Hey, it's time for something new to try! Once upon a time, I interviewed Mickey Chandler for the blog, all the way back in February. Since then, he has graduated law school and passed the bar and I thought it would be fun to touch base with him again, interview him again and anew, to catch up on where he is at today, what he's doing, and what he wants to be doing.
This time around, we did it on video! A video interview is very much a new thing for me. And so scary! So much can go wrong! But not this time around. Everything went swimmingly.
If you're looking to hire somebody for fractional privacy leadership or deliverability/compliance consulting, watch the video here or below to see why I think Mickey Chandler might be your guy.
And if you're not a fan of the whole video thing, a transcript of our chat can be found below.
Hi everyone, Al Iverson here! You might know me from Spam Resource and the various little videos I post on YouTube, LinkedIn, or wherever else you might be watching this. Today, I wanted to do something fun and interesting—talk to my friend Mickey Chandler.
Mickey, welcome! Why don’t you introduce yourself and tell our viewers a little about your background? How did you get into email?
Thanks, Al! I got into email out of frustration, honestly. Way back in the early days, email was still new and fresh, but spammers were already making a mess of it.
I remember coming home one day from a job hunt, opening my inbox, and finding 70-something emails—only two of which were from people I actually knew. That was my breaking point. I thought, If someone’s going to do something about this, why can’t that be me?
So, I taught myself how to read email headers and track down where spam was coming from. I learned how to complain effectively and efficiently, and that eventually led to a paying career.
People don’t realize just how wild the email landscape was back then. Not in a cool, dusty cowboy kind of way, but in a grotesque, chaotic way. Inboxes were filled with weird, often gross content—porn spam, get-rich-quick scams, all kinds of bizarre stuff.
These days, people get annoyed by a few unwanted messages, but back then, it was overwhelming. Marketers would claim they were doing things the “right” way, but on top of that, there was this avalanche of outright garbage.
Exactly. And even back then, we heard the same excuses we hear today: “Oh, I’m not a spammer, I’m just sending this other thing!”
The problem is, if we let everyone take that stance, email becomes unusable. I remember doing the math—if you got an email from just 1% of the companies you do business with in a year, that’s already way more email than anyone wants to deal with. Now expand that to include the companies that want to do business with you, and suddenly you’re looking at hundreds of messages a day.
No one thinks of themselves as a spammer. To them, spammers are the “bad guys,” the ones sending sketchy content. But if you’re engaging in the same behaviors, even if your content is different, you’re still contributing to the problem.
That’s a great lead-in to another topic—policy compliance. Your career evolved into a focus on compliance and policy enforcement, even before “deliverability” became a widely used term. What drew you to that particular niche?
It was a natural transition from what I was already doing. Before getting into email professionally, I worked as a legal assistant for a personal injury attorney in Austin, Texas.
The intersection of spam and the law really interested me. Even though I wasn’t a lawyer back then, I understood contracts, terms of service, and how they could be used to enforce good practices. My job was to say, “Hey, your terms of service explicitly prohibit this kind of behavior, so you can take action against these bad actors.”
Sure, some companies were making money off spammers, but I could point out that if they allowed it to continue, soon spammers would be their only paying customers—because legitimate users would leave.
And now you are a lawyer! That’s a huge milestone. Congratulations on graduating from law school and passing the bar. That had to be a massive amount of work. Were there moments where you thought, What am I doing?
Oh, absolutely. Law school was tough, and I wasn’t a typical student. Many law students go straight from kindergarten to a law degree—what they call “K-to-JD.” I, on the other hand, had a 20-year break between getting my undergraduate degree and starting law school. I had an entire career in between.
That helped in some ways, but it also made things harder. When you’re young, you’re used to living on very little money. Going back to school as an adult, with a mortgage and kids getting ready for college, was a financial challenge. You suddenly go from earning a solid salary to being a student again, and when you start practicing law, you’re notcommanding those $500–$800 hourly rates right away.
But I never wanted to quit. Even when it was hard, I knew this was what I wanted.
That’s really inspiring. So now that you’ve crossed that finish line, what’s next? Who are the ideal clients for your legal and consulting services?
I have a few different areas of focus. I still do deliverability consulting, particularly around compliance and remediation—helping senders who’ve landed themselves in “email jail” and need to get back into inboxes.
It’s a lot like criminal defense work—many criminal defense attorneys were once prosecutors. Similarly, I used to be on the other side of this, enforcing policies, so I know how the system works and how to help people get out of trouble. That could mean working with Spamhaus, an ESP, or ISPs like Comcast or Yahoo.
Beyond deliverability, I’ve also done a lot of work in privacy law. I help companies—especially those looking to expand into Europe—understand stricter privacy regulations like GDPR. That might involve crafting privacy policies, helping companies understand when they need cookie banners, or advising on legal risks tied to tracking technologies like email pixels.
I also offer fractional Chief Privacy Officer services for smaller companies that need privacy expertise but don’t need a full-time CPO on staff. They might just need someone to advise their developers, sales team, or executives when privacy issues come up.
That’s fantastic. I think a lot of businesses could really benefit from your expertise.
Mickey, thank you so much for taking the time to chat today. I really appreciate it, and I hope people take the opportunity to reach out and work with you.
Hey, it's time for something new to try! Once upon a time, I interviewed Mickey Chandler for the blog, all the way back in February. Since then, he has graduated law school and passed the bar and I thought it would be fun to touch base with him again, interview him again and anew, to catch up on where he is at today, what he's doing, and what he wants to be doing.
This time around, we did it on video! A video interview is very much a new thing for me. And so scary! So much can go wrong! But not this time around. Everything went swimmingly.
If you're looking to hire somebody for fractional privacy leadership or deliverability/compliance consulting, watch the video here or below to see why I think Mickey Chandler might be your guy.
You can find Mickey on his websites: whizardries.com, spamtacular.com and lexprotego.com, and on social media: Linkedin and Youtube.
Mickey, welcome! Why don’t you introduce yourself and tell our viewers a little about your background? How did you get into email?
Thanks, Al! I got into email out of frustration, honestly. Way back in the early days, email was still new and fresh, but spammers were already making a mess of it.
I remember coming home one day from a job hunt, opening my inbox, and finding 70-something emails—only two of which were from people I actually knew. That was my breaking point. I thought, If someone’s going to do something about this, why can’t that be me?
So, I taught myself how to read email headers and track down where spam was coming from. I learned how to complain effectively and efficiently, and that eventually led to a paying career.
People don’t realize just how wild the email landscape was back then. Not in a cool, dusty cowboy kind of way, but in a grotesque, chaotic way. Inboxes were filled with weird, often gross content—porn spam, get-rich-quick scams, all kinds of bizarre stuff.
These days, people get annoyed by a few unwanted messages, but back then, it was overwhelming. Marketers would claim they were doing things the “right” way, but on top of that, there was this avalanche of outright garbage.
Exactly. And even back then, we heard the same excuses we hear today: “Oh, I’m not a spammer, I’m just sending this other thing!”
The problem is, if we let everyone take that stance, email becomes unusable. I remember doing the math—if you got an email from just 1% of the companies you do business with in a year, that’s already way more email than anyone wants to deal with. Now expand that to include the companies that want to do business with you, and suddenly you’re looking at hundreds of messages a day.
No one thinks of themselves as a spammer. To them, spammers are the “bad guys,” the ones sending sketchy content. But if you’re engaging in the same behaviors, even if your content is different, you’re still contributing to the problem.
That’s a great lead-in to another topic—policy compliance. Your career evolved into a focus on compliance and policy enforcement, even before “deliverability” became a widely used term. What drew you to that particular niche?
It was a natural transition from what I was already doing. Before getting into email professionally, I worked as a legal assistant for a personal injury attorney in Austin, Texas.
The intersection of spam and the law really interested me. Even though I wasn’t a lawyer back then, I understood contracts, terms of service, and how they could be used to enforce good practices. My job was to say, “Hey, your terms of service explicitly prohibit this kind of behavior, so you can take action against these bad actors.”
Sure, some companies were making money off spammers, but I could point out that if they allowed it to continue, soon spammers would be their only paying customers—because legitimate users would leave.
And now you are a lawyer! That’s a huge milestone. Congratulations on graduating from law school and passing the bar. That had to be a massive amount of work. Were there moments where you thought, What am I doing?
Oh, absolutely. Law school was tough, and I wasn’t a typical student. Many law students go straight from kindergarten to a law degree—what they call “K-to-JD.” I, on the other hand, had a 20-year break between getting my undergraduate degree and starting law school. I had an entire career in between.
That helped in some ways, but it also made things harder. When you’re young, you’re used to living on very little money. Going back to school as an adult, with a mortgage and kids getting ready for college, was a financial challenge. You suddenly go from earning a solid salary to being a student again, and when you start practicing law, you’re notcommanding those $500–$800 hourly rates right away.
But I never wanted to quit. Even when it was hard, I knew this was what I wanted.
That’s really inspiring. So now that you’ve crossed that finish line, what’s next? Who are the ideal clients for your legal and consulting services?
I have a few different areas of focus. I still do deliverability consulting, particularly around compliance and remediation—helping senders who’ve landed themselves in “email jail” and need to get back into inboxes.
It’s a lot like criminal defense work—many criminal defense attorneys were once prosecutors. Similarly, I used to be on the other side of this, enforcing policies, so I know how the system works and how to help people get out of trouble. That could mean working with Spamhaus, an ESP, or ISPs like Comcast or Yahoo.
Beyond deliverability, I’ve also done a lot of work in privacy law. I help companies—especially those looking to expand into Europe—understand stricter privacy regulations like GDPR. That might involve crafting privacy policies, helping companies understand when they need cookie banners, or advising on legal risks tied to tracking technologies like email pixels.
I also offer fractional Chief Privacy Officer services for smaller companies that need privacy expertise but don’t need a full-time CPO on staff. They might just need someone to advise their developers, sales team, or executives when privacy issues come up.
That’s fantastic. I think a lot of businesses could really benefit from your expertise.
Mickey, thank you so much for taking the time to chat today. I really appreciate it, and I hope people take the opportunity to reach out and work with you.
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