
In this episode, Ashley pulls back the curtain on what’s coming up in the next few episodes and shares her personal approach to investing in the right rooms. From the questions she asks herself before saying yes to an event, mastermind, or...
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Welcome to the Win with Paid Ads podcast for small business owners, entrepreneurs and really anyone who has anything you want more people to find. Whether you're starting from ground zero or scaling an eight figure business, you are exactly who this podcast was created for. Because you being the best kept secret helps no one. Right? That's why in every episode I'll show you how you can use paid ads to hit your goals 10 times sooner. It's time you finally learn how to win with paid ads. You or someone on your team can do this. I'll show you how to score and be known by more. Let's get started. I'm really excited to share with you on these next few episodes of the podcast. And also on YouTube, we're doing a test and I really want to see what your feedback is on this. We actually have. So if you've listened to the previous episode, I had my stylists Charla and Emily and I have a code. If you do decide to work with them below this podcast or YouTube video, if you use code Ashley to work with them, there's a special incentive there. So if you listen to that episode, we have some content that's exclusive exclusively on YouTube. It's a little bit of them styling me for my in person event and walking through like what we should change and why and then doing almost like an episode of what not to wear in my closet. But what that means for you is you're gonna learn all the mistakes that I was making and how they think about style. And so go watch on YouTube and I really feel like you're gonna love it. And it's just, it's style, right? It's so visual. So you seeing those next two episodes on YouTube are gonna be really, really cool. And then also something else that we're doing on YouTube is we actually did a kind of documentary style video. Thank you, Robert for the batch day where very recently we I met with this guy named Ryan. Ryan is incredible and he has done some videos for some of the top entrepreneurs in the world. So if you have ever, ever heard of Grant Cardone and there's some other people that I know that he's worked with that have millions of followers or did have, do have. And so he's really, really good at video content and getting a bunch, bunch of batch content. And so Robert was here and what we did is he kind of did a behind the scenes of that day with Ryan and his team and how we got over 100 videos in a single day. And so that is also on YouTube. So go take a look at that. It's one of those things. I was like, should we put the audio on the podcast? But I really think it's going to be really cool for you to go on YouTube and see the story and piecemeal. And honestly, it is so behind the scenes. Like Robert was there right when we started the day and he was like, how are we going to make a hundred videos in a day? And. And you're gonna get to see. So go check that out on YouTube. It's gonna be really cool. All right, so what I wanna do is I wanna talk to you on these next few episodes about different rooms I've invested in, why I've chosen to invest in those rooms, and how you can think about who you should be in, in, in the right rooms with. And so we, we kind of have this whole, whole series that we're like putting together and it's required some planning and some thought, but it's really, really cool. So on the next few episodes, I'm gonna talk about other rooms I've invested in and the things I've learned from those rooms to compress time for you too. And so get excited because the next one episode that you're going to get is going to be about different, like short term rental and investing and how to advertise that. And the rooms that I've gotten in there, and then the one after that is going to be Alex Hormozi in the room I got in with him and I'm getting to meet him in person and I'll share with you what that's going to look like. So there's some really, really good stuff coming. But also, don't forget to go check things out on YouTube. You're going to love it. All right, so before I get into those episodes about why I' chosen to invest to be in different masterminds and different groups and learn different skills, one of the questions you might have is, well, how do you pick the right person to be a mentor or guide you and how do you know it's the right investment? And so I actually wanted to share with you some filters that I have when I'm thinking about investing and give you a little bit of research that I've done on how do you decide of those mentors when you pay to get in the room? How do you know what, what pieces to listen to when you get in the room? So that's what this is going to be about. It's going to be really good. And by the way, speaking of rooms to get into. If you haven't gotten in the room for the Win with paid ads challenge, you belong in that room. It is a great opportunity where you can be in the room with other six, seven and eight figure entrepreneurs, from influencers and creators to online boutique owners to in person local service providers. So whether your business is online in person, B2B. B2C. Leads based, product based, you will love the Win with Paid ads challenge where we break it down over five days. How you can win through your messaging, your setting, your targeting, your testing and your scaling and messaging is what you say, setting is where you say it, testing is how you improve it, and targeting is who you're getting those ads in front of and then profiting and scaling is what you really want from all of that. So we're gonna break it down. So as you think about rooms to get into, I would love for you to be in that room. It's really special. So let's dive into a few things. Number one, the qualifications I have when I'm trying to decide who am I going to invest into? And then like, how do you know? Like, do you have too many mentors? Like, how are you? Are you learning too many things? Like, so often I've heard people say, well, I'm already doing this, so I can't do that. And I'm like, what if that, the fact that you're doing that is the very reason you should do this next thing and how to think about it. So that's what I want to share with you today. So here are four qualifications and questions that I ask myself before I invest to be in a room. So the first one is, are they investing in themselves? Like, are they actually paying money to be in rooms with other people? Have they pulled their like, future and their revenue forward? And if they are not investing to be in other rooms with other people, then I am not. I'm probably not gonna move forward, right? Because I really want to see. Are these purple. Are these people just trying to make money? Like, is it just about the money or are they truly invested in growing themselves so that they can grow other people? That is what's core and like, so important to me is I want to invest in myself, not just for myself, but because of how much it impacts the people that I and the men and women that I get to work with in their businesses. When I'm putting new information in my brain, it's like they think they're signing up for ads. And one of my favorite things, even, even yesterday or Even, gosh, I feel like this happens every day. A client comes to me and says, wow, this was so much more than ads. And that's my goal, is to bring. Bring you in through the lens of advertising, paid advertising, and then delight you on the other side with how much more can I. Can we help you about, like, what you're advertising, why you're advertising, what that whole machine looks like. So, number one, are they investing in themselves? Number two, have they failed more than I have on this particular subject? That's really important to me too. I want to know that they've not just been successful for themselves, but they've also been successful for other ones, which is, have they been that. That's actually my second an third questions is, have they failed more than I have and have they succeeded more than just for themselves? That's what, that's what I. And what I really mean by that is, is the strategy that they're using that they're selling you, is it just working for them or is it working for their clients? So are they investing in themselves? Have they failed more than I have? And is what they're doing benefiting more than just them? I had someone recently say, well, I just got this result for this one person, so I think I'm going to do this for other people. And I get that. That is exciting and I get that you want to share that. It's like, but don't go advertise this as a huge thing that you've done when you've actually not tested it internally. So many people get a result one time and they're like, yay, I can teach this. I'm like, you have not experienced what time can teach you. And that is like, that. Some things aren't going to work out as you plan. Some things aren't going to go. You can't know how to correct something until you've experienced all the things that need correcting. And that's just a gift that, like I've said, only time can give you. The last qualification that I have is I have to think, well, this may not be a qualification for them, but a question that I have to make sure I ask myself. And it is, what is the cost of not doing it if price is what you pay and value is what you get, cost is what happens if you don't pay, right? So I really ask myself, and I say, will I lose more money? Will I lose more momentum? That's the thing we don't think about often. It's like, what not only will I not get this, but if I'm in momentum and I'm investing and an object that stays in motion stays in motion, and I'm like, I'm always looking for the next move. If I just, like, have invested, have invested and then stop, and I'm like, you know what? I'm good. I know enough, and just start selling myself out of getting in rooms with other, other things. I'm losing speed. And what does that lack of speed, momentum cost you? You know, if you close your eyes and you think about a mountain, you think about the side of the mountain. That's the part where you're actually going uphill, right? Because for everything, there's an equal and opposite. So if you're going uphill, there must be a downhill. And so if you're going uphill, it takes so much energy and work to get to the top. And as you get to the top, you're like, okay, I'm finally starting to feel and see and experience the fruit of my labor. And what you really want is to catch some of the momentum. You actually want to let gravity do what gravity do and pull things down and grow. And so I really like to think about, like, how long has it been since I've invested and been uncomfortable? Like, oh, it's been a couple months. It's time for something new, right? So what is the cost of me not doing this? That is the question I like to ask. So those are the things that I go through in my brain as I'm deciding. And here are a few reasons of why those are what I ask. So when you start getting feedback from other people, say you do jump in. And you know, someone has asked me before. They're like, well, I already have. Let's just pretend you have a lack of knowledge or lack of skill, depth in sales. That was my experience. I'm like, okay, I need to pay for sales skills. And then I was like, okay, what if you have a lack of depth and experience in advertising? Okay, well, I don't have to pay for the advertising. That's what time has given me over the last decade. But say you're like, okay, I don't have sales. I need sales. I don't have advertising. I need advertising. And it's like, for me, I said, well, what ties and relates to what I do well? Video. I just wanted to remind you really quickly that if you haven't joined the Win with Paid Ads challenge, the doors are closing soon. And just as a refresher, this is five days of you and or someone on your team learning my five part strategy to scale your paid ads. So day one is messaging, which is what you say and how you say it. Day two is setting, which is all the different places you can place your ads. Think Google Ads versus YouTube, Meta or TikTok. Day three is targeting, which is how you can get in front of your exact right person. Day four is testing, so you can know what to test and how to improve your ads. And day five is scaling and profiting and how you can 10x whatever you're spending on your ads now so that you can have more profit and return and impact, which is ultimately what you want, right? So click the link below and I cannot wait to see you in the win with paid ads challenge. A lot of what I do is video content. So what I did is I paid to get in a room with someone that was really, really good at video content and organic content. Because what I know about advertising is I can take a great organic video and turn it to an ad in less than five minutes. And so it was smart, a smart investment for me to say, who's the best at video content? How can I learn from them? What does that mean for me? I get to create better video content. But what it really means is you and all my clients get to benefit from learning what I've learned about creating good video content, which ultimately is better ads. So they all stack together, right? I think a mistake people make is they think there's too many cooks in the kitchen. Well, I want you to think about it like this. I want you to envision you are building a championship football team. You would not hire four head coaches for your championship football team, would you? No, that would be crazy. But what you would do is you would hire a head coach, a defensive coach, an offensive coach, and a special teams coach. Right? Each own their own lane and together they create a winning team and a winning system and a winning machine. That is how I want you to think about you investing in your business. It's like, okay, you don't need four advertising coaches. That would not be smart. But what you might need is a head coach over here, an offensive coordinator, defensive coordinator, et cetera. Like, it's like, what are the different lanes you need? And get the coaches and the experts in those lanes specifically. Now, I have had people come to me and say, well, I already took a Facebook ads course and great news so far. I'm going to knock on some wood. I don't think that's wood. I'm not going to break anything. But I'm just pretending, right? So so far, we have yet to have a single person after having thousands of business owners and entrepreneurs in our programs say that what we sell for advertising training is similar or even remotely close to what they've ever paid for before, which is exciting. A lot of people are like, well, here's meta ads. Here's this. And great, that's helpful. And also, that's one piece of the puzzle. And so what we've done is created this massive puzzle that, in my opinion, no one else has created in the way that we have, with the experience that we have, with the depth that we have. And so when you think, well, I've already done ads over here, I promise you, you've never done ads this way. That is for sure. And so as you think about all the different investments you make, I'm thinking about this. I'm like, I am creating a championship team. And a championship team means I am. And me and my team are experts in all of these different areas of the business. For us to scale and build this advertising empire of just being the household name when it comes to you advertising your business, it's like, oh, you have a business. Oh, paid ads academy. Have you done the playbook? Have you done these things? That's what we're creating over here. And to create whatever that is for your business, advertising is a piece of your championship team. And so finding the right head coach for that, how awesome that we found each other, which is really, really fun. So once you have thought about creating your championship team and you have this advice, because what you don't want is conflicting advice on the same subject. What you do want is different advice on different subjects. And then what you do with that advice is you anchor it to your own goals. So there's the study from the Harvard Business Review, and it says that entrepreneurs who aligned their decisions with the stage of growth they were in were 3.6 times more likely to scale successfully. Here's what that means for you. Do not do things that are not based on where you need to be and where you're at with your scaling. I think so often we want to go from level one to ten immediately. But in order to get from the first floor to the tenth floor, you have to go through the second, third, fourth. And so many people, they want to get to the 10th immediately. And if you actually don't do the steps that are the sweat and the blood and the. Just the. The challenges that come with walking up each of those stairs, you will not be prepared to Actually lead on that 10th floor, you have to go through through in order and accomplish. It's like I remember having a little Game Boy on my way to church in the back of my mom's expedition, my little red Game Boy, and I was playing Mario Brothers. It's like I was doing and I was, and I was so excited to get to the next level, but I just couldn't get to level 10 without going through level 1, 2, 3, 4, 5, 6, 7. In fact, you wouldn't have been prepared or understand how to navigate 10 if you hadn't been. And so that is why being okay going through those steps as you get to the next level and evaluating where you're at in your stage of business and having someone who's been through those stages in business and it's been to those next levels to say, hey, listen, on stage three, there's a trapdoor over here. Like, that's the type of feedback you want and that's why you want that mentorship. So the other thing is, according to CB Insights, it said 42% of startups fail because they build something the market doesn't want. And so on one of the future episodes, I'm going to talk to you about how I am actually want your feedback on something I'm building. And that no matter where it is in your business, being able to get feedback that you know is something that someone wants to solve versus what you think is a good idea, like building something that you know works and what's really cool about. As you think about rooms to invest in and mentors to get in the room with, it's like, who can you actually work with so that you're not having to test because they've already done the testing so that you don't have to assume you can just consume what they've done. That is the goal. The other thing I want you to think about is just limiting the choice overload. So if you've ever felt like, I mean, this is so funny, two nights ago I'd had a day and it was my full coaching day and I had worked with so many entrepreneurs. It was a great day. I was feeling just so fulfilled and accomplished. But I've made a lot of decisions. And so I went into the basement and we are working on finishing this one room in the back of the basement behind the gym. And we were having to move some of the stuff that was in the basement out of the basement. And Kyle comes to me and he's like, hey, Ashley is like 8:30 at night. We just got the boys to bed. I'm like, just about to get my bone broth and sit down, put on my red light or my green blue light glasses. I was going to sit in bed and just breathe. And he's like, ashley. And I was like, yes, babe. So I come downstairs and he's like, hey, where should we move the washing machine to? I just looked at it and started crying. I was like, I don't know where the washing machine can go. I, like, can't handle another decision that is called information overload. Right. And so what I don't want for you is to be an information overload, which is why I think one of the things that I've had to tell myself is I've made enough decisions today. And what I really love is being able to have someone that has already made those decisions so that you don't have to be the one to decide. I wonder where I should put the washing machine. It's like, oh, we should put it here for these five reasons that saves you. Like, finding the right room to be in. Saves you sanity. We talk about saving money and, like, money growing the business. Yes. You can't have a business if it doesn't have profit. And you've got to get in the rooms with people that are obsessed with helping you create more profit in your business. And I am obsessed with that for my company, for my business, and for my clients. And you need someone to help you eliminate that choice overload or that decision overload. And when you're sitting there in ads manager and you're like, well, I think I know what to do, it reminds me of how my coach said, just because you're selling doesn't mean you can sell. Just because you're getting leads doesn't mean you're the best at getting leads. Like, you can improve this. And you might be making some mistakes you don't even realize, but you're telling yourself you're okay with it because you are getting some results. But what if your results could be 10 times better by having a professional take a look at it and guide you on why. The last few things I was thinking about is there's a difference between being proven and being popular. So popular, there's a lot of people that know about you. Proven is different. And so there's this. It says, Edelman's Trust barometer says that 65% of people trust peers with direct experience. More than just gurus or influencers that are popular. In fact, there's a little bit. Sometimes there can Be a little bit of hesitation and reservation when you see someone that has such a large audience for one thing. It's like there's this balance. It's like there's credibility because they build something so awesome. But there's a little bit of like, are they still in it? They still feel it? Do they still have the care and the depth? Are they. Are they there still? And so finding someone that can be that person that's like you legitimately and specifically matter, that's a big deal. And that is something that I would say the team and I are so good at is we have created a way as we've scaled this business to say we want to make sure that every single, like, business owner that we get to work with. I'm like, I. I was on stage at Launch youh Ads Live, which I actually want to do a whole recap of coming up here soon. And it's like there were 200 people in the room and there was only one person's name I didn't know, and it was because it was a teammate of someone that I'd never met. Like, I. We are so committed to knowing every single client and who they are. And so for me, that's something that matters to me is to just really look at is this popular or is this proven? And last but not least, the last filter I think about when I'm trying to make moves and as I. Because you're about to see on the. On the coming episodes, a few rooms I invested in and why and what I've learned and my one takeaway and how I approach those rooms. But it's super important to use what I like to call the skin in the game filter. And this is what I want to share with you is people who have skin in the game, like there's a risk or there's an investment, often give better advice. And it says that entrepreneurship and mentoring or it says. Research on entrepreneurship mentoring found that founders paired with active business owners saw a 27% higher success rate. And all it really means is that there are people that have skin in the game for what you do. Like, think about this. Just think about it. I'll give you an example for my business. I have skin in the game when we work together. Why? Because I want you to win. Because my whole business is built on you winning with paid advertising. And when you win, we win. Because when you actually win and it's. And you have a especially. I mean, gosh, it's not even especially. It's just everybody, whether you Have a small audience or a big audience, Both of those are a win because it allows us as a team to say, look, they had no audience and no following and nothing established. And they did six, seven figures. Look, she had a million followers. She was already at this. But we took her from here to here. That is winning, that we don't win. If you don't win, we have skin in the game. Finding some way with a partnership where it's like, no, I'm actually obsessed with you winning because, number one, it makes my heart happy for you to win. And also it helps us be able to grow and have credibility to keep doing what we love to do. That is cool. So find someone who is not at a level where you feel like they don't. They don't care. Like. Like someone who has skin in the game and sees it and feels that that's what you want as you think about those rooms. So that's why I'm going to share with you in these next episodes now a few rooms I invested in and what I have learned. And so here's a summary of what I want you to ask yourself. Does this person, does this investment align with my stage and my goals? Has this person tested and is it proven? Am I avoiding information overload by getting the right team for this championship team I'm building in my business? Does this advisor have relevant recent experience and do they have skin in the game? If you ask yourself those five questions, it's really going to help you as you make an investment in working with people that can really elevate you and speed things up for you. And I'm so grateful that I've done that in my business, too. That's why it's such a. Such a big deal. So if that was all helpful for you and you are still thinking, like, how can you find the right room for you to get in? You are who the Win with Pay Dies Challenge was created for, and I would love to get to see you. So click the link below this podcast or this YouTube video and join the room. And if you're listening to this, the timing could be really interesting because we're only doing one more for the rest of the year, depending on when you're listening to this episode. So we cannot wait to see you and get ready because there's some good stuff coming in these next few episodes about rooms that we have invested in and what we've learned. I cannot wait to see you on the next episode.
Host: Ashley Brock
Date: August 28, 2025
In this episode, Ashley Brock dives into her personal decision-making process when choosing which masterminds, groups, or mentorship "rooms" she invests in. Sharing practical questions and mental filters, Ashley explores how business owners can evaluate rooms, mentors, and investments that accelerate growth and avoid stagnation. This episode functions as the foundation for an upcoming series where Ashley will break down the results and insights she’s gained from specific investments—with an emphasis on actionable criteria anyone can apply immediately.
Ashley shares her personal checklist for evaluating mentors, masterminds, or coaching programs:
“If they are not investing to be in other rooms with other people, then I’m probably not gonna move forward.” – Ashley ([05:32])
“Is the strategy they’re using…working for their clients, not just for them?” – Ashley ([06:37])
“Price is what you pay and value is what you get. Cost is what happens if you don’t pay.” – Ashley ([08:15])
“You wouldn’t hire four head coaches... what you need is a head coach, a defensive coach, an offensive coach… each own their own lane and together, they create a winning team.” – Ashley ([11:01])
“Finding the right room…saves you sanity. We talk about saving money… but you need someone to help you eliminate that choice overload.” – Ashley ([17:24])
On misleading "proven" claims:
“So many people get a result one time and they’re like ‘yay, I can teach this.’ I’m like, you have not experienced what time can teach you.”
— Ashley ([07:19])
On progress and going through every step:
“If you want to get from the first floor to the tenth floor, you have to go through the second, third, fourth... You will not be prepared to actually lead on that tenth floor if you haven’t been.”
— Ashley ([14:22])
Skin in the game:
“People who have skin in the game… often give better advice. When you win, we win. Because my whole business is built on you winning with paid advertising.”
— Ashley ([21:17])
Harvard Business Review Study:
Entrepreneurs who align decisions with their business stage are 3.6x more likely to scale successfully ([15:36]).
CB Insights:
42% of startups fail because they build something the market does not want ([16:33]).
Edelman’s Trust Barometer:
65% of people trust peers with direct experience more than influencers ([19:16]).
Entrepreneurship Mentoring Research:
Founders paired with active business owners saw a 27% higher success rate ([22:04]).
Ashley recommends listeners ask themselves these pivotal questions before any investment:
“Ask yourself those five questions and it’s really going to help you as you make investments that can really elevate you and speed things up. I’m grateful I’ve done that in my business, too.” ([23:52])
Ashley previews the coming episodes, which will feature specific rooms she’s invested in—including short-term rental/ad room strategies and what she learned from being in a room with Alex Hormozi.
“Get ready because there’s some good stuff coming on these next few episodes about rooms that we’ve invested in and what we’ve learned. Can’t wait to see you.” ([25:20])
| Timestamp | Segment Description | |------------|----------------------------------------------------------------------| | 00:00 | Welcome, podcast premise, YouTube content highlights | | 03:27 | Introducing the “rooms” & upcoming mini-series | | 05:20 | The four (+1) questions to ask before investing in a room/mastermind | | 10:45 | Championship team analogy—combining experts vs. duplicating roles | | 12:40 | Video content investment as strategic team building | | 14:22 | The necessity of progressing through every business stage | | 15:36 | HBR research: decisions aligned to business stage | | 16:33 | CB Insights: why startups fail | | 17:24 | Value of curated expert rooms vs. choice overload | | 19:16 | Edelman’s Trust Barometer: proof vs. popularity | | 21:17 | “Skin in the game” filter | | 22:04 | Mentoring stat: 27% increase with active business owner mentors | | 23:52 | Recap of five decision-making filters | | 25:20 | Preview of coming episodes |
For listeners serious about accelerating their business through strategic paid advertising, Ashley’s filters provide an essential blueprint for choosing the ‘right’ rooms—and avoiding costly missteps with the wrong ones.