Tiger Sisters - Stanford Writing Masterclass: How to Write Emails People Actually Answer with Glenn Kramon

Episode Date: September 7, 2026

Thank you to Granola for sponsoring this video. Try it for free at https://www.granola.ai/TIGERSISTERSCheck out our matcha brand, Sisters Matcha at ⁠https://www.sistersmatcha.com⁠ Sign up for our newsletter here: https://tigersisters.substack.com/ When was the last time you wrote an email that actually stood out? Glenn Kramon spent 37 years as an editor at The New York Times and now teaches Winning Writing, one of Stanford GSB’s most popular and competitive courses. In this episode, we talk with Glenn about the top writing strategies that can make your emails, pitches, and professional communication “one in a million” instead of “one of a million.”Tune in for lessons on:✅ Why you should never begin an email with “Hope you are well”✅ The two big qualities that make your writing stand out✅ How to write a cold email people actually respond to✅ Glenn’s 12 essential rules for writing better emails (and cold emails) ✅ What to write when someone ignores your outreach ✅ The power of a thoughtful gratitude noteWhether you’re applying for a job, pitching an idea, reaching out to someone you admire, or just trying to communicate more effectively at work, this is your masterclass on winning writing. Timestamps:00:00: Cold Open 03:55: How to be one in a million not one of a million 05:10: Why you should never say “hope you are well” at top of an email07:09: Personalizing the beginning of an email 09:10: Why Glenn’s class is so popular11:40: How to avoid AI “slop”14:30: What makes a great email from a mediocre one14:57: How warmth and competence goes a long way 18:20: How to be targeted in your strategy for cold emails22:22: Golden Rules for writing emails 25:02: Unpacking the “sh*t sandwich” approach28:37: Start with what your audience doesn’t know, not what it does know 32:40: Golden Rules for writing cold emails33:18: It’s not about you, it’s about them36:15: How to create a connection with the recipient of your email43:10: How to be persistent with your follow-ups48:00: How to write a great gratitude letter53:08: Closing thoughts 🐯👯‍♀️ We’re the Tiger Sisters — your Wall Street & Silicon Valley big sisters Decoding Money • Power • Love✨ New episodes every Monday | Shorts all week ✨💌 Want to partner with us? Sponsorships: [e-mail] trust us?▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for youWhat you’ll get (and keep):▫️ 🚀 Ivy League cheat sheets — no $250K tuition▫️ Personal finance playbooks (salary, investing, negotiation)▫️ Networking scripts behind $100M+ deals & job offers▫️ Real conversations with CEOs, operators & investors▫️ Mindset resets — clarity without the pricey coach▫️ Systems for career, money, and long-term growth💛 LET’S CONNECT~ CHERIE ~Instagram — /cherie.brookeTikTok — /cherie.brookeSubstack — cherieluo.substack.comLinkedIn — /cherie-luo~ JEAN ~Instagram — /jeanluo_LinkedIn — /jeanluo👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters.🛍️ Items:🍵 Sisters Matcha — http://www.sistersmatcha.com🌀 Everything else — https://amzn.to/3z0dx5b 

You've said that one of the things that people should never do in an email is say, hope you are well in the beginning. Our goal is to be one in a million, not one of a million. So you just go straight into your ass, like first five raw dogging the email. Hope the weather is treating you well. Boring. In the age of AI, everybody's default level of writing is improved now. So you actually need to be better than that improved default in order to stand out and be considered a good communicator.

makes you one and a million is two things, warmth and competence. Say what you like and what you would like, not what you don't like. You repeat this all the time. Can you share more about this? What does that mean? It's not about you. It's about them and how you can help them. I fear the day that I get a fourth try email subject line from you or do I offend.

What I want to know, Glenn, is who are these people that you know that aren't responding to four of your emails in a row? How about 10 of my emails? a co-founder of Google. Oh, I'm Cherie. I'm Gene. I'm Glenn. And we're the Tiger Sisters. We are your Wall Street and Silicon Valley Big Sisters.

And we're a top 10 business podcast bringing late night sister talk meets boardroom strategy. Hi, Tiger fam. The ability to write well is critical to business success. Today, we're getting a master class on writing from the iconic Stanford Business School lecturer, Glenn Kraman. He was an editor at the New York Times for 37 years, and today he teaches one of Stanford's most beloved and competitive classes with a long, long wait list, and it's called winning writing. I took this class as a student, and I'm so excited to bring you these lessons. Writing may sound simple, but is one of the key skills that even CEOs and execs need help with,

whether it's writing a cold email, sending a message to your boss, or pitching an idea, everyone can improve their business writing skills. Better writing leads to better thinking, and better thinking leads to better opportunities. In this episode, Glenn shares how writing well can make you one in a million. We'll talk about how to literally write a good email because no one actually taught you,

how to write cold emails that actually get responses, and why you should never say, hope you are well in the beginning of an email. Glenn's class winning writing at Stanford is consistently lauded as one of the most useful classes Stanford students have ever taken. And we are bringing it to you guys today for free with Professor Kramon himself.

So buckle in. I am so freaking excited. This is going to be a master class in communication. Let's dive in. Glenn, thank you so much for coming on Tiger Sisters podcast. I'm thrilled, but before we go on, I'd like to return the compliment. I'd like to praise the Tiger Sisters

and your earlier podcast because it got me a big gig at South by Southwest. They called me up last year. They said, we'd like you to speak. I said, how did you find me? It must have been my articles in the New York Times. And they said, no, no. We heard you on Tiger's Sisters. The world is changing.

Yeah. It's amazing. We're so glad you can come back onto our podcast. Yeah. And so as we dive in, we have some hot, hot questions. and one of the most controversial things I'd like to tackle. So this is one of your most talked about takes as a professor. You've said that one of the things that people should never do in an email is say,

hope you are well in the beginning. Can you explain this? Because is there a place to wish people well in an email? And this is a pretty hard email habit to ditch. So what should we do? You mentioned earlier our goal is to be one in a million, not one of a million. not one of a million. If you begin an email with hope you are well, you're one of a million.

How do I know that? In my class, I ask students, raise your hand if you begin an email with hope you are well. And slowly, some of them are sheepish, at least half the hands go up. And it's true. We all do it. It's a habit. AI does it, by the way. So to distinguish yourself, which you need to do, you begin, you have five words.

People are reading on their phones. Sometimes they can only see five words. Make them smile or just get right to the point. I know what you're thinking, oh, but that's very rude. Well, if you want to say, hope you're well, say it at the end. Cheers, all the best. Hope you're well. They all mean the same thing.

But don't waste their time at the beginning. people just don't even notice it. That's what upsets me. You want them to say, wow, the minute they start reading your email. Yeah. So you just go straight into your ask, like first five raw dogging the email. Yes. And you might say, well, wait a minute.

I don't want to ask for something in the first sentence. Okay, you don't have to. You could say something that makes a connection with them. Anything but hope you are well because it's so generic in people's eyes basically glaze over, hope you are well nowadays. Yes. And same thing, but hope you're having a happy summer. Or hope the weather is treating you well.

Boring. We want to capture people's attention. So does this apply for both normal emails, correspondence with people we know, and also, we're going to talk about cold emails, but does this also apply to cold emails? Even more important with cold emails because you're hoping they're well. You don't even know them. So, yes, for sure. the colder the email, the less you know them, the more you want to get straight into it. I love that.

I could see it being a habit that you ditch if you're being introduced through someone. So you could say, hi, Glenn, Sheree introduced me or Sheree thought we should connect, blah, blah, blah, you don't have to say, hope you are well. That's a great introduction. But if you don't have a warm intro or someone to reference, what do you say instead of hope you are well? Just give us one quick example. Okay, yeah. I just did it when I met you.

We met formally for the first time a few minutes ago. Yeah. And the first thing I said to you was, do you know Evan Spiegel? Did you work with Evan Spiegel? Yeah. And you did. Yeah. No reason you can't begin an email.

Hey, I see you work with Evan and then make the connection that way. Okay. So it's so easy these days to scrape the web. And I was telling Cherie that she's an expert. on using LinkedIn. And LinkedIn is a, everybody should have a LinkedIn profile, oh, by the way. LinkedIn is a wonderful way to find information about people. Their Instagrams, and best of all, though, is still to ask people who know them.

Hey, what do you know about that person? My favorite example is always, I had a student this quarter who I learned that she had been babysat by the guy who is now the Green Bay Packers coach. Okay. And I said that in class and the whole class laughed and she was shocked that I knew that. That's what you want. And by the way, it's not something like I hear you're on your ninth marriage. It can't be offensive.

Right. But you want to make people smile and say, hey, how did she know that? And I love the point that you want to capture people's attention in the first five words. Also being very thoughtful about the subject line as well, because if someone's reading an email on their phone and maybe perhaps it's also zoomed in, you're not really seeing much of the email. So you really need to make use of the limited real estate you have. So to put a really fine point on it, if you look at someone's LinkedIn, it says they love to hike. And even if you don't know each other, would you start off the email being like, hi, Glenn, I hear you love to hike, so do I. And then move into your content?

Sure. Well, or that's an excellent question, or you can use it as to PS. If you're going to say, well, this email is too important to begin with something like, I hear you love to hike, fine, then end with that. P.S., I hear you love to hike. I just went on a hike in the Dolomites that I think you probably would have loved. Leave them feeling good. Maya Angelou said it best. She said, people forget what you said. They'll forget what you did. They'll forget what you did. They'll never forget how you made them feel. So after you've written that email, ask yourself, how will it make them feel? And if you end with the PS like I hear you love hiking, they'll feel good. Okay. So Glenn, stepping back a little bit, I think some people might be surprised to hear that a class called winning writing is one of the most popular classes at Stanford Business School, which is where, you know, you would think you would learn about accounting, operations, M&A. So why, can you tell us a little bit about why your class is so popular? It's such a relevant question now in this age of AI.

Because now AI can do your writing for you, right? And I remember when Chachy PT came out four years ago, a student that first day said, so what's your next job going to be? I said, what are you talking about? And he said, chat GPT. I said, what's chat GPT? Within five minutes, we had it on the big screen. I was looking at it.

I started playing with it. I wrote a column about it. At the time, it was mediocre. Now, AI is so much better. AI can help you improve your writing. I encourage students to use it. But still, you need to be one in a million. If everybody's writing is improving, then you have to be even,

better. And that's what I try to teach are the techniques that can differentiate you from everybody else. And the other thing is a lot of people, I'll often ask the class, how many of you suffer from writers block? At least half the class raises their hand. And the fact is a lot of people hate writing, or at least they're intimidated by writing. And I'd like to make the process of improving fun, because it really is fun to write. And the more you do it, the better you get. It's like jogging or playing the piano. I actually think that's kind of a hot take, but I really agree with it that in the age of AI, everybody's default level of writing is improved now. So you actually need to be better than that improved default in order to stand out and be considered

a good communicator. Yes. Well, I would also add that. Now that everyone is using AI, AI's model is based off of the information that's already out there. And so that just kind of brings everyone, like Gene said, to the same baseline. And everyone's e-mails start to sound the same. You are so right. And that's just in the last six months what I've started to hear, the term AI slop. So what I'm hearing from my students who've gone out into the workplace and are managing teams, they call me up and they say, I can't take it anymore.

Everybody's writing the same because they're all using AI. And would you please come into my company and teach them how to make their emails, their LinkedIn profiles, their web posts one in a million? Yeah. I usually use AI in my writing process. If I'm writing an email, that's a little bit more involved. But I find that I have to go back in and make it sound less AI. So I have to go in and make those edits, not really to revert because I like some of the things that's added.

But I'm like, I wouldn't use some of these things. For example, like in an email, it'll say, so here's the ask, colon, and then make the ask. And it just sounds so. I hate it. It just sounds so chatcheevety or so, you know, AI that I'm like, delete, delete, delete. I just make the ask instead of saying, so here's the ask, colon. Like, not this, not that, AI. Oh, I hate it.

I hate it so much. There are now apps that take your writing and make it sound less like AI. After using AI. Yes. But I warn you, some of the things AI does is right. Like using an M-Dash. I love the M-Dash. Tell me why.

Okay, because, okay, this is, I don't talk about this a lot on the podcast, but in undergrad, I was head of the writing program at Dartmouth College. So I was a writing assistant, which is basically a TA for intro to writing classes at Dartmouth for many years. And we also had a writing program that was basically peer tutoring for writing. And I was the head of that program for several years. So I personally deeply, deeply love writing. She's an excellent writer. A such an important skill.

And it is all the more important in this day and age. And that's why I'm also so excited for this episode. And she's a big fan of the MDM. A big fan of the M-Dash. And also, there are so many things now in AI that they've shown, for example, the word delve. AI loves that word. So it's being the usage in common writing has increased like 20,000 percent or something. But I used to use that word all the time organically, but now I can't use it anymore. Yes, you can. Don't be intimidated by AI. And this goes back to the M-Dash. So I've had many students say, well, I don't use M-Dashes anymore because that's a clue that I'm using AI. So I use a hyphen instead.

No, no, no, a hyphen miss wrong. And m-dash is correct. So just ignore AI. What really your writing needs is your voice, yourself in it. Okay. And people won't even notice the m-dashes. They'll get past the don't use m-dash phase. Yes.

Well, you're speaking to your people right here. Okay, Glenn, moving more specifically to email writing. So with nearly four decades at the New York Times and at Stanford, you've seen a lot of good writing and a lot of mediocre writing. So specifically on email writing, since it's part of our every day, what makes a great email that grabs you from the very start and what separates it from the ones that lose you immediately? So I talk about, especially a cold email,

because I think a lot of us are writing emails looking for jobs, money, opportunities. and we're writing to people we don't know. And what makes you one in a million is two things. Warmth and competence. Most people have the competence because they're trying to prove that they're good. But I'll stick with competence for a second before I go back to warmth. The problem is they're too vague. They use, and I actually brought some examples.

So to show your competent, you don't use, vague terms like resilient, I'm resilient. How about instead, and this comes from my colleague Rachel Conrad, who's a great communicator in Silicon Valley, instead of I'm resilient, my first startup went bankrupt, and as a result, I conserve cash and manage the most efficient early stage sales team in biotech. That is showing, not saying. That's what you want to do. Another example, people always say, I'm bad.

tested. Okay, what does that mean? Just give an example. I worked in Washington on my car company's government relation team during the UAW's targeted effort to unionized plants in Ohio. It's cinematic. It comes alive. One more. People love to say this is almost becoming a cliche. I'm a Swiss Army night. Okay, okay, I get that. What does it mean? Oh, how about this? At age 17, I managed social media, customer retention, finance, and HR simultaneously for my family business, a diner struggling through COVID. Suddenly, that's a movie scene. That's what you want.

So that's the competence part of it. Then comes the warmth. The warmth is what will make someone smile. And again, so much depends on your doing research, not only on the web, but if you're if you possibly can to talk to the people who know those people. My favorite example, I had a student, actually I taught at a company called Slack. We all know Slack, great company. This was somebody who was trying to persuade a company to use Slack.

So the emails weren't returned. One, two, three. She said, you know what, I got to pull out the heavy artillery. So she did research on the person she was trying to reach. and she found out that he was a huge fan of telenovas, and in particular of a star name who goes by the name, Roheelio. So she found a service called Cameo,

and she got Roelio, who I think gives the money to charity, she pays Roelio to do a call, video email to this person. And she got an answer. That's what you do. You've got to work a little harder. And for those of you who are worried about, it takes too much time to do all this.

Tell yourself, okay, instead of sending 10 emails, I'm going to figure out who are the three I most want to answer my email and spend more time on those emails. Interesting. Okay. So I hear you're saying instead of a sort of spray and prey method, which I think a lot of people are doing these days for many things like applying to jobs, trying to find a connection. They're like, okay, got to get through these 50 emails. I have to send them all and see who responds. You're saying, instead of 50, pick five, be more targeted, be targeted, and then go deep on each person and construct an email that is undeniable, right?

Like that you can't not respond to by doing a little bit of research on each person. Yes. You know, there is a comedian, a Canadian journalist comedian named Narwar, who's hilarious. and he interviews rappers. Typically, they don't want to, and other musicians. They don't want to talk to him. Who is this nerdy guy?

But he finds out something about them. They can't deny him, to use your word. So my favorite is, there were two, Snoop Dog. So Snoop Dog is pretty famous guy. Now, this was a while ago, but still. So Nardwar found a video cassette, because that's what they used back then, of Snoop Dog. Snoop Dog's very first movie.

And in the interview handed it to him, Snoop Dog was blown away, saying, I don't have a copy of this myself. They're all saying, how did you find this? You put a little more effort into it. And these days, there's so much information out there, like you were saying, on LinkedIn or on Instagram, people share more about their lives. And if you can find that piece of information that you can connect with them and put it in your email, it'll make them smile, it'll make you more memorable, and it'll help you stand out in the sea of emails they're probably receiving. Exactly. Another thing that Nard War did, Pharrell Williams, he found Farrell Williams's very first album and gave a called the Rump Shaker and gave him a copy of it. And Farrell Williams said, this is the most amazing interview I've ever done. Yeah.

People do appreciate that you make the effort because a lot of people don't. So you're kind of really advocating for that sort of like old school putting in the effort in order to stand out and personalize your email. It's almost as if the email today, I think, is kind of almost considered very functional, but you're kind of bringing it back to being like a letter. Yes. It's funny, as you were talking about that, the door-to-door salesman used to have to do that. I mean, you'd have to have ideally enact where when they opened the door,

you had two seconds before they slammed the door on you. And when a handwritten letter, by the way, would also be such an exceptional way to try to reach out to people because they're not used to getting them anymore. So between Tiger Sisters podcast, our Macha brand, our personal meetings, and the rest of life, how many meetings do you think we have in a week? I don't want to guess too many. I honestly can't even put a number on it at this point. But the worst part is not the meeting itself.

It's actually all the follow-up work you have to do after the meeting. Yeah, cleaning up your meeting notes, trying to figure out who has which action item, what are the timelines and deadlines and all the bullet points coming out of every single meeting. And that's why we've been using granola lately, which is a AI-powered notepad that is built for the way that real people actually meet. So here's how it works. You take rough notes like you would in any normal meeting, and Granola transcribes the meeting securely in the background.

Then it turns everything into clean, structured, actually useful meeting notes when the meeting ends. So Granola works through your device's audio, which means it integrates seamlessly with the video conferencing tools you're already using. If meetings are eating up your day, granola is a no-brainer. You can try it totally for free at granola.a.ai slash Tigrisale. That's granola.a.ai slash tiger sisters to get your time back. Try it for free at granola.a.ai slash tiger sisters. Alrighty. Now back to the show.

I want to go to this lecture that you have in our class and you talk about the 12 rules for email. And I'd like to read through them because I think they're so pertinent. But I do have some questions on specific ones that I'd love you to share moron. So number one is know your audience. Number two, say what you like and what you would like, not what you don't like. We're going to come back to that one. Number three, know your main point before you start. Number four, clear personal subject line indicating urgency. Number five, start with what your audience doesn't know, not what it does know. Six, be more formal if you're not sure what your audience expects, like dressing for a party.

Seven, start fast, get to the point quickly, not at the end. Eight, be shorter. Nine, vary the length of your sentences. Some very short, some longer. Ten, write it as you would say it to family or friends. 11, add some warmth, even humor. 12, assume it will be on the page one of the New York Times or distributed to everyone you know. Which would be even worse as far as I'm concerned.

I mean, I would say number one is very important. Know your audience, but I think that's pretty straightforward. We've discussed that. Number two, say what you like and what you would like, not what you don't like. You repeat this all the time. Can you share more about this? What does that mean? Yes.

So, especially if you're going to be a manager, you've got to realize your employees might be a little bit afraid of you. You think you're wonderful and charismatic, but you're the boss. And if you come in and say, I hate this, they stop listening. They're immediately on the defense. And they're thinking, am I going to get fired? They can't concentrate. So if you possibly can, in anything you write, start with praise, say what you like, especially

the people below you, but even the people above you, then they're not defensive. And then you want something. So then you say what you would like, and they're much more receptive because they think, well, he likes me. I'm still employed. If you say what you don't like, and a lot of people in business say, oh, no, that's a, you know,

people get used to my style. I always say what I don't like. It's true. There are bosses who are beloved, and they do say what they don't like. But I would just say, be careful when you're writing, especially to people you don't know. If they don't know that's your style,

they'll try to go around you. That's the other thing that can happen. So you're a proponent of the good old fashion shit shit sandwich yes yes and and this the the the meat inside depends on how bad the situation is when you're doing a performance review some people the sandwich the bread the compliments is very thick okay because they're wonderful and of course the best people are always the ones who can improve because that they're humble so you do offer them suggestions but if you're dealing with who's troubled, then the inside of that sandwich, the things that you would like are much

thicker. You spend most of the review on. Here's what we need. We're going to talk again in two weeks. We're going to talk again in a month. And if you're not better, sorry, but this may not be the best place for you to work. Glenn, on number four, clear personal subject line indicating urgency. Can you give us some examples of what that might look like. There are people now who get a thousand emails a day, and not even talking about text. So they almost don't see your subject line unless it distinguishes itself. And this is back to the know what's important to them. That's where it starts.

So I joke, my favorite football player is a guy named Bryce Love. So I tell the students, if you want my attention, just mention Bryce Love. And I'm going to open the email. Okay, that's true of anybody. We're human. So that's the first thing. The other thing is you can personalize it,

even if you don't know something about the person. If you're like writing to a colleague, you could say, insights from latest meeting. Okay. But that's kind of, what if you said, my insights from our latest meeting? Just words like that will personalize it. But most important is to just say what is what is most important to them so that they will open it.

I think I forward you an email I received a few months ago that was infuriating. I shared with you because the email subject line was something of the effect of like, oh no, your bank account has been hacked or your account has been hacked. And I was in a panic mode. I clicked into it and the email starts off with now that I have your attention and they were trying to sell me some sort of service that I was not interested in, especially after reading this like fake out, urgent, wrong, like morally wrong subject line. That was crazy. And that fishing like that is happening more and more and it's looking better and better.

The New York Times just sent me, I think all of us, in email. and it looked really legit and we opened it and they said gotcha you can't do that don't open and i'm i try to be really careful about what i open but it was so good that it got me so the idea that somebody plays this trick on you with everything else that's happening really bad news bad practice but i think that all goes to show that the subject line is so important and people pay attention to it. And then on the number five, I love this one. And because it's not very intuitive for writing emails, but it's obvious when we talk about it. Start with what your audience doesn't know, not what it does know. Can you share more? Yes, I'm always shocked by this. We're also

impatient. We want to see immediately, what is this? And instead the email starts with telling you something you already know. So like if you're pitching a business, you begin with two paragraphs about why climate change is bad. We all know why climate change is bad, rather than talking about how your business deals with climate change. The example I always use in class is, so this was a great idea sent to Jeff Bezos, CEO of Amazon, when he was CEO of Amazon, and here's how they originally began. So I'm going to read this. Dear Mr. Bezos, you have transformed industry after industry by changing how people interact with and receive traditional services, whether it be books or the retail experience. I can just see Jeff Bezos, who does apparently read a lot of his emails, say,

I didn't know that. Have I transformed business? I'm going to keep reading. Oh, next sentence. Now, as you begin to look at health care, I have no doubt you will again change how an individual receives care in the U.S. So that's why I'm going into health care, Jeff Bezos, will say, no, no, no. This is, so we redid the ask. You can do it in one sentence. Dear Mr. Bezos, I can help Alexa help patients needing personalized follow-up care. A Stanford MDMBA, ooh, that's impressive. I'd greatly appreciate a few minutes to discuss how voice-enabled platforms can transform how we deliver health care.

So whether it's Jeff Bezos or one of his millions of assistants reading this, they can pretty quickly figure out what this is and who needs to read it within the Amazon organization. So please surprise them if you can. Make him say, hey, that's pretty interesting. I love that example because it showcases so many of the roles that we just talk about. about. It's a really good example where there's no hope you are well. There's no intro at all. It just goes into, dear Mr. Bezos, I can help with this thing that you're working on because I'm qualified in this way. This is my experience and then this is what you can expect.

It's so true, Gene. I didn't think of it that way, but really, I can help. Most people will continue reading if you tell them you're going to help them. Offering something to them before even asking something. Yes. Exactly. I could imagine, though, that if for a generation of people that are so used to starting an email with, hope you are well, it's going to be a leap. It's going to be hard to get rid of that and just start straight with, I can help. I can do this. Like it almost feels a little bit presumptuous.

It's too forward for a lot of people. Exactly. But especially somebody like Jeff Bezos, that's what he wants. He doesn't want you to waste his time. I met Jeff Bezos almost more than 25 years ago, and he was just starting Amazon. I was at the New York Times, and he came to the Times. And I was so impressed about how much he cares about writing. And Amazon, I'm sure a lot of you know this, has a writing culture that doesn't want to put up with BS and time-wasting memos.

Hey, Tiger fam. Take five seconds to subscribe to the Tiger Sisters podcast. When you subscribe, you are notified every single time a new episode drops. And if you're listening on Spotify or Apple Podcasts, please rate us five stars and leave a comment about this podcast because it really helps people discover our content and it helps us to continue to make the show for you. If you're listening to this on Spotify right now, take this opportunity to turn on the video. Thanks. Now back to the show. Okay, Glenn, so now that we've talked about your 12 rules for writing e-m-mail, I want to get into your special subset of rules, your golden rules for writing cold emails,

because I think those are the hardest emails to write and everyone struggles with them. So tell us a little bit about your top rules for writing a cold email. I think the most common mistake is that people are asking for something. In a full email. Of course. In a cold email. And even they're applying for a job and saying, I'd love this job because I would learn to do this that. They're not there to teach you. It's not about you. It's about them and how you can help them.

And that's, I think, what people always forget. Show them how you can help them. And they're much more likely to respond. So we were talking earlier about beginning fast. And you just did it. Here are a couple of examples. I can help your company make the AI transition. Now that's vague, but it's going in the right direction. If you can be more specific about how, that's really powerful. People will keep reading if that's the first sentence. Another example, I can expand your presence in Southeast Asia. Oh, we don't have anybody there.

Okay, that's good. I'll keep reading. I've crunched the numbers, and I've found a big business opportunity for you. Most people will at least say, okay, what's the opportunity? And you can't fake them. You have to give it the thought. And I had a reporter at the New York Times. My first hire was this brilliant reporter named Tim O'Brien,

who now runs Bloomberg Opinion. And on our interview, so this is 30 years ago, he comes in and he says, I'm a reporter for the Wall Street Journal. Here are the first 10 stories I would write for the New York Times. And then he listed them. I thought, man, not only are they great ideas, but this guy really prepared. Yes, he liked this all the time.

That's what you want to do. And he was my first hire. He gave you a listicle in real life. Exactly. Before they were invented. There was no listicles in 1997. That's correct. Exactly.

So, you know, it was John F. Kennedy who said, ask not what your country can do for you. Ask what you can do for your country. Just substitute the word company. for country. Ask what you can do for that company and show them what you can do for that company. I think that's the number one most neglected skill. A couple of others drop names. My goodness, find out who they know and perhaps they know somebody you know and that person can introduce you. People are always likely to, more likely to respond if they think,

Oh, my friend suggested you contact me, I better respond because I don't want to anger my friend. Okay, I don't want to let down my friend. So just drop in names, get somebody, and then ideally get someone to forward your email and say, hey, Gene's pretty darn smart. You know, you really should look at this person. And they're going to say, wow, okay, a recommendation from this person, I will look. Yeah. And the other thing, I think the two most important words in a call call letter,

are like you, like you. Because that is where people will feel a connection. So I actually, of course, brought some examples of like you. Like you, I started my entrepreneurial journey very young. Like you, you guys are entrepreneurs. Not a car washing business like this person. I bought candies wholesale and retailed them at my school. The guy's going to say, oh, that's pretty cool.

I was like that in school too. Or like you, I'm starting a business with my partner or with my sister. Like if you guys were writing to somebody and they're doing exactly what you're doing, they're so much more likely to answer. And here's another one. Like you, I've decided I will build a business in an industry where, People like us are underrepresented. People like us.

Yeah. It's so much more likely to get a response. You make a visceral connection. It proves you have something in common that binds you. It creates a connection between the recipient and this person that they've never, they have no idea who they are. But they're like, oh, well, like me, they, X, Y, Z. so you kind of feel almost this like moral responsibility to respond that you're kind of generating

by writing this email. Yes. These are all like the ingredients of how to get someone to respond to you. And I feel like it's a kind of like a super cold email if you put all of them together. My favorite one is making a cold email warm by name dropping. Like our mutual friend Matt Abraham suggested I speak with you. or asking Matt to forward along an email because you're more likely to open it if you know it's coming from someone important that you know. I feel like so many of these suggestions that you have or these rules are very much about crafting an email.

It's almost like it's a lost art of crafting an email. The art of the email. It's not just like we're so used to being just a functional tool like sending it off, just shooting off and throwing it into the internet. The word handmade comes to mind. Yeah. So one more, one warning about like you. Mm-hmm. Because some students do this.

Like you, I believe that AI will change our futures. Don't do it. Too generic. It makes you one of a million. Who doesn't believe that? It's just the opposite of people like us. Make it as specific as possible. I feel like one way to sum up.

memorize a lot of these rules is that if you were to follow each of your rules, every email that you write could only be received by that one person. You couldn't just copy and paste it and send it to your list of, you know, 20 people you're trying to hit. You just said the most important thing we've said in this half hour so far. Yes. Yes. That's what we mean by handmade, handcrafted, is it has to be customized for that particular person. That doesn't mean you can't have a job. generic email, the core of the email, you could be sending to 20 people, but it needs to start with something specific to that person, end with something specific, and where they know, and the subject line, too, they know he's only sending that to me. I love, we have a wonderful student named Khalil Fuller during the pandemic. He realized that people were waiting in line for food. It was really sad, even in the Stanford area.

He said, this is ridiculous. Why don't we give people gift cards so they can go into a supermarket? It's so humiliating to stand in a food line. They could just go into the supermarket, get the same food. The supermarket's open all the time. The food line's only open in certain hours, and they've got kids at home or they've got a job they can't leave. So he started gift card bank, which effectively you and I, and other people and the supermarkets help subsidize, just same with food banks,

gift cards for people to go in the store. So he had to reach out to supermarket executives. And originally their email read like, I hope you're well. I hope you're doing okay during this pandemic. And I said, no, no, no, look the supermarket CEO up. There's so much, if you're a supermarket CEO, there's a lot of information on you online. So just find out something about this guy. And it turned out this guy had started at the very bottom.

And CEOs are very proud of that. And a lot of the people, Khalil, was trying to help, are at the very bottom. And he said, you can probably relate to this situation. And the other thing is, this guy had had, he was old enough that he probably knew people who'd survived the Great Depression. So they brought this up. And I thought that was magnificent because it's clearly aimed at him and him alone. And, of course, gift card bank is now, I think last time now raised, including in the L.A. area right here after the wildfires, has raised $80 or $100 million for people to go into grocery stores. So it really works. He got that answer.

Started with an email. Started with an email. A very carefully crafted email. Yes. I love that. And a great idea by Kaleel Fuller. Hey guys, it came to my attention that some of you don't know, we have a matcha brand. What? A matcha brand?

Yes. Some of my friends were talking to me like, wait, you guys have a matcha brand and it's called Sisters Macha. Gene and I started it in October 2024. And it's something that means a lot to us because I lived and worked on the farm where we source the matcha from. This matcha brand is our baby and we are so passionate about it. And we really love everything that has gone into it. there's just so much love and passion that goes into our company, and we want to share it with you guys. We source from a small family farm just an hour and a half outside of Kyoto called Wazuka is the name of the town, and it's absolutely incredible. We've visited the farm, we've worked on the farm, and we're so excited to bring it to you. So you can find out more at sisters matcha.com.

That's sisters matcha.com. All righty. Now back to the show. So one question I have, and I think a lot of people might have this, is what if I spend all this time crafting this amazing personalized cold email and I've sent it to the person I've waited a week I waited two weeks I follow up I follow up again and no cigar they don't respond crickets what do I do then so glad you asked this don't give up so if they don't decide typically if they haven't responded in the first few days they're not going to respond So maybe you wait a few more days and then you say, forward the email. You could say, just assuring you saw this.

Okay. Okay. Or you could say something just happened that freshens. You mentioned, hey, this just happened. I know you'll be interested. I emailed you last week. Would you have a look? It was like treating the person as your friend.

Yeah, just as a human being who's very busy. Yeah. But instead of just saying, I know you're busy, you're much more active in trying. to get a retention. So the third thing that I do is in the subject line, if I'm trying a third time, I'll say third try. And then fourth try. And then fifth try.

And especially with people I know, because there's no excuse if you know the people. I write in the subject line, Do I offend? Question mark. And do people respond after that? Yes. Now, there are some people who never respond, but they're very few. And frankly, you say, do I really want to work for that person anyway?

I always say that, and I advise people, you know, it's not just emailing, you're also responding to email. If you don't respond to email, people will assume you are either arrogant, aloof, or overwhelmed, or all three of them. And they'll say, I don't want to work for this person anyway. Okay. If you do respond to email, people will assume you are warm, personal, and really they will want to work with you.

So if nothing else, say, hey, thanks, but no thanks. Anything is better than ghosting people. True. And anybody who's been on a breakup probably knows about that. By the way, I asked my class, how many of you have ghosted people and how many of you've been ghosted and always more of the Stanford MBAs have been ghosted? I don't know what that means. I fear the day that I get a fourth try email subject line from you or do I offend.

But I never will because you're so good at responding. Look, I know you guys are really busy. And if somebody, that's a good question. because if I know you, I kind of know your rhythm, so I know it may take a couple of days to you to get back to me, but you will. I don't worry. Somebody you don't know it's harder.

You just have to kind of guess. But no one would be offended if you email them a week later and say, just assuring you saw this. They know how email works. Yeah. And I really love the other example you gave of giving something to freshen up the email. Like an article came out or something. relevant to the recipient so that you can, like another reason to reach out and you're delivering

value right then and there in addition to your original ask. That's so true. That's the best thing to do. It takes more time, but people, again, appreciate the extra effort. What I want to know, Glenn, is who are these people that you know that aren't responding to four of your emails in a row? How about 10 of my emails? A co-founder of Google.

Oh. People say you don't have the email address. I said, I have the email address. I've tried every wish way. I've used every trick in the book that I teach. Nothing is working. So Sergei Bryn, please, respond to my email. You just need a-tenth try.

10th try. No, you just need to corner Sergey in an in-person event and then demand an answer. Well, and I've considered doing that too. You know, he sits, he lives locally and he rides his bike. and I was thinking of jumping out in front of him, like the guy in front of the tank in Jenerman Square, and just say, stop. Sergey, does he offend?

Does he offend? The answer is probably yes. That's one good thing about trying. I have a student named Lucas Zelnick, who became a comedian. And he said, you know, you can turn the bad things that happened to you into a funny story. And so I now document my efforts to reach Sergey, been in my class. And the students find it pretty funny. So it's true. He's never answered my email,

but I got a story out of it. And at this point, I hope he doesn't. So you can continue the story. Exactly right. I don't know what I'll do. You'd have to change all your coursework in emails if he responds. Yeah. And you're going to use as an example. It would be a disaster. Yeah, true. One to wrap up our incredible conversation, I have one last question. And it's on this idea of gratitude letters. You have an entire section in your class lecture where you talk about the importance of writing thank you notes and gratitude emails to people in your lives. So if we're thinking about implementing this at what cadence do we write these emails and to whom? So this shri is my favorite assignment in winning writing. And by the way, for those of you who are teaching,

writing in any context, your challenge is not to get students who just use AI to do all the assignments. AI can't write a good gratitude note because it doesn't remember anything. that you remember. So a gratitude note, this is not the person who interviewed you for a job last week. It's somebody who helped you big time along the way, often long ago, like a middle school teacher who believed in you. Typically when we're in middle school, we're pretty clueless. So we're not going to think to write somebody a thank you note. But 15 years later, when you write that person, they are blown away. They are moved to tears,

to hilarious laughter. They're so grateful. They say, I've never received a note like this. And especially sometimes they're retired or they got laid off or things aren't going so well. And they get this out of the blue, and they're so very grateful. I wrote a piece on this for the New York Times

on writing gratitude notes. Nothing I've ever written has gotten such. a big reaction. So just to get you in the mood, I wanted to, I actually brought some of my favorite gratitude notes. I feel like writing gratitude notes is like oramaxing. Because you might ask, like, well, why would I write a gratitude note? Because it's going to take a lot of time and effort. And it's hard to craft those emails. You know, it's hard to write a good one that you feel proud of. But it's, it's aura maxing. It's karma. It's, it's for helping someone in a way that's free to you, I guess, just cost your time.

And that's the key. It's not just they who feel better. It's you who feel better, especially now. You know, the world is so angry and polarized. And there are so many people who just want to make other people miserable. And you feel so helpless. If you write a note of gratitude, you feel empowered. And here's some examples.

So here's one to a high school counselor. You drove me to my college orientation, which I would have otherwise missed. It was an eight-hour round trip for you on a single day in pouring rain, and you were heavily pregnant. You even ensured I had a ride back the following day. Two more, very short. This is to a woman who served in the military in Afghanistan. This is from a woman, to her commander. I remember vividly the first few days of your arrival at Bravo Company.

You dragged your desk out of your office and into the company. T-O-C. I saw it as a symbol of your engagement with the men and women under your command. And then finally, and this is my favorite to a violin teacher because the student is very funny. I apologize that this note is late, Mr. Violin Teacher, much as I was for most orchestra rehearsals. Thank you for pretending to believe me when I said I had practiced and for never complaining when I didn't shower between a basketball game and my lessons. While I should have learned more from you, your routines and patterns taught me a discipline that has shaped every facet of my life. And by the way, once people receive these letters, it often leads to a reunion.

This woman did get together with her violin teacher and a few other students for lunch. They sent me a photo. It makes life more special. I wrote for the assignment in class, I wrote my gratitude letter. I wrote two of them, one to my fourth grade elementary school teacher who really appreciated it and was just like, this is so random and lovely and I can't believe you remember me. And the second one I wrote to one of the people who wrote my GSB recommendation letter, which I was very grateful for. You want them to be this to be unexpected. That's what makes it so powerful. And so many people have said, I wept. I laughed. Thank you. I needed this. And how did you feel after you wrote those letters?

I felt great. I was reminiscing on the people who had changed my life. And I felt, I felt great. And I do have a gratitude letter for you that I will give you following this podcast conversation. But Glenn, thank you so much for joining us on Tiger Sisters podcast. It absolutely flew by. We learned so much from you. It's been a blast. My pleasure. You guys are cool. Glad to be here. And Glenn, for audience who's watching or listening to this, where can they find more of your teachings, your content, or anything cool you have coming up? So you can, oh, I just learned to say Google you implies that's what old people say.

So I think you could say, you can search up me on the web. And you can find it in various ways. And I will have a book coming out in a year, which distills. lessons from winning writing and also from my work at the New York Times. Incredible. Here's hoping that this episode helps get me into the book. Thank you so much. My pleasure.

If you guys enjoyed this episode, don't forget to like and subscribe to Tiger Sisters podcast because it helps other people find our podcast. And also, we have a newsletter. So find that link in the description and subscribe to our newsletter today. Thanks, Tiger fam. We'll see you next time. Bye. Thank you.