Sales From The Street-“Cold Emails & Curiosity" | Donald C. Kelly - 2028

Less than ten percent. That's how many highly targeted emails actually get opened. In this archive episode, pulled from an old Sales From the Street segment, I'm breaking down exactly what I look for in a cold email before I'll even open it, let alone reply. If email opens are a struggle for you right now, this one still holds up. Why Most Cold Emails Never Get Opened People are buried in email. I was already at 67 messages by mid-morning when I recorded this, and I expected to hit 100 by the end of the day. Executives at bigger companies get even more. Less than ten percent of even a highly targeted email actually gets opened. If you want to land in that ten percent, everything starts with standing out immediately, not with writing a longer pitch. Your Subject Line Has to Earn the Open The subject line is the first thing anyone sees, so it has to catch attention completely on its own. A common mistake, according to MailChimp, is a subject line that doesn't actually reflect what's in the email. Whatever you promise in the subject line has to match the message inside. The subject line also needs to spark curiosity instead of pitching outright. It should raise a question in the reader's mind that makes them want to open it. Personalize the Subject Line With Real Research I referenced an example from Sales Hacker where a rep researched a prospect's Twitter, found out he was a Manchester United fan, and wrote the subject line, "Why a Man U fan is the best fit for sales enablement?"That kind of specific, researched detail makes a prospect stop and think the email is actually about them, not a mass blast. The goal is to find something real about the person, then build a question around it that gets them thinking before they've even opened the email. Your Opening Line Has to Deliver on the Subject Line's Promise Once someone opens the email because of the subject line, the first sentence has to immediately pay that off. In the Manchester United example, the email opened by comparing Manchester United fans to sales enablement leaders, tying the personal hook directly into the pitch. Whatever personal detail earned the open needs to connect naturally to the product or service being pitched, right from the start. Write Your Email Like the Letter F I picked this up from The Sales Development Playbook: structure the email so it looks like the letter F. A longer first line, a shorter second line, and lines that keep tapering down after that. Long emails are one of my biggest pet peeves, especially when people pitch me to be a podcast guest. I'm upfront about it: I won't read a long email, and it's likely to get deleted or ignored. Keeping an email close to the length of a text message makes it far more likely the prospect actually replies. Keep the Call to Action Simple and Direct Every email needs a clear call to action that asks for a specific response, not something vague. Simple questions work best, like asking which day works best or whether the topic is something they'd be interested in. The easier the ask, the easier it is for the prospect to just hit reply, which is the entire goal of a cold email in the first place. Skip the Fake Personalization I can spot a scraped, auto-generated email immediately. My LinkedIn profile reads "Donald C. Kelly," so any email that uses that exact version instead of how I'd actually be addressed gives itself away. Prospects notice the same thing. Sending "Hi Barbara S. Smith" instead of "Hi Barbara" is an instant tell that the email isn't personalized. Real personalization means using the way someone would actually be addressed, then tying the rest of the email back to something specific about them. Tie Your Pitch to What Actually Matters to Them The best cold emails connect directly to whatever the recipient actually cares about. For me, that's downloads and value for my audience, so a strong podcast pitch speaks directly to that. Figure out the real business driver for the person you're emailing, then show how what you're offering moves that number, instead of just describing your product. Combine that with the F-shaped structure and a simple call to action, and the email does its one job: move the person to reply and take the next step. "Keep it simple. The simpler it is, the better. The easier it is for me to hit reply and give you a quick answer, I'm game, and I'm all in it." — Donald C. Kelly Resources Check out The Sales Development Playbook by Trish Bertuzzi, the book behind the F-shaped email structure. https://www.amazon.com/Sales-Development-Playbook-Repeatable-Accelerate/dp/0692622039Join TSE Hustlers League this semester to improve your win rate and move deals through your pipeline. https://thesalesevangelist.com/hustlerVisit Blue Mango Studios for help creating podcast production content. https://bluemangostudios.com/Join our LinkedIn cohort and learn to prospect the right way. https://thesalesevangelist.com/linkedin-prospecting-course/ Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales https://www.hubspot.com/products/sales. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin https://tsesales.typeform.com/to/UCMfjZbX. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey http://thesalesevangelist.com/survey. https://tsesales.typeform.com/to/lc5yAa8P We’d love for you to join us for our next episodes by tuning in on Apple Podcast https://podcasts.apple.com/us/podcast/the-sales-evangelist/id788738885, Google Podcast https://podcasts.google.com/feed/aHR0cDovL3RoZXNhbGVzZXZhbmdlbGlzdC5saWJzeW4uY29tL3Jzcw?sa=X&ved=2ahUKEwj5kaXI3Pj2AhVKcjABHW5PDVwQ9sEGegQIARAC, Stitcher https://www.stitcher.com/show/the-sales-evangelist-sales-trainingspeakingbusiness-marketingdonald, or Spotify https://open.spotify.com/show/1NjzsFjQwVrgboUfDvbzd5?si=LdQOJDc1T-WBPMxr1h3RsA. Audio provided by Free SFX, https://freesfx.co.uk/ Soundstripe https://soundstripe.com/, and Bensound http://www.bensound.com/. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

• 0:00Speaker 00

  This episode is brought to you in part by the following TSC sponsors.

• 0:05Speaker 00

  You don't become the world's most valuable women's sports franchise by accident. Angel City Football Club did it with a little help from HubSpot. When they started, data was housed across multiple systems. HubSpot unified their website, email, and fan experience in one platform. This allowed their small team of three to build an entire website in just three days. Three days. The results, nearly 350 new signups a week and 300% database growth in just two years. Visit hubspot.com to hear how HubSpot can help your team grow better.

• 0:46Speaker 00

  LinkedIn Sales Navigator is just plain awesome. Think about everything you need help with in sales. Finding the right buyers, prioritizing the right accounts, reaching out with the right message at the right time. LinkedIn Sales Navigator is built to help. With AI-powered recommendations and real-time account insight, it helps you spend less time searching and more time selling with focus and confidence, all powered by LinkedIn's network of over 1.2 billion professionals. It is the most dynamic buyer network. Accelerate your sales with LinkedIn Sales Navigator. Try it free for 60 days at LinkedIn.com/sell. Terms apply.

• 1:28Speaker 00

  This episode is brought to you in part by Blue Mango Studios. Imagine using a podcast as a lead generation source, not only attracting your ideal customer, but entertaining them and getting qualified leads. To find out more, go to bluemangostudios.com.

• 1:53Speaker 00

  In today's episode, we're going into the archive. I'm pulling out one of the episodes that I did a while back, and it's all around sparking curiosity, specifically with your emails. If you have no curiosity, people ain't gonna open it. Check it out.

• 2:13Speaker 00

  Hey, hey, hey, everyone. Welcome to another great episode of the Sales Evangelist Podcast. I'm your host, Donald C. Kelly, the Sales Evangelist. And I'm so excited for another great episode. I'm so excited to be here with you today. And today, I'm going into archive. I'm pulling out one of my old episodes. This one is called, an episode called Sales From The Street. And we did a small segment a while back, and it was a like 10-minute episode. And what we did was we focused on things that were some of the challenges sellers were facing. Email openings were one of those challenges, and we're still seeing a challenge right now. So I want to pull this one back so you can see it. And some of the strategies, I gave an idea when it comes to creating an F shape with your email. That's all I'll tell you. You'll check it out. If this is your first time listening to the podcast, subscribe, and we'll give you awesome content like this every single time. If you've been listening for a minute, but you haven't spread the word yet about the podcast,

• 2:58Speaker 00

  please go ahead and take this episode link and share it with one other person. But as we dive in, see how I outline the way you structure the email to help you to get response and to spark curiosity.

• 3:12Speaker 00

  Hey, hey, hey, everyone. Welcome to another great episode of the Sales Evangelist Podcast. I'm your host, Donald Kelly, the Sales Evangelist. And I'm so excited for another great episode. I'm so excited to be here with you today. And on this episode today, I'm going to talk to you about some ideas that can help you with your cold emails. This is Sales From The Street. Yes, sir. And Sales From The Street is where I get an entrepreneur or a sales professional to come on. They share a strategy or it's difficulty they had, how they overcame that, and some of the results that they're seeing. And today, I'm going to be the Sales Evangelist slash guest slash the guinea pig and talk about some of the things that I've seen to be able to be effective with cold emails. That has helped me, and I know it can definitely help you as well.

• 3:54Speaker 00

  Well, first off, I'd like to tell you that as an entrepreneur, we get many different emails. As a business owner, I'm sure you probably get to see the same thing as well. Or even as a sales rep, you get other people who are trying to sell to you. Or as a consumer, you know, you get emails sent to you at home. You know, people are trying to get access to you. Back in the days, it used to be the cold calls, right? Where people were bombarding your home phone, or they were calling to the office, and you still see cold calls, but it's not as much as before. And you know, there's definitely different ways that you can be more effective with your cold outreach. But people do a lot of emails. Emails is that new means where people just like, they just go out and spam. And they, and spamming in emails has been around for a long, long while, I guess now. But the problem that I find is that most people just get turned off by it and just delete before they even open emails.

• 4:38Speaker 00

  As a podcast host, I get people who reach out to me who want to come on our podcast. I mean, all different types of emails. And I've seen some that I found to be very effective and some that I found to be very ineffective. And I want to tell you some of the things that has worked and some of the things that may not be the ideal thing for you to be doing. Whether you're pitching someone to come on a show, or whether you're pitching an entrepreneur, a business owner, or a prospect. So, but let's start from the top. One, the very first thing I want you to realize is that people get many different emails, many, many emails throughout the day. So for instance, I'm probably at, right now, I, let's check my email and see what a number I'm at. I'm at, in the morning, 67. So I probably, by the end of the day, I'll probably end up with about 100 emails that will come in from multiple different sources, whether it's people trying to pitch

• 5:22Speaker 00

  or just business in general or whatnot. Now, I'm not an executive at a large organization or even a mid-sized organization. And I imagine their email count probably double what I get, or probably even triple what I'm going to get throughout my day. So you got to think about that. They're going to get many different emails from all different angles, and your email is probably going to get buried. So you got to make sure you stand out. And less than 10%, even of a highly targeted email is open, less than 10%. So you're sending 100 emails, less than 10 of them are going to get opened. So you got to imagine, what can I do to stand out? The very, very first thing that I look for and that most people look for is a subject line. The subject line has to catch my attention. And it's the same thing with anyone else, right? Because that's the first thing you look at. The subject line is bold, so it's going to stand out.

• 6:05Speaker 00

  And according to, I think it was Mailchimp, you know, one of the biggest mistakes that people make is that their subject line is not effective in telling the message of what's actually in the email. So you got to make sure your subject line, whatever you say in the subject line, has to tie to the actual message. It sounds simple, but you can imagine how many people don't do that. And then the subject line, you can't just jump out and start pitching. You have to instill some sense of curiosity. You have to make them, provoke them enough to open the actual email. And one thing that you can do is find a way to make it personalized. You got to make it something that they will think about, something that will resonate with them, that will say, huh, let me look at this, let me open it up. Usually, this could be a question. This has to be, you know, something to provoke them and stimulate them.

• 6:49Speaker 00

  I was reading an article on Sales Hacker, and it's a great site. They have a lot of great content. And on this article that I read on their site, one of the things they mentioned was, I think the article was like, how to write a cold email that 33% of prospects will reply to. And in the subject line of the sample email that they sent, it was pretty cool. The individual wrote this as a part of a company that has a sales enablement tool, and they're reaching out to this individual. And they did some personal research. They went on Twitter, and they found that what he likes the most, and he's a football fan, and American, not, sorry, not American football, he's a soccer fan. His team is Manchester United, right, that he follows. So it said, why a Man Utd fan is the best fit for sales enablement? It's a very short sentence.

• 7:30Speaker 00

  It's not too long, but why a Man Utd fan is the best fit for sales enablement is a question mark. So if I'm a Manchester United fan, and I see an email like that, I'm like, oh, they're talking about my team. You know, let me see what this is all about. And at this point, I would suspend my, you know, standoffish role as the executive. And I'll be like, now I'm a, I'm a footballer. I'm just like, oh, man, let me see what they're talking about my team. And it would spark my interest. So what can you think about? Is there another way that you can do an effective email that's going to grab someone's attention? Is there something that you can personalize? You know, figure that out and ask a question that can stimulate the thought at the very beginning of the email.

• 8:09Speaker 00

  Mistakes That Made Me, hosted by Iman Ismail, is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Mistakes That Made Me is the podcast that asks extraordinary business owners to share their biggest business mistakes, so you know what not to do on your road to success. Join Iman Ismail as she chats with some of the smartest minds in business about how to push through failure and accept it as an important and necessary part of building a business. Because it turns out, your biggest business mistakes often lead to your biggest lessons and then your biggest blessings. One of the latest episodes that just totally resonated was ignoring my cash flow almost cost me my business. And many of us can relate to that.

• 8:53Speaker 00

  If you run a business, sometimes you kind of not focus on the most important thing. The guest was Sandra Booker. Iman has amazing insights and amazing guests, and I highly recommend you check out the podcast. Listen to Mistakes That Made Me wherever you get your podcasts.

• 9:12Speaker 00

  The next thing you want to do, your opening sentence need to tie to that email, the subject line. You need to make sure, because right away, again, the idea is, you just provoked my thought. I actually opened the email now. Now I need to see what is this going to be about. This is where you need to do the catch. And if it's like this Manchester United email, they started talking about how Manchester United fans were equivalent to our champions, just like sales enablement leaders. And they just did a really good job with this gentleman to tie that stuff in. With you as a business owner, what are you selling? What's your product or your service? You found something about this individual. Maybe you found out that they like Celine Dion. Then figure out a way you can tie that into your product or your service. We're not going to brainstorm that on this call, but maybe you can think about some unique way. Like if the person's name is Mary, you know, three things

• 9:56Speaker 00

  that Mary and Celine Dion has in common. And that could be your subject line. And then maybe it's not a question, but you know, or you could even ask a question. Maybe you could say, what are the top three things that Mary Smith and Celine Dion has in common? And you can just go ahead and share those thoughts in the first little bit of the email and tie it back to your product and your service. So that's just an idea, just something that came up the top of my mind. There's a book that I would recommend, and I talked about this before. It's the Sales Development Playbook. And one of the things that they talk about in the book is the idea of making sure your email looks like an F. So what that means is, don't write a long email. That's one of the biggest pet peeves I have, especially when people are pitching me on a podcast. They send me this book. I really don't read all of it. So if you send me an email trying to pitch me to come on a show, I'm giving you the answers right now.

• 10:40Speaker 00

  Please, please, please, please. I get a lot of emails. So don't send a long email. I won't read it. Likelihood of me reading it's slim to none, and I may delete. So, or just like, you may not get an answer from me or one of our teammates. So the key is to make it like an F. So you know how Fs may be, the first line is a little bit long, the second line is a little bit, is a little bit shorter than that one. The third or fourth line are shortened in the second, third line. Excuse me, the second line, yeah, and the third line. So you want to make it looks like, look like that. It's easy to read, and it just grabs your attention. All you want to do, and then at the end, you have to have a call to action. The call to action must be something that's going to provoke them to do something like, you know, which one of these days worked best for you? Would this be something that interests you? You want them to hit reply and tell you an answer. And the easier the emails are, if

• 11:25Speaker 00

  you keep your emails kind of like a text message or an instant message, the easier the prospect will be to reply to you. And when I reply to people, I, they send me these long books, I just send a simple email back replying to them if I do reply back. And it's a, it's just, you know, three sentences, because I don't want to waste their time, and I don't want to, you know, waste my time. So think about it. You don't need to try to sweet talk and persuade. Just give me the simple facts and grab my attention. Why should you be a great guest for our community? And if you can do it in a simple little email, you know, grab my attention, I'm game. We're all in it.

• 12:02Speaker 00

  Think about all the things you wish you had help with in sales. Finding the right buyers, knowing which account to prioritize, reaching out with the right message at the right time. LinkedIn Sales Navigator is built to help with exactly that. It uses AI-powered recommendations to surface leads and accounts that match your goals. So you spend less time searching and more time selling. You get real-time account insights that help you grow your pipeline, personalize outreach, and stay informed about buyer activities. It can't replace the work of selling, but it gives you the data and visibility to sell with more focus and confidence. That's what we need. All of this is powered by LinkedIn's network

• 12:43Speaker 00

  of over 1.2 billion professionals. The most dynamic buyer network, working just for you. Accelerate your sales with LinkedIn Sales Navigator. Try LinkedIn Sales Navigator now with a free 60-day trial at LinkedIn.com/sell. That's LinkedIn.com/sell. Terms and conditions apply.

• 13:07Speaker 00

  Since 2013, we launched this podcast. The goal of the podcast was to share wealth of information, and I feel that we've successfully done so. As a natural byproduct, listeners like you would reach out and ask, could I coach them? Could I train their team? Could I come and speak in an S K O? Could I consult for them? And that is how we gain the majority of our business, and still to this day. So in 2019, one of our clients saw what we did and asked, could we do that for them? We experimented with it, and we started a podcast production agency. Now we create podcasts for some of the biggest brands in the world. And it's amazing. I would love to show you and your team how we can create podcasts for you and use it as an entertaining source, but also educational and a lead generation.

• 13:50Speaker 00

  If you're interested, go to bluemangostudios.com. Again, bluemangostudios.com, and our team can show you exactly what we did. It's amazing.

• 14:05Speaker 00

  The other thing I would say is, don't, you know, sometimes people utilize LinkedIn, and they try to do a personalized generic email is what I call it. So what they will do is use some tool to scrape their LinkedIn account or LinkedIn accounts. And then they will send me an email. And when the email comes over, it will come over a Donald C. Because if you find me on LinkedIn, it's Donald C. Kelly, right? And I did that because there was another Donald Kelly, and I wanted to stand out. So Donald C. Kelly. So when they send me this, I know exactly when it's a screen scraper, when it's not a personalized email towards me. Just take off the C and just put Donald. That's something simple you can do. But if, the same thing with all of your different prospects, don't go ahead and send that generic email. Hi, Barbara S. Smith. Nobody's gonna realize, nobody's gonna be

• 14:48Speaker 00

  tricked by that one. People are humans too, man. We're not stupid, right? So send us an email that's personalized. Just say, hey, Donald, and then go into what it's about that ties back to your subject line. That's it. Keep it simple. The final thing I would tell you is, figure out a way that you can tie what you do to how I make money, or how a business driver for me. So the podcast is, I always want to increase my downloads. I want to provide great content for my community. So in an email, if you're pitching me, can you talk about how that episode, that content that we're going to produce together is going to, one, increase downloads, or provide a value to my community that they're going to say, Donald, this is the best episode ever. You know, people like to hear stories. They like to hear actionable ideas. They like to hear, you know, things that work.

• 15:32Speaker 00

  So, you know, if there's a way that you can do so, well, again, I'm game. Keep that in a simple, tight email. Make it like, look like an F. So top, the first couple lines are longer, and then, you know, shorter, and taper down to the call to action. Obviously, a call to action could be a little bit longer, but you know, whatever that call to action is. But again, keep it simple. The simpler it is, the better. The easier it is for me to hit reply and answer, a quick answer, I'm game, and I'm all in it. And it's the same thing with your prospects. So as you go out, I hope this is able to help you. I've utilized this, and it's helped me to, one, follow up on people who went cold, people who I was out doing cold outreaches to, people who I did warm outreach to, you know, utilize their name, make it personal towards them, you know, grab them at the beginning. The subject line must be catchy. Make the email looks like an F, and have a powerful call

• 16:17Speaker 00

  to action, a simple call to action that can grab their attention and get them to reply. That's all we need. We just need to move the deal from this stage to the next stage. Speaking about moving deals from this stage to the next stage, if you want to improve your win rate and to move your deals along in your pipeline, check out TSC Hustlers League this semester. I am stoked for it. We're going to have a great time. The community is awesome. We started this week, but you can still jump in and get access to recordings for the past session. And you can start applying this stuff, man, applying this content. I promise you, you won't be neglected. You won't lose out. You won't miss out on losing deals anymore. But you got to start right now. Take action. Go to the sales evangelist.com/hustler

• 16:59Speaker 00

  and learn more. All in all, I share this episode, I share this content because I want you to be successful. I want you to be happy. But most importantly, I want you to go out and do big things.

• 17:12Speaker 00

  Hey, I hope you enjoyed this episode. If you did, please take this link, share it with somebody else, and go ahead and connect with me on LinkedIn. I would greatly appreciate that. As always, I want you to thrive. I want you to succeed. Most importantly, I want you to go out and do big things. See you on the next one.

• 17:31Speaker 00

  The Sales Evangelist Podcast is created by the Sales Evangelist Sales Training Organization. It is produced by TSC Studios. Our podcast production manager is Nancy Paul. Our audio engineer is Jershun Obayal. Our video engineer is Dusan Kunado. Guest management is done by Jill Vito and Kristy Virtus. Our content writer is Carlisa Galberith. Our graphic designer is Yurvish Savalia. And I'm your host and executive producer, Donald C. Kelly.

• 18:05Speaker 00

  Sales Podcast Network.