Alanna Gregory

Some people think that the key to success lies within their daily routine. Do you agree with this, and if so, what is your daily routine?

I agree with this to an extent. For me, a daily routine provides some structure, which I always find helpful for starting a day productively. My morning routine is usually getting out of bed – and not checking my phone immediately– drinking a large glass of water (sometimes two) and doing some kind of workout or movement. Only once I finish this do I take time to check my email and read through a few news articles/newsletters, etc/

Looking back at your teenage years, did you have any entrepreneurial interests?

Yes, I was always pretty entrepreneurial growing up, whether it be selling things door to door, buying and selling goods for a profit, or even trading stocks. I started my first company in my freshman year of college, a fashion company with my college roommate who was interning at Nicole Miller as a designer. We raised a bit of angel capital, had a small line created and sold into a few boutiques. Ultimately, we decided to shut down the company not too long after our first collection. 

Is there a specific time of day where you feel most productive?

I’m definitely a morning person! Most productive in the mornings and/or early afternoons. 

Do you think there is one character trait/skill that is important to have in order to become a successful entrepreneur in today’s world?

Probably a combination of tenacity and resilience. You have to be able to continue on, even in the face of uncertainty, doubt, failures, or fear, and be able to maintain conviction and confidence to continue on with your vision.

 Has being a woman in the business world affected you positively or negatively, how so? 

It has probably both positively and negatively, and I may or may not have even noticed it. 

What is one major goal that you wish to achieve by 2030?

I’d love to start and build another company at some point in the future, that reaches massive scale and adoption. Not sure about the exact timelines :0 

Who is your biggest influence and why? 

Probably my parents– my mother, father, and stepfather. Each of them has taught me something whether it be work ethic and never giving up (my mother); having confidence in myself and learning from my mistakes (my stepfather) and patience (my father). 

If you could pick one female entrepreneur, who would you say is your biggest inspiration. 

I’m not sure if I’m inspired per se by any particular entrepreneur but there are certainly a few that I admire. I had the opportunity to work with Brynn Putnam at the start of MIRROR and admired her conviction, perseverance, and vision, there are few people who I’ve worked with who are quite like her; I also had the opportunity to meet Payal Kadakia early on in my entrepreneurial journey and admired her resolve, humility, and generosity.  Anecdotally, I also admire Gwyneth Paltrow; she’s quite controversial (and it’s probably controversial to even say this!) and has faced quite a bit of backlash, but despite all of that, she’s stayed true to what she believes (even if others disagree or dislike what she has to say) and has built a brand around this. 

What has been the most impressive/memorable question anyone has ever asked you?

My last boss, Eli Halliwell, asked me to tell him my life story. I was so taken aback by the question; he started off to open the conversation and ultimately was very open and vulnerable about his life, and the things that shaped him. Once he was done, it was an opportunity for me to do the same, and for him to much more quickly get a sense of me, and vice versa. 

If you have siblings are they also entrepreneurs?

No siblings! I have a step-sister who is a teacher. 

Do you think the drive to become an entrepreneur is born with or is learned?

I think it’s a mixture of both. Your circumstances can give you a certain drive and grit —a need to prove yourself— particularly if you come from a more modest background or a privileged background (wanting to strike out on your own, make your own name). But your circumstances don’t determine everything; you have to enjoy learning new things and having a sense of curiosity and level of risk.

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