Master Cold Email Outreach and Generate Sales with Adam Rosen

Topics discussed in this episode with time stamps

00:00 – 00:46 “Well, when it comes to email, there’s no true silver bullet. Everyone’s always looking for that one thing that’s going to get you this amazing reply rate or meetings booked or open rate or this or that. And the reality is it’s about doing a bunch of things well that give you a 1% to 3% lift on each of those things. But at the end of the day, it still comes to what’s the offer. Like, you know, the old saying: at least I did some real estate development, and specifically land development. And one of the things you’d hear quite a bit is you can put lipstick on a pig, but at the end of the day, it’s still a pig. So when it comes to marketing, it’s like we can do our best to make any offer sound as good as possible. But at the end of the day, the offer is what the offer is.” — Adam Rosen

00:47 – 01:04 Welcome to Peppershock Media’s Marketing Expedition Podcast

01:05 – 02:08 Adam’s Background

02:09 – 06:06 Marketing Essentials Moment: Cold Email Outreach

06:07 – 08:08 Welcome to the show, Adam!

08:09 – 10:08 Success Stories: Working with Big Brands

10:09 – 14:00 Common Mistakes in Cold Email Outreach

14:01 – 15:55 The Importance of Patience in Marketing

15:56 – 18:12 Lead Generation and Newsletters

18:13 – 23:10 Capturing First-Party Data Effectively

23:11 – 23:48 Poderific, baby! Whether you’re looking for a podcast studio to rent or need help with the entire production and distribution of your podcast, we gotcha covered. 

23:49 – 27:37 Tools for Email Management

27:38 – 29:06 Timeline for Setting Appointments

29:07 – 31:09 Booking Meetings

31:10 – 33:36 Opt-In vs. Opt-Out: Which is Better?

33:37 – 37:47 Getting Started with Cold Email Outreach

37:48 – 38:25 Reach out to Adam

38:26 – 38:54 Thank you so much, Adam! Share this podcast, give us a review, and enjoy your marketing journey!

38:55 – 39:42 Join the Marketing Expedition Community today!

Like what you hear, but need more information?

Meet with Rhea Allen

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READ THE FULL TRANSCRIPT

Podcast Intro

Welcome to the Marketing Expedition podcast—an auditory journey through the latest in marketing, branding, and advertising. Now, here’s your Marketing Expedition guide, Rhea Allen.

Rhea Allen: On this episode, I get to speak with Adam Rosen. He’s a world-traveling entrepreneur who sold his first tech startup in 2019.

Rhea Allen: Adam currently leads EOCWorks.com (Email Outreach Company), an email marketing agency helping startups, unicorns, and Fortune 500s generate sales through email. Having exited multiple businesses and led multi-million-dollar real estate developments, Adam now enjoys the freedom of building successful ventures while exploring the world’s most inspiring places.

Rhea Allen: Today we’re talking cold email—how startups can use it to generate sales, how to set it up, and the tools Adam recommends. When you’re ready to level up, you can work with his team. He shares a ton of practical advice, so you’re in for a treat.

Rhea Allen: But first, it’s time for your Marketing Essentials Moment—the basics you need to keep building your brand and your bottom line.

Marketing Essentials Moment: Cold Email Outreach

Rhea Allen: Since today’s episode is all about cold email outreach, I want to dig into why you’d use cold outreach and how to think about it strategically.

Rhea Allen: Cold outreach isn’t about spamming strangers. It starts with targeting: identifying exactly who you want to reach and why.

Rhea Allen: Here are a few smart reasons to use cold outreach:

• Pipeline insurance: Referrals are great, but cold outreach helps you build consistent opportunity.

• Market feedback: Test messaging, offers, and hooks with real-world responses.

• Relationship-building: Lead with value, not a hard sell.

• Offer testing: Try ideas with a small group before scaling.

Rhea Allen: Instead of leading with “Here’s what I sell,” start with something useful: a case study, a swipe file, a template, a checklist, or a short personalized video.

Rhea Allen: You can also use cross-promotions to expand reach, seasonal hooks tied to events, and simple calls-to-action that make it easy to say yes or no.

Rhea Allen: The goal is relevancy, micro-value, and permission-based nurturing beyond the first email.

Rhea Allen: Now, let’s get into the interview.

Interview: Adam Rosen

Rhea Allen: Welcome to the Marketing Expedition podcast. I’m your host, Rhea Allen—President and CEO of Peppershock Media and founder of the Marketing Expedition community.

Rhea Allen: Today’s guest is Adam Rosen. Welcome to the show, Adam.

Adam Rosen: Rhea, I appreciate you having me.

Rhea Allen: We get to talk marketing today, but first, share a little about your background and how you got here.

Adam Rosen: I’ve never held a true nine-to-five. I started my first company right out of college. I did a one-year MBA, then launched my first business about a month before graduating.

Adam Rosen: I ran that business for about five years and sold it in 2019. We did a million things wrong as a startup, but we always did one thing exceptionally well: getting new customers.

Adam Rosen: We landed some of the biggest brands in the world—Amazon, Apple, Goldman, Disney, BlackRock—and we got most of them through cold email. We also raised money through cold email, and even found the company that acquired us through cold email.

Adam Rosen: After the exit, I started advising startups. One founder told me his team was struggling to get meetings booked. I talked with his head of sales and saw a big gap in their email strategy.

Adam Rosen: I called my co-founder from the previous company and said, “I think we can help.” That startup became our first customer almost five years ago.

Adam Rosen: Since then, we’ve worked with about 200 companies—from early-stage startups to brands like the UFC, Allstate, and Zapier—helping power their go-to-market function, specifically on the email side.

Rhea Allen: That’s impressive. What’s one win you’re especially proud of?

Adam Rosen: When it comes to email, there’s no silver bullet. Everyone wants the one thing that drives reply rates, meetings booked, open rates—whatever.

Adam Rosen: The reality is: it’s a bunch of small improvements that each give you a 1–3% lift. But at the end of the day, it still comes down to the offer.

Adam Rosen: I used to do real estate development—land development specifically—and there’s an old saying: you can put lipstick on a pig, but it’s still a pig.

Adam Rosen: In marketing, we can make an offer sound as good as possible, but the offer is still the offer.

Adam Rosen: I love helping early-stage startups. It’s fun to work with big brands—like going to UFC fights, getting brought into the octagon, and seeing sponsors we helped them land. But helping a startup get their first customers is always the proudest moment, because I know how hard that is.

Rhea Allen: What are the most common mistakes people make with cold email outreach?

Adam Rosen: Number one: treating email in 2026 like it’s 2017—or even like it’s 2023. The playbook has completely changed.

Adam Rosen: The biggest issue is infrastructure. One of my favorite quotes is: “You can’t hit what you can’t see.” If you land in spam, you don’t stand a chance—no matter how good your offer, copy, or list is.

Adam Rosen: Most people still don’t realize you shouldn’t do outbound emailing from your primary domain.

Adam Rosen: The other cringey thing is bait-and-switch. People promise “50 meetings in your first month or you pay nothing,” then you get on the call and realize it was basically BS. They only said it to get you on the phone.

Rhea Allen: I see that a lot—LinkedIn DMs, emails—big promises that feel too good to be true.

Adam Rosen: When it sounds too good to be true, it usually is.

Rhea Allen: You mentioned Amazon and Apple earlier. How did you get to a point where you could cold email for brands like that?

Adam Rosen: Those big brands were customers of my first startup. We built a two-sided marketplace with about 100,000 student organizations across the U.S. and their members.

Adam Rosen: We sold into big brands that wanted to recruit those students and run surveys through our platform.

Adam Rosen: It showed the power of email. We raised money through email, sold the company through email, got most of our users through email, and landed big customers through email.

Adam Rosen: Email is just a highway connecting party A to party B.

Rhea Allen: What works for one company won’t always work for another.

Adam Rosen: Exactly. And patience wins.

Adam Rosen: There’s a reason the tortoise and the hare is a classic story. The older I get, the more I understand my mentors: they’re patient. They hold people accountable, but they don’t panic.

Adam Rosen: I see leaders pull out after three days because something didn’t work. I’ve talked to founders who’ve worked with six agencies for two months each. At some point, you have to look in the mirror.

Adam Rosen: Is the offer not strong enough? Is the ICP wrong? Or did you never give anyone enough time to prove it out?

Adam Rosen: You shouldn’t stick with something that’s clearly not working forever—but a lot of the gold is on the other side of patience.

Rhea Allen: What elements do you help companies with—lead gen, newsletters, and more?

Adam Rosen: Our bread and butter has always been outbound—cold email.

Adam Rosen: In January 2024, my business partner, my sister, and I bought a newsletter. For years, I lived as a digital nomad—Amalfi Coast, South of France, Hawaii—building the business.

Adam Rosen: We found a digital nomad newsletter with about 5,000 subscribers. We bought it, grew it to a quarter million subscribers, and grew revenue from zero to about six figures a year.

Adam Rosen: We sold it for a decent profit after about a year.

Adam Rosen: The bigger win was that it opened a new vertical for us. Now we build newsletters—both ones we own and monetize, and ones we build for clients.

Adam Rosen: Newsletters help clients become thought leaders and nurture leads. In today’s world, we’re crushed with ads all day. People go to the voices they trust.

Adam Rosen: We also do a lot on LinkedIn, and we’ve bought a few smaller businesses to open new verticals. But outbound is primarily email and newsletters.

Rhea Allen: Growing lists is fascinating. First-party data is critical. What tactics help capture it?

Adam Rosen: A big problem is irrelevant content.

Adam Rosen: For example, one newsletter we have is for CFOs. We target CFOs and financial leaders, and the content is built for what they actually care about.

Adam Rosen: Too many newsletters are just sales pitches. The harsh truth is: nobody cares about your new product launch.

Adam Rosen: People care about what’s in it for them. Can they learn something? Can you help them grow their career?

Adam Rosen: Most newsletters are “I, I, I.” They should be “you, you, you.” That’s how you get subscribers and keep them engaged.

Rhea Allen: Do you use surveys or polls to capture info?

Adam Rosen: Surveys are great.

Adam Rosen: In my first startup, we became a survey platform collecting data on Gen Z and the future of work. I did keynotes using that data: what kind of office Gen Z wants, leadership styles they prefer, companies they avoid.

Adam Rosen: But you have to make it compelling. Why would someone fill out the survey?

Adam Rosen: We paid student groups based on how many surveys their members completed. We gave away about $300,000 to student groups to fund initiatives.

Adam Rosen: In return, students signed up so companies could recruit them, and we collected valuable data we could use to create more demand.

Rhea Allen: You said earlier not to use your primary domain for outbound. Explain why.

Adam Rosen: In the old days, we’d send thousands of emails a day from our primary domain and it wasn’t a big deal.

Adam Rosen: Over the last few years, Google, Yahoo, Zoho, Microsoft—everyone—has cracked down to stop mass emailing and spam.

Adam Rosen: Now you can really only send about 10 outbound emails per day from your primary inbox. If you send more, you get flagged.

Adam Rosen: But to do marketing, you need scale. If you want to send 100 emails a day, you need about 10 inboxes. If you want to send 1,000 a day, you need about 100 inboxes.

Adam Rosen: And you never want to risk your primary domain health. If your domain gets blacklisted, everyone at your company is more likely to land in spam—even when emailing real customers.

Adam Rosen: Our primary domain is EOCworks.com. We don’t send outbound from it. We use hundreds of variations instead.

Rhea Allen: I didn’t realize 10 emails a day could be the trigger. That’s valuable.

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Interview Continued

Rhea Allen: How do you manage so many inboxes? Are there tools you recommend?

Adam Rosen: It’s not as cumbersome as it sounds.

Adam Rosen: You send as if it’s one inbox, and replies route into one central inbox.

Adam Rosen: My team manages around 20,000 inboxes across our customers. You’d think we’d need 50–100 people. We have five dedicated inbox management people.

Adam Rosen: The tool we love—especially for beginners—is Instantly at instantly.ai.

Adam Rosen: You can get lists, send campaigns, and manage replies. We send about half of our 2 million emails per month through Instantly. Their support team is great.

Rhea Allen: They should pay you for that plug.

Adam Rosen: I’m happy to promote products I genuinely love.

Rhea Allen: What about warming up new inboxes?

Adam Rosen: Great point. You don’t want to create a new domain today and start blasting emails.

Adam Rosen: You should warm it up for at least three weeks. Most platforms—including Instantly—have warmup tools that mimic sending so Google sees consistent, legitimate behavior.

Adam Rosen: If you skip warmup, you’ll almost certainly land in spam and your domain will be burned from the start.

Rhea Allen: How long does it usually take to book the first appointment?

Adam Rosen: As quickly as possible, but it depends.

Adam Rosen: Some customers don’t book a meeting for two months, then the floodgates open. Others get hot right away.

Adam Rosen: The biggest factors are: how well you know your market, how clear your offer is, and how close you are to email-message fit.

Adam Rosen: For most companies, you should be able to book a meeting in the first two weeks.

Rhea Allen: Do you use booking links like Calendly?

Adam Rosen: Yes—Calendly is the most frictionless.

Rhea Allen: Sometimes people resist booking links and just send availability. Do you see that?

Adam Rosen: It’s rarer each year. People are more comfortable with it.

Adam Rosen: That said, it depends on the market. We have a large real estate development client selling raw land to an older demographic in rural Texas, Alabama, Florida, and more. For them, we schedule manually—often getting a phone number and having sales call.

Adam Rosen: If someone emails back with a time, my team will check the client calendar and manually book it to remove friction.

Rhea Allen: That makes sense, especially with generational preferences.

Adam Rosen: Even for me, sometimes I’ll just say, “Here’s my number—call me.”

Adam Rosen: I miss the old days of phone calls. Zoom is great for sharing decks and pricing, but phone calls often feel more efficient.

Rhea Allen: Opt-in versus opt-out—what’s better?

Adam Rosen: It depends.

Adam Rosen: If you want quality over quantity, opt-in is better.

Adam Rosen: If you believe you can win people over with content, opt-out can work. Neither is inherently wrong.

Rhea Allen: For someone getting started, what’s the basic process for launching a cold email campaign?

Adam Rosen: First: do a gut check. Are you ready to do marketing at all?

Adam Rosen: Marketing brings feedback—sometimes harsh.

Adam Rosen: I’ve done Facebook ads where I’d film myself on a property and put money behind it. During COVID, someone commented, “I hope you get COVID and die.”

Adam Rosen: I stayed kind, we went back and forth, and by the end he apologized and said he’d grab a beer with me. He was having a rough day.

Adam Rosen: The lesson: don’t take feedback too personally—good or bad. The same email can get “best email ever” and “worst email ever” within five minutes.

Adam Rosen: People are reacting based on what’s going on in their life.

Adam Rosen: Tactically, here’s the simple setup:

• Build infrastructure (don’t overpay for inboxes)

• Buy 50–100 inboxes

• Warm them up for three weeks

• Connect them to Instantly

• Pull a list (Instantly’s lists aren’t perfect, but good enough to start)

• Launch a campaign and send

• Do two follow-ups

• Use spin tax so every email isn’t identical

• Manage replies

Adam Rosen: It’s not the most advanced setup, but it gets you in the game. Then you can improve from there.

Rhea Allen: If someone wants to take it to the next level, how do they reach you?

Adam Rosen: Great segue, Rhea.

Adam Rosen: Go to eocworks.com to learn more. You can also email me at  adam@eocworks.com . I’m happy to answer questions, and I’m open to a quick Zoom or phone call to see if we can help.

Rhea Allen: Thank you, Adam. This is a whole world—cold outreach, email, newsletters—and you shared a ton of value.

Adam Rosen: Rhea, I appreciate you having me on. Thanks for the great work you’re doing.

Rhea Allen: And with that, the best thing you can do for Adam and me is share this episode with someone who needs it, and leave us a review.

Rhea Allen: Until next time—enjoy your marketing journey.

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