Profiting from bad email deliverability

The clearest line to a business success is solving big pain. That’s what Benny Rubin did., optimizes email deliverability for businesses. You’ll hear how he came up with his business idea, how he got clients, why he left the business and why he’s back. And Benny will give you some suggestions for getting better results from your email campaigns.

Benny Rubin

Benny Rubin

Benny Rubin is the founder of, which specializes in email deliverability solutions, focusing on technical service and scalable business growth.


Full Interview Transcript

Andrew Warner: Hey there, Freedom Fighters. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses. This is a really interesting business that we’re going to find out about today. Benny Rubin realized that email deliverability is a pain.

Now, most of us, when we can’t get our email out, we think, oh, I screwed up. Why is my email system not allowing me to email out, but they’re allowing everyone else? It must be because the mail that I sent out stinks and we just deal with it in shame. And this guy comes out and says, you know what?

This is an actual business here. If enough people have this problem, I think I could create a service where I fix it for them. And because email deliverability is directly correlated with profits for businesses, there’s no question about how much I could deliver, an upside for them, killer, let’s stop everything.

Let’s build this business. And he did the business is called senders. The website we were talking about, maybe he needs to change it because it’s senders. co, right?

Benny Rubin: That’s right. Senders. co.

Andrew Warner: Senders. co and I want to find out how he did this and I can thanks to a company that I love and it sounds like He loves it too and so many of my guests do no goofing around here Gusto is a great the best way to pay your people unless you’re like an ipo company We’ve seen people use them until they go to ipo and then they say I switched I get it If you’re not ipo if you haven’t gone public Go to gusto.

com slash Mixergy. All right, Benny, revenue. How much are you doing right now?

Benny Rubin: Uh, so we’ve gone up and we’ve gone a little bit down and then we’ve gone back up as all entrepreneurs listening. There’s no, that story. We met through a big transition over the last couple of months and through the transition, we had to shed some of our old revenue from the agency style business that we were running, and now we’re doing more of the technical service side.

So now we’re bringing it back up, but definitely in the millions. definitely haven’t hit my goals of getting to 5 million and beyond, but if all things go well, maybe we can get there.

Andrew Warner: Okay. I don’t fully understand this. I thought it was all a service business. I pay your people, your people go into my software, whatever it is, Infusionsoft, ConvertKit, even if it’s some of these direct mail systems that send out, those cold emails and you handle it. Isn’t that the service? Is it more than that?

Benny Rubin: Well, there’s layers to the way. Email functions. Basically, email, as we all know it, is a bundle of four different things, or maybe five things, depending on the way you think about it. There’s domains, like Mixergy. com is a domain. There’s an email address associated with the domain. There are IP addresses, which most people listening to this go, Yeah, yeah, I think that’s something that happens on the backend.

I don’t ever think about it. But there are IP addresses that are actually the sort of thing that’s delivering the mail to the internet and sending it off. Then there’s your DNS, which is the bits of code on the back of the website to say what’s going on with things. That’s where email authentication happens.

Maybe you’ve heard of SPF, DMARC, DKIM, that kind of stuff. And then the fourth side is. a sort of more abstract thing, but it’s actually not, which is like the ratio, like how are your emails actually doing once they go out? And that ratio covers many, many things. What’s the text to HTML ratio inside your email?

What is the number of emails that are going to be open versus not open? What is the number of them that are going to spam versus not going to spam? How many of them are being unsubscribed? All these things factor into ratio. And then the last one maybe is content, like what’s in the email itself. Does that generally make sense?

So what our team is doing is looking across all of these and trying to figure out how to optimize them for our clients, many of whom are sending cold emails and many of whom are sending regular consumer or newsletter style emails.

Andrew Warner: Okay. Those cold emails are the ones that we get from people who will like, say for me, I

love your podcast, been listening forever. Can I get my guest on? Or I noticed that you use, click funnels. We have this tool that works with click funnels. Do you want to talk to someone? All

Benny Rubin: Yeah. Those are cold emails. Yeah. And those are the hardest ones. Those are the ones that create the most issues. And most of our clients these days are people that are saying, Hey, we used to do cold emails in this way. Now it’s gotten weird. Can you help fix it? And this is where the technical part comes in.

We actually. Maintain IP addresses, which is the second thing I mentioned. You remember domains, IP addresses on behalf of our clients, and that is highly technical and you can automate parts of it, but it’s really, it’s still really service oriented, but it’s also not dissimilar to what, other larger service providers have to do in order to maintain email sending and quality.

Andrew Warner: Alright

Before we get into the business and how you built it. And where it’s going, you took some time off, which tells me the business was doing well, you were probably cashing out. You were maybe a little burned out from working. You seem like a guy who’s been an entrepreneur his whole life. what did you do in that time that you were taken off?

Benny Rubin: Well, I think it’s kind of funny because I mean, I think business is, it’s supposed to be fun and it’s supposed to be funny. And the reason why business is such an exciting thing to be involved with is not because of the rewards in the future for it. Although we tend to fixate on those things, like how much revenue do you generate, things like that.

I think what makes business fun is that it’s sort of a rules based. Simulation in a way, for example, all of our clients choose every month, if they want to keep working with us or not, that’s not really how it works with your neighbors. You don’t just get to choose. Oh, I don’t want you to be my neighbor anymore, unless you’re going to move yourself.

You don’t get to do that with family. Almost everything that really is sort of intensely matters in your life. You can’t really just be like, this was a great relationship till now, but my needs have changed. Goodbye. So I sort of enjoy those aspects of business. That said, in order to build a robust business, as you know, and I mean, how many interviews have you done now?

Andrew Warner: Yeah. Thousands.

Benny Rubin: Thousands. The repetition is how you build strength and how you build businesses. When people come to me, I’m sure you get this too, people either come to you for like one off mentorship sessions or you sort of have a relationship over time. Nine times out of ten, I’m just like, you just haven’t had enough at bats.

That’s why you don’t really know what’s up. You just haven’t had enough at bats. So I did so many at bats because I built this single handedly. I mean, I had a small team of people or whatever, but probably passed 2 million in ARR doing a hundred percent of sales meetings, myself, a hundred percent onboarding myself, and not thinking, well, I’m at 20 K or 30 K or 40 This is the time where now I can pass it off to a salesperson.

So when I finally was able to pass off almost all the key functions. And it was like April of, I don’t remember what year it was now, but April of 2022 maybe. What, what year are we now? 22. Yeah, 2022.

Andrew Warner: Yeah. So 22. Okay.

Benny Rubin: 2022. I just said, I kind of had one of those things where all the email traffic died down and I was just like, okay, great.

Now I have to figure out how to live. So I did the normal things. I did more traveling. I

Andrew Warner: Meaning, you had already, you, you, you did your at bats, you got good at cells, and then you systemize it, you pass it on to other people, they were running it, and eventually, over time, you were getting called in less and less, the system was running, and you said, you know what, now I need to figure out how to live.

And the reason you didn’t know how to live was, what was your life like? Was it like mine, where you were working constantly?

Benny Rubin: Um, yeah.

Andrew Warner: Yeah. Okay,

Benny Rubin: Keep in mind, I don’t, I don’t have the, one of the beautiful things about work is that it can fill any amount of time you need it to. There are a lot of things in life that don’t really work like that. You might love television, but after like, watching two or three in a row, like I’m kind of done, right?

with work, it’s so dynamic and there’s so many things you can do with it. So you can really pour a lot into it. I estimate, I’d have to run the numbers for real, but we can, we can be generous with my estimation. I estimate that to get to $2 million in a RR with my business and my business model I was doing at the time took me maybe 1000 hours of FaceTime with potential clients. So that’s, I, I speak Japanese, I learned Japanese, I went to school in Japan. I estimate that I spent maybe two to 3000 hours learning Japanese to the level of fluency that I achieved. I play the violin. I play the viola. I went to music school. I made a degree in music. I probably spent two or 3, 000 hours practicing the viola.

So to do a 1000 hour investment in a relatively short amount of time, that’s an incredible amount of time. And I know some people can do this for years. I’m just not that, not that strong. I just didn’t have that. So after around a thousand hours of getting it to this point, I kind of looked around and was like, wow, it’s not so bad that you invest the time, but you become a one pattern person.

And I kind of needed. To, to figure out if I was going to be a multi pattern person or one pattern person, or what else was kind of available and going on,

Andrew Warner: and so you took time

Benny Rubin: because that’s a very thorough answer.

Andrew Warner: What’d you do in the time off?

Benny Rubin: well, I did a lot of nothing. I did a lot of travel, some traveling. I did some thinking. I talked a lot with my friends.

I played a lot of music. I hung out. I also helped my team. I, you know, I was available for my team when they needed it. But I think I expected some sort of lightning strike to happen. Like, aha, running an agency that helps other businesses grow. That’s not my calling. Actually, I should be, but it didn’t quite happen like that.

My wife teases me about that because she just thinks it’s funny that I sort of expected something to happen, but nothing really happened, something could have happened, but it didn’t. So I, I kind of, uh. Ended up coming back and the terms of me coming back and all the things are a slightly different conversation.


Andrew Warner: And partially you came back because email’s going through a difficult period, especially the kind of email that you work on and you need to come back and help steer the ship. All right, let’s come back to this. Take me to the beginning. How’d you know this was an issue that you had to get into business to solve?

Benny Rubin: in 2020, we’d already been running an agency for four years, helping companies grow their cold email outbound,

Andrew Warner: By doing cold email outbound for them.

Benny Rubin: Yeah. Doing cold email outbound for them. Just standard cold email outbound agency. Everyone’s cycled through them.

Andrew Warner: Today it’s pretty common. There was a period when it wasn’t. Today it’s fairly common. You hire people and all they do is they write out email and they send it out on your behalf. And then when there’s someone who responds, they pass it on to a salesperson who deals with the,with the customer.

Great. Okay.

Benny Rubin: well, I’d been doing cold email since 2013, 2014, 2016. I turned it to a business. There was maybe five or 10 other agencies that you could sort of point at and name at the time. Now there’s probably a thousand. It’s okay. It evolves, things change. What changed is Google decided to start imposing their, acceptable use policy. The first term of the acceptable use policy is thou shalt not use this for cold email or unsolicited bulk email or whatever language they want to use. And they sort of didn’t really mind so much. Things changed. They started to clamp down, which meant that in the olden days, you could. Spin up an Apollo.

io account, spin up an Outreach. io account, plug an email in your regular corporate email and start sending no problems. Now that started to be a problem. Now we had solved that problem in 2020, but almost none of our peers and none of the SVPs of sales and all these SBDR leaders had even thought about this problem.

So when this started to become a serious problem, maybe about a year ago, half a year ago, we were in pole position to. People solve this for themselves. And that’s the reason why I came back and I

Andrew Warner: Because you had a solution that was better than others. Okay. I get it. But let me pause here for a second. I used to have people come into my office who were doing this kind of. Basically cold email, some would call it spam where they were sending out emails. And as soon as there was a response, they’d get on a sales call with that prospect, a lot of them were using fake email addresses from Gmail.

They were just cycling through a bunch of them. And I still see that happening. Is that not the way that they, that people do things or they would get a. a new domain and do it. And are you saying that sometime in the early to 2020s that stopped working?

Benny Rubin: Well, let, I mean, I, I know Gusto is a sponsor, so we can talk about, ancient history. One of the companies that truly built a billion dollar business through cold email and cold email loan famously is Zenefits.

Andrew Warner: Mm

Benny Rubin: So what Zenefits did was they said, Hey. There’s a million businesses or whatever the number is that matter.

We’re going to cold email all of them. They were cold emailing from Zenefits. com or something similar, maybe a subdomain or something, but they’re emailing them from Zenefits and, the founder of Zenefits who moved on, started another company that did something very similar called Rippling. They’re also built, I get cold emails from them all the time.

They’re very, very aggressive with this. So we’re not talking about. some sort of offshore HR dev service that’s sent to you from a Gmail account. You’re getting these emails from the corporate company, the corporate entity. It’s a valid business. They’re doing a valid pitch. It’s from a real person.

They’re saying, Hey, Andrew, this is our value proposition. Are you interested in potentially

Andrew Warner: hmm. So these aren’t the people who are coming over for scotch night at my office and we’re cycling through gmail addresses. They’re using their real email addresses. They’re reaching businesses. Okay. But when you started, you saw a problem. What did the problem look like back in 2016? when you launched senders, but

Benny Rubin: So launching senders was the process for running, setting up and running cold email is very difficult. Fast forward to 2020, even just getting emails sent. Became, whoa, we can’t

Andrew Warner: you, you keep asking me and I want to go back.

Benny Rubin: us.

Andrew Warner: Don’t fast forward me. Take me back to the beginning. What I want to see is. How you saw this problem when a lot of other people were in the business and they were on the most clever side, spinning up 50 different Gmail addresses and thinking they solved it.

And you saw, no, this is a problem that I could build a real business in. What was that?

Benny Rubin: Well, most, most of my friends ran SAS businesses in 2016. So that’s, this is sort of something important that I always end up bumping against. Founder. Market or founder product fit is really important. It’s a really a thing. I could not do what you do. If we swap places, I’d be gone. I’d be like, that was cool.

Bye. I can’t interview people all the time. And they don’t have that. I don’t have that level of empathy. When I, I had a business before Senders that was a software business and we did not get very far. However, we made a lot of friends that were entrepreneurs. We did a very prominent accelerator.

We did very well with our peers. So when I decided to shut down. senders I turned to all my founder friends and I said, Hey, what do you guys, what’s going on at your company that you can’t really crack the code with internally that you want help with? And a bunch of them said like, look, cold emails, this kind of weird jank thing that’s like, uh, we don’t really like it.

We don’t, it’s not, it doesn’t really work in the way we need it to. We want someone like you. Cause we know you’re going to, you focus on it and obsess on it. So that’s how I started a cold deal email up on agency at all. It was sort of like by popular demand. So to speak, if they had said, Hey, we have a design problem.

I would have been like, okay, I’ll find a creative director. let me figure out how to, you know,

Andrew Warner: Okay. So you went to them, you said, what’s a problem that you have that you can’t. you looked at the ones that made sense to you. And you said, okay, this is one that’s close. I could do it. What was the first solution? Like, what did it look like? What did you create for them?

Benny Rubin: All out of box software, Gmail accounts, all the standard stuff that you imagine, not Gmail in the sense of it’s like a gmail. com, but using their Google workspace accounts, Hey, spin me up three new email addresses. We’ll plug it into. Reply. io and we’ll write some emails that we think approximates something good and go from there.

Andrew Warner: And the issue that they were having was not just that they weren’t getting email sent out. It was also, they didn’t know what to send. Is that right? They just wanted

Benny Rubin: Yeah. That’s all. That’s how it always is. Yeah. early with all marketing stuff, people go, Hey, we hear that people can do this well with email, but what do we say? What’s weird? How do we handle all these? what does this reply mean? Really? You know, like that kind of stuff. I mean, there’s, it’s a, it’s a whole world of, of a specific kind of.

Mentality to really

Andrew Warner: And it’s a lot of writing. It’s a

lot of, a lot of writing, a lot of if then solutions, a lot of thoughts about followup, and there’s the tech issue you were doing. You were doing all the work yourself in these early days.

Benny Rubin: in the early days for many, for a long time, I had one assistant style person.

Andrew Warner: Okay. And then it was you doing it. A lot of your friends. How did you then get the next batch of customers? I’m assuming you were cold emailing, right?

Benny Rubin: I did a lot of cold email for cold email, and I get a lot of customers that way. But also what I found a very specific kind of referral would come, a kind of referral I didn’t know existed. I was getting referrals even from clients that my solutions weren’t working for.

Andrew Warner: Okay.

Benny Rubin: if you read the text of the emails, well, if it works, it works.

And they go, Hey, Ben, he’s great. He helped me do this and you should work with him. I think that there’s a kind of referral that I didn’t know existed, but it’s purely an operational excellence


The emails would say, Hey, blah, I’m introducing you to Benny. He got me spun up with solution for this really, really fast, really efficiently.

It didn’t quite work for me, but, and it’s like, Oh, wow. Okay. So you can win even if you fail, if you’re very earnest and you close loops with clients and you communicate very thoroughly and very transparently. And that’s a lesson that I’ve tried to carry through. All the way through. When you, lack on transparency, when you lack on that kind of stuff, you, you sort of business can’t really grow in the same way.

Andrew Warner: did you ask them for those introductions or did they just give it to you?

Benny Rubin: Well, this is another thing that I think about a lot. and I always try to recommend people think about if you think about yourself as an ecosystem player. Like you’re part of an ecosystem and you, and you particularly focus on clients that are also parts of ecosystems. It’s generally easier to grow through referrals, meaning entrepreneurs, early stage of an entrepreneur, seed stage sort of entrepreneurs.

Now they’d probably be referred to as pre seed, but seed stage in general tend to run in packs. They have all these common points. They have the same venture capitalists invest them. So they have a group of people that are in this community. Maybe they went to YC. So they have these thousands of YC companies, Y Combinator that are part of them or whatever. So. I focus on early stage startups and early stage startups spread information across. They always spread information across. Someone posts up, Hey, we need help with this. And they go, Hey, this guy helped me. It was very efficient the way they ran it. And so that became, the way that you grow. So yes, referrals largely unsolicited.

I never really have gotten into the business of asking clients for referrals very earnestly and directly. I know that there’s value in that and I’m sure. You could build a really great process around it. And that’s one of those things I always push down on my to do list, but I found that we get enough referrals and we’ve always gotten enough referrals that, uh, it didn’t, wasn’t like a burning need.

Andrew Warner: So you weren’t asking them, but they would make referrals. Even if you didn’t solve their problem, they would refer you to someone else. And then you also had your own emails going out and some of them would lead to sales. That’s where you got your customers.

Benny Rubin: Yeah. I’d say that’s accurate. Yeah. And keep in mind, I grew to almost 2 million in ARI without a website, without a brand name, without anything. I just said BennyRubin. com and I had five words on it. It was like, I help companies scale cold email. And like, that was it. And then when I started to add team members, they were the ones who said, Hey, it’s kind of weird.

Can you like actually have a brand name? So then I can say I work for this company. So I read a little process and I was like, I like the name senders. Like, let’s go with that. And that’s how we ended up with the name.

Andrew Warner: All right. You know what? I like not having a site or just having a personal link because it feels more like you’re hiring the person who can solve it. And not a lot of people can hire the person because otherwise they’d get overextended. And so it makes it more special. It makes it harder to get access to.

I’m a big believer in stuff like that. And in a non website start or a website that even says what Mixergy said in the beginning, which was by invitation only. And that’s all you saw, which made it feel more special when you were invited back when I was doing events.

Benny Rubin: I think that that’s a really, I think that there’s something, look, so much of business is like puffer fish and like showing that you’re big and like, look how great we are and sometimes that I’m sure there are industries where that really makes sense, but I, I know this sounds like a funny thing to say, but I only started posting on social media, like maybe two months ago.

I didn’t post maybe a tweeted once since like 2010. Um, so people always tell me all these things. People always tell me that’s a little bit like funny to say, but people always say, Oh, I, I would, I’m going to do this, but I need to do this and this and this first. And I’m like, really? Like, so in my view, I was like every day that one of the best piece of advice I ever got about building business was.

If you’re not doing three meetings a day with people that could potentially be your client or lead to someone that could be a client. The day you kind of failed. I mean, I’m not talking Saturday, Sunday. We don’t need to get silly with

Andrew Warner: No, no, I get it. That’s a good, that’s a good benchmark. If you’re not doing three meetings a day with someone who could potentially be your customer, you failed the day.

Benny Rubin: that’s what I felt. Yeah. So my thing was, okay, if I fail to do the three meetings a day, maybe I do need a brand. Maybe it can’t just be the Benny show, right? Like maybe then you really do have to do something, but I kept consistently be like, okay, well, three means that all those wouldn’t close. Mind you. I mean, I’m not some sort of weird crazy maniac

that’s selling, uh, you know, sunscreen, um, uh, you know, on the 102 degree weather or something. Yeah. I don’t, you can tell it’s getting winter time in

Andrew Warner: for a closing for

Benny Rubin: I’m like,

Andrew Warner: yeah.

Benny Rubin: um, but you know, Hey, well, you know, maybe next week I’ll worry about brand because I just signed another client and I want it to vote managing to helping them and on and on and on and whatnot, and people would email me back and be like.

Hey, maybe you should put some information on your website. And I’m like, why? Set up a call with me. I’ll tell you everything you want to know. So all this sort of brand stuff is very, it’s relatively recent, but I also understand the value of brand. I’m not saying there’s something wrong with it. I just didn’t find that it was something I

Andrew Warner: What did you say that got people on a call with you? What worked?

Benny Rubin: I always liked very explicit explanations, very clear explanations of what happens, like what’s done, what decisions are made. In general, I find that that, that typically is what is the nicest. I think that the ones where you sort of wave your hands and say, uh, there’s something mysterious that you’ll have to know to talk to me.

If people aren’t the people that are attracted to working with my company, aren’t interested in. I think part of the reason why we have so many clients and we always have is that we’re very, very transparent, meaning we can make decisions on your behalf, but we’ll also involve you in all the decisions if you want to be.

So if you’re a technical person or a detail oriented person, you’d like. That kind of relationship. So bringing that into cold emails and bringing that into conversations. And that’s honestly what I hope from anyone who listens to this. I want them to think, I don’t know if we’re having a problem with deliverability.

Maybe we are, let’s set up a meeting with these guys. Cause at least we’ll get a straight answer. And, and that’s what we

Andrew Warner: Was it that kind of consultative approach? Like, I’ve done a bunch of email, if you want me to help you think through how to do yours better, let’s get on a call? Or was it more like, I do a service where I increase your Your deliverability and closing via email. If you let’s get on a call, see if you want to hire me.

Benny Rubin: I actually go, I think that things should be even more detailed if you can. Which is we, what we care about, what, look, what it actually, what we actually do is sort of an interesting way, I think, to get people in the door. I find that sales calls don’t go that well in general. If someone comes and they say, okay, well, what do you do exactly?

I’ve rather than say, okay, I know all the pieces on the chessboard. I’ve tried to put them together myself, but I couldn’t quite get them to fit. Walk me through how you, your team helps me get them to fit. Does that make

Andrew Warner: Yeah. You want it. You want them to know there’s a problem and get on a call with you to see how you would solve the problem and evaluate you. It’s that straightforward. And that’s the beauty, I think, of this business that. It is salespeople doing sales, sales emails. You’re coming in and you’ve got a way to either grow them or you don’t.

And if you do, let’s hear it and it’s worth paying for. And if you don’t, then we’ll know pretty quickly, but I, I’m not looking for consultation. I just want to, I want results.

Benny Rubin: I always joke that no one really goes to like the knee doctor, unless you have like a knee problem, like I just, I mean, I don’t know any knee doctors myself, but you can imagine no one goes like, yeah, I want to schedule an appointment with you. My knee’s great. It’s working great. I just wanted to, it was like, something must be amiss. All of my calls now are people who have something amiss. Something’s off. Hey, we used to get 43 percent open rates. Now it’s 27 percent and we haven’t changed that much else. We used to have six senders sending X amount and now we can’t even send Y amount. Why? What’s going on? What’s going on? What’s going on?

And then we present our solution. Like this is how we approach this problem. Or here’s the particulars of your situation that we think we can. And here’s what we do and here’s what you do and everything, et cetera, and a large, a surprisingly large number of people are excited and just like, oh yes, okay, we want you, let’s work together on

Andrew Warner: You know, Benny, I guess I would have thought, I would have thought for you, it would have been different. I would have thought that for you, it would have been a situation where someone says I’m getting great results from this, it’s already our best channel. If you could just get us another 5 percent increase, we’re great.

Show us what to write, show us how to get


deliverability, but it’s not

Benny Rubin: I don’t disagree that that is the Genesis. I see that as a problem. You see that as a vitamin, but I see it as a pain. Why? Cause if they could just push it 5 percent more, they would. What happens is they push it and it doesn’t happen. So now they’re going, wait a minute, something happened.

I thought if I just increase my sending volume, better results. Something’s up, something’s weird, something’s amiss. And then they come to me because if you push the volume up and it goes, Hey. You don’t, don’t talk to Benny. You don’t waste your time. Why would you even talk to the team? You know what I mean?

So I feel like there’s like two sides of it. for example, my own business, if you were a business coach, you’d say, well, what, why haven’t you guys hit, 5 million a year or whatever the target is yet, and it’s not for lack of trying, right? That’s how it always business always is. It’s like, what is the.

What is the, what are the inputs and what are the outputs? And sometimes they correlate directly and sometimes they don’t. So when it comes to email, if your input is more and the output is less, something’s wrong. So then they come to us to, to, to try to explore if it’s a sending problem. Is it a delivery problem?

Is it something in between? And we do our best.

Andrew Warner: You got to 2 million in sales without other people, without a website. How much of that was profit?

Benny Rubin: So an interesting thing happens when you build agency style businesses. I let my profit go. So I hit a pretty good amount, maybe, I don’t know, 50, 60 percent gross profit, that kind of area, which is not, weird. Then I needed to staff up and that’s where you can quickly diminish profit margins.

And with an agency style business, no matter how good you are, folks churn away from you, especially if you’re working in this kind of space. They turn away from you because, Hey, we tested email through and through. We decided it’s not something we want to invest in. That’s an okay reason. Hopefully they’re not churning because they’re dissatisfied in some way with this specific service.

So you have these churn events and if you bulk up on people, if a churn event happens, your profit margins decrease rapidly, as you can imagine. So you start with having healthy margins. Certain numbers of things happen that are negatively impact your business. You have quarters that don’t hit your goals or whatever, then your profit margins start to shrink.

So I’m not sure the average profit margin over the lifetime of the business, but we’ve tried to keep it healthy most months, some months we’ve gone into the red, but in general, fine. I mean, no venture, no outside capital, no debt, nothing like that. Cause we just don’t really need it.

Andrew Warner: Okay, let me do a sponsorship for Gusto. What do you know about Gusto? How come everyone knows so much more about it than I do, it feels like? What do you know about him?

Benny Rubin: What do I know about gusto? I know firsthand that running, payroll benefits, all that stuff is quite a pain. And it’s probably more technical and takes more clicking and everything than one would imagine. So I also know that there are a lot of solutions. there are also legacy solutions like Trinet and things like that, or that kind of category


Andrew Warner: that people want to transition away from.I’ve used a

bunch of them. I used the one that was built into QuickBooks. I used a competitor, one that you mentioned earlier. I used a ton. The problem I always had was there was something that didn’t work out and then I felt it was my fault because I don’t have the head for this stuff, which I don’t. I don’t love it. Meanwhile, the people who are most valuable to the company, the ones who work with you all the time are impacted by this if the payroll doesn’t happen quickly, or if it’s not clear what they’re supposed to get paid, or if you’re fiddling around with different documentation, or if you need to make a last minute payment and it’s on you to make a payment to them and you can’t stand going to the software, so you put it off for a little bit.

It’s a pain in the neck, so I’ve used it, right? You’re nodding. Anyone who knows this knows that’s the pain. Those are the issues. And then of course, there’s taxes where you need to figure out what did I pay these people? I want to know a report. If I’m, if I’m happy with someone, I want a quick report. How much do I pay them?

If I’m not, I want a quick report. I want the same for contractors. W 2. the beauty of Gusto is it’s super simple. You can start it if you’re just paying one person. You could build it up all the way up.

I’ve had people use this and then they apologized to me in the interview. Because they said, look, once we went public, we needed a different, more robust system. I get it. It’ll take you all the way to that scale and make it beautiful for you and your team. I was going to say employees, but at contractors too, and make it great for your team too.

This is such a good time of year to switch your payroll and benefits, service provider. That I’m doing a bunch of ads for them. And I want everyone on here to go and at least try this for free. Go use the software yourself for a moment, and you’re going to understand why this is what your team is going to be happy to use.

This is what you’re going to be happy to use. Go to gusto. com slash Mixergy, M I X E R G Y, gusto. com slash Mixergy and see how easy and beautiful it can be to take care of your people. Benefits payroll easy.

Benny Rubin: You mind if we talk for a second about Gusto?

Andrew Warner: Yeah. Let’s do it.

Benny Rubin: I think like early stage entrepreneurs, cause I consider myself very early stage. I think that a lot of people listening, cause I used to listen to this podcast when I was just getting started with business years ago, and I remember thinking like, wow, if you get to 20, 000 a month in revenue, holy heck, like that must be unbelievable and amazing.

And I built my first business and I sold it. Thanks. No, it’s no small part to the advice that I’m sure I got from your, this very


I think that companies. Founders, early stage companies, completely underestimate the upside to investing very, very early on in a platform like Gusto and other tools that you start, well, I mean, all I just pay them over transfer wise, like our wise.

com, like what’s the big deal. That’s fine. Or I just do this. I just do that. I just do that. And the second you actually have a professional process in place or, you want to up your game or someone says, Hey, can I get a, and you’re like, Oh, what? Ooh, and you’re Googling around and you end up at a place like Gusto and the tools that Gusto and potentially other companies, but Gusto is the one on topic provide are, they’re actually the way that you level up your business.

They’re actually the way you level up your employees access to information that they need about what’s going on. That’s the place where you onboard. It can be where you onboard, where you offboard, where you do all these things that are really necessary. And all those things add up to giving you a way to reduce your cognitive load. Systems of record and systems of record allow more room and space for your clients, for your approach to marketing, all these things that really are indispensable.

Andrew Warner: You know, the challenge is a lot of this type of software is just such a pain to integrate. I’ll give you an example. Just so it doesn’t look like I’m just talking about gusto. One of the things that’s a challenge is project management. You get clients, you need good project management software. You could easily get by with nothing but your own, frankly, whatever it was built into the iPhone, the reminders app, if it’s just you and one customer, once you have multiple customers and you need some way for them to interact with you.

And then for you to keep track of what needs to get done for them, it’s a pain. What, and so people put that off. What did you use for yourself for project management?

Benny Rubin: My team has tried many, many different tools and I would say that. This, people listening and now here in 2023, sliding into 2024 are going to probably make fun of me inside their brains. I even resisted Slack for my team for a long time. And the reasons are, I’m not going to go into the details as to why, but I basically was just like, you know what, we’ll use other tools, like this is fine. I found, and this is a tool, this isn’t, they’re not, I’m not sponsored by them in any way, but I found it to be the best tool that I needed for my business. Whether I had, when I had two people, when I had five people, 10 people and beyond, it’s a tool called missive, M I S S I V, missiveapp. com. Are you familiar with that manager?

Andrew Warner: No, I’m looking them up right now.

Benny Rubin: Um, it’s a team up in Canada. They’re very nice people. They’re very responsive. They build features all the time. They’re really excellent. I’ve done a testimonial for them, uh, just a few months ago, which I, I’m really happy about being able to support them. It’s a shared inbox tool. You might be like shared inbox, like, come on, do you really need that kind of thing?

Look, clients have every right to email you. They have every right to Slack connect you. They have every right to do all the things that clients do to try to get your attention and get the support and help that they need. What missive does is it gets rid of all the CC, BCC kind of issues that come with emailing.

So for example, I’m CEO and founder. Sometimes people just like to email me that they can’t think of their account manager in the moment. And they sent a note to Benny. There’s nothing wrong with that. I don’t want to discourage from doing that. Oh, by the way, Manuel is your account manager.

Please direct underneath the email through the whole thread. I can just tag Manuel. Manuel can just jump in and reply as Manuel or my assistant can write an email reply as me. That I can then approve shared drafts, all these things. So it’s a layer on top of email that really helps. I found for a long time that project management software wasn’t what I needed.

I needed almost like ticket management without like tickets. You know what I mean? Like you’re a number one, one, three, three, five, five, five, like without all that stuff. So I sort of approached every individual task as like a ticket. And then the other thing that I think oftentimes happens is. You, you need to always be thinking about your rapport with your own clients.

Almost every single failure of a client leaving dissatisfied was due to lack of rapport. And so sometimes tools can create distance between you and a client. It can hurt your rapport. Like they think I’m not talking to you. I’m talking to a thing and I don’t want to talk to a thing. I want to talk to a human.

And sometimes tools can build rapport. And sometimes it really makes sense to ask clients, like. Welcome to be a client and they get an invite for some tool and they’re like, Oh, okay. Whoa. But sometimes that conversation can lead to better rapport. Hey, we use a tool. We use Asana. Do you want to use Asana with us?

If you do, we’re happy to onboard you in Asana. We’re happy to show you how to use it. We’re happy to show you how this can build rapport. And so all the failures that I see in my own business and management have been from me not having the confidence to have a rapport based tool conversation with clients to really match them where they are.

Now when you have Slack connect with some clients, obviously we do email. Missive is a layer on top of email so we can fluidly share things amongst clients with email. But that’s, that’s sort of where my mind’s at usually with these, these things.

Andrew Warner: So you’re thinking if they like email, I’m not going to introduce them into Asana. If they like Slack, I’m not going to force them to email me. You just will go wherever they want to go.

Benny Rubin: Oftentimes we just go wherever the client wants to go. Now, if you’re going to systematize really. Seriously, I mean, we’ve never had a hundred clients at the same time. I think the most we ever had at one time was maybe 80 or something. now we have somewhere around 70, I think 70, 70 to 80 range individual companies that are our clients. you create overhead by creating tickets that then get passed around and sort of checked off from a client’s perspective, at least with our clients. Almost all of the changes that they want made, they, they’re, it’s conversational. For example, a client just emailed us the other day. They said, Hey, we want to increase our sending volume from, 20, 000 emails to 36, 000 emails.

And we want to cycle this team member off and cycle this team member on. Like that’s a weird, okay. Create a ticket, go to JIRA, create it. It’s like. Like that’s a little bit weird. So if we, when we use a project management, like Asana and stuff, we like prefer it internally, like, Hey, sling it to us, we know how to structure the ticket.

So it gets done internally. Or if it’s a spot thing, like I’m going to go in and do it. Great. So it’s done. The, the sort of receipt is sending the client and, you know, back saying, thanks so much. Got the note. This has been completed. One of our core. One of the core things that I was talking about with the team, I call it closing loops.

there’s a million ways to say it, but I call it closing loops, which is you do the work and then you tell the person that the work is done. Basically you close the loop. I feel like if the loop is closed and there’s some record of it being done. Do we really need to have it logged in another way, in a very particular way?

No, unless it’s something that has very direct ramifications for later, and then you should have it logged in a very particular way. So, I’d say, I like the kind of business where clients feel like they can fling stuff to us in any way and shape they want. Sometimes if it gets out of hand, you need to corral them, but that’s a rapport conversation.

Hey, you sent me a lot of WhatsApp messages. Would you mind just like doing it a different way? And the client’s like, Oh yeah, sorry. When I think of it, I want to send a note. Okay.

Andrew Warner: I get that.

Benny Rubin: Hey, I have a new WhatsApp. It’s a business WhatsApp and that goes straight into missive. I mean, I don’t have one, but I could do that because missive allows you to have WhatsApp to go straight into

Andrew Warner: Really?

Benny Rubin: email client.

Andrew Warner: But Slack will still go into your Slack if they’re slacking you. Yeah.

Benny Rubin: to go into Slack, sure. if it’s Slack connect, then it’ll come into your Slack. Sure. But then with Slack, at least Slack connect, you could have your assistant or a team member that’s not you join it. And then you could set notifications and be like, if you tag Benny directly, Benny will see it.

If you don’t tag Benny, then he might see it, which is also just report, right? You tell your clients, Hey, here’s our rules of Slack. Are you cool with these rules? If you violate these rules, I’ll remind you a few times, but

Andrew Warner: Tell me more about rapport. People are not hiring and keeping agencies because the work they’re doing is good. It’s because they have rapport. What do you mean?

Benny Rubin: Well, I have this, I’ve noticed this phenomenon after working with hundreds of clients. And I wonder, honestly, wonder if your readership has noticed a very similar phenomenon. When clients need to, or want to leave your agency or whatever service you’re doing, there’s like a magical tripping point where they switch from being on your side of the table to being on the opposite side of the table.

There’s a tone shift. There’s something that sort of feels like, Oh wait, we were working towards shared goals. And now we’re working against each other

Andrew Warner: Yeah.

Benny Rubin: and for a long time, and this is with my company, when I was in my twenties and everything, I would just sort of be like, okay, something changed, Hey, something changed.

It’s fine. You can move on. No problem. Happy to process your cancellation or whatever you want to frame it. But nowadays I’m much more interested in proactively having hard conversations with clients. And when they do a move, that’s clearly the opposite side of the table, actually having a hard conversation with them and saying, Hey, We used to be on the same side of the table.

I feel like we’re not, let’s talk through what’s going on. Nine times out of 10, they’re very clear about what happened. What changed a lot of time has nothing to do with your service or anything. They say, yeah, we have a new VP and he’s really, or she’s really this or that, or Hey, you know, the ROI didn’t really pan out in the way we need to do, or we had to move the goalposts and now you’re in the midfield, you’re not near the goal at all.

And. Nine times out of ten, it actually can be corrected by renegotiating all of the terms. You just say, okay, whatever agreement we have now, whatever money you’re paying, whatever services, let’s put that all the way to the side and let’s pull one back one by one. Okay, what about this that we were doing?

Do you still want us to do that? No. Okay. Reef reform, refactor. And honestly, I didn’t know this before. I thought, Hmm, something’s weird. Okay. Well, there are a lot of fish in the sea. I’m going to move on to new clients and not devote energy to someone that doesn’t want to work with me. And now I sort of have a more of like, well, how do we end up on the opposite side of the table?

Cause we’ve this, we vibed for a long time, like what’s up. So I, I find that rapport is really like the answer to this and I’m every chance I get every client I talked to directly, I’m, I’m consciously trying to ask hard questions. Like, are we still working together? Are we still on the same side of the table?

Has anything material changed your business that we should know about? Are we meeting or exceeding your expectations? What did we totally crap out on that upset you? I don’t know, but as I get older, maybe I have a higher tolerance for having someone tell me everything’s changed. This will probably be our last month working together.

And you’re like, Oh, wow, damn, okay.

Andrew Warner: Um, I heard Greg Eisenberg’s podcast where he was talking about how he runs his agencies and he said, we do temperature checks routinely. I should probably ask him, but what do you guys in consulting businesses mean when you say temperature checks? How do you do that?

Benny Rubin: I, I have, I simply think about, I, I consider it a hard questions. That’s just the words that I use for it. Hard questions. I had a friend many years ago, who’s now a venture capitalist. Super interesting guy who said, Hey, Benny, you’ve ever heard the expression, hard questions, easy, hard conversations, easy life.

Easy conversations, hard life. And I remember just, I just threw it in the rubbish, like with the protein bar I was eating or whatever. I was just like, yeah, whatever. Another one of those stupid phrases. And then it sort of crept back to my consciousness soon after. And I was just like, Oh man, that’s really interesting.

So I literally carried that. And I said, okay, I think I took like a post it note and I wrote like hard questions and I stuck it to my computer monitor or something. And I just said, okay, every conversation I’m in, what is the hardest question I can ask? So I just tried always to ask the hardest question I can ask.

Oftentimes you don’t need to ask hard questions. it’s a team member you’ve been working with for a while and it’s all fine. You get on a call with a client you haven’t talked to in a little while, or you’ve seen some bumps along the way and worked with them. So for me, it’s just like, what’s the hardest question I can ask.

And sometimes I’m surprised at the question I ask. And sometimes I’m not, sometimes it’s just like. Is this ROI positive for you at all? Even theoretically, is the channel even something that you care about if you think about three months from now, are you still paying us every month or how many months in the last three months have you thought, I really wish I wasn’t paying these guys.

Like, those are hard questions, I think So I think those are temperature checks probably where it’s just like, is this a sick relationship or a healthy relationship?

Andrew Warner: Yeah. That makes sense. Okay. That is a hard one to ask.

Benny Rubin: you don’t, but you don’t have heart. Do you have hard conversations with your clients, partners? or you don’t need to, is that the end? That’s the secret to the Andrew Warner life is,


Andrew Warner: if you’re talking about sponsors, it is very hard. I was thinking about, um, earlier this week, pipe drive. I loved pipe drive. I loved it so much. It was in my book as a key part of how to organize interviews or frankly, any sales process. It really sucked that it didn’t deliver the results that they were looking for and they canceled.

And I think I should have just got, well, I don’t know. I was thinking I was going to say I should have gotten on a call with them and understood how many customers did they get? Why maybe it didn’t work and maybe had a follow up

afterwards. In reality, it probably just didn’t work. Like maybe they got none.

Benny Rubin: And my sponsors are pretty good about telling me how many leads they get. But the opportunity you missed was you didn’t get the blow by blow inside their company, the path to deciding that it didn’t work because we use pipe drive. I love pipe drive. Those are great people, great people too. And my guess is that their company culture is also very generous and sharing. That’s the vibe I get from their software.

I, I have met the founders before, but I don’t. And they’re very nice people, but it’s not something that I, can speak for individual members of their team. I think it’s a toss up whether you would have learned something or been kind of like, okay, that makes sense. But it’s also possible that you could have had another shot.

Why? Cause they said, you know, we really want to focus on this other new feature set. And, and you went live or whatever you did with them. After we’d already shifted our focus. So, or something like that, like there’s always some interesting layer to the story that makes you go, Oh, interesting. That’s interesting.

Andrew Warner: I would even think that doing a follow up, like Getting to know the person better, who’s responsible for the ads and then doing follow ups after. So it’s not even about how my ad performed, but in general, how are ads performing for you on podcasts? And then it’s possible that I would have discovered that podcasting is just not the right medium for them.

I don’t see them on podcasts. So maybe that’s what it is. Or maybe they realize that, you know what, this whole SMB business is not really right for them and they need to go somewhere else. And so that ongoing conversation would have revealed that, um, And that’s


I would spend

Benny Rubin: you’re the, you’re the star of the show. I found that hard conversations have Can have a similar effect, even if it’s not the star of the show, meaning almost anyone from my org, having a hard conversation with someone, and even just, Hey, I had a conversation with dadada because he said dadada and dadada happened, it can have a very positive effect on the relationship.

Now, as founder CEO or whatever position, the highest position, there is obviously more gravitas and whatever, and you have more levers to pull to correct the situation. So it’s not saying that you could easily replace.

Andrew Warner: Yeah,

Benny Rubin: Usually people just want to have the hard conversation.

Andrew Warner: yeah.

Benny Rubin: there are instances where you go at it to try to have a hard conversation and they really are just like, Oh, you’re trying to sell me to keep me engaged in something I don’t want to be.

So you could face resistance too. So it’s not like it’s always goes smoothly. And like the magic words are hard questions and then they, they open up to you in a magical way and

Andrew Warner: No, it’s, it’s worth doing even if, it fails, it’s just to keep the relationship going. And like I said, you learn a lot. And frankly, Gusto, the woman who called me back up from Gusto, we had turned them down a long time for sponsorship because we were just so packed. And then we kept saying, it’ll come, we’ll, we’ll clear it up.

And we did. And she ran some ads. She’s not at Gusto anymore. She’s a convert kid, but because we had a relationship with her, when she knew that the team of Gusto needed more spots, that would be effective, she said, look, let me go back to Andrew. And she personally, even though she’s not with Gusto, she personally reached out.

And we just closed it. And then she took care of it with the Vesto

Benny Rubin: We get that we’ve gotten quite a few of those very recently people say I We’ve I think there’s been two calls in the last three weeks that were Someone set up the call you join and then that person goes I don’t work at the company anymore But I still really like them I still want to support them and I talked to them about this or that and I remember and I’m like, yeah, okay So it’s kind of interesting where it’s like they like join the call because it’s fun, which is a whole different thing, i mean I feel like most sales calls are more boring than they need to be.

And any shred of entertainment that can be bringing to a sales call should. So sometimes people will just tag along on a call to sort of watch the action as I like diagnose their, their email deliverability problems

on the

Andrew Warner: You know what? There’s a tool. I was looking it up. Peep Laja did this in his podcast with the founder of user gems. They tell you when the people who are your clients have moved to another company so that first of all, you’re aware that you need to build a relationship with the new people, but also you can just check in on them and see, are they using a tool like yours at this company?

It’s such an interesting. Uh, it’s such an

Benny Rubin: it is. User gems is very interesting and that’s. It’s very valid. I think that there’s like a golden period when people join positions where they’re getting their bearings and they’re sort of asking like, you know, why don’t we have one of these? And everyone’s like, oh, that’s a thing.

You’re like, yeah, last three companies had one of those. Like, why don’t we, and then everyone’s like, well, you’re the expert. You’re the one who use it for the last three times. What do you, and then at that moment you get an email

Andrew Warner: yeah.

Benny Rubin: someone. But I, I think there’s something really beautiful about expertise that people accrue over time and how the context of work changes so dramatically what the job is. So people. For example, someone might say, I was at a company and we did a thing with you years ago at a very, very small scale when you were smaller scale and it worked really well. Now we’re much, much bigger scale. And someone mentioned you. And I didn’t think because you were so small scale all those years ago, but now you’re actually the big scale that we need.

Right? Like, so their job context changed and you’ve changed. So it almost, makes sense to always be thinking about how to reintroduce yourself, sort of milestones and sort of reaching out to your community and like letting them know, what’s different, what’s changed. We get clients that come back now that say, you guys still doing cold email?

And we say, yeah, you guys still an agency? Like we run cold email for us. Well, no, we’re really focused on deliverability. Oh, good. Cause that’s the exact thing that we need help with. Cause we don’t need your help writing emails. We already have a marketing team and all this stuff, but we’re just having trouble with. And we knew that you guys were good at that. We’re like, ah, yes,

Andrew Warner: right. Speaking of that, Google made a big change recently. I don’t know what it is, but you were prepared for it and I don’t know why you were so prepared. What happened before that got you to be almost like you’ve. You’ve, said to me, digital preppers, what happened before? And then how did that help now?

Benny Rubin: I don’t know. There’s like a really clever expression that people say. It’s like, uh, you know, America farts and like rainforest dies or something. Like, Google’s obviously this huge player. I’m old enough. You’re probably old enough to know when Google made that SEO change, we all had friends that just completely lost all their traffic.

Some people had to shut their whole businesses down because Google just said, Hey, we’re making a few small changes. We’re going to be, prioritizing this over that and that over that. And everyone’s like, Oh, really? And then the day that change happened, traffic through the floor and other people, huge winners, Hey, we were buried in Google for years and now we’re at the top of the thing, like, wow, our business is great.

So Google has long been making moves, both overt and subtle to try to get people to stop using their. Email systems to send unsolicited emails. And they have a lot of tools in their toolbox. One of them is they actually suspend your account if they feel like you’re using email inappropriately. And that’s a very common thing.

And it’s becoming more and more and more common. And even in 2020, when we started to shift, we shifted everything off of Google. We’re already seeing that like tick up and up and up. And we said, we’re a professional organization. We don’t. Want to have to flag down the admin from, uh, you know, they get an notification being like, blah, blah, blah, user was suspended, fix something very jarring, very upsetting.

So we said, look, we’re not going to deal with that anymore. So it was very visceral. Like it just seemed like a bad. Experience for our clients to have to drop everything and help us out. So when we shifted using IP, IP addresses, IP pools, and really understanding the mechanics of this to make it work without using Google, that inadvertently prepared us.

The most recent changes Google is making, which are very timely. I think they’re going to affect in February. Don’t have to do necessarily with the sending side. They have to do the receiving side. So what they basically said, if is you Mixergy. Sends emails, and three out of a thousand of the people who receive your email within a 24 hour period market a spam, we’re going to assume that something’s weird, off, not right, and we’re going to limit it.

The number of emails that we deliver to our users from you. So that’s the change that they made. they made some other changes too, but they made very clear recommendations on how you should handle this, how you should understand it, how you should contextualize it. But of course the reaction that people have is much bigger and scarier.

And it’s also unique to their own circumstances. So we’re spending a lot of time talking with clients, working with, People that come through that are saying, how does it relate to me? And then we can help them through that process of understanding it, because we’ve already been in this game of avoiding pissing off Google for so long that avoiding pissing off Google is sort of second nature to the way our company thinks about email in general.

Andrew Warner: How could you, how could you get past it?

Benny Rubin: So Google is, is a fascinating, company. They, how do you, do you think a lot about email? You have people on your team that, that think about email and email delivery. And I’m just curious, like where, where it sits in your,

Andrew Warner: It’s not at all an issue for me when I think about me sending out email from my personal account, because if I’m sending out an email to solicit someone, it’s not that many, it’s not a problem. And there’s a, and I warm up the relationship before I ask for the email newsletters, it’s a pain in the butt.

I think about it so much that I just stopped sending out email. The system that we use is such a pain. If people didn’t hear from us in a while, we can’t email them. It’s, I’ll say the name. I hate them. It’s, I shouldn’t say I hate them. It’s Infusionsoft. I don’t like them. They’re now called Keap. Um, And I do feel like a jerk for even sending out email to my own list and then they block certain people, which I get.

And so, yes, I do think about it a lot. I’ve earned the right to reach some of them. I’ve earned the right to reach them all. They’ve asked for it. And some of them, I can see are really close friends, like Kareem Mine. I’ve interviewed him. I’ve known him for over a decade. He is someone I can’t send email to, not because he hits spam, but because the software service provider that we’re using.

He’s so scared of, of a spam issue that they won’t let me email him. So yeah, I definitely think

Benny Rubin: Yeah, so that kind of story upsets me on a visceral level. And the reason why it upsets me on a visceral level is email is an open thing. It’s baked into the fabric of the internet. You have opt in permission to send these emails. There’s no reason why you shouldn’t be able to send the emails that you want to send.

There’s no reason why you shouldn’t be able to bear the risks associated with sending emails, whether it be bounces or whatever. The number of like abstract layers that sit on top of sending email is oftentimes too many, meaning you click send on Infusionsoft. I don’t know how Infusionsoft works on its own, but are they providing the IP addresses?

Do they have someone else who’s providing them IP addresses? Who’s the admin that gets to

Andrew Warner: it. I do


Benny Rubin: the threshold is for? So oftentimes, Folks just need our help to switch off of systems like that. So they can expose more of the stack. They can have an understanding of what’s going on in their email with a, with a deeper, deeper level.

Maybe there’s, there’s a whole host of things that it gets a little bit unfun, like pretty fast and people kind of, their

Andrew Warner: Yeah. Truthfully, even when you gave me the floor in the beginning of the interview, I was like, Oh my God, this is how he’s going. It’s going to be tough for anyone to follow.

Benny Rubin: Well, yeah, you can tell what my conversations are every day. all day, every day it’s, it’s IP addresses, email systems, et cetera. But what all I was going to say is that the. The reason why I ask that is that if you send it email. And you get a notice back that says, Hey, we didn’t deliver this email.

That’s an email server doing you a solid. They’re like, Oh, Hey buddy. Like, yeah, we’re not going to deliver this. And you’re like, okay. Google doesn’t send any notices back. They don’t send any notice back. What they do is they. Add it to like a number and like a database and then they give you a tool that you have to sign up for called Google Postmaster Tools.

And then if you go to that tool and then you authenticate your domain

in your, and then you look, then they’ll tell you what percentage of people marked your email as spam in any 24 hour period. No more information, no less. That’s it. So what Google said is, hey, we have a new rule. It’s a 0. 3 percent rule.

The only way for you to know your number is to go use Google Postmaster

Tool. it’s like a weird thing that Google gives you the rule and they tell you how to not violate the rules.

Andrew Warner: Okay,

Benny Rubin: And that’s sort of the, the, the secret to this is like actually reading the words that Google published about their new rules.

Andrew Warner: but still I don’t get it. If there’s, if your clients are sending out cold email out of a thousand, how did you avoid having three? The only thing I could think of is you have to basically have a bunch of IPs, a bunch of email addresses, a bunch of everything so that you could pretend you’re sending out fewer than a thousand, maybe 999 through each one of these systems.

Benny Rubin: I think you’d be surprised most business solicitation email, all of our clients, for example, they’re one, they’re pretty good at this. They’re pretty good at this too.

Andrew Warner: They’re pretty good at like, what, not writing email. That doesn’t get you, it doesn’t get you flagged.

Benny Rubin: No, they’re pretty good at this in the sense that,you’re sending emails to people in your target market. Your value proposition makes sense to the people you’re emailing it to. So it’s very rare that if, for example, you were sending out an HR tech related thing, let’s say you’re doing a talent acquisition technology or something.

I’m just making something up. And you’re emailing talent acquisition managers about talent acquisition tech. That person is not like, this is spam. They’re like, no interest for me. They’re not, they don’t bring malice into their like spam marking. They’re not, I’m so upset. They’re just like, Oh, an email of someone trying to sell me something that’s relevant to what I do, even if I’m not interested.

So that’s one side of it. The other side of it is Google is not the only game in town. So you might send out a thousand emails in a day, but maybe only 500 of them are to Google. So

Andrew Warner: And so that’s another thing I’m assuming that you work with them on to


Benny Rubin: sometimes you have to, sometimes you have to balance what you’re going and no, don’t get me wrong. Cold email is annoying anyway.

It’s, I’m not here to tell you like cold emails, great across the board and you should use it profligately and send as many as you possibly can. I think that just like with any other growth mechanism, whether it be telephone, cold email, advertising, and whatever, you have to try to bring as much humanity into the Europe. Execution. Everything is possible in order to not come off that way. But the, the sad truth or the good truth or the whatever is that it works. It actually is, is quite an effective way to mass introduce yourself to your target market. If that’s the mode of business that you’re

Andrew Warner: It must be, it must. I see it going out. I see people get results from it. It’s a key part of how people are getting business.

Benny Rubin: and I bet even in your own org, people have purchased something from cold email

Andrew Warner: I mean, you and I connected because of a cold email. I’m sure that we were introduced through someone who did

Benny Rubin: way,

Andrew Warner: You don’t think so?

Benny Rubin: well we were introduced directly, but maybe how they got in touch with you was cold email originally, which would not surprise

Andrew Warner: but he, no, but you know what? I don’t, I can’t tell the good stuff. You can’t tell, is it real or not? is it customized to you or not? I I’m pretty sure that actually for him, it was customized. He happened to email me today too. So hard to say, but every once in a while it does absolutely work.

And some of the biggest companies still use. this kind of Cold outreach to ask me for, to interview the CEO that hired them. You know,

Benny Rubin: yeah. Well, I mean, look, it’s, effective. It’s open. It’s asymmetrical, meaning it’s more effort to send the email than to archive it or see it or remove inbox. So I think that there’s a time and place for it for sure. I’m yeah,

Andrew Warner: let’s close it out. Give me some tools. Then if people are at the end of this interview, looking, Oh, look at this. Parker sent me an email, been lurking for a long time and I responded, but I couldn’t get back into it. This was in August. So August 4th, I responded and then we didn’t get a follow up August 7th.

I. I followed up. No, August 7th, he followed up. August 16th, he followed up. I responded on the 22nd. Then I just dropped the ball. 22nd, he’s back. September 6th, he’s back. September 11th, he’s back. September 21st, he’s back. October 5th, he’s back. And then not only was I glad that he was back and that we, we got to do this interview, he and I got on a call to deal with another issue and we’ve been texting.

In fact, we texted today. So, um, so yeah, I could see


Benny Rubin: a great dude. He’s a really good dude.

Andrew Warner: Yeah, I

Benny Rubin: Yeah. He and I, we did a book club. We just read the same book and we’re going to meet next week to talk about it. We read,

Andrew Warner: What’s the book?

Benny Rubin: uh, Doppelganger

by Naomi Klein,

Andrew Warner: What’s it about?

Benny Rubin: Naomi Klein’s new book. Oh man. It’s a dense thing. it’s not just something I can say in one sentence, but it’s a, It’s an exploration into the theme of doppelgangers when it comes to people and, their mirrors that they create for themselves on the internet, like the, internet version of Benny Rubin, all the way through time, history, et cetera, et cetera. And in particular, Naomi Klein is a leftist thinker.

that people started to mistake for Naomi Wolf, which is another leftist thinker who is an anti vaxxer and sort of all these other things that Naomi Klein is not. So she wrote a, a book exploring the idea of having this double on the internet that is not her, but

Andrew Warner: Why are you reading this? Why do you care?

Benny Rubin: oh man, I, I, I read all sorts of stuff.

Andrew Warner: Just, you

Benny Rubin: I like to read. There’s, so much, there’s so much in for me. I mean, I, I listen to a lot of music, classical music, modern music. I go to lots of concerts. I make a lot of music. I think a lot about music. I read poetry. I read novels. I read fiction. I read history. I read anthropology. I like, I’m not on this earth to build, the biggest, most powerful agency in the world.

I will be the next Elon Musk. Like this is a living is a, is an aesthetic experience. it’s about, what’s in front of you. What’s a good, what’s swimming around in your brain. What do you eat? What do you do? You know what I mean? I think business is great. And the thing that we all like about business is helping.

I think at least helping other people achieve. Or, solve problems that they’re facing because if the problem is there, then a problem is probably real and you can sort of help them solve it. And it’s a relatively nice thing to just be like, I’m big and strong. And there’s a rock in front of your car.

I will move the rock. That’s how we feel. We’re moving email rocks away from people’s, their path in front of their house or something.

Andrew Warner: All right, let me close it out with this. Give me one technique for, cold email that’s working today.

Benny Rubin: Oh, that’s great. The bank shot, we call it the bank shot.

Andrew Warner: What’s that?

Benny Rubin: Um, the bank shot is when you. Offer something that is undeniably attractive to your target market. That the pathway to get that thing is through an earnest conversation with you. So an example of that would be, do you run your own podcast?

Hey, we have a podcast. It doesn’t have high viewership, but we put a lot into it. We put a lot of effort into it. Can we interview for the podcast? We’d like to interview CEOs or whatever. They, but we’d like to do a pre interview first to make sure we’re aligned. Lo and behold, pre interview call, you’re explaining to them what your product does.

We’re this, we do this in this way. This is my stance, et cetera. A lot of times that CEO that you’re going to be interviewing with, Hey, that’s interesting, I’ll introduce you to my CMO and you can talk to them about it. So that’s a bank shot approach. Those tend to work pretty well because the value is sort of understood and it’s not going to be boring.

Andrew Warner: What’s another example of something you could offer someone?

Benny Rubin: So that’s in the case of you have some sort of media thing. Um, another thing that a lot of times do is, for example, a bank shot style approach would be, Hey, Google just changed the rules. We do free trainings every week. We do them on Tuesdays and Thursdays from three to 4 p. m. You can join and you and your team can join.

Just hit reply and let me know who’s going to be there. I’ll get you to the invite. Well, it’s a cold email. It’s opt in you’re sort of engaging with them in a way. Another, bank shot can often be the, if the star of the show. Is it going to be the one doing the calls? Oftentimes that’s interesting. So for example, if you wanted to do a big run, you want to increase your corporate sponsorships or something, or you want to get to a new tier of sponsors or whatever.

You saying, I would like to talk to you myself about

opportunity. this is about me. It could actually be very attractive for a VP of marketing or something, or a CMO, because they’re not going to talk to some salesperson, they’re going to talk to the star, so that could be very attractive. You just means you have to commit to a certain number of these things in order to make it viable

Andrew Warner: I could see how this harder, but it’s good. Oh shoot, I gotta run Let me close it out with this one. Jessi Pujji, who previously founded Ampush and had been on here. Ampush was, ad buying, platform and He now created GatewayX, his collection of companies. He showed how he gets people to, contact him and how he closed sales. And a lot of it was cold email ish. Actually, it wasn’t cold. It was warm. What he would do is he would say, who do I know in common with them? And then he would fire off a message to the person who he knows in common with them and say, Hey, do you know Andrew?

And then you go, yeah, it just was interviewed by him. And you know, what’s going to come next. Jesse’s going to say, could you make an introduction? Now, if you make an introduction, you get a way better result than if I just, if he just reached out to me directly, I tried this to help book guests. I reached out to guests directly.

Ah, it’s okay. It’s easy to just not respond, but then what I did was I reached out to people who know the guest often, not even as well as I do. And I said, Hey, do you know this person? Can you make an introduction? And they did. And because the introduction came from someone else, it became, I guess, I don’t know.

There’s now someone watching whether you’re responding to Andrew, someone beyond Andrew helps tremendously. That is such an effective technique. I would love that be systemized. In fact, we’re talking about Parker. Parker is Parker Olson. I’ve been talking to Parker Olson about this. There’s gotta be a way to just go into LinkedIn.

I give you a list of people that I want, scrape some of their connections and then through the scraping, get their email addresses using contact out and then

Benny Rubin: It’s totally doable and I don’t, I think that largely the size of the target markets of most SAS providers, like doing a direct thing is so much more efficient, but most people are running multiple strides at the same time, which they totally should. I think for key accounts, like that kind of warm thing, it makes sense, but for the large volumes of companies want to go after cold.

I mean, I, I think. The kinds of volumes of total adjustment markets that people have for their SaaS products.

Andrew Warner: How many emails are they pushing out a day?

Benny Rubin: A lot of our clients send 80, 000 emails a month easily, 4, 000 a day. It’s like not even that much, not that many in the grand scheme of things. If you have 50, companies in your target market, and there’s three or four or five people at the company, you can see that the volumes can get really high.

Andrew Warner: But they will do the bank shot and it still makes sense at that level,

Benny Rubin: Well, that, see, then you get into how you organizing the process. right?

Andrew Warner: okay

for example, you might find that only one out of 10 of the pre interviews actually go to the podcast. Why? Because, Hey, we’re trying to find a match here and I can see, you know,

we really

the conversation in a way that a sales email wouldn’t.

Benny Rubin: Like if you had said to me, Hey, Benny, if you don’t share revenue numbers on the call, I’m not comfortable interviewing you, maybe that would have been a deal breaker.

Andrew Warner: But at least we would have been connected, you’re saying, and so it doesn’t. All right. I should say I got to run.  All right. the website is senders. co and I want to thank gusto for setting this up. Uh, gusto. com slash M I X E R G Y.

You’ll love it. You’ll thank me. All right. Bye everyone.

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