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Nicolas Toper: From Spam to Glam: Mastering Email Deliverability

Podcast

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About Nicolas Toper: Nicolas Toper is the Co-founder at Inboxbooster. His mission is to help email senders achieve better deliverability and avoid spam filters. With over 15 years of experience in web development, email technology, and cloud computing, he is passionate about creating innovative and scalable solutions for online communication. Before launching Inboxbooster, Nicolas founded and led CritSend, the first SMTP relay service that guaranteed email success. He also invented Pilo, a renewable energy battery that recharges when shaken. Nicolas holds multiple patents and certifications in computer science, and he graduated from Y Combinator and the Conservatoire National des Arts et Métiers. Fluent in French, German, and English, he enjoys sharing his insights and learnings in his newsletter. Check out the latest episode of our Conversational Selling podcast to learn more about Nicolas.

In this episode, Nancy and Nicolas discuss the following:

  • Nicolas’ story of getting into this business
  • Practical tips for email senders to achieve better deliverability and avoid spam filters
  • How to avoid getting important emails to spam
  • Gmail and Outlook practical insights
  • How long does it take to correct spam issues?
  • Why do emails from the same sender intermittently shift between my inbox and spam folder?

Key Takeaways: 

  • Ten years ago, sending emails was straightforward with clear rules, but today, it’s a complex and unclear landscape, creating a significant challenge for email senders.
  • Outlook wants your domain to have a good history, whereas Gmail doesn’t care about the IP and the domain, but they care about your users’ behavior.
  • If you’re doing cold emailing, you need to test your email on InboxBooster or another way once a week to ensure you don’t have any problems.

“ So, you have a free tool on our system, the InboxBooster, that tells you how to, analyzes your little list, and tells you where you’re emailing. Because if you’re emailing just on Gmail, it’s not the same thing as if you’re emailing on the form of two Fortune 500 companies, which is not the same thing if you’re emailing, so there is kind of because usually a lot of SMBs are using Outlook. Some other kinds of startups, lots of startups, are using Google Workspace. So, you really, the first step is really to investigate that. And until you know that it’s kind of, you will not be able to sound efficiently. ” – NICOLAS

“Email has become a bit of a puzzle lately, and let me break it down for you. A decade ago, sending emails was a breeze—clear rules, automated stuff, and personal messages. Fast forward to today, and the line between human and machine-generated emails is blurred, thanks to outreach tools like AdRage and Apollo. Cold emails, though less annoying than cold calls, face skepticism, especially from Google, which prefers ads. Now, onto a fixer-upper story about Y Combinator: despite its strong brand, it battled spam on Gmail. Why? They imported a MailChimp template, and some pruning oversight led them back to the promotion tab. We sorted it out, and they saw a 35% click boost. The lesson? Fixing email glitches is like solving a puzzle, sometimes iterative but worthwhile.” – NICOLAS

“Sometimes we have customers sending probably more than a couple of thousands of emails per day on cold average, and it’s working very well. So, it depends on what you’re selling. The key elements are as follows: First, you need to know who you sell to if you do cold average. You need to know: “OK, So this is my ICP,” and know those people will sell. And then what I’m saying usually is if you don’t know who your ICP is, you need to experiment until you figure it out, but you shouldn’t sell a lot of emails to be very careful. In deliverability, once you know who you’re selling to, you can sell a lot. And the second thing is sometimes because you care about who you’re selling to, so basically, what’s your revenue? There is another side to it, and I mentioned it: engagement. So, you want one unsubscription link. One clicks the unsubscription link, now it will be a requirement for Google. And the second thing you want is to be between 0.5 and 1.5 of the unsubscription rate. If you do that, you’re fine. This means that you have found a Via Negativa if that makes sense, your ICP. If you want people to unsubscribe a little bit because it’s a little bit trying to sell them some stuff and some are not going to be interested, then that’s fine, but you don’t want too many of them not to be interested because if you’re there, this means they don’t care, and you’re not emailing the right people.” – NICOLAS

Connect with Nicolas Toper:

Try Our Proven, 3-Step System, Guaranteeing Accountability and Transparency that Drives RESULTS by clicking on this link: https://oneofakindsales.com/call-center-in-a-box/

Connect with Nancy Calabrese: 

Voiceover: You’re listening to The Conversational Selling Podcast with Nancy Calabrese.

Nancy Calabrese: Hi everyone, it’s Nancy Calabrese and it’s time again for Conversational Selling, the podcast where sales leaders and business experts share what’s going on in sales and marketing today and it always starts with the human conversation. Today we’re speaking with Nicolas Toper, the CEO and co-founder of Inbox Booster, a platform that uses AI to ensure emails don’t end up in spam promotions on Gmail, Outlook, and Yahoo. The platform serves over 2,000 clients, including Y, Combinator, Zango, and Wisby, and has recently been featured in several articles, including Forbes, FIM, SMEs, and BusinessMall. Nicholas has a Master of Science in Computer Science and has been awarded four patents computer, compiler, optimization, and email, deliverability. Boy, that’s a mouthful, Nicholas. Welcome to the show!

Nicolas Toper: Thank you, thank you. [1:13]

Nancy Calabrese: I guess my first question is, how did you get involved in this business? And what’s the trick?

Nicolas Toper: So, first there is no trick and the second answer is it kind of happened randomly. I was studying and working at the same time and the people I was working with, the company I was working with, started to have email trouble and actually the teacher at my school was part of the team who built AOL’s fan feature so I kind of got some cheat codes here and that’s how I got super good person in my new company because I knew how these things worked just because I had the right connection and so that’s kind of how I got started and then I got real so it was initially just totally random and opportunistic and then I built a business in that space I sold it I worked in compilers afterwards, and then I also had my children, so I stopped working for a couple of years. And after moving to the US, I went back to it, mostly because the ecosystem has changed a lot, I feel, and not for the better. So, my point being that 10 years ago, it was very, it was straightforward to send emails and the rules were kind of simple. Now it’s basically a mess, as everybody knows, but besides being a mess, it’s very unclear. So, nobody really knows what’s working. [2:44]

Nancy Calabrese: Yeah.

Nicolas Toper: And a lot of people are selling like snake, all type of, oh, do this and that and it should work. But on top of that, the kind of playing film is very uneven. So, for instance, we’ve lost a customer recently because they raised a lot of funding and they had someone at Google at their board. So, Google told them that they wouldn’t be in spam. So, they donated us. So basically, if you know the right person or spend the right amount of money, then you will have certain advantages, and I just feel that’s wrong, and that’s also a good business opportunity. [3:20]

Nancy Calabrese: Wow. So, you are on a mission to help email senders achieve better deliverability and avoid spam filters. Give us some practical tips. How do we do that?

Nicolas Toper: So, first, the way to do that is actually… So yeah, as you mentioned, I’m on a mission, but this mission is mostly to explain how this thing works because the real problem you have right now is when you’re in spam, you have no clue why. And that’s kind of the problem because what we find out is if you’re in spam, and we explain that to people, in 90% of the time, they’ll do the right thing, and they fix their problem which is good for everybody because usually it’s because they’re sending better emails. That’s what usually that means. And so, the receipts are happier. The customer is happier because he’s selling more and it’s easily it’s more it’s easier. So, everybody’s kind of its kind of good for everybody. And there is 10 percent of the cases where they expect a magic trick. And so now, after I’ve contextualized this answer a little bit, the way to reach inbox, the first is deep. So, the first question is, who are you selling to? So where are you emailing to? So, you have a free tool on our system, the inbox booster that tells you how to, that will analyze your little list and will tell you where you’re emailing to. Because if you’re emailing just on Gmail, it’s not the same thing as if you’re emailing on the form of two Fortune 500 companies, which is not the same thing if you’re emailing, so there is kind of, because usually a lot of SMBs are using Outlook. Some other kind of, lots of, most startups are using Google Workspace. So, you really, the first step is really to investigate that. And until you know that it’s kind of, you will not be able to sound efficiently. And you’ll see that… [5:10]

 

Nancy Calabrese: Yeah. Well, why are they all different? I don’t understand.

Nicolas Toper: They all have their own inducing creases, so they all have their own quirks and way of working. So, for instance, Outlook, they really want your domain to have kind of a good history. Gmail, they don’t really care about the IP and the domain, but they really care about the behavior of your users. And other spam filters like for instance, Proofful, they’ll care about the age of the domain, they’ll care about a lot of factors. But for instance, if you look at what proof point, which is a spam filter used a lot for Fortune 500 and Gmail, they will classify spam. If you remove like the phishing email and all those things, the overlap is probably to be 25%. So that means 75% of your emails will be considered spam by let’s say one or the other spam filter, but there will be no overlap. So, you really need to be careful here. And that’s really the first step is, who are you emailing to? [6:11]

Nancy Calabrese: How long does it take to correct that?

Nicolas Toper: So usually, we can do that depending on what problems you have, but can take a day to a couple of weeks. And now once you know where you’re emailing to assuming, for instance, you’re emailing on Gmail, the first step is, are you in spam? For instance, I can use Proofpoint as an example or Gmail. But figuring it out is not that easy, because for Proofpoint, you need to buy this platform to figure it out, which we’ve done for you. And we share that information for free. Or, and even with Gmail, it’s very hard, because if you’re sending an email to your own Google Workspace account, Google is super smart that you want to receive that email, but that doesn’t mean that the rest of the world wants to receive it. So, you must use a specific way to even test if you’re in spam. So, the second step is, are you in spam? This you can do for free on Inbox Booster, and we’ll tell you if you’re in spam. Because what we do is we change, we have some test addresses that we change regularly. So, this way we know that they’re not getting trained, and they don’t learn what kind of emails our software would like to receive. So that’s kind of how we do it. And if you do it yourself, you can, but you need to create a test address almost each time you’re going to do test. So that’s roughly what we’ll do. So that’s the second step for you. So, before we can get to the inbox, the first question is which inbox? And the second question is, does it work? Now, assuming it doesn’t work, then same thing, you can use inbox booster and we’ll tell you why you’re interested, because there can be a lot of different reasons. And it starts to be very, very complicated. You really have two types of problems. The first one is it’s tied to your past behavior. So, for instance, you’ve sent emails to people you shouldn’t have, you shouldn’t have, or it has nothing to do with you, but it’s really like just a word that’s triggering the spam feature. And we’re going to tell you both and then you can fix it. If it’s a word, there is nothing to do, you just change the word and you’re there. So, for instance, we’ve had a customer, they were sending like a sign-up confirmation, and they were in spam. And that’s because they had a word tag in your HTML. So that’s the reason. And the second problem you’ll have, and for Google Develop, there’s going to be a lot of that. Well, it’s going to be a mix. It’s going to be also sometimes you’ve sent to the wrong person; you haven’t targeted well enough your email. And Google, if you’re sending to Google, they take that into account a lot. And they’ll assume that you’re not able to target. So, you’ll honor their users. So, to understand how Google works, the way they do it, they want people to like your email. To like meaning to engage with it, which means really to open the email, answer it, archive it, and search it without unsubscribing or deleting it without reading it. Or just reading it and deleting it or marking it as stuff. So that’s what you want to do, and if you’re able to do that, then there is no problem for sending on Google. On Outlook they care about similar things and proof points, they don’t really care too much about that. They care a lot more about certain keywords and all that. [9:26]

Nancy Calabrese: Why is it sometimes when I see, I’ll get from the same party the email in my inbox and other times it goes to spam? Why is that?

Nicolas Toper: Say that again, sorry.

Nancy Calabrese: So, let’s say you’re emailing me, and I’ve gotten your emails in my inbox, and then all of a sudden, your emails start going to my spam folder. Why is that?

Nicolas Toper: Oh, it’s the same principle either. It’s because I’ve sent you an email with a word or a part they don’t like at Google. Or I’m assuming you’re using Google. You’re using Google, right? [10:02]

Nancy Calabrese: Right. No, I use Outlook.

Nicolas Toper: OK, so Outlook is different. So, for Outlook, it’s because I have done so in most, so it’s almost the same thing. Sometimes because I have used a bad keyword like I’ve used, and those words changes all the time, so it’s very, so it’s kind of almost in real time. This is very uncommon with algorithms, I put a lot more with Gmail. What you will usually have been I would have sent bad emails afterwards, and because of that, I would put all my emails in spam. But Google is a little smarter, so they can just put a certain type of email. So, Google is going to do it like that so that is kind of the reason. So, it’s because of stuff I’ve done and in parallel, like for instance, I’m emailing you and at the same time I’ve sent a cold outreach campaign to people who absolutely don’t like my email and that’s what will happen. [11:09]

Nancy Calabrese: Wow. Is there a story the audience would find interesting?

Nicolas Toper: Oh, in email, yeah, of course. My story or in email deliverability story?

Nancy Calabrese: Any kind of story you want to tell.

Nicolas Toper: Ah, okay. So let me tell you the problem of email, before I talk about the story, I just want to explain why it’s starting to be a problem, because it used to be easier. The problem is 10 years ago, you really had automated emails, like newsletter, sign-ups, like a bank statement and all that. And then you had personal emails for business emails, like people that have been written by email that had been written by human. But now if you do called email, you’re probably using an outreach tool. You’re using AdRage, Apollo, whichever one of them. And those are automated emails. So, the kind of the line is blurry now. So, what’s an email being written by human? What’s an email being written by a machine? Nobody really knows. And I don’t usually want to receive an email. So that’s why this problem happened. And the reason also I think it’s important is because cold email is, first, it’s a lot less intrusive than cold calls, and two people need to sell. So, in some markets, this is how people expect to be sold for some products. So that’s kind of how you must do it. And it’s a good thing if you think about it. The main problem is Google is not very happy about that, because they would prefer you to pay some ads instead. That’s kind of the thing. And that’s the story. So, for instance, we fixed, you mentioned, a white combinator. So white combinator is not a company doing average. They don’t really care about that. They’re doing marketing. And they have a very, very high brand, a very good brand. It’s very powerful. So, they don’t really have deliverability problem. But they were still in spam on Gmail. They were in promotion in spam and Gmail for the Renewsator. And the reason? That’s kind of the interesting bit is the first one is because they re-imported their MailChimp template. So, they’ve imported, they used the MailChimp template, and they rebuilt it from that, but they kept some key elements of it. And that for Gmail was a very good predictor of promotion. So, they moved their newsletter into promotion. And the second reason they’ve had is, so we’ve did that, and it worked. But then they went back in promotion. [13:46]

Nancy Calabrese: Right.

Nicolas Toper: And the reason is because they haven’t, they never pruned their inactive users. In newsletter it’s important, meaning that some people haven’t opened their email in like maybe five years or clicked on anything, and they were still sounding to them. So, we fixed it and then the newsletter worked. And the information here and the story here is when I told them that, they were not very happy about the results the resolution we found were increased, their total number of click by 35%. But on top of that, what’s very interesting is this process is iterative. Like you had to fix it the first time, then you had to investigate it the second time. But after that, they had no problems. So, it kind of worked and they stopped paying us because they don’t have any problems. [14:37]

Nancy Calabrese: Right. Well, that’s not a good thing, is it?

Nicolas Toper: For us it is because it’s just a way of working with customers. We know that some customers will stay forever or a long time because it’s going to be a recurring problem. Most people don’t call Dimmers, usually. And for some others it’s just going to be like a one-time thing because they will not have any problems afterwards. And we can tell ahead because usually it’s email for you, business critical. Like will you be dead if your mail doesn’t work as a company or as a department? And usually, if the answer is yes, we usually have good customers. If the answer is no, usually it’s just a one-time event, but for us it’s still useful and it’s important to do it. So that’s kind of because it helps explain and all that. But what’s interesting in this story is one, the iterative nature of this kind of fix to do it a couple of times until you get there. And two, the second interesting element is that once it’s fixed, you really don’t have any problems in a lot of cases. And it’s the same thing with cold average, because one question I always have, it’s how many emails can I send? I’m proud to be your question list. And the answer is as many as the spam field lets you, meaning as many as you can with good engagement. [16:04]

Nancy Calabrese: Right.

Nicolas Toper: Sometimes we have customers, they’re sending probably more than a couple of thousands of emails per day in cold average and it’s working very, very well. So, it really depends on what you’re selling. And the key elements here are, and I’m kind of going a little bit outside of the initial discussion, it’s one, you need to know who you’re selling to if you do cold average. Very, very important. Like you need to know, okay, so this is my ICP and you need to know those people are actually going to sell. And then what I’m saying usually is if you don’t know who your ICP is, you need to experiment until you figure it out, but you shouldn’t sell a lot of emails to be very, very careful. And in deliverability, usually once you know who you’re selling to, you can sell a lot. And the second thing is sometimes because you care about who you’re selling to, so basically what’s your revenue, there is another side to it, and I mentioned it, it’s engagement. So, you want one unsubscription link. One clicks unsubscription link, now it’s going to be a requirement for Google. And the second thing you want is you want to be between 0.5 and 1.5 of unsubscription rate. If you do that, you’re fine. This means that you have found a vial negativa, if that makes sense, your ICP. Because you want people to unsubscribe a little bit, because it’s a little bit trying to sell them some stuff to them and some are not going to be interested, then that’s fine, but you don’t want too many of them to not be interested because if you’re there, this means they don’t care and you’re not emailing the right people. So, you want to, yeah. [17:45]

Nancy Calabrese: Right, okay. How many emails is it safe to send out a day?

Nicolas Toper: Again, as I mentioned, there is no limit if you’re able to reach this pattern. If you’re able to reach those KPI, you can sound as many as you want.

Nancy Calabrese: Well, hey, I can’t believe we’re up with time. What is the one takeaway you want to leave the audience with?

Nicolas Toper: that you absolutely need to test your email. If you’re doing cold email, you need to do that on InboxBooster or do it yourself, but you need to do it once per week just to make sure you don’t have any problems. Because there is another problem, because I can talk about this subject for hours, but it’s very, very important to test your email. That’s kind of, that like really, this is kind of the stats I mentioned. And even if you don’t think you have a problem, you need to do that, you need to check where you’re emailing to, like what mail server is behind it, and two, do you have a problem? Because the thing about this kind of thing is it’s not to compound, so if you wait too long, not only you will lose sales, but you might lose your whole mailbox. So, you must be very, very careful here if you start to see a problem. It’s kind of like a leak when you have a water leak in your home. You don’t usually want to wait too long. This is the same type of thing.  It’s kind of just a problem that kind of explodes if you don’t take care of it. And so, you absolutely want to check that regularly to make sure you don’t have a problem. And you can do that for free. So that’s kind of… And it’s very, very important. [19:22]

Nancy Calabrese: Wow. Cool. So how can my audience find you?

Nicolas Toper: So, they go on Inbox Booster and they can even book a meeting with me on the website. They can also test it for free if their email is in Inbox.

Nancy Calabrese: Cool, cool. You know, folks, we all live in email land. You’ve got an expert here. And I know for me, without having this discussion that Nicolas, I had no idea, no idea. So, thanks so much for being on the show. And for all of you, I strongly suggest that you reach out and you have that offer, right? You could do some free emails. Isn’t that what you said?

Nicolas Toper: Yes, that’s correct. They can test for free; they can test and again we’re happy to do that for free, there is no problem. And they will even get some diagnosis if they have a problem. And there’s no need to sign up or anything, it’s just on the homepage. [20:16]

Nancy Calabrese: Awesome. Love it. So here we go. Another fabulous conversation with an expert in what we all need to be better in. I wish you all a great sales day. And Nicholas, thanks so much for being on the show.

Nicolas Toper: Thank you. [20:32]