Libby Crow shed her shadow and built an empire. Now she shares her shine.
10 min read
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In 2012, Libby Crow received a phone call from a woman selling renters insurance. Little did she know that the seemingly mundane conversation with a stranger would save her life.
Crow was 25 years old. She had just dumped her boyfriend, quit her elementary school teaching job to become an entrepreneur, and moved to Denver, Colo., for a fresh start. Renters insurance seemed like a reasonable precaution — but she didn’t plan on living long enough to need it.
As she listened to the woman explain policy options, Crow repressed the pain of her father’s recent death, the loneliness of being a digital business owner, and the dark thoughts that had recently emerged in the vacuum of leaving her old life behind. Crow had already penned a goodbye letter to her mother, complete with banking account numbers and passwords. She was on the verge of giving up hope.
Despite this, Crow remained calm and polite on the phone. That wasn’t hard for her: an honors student, prom queen, and star athlete, she was a natural performer. As the conversation came to a close, the stranger on the line said something that would change the course of her life.
Today, Crow runs a thriving global coaching business. She lives in sunny Venice Beach, Calif., with her husband, fellow entrepreneur Scott Oldford, and their long-haired dachshund, Cooper. The woman who had once lost the will to live can now be described as a human sparkler: one encounter with her will light you up.
At just 31, she’s mentored thousands through her online courses, group coaching programs, one-on-one consulting sessions, workshops, and retreats, teaching them how to effectively build and run online businesses.
The present-day Crow is a far cry from the small-town Wyoming girl who started her career as an overworked, underpaid teacher, numbing the grief that would eventually threaten her life and grasping at a dream that then seemed impossible.
Living from taquito to taquito.
“Where I grew up, you’re expected to go to college, get married, take a vacation once a year, and pay off your debt until you’re 60,” says Crow.
A dutiful daughter and emotional rock for others, Crow followed the script. After graduating from college, she promptly took a local teaching job making $2,200 a month to start paying off her $60,000 of student loans. While she did her best to make it work financially, she ate her fair share of 32-cent packs of ramen noodles and $2 taquitos to stay afloat.
All the while, a greater longing stirred inside her. “Even though I loved teaching, my gut told me I was supposed to be doing something else,” shares Crow. Grateful to be employed, she resigned herself to simply scraping by.
Then, Crow’s father died of alcoholism.
“My dad’s death shook my whole world. I started to wonder — if that’s how fast your life can be taken, what’s it all really for?” The tragedy led her to explore another path in life.
Life outside the box.
Crow says she is empowered by others’ breakthroughs, so it’s fitting that a girlfriend’s success inspired her to make a change. “I was on Facebook one day and saw a friend’s transformation story. She changed her lifestyle, started a business, and was glowing,” says Crow.
“At the time, I was feeling pretty unhealthy and wanted to shift my energy and habits. I reached out to this friend, and she became my wellness coach.”
The experience opened up Crow to the world of transformation and what was possible for her own life. She dove fully into entrepreneurship herself and over a short time matched her teaching salary and developed a lucrative side hustle.
Still, Crow avoided processing her father’s death by working around the clock. She would come home from her day job at school and stay up late into the night learning coaching skills. “I’d watch videos by business coaches like Brendon Burchard or Jeff Walker until 3 a.m. to escape from grieving,” admits Crow. “But it also gave me direction. I saw what they did with their online businesses and knew I could do it too.”
By working around the clock, Crow avoided processing the pain of her father’s death.
Image Credit: Libby Crow
Crow decided to quit teaching and invest all her time in building her own consulting business. It was risky, but she believed in herself. She needed to — because no one else would.
“A lot of people told me I shouldn’t go for it, that I needed a secure job with health insurance, or that I’d be back teaching by the following year,” remembers Crow.
Instead of heeding her critics’ advice, she took the leap. “I started to succeed externally, but with time and space away from the nine-to-five, all these feelings came up. I finally had to face them.” For Libby Crow, processing the grief of her father’s death would prove to be a reckoning.
An atheist’s prayer answered.
Months later, the feelings she kept shoving down had spiraled into a state of unmanageable depression. Crow sat huddled on the floor of her new home, with a broken heater in the dead of Colorado winter, surrounded by floor-to-ceiling boxes she was too overwhelmed to unpack.
A broken heater, floor-to-ceiling boxes, and an uncertain future left Crow overwhelmed
Image Credit: Libby Crow
She was afraid of the future and of how much energy and grit it was going to take to succeed. She felt alone and was exhausted from running from the grief of her father’s death.
“I remember just feeling like I was done: done having it together for everyone else; done having to push so hard to make a living. I thought maybe not being here would be easier.”
Crow had never been the praying type, but that night she made an exception. “I wasn’t spiritual at all at the time, but I asked ‘God’ to give me a sign that I shouldn’t die. I needed something, and I didn’t know what to do.”
The next day, Crow was driving down a mountain in Colorado when she received the phone call from the woman selling renters insurance. “Oddly enough, it was near one of the cliffs in the big canyon where I was considering ending it all.
“I wanted to hang up, but she was really nice. So, we had a whole conversation about the benefits of insurance,” says Crow. “The whole time I’m thinking, ‘This doesn’t really matter.’”
Then, out of nowhere, the stranger said, “This is going to sound odd, but I need to tell you about something. There’s this place in Denver that I think you might want to go to. It’s like a church, but don’t get freaked out. It’s kind of like where you’d go if you were a yogi.”
Crow listened, skeptical. Then something clicked. “Maybe this is the sign I prayed for,” she thought. “But then the atheist part of me was like, ‘Nah.’”
Nonetheless, Crow decided to give it a chance. “I looked up the place and dragged myself in there. I remember thinking, ‘Libby, you know you’ve hit rock bottom when you’re listening to the renters insurance lady for critical life advice.’”
That day was a turning point for Crow. It was when she finally let herself start to process the grief of her father’s death. It was also the day she recommitted to her journey of personal growth and full responsibility for creating the life she wanted. “The experience led me on my spiritual path. A path of self-love and self-care that inspired my company at the time.” Through Crow’s personal reckoning and new direction, her consulting business began to boom.
From personal healer to business mentor.
Crow let her inner transformation inform her business and what she created for her audience. She returned to her roots as a teacher, pivoting her business model from a healing one to a teaching one. “My first business model focused on helping other women overcome personal challenges that were holding them back,” she explains. “After years of leading clients in transformation and creating multiple successful businesses, I pivoted toward teaching new entrepreneurs how to build their own businesses online.”
Since then, she’s built a fleet of programs to teach skills ranging from social media management to list building and structuring your online business so it runs itself. She now focuses on helping service-based entrepreneurs build successful, six-figure businesses.
Crow and her husband co-founded a personal development company for entrepreneurs called The Daily Shift. “Scott and I both teach business strategy in our own companies, but we came together to help entrepreneurs grow and evolve themselves through our mindset programs,” she explains.
Crow found a life-changing partner in fellow entrepreneur Scott Oldford.
Image Credit: Libby Crow
She has also forayed into philanthropy. She recently made a substantial donation to Virgin Unite, a nonprofit that unites people and entrepreneurial ideas to create opportunities for a better world.
People often ask Crow how she keeps up with running her business and all of her other pursuits. “You need the right people in your life,” she answers. “You need the right friends and mentors, and you need to be dedicated to your own growth.”
Having a partner like Oldford has been life-changing, she says. “We have a thing where it’s not one plus one equals two. With us, one plus one equals infinity.”
“When you meet the right person, everything that you want to do becomes possible. With Scott by my side, I feel I can do anything,” explains Crow. “He sees me when I don’t see me. He believes in me when I don’t believe in myself.”
As she looks back on her journey, Crow has a few words for her younger self. “I would tell her that it’s okay to soften and to trust yourself. You don’t have to push and put pressure on yourself,” says Crow. “And any time you have an intuitive moment of deep knowing, follow that.”
One of Crow’s greatest achievements has been helping to support her mom.
Image Credit: Libby Crow
Reflecting on all that she has accomplished, Crow beams when she thinks of one achievement in particular. “My big dream was to be able to support my mom. I have helped her leave her job, move to California, and live right by the beach. Besides giving back philanthropically, that’s been my biggest success. I would do it all again 50 times just to be able to provide that for her.”
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