077: Darrell Vesterfelt – Running a 101,000-Person Online Summit

077: Darrell Vesterfelt – Running a 101,000-Person Online Summit

Author: Nathan Barry: Author, Designer, Marketer May 22, 2023 Duration: 1:03:35

Today, I talk to Darrell Vesterfelt, who is a longtime friend who helped grow ConvertKit in our craziest growth times (from $100,000/mo when he joined to $500,000/mo in just over a year).

Darrell is one of the best marketers I know. He is the Founder and former CEO of Good People Digital, the Co-Founder of Homestead Living, and Co-Founder and COO of the School of Traditional Skills.

In this episode, Darrell breaks down the goal and execution of an online summit that accumulated an astonishing 101,000 attendees as a brand-new brand! Tune in to find out why you can’t have a marketing strategy without value and vice versa.


In this episode, you'll learn:

  • Darrell’s transition from New York to homestead; how his marketing skills translate to homesteading.
  • The importance of authenticity in the homesteading world.
  • A rundown of Darrell’s various businesses.
  • The publication and publishing house, Homestead Living: what inspired it and where it’s going. 
  • The structure, marketing strategy, execution, and conversion rate of the School of Traditional Skills Summit.
  • The best marketing strategy according to Darrell.


Links & Resources:

Homestead Living

Homestead Living on Instagram

School of Traditional Skills

Homesteading Family

Good People Digital

Everything Worth Preserving


Darrell Vesterfelt Links:

Darrell’s website

Follow Darrell on LinkedIn

Follow Darrell on Twitter

Follow Darrell on Instagram


Dive into the archives of Nathan Barry Archive, a collection of insights from an author and designer who traded pure aesthetics for the gritty, rewarding work of building things. Nathan Barry’s journey from design into the world of product launches and self-publishing forms the core of this conversation. You’ll hear frank discussions that treat marketing not as a mystery, but as a practical craft, and explore what it genuinely takes to create a sustainable online business. The topics naturally span from the tactical details of launching a book to the broader principles of designing a life that isn't just profitable, but also fulfilling. This isn't about abstract theory; it's a recorded chronicle of applied knowledge, filled with lessons learned from real successes and stumbles. For anyone curious about the intersection of creativity and commerce, this podcast offers a long-form, thoughtful perspective. Tune in for episodes that feel like a series of focused conversations with a practitioner who is deeply invested in the process, not just the outcome. The Nathan Barry Archive serves as a valuable resource for designers, writers, and founders looking to navigate their own path toward building something meaningful on their own terms.
Author: Language: en-us Episodes: 78

Nathan Barry Archive
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