EP 664 – Marketing Field Of Dreams: If You Market, They Will Come With Sky Cassidy

NCS 664 | If You Market


Marketing may seem so simple to think about, but that is not the case in the real world where people are bombarded with so many products anywhere. In this episode, Scott Carson interviews the CEO of MountainTop Data and host of The “If You Market” Podcast, Sky Cassidy. Together, they discuss marketing trends, the need to be creative, and why you have to continue marketing to attract clients. Sky shares how it doesn’t matter how cool or life-changing your product is; if you can’t market it, no one’s buying it. That’s why Sky despises Kevin Costner’s philosophy, “if you build it, they will come,” in the movie “Field Of Dreams” because it’s completely out of touch with reality. If you want to understand how sales and marketing work in the real world, then this episode is for you. Dive in!

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Marketing Field Of Dreams: If You Market, They Will Come With Sky Cassidy

This is Sky Cassidy. In this episode, Scott Carson is talking with me. We are talking about the marketing mindset, B2B marketing, how failure is an option a lot of the time. I give some email tips. We dig into competition and how important that is. We get into marketing stories. We talk about selling stuff. I can’t even remember everything we covered. It’s crazy.

I’m even more jacked up to have somebody who was able to do a little bit of a Vulcan mind-meld with. Somebody who shares and has a similar passion for one of the big things is the key to success for entrepreneurs and business owners out there. If you are an investor or business owner looking to get investing, you have to take that business owner and entrepreneur mindset and realize it’s up to you to make things happen. I’m honored to have the bad-ass, the problem-solver, the thinker, a lover of science, my buddy who is the CEO of MountainTop Data. He is the host of the If You Market Podcast and a professional ping pong color commentary. I’m talking about my buddy, Sky Cassidy, joining us from the West Coast. What is going on? How is it going, Sky?

I got to make a correction because I don’t want people to come after me later. It may say professional somewhere on my profile. I’m an amateur interoffice color commentary. I don’t want to be called out a decade from now saying I was lying on my resume. It’s fully amateur but still a lot of color.

Is that like ESPN’s The Ocho where you have to pay double?

It’s public access network version of ESPN’s The Ocho. I have not commentated in many games since COVID. We used to have interoffice tournaments and we were setting up a local interoffice tournament league that we had all worked out, where we were going to have a bunch of people in a ping pong league. I would get to commentate everybody there. Coronavirus, what are you going to do?

I wanted to be a sports commentator of SportsCenter. I have called a few high school games, even a college game before. That is another thing we got in common. You are the host of the If You Market Podcast. Share with our audience a little about the podcast. I was honored to be a guest on it. We had a great time rifting and talking about marketing and some of the things that we see going on out there.

That is what we do. We rift on the stuff. We try to cover the topics a bit. When you were on, we talked about the marketing mindset, which I love. We have topics sometimes that conflict with each other, but one of my philosophies is that sales own marketing. Marketing works for sales. That said, when you came on our show, the If You Market Podcast, what we were talking about there was the marketing mindset where a business should be thinking about, “Can I market this product?” It’s a lean startup style concept where first you find something you can market and then you have a business. If you can’t market it, it doesn’t matter how cool the product is or how much everybody needs this, or how much it would change their lives. None of that matters.

It’s nuclear power. It may be a great idea but if you can’t market it, people won’t buy it. It doesn’t matter how great it is. Find something you can market. We covered that thoroughly in that episode. You were awesome there, getting people to think in that way. It’s not, “Can I sell it? Can I make it?” The title of our podcast, the If You Market Podcast, comes directly from Kevin Costner, polluting everybody’s minds with this, “If you build it, they will come bullshit.” That movie is so fake, I couldn’t believe it. No way that would happen. It’s so out of touch with reality. The reality version of that is he is a crazy guy who ruins his business to build a baseball field and ends up in a sane asylum and his wife is bankrupt.

I don’t care if he had ghosts come into the field, nobody’s going to show up because they don’t know it exists. You have to market the shit out of it or nobody knows it exists. It doesn’t matter if you have baseball ghosts showing up to your cornfield. You have zero audience unless you market it. That was the general idea. Even if you do market it, nobody’s going to give a crap because they don’t believe you. You are saying you have a baseball ghost showing up. It’s like coming out in the middle of nowhere for some weird guys con. It sounds like a serial killer that ends up buried in his cornfield. It still doesn’t matter. You have to be able to successfully market it and then you have a business.

It’s a movie based on somebody buying the note. The investor is buying the note directly from the bank. They are going to foreclose Ray and his wife. It is a note movie. That is reality a lot of times. It’s funny that you picked that movie because we haven’t talked about that movie but I agree. You are not going to have children of the corn walking out of the cornfields to save you. Millions of people lighten up because you build something. We have all gone to different conferences and workshops. You have people that have a passion project. They are passionate about their product, software, need, but if you can’t market it or you don’t market it, it doesn’t matter how good the tiddlywink is that you are doing. It doesn’t mean anything out there.

There is nothing sadder than the real-life version where someone takes their life savings and risks it all because they listened to some podcasts that told them, “If you love something, you got to jump all the way in and do it. You got to fully commit.” They are fully committing to an empty swimming pool and they are dead. Somebody should have told them like, “That is a stupid idea.” You are going to lose everything. Just because you are passionate about something doesn’t mean you are not going to end up on the streets because of it. You got to be able to pull it off. That doesn’t come purely from a passion. Passion is great. You have got to have all the drive. You got to be out there pushing hard. That can force some things to succeed that may not otherwise but it doesn’t matter if it’s not going to work. Do not do a header into that empty swimming pool.

That is the thing we see because we deal with so many investors that want to get into real estate investing. Many people are used to dealing with, “We are going to deal with foreclosures or people that are losing their house.” They don’t realize that who we are dealing with, you have to stand out from the crowd. You got to look like you are a little bit different than the weekend warriors out there that are jack of all trades because we are dealing with banks, asset managers and professional organizations. There is a whole new level up in your game to get people to want to pay attention to you and want to send you deals or do business with it too.

I’m not too familiar outside of what I know from Field of Dreams with your business.

What I’m getting at is upping that game. When you are B2B versus B2C, it’s a whole different set of rules in making things happen and then standing out from the crowd.

With B2C, your market is even more important because you have to be able to market to so many more people. At least with B2B, most B2B companies when you start out, you’re not even marketing. Your sales is your marketing because you’re going out and you are getting 1 or 2 large clients. It’s so much bigger of a sale. You are not selling a $0.99 candy bar or even a $9.99 candy bar. You have to get massive amounts of sales. You can get away without marketing to some level but once you want to grow and scale, you are going to have to market the shit out of it. If you want to do that, you want to do that head time. You’ve got to look at it and say, “What’s my angle for that?” Once I get past how many people I can call and close in a day, in a month, go visit and close. If I want to grow bigger than that, I have to be able to market this somehow. How am I going to market it to people? Can it be marketed? Will they listen? Are there channels for them to show up?

NCS 664 | If You Market

If You Market: Sales owns marketing. Marketing works for sales.


You have talked and interviewed a ton of people in your podcast. Are there any characteristics or competencies that the successful people that you see and deal with that you can share? Success stories or things that help those that stand out or things that they are good at or not so good at.

I have written everything down and I always have points. Coming on a show like yours, I got some bullet points worked out. I got to be able to remember when to go on. I got my notes here on this. I have a thing that I call the four qualities of competence. I look to improve any of these areas in myself whenever I can. Anytime I’m hiring or working with somebody, even if a partnership, a client or whatever it is, I look to see what they have in these areas because then you know where they are going to let you down. It’s like in sports. You look to see what are somebody’s skills and how can I make sure I’m playing to those skills. If it’s a competitor, how can I make sure I’m going after the weak spots?

What I’ve developed over the years are these four qualities of competence. Those are grit, mindfulness, fairness and intelligence. A couple of them go together. Fairness sounds like this soft, weird, squishy, snowflake thing. I couldn’t come up with a better word for it but it plays well with grit. You can’t be all grit. I have three to start with. I had grit, mindfulness and intelligence. That’s what I look for in people. That’s what I looked to evaluate in them. I came to realize, without having fairness in there, what I would end up finding are sociopaths, which can be great, but not if you are trying to do business with them. There a lot of successful sociopaths but it doesn’t help the people around them necessarily.

That is where fairness comes in. Let’s say you are hiring a salesperson. They got a ton of grit. They are able to look at themselves and see their issues, the mindfulness and make corrections. They are all ego-driven. They are smart enough to do the job. The intelligence part is, are they intelligent enough? You have a salesperson with those qualities, but their fairness is way out of whack. They are using these good qualities they have in other areas to maximize their profits, not your company’s profits, to try to work your commission structure system. You are going to get that person who’s good at sandbagging stuff, manipulating the system and constantly bringing the most out of you instead of doing their best. That is where fairness comes in.

They are going to be the high performing sales rep that is poison in your office. A partnership is the same thing. You will get the partner that seems like this guy’s going to be able to deliver, bust his ass, all these other things are in place. He’s really smart. Are they going to use all that to screw you or do not care once it’s time to drop you at a heartbeat because something else might look better? Do they have some level of fairness where you can trust them to work with them? Those are the four things that I like to evaluate people to keep things simple.

Stuff comes to mind that you want in staff. It’s got to be a win-win truly in business. If it’s just a win for one and somebody else gets screwed or walks away from the closing table thinking they got taken, it’s never a good feeling to be a part of that. If you’re hiring people to represent your vendors or sales staff or people that are out doing outbound phone calls, you want to make sure that they’re 100% committed to what the goals of the business are. It’s not like, “Let me pad my resume. We’re only be making some side deals,” like what most of our politicians are doing. We do have a lot of sociopaths in Washington, DC.

They lack that fairness. They have a lot of other things. Maybe the mindfulness is missing with them frequently too. They bust their ass. They don’t get there by being lazy. They are typically intelligent but not always. Sometimes there’s more ego than mindfulness, and then sometimes the fairness doesn’t even come into the equation. They see everything in life. When I say they, people that have this sociopathic business tendency. Everything in life is a zero-sum game. Everyone else is the other team and they are their team. Whatever they do to win, that is all that matters. It’s like, “If you are not cheating, you are not trying.” There are all these sayings developed, “You have to screw them before they screw you.” Anybody who uses any of those things, I would steer clear off because they are going to stab you in the back as soon as they possibly can.

If I was in a zero-sum game where there is no win-win, I would want to win. A lot of people think that way. They think the whole world is that way. You can never be on their team. They don’t have a team. It is them. When you can identify those people and stay away from them, you can save yourself. These are dangerous people because they will undermine you. You will think they are on your team, and the whole time they are working against you and only for themselves. That is why that fairness is so important. You do not want a super smart and hard-working serial killer on your team. You are in trouble.

We have run into those from time to time, guys that are trading assets in our business. They tell you that you got approved and then come Friday, you spend the weekend getting due diligence stuff done, and come Monday, you dropped a couple of $100 and find out, “I sold it to somebody else.” You’re like, “What?” I can understand that stuff happening once in a while but repeated actions taking place is not a one-off interesting situation. It’s because you are dealing with a sociopath and somebody who’s completely out for themselves. It’s not a good thing.

Maybe it never worked out for you with them but the fact that they don’t care that it ever works out for you, they’re saying, “I don’t care for a long-term relationship. Maybe you’ll never notice that I’m constantly screwing you and you will stick around and be my lapdog.” Identify those people because you do not want to be chasing them all the time when they are never going to come through for you. By accident, if it happens to benefit them once, they’re going to keep you around to use you. In business, that can kill you. Your margins cannot handle that kind of business relationships.

With all the different people you have interviewed and talked with or get on there, what are some of the unique things that you have seen people market that has been successful? Maybe it’s a tactic or a tool or something that you have used that stood out for you?

We’ve had some people with some interesting products. Were you thinking more of the product or the approaches they were taking?

It’s a little bit of both.

I had a call with someone that makes custom motorcycle helmets as works of art, typically to sit in people’s walls, probably in the background in their Zoom video. They will make them for artists. They’ll take their artwork and turn it into a motorcycle helmet. I looked at that and said, “What a unique product?” This is the type of thing that when you’re sitting here saying, “I got a ton of money to blow it. I need to get a gift for this person who has everything.” Every once in a while, you want that product. It’s like, “Let me get some sports memorabilia.” You wish there was a site that was like random stuff that no one has but they would think, ”Cool.” You could go there and find gifts for people who have everything.

That kind of product is always very cool. We’re a B2B marketing podcast, there are a lot of types of businesses that are looking to market to. They’re just trying to figure out how to get in the market. Everybody we talked to on the show has something that they are good at. That is what they are on for. You were on with this marketing mindset and you like drilling into people. Think this way or you ruin yourself trying to make something that’s doomed or at least pivot. There is a lot of businesses too, you just need to pivot. Frequently, maybe there was something that worked and you could market. Where a pivot occurs is when you say, “Our product is no longer marketable. There is this variation of it that’s more marketable now. We are going to shift to that.” That is how we get business, make money, and be successful. It’s great to have a passion project but not if it ends up bankrupting you.

I love that concept because a lot of people will base stuff off of like when you talk about motorcycle helmets, “It’s a cost.” There is some high-end, some medium and some cheap ones that are a plastic nacho bowl that you got at a baseball game that you use as a helmet if you want it to. That whole aspect of the custom artwork, that takes it to a different level of not competing on price or I don’t want to say ego, but it’s a piece of artwork. If somebody is going to spend $20,000 on a motorcycle or even more up to six figures on a custom motorcycle or shop. It’s like me paying $500 for a Dan Marino signed Manny golfer’s helmet or Troy Aikman helmet that I’m a big fan of.

NCS 664 | If You Market

If You Market: It’s great to have a passion project, but not if it ends up bankrupting you.


You can take a piece of memorabilia, have them sign it and have it turned into a helmet. Those kinds of unique products, looking at it exactly and saying, “Do you want to try to manufacture cool motorcycle helmets and get into that market, and compete with everybody else to sell a helmet?” I used to ride motorcycles. I can’t remember. They probably go for $400 nowadays. I can’t even remember what they were when I was riding. Do you want to make something that you’re going to sell for $2,000, $3,000 and you are not competing with anybody? How do I find somebody who’s a lover of Star Wars and would love to have a custom motorcycle helmet with all Star Wars stuff on it? How do I find artists who want to have a motorcycle helmet? How do I find dealerships who want to have their own custom motorcycle helmet? You are in a much more interesting space, something that you can theoretically market. I don’t know enough about that business. She is going to be thrilled that we are talking so much about her.

I have seen some art exhibits where they took a different style of gas cans of different motorcycles and turned that into artwork or they have done things with that where they dip it in and they have got painting so it comes out looking like a snakeskin. They have turned that all into different artwork. We deal with a lot of training aspect of things where people are learning a lot of similar things. We always try to customize it a little bit differently like, what is your goal? What’s the focus of what you are doing?” Trying to cater to those individual needs. I had a great conversation with a couple of guys and gals from Tulsa. They got some bad counsel from somebody else in the industry. I’m like, “You got $12 million raised. You can write your own check. You aren’t got to wait for somebody to feed you. You can go directly to your sources, go directly to the business model. You have a great website. You have experience. Have a little confidence in what you have accomplished. Banks aren’t going to care if you are brand new, besides the fact that you can write a check and make things happen.”

That is where that grit comes in. Don’t give up the first time you do something wrong. We had an episode a while back about expect to fail a lot when you are marketing stuff the first time you do everything. If you try something and it works, be either suspicious or grateful that somehow on the first try you happen to get it right. Marketing is a trial and error. Try this and see if that works. What about this audience? You are rarely so intelligent that you look at the market and turn all the gears and say, “Here is where I need to go. Here’s how it works. This is exactly what is going to get us this return. It happens that way.” It’s not going to happen. You are going to make all your plans.

Don’t spend too much time on it. When you mess up, it’s not even failing but mess up, you will say, “I sent out emails and I didn’t do the auto-fill properly. There are all these blank spots where it was supposed to put in information. I look like an asshole.” You look like an asshole so don’t do it again. Learn from that and do it differently. We all do that. I do posts on social media and on LinkedIn every once in a while but email fails. I’m constantly getting these emails and people did this stupid and that dumb thing or that terrible idea for the email creative. Every once in a while, we will put out one of our own because we screw up too. We are pointing a finger and laughing at everybody else but the point is to point out to people, “Don’t do this.”

Some of them are obvious but some of them are not obvious but common. We all do occasionally. You are going to screw up. You look at professional athletes. Every once in a while, they drop the ball. It happens. They don’t quit when they drop the ball. Keep at it, correct it, work on it and try to screw up less over time. Failure is an option on each individual level. You can try something and it doesn’t work or you can make a mistake and it doesn’t work. You need to adjust it either way though. It’s having that grit to keep going unless you realize it’s a terrible idea and you should have never started.

That is a big thing. You have a lot of people, entrepreneurs start off that they go down with a ship. They have their whole investment in that. They don’t play Frogger and jump onto something else. You see a lot of successful entrepreneurs, they will jump from business to business or venture to venture because they are like, “That was a horrible venture. I’m not going to waste my time and money and drag myself down on this albatross. I’m going to jump over to something successful or take a step back from my what my venture and regroup a little bit, get things back under the track, and then go out again for it.” That is a big part of grit. It’s that ability to take it in the face a couple of times and you keep getting back up and going from there. Many people don’t have that at all. They will send an email blast out once to their audience or to clients and they will never make a phone call or they will avoid the phone. If it didn’t work that time, they’re like, “What?”

“The business didn’t come flowing in after I sent this out, I should quit.” At some point, yes but not until you have tried A through Z, or you know, “This was a terrible idea.” I used to be in the startup community for a while. We were going to all these different startup events. Initially, this company, I only took over in 2016. One of the things that I would see all the time and anybody who has been at communities all the time is people have their idea. They think, “This is my great idea. I want to start a company. Here is what it is.” It’s so great they don’t even want to share it with investors or something, which now you are going nowhere automatically. The advice I would give those people after being in that business for a while and seeing what goes on is if you have your one great idea, think about throwing it away or giving it away and try to have a second one. If you only have one good idea in your life, odds are you don’t have any good ideas. If you can’t come up with more than one good idea, work for someone else and then you can make a living, but you’re not going to have one great epiphany that’s this billion-dollar company and no other good ideas. Unless you have ten great ideas and can’t decide which one to run with, you don’t have any great ideas.

The thing that drives me bonkers is they want everything to be so polished and perfect, “It’s got to be exactly like this.” It doesn’t work that way. You got to get out there and get dirty and banged up and try a few things we have talked about before but run with different ideas. It’s okay to be outside the box. It’s okay to be unique to yourself. It’s even okay to ask for forgiveness a few times versus permission as I like to say sometimes.

Steve Jobs who is known for being a perfectionist learned the hard way early on. You have to shift it. You can’t keep working on the product like, “Let’s tweak this. Look at it.” If you never shift it, you have no business. You don’t even have the opportunity to make it better next time. Click send on that email and then realize you screwed up and you didn’t put your own name in the subject line. You copy and paste someone else’s signature, and then rework it and send it again the next day. Keep adjusting in getting better. It’s okay to make mistakes. It happens.

What is one platform that you are gung-ho on that you use a lot and see a lot of success or a lot of untapped potential with, Sky?

I’m in the B2B space. Our platform, other people are like, “Is that even a platform anymore if they’re on Facebook, Instagram, Clubhouse or whatever school nowadays?” B2B people are all over LinkedIn. That’s where everybody is all the time. That’s where stuff’s done in B2B space. That is where I’m at. That is where everything in our industry and space works. Other platforms are great for other markets and for other things. One of the marketing rules is to go where your audience is. We are B2B so that is where we are going to go. If we start trying to sell our products, business contact, information data, email campaign management and data pending on Facebook, people will say, “Go to LinkedIn and post a picture of kittens or your political views. What are you doing here? This is a business site. I’m sorry, this is a professional site. This is not somewhere for you to put your conspiracy theories. Put something about business, please.” Every channel has its audience and purposes. Most of them are for consumers. LinkedIn is all B2B. That’s where you want to reach out to people for that.

I’m a huge fan of LinkedIn. I spent a lot of time there. It’s been successful for us in finding bankers and funding and developing relationships that have been a win-win across the board and making things happen versus fakebook out there. The Association of Marketing Professionals or AMA, a few years ago, did some studies to see along with the type of people that are hanging out on LinkedIn. Your CEOs, moneymakers, decision-makers are spending time on LinkedIn and then Twitter at the time because they can get their information in and be direct to the source versus scrolling through and having time to waste on Facebook or Instagram, or they’re not popping locking on TikTok or anything like that these days.

If you have a product, you want to promote Roblox to twelve-year-olds, then you got Facebook and that’s what all that stuffs for. LinkedIn is the area to connect with professionals where you want to do business, you want to do B2B stuff. You try to reach out to a banker about some real estate deal on TikTok and see what happens, or try to go promote your real estate stuff on a channel like that, on Instagram. I don’t even have an Instagram account so I shouldn’t speak to it.

It’s not successful.

You are wasting your content efforts. You need to put yourself out there and you need to market the shit out of yourself where the right audience can respond. Kevin Costner wants to market his cornfield of magical ghost baseball players. There’s a certain audience that’s going to respond to that like gullible people who think, “There are ghosts on this baseball field.” You want to find those. If you go to Wall Street and tell them you got this, they aren’t giving you a time of day. You got to market the shit out of it on a platform where the right people are and can possibly be responsive. One of the things we have seen in B2B marketing that people don’t account for sometimes is LinkedIn is great right now for B2B. It’s underutilized. Their ads are expensive but at the same time, they are undervalued.

NCS 664 | If You Market

If You Market: You’re going to screw up. Don’t quit when you drop the ball. Keep at it and work on it.


Facebook was this way several years ago as well. Anytime you can find these channels where your people are there, all the rest of the market audience hasn’t quite caught onto it yet but the audience is there. The auction for the ads and the attention hasn’t taken off because all the other marketers haven’t jumped on it, it’s an undercost platform where you are getting in and they’re desperate for people to pay them to get exposed to this audience so you can get it at pennies on the dollar. You have a secret fishing hole. Our marketers are always looking for that. They are like, “I can go there. All the fish I want are there. Every other person in my space isn’t there.”

You get to the point where this is no longer this small secret fishing hole, it’s this massive pond but it’s so overfished because every marketer is there drag netting it constantly that you’re competing and everything is way over cost. To get access to it, it’s way too expensive. You have got to find that marketing channel that gives you value. These closed places like Google Ad Words, LinkedIn and Facebook own the marketplace. They are attracting people to the party and then they want you to pay to come in. The more popular it is the more they make you pay. Those places are great when they have an audience and when the value is there for you and for your product. You can test them out easily and that is all good, but you don’t own that audience unless you can extract them out of their place somehow.

That is where what we do with email marketing is useful. People building their own email lists, getting people to sign up for our newsletter so you can directly communicate with your audience and not have to go through these other channels. There’s a reason these channels start out as this free open thing. You can come in, build an audience, post and they’ll see it. Eventually, you can post and some of them will see it. You can post and people who follow you, it’ll get to a percentage of them. You can post but unless you pay, nobody’s going to see it. They’re starting out. Everything’s free. Build your audience, get everybody in there, and then once they have it all there, they’re going to start turning down what you can get for free so they can maximize what they can charge for.

The great thing about owning emails is when you have people’s contact information, you know it’s the right audience. Email, at least now, is still this open channel where you can email somebody that costs pretty much nothing. Write up an email and click send to someone. If you want to send larger campaigns, you got to set up something larger. There are rules you got to follow but it is still this free and open channel where you can own your marketing. I love all the individual marketplaces for their use but being able to directly email people. There is a reason you probably don’t communicate with people on Facebook when you are closing a deal. You don’t communicate back and forth. You send an email back and forth because you own that conversation.

It’s not being word categorized by Facebook to figure out what kind of ad to show you next and where to push you and your information sold off somewhere else or what you are talking about. That is your communication with your client and prospects. Email is always my favorite channel. It’s why I’m in the business I’m in. It’s an amazing tool that allows everybody to communicate either individually or at mass and get their products out there. It’s a digital version of the old school sales that made America with door-to-door salespeople, which have a bad reputation now but if you look back at something like Zig Ziglar and people selling pots and pans door-to-door and it sounds corny, if you look back at that back then, those products, you couldn’t go to Walmart and Target and get all this stuff.

It was something that people needed. It drove the economy because people were able to freely go out and move around the country and sell. All these other countries wonder why they can’t do what America does because we always maintain the ability to have open marketplaces. You can go door-to-door and sell your encyclopedias and your pots and pans. You can send emails to people. We have the CAN-SPAM Act, not Europe’s GDPR can’t market to people you don’t know act.

You can’t even have the information of people you don’t know act. You see somebody on the street, better not know their name or they are going to sue you act. You are not allowed to know anything about anybody. Every time you see your local bartender or restaurant server, they have to have scrubbed any memory of you in the past and what your preferences are. Here in America, we want to serve people and find a good balance to allow the business to happen and optimize it. That balance is critical. It’s why I love email. Other platforms are great also for their purpose.

I’m a big fan of email because email still has 400 to 1 at least return on investment for every dollar you are spending on it if you’re using it on a regular basis. That brings to mind the question of how often is too much to send out to your warm contact list? I know that it depends is the answer. Tell us what you think. Tell us what your counsel on this.

Don’t send more than once a week. We get people who want to send every day throughout the week constantly. You are going to piss people off. We get people who are like, “We can’t send more than once a month.” If you send half your audience at least even more that, it isn’t even going to see the email. It’s not even registered. The subject line is not going to interest them. You have to realize that it’s like a TV commercial. You don’t say, “We are going to post it once at this time of day.” You see people do some social media sometimes too. You get the same tweet five days in a row three times a day because nobody is watching constantly and seeing every bit of content. It’s the same with email, even though it comes to the inbox, stuff gets filtered out.

You send the first thing in the morning and they are doing their bulk saying, “I don’t know this.” You do want some regularity that gives you a heightened chance of once a month they are going to see or take one second to look at your subject line. You can’t over send to them. I have companies that I get three emails a day from. This is unsolicited stuff, not a newsletter. What you do when you oversend to people is you either get them to complain, ideally to opt-out from your message is the cleanest thing they could do, or through their internal filter, filters you out. I have certain emails where the format of the email or the name I’m receiving it from, I automatically know when I’m looking at my 200 emails in my inbox in the morning to delete it without even starting to look at the subject line.

A client could send me an email, if they sent it from the wrong name that happens to be one of these names that trigger me, I would delete it. I have deleted emails before because they were in the same format of things that I know I constantly get. Most people would unsubscribe or block. Some people are afraid to unsubscribe because they think, sometimes rightfully so, that by unsubscribing, you are saying to one of these people you are real and then they will email you more. That is what the CAN-SPAM Act is designed to prevent, but it doesn’t mean that there are not bad players out there doing it, so you start deleting or filtering stuff and setting up filters. Mentally filtering is what happens the most though. A lot of companies that overspend don’t realize it because the metrics aren’t going to tell you, but the recipient on the other end has mentally blocked you. Every time you see that newsletter format or that subject line because you have some consistency in your subject line, it allows the people who don’t want to see your message to consistently delete you without having to even look at it.

People need to hear that. It’s not once a month. I was talking to a friend. They were the ones helping to raise capital. I’m like, “How often are you sending an email out to your database to market?” “Once a month.” I’m like, “That is not even enough to be noticed. When are you sending out?” “On a Saturday.” I’m like, “That is the worst day to send an email out trying to connect with things.” Tuesday, Wednesday, Thursday. I like sending out Sunday nights for a Monday night thing because at 7:00 people are looking at their email.

It depends on your creativity. You have to experiment with it. It depends on your product and your audience. Some people, first thing in the morning, get it to them when they have time and they are looking through their emails. Other people are mass deleting everything they don’t immediately recognize first thing in the morning to be out those new emails. You want to send it afternoon when they are chilling with their lunch, or in the evening or on the weekend. Some business emails are way more successful on the weekend. You got to experiment. If you send it out once a month, that is twelve times a year. They may have opened one of those emails. That is once a year they are even seeing your content. It’s going to take you 200 years to get a sale. That doesn’t work well as a business model.

That is why I always say 80% of sales are made on the fifth contact. Once a week, that is a lot faster than 5 to 6 months. I get phone calls from bankers that we have been emailing for years. They haven’t bought anything from them, but they keep getting my emails. I keep opening and reading it and they are like, “Scott, we’ve got something for you. We have got a deal that we worked on with you together.” I’m like, “I have been emailing you for a while.” He’s like, “We keep your green emails.” I’m like, “My green?” He’s like, “Your logos, it branded it into us. I would read it every time, it’s interesting, but we never had anything to do with it until now.” I’m like, “That works for me.”

You will get people. We had a message that was successful for years that we sent every single week to the same group of people in our target audience because it was successful. We knew a new group of people would see it every week. We also knew that many of those people, we had seen opening the email for two years before they replied and said, “We want this.” They had been seeing it and sitting on it the whole time because they knew they were interested just not quite yet. People also think, “If they didn’t respond to the email, then I should remove them from my list.” If they didn’t respond negatively, then you should keep sending it to them. One trick for identifying whether you’re sending too often is to send once a week and start ramping it up. Send twice a week, three times a week. I don’t want to encourage people to oversend.

NCS 664 | If You Market

If You Market: You need to put yourself out there where the right audience can see you and actually respond.


What you will see is you will hit a point pretty quickly where you see the unsubscribes start to go up. It’s like, “I have annoyed these people to the point where they are unsubscribing. That is bad. I have hurt my list but I know never to go that that often again because that’s the level where people that previously got the email and didn’t bother to unsubscribe.” Deleting an email once a week is not a big deal, but having deleted it three times a day, I’m going to go and make the effort to unsubscribe. That metric can help you figure out for your audience how frequent is too frequent.

I heard someone say that if you have emailed daily, you have the lowest unsubscribe rate. I’m a big believer that people start scanning over your stuff, they don’t pay attention to your stuff because they are used to seeing it and it looks the same. They unsubscribed and they are not paying attention anymore.

We have a hibernation practice that we have tried before. It’s hard to tell whether people are seeing your message and interested and sitting on it and knowing you are going to email every week. They are not going to unsubscribe you, but when they are ready, they will respond to that one or if they are annoyed constantly. A practice we did that seem pretty successful and you can vary the amount of time, if you have time and your system is set up to handle it is what we call hibernating, where people don’t have any interaction for a period of time. We dropped them off the list, but for a set period of time, and then we introduced them back. There is a lot of ways you can do it. You can say, “We send out 100,000 emails. These 50,000 people didn’t even open.”

You have to think, okay, “What does that mean? Do we want to drop them off because they didn’t open or do we need to keep them on because they didn’t open? They can’t be annoyed about something they didn’t even open necessarily or maybe they are.” Think about it and dig into it. You can say, “Maybe we are going to take people. If we send once a week for a month and they don’t open any of the emails, we are going to hibernate them for a month or for two months.” In that way, you can try to help prevent them from creating that mental picture of your emails and automatically, it will seem fresh the next time you come around. Take that group of people and send a different creative that looks different to them from a different person and everything to see.

If those jump up, all of a sudden, you say, “Three months in a row, none of these people opened.” We sent a different format and suddenly a bunch of them opened and clicked. We had programmed them to identify and mentally block our creative so maybe we need to vary it. There are a lot of things you can do but that can help figure out what’s going on with some of these unresponsive people, whether they’re pissed, whether they are never seeing your stuff and it’s going to the junk mail or whether there are some good people in there, they mentally blocked you because you have emailed them too frequently. There will always be some people that mentally block you even if you email them once a quarter but you want to reduce that.

You have done some interesting things prior up to where you are at now at MountainTop Data. How has a movie fantasy league, social media security and a dating story aggregator helped you be a better marketer now?

Those are startup fails that taught me that if you try something out, it fails. It helped me build those principles I shared. I’m going to call them the qualities for competence in evaluating people. Some of those startups, I thought, were great ideas, movie fantasy league. I always liked that one. I thought I could have gone somewhere. The rest of the team didn’t stick it out. They didn’t have the grit. They weren’t into it. Not to slander them, some of them had great qualities but they fell apart. Not because it was a bad idea or it wouldn’t work. I thought it was a trickle company where you can put a little effort into it and let it build up. People were interested in it. We created this product. People signed up and we were tweaking how does a fantasy league for movies work?

You have the Oscars, award shows and the release dates and the box office and all the data’s out there. Movie nerds, this could be a pretty cool thing for them. People are interested in sponsoring something like that, but the other parts of the team fell apart. They didn’t want to stick it out. One of these was something got a big quick win or got bored, wanting to move on to other things so it fell apart. It taught me that even if it’s a good idea and it can work, if you don’t have the right team, things can fall apart. Sometimes things are going to fall apart no matter what. That is okay. It’s your ability to go onto something else. With startups, I played around with it like that.

When I see those different things like that in your bio talking about there are stories to be told on those apps with movies or stories or dating a story. How important is incorporating a story or a theme or journey for your business or clients on your email and marketing side?

When you say a story, it triggers two things in me. One, stories are important. People connect with stories mentally. We have seen in emails when people start telling a story and they include two sentences of a story, it tends to suck you in a little bit, “I walked into my boss’s office,” it’s like, “I want to know what happened.” You want to know what happened next. If you can hook people with those first couple of words because they’re like, “Mentally, this is a story. I got to know what happened next. You can’t watch the first half of the movie and not know what happened next.” Stories are awesome. Storytelling is a great way to convey marketing. You can do so much with stories but there is the origin story in marketing.

It is something that has been pissing me off for the last several years because marketers tend to ruin everything because we find a fishing pond that works and we say, “Let’s go get all the fish out of that pond before anybody else can. I can only carry so many fish. Let me poison this pond so my competition can’t get any also.” We ruined shit because we want to win it all and take it all and use it before everyone else does kind of philosophy. “I better take everything and hoard it because I don’t want anyone else to be able to get this. I have to get everything I can, as fast as I can.” The origin story is taking the concept of a company having a purpose or why the company was created or why it exists.

Having that sociopathic element to it where instead of telling people how the company started or why you are doing this business which should be, “Because I want to feed my family or because I want to. I thought it was a good idea and I could make money at it and make a career out of it. I liked doing this. I saw that it was something I could market so I did it. There was an audience. My job is to serve my customers the best I can and make the best product I can.” That is the story that I want companies to have. These days people say, “I’ve got a commodity. I have whatever type of product no different from anybody else’s. My story can be different though.” They make up bullshit stories to trick people.

That is what marketers do all the time. We are always conning people. There is a big difference between sales and a con. There is a big difference between Boiler Room and Pursuit of Happiness. Somebody with grit, busting their ass and finding a way to get it done. The other is a movie about con men not about sales. We tend to go over to the con because it’s easier as much as possible. This origin story thing is a big one of those. Simon Sinek comes out with a why. Have a why, that is great. This is a great concept. Marketers are going to twist it, ruin it, misinterpret it and turn it into, “How can I convince people that I love them so they will buy my product even though I freaking hate them and I just want their money?” It turns into that.

The biggest corporation that is polluting the water somewhere wants to convince everybody that it’s going to show pictures of gentle mountain streams and talk about how much it loves panda bears. All they love is fooling you into thinking they’re not trying to get money. Here is this charity, “We do all this.” In reality, if that charity cost them a dime more than they made from the positive PR, they would fire their CEO for running that campaign that way and put a new one in place that was going to lay everybody off and scorch the Earth and maximize profits.

I’m not naming any names but Glacier Springs Water and then finding that it was coming out of a tap hose.

NCS 664 | If You Market

If You Market: Everything is more fun when people compete and the best thing rises to the top.


Here is the classic story that pisses me off. I and my college dorm mate couldn’t find high-quality water at a good price. We went to the Bavarian Alps and got this water. The water boy, he has this magical water and we drank it. We were like, “It changed our world. We want to bring this to everyone else.” You are like, “You are just filtering tap water and putting it in a thing and slapped it. You don’t even get your own. You came up with a logo, a catchy name and some marketing.” You said, “I can market this and fool people into buying my product.” You are doing it. Your story is bullshit. The problem there is you are going to undermine people that do these things.

You are going to undermine the actual people who have a real story because eventually, we all start mass filtering out things. When enough people con someone in an area, a con and audience scenario, the audience completely shuts off. It’s the reason it’s almost impossible to approach a woman at a bar and talk to her. Her guard is up. When you’re in an industry or marketing in general and marketers take practice and they use it to maximize profits. People are smart. They will eventually figure out what’s happening to them. That approach is dead for everyone even the people who have a purpose. March of Dimes shows up or any other charity, you’re like, “It’s a con. I don’t trust it because I know all these people with all their nice so give me money, buy my product thing. It’s all bullshit. I’m not getting fooled by that again.”

Suddenly, the practice that was good is so ruined by marketers that you can’t use it anymore. It happens to whole industries. It happens individual marketing practices. It’s why this particular thing that’s caught on pisses me off. It also stifles innovation. These companies say, “I don’t have to make a better product and come up with anything new. I can just find a new way to trick people to buy it. Why would I innovate to compete? Why would I produce a better product for my users when instead I can find out better ways to trick them into buying my product instead of somebody else’s?” I love an open marketplace, capitalism in a marketplace where competition makes things better.

Forget the words open marketplace and capitalism, let’s have baggage. Competition makes everything better. When people find these loopholes where they can hijack the competition, the end product is worse. Imagine one basketball team always got the best players and always was going to win the game. You got the Harlem Globetrotters, that would not be a fun league to watch. You are not going to have the NBA if one team always wins, you need parody. In business, we need parody. These little things people are doing to find loopholes to win when they shouldn’t. The more we can get rid of those, the better product everyone gets at the end, which is what we want in sports and life. Everything is more fun when people compete and the best thing rises to the top.

That is the perfect thing. A lot of people will stop doing things because they have been burnt before versus realizing you have to go out and tell your story. People these days don’t want to be sold. They want to understand and identify. Most people can smell bullshit when you are telling them a lie. They can sense it a million miles away these days. Sky, what is the best place or best way for people to connect with you? Is it on your LinkedIn profile or your website? What is the best way for people to follow what you’re doing and stay in touch?

Check me out on LinkedIn. Check out my company, MountainTop Data if you need the business contact information for your sales and marketing. We have some great tools on there to be able to log on and grab lists directly down from our site quick and easy. I had a promo code for this. We have a tool. You can sign up for a free tool. I use a lot of the word free here. This was an email. It would get thrown in the spam folder. Check out the If You Market Podcast, talking about B2B marketing strictly. If you are down for that, great. If it bores the hell out of you, go to the top data search website.

Guys, you have learned a lot. Sky shared some great nuggets on there and his experience. This is what he does. That is one of the things we want to have him on. If you build it, they won’t come. If you market it, you might get a few ghosts that show up in the cornfields or people showing up wandering around if they know where to go. Go out and take some action. Once again, thanks, Sky. We’ll see you all at the top. Bye.

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About Sky Cassidy

NCS 664 | If You Market

Sky Cassidy is a problem solver, tinkerer and lover of science. He grew up in rural Northern California then studied Photography in Sydney Australia before returning to California where he graduated from Sonoma State in 2000 with a degree in studio arts. He was a founding partner in multiple startups; an event branding site, a photo-sharing app, a dating story aggregator, a movie fantasy league, social media security, and more. After over a decade working in marketing and bouncing around the Southern California startup scene, he settled in as CEO of MountainTop Data, a provider of marketing database services for B2B companies.


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