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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.”

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