71 minutes | Feb 10, 2020

The Ryan Deiss Interview: The Godfather of Digital Marketing

Are you trying to predict what’s next in digital marketing? If you ask Ryan Deiss, effective marketing is not about being on the cutting edge. It’s about leaning into what’s working right NOW. And you might be surprised what channels matter most for growing your business in this moment.

Ryan is the Cofounder and CEO of Digital Marketer, the premiere training platform for growing your business online. Known as one of the world’s leading digital marketers, Ryan created the well-known Customer Value Optimization methodology and used it to start multiple companies around the globe. He is also the Cofounder of the Traffic and Conversion Summit, the largest digital marketing conference in North America, and Ryan is a sought-after speaker and recognized expert on marketing in the online era.

On this episode of Founders Club, Ryan joins Oliver to share his secrets for managing multiple ventures at once, discussing how his leadership team is structured and what responsibilities he outsources to an executive assistant. Ryan walks us through his journey from selling eBooks for extra money as a college freshman to CEO of Digital Marketer, describing the pivotal moment when he jotted down what has become the customer value journey—on the back of a napkin at a hotel bar. Listen in for Ryan’s surprising insight around what marketing channels are hot right now and learn how you can implement his one-page marketing plan to grow your real estate business! 

Key Takeaways

[1:09] How Ryan manages multiple ventures at once

  • Involved in day-to-day during launch, hand off to dedicated team
  • Monday leadership meetings guide how serve teams that week

[8:01] How Ryan’s leadership team is structured

  • General manager for each venture
  • Centralized specialists work across all divisions (e.g.: HR, sales)

[13:04] The role of Ryan’s virtual executive assistant

  • Matched through agency based on personality tests
  • Meet 2X/week via Zoom to go over calendar + email

[19:24] Ryan’s journey from selling eBooks to Digital Marketer

  • Freelance as web designer in college, only client paid with eBook
  • Expanded to 200 websites based on common search terms
  • Asked to speak at marketing conferences, do consulting work

[25:33] The genesis of Ryan’s famed customer value journey

  • 2006 algorithm shift led to failure, $250K in debt buying ads
  • Jot down how business gets customers on million-dollar napkin
  • Use realization to create standardization and rebuild business

[32:00] What’s hot right now in digital marketing

  • Instagram stories
  • Email newsletters

[43:11] Ryan’s insight around marketing on YouTube

  • Use retargeting for high ROI
  • Don’t break eye contact with camera

[45:17] How Ryan would approach a new real estate market

  • Put energy in product = properties know can lease
  • Create custom audience of likely tenants on Facebook, Google
  • Bring on right partners to learn and gain experience

[52:19] The habits that have helped Ryan achieve his big goals

  • Wake up at 6am, no snooze
  • Document each day in planner (evaluate big wins, lessons)

[57:12] Ryan’s advice on getting eyes online

  • Buy ads on Facebook, Instagram and YouTube
  • Advertise to CONTENT

[1:01:02] What Ryan is investing in right now

  • Put money back into own company
  • Buy art at auction (up and comers)

[1:05:56] The one thing Ryan wishes he’d known sooner

  • Better cashflow management
  • Basic business budgeting
Connect with Ryan

Digital Marketer

Ryan on LinkedIn

Connect with Oliver

Big Block Realty

Oliver on Facebook

Oliver on LinkedIn



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Traffic & Conversion Summit

Roland Frasier on Founders Club

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Perry Belcher

Dan Kennedy

Gary Vaynerchuk


The Skimm

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Morning Brew


War Room Mastermind

Atomic Habits by James Clear

Dean West





Profit First by Michael Michalowicz

Real Closers Facebook Group

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