Engaging Speaking with Jay Mays

INJ 36 | Engaging Speaking


Jay Mays is a twenty-year sales veteran and stand-up comedy producer. From his underdog beginnings in dive bars to being awarded Best Comedy Venue in Miami, Jay has produced live comedy events for some of the biggest names in entertainment including Viacom, Soho House, and Live Nation. As co-founder of Pitch Lab, Jay combines the seemingly disparate worlds of sales and comedy to help professionals be more confident, engaging speakers.

Listen to Episode #36 here

Engaging Speaking with Jay Mays

Our guest is Jay Mays. Jay is a twenty-year sales veteran, a comedy producer, and a recovering standup. He has produced live comedy events for some of the biggest names in entertainment including Viacom, Soho House, and Live Nation. Jay is a Co-founder of Pitch Lab, which combines lessons from sales and comedy to help professionals be more confident and engaging speakers. Welcome, Jay.

Thanks, Pete. I appreciate you having me.

This is unfair because I know you’ve done your homework. If you weren’t working in sales and comedy, what would you be doing?

I’d probably be a waiter serving tables. Is it a server?

You’re a server if it’s TGI Fridays, but if you’re a professional, you’re a waiter or wait staff.

I had a run right out of college. It was about $50 a person type restaurant and I had it down to a science where I enjoyed it. I had jokes. My secret technique to get a 20% tip every time is when I presented the bill. I would also present my hand palm up and shake their hand as I’m handing them the thing like, “Thanks a lot for coming in.” When I shook the hand, guaranteed I always got 20%. It was something about touching or that connection like, “I’m a human being.”

What were your go-to jokes?

Anytime someone said there’s a crack in the glass, I would say, “I’ll be right back with a straw.” The other famous one I would do is if they ask because we’d have bread with pats of butter, they said, “We need more butter.” I’d put one butter pat in my hand, the other butter pat I’d put on a plate behind my hand, and I’d say, “Here’s your butter.” To hand them a pat of butter with my hand is gross and then they’d look at it weird, and then I’d pull the plate out from behind, “Just kidding.”

That would get a big laugh?

Yes. Did you see Demetri Martin’s new one on Netflix?

I haven’t seen it. Netflix is pushing that one on me hardcore, but I haven’t watched it.

I like him. He’s a cleaner, more assessable Ben Kronberg with his one-liners.

That’s super funny to me, I’m not sure that would be funny to anyone else because I know Ben and you work with Ben.

Ben’s one of my favorite comedians but he’s not always assessable to the mainstream. Demetri Martin has a joke at the end of that special about a waiter touching food. I was like, “I’ve used that joke for years. It’s my joke.”

You’d be a good professional server. There has to be more to it than just the fact that you’d be good at it.

Everyone on the planet should wait tables at one point or another. Have you ever noticed when you sat down with someone in a meeting for the first time and you’re at a restaurant? You can tell a lot about that person by how they treat the person taking care of you. Have you ever noticed you could tell a lot about a person by how dismissive they are or if they’re rude or if they’re welcoming or taking a second to thank you? That background or foundation in waiting tables, knowing that each customer that sits down is your boss temporarily and how you’re going to get paid, that provided a fantastic foundation for sales in a lot of ways. I enjoyed the quick connections, getting to know someone on a small level, taking care of someone, and then that validation. Looking for validation has fueled me for many years in sales. It fueled me as a comedian, “I’ve got to get to this first laugh, I got the first laugh. I feel better.” You’re almost always looking for some type of feedback and you get it in serving, you get it in sales, you get it in comedy. As I get older, I try to not need that as much as a human being, this validation to give me my self-worth. Those things when I look backward have driven me in whatever it was I was doing.

I’ve done service-related work but I’ve never waited tables. In some ways, it’s a little peculiar that I didn’t because I have worked hard to put myself through college. It probably would have been a more lucrative path.

There is a beautiful upside at times in being a server.

INJ 36 | Engaging Speaking
Engaging Speaking: You can tell a lot about that person by how they treat others.


It’s a hard work but if you’re good and you get the right job, you can make some money. I have this saying, “Be a professional.” I use it all the time. I use it with myself and I use it with my students. There is something about approaching a job whether as a teacher or as a salesperson. You have this in spades. This idea when you up the level of professionalism associated with work, it can become a craft. There’s something about turning work into a craft that suddenly can make the work intrinsically rewarding. It’s not just the 20% tip that feels good, but that idea like, “I did a nice job and I was creative. I solved problems. I found the new way to do this that makes both my life better and my customers’ lives better.”

I worry about being that person who’s a jerk to a server who has a hard job, yet to me, this is an exchange. I tip incredibly well. I feel when something is not right, I need to say something about it in part because I want it to be right from my experience and my guest’s experience. I know the restaurateur for who owns the place wants it to be right. I don’t always know a good way to do it. How do you get the tone right? When do you do it? Do you do it in private? These kinds of things, especially for places I’m a regular at. What is your advice for me and for anyone else who cares about that idea?

Even though I’m bringing you water and your food and bread, it’s acknowledging that no matter what, we are still two human beings. That could be done as simple as an eye contact and acknowledgment. Even if you and I were talking and the server came, “Thanks.” It’s the ignoring or you’re not even a human being. If you want to be a customer, it’s just an acknowledgment that there’s another human being here. When we all stand up and walk out of this restaurant, we’re three human beings. To be treated like that and not to put them in some old medieval role of servant or a robot could have brought me that water. That’s what I would say is at the heart of what it is.

I ask this question because I believe that customers have a responsibility for a level of professionalism and for a level of decorum. When someone is struggling with a customer, one of my first questions is, “Can you fire that customer? Would it be okay?” If the answer is no, that leads you down a certain path for problem-solving. If the answer is yes, it leads you down another path for problem-solving. It doesn’t mean because you can fire them, you should. As a customer, you should behave yourself. It’s an interesting puzzle.

Early in my career when I was successful at organizations, people would say, “What are you doing differently?” In my mind, I wasn’t doing anything but basic blocking and tackling, following up and being a man of my word. What some would call professionalism is basic. When you say you’re going to do something, do it. Make sure you follow up. Make sure you’re polite. When you say you take that professionalism to another level where it’s a craft, it reminded me of the documentary, Jiro Dreams of Sushi. It affected me in a profound way and that’s what I was thinking of, the massaging of the eel for eight hours and like, “This is beyond sushi.” He says you’ve got to be an apprentice for ten years before you could do anything but massage eels and make rice.

My favorite thing is the most recently hired, their first job is to prepare the hot towels. You have this steaming hot towel. It’s painful and you have to squeeze it. If you don’t squeeze it enough, then it’s too damp. If you squeeze it too much then it’s too dry. It has to be perfect. They won’t even let you touch the food for a decade until you can squeeze the towel perfectly. That’s that craftsperson mindset.

I love the story about how he didn’t want to scale. There are ten seats and that’s it. I forget which one but nowadays, the mentality is more and more, “Let’s scale even if it hurts our quality, even if it hurts our overall business. We’ve got to scale.” To see someone say, “I’m fine. I’m not going to scale. I’m not going to grow it but I’m going to make it better and better.” In the end, to tie it into also by the way the stuff going on in the ocean, we don’t even have the right amount of great premium seafood coming in to scale. How he tied it all together I thought was a great documentary.

[bctt tweet=”You’re not making money while you sleep.” username=””]

The thing that I also liked about it is that Jiro, though a master of his craft is still a flawed human, a less than great dad in some ways. It gives you a greater appreciation for sushi. This has come up a couple of times in the pod before.

How about the King Of Kong? I’m kidding. I want to talk about great documentaries if that’s okay.

You’ve already alluded to my next question. I have new questions. You talked about Jiro’s reluctance to scale. This is applicable to you because you have a new business. One, we’ve talked about scaling and not. You have a business where you’re not selling digital copies of things. You’re not making money while you sleep. I’ll try to describe this and then you can punch it up. One of the products that Jay has is he will show up at your place of business, at your company, at your school. He’ll bring along a comic and do a presentation/workshop around presentation skills. He’s providing insights from the world of standup comedy, in particular, and other forms of comedy improv and so on to help people deal with this thing that is incredibly challenging and fear-inducing. You’ve done this with my MBAs prior to their marketing pitch. What are you saying no to these days and why are you saying no if you are?

I’ve needed someone to talk about this with. At the beginning of Pitch Lab, I thought I had this amazing unique idea and I was out to prove that it was valuable and that I could do it.

How did you get the idea?

My background is I’m a twenty-year sales guy and then I am a seven-year standup comedian way back in ‘05. I don’t want to brag but I was one of the biggest names in Denver unpaid comedy. If there was a free mic, I was there. I was either running it or at the mic. No, I was never great. I’ve talked about this at other points but I had an inauthentic persona doing comedy, where I was out saying things that were blue or dirty or misogynistic or whatever because it was getting laughs. The great comedians were authentic. I was never able to connect like that. There came a time in my life where I was like, “I’m not doing it right. I’m not proud of it.” I married my wife. I had a daughter. All of a sudden, telling these dirty jokes at midnight in a dive bar is not that funny anymore. Right around the time I turned 40, I looked back and said, “I’m a sales guy and I’m a standup comedian and a comedy producer. What does the intersection of this look like? What is the intersection of all that?” My first iteration of the idea was I’m going to start an open mic for salespeople. That’s it. The idea was I was going to run an open mic where comedians did not come, salespeople came and they practiced their pitch.

What I like about this is it’s a nice example of what eventually might be a good idea that the first thought is not the right thought.

Your presentation I saw, it’s Learning Business Principles From Comedy. That was inspiring. The first thought, the second thought, the third thought. I don’t ever want to stop iterating on it. Number one was an open mic for entrepreneurs and salespeople. The next thought was let’s do fake pitches and have improv performers, standup comedians and storytellers give you feedback. The third thought was, “Why don’t I grab some of these comedians and myself and let’s build an interactive workshop where I’m giving them a lot more information, a lot more value, and then let’s pepper in some exercises?” When you talk about scaling and what do I not want to do, I believe that the Pitch Lab experience is in that room. That little piece of fire you get when you give a great talk and you’re done and you feel great, or a great comedy set and they laughed and it’s like, “That was awesome.”

All these different things where you can do a sales pitch, a comedy set and you get off. That feeling of being alive is what I’m trying to recreate inside a Pitch Lab by way of comedy karaoke, by way of improv comedy exercises, by way of pitching fake things. It’s not the full experience but it’s the start of an experience to say, “Here’s what your favorite comedians are doing on stage. Here are the techniques you could use in the workplace, in your next pitch, in your next talk. Let’s practice a little, get a little taste of it. To me, that’s something that needs to be happening in a room together live, that human connection more than, “Here is a video to watch on YouTube about it.” I feel I haven’t found the way to make that scalable. What am I saying no to? I’m finally through the imposter syndrome. Not every workshop is amazing. Not every single person’s life is changed, but we have something here. I’m less trying to, “Let me get out wherever I am. How do I be more strategic? How do I make sure this Pitch Lab is helping me grow my business or getting some type of money to pay for the comedian to pay for the time?” We’re getting there. It’s the process of, “I can’t keep doing it to spin my wheels to prove it to myself because I’ve proved it to myself. I don’t want to keep spending energy on things that aren’t moving us forward.”

I’ve come across Pitch Lab. You invited me to one.

I was a fan. I knew you from Twitter and I followed you. I checked out your book and I was like, “This guy’s in Boulder. This is fantastic.”

This guy’s not supposed to be in Boulder, he’s supposed to be in some other place but he happens to be in Boulder.

After this, I want to ask you about the book and how that changed your career trajectory because that’s another thing I’ve been thinking about.


Jay, remember this is my podcast.

You’re interesting. Do we talk about you on this podcast enough? Ben Kronberg did something like, “Throwing a Frisbee is the ultimate throwing shade.”

I know that tweet. I love that tweet.

You said that and I was reading that, and I was like, “The guy in Boulder that I want to meet knows Ben Kronberg and Ben Kronberg is our guest coach.” I believe I wrote to you on Twitter. What did I call you? What’s your formal title?

Professor of Marketing and Psychology.

There was a fancier word, “Whatever the fancy acumen word named Peter, get in free,” is what I tweeted at you. You had your name. I called you out on Twitter and then you checked it out. I believe you missed the first one. We got you on the second Ben Kronberg one and then we went from there. That was light. I didn’t do a lot of stalking but that was Twitter-based viewing. Sometimes when you have your eye on something, it lines up so I decided to throw it out there.

I’m glad you did and I’m sure I would have stumbled on it eventually given my interest. You’re not doing that anymore. You’ve got some space at an accelerator or something like that or shared co-working space. You put out a call. People paid $30. One of my former students happened to be there. You had 25 people or so show up. I call this battle testing. People are willing to turn over their money and their time for this thing that’s not exactly clear. It suggests that they have a real problem. Too many businesses don’t solve problems. You’re not doing those anymore. Is that right?

I still am.

That seems like a no to me because it was a good way to work it out while using it as funnel marketing.

The concept I want to talk about is too many entrepreneurs I see nowadays are like, “I got my pencil sharpened, I have a perfect website, I have a proposal but I’m not going to do anything until someone hires me.” By going and introducing I to a co-working space like Galvanize, like The Commons. I’m going to put it out. I’m going to invite as many people as I can. I didn’t need permission to start. It was essential, it was totally necessary for me to get started like, “I don’t need your permission. I don’t need you to validate me and pay me. I’m going to go set this up and even if three people are in the room, it’s real.”

It is the epitome of the Lean methodology, which I like a lot. I’ve been working out all these lessons. Comedians have the perfect Lean model. That is that they fail all the time, but their failures have almost no negative effects on them. They fail at the joke level in front of apathetic or sympathetic audiences. They never fail at the joke level for a special. They use this methodology. To me, I saw the Pitch Lab at the co-working spaces. The good news is you’re never going to fail like a joke is going to fail. Some aspects of that event were stronger than others and you learned from it and you iterate.

Your feedback to me about authenticity, I had punched up that entire section. I have read books on it. Your authenticity section isn’t as clear as it could be, and I’ve done a lot. You would be proud.

[bctt tweet=”Nothing takes the soul and the heart away from a salesperson than being handed a budget they didn’t agree on.” username=””]

If I remember correctly, it felt a little theoretical. It felt a little vague.

I’ve done a lot of great things. One more thing about what I learned as my time as a standup comedian about failure, great standup comedians or at least smart ones, I learned quickly the concept of bookending. If I’m going to try new material, I’m still going to start with something super strong. I’m still going to close with something proven that’s super strong. Even when I’m going to try new material, I’m going to bookend it between something. I’m going to get a laugh because I’ve gotten a laugh 4,000 times. I know this is going to work. I’ll try this, and if this doesn’t work and even if it’s a bomb, I got something behind it that I know. I still do that in Pitch Lab. If I have new modules, I’m going to put it right in the middle where it’s nice and cushy. I love what you said about being able to fail, being able to do it. When you’re first starting out in comedy, you can’t bookend with much. Over time you’re going to see the great comedians not necessarily start off with new stuff. Certain comedians are going to do it, but it made me feel safer and more willing to take those risks.

What we know about Pitch Lab is that your audience are people who need some help with presentation skills. You have the sales background. You have this comedy background. You bring this funny person up who also has a comedy background. You have lessons and then you have exercises. You have that feedback mechanism built into this. One of the things is you have comedy karaoke. In that one, you give people jokes or you give them a choice of jokes. They get to choose a joke and then they get up and perform someone else’s joke as you would perform someone else’s song at a karaoke club. You do that as a warm-up.

It’s a fantastic icebreaker. More importantly, it leads directly to stage fright. When I get five or six people from the audience and all of a sudden, “I just came here to learn something and now I’m standing in front of a room.” You’re getting that physiological reaction, and then I can go right into stage fright. When you’re doing music karaoke, sing someone else’s song. When you do comedy karaoke, I have one-liners from Steven Wright, Demetri Martin, Mitch Hedberg and Rita Rudner who’s got some great ones. I tried to do Ben Kronberg but nothing was clean or assessable.

There are only three people in the world laughing at that joke, and two of them are in this room and the other one’s Ben. I like what you’re doing. What you’re saying no to sound like a more figurative no. You’re not turning down work at this point. You’re not in a place where you have that luxury.

I got bills to pay. I’m scrappy. Unless it’s totally outside my wheelhouse, I do refer some storytelling to Pitch Lab. Things that I know are truly outside, but no. I’m not going to turn down anything paid. What I do put my energy into for free, for the top of the funnel, for marketing, that’s changing and that’s changing almost on a daily basis. The other piece is I would love to ask your advice. Do you feel differently about a free Pitch Lab versus paying $30 for a Pitch Lab? Do I have a better chance of continuing the relationship on a $30 Pitch Lab than a free Pitch Lab? I’m in my own head with it, but what is the best way to create a funnel? When there’s a perceived value of $30 but only twenty people show up, or a free one when there are 100 people in the room but they don’t feel they paid anything for it?

It’s a tough decision. To me, you’re the sales guy and I’m the marketing professor. You have real experience.

You have better experience.

To me, the work should be done is not a numbers game, it’s a qualification game. It’s not just who the customer who’s interested in, but what is the value of that customer? I can’t help myself but I like to think about other people’s problems, then I don’t have to think about my own. I was giving this some thought. What I like about Pitch Lab is its fun. It’s differentiated. It solves a real problem, and I probably should start with that one. The next level for Pitch lab is specialization. It’s Pitch Lab for X.

When I first started Pitch Lab, I thought for sure it was going to be all dudes that were either budding entrepreneurs or salespeople. It’s very similar to comedy, mostly guys, salespeople, entrepreneurs.

These engineers who want to have a company but they know that they need to be able to present like Steve Jobs.

Not even them. I was expecting people that it’s already their trade that wanted to ratchet up their skill set. When I started casting the net out like, “Here’s a free show. Here’s a $30 show. Come one, come all.” I skewed 60% female and I skewed account managers, tech guys and gals that are up giving Sprint demos or want to be their own entrepreneurs one day. What amazed me is I started out more specialized and then opened it up because of what I saw. I was like, “This is a real thing. There are people in their mid-30s that never thought that they would ever get into sales that are now a subject matter expert riding along on a client pitch,” or, “I’m in middle management. I have a team of seven and I don’t even want to stand up in front of them in my own conference room.” When I started seeing that, I was like, “We’re onto something,” but I’ve shied away from specializing. I still love working with entrepreneurs. I still love working with sales people because that’s what’s in my heart. To see that many people say, “I want to be more engaging. I want to make sure that my employees or my clients are paying attention to me and not their phones.” It threw me off. I agree with you, but when the data came back it hurt me.

INJ 36 | Engaging Speaking
Engaging Speaking: When everyone has made an individual choice to be inside that room,  engagement is high.


To me, the issue of specialization is the segmentation question. The issue is what are the segments that have the need and believe that you are the right solution?

It’s not picking one. It’s making sure I’m segmented.

At some point, here’s the other idea, the free consulting ends.

I was going to say, “Are you going to send me an invoice for this?”

I talk about this in my MBA class all the time is if you have a B2C idea, make it a B2B idea. The idea is what organizations see this as a need? They have deeper pockets, it’s easier to sell it, and you can sell it to them over and over again. The B2B play for Pitch Lab is where you quit your day job.

I agree and that’s in my mind, which I haven’t figured out how to turn it into reality. B2C is top of the funnel. They go back to HR, their boss. It becomes a B2B lead. By continuing to do these public events, that’s my funnel for B2B. I haven’t cracked that.

There are some people who might not know what B2B and B2C are. B2C is business to consumer, that’s like Coca-Cola selling to you. B2B is business to business, that’s like Coca-Cola selling to GE or vice versa.

I’m a B2B guy at heart, so that’s where I’m most comfortable as a salesperson. What I wanted to say are the attendees of the workshop, when it’s a public event, everyone has made an individual choice to be inside that room and my engagement is high. I don’t have to work hard. They’re with me. I came here, I made this decision. When it’s B2B and one person in HR, the CEO or the head of sales says, “I want my team of twenty people in this room. They’re dragging their feet, “This is stupid. What am I doing here?”
When it’s been imposed on you to come to a Pitch Lab, I have to work three times as hard upfront to win them over, show them value. Most of the time I do but in the end I’m like, “I’m exhausted. That was really hard, an uphill battle to get everybody.” I would still take a B2B.

It’s because it pays the bills better.

I’ll be straight with you, and any comedy producer or promoter can tell you it wears on you to try to have to fill up the show after show on an individual one on one. It’s tiring me out. You’ve got Meetup. You’ve got Eventbrite. You’ve got Twitter. You’ve got Facebook. There are a lot of avenues. It’s not cheap. It’s not easy. Your list gets fatigued pretty quick and it becomes exhausting. At this point, I’m opening up too much here. I need to throttle back.

I understand, I hate promoting. I want to create products. I don’t want to promote them.

How about your game show? Did you pay for the room? Was it easy?

In Boulder, I can fill the room. I did one in LA and it was hard. There’s so much competition for entertainment in that town. One last question, then I promise we’re moving on. This is about promotion and it’s about that idea of people going back. When someone leaves a Pitch Lab, do they have something in their hand?

[bctt tweet=”There are basically two types of people in the work world: those who aren’t working enough and those who are working too much.” username=””]

It’s not as fancy as yours, but I do have a digital PDF with takeaways. It’s bullet points going through stage fright, best practices, voice, presence. I liked what you did, I kept it. I was like, “That is a good idea.” I never ask people to write anything down. Nancy Norton, who has also a fantastic podcast on your show, she gave me an awesome idea that I’m doing too many comedy karaoke lines on the same paper. I should do one comedy karaoke line on the paper and then on the back should be like what yours is. That was Nancy’s idea. I was like, “That’s good, Nancy,” and then I never did it because I had 1,000 things to do. I should and I was impressed with yours but no, that’s one thing I want to do and Nancy’s idea makes perfect sense. Thanks, Nancy.

She’s great. I have all these new questions. I’m afraid that you are going to answer this question with Pitch Lab, so I’m not going to let you answer with Pitch Lab. I want you to tell me about a time that you sought a bigger opportunity, either literally or figuratively. You’re living your life and you go, “There can be more. I can do more. I can do this different,” something where you went and reached and stretched for a bigger opportunity.

I’m not going to use Pitch Lab, so it’s going to be close. We talked about this last time we were hanging out after your last workshop. The last full-time job I had, I was four years as a VP of Business Development at a digital agency, a professional services company. In four years, I had five different bosses. I was never looked at as like, “I’m the guy.” I learned a lot from the last boss. I liked him a lot, but I said, “This is it. I’m done.” Do you remember a point in your life when you were growing up and you lived with your friends a lot because you were out of school, out of the dorms? There was a certain point in your life like, “I cannot live with a roommate anymore. I need my own place. We’re done.” Something snapped like that in my professional career where I said, “I cannot listen to someone else tell me how to do this at 40.”

It was an expensive agency. We had a sophisticated approach. The guys were at $200 an hour. You had to be a $100 million, $500 million and $1 billion company to see value from us. I said, “There are many smaller opportunities where I know I can provide value. I know I can do this.” I jumped for, “I’m done and I’m spun out.” That was the genesis of me being a sales consultant that helps growth stage companies and startups have a sales approach that’s predictable, repeatable and scalable. That was the larger opportunity to say, “If I don’t jump now, and I’m never going to jump. I’m going to be a sales guy working for a budget and commission for the rest of my life.”

This world of sales is fascinating. You have your goals for the year and it’s carrots and sticks world. The best salespeople don’t have to worry about that as much, but it probably still.

Here’s my philosophy on that. When you’re a CEO and you say, “I want to make $20 million in sales this year, so I’m going to hire five salespeople and each of you gets a $4 million budget. Go sell.” That makes no sense. It has to be based on a funnel. It has to be based on how many impressions can we get. What marketing can we do? What will convert into first meetings? Some type of funnel has to take place. I’m not saying a salesperson doesn’t have the onus to fill up their own funnel, but you cannot give a great salesperson 100% of the onus to find 100% of their leads and expect them to magically hit goals. There has to be some type of gravitational pull from the organization, from the marketing system, some type of inbound leads to also compliment that to say, “We can get to $20 million based on the leads we have coming in, based on this and that,” not, “I’m going to divvy it up and this is the number and go at it.” Nothing takes the soul and the heart away from a salesperson than being handed a budget they didn’t agree on, there’s no data attached and they didn’t mutually agree on it. That’s how important that is, but you need to mutually agree upon it and you need to see how you’re going to get there.

What you described is the famous scene with Alec Baldwin from Glengarry Glen Ross where you’re the guys who are saying, “The leads are weak,” and he’s screaming at them, “Be closer.”

That belongs in the ‘80s. That mentality of sales is dead. If people are still alive and selling it, they don’t have any employee retention, they don’t have any good client retention.

The best salespeople are going to leave.

It’s fun to look at a meme. It’s fun to joke around about it. It’s fun to slap your friend’s coffee out of his hand and say, “Hey.” In my honest opinion, it does not exist anymore. It’s 100% dead.

You as a sales consultant, are you focused on helping get the systems in place?

INJ 36 | Engaging Speaking
Engaging Speaking: If you can’t find one salesperson to do what you do, you need to turn to team sales.


I am at the bottom of the funnel. If you’re looking at the full funnel, the top of the funnel is marketing and the bottom of the funnel is sales. I specialize in not the inbound and the outbound, not filling up the top of the funnel. Once one of those people said, “I’ve read the blogs. I’ve downloaded the white papers. I’ve gotten a cold call. I have a need. Let’s talk.” It gets handed over, first discovery. Second discovery, what goes in the pitch? What happens internally, especially in professional services with custom bids, custom investment estimates? Once you’ve pitched, how do you move to contract and how do you close it? Those bottom half not only do I talk and help clients set up the approach which is a value-based approach with a discovery framework. Making sure you’re asking the right questions upfront, but what’s the sales process to get through. I also believe in the specialization of roles, which comes back to Pitch Lab and authenticity. This is another one of my authenticity things.

When I coach a sales person and he or she is talking about the technology they don’t understand. They’ve got a bunch of ums and uhs, their body language is horrible, and everything is awful. I say, “Stop. Tell me a story about your favorite slice of pizza. Tell me a story about your favorite childhood memory. Tell me a story the last time your dog made you laugh.” All of a sudden, the body language is there. The ums and uhs are gone. If you take this concept of authenticity, make sure the salesperson understands the business, business acumen and understands how to make a connection, and understands how to move them through the sales process. Give me a subject matter expert that can talk about the case studies, that could talk about the technology. You turn it into a team sale, so everybody’s authentic. The smart SME, the tech guy, isn’t responsible for, “The next step is a concept.”

They say, “Let me turn this over to Jane, she’ll take care of this.”

The smart guy comes in, demonstrates the value and talks authentically because they’re in it every day. The salesperson is like, “This is my team. They’re talking to it,” and then the salesperson can be what their best at and a lot of my CEOs don’t understand that. My CEO in a small startup to growth stage company, they have it all. They’re charismatic. They intuitively know how to sell. They have an intimate understanding of the product. They’re able to kill it. “I want to stop selling. I can’t find a salesperson.” You can’t find a salesperson to do what you do. It needs to turn into a team sale. That sounds simple. That’s complicated.

That becomes hard to do because now you have people when they have to work together.

Are they billable? Are they not billable? Who do you use when?

You’re getting up early in the morning these days.

5:30 is when my alarm goes off.

Are you hitting snooze?

Sometimes. I am not going to lie on this show. Some days, the night before I’m like, “Forget it,” and I’ll sleep in until 6:30. I know when my body is like, “We’re done,” especially when I’m doing a lot of workshops at night. I did one Tuesday night, one Thursday night. I got some good wind of myself. I was excited about this, so I still woke up early. I owe my body some time to catch up.

I’m having so many different insights and part of the notion is this idea that there are few one-size-fits-all lessons or pieces of advice. This get up early in the morning thing, you listen to these Navy SEALs turned consultants, you should be getting up at 4:30 in the morning. I’m an early riser. This has come up in a previous pod with my buddy, Darwyn Metzger. He’s a late-night person. He’s an owl and I’m a lark, which makes it a little bit difficult for us to be friends because it feels we’re only awake for the same time for eight hours a day. When I was in Australia and he was at home, we were at the perfect time schedule because we’d both be up at exactly the same times. One is that when you should be doing things. I generally believe early in the day you should be doing your most important work. You should be doing the work that requires thinking, creativity, problem-solving and so on before you lose steam, then you transition into shallower work and to more pleasant fun things to do. You end your day on a high note rather than on a work note thing.

Do you exercise in the morning or later in the day usually?

I try to exercise before a meal. Either I’ll exercise at 10:30, 11:00. If you’re going to exercise at 10:30, I’m up at 6:00 and working so I’ve already put a half day in. If I’m exercising at 4:00, 4:30, those are the ideal times for me. I use the late morning one to break up the day and to refresh myself. I like the 4:00, 4:30 one because if I’m up and working at 6:00, I’ve gotten good work done and that becomes a reward. I’m a weirdo. I like working out and so it becomes a reward, and then it transitions into dinner and then it transitions into fun or lighter creative work, reading, and so on. This idea of you hitting your snooze button is an interesting one.

The Navy SEALs are like, “You wimp, you’re never going to be successful,” but I don’t believe that. If you think about it, there are basically two types of people in the work world. There are the people who aren’t working enough and the people who are working too much. Depending on whether you work too much or you don’t work enough, then the advice is different. There’s all this advice about like, “Be lazy and go for walks and all this stuff.” If you work a lot, if you’re overworking, then you need to take a nap and hit the snooze button a little bit. Take care of your body and your soul and your mind.

[bctt tweet=”We all have willpower problems; it’s the people who are good at it that have found a way to find joy in their work.” username=””]

That’s for you, Elon Musk, if you’re reading.

You are going to be less effective. You’re going to enjoy the work less. You’re going to be less creative. You’re going to get stuff done still but you’re not a machine. We all have willpower problems. It’s the people who are good at it that has found a way to find joy in the work and create habits that make it natural. You have to build habits to help give yourself a break. For a lot of people, it’s like, “It’s called work for a reason.” Those folks don’t need the, “Be lazy, take long walks.” They need the, “You need to get up, get on a schedule and make this practice that becomes regular enough that then you can accomplish the things.” Work should serve you in the sense that it provides you resources to live a safe, secure life. The ideal way should be something that doesn’t feel like work. That is something like the server who can find a way to make their shift challenging enough. That the time goes by quickly and that they feel a sense of satisfaction like, “I did a good job and I exercised some muscles besides my biceps carrying trays.”

To me, when you say it’s news because I know you and I know how you are. That to me is a victory, or you’re going, “I’m going to set my alarm for 6:30, or tomorrow, I’m not going to set my alarm and I’m going to let my body tell me when I should do this.” The key is to know which of those people are you and then to seek out the solutions that are right for that. Oftentimes, it’s the time of life that you’re in. One hour of my life as a graduate student was much more important to my career than one hour of my life now. At least in the world of academia, you have these benchmarks. The way I think of it is this. You get on a train. The train starts earlier than you think it does. It starts basically as an undergrad. There are these stops along the way. This is a different train because if the conductor can decide to kick you off at different stops.

That is a different type of transportation.

You’re on this train and if you take care of business before you get to the first stop, you stay on it. You get the grades and the GRE score and you get into a program. The next stop is your first-year paper, then your second-year paper, then your dissertation, then the job market, then tenure and so on. Early is more important than the time on the train later, because you can get off the train as you like later and fuss around and then get back on it and so on. It’s a nonsense analogy.

I think of it as a credit. I got the credit from that TV show. If I get on again great, if I don’t it’s all right. I’ve already passed that benchmark.

The problem in academia is you can’t go back. You don’t get many second chances. There are some, but there are not as many as you would like in that way. The idea behind tenure is that you can take these moon shots. You can do things that are different. You can do things that are risky and so on. Early in your career, it’s hard to do that. Later in the career, it’s easier to do that. To do moonshots and to do things that are risky and so on often take having more time and space to think about things differently. I regularly work on stuff and then throw it aside. That would have felt like a monumental waste of time as a graduate student or an assistant professor, but now it would be a monumental waste of time to keep working on it.

INJ 36 | Engaging Speaking
The Dip: A Little Book That Teaches You When to Quit (and When to Stick)

Seth Godin did The Dip: A Little Book That Teaches You When To Quit (And When To Stick). That was an easy book. I flew right to that, but yes. Knowing when to quit, I like that. I know he’s maybe too mainstream for some, but he gets me fired up. I still like him.

He’s a pro. It’s funny you mentioned The Dip because I don’t know if the scientific evidence supports The Dip.

He’s a great writer and I believe it. I don’t want to hear about it.

It doesn’t matter whether there’s a dip or not, what matters is the idea that, “Have you given this enough time?” In marketing, the idea essentially is that adoption is non-linear. It’s often slow. It’s flat and then it accelerates, and then it flattens again. There’s a bunch of ideas about this. There’s this idea of this tech chasm that happens, especially with technology. That flat part of adoption can be unusually big. The problem with that is companies go out of business because they run out of money. They don’t last long enough to get the acceleration that’s there. In that sense, Godin’s right. He recognizes that improving or success is non-linear, and sometimes people could give up. The problem with that is that most people should give up.

When you know you can’t be the best is also another time. I believe or maybe I made that up. If you can be the best, don’t give up. If you know I’m never going to be the best, I’m going to be a follower and I have to compete on price. On your moonshots, I want to ask. You said you’re a runner and then you said you take walks a lot of times. The stuff that you picked up and then put down, does it ever hit you in your runtime or in your walk time? When does that hit you when you purposefully remove yourself, especially running? I’m drawing a parallel of myself.

I’ve become weird about disconnecting myself.

How recently?

It’s been a slow process. I have an ex who runs and she runs long distances. She runs without headphones. I was like, “Really? I’ll try that.” It’s hard because running is hard, and so the music is nice because it lifts you up and it helps you with your pace.

Scientifically, music will help your pace and help your strength. Scientifically, I read that and I also believe that.

One day, my back was killing me. I did this light workout. It was 100 rope skips, a 50-yard sprint, walk back, ten pushups ten times. It was okay on my back, but I had music going during that. It would have been foolish to not have music going because it makes the experience much better.

Did you hurt your back or is just you’re tall?

I hurt it.

I heard tall people have back problems. As being a guy that’s 5’9” with shoes on, I don’t feel bad for that.


I used to have a chronic back problem and I fixed it. If anybody has chronic back problems, you should send me an email. I’ll email you how I fixed it. I hurt it working out. There’s a trail run near my house in Boulder, it might be my favorite thing about Boulder. It’s a hard run, but it’s not devastating. I try to do it once a week and I do it without headphones. I do it without water. I do it like Spartan and I consider that a complement to my work. Sometimes I come off the hill with a list of things that I need to take care of. Sometimes I come off the hill with profound ideas. I count them out on my fingers while I run so I don’t forget them.

You’re now running with a trapper keep.

I don’t know a good solution for it because if I brought a pen and paper, I would honestly stop and write things down. I’ve thought about bringing a voice recorder, something that’s light that I could do. I don’t want to bring my phone because I’ll be tempted to do stuff with it. It’s a practice that I have had to cultivate, and now I love it. I don’t always think about work. I think about other things. I need to be doing a lot of hard work to get ideas. If I was playing video games all day and then I went on that run, I would think about video games. I want to ask you what are you reading, watching, listening to that stands out. You mentioned already Jiro Dreams of Sushi.

The Ego Is the Enemy by Ryan Holiday. I have a real appreciation for that book.

What is the thesis of that book?

[bctt tweet=”If you can be the best, don’t give up.” username=””]

He uses short stories like Bill Belichick, General Sherman, all kinds of short stories about how people did what was hard, did the grunt work that others didn’t want to do and became successful. It’s not a blog post like, “Do what’s hard. Take this grunt work off your boss’s place.” He’s using awesome examples. From what I understand, the guy lives on a farm, reads four books a day, takes notes about it and then turns them into these amazing books. That’s all he does with his life. I’m jealous but he’s great at it. Ego Is the Enemy is one.

The idea essentially is don’t think that you’re too important, this is beneath you.

Look at all these people and I remember you talking to me saying, “First you’re a comedian, then you’re an actor, then you’re a director,” and how things build on itself. For example, we talked about waiting tables, which is part of my journey to be better at sales and to be able to deal with people.

You needed to wait tables to be a salesperson.

He’s telling awesome little stories in it.

Is this subtle at the critiques of Millennials these days?

He’s young, he might be a Millennial. It could be. I was never totally into Letterman until the end of his career. I picked up Letterman’s biography.

Biographies are usually better than autobiographies.

You would like it because Letterman’s lessons translate to business and it’s interesting to see how he was always the anti-comic. He was telling jokes but not believing his jokes. He was interviewing guests and thinking they were full of BS. That became his character and it’s a new perspective on comedy for me that I never considered. I was born in ‘76, I was around but I wasn’t staying up at 11:00 PM and DVR didn’t exist. It’s interesting to take a peek back even though he’s still relevant to me. Those are the two that I’m reading. Podcasts, I can’t get enough of for whatever reason. I watch a lot of junk TV with my wife because we enjoy it, so I’m not going to talk about that.

Jay, I knew this would be fun. Thank you so much for doing it.

Thank you for having me. It’s great seeing you.


Resources mentioned:

About Jay Mays

INJ 36 | Engaging SpeakingJay Mays is a 20-year sales veteran and stand-up comedy producer. From his underdog beginnings in dive bars to being awarded Best Comedy Venue in Miami, Jay has produced live comedy events for some of the biggest names in entertainment including Viacom, Soho House & Live Nation. As co-founder of Pitch Lab, Jay combines the seemingly disparate worlds of sales and comedy to help professionals be more confident, engaging speakers.


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