How Hope Macgregor鈥檚 Entrepreneurial Journey Took Flight Through Music
never imagined her path would transition from flying helicopters over Afghanistan to standing on stage, guitar in hand. But if there鈥檚 one constant in her life, it鈥檚 embracing the pivot, and doing so with purpose.
Hope explored a wide range of career paths. From college to law to military service, the journey from Army pilot to singer-songwriter was far from what she expected. Now, a part of the taught by , she is obtaining the needed soft and hard skills to grow her music career.

A Rediscovered Passion
In what she describes as a 鈥渞ebellious decision,鈥 Hope veered away from the typical route many teenagers take. Though she initially planned to attend Oklahoma State, she ultimately found herself at West Point, stepping into military service that would further develop her resilience and sense of purpose.
Her time in the military was transformative, but after completing her active duty service obligation, Hope was ready for a change.
While transitioning out of service into law school, Hope faced a series of personal challenges. Her father came to offer support, and stumbled upon one of her old guitars, which she hadn鈥檛 touched in years. This unexpected discovery reignited a long-suppressed passion, ultimately sparking the beginning of her music career.
Learning to Lead Her Art
Hope's business formally began when she established her LLC. The emotional and creative foundation was already there, but this was the moment where she formally began treating it like a business.
played an important role in helping her transition her passion to a successful business. Though she had already formed an LLC for her music, she admitted feeling overwhelmed by the practical demands of entrepreneurship: like filing taxes and navigating business law. With a background in military aviation and limited exposure to the world of business, she turned to the program after a Google search for Veteran resources. The program, designed specifically for Veterans, offered her a structured environment to gain foundational knowledge in areas like finance, taxes, and marketing.
Beyond the technical skills, the Veteran Entrepreneurship Program gave her a sense of community and validation. She initially walked into the program feeling intimidated, but she quickly found support and encouragement from both peers and instructors. The experience helped her realize that she wasn鈥檛 alone in her learning curve and that entrepreneurship could look different for everyone. It gave her the tools and confidence to pursue her music career seriously while honoring her values and personal style, reinforcing her identity as both a Veteran and an artist.
A Voice with Values
For Hope, music isn鈥檛 just a career, it鈥檚 how she communicates with the universe. 鈥淪ongwriting is how I pray,鈥 she shares. Her sound, a blend of blues, country, and classic rock, falls under the broad umbrella of Americana. Genre is secondary to her mission of emotional honesty. Every song she writes comes from a real, raw place, each word with an honest meaning.听

听Hope resists the industry鈥檚 pressure to conform, especially for female artists. She refuses to dress or perform in a way that doesn鈥檛 align with her values, and that resistance itself
听has become part of her voice. She admits that she likes the rebellion of it, describing how her songs speak to people who don鈥檛 see themselves in mainstream music.
Like any artist, Hope has dreamed of stadium tours. But for now, she gravitates toward intimate venues where she can connect with audiences face-to-face. Music is powerful to her when she shares a 鈥渞eal truth鈥. This has fueled a debut album in October of 2023 and a major tour slated for July.
Building a Business with Heart
Though she's found her calling, Hope is quick to point out the realities of the music world. Although there are days where she wonders if entrepreneurship is harder than the Army, she remains grounded, balancing her art with a flexible day job to fund her career. Her entrepreneurial spirit drives her to forge a sustainable, self-directed life.

What truly distinguishes her as an entrepreneur is her desire to live on her own terms. For her, entrepreneurship is not defined by full-time self-employment or profit margins; it鈥檚 about designing a life that enables passion-driven work, even if it means taking an unconventional route to get there.
Hope鈥檚 career isn鈥檛 defined by profits or business plans. It鈥檚听
fueled by passion and determination.听
鈥淏eing an entrepreneur, for me, is setting my life up in a way that I can do what I want to do when I want to do it.鈥
That clarity of purpose has guided her through career pivots, personal challenges, and the leap into music. Her journey reflects a broader truth: entrepreneurship is deeply personal. It鈥檚 more than just about building something new.
Hope鈥檚 journey reminds us that entrepreneurship isn鈥檛 limited, it鈥檚 also about building a life filled with meaning, authenticity, and courage. Once in the cockpit, and now on stage, Hope is writing her own authentic story.
Photography by: 1, 2: Nicole Gray. 3: Hannah Gore 听