Second Street Summit – “Building a Better Email Program”

Second Street Summit – “Building a Better Email Program”

Second Street is running a virtual summit this week focused on the topic of email newsletters.

See below for some of the ideas that stood out to us:

Session 1

June 9 at 1pm EST

“Building a Better Email Program: How to Use Newsletters to Drive Relationships and Revenue”

Dan Oshinsky

Live notes:

Why Email Works

Email is a place to engage and start a 1 to 1 conversation

Drives revenue for converting readers to paying subscribers.

Additional revenue through newsletter sponsorship, affiliate partnerships, or ticket sales.

Ways to Grow you lists

Sign up pages

Pop ups

Modules in your navigation or footer

In Article promotions

Banners or alerts

Social Media Promotions

Remnant Ad inventory

Paid Acquisition ($1 per email address)

Engagement + Capture

  1. Engage reader around a topic or issue they care about (News Quizzes, Games, Polls)
  2. Showcase the value of your work
  3. Then ask them to sign up for a relevant newsletter


  1. Let people vote on best restaurant
  2. Follow up for them to sign up for newsletter


  1. Partnership with a local business
  2. Enter to win gift card from local business for newsletter sign up


  1. Lead generation tool
  2. Good thing for editorial to get feedback on coverage
  3. “What stories do you want to see covered this month”, provide a list
  4. Email sign up

Rules for Successful Newsletters

  1. Relationships come first. Deliver on your promises (follow through on newsletter schedule). Ask readers questions and follow up with answers. Be respectful of their space and thoughtful with your interactions.
  2. Meet the moment. Re-evaluate your newsletters on a month-to-month (or even week-to-week) basis. Be willing to adjust the content or timing of a newsletter. What do readers need to hear from you right now? What do they have questions about?
    1. Weekender newsletter planned to launch preCOVID. They turned it into a Series on Gardening and other family activities at home.
    2. UTAH Eats was about going out to eat. Pivoted to cooking, groceries, and what restaurants are opening.
  3. Start with a building block. Identity (who you are, what you care about). Service (content and stories you want more of). Utility (content and stories you need more of). Personality (newsletters build around a specific voice).


Engage with your readers

  1. Ask questions and answer questions from previous days
  2. Getting readers to reply to your newsletters can improve your placement in the inbox!!!
  3. “Placement” meaning getting into the “Primary” tab and not the “Promotions” tab on Gmail.
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