Trailblazing in Style
Episode 10
July 14, 2020

Trailblazing in Style

With Brian Ree, Co-Founder & CEO of DAILYLOOK

DAILYLOOK is a personal styling service that sends you a box of hand-picked fashion items right to your door every month. In this interview, Brian shares with us how he started his first business at 15 years old, created and then sold a newsletter with over 450k subscribers to a poker company, and then raised over $11M to build his company DAILYLOOK. Brian uncovers the challenges he faced from pivoting his business and shares some important red flags he looks out for when hiring.

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In This Episode You’ll Hear About:

  • How Brian Ree started his first tutoring business in high school
  • How the internet boom inspired an idea for an online fine jewelry lifestyle brand
  • How a hobby turned into a content business and developed 450,000 active subscribers
  • Why studying and reading about other entrepreneurs and finding patterns is an important part of the entrepreneur’s journey
  • How he came up with the idea for DAILYLOOK
  • The challenges he faced from pivoting DAILYLOOK into an eCommerce brand
  • His process of choosing a business model that would drive customer retention organically
  • What he learned from making the best,and worst, hiring choices 
  • The ins and outs of raising $11.5 million of capital
  • How his Co-Founder helped the company be as successful as they are today
  • The importance of physical health in building a business
  • Experiencing self-doubt as an entrepreneur and how to overcome it 

To Find Out More:


  • “I think there's a lot to be gained in experience from working with great teams and great people.”
  • “I definitely recommend having and surrounding yourself with as many experienced mentors as possible.”
  • “People that didn't have positive experiences with other coworkers in previous jobs will still tend to give a mediocre or medium type of reference check.”
  • “When you start a business, I do recommend that, depending on the business of course, that you have a co-founder.”
  • “I think the mental game is a challenging one. And with time and experience, I've learned my ways of how I cope with things in challenging times.”
  • “As an entrepreneur, self-doubt can creep in from many different angles and places and times.”
  • “I try to maintain the perspective and mindset of being a lifelong learner and always intellectually curious and open to learning new things. Learn from new people around you.”

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