The Aha Moment: Alice Kittrell

Many times when I speak to someone about their Aha Moment, they realize they aren’t the best version of themselves.

When I spoke to rockstar Alice Kittrell, she described her Aha Moment while working hellish hours in Private Equity. “I did not want to be agitated and angry all of the time.

And so, the journey began.

Before we get into the goods, a little bit about this badass.


Alice Kittrell

Alice’s resume boasts over a decade of experience in consulting and investment banking specifically in the real estate vertical. She was killing it at work, and from an outsider's perspective, on top of the world.

Things are not always what they seem.

 She was working some nights until 4 am and completely stressed both physically and emotionally. Her and her husband were also trying to start their family and the stress was weighing on her. There came a point where Alice just threw up her hands and decided enough was enough.  It was time to prioritize herself and her family. No one can do that for you but YOU!

And so begins the process of figuring out how to transition.

Making Moves…

Alice had always been interested in starting her own business. In fact, while some people keep a journal of personal thoughts, Alice was keeping a notebook of all her business ideas and working out the details of how to make it all come together.

The idea that she was most excited to pursue was an intelligent gift recommendation platform. She grew up obsessed with finding the perfect gifts for the people she loved, and more importantly seeing the joy on their faces when they opened their little surprises.

Alice began doing her due diligence and market research to understand what pain points people had in relation to gift giving. She found that the overwhelming majority  usually don't  know what to buy for others and needed help. Alice spent countless hours building out her initial MVP website, the original algorithm and a portfolio of products. 

She had a great idea brewing and it was time to start the next chapter; and so Outgift was born. But that wasn’t the only thing…

I would like to take a Zack Morris “time out” from this story to mention that on the very last day of her job in private equity, Alice and her husband received some other great news — they were expecting their first child.

Isn’t it amazing what allowing yourself to be happy will do for you?  Let that marinate.

What is Outgift?

Launched in 2016, Outgift is an intelligent gift recommendation platform that combines artificial intelligence and a highly curated product portfolio to help people find the perfect gift in under a minute. The emphasis is very much based on the quality of products and how curated and special they are; the products have to meet specific criteria, as the goal is really to recommend the best thing.

The website is extremely efficient and user-friendly. All you need to do is plug in a few details about the person and occasion, and you will have highly curated list of products to choose from, and boom — you are the heroine.


As we all know, people love to judge and criticize when big life changes are on the table. When I asked Alice if she received any judgments or criticism, she is fortunate enough to not have a lot of that in her life. She says she's actually received great constructive feedback and suggestions when it came to products on the site and ideas.

She did, however, describe an email she drafted to her entire network including friends and family detailing the plan of quitting her job and starting her new company. “I was never more scared to hit send on that email,” Alice said.

Good Vibes Only

On the flip side, Alice is extremely lucky to have two very big supporters and mentors in her life — both personally and professionally.

Alice cites a former professor at NYU, Hilary Gosher, as a big mentor to her. Hilary was an adjunct professor of entrepreneurship for a class that she was taking. At first, she was a little intimidated by how intense the class was, but over time what she took away eventually shaped her decision to take the leap and start her own startup years later.  Hilary continues to be a mentor that gives her invaluable feedback.

Alice also speaks about her husband as a big source of support and guidance for her (#awww). It's always important to have a partner who supports risk-taking in the name of happiness, and her husband has been that person for her.

Advice for the Bold

Alice loves a good algorithm so it is no surprise that she cites her biggest piece of advice from a book she read called, Algorithms to Live By. The book cites Jeff Bezos and his Regret Minimization Matrix, which invites you to fast forward your life to when you are 80 years old and to minimize the number of regrets you have.

There you have it. Take risks.

“Baby, You're a Firework…”

What gets Alice's fist pumping when it comes to getting sh*t done? Classic Katy Perry.  I mean, I think we've all had a moment or two with that song.

Hands in the air for Alice who realized she was capable of so much more and chose happiness over everything else.  Her hopes are to build a successful business that might even be one that her daughter can take over someday.

Strong women raise strong women, so I am here for that.

Do me a favor, and immediately check out Outgift because I know y'all have a party to go to where you were just going to show up with a gift card. Don’t be the gift card person.