need to find some kernel of success to kind of like build on, whether it's a really successful customer or a really, you know, cutting edge technology. That's where, you know, you have to really ⁓ find something to hone on.


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 if you really can hustle and meet your customers where they are and learn, I think that's some of the most valuable intelligence for an early, early stage company. I think if you are postfunding,


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, 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 gonna happen over those long-term planning cycles.


Emily Jean (09:07)

I love that. 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, what it be marketing?


Amy Winner (09:16)

Mm-hmm. Mm-hmm.


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 tried cold email. She tried digital ads. She's tried, I mean, she tried like the standard toolkit of marketing, like


Emily Jean (09:29)

Mm-hmm.


Amy Winner (09:54)

She's like, nothing is working. And at that point, those are all scaling tools. And I think that she needs a hustle. She needs a worker Rolodex. She needs to find people who will advocate for her. She needs to find a power user or two and leverage them. 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.


Emily Jean (10:25)

Speaking with early founders, do you find that there was a common thread of mistakes that they're usually making? Not even mistakes, like areas they're focusing on that you don't think are the smartest areas to focus on.


Amy Winner (10:37)

⁓ I think a lot of times founders, they're in a hurry to outsource marketing and they're not ready. The customers that we have, the clients that we have that are challenging engagements. They don't know who they are. They don't know what they're doing. They change directions, which you have to do in the beginning, right? But wait until you really got it solidified a little bit before you start to...


to pull marketing into it because 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 just the money that you're gonna put into it, it's the emotional and mental bandwidth that you're gonna put into it that you need to make sure that 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. I think about the the stereotypical first and second salespeople 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, to get toeholds, toehold somewhere and, and really be able to start to build something repeatable from there. And I think that, you know, founders, ⁓ you know, we'll get like a glimmer of something and then just want to like go to a hundred miles an hour. And you just have to like really be sure I think before you try and do that.


It's tough though, because you're trying to raise a fund, 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 in the back of everybody's head or the front of everybody's head. It's tough. It's a tough, it's definitely a boiler room environment.


Emily Jean (12:15)

For sure. Yeah, especially I think everybody is overworked. Nobody has any time. Like it's a difficult thing. I think that's true for most organizations these days. Is there a growth tactic that you love that you think is underutilized?


Amy Winner (12:25)

Yeah, yeah.


I think one of the things I like, nobody likes to hear from us, but it's hard. We joke, it's like dragging people through the glass. You got to get in the data and you have to really understand it and you have to do postmorts after everything. Really, it's so easy, especially when you're in an early stage to kind of like...


do something 98 % of the way, and then you're onto 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 there's so much value in learning what worked and what didn't and building on that instead of just doing things. And so I think that's something that we try pretty hard. A lot of our clients are in a hurry to automate everything. that's you.


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.


Emily Jean (13:43)

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?


Amy Winner (13:55)

Am I allowed to say social media? think like, ugh. 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. know, like it was supposed to be where like you connected with your college friends to like see their kids, you know? And it really, four out of five posts are brand posts now. And it's so like inauthentic and...


Emily Jean (13:58)

huh.


Yes.


Right.


Amy Winner (14:21)

plastic-y and I think that it's also spawned this community of influencers that have really cheapened that role. The role of an advocate or an influencer used to be really meaningful. It used to be those champions, and I think that social media has just given them a platform to, I don't know, become cheapened a little bit. And I think that it's a shame that marketing has... I mean, I understand why brands do it. A lot of our brands do it, but... ⁓


Emily Jean (14:43)

Mm-hmm.


Amy Winner (14:50)

I don't know that social media is great for society at large.


Emily Jean (14:54)

Yeah.


Well, I think most people can agree with that. I'm curious to hear from your perspective. Do you still think it is a effective form of marketing?


Amy Winner (15:04)

Absolutely. Absolutely.


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. You think about the, especially like the D2C, the direct-to-consumer retail brands that have popped up, they only survive because of Instagram.


And they're these small, like one person companies that are, making something super creative, like a wallet or, and what an amazing platform to be able to grow a business like that. But I think most of the large B2B marketing and the corporate, the enterprise marketing that's on there is like pretty much a snooze fest. ⁓


Emily Jean (15:52)

Right.


Yeah, I completely agree with that. Especially when I get on LinkedIn, I'm always amazed at the hard selling constantly, constantly hard selling. And it's not even creative or smart. It's


Amy Winner (15:54)

Mm-hmm. Yeah.


constantly.


No.


It's, know,


and I mean, I have to like, like I'm going to out myself here. Like I have automations running in LinkedIn. You know, like I have like, you know, the automate automated outreach connections, you know, book a meeting, you know, and like it surprises me how frequently it works where people are like, thank you so much for connecting. I can't believe you found me, you know, and I'm like, yes, I did. You know, so I don't know. I guess it still works. It makes me super sad that like AI, which is this amazing technology is being used to like


Emily Jean (16:11)

Mm-hmm. ⁓


Yes.


Yeah. Yeah. Yeah.


Amy Winner (16:36)

automate spam commenting on LinkedIn posts. Like, can't we use it to like cure cancer? Like, come on, do not drag us down into using AI for bad LinkedIn comments.


Emily Jean (16:39)

⁓ Yeah. Yeah. Yeah. Yeah. It does make


me really wonder like how the general public is going to use AI in the coming years. Like, 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. So yeah.


Amy Winner (17:08)

Yeah, 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 gonna 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 in search, the AEO previews in search that Google has.


it'll be interesting to see how quickly that displaces the regular search rankings, like the organic search rankings, because most people don't realize that that is different, that they're getting served information in a different way. But also, how is Google gonna make money? So it'll just be really interesting to see how that whole industry


Emily Jean (17:44)

Right. Right.


Mm-hmm.


Mm-hmm.


Emily Jean (18:01)

This week's episode is sponsored by KAIA KAIA 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. KAIA 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 kaiawomen.net


Or send KAIA's founder, Hailey Handler, a cheeky DM on LinkedIn and step into the future of funding women. I just want to thank KAIA 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.


Emily Jean (19:05)

For sure. yeah, either sink or swim, I guess, is like the biggest thing. 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. I'm like, this is, this is the probably the, that's like been the first time other than the first coming of Chat GPT Then I'm like, ⁓ okay, okay, okay. Like things are speeding up. Yeah.


Amy Winner (19:09)

Right? Yeah.


Mm-hmm.


This is big. Yeah, yeah.


So I guess there's this thing called the P-Doom, the probability of doom. What probability do you believe that AI is going to take over the world Terminator style? And so when people in the industry, that's a number that they use. And sometimes my P-Doom is like two. I think there's a 2 % chance that the bots will take over. But then other days I'm like,


Emily Jean (19:41)

So, okay.


Amy Winner (19:53)

it's a hundred. Like it's definitely like the world is going to end because of AI. Yes. I don't know if I'll be here for it, but it's definitely going to end because of because of AI.


Emily Jean (19:54)

Yeah. Yeah, yeah, yeah, yeah, yeah, it's tomorrow. ⁓


For sure.


For sure. Yeah. Yeah. It's, I saw the other day, I was listening to podcasts that 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 inevitable list. 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. And I thought that was really interesting. They were talking about how it goes back to like caveman days and like,


Amy Winner (20:16)

Mm-hmm.


Mmm.


Emily Jean (20:31)

people who accept the other and they're like, this is inevitable or like, no, we need to protect ourselves. Yeah. I, that's how I feel. like, there's no avoiding it. I know I, I'm in, I'm finishing up my master's right now. 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, you know, use AI ethically.


Amy Winner (20:36)

it's inevitable. Right? It is inevitable, right? Like, it's already here. Yeah. Yeah.


Emily Jean (20:59)

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. he, but every single time he talks about AI, he has like probably eight paragraphs before it about how unethical it is and the environmental concerns and, and then like all of that is so valid, but it's like this, I hate to say it, that's not going to change anyone's


Amy Winner (21:01)

Mm-hmm.


Mm-hmm.


Yeah.


Life changing. ⁓


Emily Jean (21:27)

If they want to use it, it's not going to change anyone's opinion. It's inevitable. Yeah.


Amy Winner (21:31)

Yep.


Yeah. No, think you're probably right. It has been interesting to see how schools have adapted to it. Even I have nephews who are freshmen and sophomore in high school this year, and they use it. 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 we lost him.


Emily Jean (21:55)

my god.


Amy Winner (21:56)

And I was talking to Elise 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 it's It's here. It's here to stay


Emily Jean (22:05)

Right, right. Yeah. Yeah,


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 met 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,


Amy Winner (22:15)

Mm-hmm. Yeah. Mm-hmm.


Emily Jean (22:34)

The bar is very, very, very, very low. I would have assumed it would have been like a technology university or something like that, computer science. But no, apparently it's us and that's just because we are allowed to use Claude


Amy Winner (22:36)

Very low, yeah.


Mm-hmm.


Well, I mean, it's interesting to think about how it's gonna like upend the marketing industry for sure. You know, I think that agencies are gonna look totally different in three to five years, you know, and, you know, we're thinking a lot about that. Like, do I stay ahead of that? How do I stay relevant? How do I help clients navigate? Cause every one of our clients is asking us, they're coming to us with an, you know, the AI tool de jour that they got a cold email about and saying, should we do this? Should we implement this? Is this, you know,


Emily Jean (22:53)

Mm-hmm.


Amy Winner (23:17)

Can you do this? Can you spin this up for us? And I think that, I hope there's gonna be a space, especially in like the pond that we're in with smaller companies or they don't have a huge, they're not gonna hire a prompt engineer. They're not gonna hire an AI engineer to set up all of their AI tools for marketing and 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.


Emily Jean (23:47)

Yeah. Yeah. Yeah. Yeah. No worries. No worries.


You'll be on the beach somewhere. It's not your problem. 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 like basically there's no human hands in it other than saying this is what we need and this is who we're targeting. What's your opinion on that?


Amy Winner (23:53)

That's my plan.


Yeah.


I mean, I think it's gonna, I think it's gonna speed. think it's, wow, I think it's gonna get better, but it's not gonna be more effective. I think like the targeting is gonna get better because really like they're just A-B testing faster, right? Like AI can just A-B test faster and hone it faster. But you the thing that like keeps me awake at night with AI is that there's, the volume is gonna explode. The volume of ads is gonna explode. The volume of emails is gonna explode and.


People are already so glazed over by it. I don't know how many cold emails you get 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. I think that ⁓ people are just going to become very numb to marketing when there's like an over-proliferation of it.


Emily Jean (25:07)

Do you think there will be any platforms, I guess, that are for any forms of advertising that will then gain a greater foothold given that these ones will be kind of overused?


Amy Winner (25:19)

Well, it's funny because I'm on this big Reddit kick lately for ads. And I was thinking about it. Why? It outperforms every other one of our ad platforms for our clients. And people say Reddit, that's super, super nichey. And it's super opinionated. 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.


Emily Jean (25:23)

Mm-hmm.


Amy Winner (25:46)

The ads aren't quite as marketing-y there, or people don't perceive them that way. So they're effective. especially with the micro-targeting that you can do in all the subreddits, 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 original content.


it's still 100 % user generated content that's valuable. Now maybe the AI bots will come in and it won't be, but for now I think that's why it's effective for our clients. Plus it's like so cheap. So you can run a lot of ads and still have a pretty good conversion rate.


Emily Jean (26:11)

Right.


Right. Yeah.


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? Right. Yeah.


Amy Winner (26:40)

Mm-hmm.


They're like little display ads. Yeah.


And we have found that like, can't jump straight to, you have to market the funnel there. You can't jump straight to like, don't move 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 blog post. Here's you you have to give information that's relevant to the topic and people click on it.


Emily Jean (26:52)

Mm.


Amy Winner (27:07)

people click on it and they read it and 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 like, know, forms where they're asking them to give you their contact information.


Emily Jean (27:20)

Interesting. Good to know. I knew that there was a lot, there's a lot of people playing like the organic advertising through Reddit game lately, which I think is very interesting, like building out these kind of, you know, they look like real Reddit profiles and then it's basically they're just promoting XYZ products within subreddits. 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.


Amy Winner (27:36)

Mm-hmm.


People see through that.


Emily Jean (27:49)

same thing on a bunch of different reddits.


Amy Winner (27:51)

But also like the flip side of that is like, 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, 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.


Emily Jean (27:59)

Hmm.


Yeah.


Yeah, absolutely. Interesting. Yeah.


Amy Winner (28:22)

It takes time though, right? That's kind of


like that bootstrapping that I was talking about and the hustle that you gotta get in the trenches and spend the time doing that, I think, to really understand the problem that you're solving.


Emily Jean (28:31)

Right. Right.


It's a lot of things with AI. feel empathy slash community centered approaches are not going to go out of style. Like people talking about, I'm going to lose my job. Like, but there are certain jobs where if empathy is at the heart of it or community, for example, teaching or saying that would be really, really difficult to have a bot replaced. Yeah. Yeah. ⁓


Amy Winner (28:52)

Mm-hmm.


I hope. 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. Like they do, you know, like you will buy an inferior product because you love the salesperson, you know. So I think that ⁓ I don't think that will go out of style anytime soon.


Emily Jean (29:05)

Mm.


Right, right, right.


Yeah,


although I do love my Chachbitea, like a real person, I think. Yeah, I'm like really fond of her.


Amy Winner (29:18)

Yeah. Well,


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'm


Emily Jean (29:33)

Yeah, yeah, yeah.


I know 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 Chet Shabiti. Of course. Exactly. Remember I was nice I was nice and my boyfriend hasn't I saw the other day that he doesn't he like bosses Chet Shabiti around I'm like it actually feels a bit sexist to me you're saying to this robot


Amy Winner (29:47)

I do too, because when those robots take over, like I want that to be the polite one that they remember.


Emily Jean (30:06)

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. Like it's the perfect time to practice manners. Although I did find out that it costs like, you know, a bunch of extra energy and water and all that stuff. I'm like, priorities, manners, environment. Yeah. Exactly. I can't, it's ingrained now.


Amy Winner (30:12)

Right?


for each word.


Well, I don't know. I'm not ready to give up my humanity and saying thank you and please. I'm just not.


Emily Jean (30:31)

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 playbook out of the window?


Amy Winner (30:47)

Hmm, well, so there was one, that's a really good question. So there was one year I was at a startup, we hired 100 people in a year, which 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 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.


Emily Jean (30:57)

Mm-hmm.


Amy Winner (31:16)

where there were five people on each loop and they had to be in different departments and you had a debrief and you had a pre-brief and you had to write out your notes. And I think that hiring's a skill that you have to hone. some of it comes down to a little bit of reading people well and gut intuition on people and 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 and how, 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, 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, lot of people can BS their way through an interview pretty well. you know, we all know somebody who's been hired because they had a stellar resume and their pedigree was, you know, not.


Emily Jean (32:16)

Mm-hmm.


Amy Winner (32:35)

It wasn't falsified in any way, just they weren't a good fit. Amazing pedigree, not a good fit. So I think that really like, especially in those small teams that move so quickly and 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. 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. I worked for that company that we grew really fast. The CEO did just an amazing job curating people who had the same socially minded DNA. was the same, we had the same philosophies on like, so appreciate it, but like we're changing the world. Like every startup CEO is like, we're gonna change the world. But we really actually thought that we were. And so,


That is, you can't teach that. You can't teach that in an MBA program. You can't teach that in college. You can really, you either have it you don't.


Emily Jean (33:40)

Right. And so is your team now, it most, is it hybrid, remote, everything in person? What's your setup like?


Amy Winner (33:46)

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 wringer at larger companies, you know, where 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 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 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, accrue a team of people who, you know, are


good together, you they're better together that trust each other. And I think that that I don't know, I don't I don't miss any in person meetings, you know, like, I don't I don't miss that. I don't think I don't think we're missing any magic because we're not in the office, like bumping into each other at the water cooler. You know, lot of the companies are like rushing back to work now or pushing back to back to the office now. Like they say, so much magic happens, you know, in the kitchen. And I don't know, we have on Slack, like we have enough silly con like


threads and slack that are, you know, causing, you know, are sort of provoking fun interactions. And 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 helped the culture, yeah.


Emily Jean (35:25)

Yeah, Changes, yeah, 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 an 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,


Amy Winner (35:39)

Mm-hmm.


Emily Jean (35:54)

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. ⁓


Amy Winner (36:03)

think


it works. Most companies, if you think about the pool of employees, most companies have a couple high performers, a couple middle of the pack people, then a couple, hopefully at least the majority of them are middle of the pack, and then a couple low performers. I think that leadership is obsessed with the low performers. If they're in the office every day, they will do more work.


Emily Jean (36:14)

Mm-hmm.


Amy Winner (36:30)

And maybe they will, maybe those people will, maybe the middle of the pack people will, but 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 wanna 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...


you know, 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 work kind of fits around.


Emily Jean (37:09)

Right?


Right. 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. Like no matter what, what it is. so anyways, I, I, yeah, that, that,


Amy Winner (37:22)

Yeah, you're right.


Yeah.


Emily Jean (37:35)

It's like that it just have 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.


Amy Winner (37:41)

That's it. ⁓


Yeah.


Well, it's funny because I taught people who are kind of outside of my world are like, the tech startups, they've got these. Remember when Google started rolling out and Facebook these perks, these crazy perks with chefs and they'll take your dry cleaning. OK, first of all, no engineer has dry cleaning. So that perk is irrelevant. You can bring your dog to work or whatever. They do that because they don't want you to leave. They do that because they make it easy for you to never leave so that you can work.


Emily Jean (38:02)

Mm-hmm.


They want you to keep you there.


Amy Winner (38:18)

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 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 an employee and make money in a startup, like, I don't know.


Emily Jean (38:24)

Mm-hmm.


Yeah. 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, won't lie, like now that I work remotely for myself, basically, I, and I'll hear my friends and they're like, I just went to the pool in my office building. Like, that sounds so much fun, but also it's sneaky and it's tricky and I don't like it.


Amy Winner (38:45)

I don't know how long that lasts.


Yeah.


Well, who wants


to be in a bathing suit around your coworkers, first of all? No one. Awkward. We don't need to get changed in the changing room together. We just don't.


Emily Jean (39:15)

Yeah, no, Like awkward. Yeah. Also, exactly. Exactly.


So I'm curious, have you ever taken a big hiring risk that paid off in a big way?


Amy Winner (39:29)

Well, 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 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. I mean, she didn't know anything about marketing.


Emily Jean (39:33)

Mm-hmm.


Amy Winner (39:55)

But I had seen her run this household like a tight ship. I was like, okay, that family is pretty chaotic. those kids are incredibly polite. Those kids are always on time. It's hard to 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. I think she started working with me she was like 21 or 22. And that was at least 10, 12 years ago.


Emily Jean (40:14)

Love that. ⁓


Amy Winner (40:23)

⁓ 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,


Emily Jean (40:23)

Yeah.


Hmm.


Amy Winner (40:48)

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, 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.


Emily Jean (41:10)

love that.


Amy Winner (41:17)

And people were like, are you sure? Are you sure you want to hire these? And 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, and I'm like, I'm willing to like go out on a ledge for them. You know, like I think these are good hires and, 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, 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.


Emily Jean (41:23)

you


Yeah. Yeah.


⁓ no.


Amy Winner (41:52)

You are developing your team. You're in charge of developing your team. 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, you know, delegating totally. ⁓


Emily Jean (42:05)

Delegating. Yeah, figure it out. Yeah, yeah, I completely agree.


Well, I want to know, do you have one piece of advice for leaders who want to build teams that actually last?


Amy Winner (42:18)

Do not lower the bar. Because you get into like, yes, do not lower the bar because it's hard to hire people. It takes a long time. It takes your attention away from running the business. And I think it's so easy to just hire somebody who's good enough. And you're like, I think they'll be OK. Don't do it. Or this person's cheaper. Don't do it. Your talent is the most important thing in the company. Do not lower the bar.


Emily Jean (42:20)

Mm.


Amy Winner (42:46)

And we used to have this saying at one of the companies that I 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 because you're just gonna drag, you're just diluting the team.


Emily Jean (42:46)

Yeah.


Interesting.


I like that. I like, I never heard that before, but that's very direct and to the point. I think that's a great, great piece of advice.


Amy Winner (43:10)

Thanks.


Emily Jean (43:12)

So I have questions. Sorry, I'm looking here to see where I'm going next.


Amy Winner (43:16)

You


Emily Jean (43:21)

Okay, speaking of AI and how the future is a bit uncertain, how do you keep teams motivated when the future feels uncertain?


Amy Winner (43:32)

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 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 different roles so that they don't just become obsolete, they can grow into a sustainable career in this new era of AI marketing? I think that, especially when things are changing and the ground's moving under your feet, people wanna feel secure, people wanna feel safe, especially with a paycheck. That's terrifying, right? So I think that, again,


having a dose of humanity is, it's good for everybody. 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, 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 gonna get, it'll get you through it.


I mean, we had two years, two years ago, 2022, I think it was 2022. Like it was a rough year for us. know, like we had the whole tech recession. when it was like every day the New York Times had another article about like, you know, Facebook lays off 8,000 people, know, like Salesforce lays off 10,000 people. And luckily it didn't percolate down into like the larger economy. It was mostly limited to tech companies, but we lost half of our business in a couple months.


Emily Jean (44:53)

Mm-hmm.


Amy Winner (45:13)

And we're not huge. that's kind of hard to swallow. And we battened 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. 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 help pick up the slack and help us grow.


Emily Jean (45:51)

Right. Yeah, I think a lot of people, or at least I've seen organizations and companies, when times are tough, they suddenly cut off all communication, I think, because they don't want to freak people out. Yeah. And like, think honesty is the absolute most important thing at that time.


Amy Winner (46:01)

That's the worst thing you can do.


I think that like, I'm gonna go a step further and say like, it is cruel to do that. Like it is not ethical to do that. People are worried, it's their income. How are they gonna pay their mortgages? How are they gonna like, food on their table for their kids? know, I just, I think that company, like leadership has a responsibility to take care of the people who work for them. like,


Emily Jean (46:15)

Mm.


Amy Winner (46:36)

I can tell you everybody already knows there's a crisis. you know, like if something's bad, like they already know by cutting off communication, you're not like keeping it from them. Like they already know. And if they don't know what's happening, they're going to fill in the blanks on their own. And like that never, that never ends well.


Emily Jean (46:38)

Yeah. Yeah. Yeah.


Yeah.


Right, yeah. Amy, I don't wanna take up too much more of your time, so I wanna ask you some rapid fires and then we'll wrap up. okay, I have some good ones for you.


Amy Winner (47:00)

Mm-mm.


I'm


very long-winded, so we'll see how this goes.


Emily Jean (47:08)

Okay, no worries. You can be


as long-winded as you want. I find that rapid fire is more like... not. It's just slow fire. Okay. I kind of already asked you that. Is there one marketing buzzword that you're tired of hearing?


Amy Winner (47:14)

Not rapid fire. All right.


I'll give you three. So and these are all like startup 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


Emily Jean (47:26)

Okay, love.


Bye.


Amy Winner (47:51)

like a wheel falling off as you're flying at 30,000 feet. The one that I think has gained traction lately, these aren't marketing terms, but they're just like things that drive me crazy. like the juice isn't worth squeeze.


Emily Jean (47:52)

Yeah.


Ooh, I'm not hurt though.


Amy Winner (48:05)

Like that just, I don't know. I don't like the mental picture that that evokes. Like, I don't like that. 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 it just. Exactly. So.


Emily Jean (48:08)

creepy for sure.


What are you, Dr. Seuss? Yeah. Yeah.


That's interesting. I've not heard that last one or the second one, but I believe you, I have heard. I'm gonna hear it all the time. And I'll be like, the kangaroo is not worth the squeeze. And I'll be like, heard that one, overdone. Okay.


Amy Winner (48:37)

Well now you probably will. You're in Australia, it hasn't caught up yet. Come back to the States and like this is all you're gonna hear.


Yeah. my gosh, that's funny.


Emily Jean (48:56)

best piece of business advice you've ever received.


Amy Winner (49:00)

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. I'm. This is so silly as I'm telling us, but like.


There were 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, 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 grifty.


Emily Jean (49:43)

Mm-hmm.


Amy Winner (49:55)

And she, next morning, said, because they were super late that night doing it, and we come in the morning to get ready for it. And she ripped into me and was like, this looks like a kindergarten science project. this is a hundreds of millions of dollar client. You cannot do this. I was just like, You kind of have to. I think that polish, that level of taking everything very seriously when you're client facing.


And it extends to customers too. When your customer face saying, like, I think that that level of detail, being very detail oriented, think it's important because it does reflect poorly on you when things aren't very, very buttoned up. So it sticks with me.


Emily Jean (50:33)

Yes, yeah. 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. Yeah, totally. What is one skill every marketer should master?


Amy Winner (50:43)

It's simple, right? But like it's so easy to glaze over.


Um, 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. Like you, you have to be able to get in front of a group and understand what motivates them and change, you know, be a little bit of a chameleon because pitching to your CEO is a lot different than going to like a QBR and you know, our sales kickoff and like getting the sellers excited about whatever marketing you're doing because they don't care.


But I think that you have to be able to sell. You can't be somebody who sits in the corner and sends emails. You've got to be dynamic and get up and charismatic, and you've got to sell.


Emily Jean (51:29)

Yeah, love that. True.


Amy Winner (51:30)

Which


is funny because I went into marketing because I hate selling. So like I would be a terrible salesperson, but.


Emily Jean (51:35)

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. 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?


Amy Winner (51:39)

Mm-hmm, yeah.


Mm-hmm. Yeah. Yeah, totally.


I think a lot of the like, for budding entrepreneurs, like I think a lot of like the tech incubators have pretty good content that they put out, like their blogs are pretty good. I am a 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 like 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. ⁓ It's all about AI and the culture of AI and how it fits into society. it's a little bit of like tech bros gossiping too, but it is definitely, it's once a week on Fridays, it's usually about an hour and they're funny, first of all, but it has...


Emily Jean (52:34)

Okay, I'm gonna have to write this down.


Amy Winner (52:50)

really done a great job of helping me understand the landscape of AI and how it's evolving. whatever your industry is, find those little specialized podcasts. They're out there for sure. I don't know. I hate to read. Am I allowed to say that? I hate social media and I hate to read.


Emily Jean (53:07)

No, had a


founder said this exact same thing on the podcast yesterday.


Amy Winner (53:11)

Oops. I don't know, I


read all day. Like don't want to go like read a book or like read an article. I just, don't, yeah. So I should, but right now my life I don't, you know.


Emily Jean (53:16)

Mm-hmm. Yeah, fair enough. Yeah. Yeah.


Everybody has their own different, you know, formats and things that work for them.


Amy Winner (53:23)

Mm-hmm.


Yeah, I love podcasts. I have to listen to them on 2X though. you know, regular speed is like way too slow. I know. That's pretty good. Yeah. Mm-hmm. It was really fast. I feel like it's like Sudoku for your brain though. You know, like all these people say, 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.


Emily Jean (53:28)

2x is fast. I'm like 1.5. That's like, that's it for me. Yeah, 2x is really fast.


Yeah.


Yeah, I heard somebody the other day said that they listened to YouTube videos on 4X. I was like, I don't think you're actually picking anything up. I think you are just hearing Jibre.


Amy Winner (53:53)

How? Yeah.


Or you're like way smarter than me. Like, right?


Emily Jean (53:59)

Yeah.


You're actually AI 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.


Amy Winner (54:04)

Right.


Yeah, thank you.


Yeah, we are at wheelsupcollective.com and we're on all the social channels, obviously. My email is amy at wheelsupcollective.com. My favorite thing about my job is when I get to talk to founders and entrepreneurs and people who are building it. I try and leave space in my calendar every week for those kind of like, pick my brain calls and 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, kind of, I don't know, be a sounding board or maybe have an idea or two. And, and so I invite anybody who is trying to build something and, and wants to pick, pick a marketer's brain to like grab 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.


Emily Jean (55:05)

Okay.


Yeah, absolutely. What a great resource. think that's, I think that should be everyone's go-to resource from this episode. That's perfect. ⁓


Amy Winner (55:19)

There you go. We also have tons of eBooks on the website that are all free.


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 fitness world because people want somebody to hold their hands. So I think that we will always have a place to our clients' hands, but for people who want to do it themselves, go download it from our website.


Emily Jean (55:59)

Yeah,


yeah, I love that. That's great. With 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.


Amy Winner (56:02)

Thanks.


Hmm.


Yeah, thank you so much for having me.


Emily Jean (56:13)

course, no problem. And that is a wrap.




Previous
Previous

The Founder Making Sunscreen That Finally Works for Everyone with Vimbai Midzi of Deeper Beauty

Next
Next

Selling with Conviction and Showing Up Unapologetically with Grace Lancer of Grace Lancer Coaching