Today on The Startup Chat, Steli and Hiten talk about email newsletters and why it’s important to your startup.

In this day and age of social media, does email marketing still work? According to Steli and Hiten, the answer is yes and if you’re not sending out newsletters in your startup, you are missing out on a huge opportunity to connect with your audience and grow your business.

In this episode, Steli and Hiten talk about newsletters, the value of them and why you should be emailing your mailing list consistently and much more.

Time Stamped Show Notes:

00:00 – About today’s topic.

00:28 – Why we’re talking about today’s topic.

01:14 – Steli talks about one of his favorite Hiten Shaw quotes.

01:45 – Hiten talks about what great email is and tools you can use.

05:19 – Steli dives into what one-to-many emailing is.

07:41 – How to do newsletters the right way.

11:06 – Hiten gives a great tip on how to improve your email.

12:13 – Steli talks about how you should consume the emails that you receive.

14:00 – How to improve the content of the emails you send.

15:17 – Why editing helps take your emails from good to great.

18:31 – Hiten suggests how you can improve your emails if you’re struggling and putting in the work.


  • Good email is dead, great email more alive than ever.
  • If you write great email, you’re gonna be crushing it.
  • Learn how to tell a great story.


Steli Efti: Hey everybody this is Steli Efti.


Hiten Shah: And this is Hiten Shah and today, on the startup chat, we’re actually gonna talk about one of the most boring topics out there. And that topic is email. Were not talking about the Gmail you use, and the emails coming in your inbox, although we kinda are. We’re talking about the emails that you actually send.


Steli Efti: Yeah


Hiten Shah: And this is like, whatever you would call a newsletter. We’ve talked about this thing in the past about the value of them and things like that, today’s episode we actually want to double down, dig in deeper and talk more about kind of where we are at right now. You know and answer the stupid question, which is does email still work? Which I think we’ve answered before but I wanted to start a little light-weight. Yes, email does work. Yes, if you are a business of any kind, you should be emailing people.


Steli Efti: Boom. And then, I will double click on one of my favorite all time Hiten Shah quotes on the topic of email, which was, so good email, people say email is dead and all that crap, good email might be in trouble, great email is more well in the life today than ever before. If you write great email your going to be crushing it for your business.


Hiten Shah: Good email is dead.


Steli Efti: There you go.


Hiten Shah: Great email is more alive than ever.


Steli Efti: Boom.


Hiten Shah: Just to paraphrase a little differently, I don’t remember how I said it, thank you for that reminder. I almost forgot I said that. I don’t think we talked about what great email is. Did we?


Steli Efti: Let’s talk about it.


Hiten Shah: Okay. So well one, great email is using a great email tool. Let’s just start there.


Steli Efti: Alright.


Hiten Shah: I know there are a lot of them out them, and we don’t really necessarily promote one or another, but I am going to speak about it for a few seconds. There are tools like MailChimp. MailChimp is actually a very good tool. I do use it. They are not paying me to say that because I use it and I love it for my email newsletter. I also use SendGrid at my companies because we need to do transactional email that are more programatic and MailChimp’s features around that are less mature, at least in my experience, than SendGrid’s. So when an engineering team needs to mess with email, or a product team, we tend to use SendGrid and make it more programmatic if you need to program around it and things like that. That being said, SendGrid’s campaign management tools are nowhere near Mailchimp’s. And then we have a lot of the advanced category such as Campaign Monitor, which is a little more advanced in some areas, or Infusionsoft, which lets you do a bunch of drip campaigns and things like that; I kind of wanted to get the tools out of the way Steli because I think it’s important, because we have a lot more to say on this. And then another kind of new set of tools would be tools like Drift and Intercom, which are chat plus email, and they let you do chat and email, and the folks at Drift have actually started to connect the two in really powerful ways. The folks at Intercom kind of started that trend by saying your emails and your chats sit in one place. And now, even Zendesk has a lot of emailing, not for marketing purposes, but for chat and email they kind of try and combine that from a support standpoint. And then, of course, there’s Front. Front allows you to have a shared inbox and lets you take one email address like, and share all those emails and manage them across multiple people. So, the category is huge, there’s a lot of email tools, I just spit out a bunch of use cases and a bunch of different tools.


Steli Efti: Hot fire.


Hiten Shah: Got that out of the way … Yeah? What’s up?


Steli Efti: I just said hot fire, you’re just like on a roll.


Hiten Shah: Heck yeah, I’m like an encyclopedia for some of these tools man.


Steli Efti: Yeah.


Hiten Shah: I’ve probably used all of them or have some kind of visibility into how people are using these tools, and I think email tools are amazing, and it’s one of the tried and true software. So on that note, I have to mention one more, is that okay?


Steli Efti: Yeah, go.


Hiten Shah: Mixmax. I think Mixmax is one of the most powerful email tools out there today. The reason is, it’s a Chrome extension and not, as long as you connect with your Google account, and you can send email and do lots of fancy things, like put a presentation right in the email, or set up fancy drip campaigns, or send bulk email through Gmail, and all you need is your Gmail and Mixmax and you’re off to the races. They also, one of my favorite things as we talked about in a previous episode, they’re a freemium business, they have a very generous free plan, and I’m a huge fan of that product as well. Again, none of these have paid me to say this, and I just got to spit it out, because these are all great products; And, one of the biggest questions Steli, about most of these categories that we talk about when it comes to software and tactics is what tool should I use? What tool should I use Steli? So you know what? We got that shit out of the way.


Steli Efti: There you go, boom. Check mark behind it. So the focus here is obviously not on one on one email, although a lot of principles that we’re going to discuss are universal, as we usually like to do, but this is about company email, one to many, typically. Back in the day the prototypical golden standard of one to many corporate email, or b2b email was the newsletter, quote unquote. The generic email that a company would send to all their customers, all the contacts they had in the contact database, informing them about all the great news there is: industry news, company news, any kind of news that might be interesting to the recipients. Today, I do see the traditional newsletter dying off. We still call that one to many thing, we typically call it a newsletter in the b2b context, but it’s not a newsletter in the traditional sense. You have newsletter, but it’s not really a newsletter, it’s not like a beautifully formatted html email with lots of news in there. It’s typically a very in depth, detailed story or strategy or learning that you share with people that have given you their email because they want to learn more about product and product development, that’s the newsletter you have on product habits. It’s called newsletter because it’s an email list, and they’re all receiving the same email at the same time, but it’s not really that outdated format of just having 8 different stories or news items or things in there. It is something very different, and more modern, and more focused for creating value for the recipient. You have an email at times, where you share different top articles that you find, there’s all these kind of articles that you read, you read a shit ton and are one of the best curators of content on the web and alive today, and so you curate an insane amount of content down to the best pieces of content that people could find in the b2b space, usually, and set it up. But again, it’s not really a newsletter in the traditional sense, and I want to talk about the one to many email that really moves the needle today, that really crushes it for businesses, for brands, delivers value to the recipient but also delivers or creates a ton of value for the sender, doesn’t matter who that is. So what are we seeing today that is really great … I don’t know, great newsletters or great one to many emails, I don’t know how to call this, but we’ll just use newsletters as a commonly used and understood term. What’s presently a way to do this in a great way, not just send out these bullshit, outdated corporate newsletters, which I see less and less; And we still did, we made that cardinal sin until nine months ago, we were sending these monthly generic emails, which I now am ashamed for, but we’ve changed our format drastically, and I want to talk about that with you. What you see, what’s working, what you do, what we do, and hopefully people can learn from that and utilize that.


Hiten Shah: Yeah, I … You know, I get so many questions about email now, it’s funny I get questions about email from people who are paying attention. And people who aren’t, I don’t get any questions from them. And I think that’s the first step … I don’t think you can write great email without being able to criticize other people’s emails. So the first step I would use is start asking people what their favorite email newsletters are, and sign up for those. And try to just understand what those people are doing. I promise I will say what patterns I have noticed, and why I write the way I do on email, and have spent a lot of time, especially in the last years learning how to do that myself. But the biggest thing is in your category, even if it’s not a great email, sign up for those too. So first thing is sign up for email lists that people say are great, because that’s word of mouth, right?


Steli Efti: Yeah.


Hiten Shah: So I think that’s great. Second, sign up for emails in your category, in your space, about your topic. I do that all the time, continuously. I sign up for so many I even have a separate Gmail account where I sign up for them, and I always get a ton of value just by looking at how other people are writing it, and also, honestly, being hypercritical of those emails. I have even friends that I’ll email and say “Hey this was a real shitty email, here’s why” if I know they’re in the category and someone’s written an email in their category. Or I’ll say “Hey this was a great email,” so I think you can even, if you want to go further you can even create a group of people that value sending email and kind of do that back and forth; It’s really powerful to get other people’s perspective and their viewpoint on how an email made them feel. I know I almost sound ridiculous, because this is a lot of depth on email, but if you want to write great email you have to be able to criticize email, and other people’s email. It’s one of the skills that I don’t see many people going after and getting better at. Emailing as well as just being able to criticize. The reason I say that is because the majority of writing is about editing, not about creating.


Steli Efti: Yep.


Hiten Shah: Right? So that’s why they say, just write. Yeah, I agree, just fucking write. And then start editing, and spend more of your time editing. You can’t do that unless you read … You know what, the way to get better at editing is by reading all the writing out there, and being able to critique it. And yeah, be an asshole. Talk about the stuff you didn’t like about it, really internalize what a great email feels like. That’s my biggest sort of perspective on email. The biggest tip I would give people is learn how to tell a great story. What I mean by great story is a story that is compelling to other people. If you just do that, and get good at that by email, you will do more than what most people are able to do when they write an email. They can’t tell a story. If you look at all the great people that are writing great emails today, storytelling is the number one reason their emails are great. That’s it. That’s what I got, on great email.


Steli Efti: Yeah, I was just thinking about this. I agree with you so much that I try to disagree with you at times, but I could not think of a single example …


Hiten Shah: Bring it.


Steli Efti: No. I could not think of a single example of the type of people … I can’t count the people or the companies in one hand … I don’t know if it’s six or seven, but it’s definitely not ten. So in less than two hands I can count on how many companies are sending great emails. And through those, I was parsing through my head, are any of them sending … Can I think of an awesome or great email that was not an example for great storytelling, and I can’t. I really can’t come up with that. So I think that storytelling is a really big part of that and editing is a really big part of that, so being a conscious consumer of email … We all consume a shit ton of email, but if you are in business and you are trying to build a business, and build a startup, and build a company, and grow it, you can’t just be a mindless consumer of email. You need to become a conscious consumer of email. You need to be looking at the emails that resonate with you, that make you respond, and you need to realize why. Why is that? Why do I like this, versus not that? Why am I not reading this? Why am I looking at this email and going “Oh my god this is so stupid,” what made me think and feel that way? And then you need to take note of these things and when you send email you need to run them through the query and go “Do I make the same dumb mistakes?” or “Are we making the same stupid mistakes as somebody else?” or “are we using the same awesome tactic of storytelling?” or “Shit, we have a really great piece of content here, but the email is not really great storytelling, how can we pull out a story and highlight that or tell the story better or make it more compelling for the reader to want to read more, want to read what we’ve sent to them?” I think that my one simple advice when it comes to one to many email is that although you might send some emails in bulk and to many people at once, the day of writing emails, filling it with lots and lots of disconnected content to hopefully have some piece of content in that email that will be compelling to some people on that email list that you’re sending out to … That kind of high quantity low quality approach is dead. That’s not going to work. So you need to start asking yourself “How can I write one story, or one piece of content that is so good it’s worth sending to everybody at once? That’s so compelling I think most people that I’m sending it to, even if it’s a big list, will love it, will read it, will get value out of it.” That’s the right mindset, it’s all about empathy, and its all about trying to understand even if it’s a big group of people, what is the common denominator; what is something that even two hundred thousand, five hundred thousand, a million people on an email list … What is the type of story or content that these people all will probably enjoy, because they all have something in common? Otherwise, they would not be on your email list, hopefully, right? There’s some commonality that needs to be there. If you take that kind of empathetic approach you can be … You can write great email and you can see amazing success. Our email list is a massive driver for our business, and there’s not a single day, seriously, there’s not a single day in the week, weekends included, where I don’t get multiple emails from people telling me … Thanking me for an email that we’ve sent them, and saying that …


Hiten Shah: Wow, that’s amazing.


Steli Efti: Seriously, like the …


Hiten Shah: Yeah, same here.


Steli Efti: Every day, and I know that you are getting this as well, I can assume that people are telling me that the emails we send out, “Steli the emails you guys are send out are my favorite emails, one of my favorite emails, I read them, I don’t read any other newsletters or any other emails I’m getting from other companies, but I always read yours. It’s always valuable, it has helped me x, y, z … ” The amount of value you can create if you do email great, the amount of business that can drive to you, is really tremendous and we are really a big example of that. But you’re going to have to put in the work, you have to put in the work. You have to see what others do and what works. You have to learn how to do storytelling. You have to … You can’t just send out emails … You said something about editing.


Hiten Shah: Yeah.


Steli Efti: Great writing is really great editing. There needs to be a kernel in there, like some good story, some good idea, something valuable, but then what makes the writing great is going to be the editing. Not in the writing part, once you have something, in the taking things away, and restructuring things, and rewording things, and working on the structure, and that’s … If you do the editing part well, and if you invest in … That’s really going to take good writing to great writing, or good emails to great emails. I was just reminded when you were saying this that every Thursday, Ramin who you know, who is working with us on the podcast, he’s like the invisible man in the background who helps organize a lot of things around The Startup Chat, big shout out to Ramin. He works with me in marketing at close, and on Thursdays I always get a first draft version of the Monday morning email that we send out. Monday always we send out to our email the most important piece of content that we’ve created. There’s always some back and forth between him, and myself and other people on the team … Editing the subject lie. Editing small parts of it … It’s a collaborative effort in the final mile, the Thursday/Friday before Monday comes is where really what we’ve created as a first version becomes a great email that people open, read, respond, click on and thank us for. So make sure that you have a group of people that help you on the editing part, to help you push a good email all the way up to a great one, and really invest in email. Great email is really well and alive as a very wise man once said. Most companies, think about it, I am consuming content all day long, Hiten is like this … The amount of company, the amount of email newsletters I’ve subscribed to and companies that have me on their newsletters is probably thousands and thousands of companies. And there is maybe six or so that I appreciate, that write really great emails. Six, out of thousands.


Hiten Shah: Wow, yeah.


Steli Efti: So putting that extra work in to become one of that one company in your industry that really is killing it with the emails, that can be a determining factor for a lot of success. It really is worth it.


Hiten Shah: It’s absolutely possible.


Steli Efti: Yeah.


Hiten Shah: Yeah. You’re right.


Steli Efti: Awesome.


Hiten Shah: Okay. So if you’re struggling with email, and you’re willing to put in the work, email us, and we will help you. We’ll point you in the right direction. You have to be willing to put in the work. It’s Steli, S-T-E-L-I at or hnshah, H-N-S-H-A-H, which is also my twitter handle, at, and we would love to help you out. We want to see people write great email and especially people who are willing to do the work. But it takes work, real work, I spent a lot of the time last year doing this work and it’s not easy, and I know you have to.


Steli Efti: Yeah, and if you guys are committed, even if just one of you sends us an email and shows us what their doing and is willing to work with us and take our feedback on board to take their okay or good emails to great emails, we will not stop until we’ve helped you write great emails and see a lot more success with it.


Hiten Shah: Absolutely.


Steli Efti: Alright, that’s it from us, we’re looking forward to hear you. Bye bye.


Hiten Shah: Bye.