Photo Enclosed, Do Not Bend: Emails, Events, and Entrepreneurs with Ryan Deiss

Episode 44 of The Verblio Show

Ryan Deiss is a lifelong entrepreneur and marketer best known as the CEO and founder of DigitalMarketer and the host of North America’s largest digital marketing event, the Traffic and Conversion Summit.

In his conversation with Steve, he shares tangible tips on everything from how many emails you should be sending to how to make your virtual event a success. He also gives a masterclass on marketing in the new world of digital art, talks scaling and leadership, and reveals the weirdest thing he’s ever sold on the internet.


Name: Ryan Deiss

What he does: Founder and CEO of DigitalMarketer.

Find Ryan on the web: DigitalMarketer | Ryan Deiss | LinkedIn | Twitter

Get smart: “If you’re not emailing your list at least once a week, they’re gonna forget that you exist.”

Top Takeaways

Why marketers can’t be afraid to ask

A lot of content marketers get into marketing because they are afraid of selling. “If you take somebody who is afraid of selling, afraid of rejection—meaning they want to be liked—then social and content marketing is going to be your favorite marketing medium ever,” Ryan says. The problem? As a marketer, you can’t only provide content. At some point, you will need to sell to your audience—or someone else will. 

The secret to selling is to recognize that your relationship with your customers is one of give and take. Providing content is like making a deposit in your relational equity, and asking your audience to become a customer is like making a withdrawal. Making a withdrawal is okay when you’ve already deposited the funds, and it’s what will keep the relationship moving forward. 

What makes a successful virtual event

Ryan tells us how his son, as an introvert, loved virtual schooling when the entire class was online. When it was back in-person, though, and he joined virtually while home sick for a day, his feelings changed. “It was clear they weren’t talking to me. It’s like they didn’t know I was there, and so I just sorta felt left out.” That lesson clicked with Ryan, and he took the words to heart when designing the virtual Traffic & Conversion Summit for 2020. 

A successful virtual event needs to be designed with its remote attendees in mind first. If you simply show a livestream of someone on stage talking to a crowd, virtual attendees won’t feel the event is truly for them. One of the simplest—and most important—tips: Make sure speakers know to look at the camera, not the screen full of faces, so viewers feel like they’re making eye contact and speaking directly to them. 

How to optimize any business

Step one: Document your customers’ journey. “How does a total stranger become aware that you exist, become engaged with your concept, and actually become a multi-buyer raving fan?” Ryan asks.

Step two: Identify the bottleneck. “Then you have to say of all these different steps, what’s the one that if we were to increase the throughput, would make everything else work better?”

Your customer’s journey is only as efficient as the least efficient stage. Identify the least efficient stage and then develop key initiatives you can do in the next 90 days to improve it. Once you fix that stage of the customer journey, you move onto the next least efficient part of the customer’s journey. By doing this, you end up removing barriers for customers. You constantly optimize and improve as you go, focusing your efforts instead of being distracted by the next shiny marketing trend.   

Episode Highlights

The weirdest thing Ryan’s ever sold on the internet?

“We sold lots of weird stuff when I owned Survival Life. There was this water filtration thing and the way that we demoed it was actually having a guy who worked for us drink water out of a urinal to prove how well the filters worked. He was willing to do it, and he’s still fine to this day. That was many years ago.”

Avoid the friend zone

“People are gonna treat you how you tell them you want to be treated. I think a lot of marketers get into content marketing—if they’re being honest, and I would put myself in this category—it’s because we’re afraid of selling, we’re afraid of rejection. …It’s like you’re that guy who’s friends with the girl but you never actually asked her out on a date because you didn’t want to ruin the relationship. Then some other dude comes along and just says, ‘Hey, you doing anything on Friday night?’ And next thing you know, you’re stuck in the friend zone.”

Email customers at least once a week

“I think if you’re not emailing your list at least once a week, they are going to forget that you exist. They just are. In general, at a minimum, you should be sending two emails a week. I’d send some content, a newsletter probably earlier in the week, and then at some point, I’d have some type of consumer-intent type thing.”

The exciting new world of digital art

“I’m pretty excited about what’s happening in the digital art space. All this stuff happening with blockchain, they’re able to do now with digital goods. So the idea of, ‘I own this digital artwork’ would’ve been ridiculous before because it’s out there for everybody to see. Now, just like you can own a bitcoin because they can tokenize a digital item, they’re doing the same thing with art. It’s a great thing because it means that artists are able to better monetize the work they’re doing in the digital sphere. And some of the most cutting edge art is happening right now in digital, but because there was no way to make it rare—for somebody to truly own it—there was no way to raise the prices.”

Want to keep teaching? Better keep doing

“I think the mistake a lot of training companies run into is, they stop doing the thing they are teaching. Once they become teachers, they stop being doers. They get out of the game and that’s when they become irrelevant.

…We do and then we teach. Most people don’t do, so they teach everybody else’s theory and wind up being some kind of chicken, mealy-mouthed thing.”

Scaling means hiring for your strengths, not weaknesses

“If you want to grow, hire for your weaknesses. Scale means hiring to your strengths. It means having somebody else do that thing. That’s what gives you the opportunity to replicate yourself. It’s what gives you the opportunity to have a bit more perspective.”

Top Quotes


[3:54] “As marketers, this is supposed to be fun. Sometimes you just gotta do stuff to make yourself laugh.”

[10:00] “I’m not sure that one person truly can run multiple businesses.”

[12:33] “A lot of marketers and content marketers get friend-zoned by their customers. The solution is simple. It’s give, and then ask.”

[13:00] “Content informs, content entertains. Great content does both.”

[14:23] “If you’re not emailing your list at least once a week, they’re gonna forget that you exist.”

[23:13] “Serendipity is much harder to manufacture in a digital realm.”


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