Cold Email: Lessons from Real Outbound Campaigns in 2025

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May 26, 2025

Guest

Alex Fine

Join industry experts Will Allred, Co-founder of Lavender; Zoe Hartsfield from Apollo; Maximus Greenwald, CEO at Warmly AI; and Alex Fine, Co-founder of Understory, as they explore the art of cold emailing. They dissect common pitfalls that lead to failed campaigns and highlight the importance of personalization over automation. From timing strategies to engaging subject lines, they tackle real-life email disasters and share actionable tips for crafting compelling outreach. Discover the secrets to making your cold emails stand out!

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ADVICE

Focus on Recipient's Problems

Focus your cold emails on the recipient's pain points, not yourself.
Avoid talking about yourself first; instead, solve problems the recipient cares about.

ADVICE

Tier Your Email Outreach

Use tiering to decide when to automate versus personalize cold emails.
Do manual outreach for tier-one perfect-fit accounts to improve response.

ADVICE

Right Person, Message, Timing

Send cold emails only to the right person, with the right message, at the right time.
Avoid sending bulk mass emails that are irrelevant and risk your company reputation.

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#249 Cold Email | In this episode, Danielle is joined by four experts in B2B outbound: Zoe Hartsfield (Apollo), Will Allred, (Lavender), Maximus Greenwald (Warmly), and Alex Fine (Understory). Together, they dive into the good, bad, and “please don’t ever send this” of cold email strategy. Each guest brings firsthand insight from scaling outbound at fast-growing B2B companies and helping clients do the same.

Danielle and the crew cover:

The biggest reasons cold emails flop and what great ones do differently
How to use personalization, targeting, and timing to get replies (not unsubscribes)
The right way to blend automation and human touch in your outbound strategy

It’s an inside look at how marketers and founders approach outbound messaging, across strategy, execution, and scale.

Timestamps

(00:00) - — Intro and guest lineup
(03:38) - — Why most cold emails fall flat
(05:38) - — Common copy mistakes: too much “I,” not enough “you”
(07:08) - — The automation vs. personalization debate
(09:23) - — When *not* to send a cold email
(11:38) - — What targeting gets wrong (and how to fix it)
(13:38) - — Teardown #1: Robotics email with 0% replies
(15:53) - — Subject line issues, tone, and CTA feedback
(18:08) - — Teardown #2: CRM campaign with profanity
(19:53) - — Why this email screams “marketing,” not “outbound”
(23:19) - — Teardown #3: Direct debit email repurposed from a nurture
(25:49) - — Why HTML-heavy emails kill deliverability
(27:34) - — Teardown #4: Founder-led cold email from Breakout
(29:49) - — What worked: relevance, format, and intent
(32:19) - — Teardown #5: Cybersecurity email to bank execs
(34:19) - — Final takeaways on relevance, timing, and strategy

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