Episode #266: Ryan Caldbeck – CircleUp CEO: How To Build The Framework Of Your Life & Career

Ryan Caldbeck is the founder of San Francisco-based CircleUp, an investment platform powered by technology focused on emerging consumer and retail brands.  He went to Duke for his undergraduate degree and earned his MBA from Stanford.  He is widely known for his thoughtful “tweetstorms” on a varying degree of topics including… “For all the CEO’s who are crushing it, here are the mistakes I’ve made…” “How to hire the right people…” “Micromanaging…” And so much more. He’s one of the most thoughtful and thought provoking people I’ve spoken to…

We are hosting a workshop on developing YOUR personal excellence as a leader.  For details and availability, go to RyanHawk.me 

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The Learning Leader Show

“What we look for in a person: Horsepower, Integrity, Work Ethic, Teamwork, Pride.”

Show Notes:

  • Sustaining excellence:
    • Persistence – regardless of skill, willing to run through unlimited doors with no light at the end of the tunnel. It can be soul crushing
    • Identified focus passion – an understanding of the passion that is identifiable.
    • Drive – A motor. Really good at email and/or communication. Can’t take too long. “Have a motor.” Always moving
    • Values – “I don’t say that lightly.” You can’t sustain excellence without values. “A framework to understand you.”
  • Isn’t it hard to know what your passion is? “Yes. I got scared about the treadmill that I saw others get on.”  However, people don’t think they can leave the corporate job that pays well.  But you can.  Begin by thinking about the framework to make it happen.
  • “Silicon Valley is a hard town to talk about challenges.”
  • What it’s like to lead 60 employees
  • What mistakes were made in the hiring process?
    • “We took too long to make frameworks.”
    • “Frameworks show others what to do.”
  • What traits/values do you look for in hiring?
    • “The airport test doesn’t make sense to me. I don’t have to want to spend a day around them in the airport.”
    • “We have crystallized what we look for in a person.”
      • Horsepower – intelligence over experience
      • Integrity – don’t talk negatively about others
      • Work ethic – must be willing to work hard
      • Teamwork – need to work well with others
      • Pride – Care
  • How to gauge work ethic in a job interview?
    • “It starts with everyone knowing we are looking for that.”
  • Advice for the individual contributor making the leap to manager…
    • “Figure out framework for your specific role. Get clarity on what each person’s role is.”
    • “Learn how to develop empathy for what your team goes through. Sit with them without micromanaging them.”
    • “Make sure you have a resource (person) to talk to about being a manager. Hire a coach. Get a peer group outside of your company.”
  • Why joining The Learning Leader Circle is a good idea
  • Ryan has a coach and a group of 12 CEO’s that he meets with regularly
  • Building culture:
    • Focus on your mission
      • “To help entrepreneurs thrive by giving them the capital and resources they need.”
  • Their Values:
    • Do it right
    • Be brave
    • Be a solution
  • Constantly reinforce the vision
  • Most useful advice:
    • Winston Churchill – “Never give up.”
    • “Do what you’re passionate about”
  • How to have balance at home?
    • Two kids and his wife is a senior leader at her company
    • Mediation after the kids go to bed
    • Online working from 8:30-10:00
    • Spend time with spouse only
  • Use the “Get To Know You Document

“If you don’t keep growing, you will become irrelevant.”

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More Learning:

Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon

Episode 216: Jim Collins — How To Go From Good To Great

Episode 179: How To Sustain Excellence – The Best Answers From 178 Questions

Episode 234: Jocko Willink — Why Discipline Equals Freedom