Future Commerce

Stairway to CEO: Trailblazing in Style with Brian Ree, Co-Founder & CEO of DAILYLOOK


Listen Later

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.

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:

    dailylook.com

    Quotes:

    “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.”

    futurecommerce.fm/stairwaytoceo


    Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    ...more
    View all episodesView all episodes
    Download on the App Store

    Future CommerceBy Phillip Jackson, Brian Lange

    • 4.9
    • 4.9
    • 4.9
    • 4.9
    • 4.9

    4.9

    83 ratings


    More shows like Future Commerce

    View all
    The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch by Harry Stebbings

    The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

    534 Listeners

    The Knowledge Project by Shane Parrish

    The Knowledge Project

    2,705 Listeners

    Shopify Masters by Shopify

    Shopify Masters

    378 Listeners

    The a16z Show by Andreessen Horowitz

    The a16z Show

    1,091 Listeners

    How I Built This with Guy Raz by Guy Raz | Wondery

    How I Built This with Guy Raz

    30,193 Listeners

    Y Combinator Startup Podcast by Y Combinator

    Y Combinator Startup Podcast

    227 Listeners

    Morning Brew Daily by Morning Brew

    Morning Brew Daily

    3,015 Listeners

    Uncensored CMO by Jon Evans

    Uncensored CMO

    48 Listeners

    All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

    All-In with Chamath, Jason, Sacks & Friedberg

    10,018 Listeners

    Dwarkesh Podcast by Dwarkesh Patel

    Dwarkesh Podcast

    516 Listeners

    The Artificial Intelligence Show by Paul Roetzer and Mike Kaput

    The Artificial Intelligence Show

    197 Listeners

    ACQ2 by Acquired by Ben Gilbert and David Rosenthal

    ACQ2 by Acquired

    299 Listeners

    No Priors: Artificial Intelligence | Technology | Startups by Conviction

    No Priors: Artificial Intelligence | Technology | Startups

    130 Listeners

    OPERATORS by OPERATORS

    OPERATORS

    50 Listeners

    Prof G Markets by Vox Media Podcast Network

    Prof G Markets

    1,426 Listeners