Episode Summary: 🔥Controversial Email TAKES! Jay vs Jessica Best!!🔥

Podcast: Do This, NOT That: Marketing Tips with Jay Schwedelson
Host: Jay Schwedelson (Guru Media Hub)
Guest: Jessica Best
Date: February 13, 2026
Episode: 460

Overview

In this lively and debate-filled episode, Jay Schwedelson welcomes Jessica Best—an email marketing powerhouse with 15+ years’ experience—to challenge each other’s hottest email marketing takes. They cover practical advice for consultants, dissect common myths and mistakes in email strategy, and debate tactics from frequency to testing and send time optimization. The discussion is candid, sometimes feisty, but always rooted in real-world expertise, offering plenty of hands-on actionable tips for marketers at any stage of their journey.

Key Sections & Insights

1. Jessica Best’s Journey to Independent Consulting

Timestamps: 01:19–05:47

• Jessica’s leap from agency/client roles to solo consulting:
  • "The secret is to bet on yourself and to be a little bit more mad about what you're doing now than scared of what you're going to do next." (Jessica, 01:57)
  • She highlights 2022’s challenges (staff shortages, burnout) and encourages listeners to consider consulting either as a career or a way to stay sharp in a tough job market.
• Building a pipeline:
  • Jessica credits her speaking/teaching background for early lead-gen, “My first ripple was just going out to the people who already knew I was probably great at what I do. And that filled my funnel for about a year.” (Jessica, 04:22)
  • On the title “consultant”: Both Jay and Jessica note the importance of presentation—Jessica brands herself as a strategist and company owner instead.

2. Hot Takes Showdown: The Email Marketing Debates

Timestamps: 06:25–20:12

a. Resending to Non-Openers: Worth It or Wasteful?

Timestamps: 06:25–09:36

• Jessica's Take:
  • "Resending to non openers is crap." (06:25)
  • She argues it’s better to resend to “those who opened but didn’t click, or those who clicked but didn’t convert,” prioritizing warmer leads.
• Jay’s Rebuttal:
  • “Nobody's paying attention to anything.” He advocates for resending, but with a bold new subject line to non-openers:
  • “Oops, you missed it or yikes, you scrolled past this...” (Jay, 07:29)
  • The premise: Give people another shot, because inboxes are crowded and attention spans are short.
• Middle Ground:
  • Both agree reminders add value—the key is changing variables (like subject lines) to maximize response.
  • Jessica adds: Stretch the time between resends and control your A/B testing windows for cleaner data.

b. Testing: Can You Overdo It?

Timestamps: 09:44–13:46

• Jessica’s Take:
  • “You can over test.” (09:44)
  • Warns that constant testing isn’t worthwhile; statistically significant results are rare, especially with small lists.
• Jay’s Approach:
  • "I kind of don't care if something is statistically significant… I'm trying to inch forward… directionally, I do believe every time you hit send, you should either be testing something or revalidating a test..." (Jay, 10:16–11:16)
  • Data is volatile; use learnings directionally rather than getting bogged down by statistical rigor.
• Jessica’s Reply:
  • She’s “a big fan of putting that back into a split test or learning it again…” to build robust, repeatable insights, especially for clients with smaller lists.
  • Fun moment: Jay playfully asks about her real-life “nerd level” (12:19). Jessica admits to spreadsheeting her grocery costs.

c. Best Day/Time to Send Email: Myth or Method?

Timestamps: 13:53–17:43

• Jessica’s Take:
  • “There is no one right day of week or time of day to send an email. And that good ready content beats timing.” (13:59)
  • Calls out dated tips (“Tuesdays at 10am”) and stresses tailoring timing to user data or content readiness.
• Jay’s Agreement and Expansion:
  • He critiques the industry’s obsession with optimal timing metrics.
  • "Different people in your database interact with your emails in different ways…it’s not about which one had the highest aggregate open rate..." (Jay, 15:19)
• Send Time Optimization Tools:
  • Both are skeptical:
    • Jessica: “Open rates are kind of not quite right anymore.”
    • Jay: “Send time optimization is actually garbage.” (17:43)
  • Key critique: These algorithms rely on past behaviors that may not reflect current interests or device-driven ‘auto-opens.’

d. Email Frequency: Are Marketers Sending Enough?

Timestamps: 17:52–20:01

• Jay’s Hot Take:
  • “I don’t think people are sending out enough email.”
• Jessica’s Concern:
  • She warns that indiscriminate frequency dilutes relevance—better to focus on segmentation, automation, and personalized content.
• Jay’s Counterpoint:
  • “It's not send less, it's send better stuff. Stop being a loser.” (Jay, 19:18)
  • He argues: People will engage with frequent emails if they're valuable, not because of frequency alone.
• Shared Solution:
  • Segment and personalize so only the right people get the right emails, even if that means sending more often to engaged segments.

Notable Quotes & Memorable Moments

On Going Solo

"I have loved being my own, everything. I'm the only person that can sell my time. I'm the only person that fulfills the strategy." — Jessica Best (02:57)

On Resending Emails

"Resending to non openers is crap." — Jessica Best (06:25)

"It's all the non openers where you're hitting them in the face saying, listen, dude, you missed it and you don't want to miss this one." — Jay Schwedelson (07:29)

On Testing

"You can over test." — Jessica Best (09:44)

"I kind of don't care if something is statistically significant… if I could see something or a client could see something... let's do more of that."
— Jay Schwedelson (10:16)

On Timing

"There is no one right day of week or time of day to send an email. And that good ready content beats timing."
— Jessica Best (13:59)

"The idea of one day or time is better than another I think is really misleading."
— Jay Schwedelson (15:19)

On Email Frequency

"It's not send less, it's send better stuff. Stop being a loser." — Jay Schwedelson (19:18)

Resources, Links, and Where to Find Jessica Best

Timestamps: 20:12–20:57

• Jessica is active on LinkedIn and at her site: Jessica.Best
• Tip for consultants: Wake up your LinkedIn presence the moment you start solo.
• Jay plugs his own upcoming book ("Stupider People Have Done It") and his resources at jschwedelson.com

Takeaways for Marketers

• Consulting isn’t just a stopgap—it can be a fulfilling, scalable path if you leverage your network and differentiate your brand.
• Resending emails and frequency:
  • Approach with nuance; focus on value, segmentation, and creative subject lines versus arbitrary cadence.
• Don’t get lost in testing for testing’s sake:
  • Focus on actionable, repeatable insights over chasing statistical purity unless necessary for small lists.
• Timing myths are outdated:
  • Test, but prioritize the right message to the right audience over “magic” send times.
• Relevancy rules:
  • The success of email hinges more on content, audience fit, and clarity of purpose than on timing or sheer volume.

Episode Highlights by Timestamp

• 01:19 – 05:47: Jessica’s transition to consulting, tips for starting strong
• 06:25 – 09:36: Resending to non-openers—debate & compromise
• 09:44 – 13:46: The perils and practicality of overtesting
• 13:53 – 17:43: Debunking the “best send time” myth; skepticism on send time optimization
• 17:52 – 20:01: Is more email better? Frequency, value, and segmentation
• 20:12 – 20:57: How to connect with Jessica; wrap-up endorsements

If you work in email marketing or are considering consulting, this episode is packed with tactical wisdom, myth-busting, and real talk—skip the “rules,” stay relevant, and always keep testing... but not too much.