The Scale Up ShowThe Scale Up Show

Top CEOs Discuss the Future of Business with AI PLUS Give Invaluable Advice for Entrepreneurs

View descriptionShare

Ryan revisits past interviews with CEOs and founders Matthew Tillman of Open Envoy, Doug Dennerline of BetterWorks and Joao Ferror Dos Santos who is running a 30-day experiment making ChatGPT the CEO of his new company Aesthetic Apparel. They discuss leveraging AI to grow companies, best practices for leading teams, the future of HR tech, and more. With over 20 years in machine learning and experience scaling multiple companies, these guests provide valuable insights for entrepreneurs looking to build successful businesses.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here:


  • Commoditization of AI through open-source tools allows start-ups to leverage advanced technology like computer vision more easily.
  • Building a strong team that challenges the status quo daily is crucial for any high-growth company.
  • As a founder, you must recognise what things are worth delving into deeply and what ideas and thoughts need to be put ‘on the back burner’. Investigating and getting involved in anything to do with your business can be too easy as you have so much passion for it.
  • Focus on your business and what you can do more of today to grow it.
  • Customer feedback is always an opportunity, the information you get is invaluable.
  • AI will transform HR by eliminating bias and repetitive tasks so managers can focus on developing employees.
  • The rapid advancement of AI demands more ethical guidelines and oversight to match the pace of technological innovation.
  • Turning AI experiments into real businesses requires thoughtful strategy while preserving what makes the story compelling.


"Math is totally commoditized and free. I'm an investor in Stability AI. If this human is being treated like a robot, let's find them some value add work to do." - Matthew Tillman

“You optimize towards customers that will love you and refer you” - Matthew Tillman

“The reality is machines do this black and white input better than you can handle it” - Matthew Tillman

"I want smart, hardworking people that have an opinion, that come to the company and challenge it every day and have fun doing it." - Doug Dennerlein

“The hardest people worked for me was when I was able to connect the corporate goals to individual goals, both personally and professionally” - Doug Dennerlein

“I have a very low ego environment in my company and I don’t believe in lines”- Doug Dennerlein

“I want to create content that I will respect, I don’t want to use templates to sound like everyone else” – Joao Ferrao

“We are disrupting basically almost everything and the reality is it’s a big double-edged sword”- Joao Ferrao

“Technology is accelerating ahead of our emotions” - Joao Ferrao

Ryan Staley

Founder and CEO

Whale Boss 

  • Facebook
  • Twitter
  • WhatsApp
  • Email
  • Download

In 1 playlist(s)

  1. The Scale Up Show

    375 clip(s)

The Scale Up Show

How do you grow like a VC backed company without taking on investors? Do you want to create a lifest 
Social links
Follow podcast
Recent clips
Browse 375 clip(s)