Email Delivery Challenges

I once coached a rep who spent 45 minutes writing a single prospecting email. It never got opened. This is what perfectionism looks like in sales. It feels like diligence. But it's actually fear in disguise. It’s the #1 silent killer of productivity I see in top performers. And it’s keeping thousands of reps from greatness. When I ask my clients why they procrastinate on key actions—emails, calls, exec meetings—it's rarely because they’re lazy. It’s because they’re scared it won’t be “good enough.” They believe if it’s not perfect, it’s not worth doing. So they delay. They overthink. They rewrite the email 9 times. They wait until they “feel more prepared” to meet the VP. They avoid risk… and call it professionalism. But here’s the truth: Perfectionism is just fear—dressed up as high standards. And it’s costing you pipeline, confidence, and growth. The irony? You only become “good enough” by doing the reps. You don’t become a world-class presenter by sitting in Google Docs. You become one by presenting. Over and over. You don’t write powerful emails by waiting for inspiration. You get there by writing 100 bad ones first. Mastery doesn’t come from waiting until you're ready. It comes from acting before you are. The best salespeople I know are not perfectionists. They are consistent executors. They ship when it’s 80% ready. They call the VP even when they’re nervous. They send the message before second-guessing every word. They understand that competence is built through action. Not before it. Perfectionism isn’t a high standard. It’s fear of failure in a nice suit. You don’t beat it by thinking. You beat it by acting. Every single day. Done now Beats perfect never. Always.

A typo used to be a firing offense. Now it might be the most trustworthy thing in your marketing. Here's what I mean. Twenty years ago, a professor at Michigan published research showing that spelling mistakes in dating profiles were a turnoff. Last month she told a reporter the opposite: a typo now signals that you actually care, because it means a real person sat down and typed the thing. When flawless copy was expensive, perfection meant someone invested in it. Now that any brand can generate unlimited clean prose in seconds, perfection just means automation. And the data says audiences have noticed. One survey of 8,000 consumers found only 7% trust a brand MORE when its marketing looks AI-generated. 31% trust it less. That's a four to one penalty for looking synthetic. So should you start planting fake typos in your campaigns? No. And I'd push back hard on anyone who tries it. The typo was never the point... It's a proxy for something audiences actually want: proof that a person with a stake in the message made choices and hit send. The moment people figure out you're manufacturing your imperfections, you've effectively just built a more elaborate fake. The real brief for brand writing right now is simpler and harder. Write things no machine would. The best way to do that is to lean into opinions that carry some risk. References that are a little too niche. A sentence that runs long because you got bored of the short ones. Let your founder write the occasional email herself, fingerprints intact. And when a real typo slips through? Fix it in public, have some fun with it, move on. Your audience already knows the difference between careless and human. Read the full piece on State of Brand here: https://lnkd.in/gFRZaYKh

A Series A SaaS founder from Los Angeles told me last week: "𝘐 𝘸𝘢𝘯𝘵 𝘦𝘷𝘦𝘳𝘺 𝘸𝘰𝘳𝘥 𝘵𝘰 𝘣𝘦 𝘱𝘦𝘳𝘧𝘦𝘤𝘵 𝘣𝘦𝘧𝘰𝘳𝘦 𝘪𝘵 𝘨𝘰𝘦𝘴 𝘭𝘪𝘷𝘦 𝘰𝘯 𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯." He’s not alone. I’ve heard the same thing from VCs, ex-FAANG operators, even ex-McKinsey partners. They believe polish is what earns credibility. That perfect syntax builds authority. That if it reads like a press release, people will take them seriously. But here’s what they don’t realize— This mindset is exactly what’s killing their reach. Their voice sounds safe. Sanitized. Forgettable. Because when every post feels like it went through legal… It stops feeling like you. Let me be clear: Being strategic ≠ being sterile Having standards ≠ chasing perfection Thing is, We don’t trust perfect people. We trust the ones who tell the truth, even when it’s messy. Look around: → Naval’s most shared ideas are raw, unedited tweets → Melanie Perkins got more traction from rejection stories than product launches → Sahil Bloom saw 10x growth after leaning into imperfection And if that’s not enough— The data tells the same story: • Posts with imperfections + personal insight see 3.5x more engagement • Showing the “behind the scenes” drives 2–4x more private replies • Realness lowers CAC, increases trust velocity, and boosts retention So what do you really want? A post that sounds “professional”? Or one that people feel... and remember? Because here's the paradox most don't see: The more perfect you try to be… The more disconnected you become. Authority ≠ polish Authority = presence Own your voice. Let it breathe. Because the only content that scales today— Is the kind that makes people stop scrolling and start trusting. Still editing for perfection? Or is it time to speak like someone worth following?

Are you getting an F in email marketing? Your email marketing isn't broken because of iOS updates or spam filters. It's broken because you're failing on at least one of the fundamentals. What separates emails that get opened, clicked, and actually drive results from the ones that go straight to trash? It comes down to five things: 1. Know who you're talking to 🎯 Stop sending the same email to everyone. Segment ruthlessly. A targeted email to 100 people beats a generic blast to 1,000 every time. 2. Write like a human 💬 You have a personality. Your brand does too. Communicate in email the way you would speak to your prospect or customer. 3. Deliver actual value💡 Every email should make your reader smarter, save them time, or solve a problem. If you can't answer "What's in it for them?" don't hit send. 4. Make it scannable 👀 People don't read emails. They scan them. Short paragraphs. Clear headings. And don’t forget, mobile friendly! 5. Respect their inbox ✋ Consistency beats frequency. Weekly emails that deliver value beat daily emails that don't. And make it easy to unsubscribe (hiding that link just pisses people off). The brands winning at email right now aren't using fancy automation or AI wizardry. They're just doing these five things consistently. Email works. It's still one of the highest ROI channels we have. Give it the time and attention it deserves and your readers will give you theirs.

Your email marketing list has three types of people on it: Readers who never buy Buyers who never read And the 8% who do both Most brands optimize for the readers. They craft perfect subject lines, test send times, obsess over open rates. Meanwhile, the buyers are ignoring every email and just coming back when they need to reorder. Here's what nobody talks about: Your buyers don't need more emails. They need fewer, better timed ones. I pulled data from brand's ESP. Here's what we found: People who bought 3+ times had an average email open rate of 11%. People who bought once had an average email open rate of 34%. The best customers were ignoring most emails! So we split the list: Segment 1: High engagement, low purchase These people open everything but never buy. They're tire kickers. Entertainment seekers. Freebie hunters. Action: Moved them to a weekly digest instead of daily sends. One email, all the content. Stop burning domain reputation on people who aren't converting. Segment 2: Low engagement, high purchase These people buy every 40-60 days like clockwork. They ignore promotional emails. They don't care about your content. Action: Sent them exactly three emails between purchases: - Day 30: Refill reminder (just inventory check, no pitch) - Day 45: "You're probably running low" - Day 55: Reorder link, one-click Open rates stayed low (12%). Conversion rate on those three emails: 43%. Segment 3: High engagement, high purchase The golden 8%. They read AND buy. Action: These people got everything. New products first. Behind-the-scenes content. Early access. VIP treatment. The result after 90 days: Total email volume: Down 62% Revenue from email: Up 31% Unsubscribe rate: Down 55% The lesson: Stop treating your email list as ONE Your best customers don't want to hear from you more. They want to hear from you smarter. Figure out who's buying despite your emails, and get out of their way.

🔍 The Power of Imperfection: Embracing Flaws in Marketing Ever considered telling people NOT to buy your product? It sounds counterintuitive, but it might just work. Here's why: The Pratfall Effect: A psychological phenomenon where admitting flaws makes you more likable and trustworthy. 🍪 In one study, people preferred cookies with rough edges over perfect ones. 🎙️ A podcast ad saying "5 reasons NOT to listen" outperformed the positive version by 391%. Why it works: • Builds authenticity • Increases relatability • Stands out in a sea of "perfect" marketing How to implement this in your digital strategy: 1. 🧑💼 Personal Branding: Share your professional challenges alongside successes. 2. 📝 Product Descriptions: Highlight a minor flaw or limitation honestly. 3. 🖼️ Visual Content: Use "imperfect" imagery that feels more authentic. 4. 📣 Ad Copy: Test headlines that playfully discourage engagement (e.g., "5 Reasons Not to Buy Our Product"). 5. 📊 Case Studies: Include setbacks or initial failures in your success stories. 6. 📧 Email Marketing: Try subject lines that admit to imperfections (e.g., "We messed up, but here's what we learned"). Remember: The goal isn't to highlight deal-breaking flaws, but to show your human side. 💡 Pro Tip: Always A/B test these strategies against your current approach. What works for one brand might not work for another. Have you ever tried embracing imperfections in your marketing?

When "Good" Deliverability Goes Bad Many brands take pride in having great deliverability. High inbox placement, strong engagement rates, and no spam issues—it all seems like proof that their email program is working. But if deliverability is so good, why might email-driven revenue be shrinking? Marketers are often told that removing inactives and keeping lists “clean” is the key to inbox placement. While this may improve engagement rates, it can also mean cutting off potential revenue opportunities too soon. And what happens next? Businesses often replace those lost subscribers with new acquisitions—at 10–100x the cost—even though new leads are often less engaged, less profitable, and pose a bigger deliverability risk. This is The Deliverability Paradox. The real risk may not be sending too much—it may be not sending enough. Read on to explore why the pursuit of “perfect” deliverability may be costing your business millions.

Klaviyo says your revenue is up. But your bank account tells a different story. This is one of the biggest paradoxes in retention marketing. You see green numbers in your dashboard, but your repeat purchase rate is flat or even falling. Here’s what’s really happening: Klaviyo tracks who clicked and bought after an email, but it never tells you who would have bought anyway. Most of your loyal customers are already in the habit of shopping with you. If your email lands in their inbox the day before they buy, Klaviyo takes the credit. But did your campaign actually change their behavior, or did it just show up for the win? This is why so many brands celebrate “wins” in their email platform, while their actual business results disappoint. You’re measuring attribution, not incrementality. If you want to know what’s really working, you need to go beyond the dashboard. Here’s how: Split your audience into two groups. Email one group, hold out the other. Track who actually buys in each group. When you compare the results, you’ll see the real impact of your email program. Most brands are shocked by how little actually changes. The main lesson: Don’t let your dashboard tell you what you want to hear. Measure what actually moves the needle for your business.

The industry average for email marketing is $36 back for every $1 spent. So why is yours barely breaking even? I've audited 100s of email accounts across seven and eight-figure e-commerce brands. Usually the channel works fine. The problem is five things that look like normal email marketing, so nobody questions them. 1 - Chasing open rates with clickbait subject lines ↳ "You won't believe this" gets the open. Then the subscriber feels cheated, and the next time your name shows up they ignore it. ↳ It takes a long time to build trust and about 3 seconds to lose it. ↳ Fix: write subject lines that are honest and SPECIFIC. The right people will open. 2 - Writing like a corporate brand ↳ The moment your email reads like a legal team wrote it, the brain checks out.  ↳ Your subscriber's inbox is full of texts from actual friends, and then your stiff announcement lands in the middle of it. ↳ Fix: write like you're talking to one of your best friends. 3 - Cramming multiple CTAs into one email ↳ More options just freeze the reader. Psychologists call it the paradox of choice, and the brain's response to a decision it didn't ask for is to do nothing. ↳ Fix: give each email one job. Two buttons max, both pointing to the same place. 4 - Blasting your entire list ↳ Your list isn't one audience. Engaged buyers, one-time buyers, VIPs, and lapsed subscribers are all sitting in the same place. ↳ Sending all of them the same email tanks conversion, and the unengaged ones drag your sender reputation down for the people who actually buy. ↳ Fix: segment into those four groups and send accordingly. 5 - Treating email like a microphone instead of a conversation ↳ When every send is "buy now," you train your list to only open when there's a sale. ↳ Mix in educational, community, and behind-the-scenes emails and they open everything, because they don't know which one is the discount. ↳ Fix: email when you have something worth saying, not only when you want money. Clean these up and email becomes the most reliable revenue line you have.

I used to rewrite emails 12 times before hitting send. Then I realized I was optimizing for the wrong metric. Here's what changed everything: The day I stopped caring about perfect grammar: I sent a LinkedIn message with a typo to a potential business partner. Instead of ignoring it, they replied: "Finally, someone who sounds human." That "mistake" led to a huge collaboration. The truth nobody talks about: Your audience is drowning in polished, soulless content. They're craving authenticity, not perfection. What I discovered after tracking 1000+ interactions: 📊 Posts with minor imperfections: 34% higher engagement 📊 "Perfect" posts: Often ignored or forgotten 📊 Raw, unfiltered thoughts: Sparked the best conversations The perfection trap ruins more than just content: → You second-guess every decision → Opportunities pass while you're still "preparing" → Fear of judgment paralyzes action → Analysis replaces execution My breakthrough moment: Instead of asking "Is this perfect?" I started asking "Is this helpful?" Game changer. The 3-question filter I use now: -Does this solve a real problem? -Would I want to read this? -Am I adding value or just adding words? If yes to all three → Publish immediately. Here's what happens when you ship "imperfect" work: ✓ You get feedback that actually improves your next version ✓ Your audience sees the real you (they love it) ✓ You build momentum instead of building anxiety ✓ You create 10x more than your perfectionist competitors The counter-intuitive truth: The more "flawed" you allow yourself to be, the more influential you become. People don't follow perfection. They follow progress. What's one thing you've been overthinking that you could ship today? #ProgressOverPerfection #AuthenticLeadership #ContentCreation #PersonalGrowth #Productivity