EPISODE 500: Sales and Life Lessons Learned from 500 Sales Leader Interviews with Fred Diamond

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[EDITOR’S NOTE: This is Sales Game Changers Podcast host Fred Diamond’s 500th epsisode.]

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FRED’S TIP: “When you’re doing a podcast, think about your audience, your guest, and then you. That’s the order of priority. And do a good show.”


Fred Diamond: We’re going to be turning the tables a little bit. I’m going to be handing the interview responsibility to my good friend, Zeev Wexler. You’ve seen Zeev before. He’s been a guest on the Sales Game Changers podcast. He also interviewed me back in the summer of 2021. I had done a three-week road trip. Zeev, do you remember that? Went all over the country, went as far as Kansas City, had all these amazing stories, and Zeev interviewed me about that and it was an honor. Zeev and his company have also been sponsors of the Institute. You’ve sponsored our award event, you’ve been a great part in the growth of the Institute for Excellence in Sales. I’m thrilled to have you here as we celebrate the 500th episode of the Sales Game Changers Podcast.

Zeev Wexler: I’m excited to be here. Thank you for giving me this honor. Fred, I’ve watched you, we are good friends, just for everybody to know, and I love you as a person and as a business partner, but I’ve watched you grow. I’ve watched you take this from an idea, I’m not even talking about the Institute, but of course the podcast, from an idea into an amazing, amazing system. I am so happy that I’m here. The first question I have for you, why did you start a podcast, Fred Diamond?

Fred Diamond: That’s a great question. Most of my career has been in marketing, and that’s why you and I have talked a lot about marketing. I was in marketing at Apple Computer, Compaq Computer, product, branding, vertical marketing, et cetera. I started the Institute for Excellence in Sales as a lead generation to meet sales VPs who were customers of mine when I was an outsourced Chief Marketing Officer. It was called Diamond Marketing, and I needed to meet more sales VPs. We had events, we did the award event. It got to the point where I said, “You know what? Running the Institute for Excellence in Sales was more fun than the marketing consulting I was doing.”

I decided at one point in my career just to grow and run the Institute for Excellence in Sales, and it was more of a transactional thing. I had to get members, I had to get sponsors. As a consultant, you can get by with two, three clients a month. When you run something like the Institute, you need to keep bringing in new members, you get them renewed, new sponsors, and my pipeline was kind of at zero. It occurred to me one day, it was August 2017, I said, “I need to meet more sales VPs.”

Podcasting has been around for a while, but it started getting big. I was a huge fan. I used to listen to a whole bunch of shows. I used to be a DJ at one part of my career. I said, “Okay. It’s time for me to start a podcast interviewing sales VPs.” I literally just went to people’s offices. Right now we’re doing all of our shows virtually over the internet, but I would go to their offices with a couple of mics, my ATR2100s. I would bring a DVR, a Zoom H5 recorder. I had these stands and filters, and it looked pretty cool. I would take pictures of me and the VP. I would wear a suit. I would have this green tie that a lot of people would know. That was it. I had to physically meet VPs of sales because they were my customers.

Once I got into the room with them and did the show, and we took a lot of care for the show. I had a sound editor. We transcribed every show from day one. We made these people who have never been on podcasts look good, and it helped get the relationship going. We’ve tripled the business by starting the podcast. There would not be an Institute for Excellence in Sales if we never started the Sales Game Changers Podcast.

Zeev Wexler: That is amazing. Everybody out there, this is such an amazing story. First of all, your podcast is amazing.

Fred Diamond: Thanks.

Zeev Wexler: Second, you have grown your business three times while giving an amazing service to the people that you yourself serve. This is a win-win on so many different levels. I remember when you started, I remember when you came to my office and I remember you attaching the microphones to the desks, and I remember thinking, “Wow, that’s a lot of guts Fred has. Driving from office to office, recording this thing. Who’s going to listen to it?” Then not too long afterwards, I saw that you won the bronze medal as the top sales podcast in the world?

Fred Diamond: Yeah, it was from Top Sales World. We were honored. We won the bronze. We’ve also been recognized by Feedspot as the third best sales podcast. I get 40 people a week, Zeev, who reach out to me to be on the show, and the podcast agencies and various people. We’ve reached a certain amount of interactions. We’ve had over a million downloads, LinkedIn interactions. We transcribe every show.

Zeev Wexler: Hold on. Over one million people have interacted with this podcast that you’re putting out?

Fred Diamond: Correct.

Zeev Wexler: How do you feel about that?

Fred Diamond: One of the cool things is, I’ll give you an example. The way podcasting works, for people who don’t know some of the background, you have a hosting facility where you do the show and then you host it. Then the host spreads it out to Apple, and Spotify, and Google, and all those places. We’ve been using a host called Libsyn. It’s a good, well-grounded podcast ISP type of a thing. Whenever we post a new show, which is three days a week, I go up, but I’m actually the one who does it. Even though I have a team, I like to do it. I like to listen to the show again and I post it up.

I was up two days ago posting a show and we had eight downloads from shows in 2017. Let’s say somebody wants to meet you, they search Zeev Wexler, and you come up as a guest on the Sales Game Changers podcast, which you probably will. You do a lot of things so you come up for a whole bunch of different reasons. It’s like, “Gee, I’d be curious on listening to this guy on Sales Game Changers podcast.” You hit the download button and it gets registered by Libsyn. That gives me a lot of satisfaction knowing that people, their story is going to be told years later. That’s one of the great things about podcasting. We’ll get into this in more detail.

There’s so many things that podcasting can do for you that I’ve learned over the years. One of them is have a great show and it’s going to be out there. If you want to meet somebody, it’ll show up, you can listen for 30 minutes, have some things prepared as you’re about to interview them, apply for a job with them, ask a request, make a referral, whatever it might be.

Zeev Wexler: I’m going to digress for a second. This is interesting because NFTs is something we hear all the time. In the future, you can actually mint these and you can have non-fungible tokens of the stuff that you do. Sorry for the digression. Fred, you’ve interviewed some of the most interesting people that I know. What are the best moments? What were moments that you cannot forget from the podcast?

Fred Diamond: We actually changed over the years. Up until the pandemic, I was interviewing VPs of sales about their career journey. I would ask questions like, “Tell us your greatest sales success.” I used to ask a question, “Tell us about a sales mentor.” I’m actually getting a little bit emotional thinking about some of the answers. Imagine, the people I was interviewing were sales VPs. You don’t wake up and say, “I want to be a sales VP at Microsoft,” or Amazon, or Google, or SAP NS2, great companies. You have to work for 20, 30 years to perform at a high level to get to the highest level of sales. Again, the mission of the Institute is to help sales leaders attract, retain, motivate, and elevate top tier talent. The people I was interviewing have had great careers and they’ve had great mentors along the way. At the point now where I’m interviewing them, they’re mentoring a lot of people. There’s been some amazing stories. I’ll give an example.

A guy named Mike Maiorana. He was a VP for public sector for Verizon. He was episode number 100. Great interview. He said along the way to the mentor question, a woman named Chris Baron, he said she was a senior sales leader at Verizon. She really helped him going. She lives on the Jersey Shore. My parents used to live on the Jersey Shore. I reached out to her and said, “Hey, Mike Maiorana said you’re his mentor. I’m going to be up your way. I’d love to come interview you.” She had just written a book about leadership. I went to her house two blocks away from the beach and she just told me these just amazing stories. The reason I bring up her is she’s become a great friend. We’ve done a whole bunch of things together over the years. I’ve developed this relationship with this person I never would’ve come across if I didn’t ask Mike Maiorana about his mentor.

Another example. I had a guest called Ivy Savoy-Smith with Entercom, and they own a lot of radios in the DC area. She’s now on our Women in Sales advisory board. She’s an African American woman. We talked about radio sales and she told this story about how she was trying to convince advertisers to advertise on an urban station. It was a journey for her to get people comfortable that traditionally weren’t marketing to urban markets to have the comfort to take a risk in marketing to urban markets.

It was very emotional as she was telling the story about trying to get people to understand the value of reaching these markets. We talk about them now all the time. It’s like everybody’s trying to get to markets and there’s new markets. When she was starting 15, 20 years ago, it wasn’t an easy thing to do, and stories like that about how people have overcome career blocks along the way. Back to the mentor thing, there’s been so many warm stories. When you get to that level, you’ve had people help you get there. Those types of stories really impacted me.

Zeev Wexler: Is there any lesson you want to give for other podcasters? I see you as an inspiration. I know that I ask you for advice with things that I want to do. What is your biggest advice to podcasters that want to start something? They’re seeing you here, 500th episode, third best sales podcast in the nation, what’s your advice?

Fred Diamond: There’s a lot. It’s changed me as a person. First of all, it’s introduced me to tons of people. Of the 500 shows that we’ve done, I would say I have contact with 97% of the people. If I were to reach out, they would respond. It’s just helped me develop great relationships as I’m telling someone’s story. It’s typically a story that hasn’t been told before. A lot of these VPs, they do presentations, they do sales kickoffs, and they’ll talk about the product, and the market, and the company. They almost never talk about their journey. We’re giving them this gift to tell this.

When people ask me about podcasting, I always say two things. If it’s going to be about your business, take it seriously. If it’s going to be for fun, then have fun. If you want to do a podcast about coffee with your neighbor, have fun. Are you going to make money with it? No. But you know what? If you’re going to be spending an hour with a friend talking about something you love, have a great time with it.

If you’re going to be treating it as a part of your business, you got to take it very seriously. You got to give respect to the audience, you got to give respect to the guest, and you got to give respect to yourself. Take it seriously, come prepared. I have questions that I would send to people ahead of time. We hired a transcriber. We’ve transcribed every single episode we’ve ever done. We have a young lady, her name is Mariana. She’s based in Spain. Originally she was in Venezuela. She reached out to me one night and said, “I’d love to try transcribing one of your episodes.” It was a Saturday night. She’s now out done close to 500 episodes. She has done a lot of things for us as well.

Zeev Wexler: How did she reach out to you?

Fred Diamond: Just reached out. It might have been through Upwork or something. She just reached out and gave her a shot and she’s become just a wonderful, wonderful part of the team. I asked her, I said, “Have you changed by transcribing?” She said that she’s personally changed because she listens to every episode. There’s so many key lessons. I’ll ask sales professionals, “What’s something you recommend to the leaders? What do you recommend to the sales professionals out there?” You got to be a better listener. They would say things like, “You have two ears, one mouth. Use them in that order.” Or the 66% solution. Almost everybody would say listening. We were getting really deep into how do you be a better listener? There’s so many ways. A lot of people listen to talk. But how do you be really attentive? Look them in the eye and really absorb, prepare so that you know what you’re going to be asking them when they give you the answers, if you will. Taking it seriously, and that’s really critical.

The other thing, and you’re a marketer, I’ve been a corporate marketer most of my life. At Apple and Compaq, like I mentioned, some other companies. Microsoft was a big client of mine. When I first started podcasting, I thought I was going to be the next Joe Rogan. Everybody when they start podcasting, there’s the Joe Rogan, forget about Spotify and all that stuff, he still gets millions of downloads. I’m like, “Maybe a sales podcast is going to slip through.” I happened to meet the guy at the time who had the number one sales podcast, you met him as well. I asked him, “How many downloads do you get?” I was expecting him to say, “100,000.” He goes, “Well, I realized quickly I wasn’t going to get a million downloads. I wasn’t going to be the next Joe Rogan.” He says, “Yeah, I get about 800 downloads per show.”

I was like, “Okay. All right. We’re not going to get a million per show, but 800’s pretty good,” because the podcast for me, it’s fun having this conversation, it’s the highlight of my day, but it’s helped me triple the business because my customers are VPs of sales. If I’m going to expose a sales VP, make him or her look good, we’re going to start the relationship. Hopefully, it’s going to lead to a lot of great things.

Zeev Wexler: What I love about your podcast is it seems to me, and we’ve done a couple, when you ask a question, you really care. I’ve been on many podcasts and sometimes it feels like they’re not even hearing what you’re saying or listening, they’re waiting for their next question. With you, it’s a conversation, and I really feel when you ask a sales VP about their journey, you care, you want to know, you want to learn. I think that really shows the genuine nature of what you do. Now, when you started, I did not expect you to download one million downloads per episode. I want to tell you that you inspired me. You impressed me. I thought you did incredible. I’ve watched it from episode one, now till 500, you have impressed me. What kept you going?

Fred Diamond: Well, first of all, I had to keep going. My business is based on members and sponsors. Companies like Amazon, SAP NS2, Cvent, Microsoft, Salesforce, they all joined the Institute. My customers join as members or sponsors. I need to keep the business going. The podcast has become a great marketing tool. I’ve had a lot of our previous guests who reach out to me and say, “I want you to interview my VP of Eastern region.” You know what I say to them? “Sure.” If it’s going to help me, I won’t say this to them, but I’m saying, “Look, great. I’m going to make them look better.”

I’ll tell you a little interesting twist. I used to ask this question. What are the two biggest challenges you face as a sales leader? Invariably, people would say hiring and recruiting. Then they would say something else, messaging or whatever it might be. I interviewed a guy named Frank Passanante, he’s the VP of sales for Hilton US. I said, “Frank,” I said, “What are the two biggest challenges you face as a sales leader?” He says, “You know what, Fred?” He said, “Everybody is challenged with hiring and recruiting, so I’m not even going to mention that. That’s table stakes. My two biggest challenges are,” whatever he said.

We’ve shifted the notion to asking the question slightly different, but everybody’s challenged with hiring and recruiting. Now, as we’re doing this interview in 2022, the spring of 2022, The Great Resignation, all that stuff is real, man. Hiring is the biggest challenge they face. If I can make them look like a better leader, somebody you want to work with, then they’re going to win, I’m going to win, salespeople are going to get better jobs.

The comment you just made, the fact you asked me how I feel about having over a million interactions, feels great. What feels even greater is I had breakfast today with somebody, you said, “I remember when you interviewed that guy and he talked about Kobe Bryant.” Alan Stein. It was like three years ago. She said, “That really stuck with me.” I get that all the time. People say, “I remember you interviewed Zeev Wexler.” I interviewed you in 2018, and I still get people saying, “I remember that time you interviewed whomever.”

If it made an impact on someone’s life, my motto, my mantra, and you and I have talked about this, is the Einstein quote, “Only a life lived in the service of others is worth living.” I don’t want to sound maudlin here or anything, but the mission, it’s really to help change lives, make people happier, grow their careers, get smarter. We end every single show with, “Tell us an action step. You’ve given us 30 ideas, give us one thing people should do right now to take their sales career to the next level.” If people do that, we’re good.

Zeev Wexler: I’m going to be a little cheesy right now, because you actually made me emotional, because I felt that-

Fred Diamond: I see your eyes are tearing, Zeev. I appreciate.

Zeev Wexler: No, seriously, I felt it, when you say that the life worth living is in service, a lot of people bullshit – sorry. You mean it. Have you ever made people cry on your podcast?

Fred Diamond: We have, and actually, you and I are both crying right now [laughs]. I want to let people know how much I appreciate that. The story I told before about Ivy Savoy-Smith. I could hear the emotion in her story, and the mentors. Most of the people I’m interviewing, again, they’re very successful, and they’ve worked at IBM, Oracle, Apple, great companies. You just don’t get to be a VP by walking in one day and saying, “Okay, I’m applying for the VP job. I’m done working at McDonald’s,” or wherever it might be – no disrespect to people who work at McDonald’s. You’ve had to win. You’ve had to grow people. You’ve had to grow as a leader. The people who you’re learning from are some of the most successful people in technology. There’s these warm stories.

When I think about my mentors, people who devoted a second of my life to tell me, give me advice, give me guidance. A lot of times during the mentor story we don’t really get deep into overcoming obstacles, because that’s a whole separate genre, but I don’t think my listeners are really going to get a lot of value from that. That’s a common thread for entrepreneurial type shows, or CEOs overcoming adversity. For the salespeople, I want to give our listeners ideas, something they can put into play right now to take their sales career to the next level.

Zeev Wexler: I truly love that. We like tips. We like actionable things. You have interviewed 500 people. I want you to give a tip for guests. You’re going on a podcast. Can you give me some tips of, as a guest, what do I need to do? How do I need to prepare to make sure that this is what I want it to be?

Fred Diamond: That’s a great question. I send the questions ahead of time. “Here’s the questions that I’m going to ask you,” so that they can prepare. I’ve had some guests who read their answers. That’s a challenge because sometimes I’ll have a follow up. I remember once I interviewed a sales VP, and I knew that she had all the answers, and I was scared to death of asking an ad lib question, because I didn’t want her to explode or anything like that. Definitely take time to think through, but you don’t have to be cute. I’ve had some guests who they say, “I want to be different. Tell me what to do.” I’m like, “Be yourself. We don’t need you to be different.” This isn’t like you’re watching a sitcom and it’s like, “Well, didn’t they have that same thing?”

Zeev Wexler: Don’t do too much. People recognize ungenuine stuff so easily. Don’t do too much. Just come in, be yourself. Don’t try to be someone you’re not. Don’t change your voice.

Fred Diamond: Don’t change your voice. But I’ve had people who said, “I’m going to answer this question differently,” which is fine. But be yourself, because you’re being invited to be on the show because you’re a sales leader, or you’re an entrepreneur or whatever it is that you’re being invited to. You’re not being invited to be entertaining. It’s not The Tonight Show. It’s not late night TV. It’s not a comedy show. People are giving me a half an hour of their time, or 10 minutes of their time to read our transcript, because they want to get better at their career or better growing people.

The other thing I tell people too, is have a pocket full of stories. 30-second stories. I’ve had people who’ve answered their questions feature-benefit. “Well, tell me about a mentor.” “Well, Fred, I had a mentor who was blah, blah, blah.” I would tell people afterwards and they would say, “How did I do?” I said, “You did great because you’re a pro at what you do, but have a pocket full of 30-second stories.” “Let me tell you about the time that my mentor took me aside after a sales call and said, ‘If you keep doing this, blah, blah, blah.'” I remember, I had people who said they’ve traveled 3,000 miles for a sales call. Those kinds of little, interesting … I had someone who said they drove through snow to get to a sales call. I always say, pocket full of 30-second stories.

Zeev Wexler: I love that. Basically, be personal, be vulnerable, let people into your internal place so then they can actually get to know you.

Fred Diamond: I would say also too, listen to an episode or two of the show. If you’re going to be a guest, if I’m giving you the honor of being a guest on my show, I’m not saying that from a ‘I’m great’ perspective. I’m saying that I have limited spots and I really value my listeners. First and foremost, my listeners. They’re giving me time in their busy day to devote to me. I’m grateful for that and I appreciate that. Some people have listened to, probably not every show because there’s so many of them, but I know I have people who’ve listened to over 100, dozens. If you’re a guest, understand how I do the show, or any other show, understand how I ask the questions.

Someone reached out to me recently, they were introduced to me by a podcast agency. “You really need to have this guy on your show.” I went to his LinkedIn, looked like he fit the bill. I said, “Great. Schedule a Zoom call with me and your possible guest. I want to see him before I put him on the show.” I always do that. The guy got on and he seemed okay. I said, “Well, what do you like about my show?” He said, “Well, to be honest with you, I haven’t listened to any.” I said, “Okay. Well, have you been to the website?” “No, I really haven’t. I’m sorry.” I said, “You know what? Okay, great.” I said, “Here’s my advice to you. Next time you’re introduced to someone who hosts a show, give them a three-minute gesture of jumping to the website, or at least their LinkedIn.”

I don’t even remember who it is because I said, “I’m not going to have him on my show.” If you’re not going to give me the respect of three minutes, I don’t need you to listen to 100 shows. Listen to one, zip through it, read a transcript. That’s the respect you want to give the podcast host. There’s so much value in podcasting. I have an expression, Zeev. If only one person listens to my podcast, then one person listens to my podcast. I’m grateful for that one person if I’m going to impact their life by giving me a half an hour. I want to have 1,000 people. We get 2,000 downloads per show. We get another couple of hundred people reading the transcript. We also post the show on LinkedIn, as you know. We get 1,500 to 3,000 views every show. I’m giving you something. We want those numbers, but if I’m impacting one person, then that’s valuable by itself.

Zeev Wexler: I can tell you, you’re impacting one person, I’m sitting right in front of you. I’ve been impacted. Thank you, Fred, for allowing me to do this. Love sitting down and talking to you. One thing I want to say, I’ve been a part of your organization, the Institute for Excellence in Sales for the past six years. I want to say thank you because you bring in like-minded people. I’ve created friends, businesses, relationships, all through the people that you introduced me to in your organization, and I love association. I feel like that’s what takes me where I want to be in life. You’ve been a big part of my association, love being a part of what you do, and thank you for all these wonderful podcasts and everything you do through the Institute of Excellence in Sales.

Fred Diamond: Thank you to you again. You’ve been a big part of it, sponsor. You’ve been our email supporter, got us up and you’ve done so much for the Institute as well. Zeev, I like to end every show with an action step. I always ask the guest, “You’ve given us 20 great ideas. Give us an action step to have the sales professionals who listen take their sales career to the next level.” I’m going to end the show with this. The value of the podcast has been so life-changing. The fact that you and I are here talking about these memories, and we could talk for hours.

I’ve learned so much about people. I’ve met so many great people. I’ve heard so many great stories. I’ve become a better sales expert by talking to people every day. It’s the highlight of my day getting to talk to people. Podcasting, you do so much. We’re coming out with a book, finally, Insights for Sales Game Changers. It’s probably even out now. It’s going to come out in early May. It’s basically, we took the top 15 words that have been uttered on the podcast. I mean, empathy, listening, leadership, prospecting. We went back and found the best quotes and examples that we’ve talked about. We’re going to get that out there as a book, and eBooks, and Instagram posts, and those kinds of things.

One interview can lead to so much that you could do to get marketed out there. I recommend people do it. Don’t be afraid of it. You’re having a conversation about something you love. It’s been a very valuable exercise for me. Zeev Wexler, thank you so much for everything. For all the listeners, thank you all so much.

Transcribed by Mariana Badillo

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