Podcast Episode Summary

Podcast: Do This, NOT That: Marketing Tips with Jay Schwedelson | Presented By Marigold
Episode: Ask Us ANYTHING!! 🧪 How to Convince Your Boss to TEST! ➕ Got Pooped on by a Bird 💩 | Ep. 409
Date: September 10, 2025
Host: Jay Schwedelson
Produced by: GURU Media Hub

Episode Overview

This episode features a dynamic "Ask Us Anything" format, blending sharp, actionable marketing advice with a final, more lighthearted personal story. Jay Schwedelson dives into listener-submitted questions, the highlight being strategies for convincing reluctant bosses to embrace marketing experimentation. Jay details both cultural and tactical steps to foster testing environments within teams, emphasizing the importance of innovation while tying tests to business outcomes. The episode concludes with a humorous story about an unfortunate parking lot experience, keeping the show’s signature informal and relatable tone.

Key Discussion Points & Insights

1. How to Convince Reluctant Bosses to Test New Marketing Ideas

[00:54–13:50]

The Challenge

• Listener Josh asks: How do you persuade a CEO who resists new email marketing tactics, insisting on doing things their own way?

Jay's Two-Pronged Solution

A. Create a Culture & Structure for Testing

• Highlight broader organizational benefit: The need for a culture of testing is “an overall problem” if missing, but just telling your boss that won’t work (“they're going like, later, dude” – Jay, 01:35).
• Establish a “10% Laboratory” environment:
  • Propose dedicating 10% of your database/social posts/campaigns for ongoing tests.
  • Don't frame as risky testing, but as a 10% insurance program—guarding against being left behind by more innovative competitors.
  • “We need this 10% insurance environment.” (Jay, 02:32)
• Tie innovation to business concerns:
  • Pitch the risk of “profit leakage” if you don’t test and evolve; frame experiments in terms of dollars and lost opportunity.
• Emphasize risk mitigation and the small scale:
  • “It's only going to 10% [of the audience], and then if you can show traction with that 10%, then you could win.” (Jay, 03:00–03:15)
• Measurement is critical:
  • Build a dashboard for every test: include the hypothesis, result, lift or fail to make results clear and repeatable.
  • Big enough test groups are essential—small, trivial changes (e.g., different “Webinar” subject lines) won’t show meaningful data.
  • Suggest bold A/B tests (“Free Webinar” vs. “Three Secrets to Boost ROI”) instead of minor tweaks.

B. Leverage Fear of Competition, Using AI Tools

• Highlight what the competition is doing:
  • Management responds to the threat of being left behind.
• Use modern AI tools (ChatGPT, Claude, etc.) to pull competitive intelligence:
  • Prompt examples: “Act as a competitive marketing strategist, compare [My Company] and [Competitors] across digital marketing… Highlight where our brand is falling behind… Make it simple, visual, tactical so a non-marketer executive could grasp the gaps in under two minutes.” (Jay, 05:20–06:43)
• “If it’s not even your competition, it’s who you aspire to be, have [AI] give you all this stuff and then you go back and say listen, we need a laboratory environment because this is what our competition is doing.” (Jay, 06:50–07:15)

2. Ridiculous Question Segment: Most Unhinged Parking Lot Incident

[13:52–19:48]

• Listener Dana from Long Island asks: “What’s the most unhinged thing you’ve seen in a parking lot?”
  • Jay’s relatable story: Recently got pooped on by a bird right before grocery shopping. Debated whether to go in (“I dug in my car while the stuff was, like, kind of dripping on my arm. It was so disgusting... but I said, you know what? I’m going in.” – Jay, 15:23)
• Another memorable parking lot moment:
  • Witnessed a woman yelling at a man for not returning his shopping cart. Jay reflects on his own cart habits, oscillating between “cart putter-backers” and “non cart putter backers.”
  • “I am now back on the cart putter backer team… what percentage of people are on that team? ...I’m going to go with 50%.” (Jay, 18:00)
• Invites listener responses on the cart dilemma for fun engagement.

Notable Quotes & Memorable Moments

• On pitching testing to leadership: “You want to try to establish a laboratory environment… really what you’re saying is, listen, we’re going to dedicate 90% to what we know works… this 10% ongoing is our insurance against being left behind.” (Jay, 02:09)
• On competitive benchmarking using AI: “Act as a competitive marketing strategist…create a side by side table… highlight where our brand is falling behind, where the competitor is aggressive and the easy wins we could implement immediately, keep it simple, visual and tactical so a non marketer executive could grasp the gaps in under two minutes.” (Jay, 05:43)
• On parking lot misadventures: “I got out of my car, and a bird took a deuce on me... I debated this for 30 seconds… I found an old, weird napkin, and I wiped it off. And I said, you know what? I’m going in.” (Jay, 15:17)
• On the shopping cart debate: “I am now back on the cart putter backer team... Does everybody? Am I just a horrible person? …You gotta pay it forward. Or I don’t know what I’m supposed to do, but she scared me.” (Jay, 18:13)

Key Takeaways

• Leadership Buy-in: Cultivate a “laboratory” culture, positioning testing as low-risk, high-value insurance against stagnation.
• Pragmatic Framing: Link experiments directly to revenue, profit, and competitive edge to win executive support.
• Use of AI for Persuasion: AI-powered competitive analysis can quickly, powerfully illustrate where your company is lagging versus peers.
• Bold Testing: Make tests big enough to produce actionable results; minor tweaks rarely move the needle or persuade skeptics.
• Keep Things Human: Tie in relatable, offbeat stories to build connection and encourage audience engagement.

Timestamps for Major Segments

| Segment | Timestamp | |-----------------------------------------------|-------------| | Intro & Show Format | 00:01–00:53 | | Listener Q: Convincing Boss to Test | 00:54–13:50 | | Testing Tactics: 10% Laboratory, Framing | 01:30–09:40 | | AI/Competition Benchmarking | 05:18–07:15 | | Ridiculous Q: Parking Lot Stories | 13:52–19:48 | | Takeaways, Call to Action | 19:49–End |

Episode Tone & Style

Upbeat, approachable, and a bit irreverent—Jay balances sharp marketing acumen with relatable anecdotes and plenty of humor. The practical tips are straightforward and actionable, while the personal stories foster a down-to-earth atmosphere.