Harmony N. Oswald, Esq.: Redefining Fintech, Legal Tech, and Edtech with Vision and Grit
Harmony N. Oswald, Esq., a U.S. Army Veteran and Silicon Valley tech innovator, is the Founder and CEO of lucy technologies, inc., home to Legalucy—the #1 pre-lawyer legal platform wordwide, empowering business owners to navigate legal challenges, using AI, before going to a a lawyer. With a Juris Doctor degree from Santa Clara Law, a High Tech Law Certificate with Honors, and over two decades of experience in media and communications, Harmony blends her expertise to drive global innovation. Her leadership and commitment to closing gender gaps in tech and venture capital have earned her recognition from Silicon Valley Business Journal, Stella Women’s Venture Summit, The LegalTech Fund, , Santa Clara Magazine, Equipment Leasing & Finance Magazine, and Entrepreneur Media.
A fearless strategist and lifelong learner, Harmony has served on the ELFA Innovation Advisory Council (2023–2025) and contributes to Entrepreneur Magazine. She’s a sought-after speaker on AI, fintech, and legal tech innovation, a mentor to law and business students, and a champion for empowering women in tech. Beyond her professional accomplishments, Harmony is a dedicated wife and mother who advocates for fostering inclusive leadership and innovation.
How did your journey as a U.S. Army Veteran shape your career path in finance law and lead you to Silicon Valley?
I grew up in a small town in Western Pennsylvania, USA, where limiting gender roles dictated that I could be, for example, a cheerleader, beauty pageant queen, or caregiver. As a teen, I lived with my grandmother in an economically disadvantaged situation. I got married by the age of 20.
To prove my strength and resolve, I enlisted in the U.S. Army. As a soldier, I learned to fight like a girl by strategically digging fighting positions, shooting machine guns and qualifying as a Sharpshooter, and persevering with fortitude to win battles. In basic training, I was selected as the ongoing platoon leader, and I was presented with a Superior Performance Award outperforming all men for the honor. I then served active duty in Würzburg, Germany, where I received a gold coin of excellence from General Wesley Clark for international service as a soldier and a broadcast journalist (46R) in the First Infantry Division.
By the young age of 24, I became a divorced single mother of two children.
Recognizing the need and opportunity to advance young women, I pitched my idea for a show to MTV in Times Square, Manhattan, NYC. Details of how I was encouraged to act like a “sex icon” on camera were highlighted in Wendy Ryan’s award-winning leadership book, “Learn, Lead, Lift.”
To further establish my reputation as a breakthrough leader, I applied for and was selected as a contestant on NBC’s “Fear Factor” – the hit television show with Joe Rogan, and Rogan expressed concern on-air that I might steal his job.
Because my birthday is on the same day as Abraham Lincoln’s, I was inspired from a young age to become a lawyer and pursue “justice for all.” Growing up in a small, rural town, however, there was no path for me.
Overseas military service changed the trajectory of my life, providing me with a broad worldview, leadership skills, and the confidence needed to become anything I want to become. Desiring to live in the land of “milk and honey,” where economic opportunities are plentiful, I moved to Silicon Valley when my kids were teenagers, and I went through law school there. I won a writing award at Santa Clara Law’s Entrepreneurs’ Law Clinic, completed a coveted Google internship, earned a high-tech law certificate with honors and a high-tech excellence award, and was the recipient of a Witkin award for my research and writing on Gender and the Law matters. I earned my Juris Doctor degree and secured my CA Bar license. I was ready to help close gender gaps in tech, leadership, and venture capital funding for women-led businesses in Silicon Valley and beyond. I forged a strong partnership with the Silicon Valley Founder Institute, where we put on startup pitch competitions in San Jose, CA, and as a result, I was offered a fellowship by Vet Tech to build a billion-dollar tech company. Out of that research and testing at the Silicon Valley Founder Institute, Legalucy (lucy technologies, inc.) was born. My team created a new category in legal, and it is now the #1 pre-lawyer legal platform in the world.
What inspired you to create Legalucy, and how did you identify the need to help business owners address legal issues through AI before approaching a lawyer?
A mentor of mine, Eddie Hartman, co-founder of Legalzoom, once shared that smart entrepreneurs consistently come from a position of “knowing nothing.” Continuously testing, learning, and iterating has been Legalucy’s fundamental strategy along our path toward dominating the global fintech market by creating the leading AI product serving business owners worldwide.
Growing up in a family of entrepreneurs provided me with valuable insights into the tensions that arise between business owners and lawyers. Business owners tend to avoid lawyers to their detriment. They don’t trust lawyers to share the minimum amount of work that is needed, and they don’t want to pay high legal fees. Further, they don’t understand the value a lawyer will bring to their business. Outdated models try to match business owners with an attorney from the start, but they don’t want to be matched. Instead, business owners randomly research based on limited knowledge and ask friends for advice. In America alone, business owners throw away $160 Billion per year of hard-earned cash by making mistakes and litigating.
Access to justice issues runs rampant and this problem creates significant opportunities for an innovator who actually listens to the complaints of small business owners and then takes action to disrupt the status quo by taking a backward approach – creating an end goal and exit strategy from day one, putting into place the milestones necessary to solve the issue and scale, and then implementing the team and partnerships to test, iterate, and execute the vision. Taking a backward approach to innovation while constantly testing, learning, and iterating to execute and scale is how we win at Legalucy.
In addition, as a Silicon Valley tech founder and CEO, I believe that competent women-led companies deserve equal access to Venture Capital funding. My vision is to be a competent, independent, successful tech leader, raise Venture Capital, take Legalucy to market, and then share with other women-led companies how to get it done. That’s exactly what I do each day… Be the change!
Legalucy merges technology and legal expertise. How did you navigate the challenges of integrating AI into the traditionally complex legal industry?
“Once Everest was determined to be the highest summit on earth, it was only a matter of time before people decided that Everest needed to be climbed.” -Jon Krakauer
I envision living in a vibrant, beautiful world built by ALL people. To make this vision a reality, more women must become leaders, tech innovators, and venture capitalists. I am on a mission to scale the mountain. As a U.S. Army veteran, a former NBC Fear Factor contestant, a commercial finance litigator, and a Silicon Valley tech founder and CEO, I am uniquely poised to be the change. At Legalucy, we leverage grit and tenacity to push forward, approaching every challenge as an opportunity to reach new heights on the path toward becoming the global leader in AI for businesses.
Legalucy was selected as a top early-stage Gen AI company by The Legaltech Fund in 2024. What factors do you believe contributed to this recognition, and how has it impacted your company’s growth?
Legalucy is a first mover and category creator in legal with our interactive pre-lawyer assistant, which is the #1 pre-lawyer legal platform worldwide. We are “all in” rebels and pioneers ahead of our time with our proprietary DSLM. We’re positioned for rapid, exponential growth greatly exceeding the 1% global fintech market share within seven years that’s laid out within our financial projections. At year three, we will expand into, for example, tax, HR, and lending.
How does Legalucy empower small business owners to identify and solve legal challenges more effectively, and what sets your platform apart from traditional legal services?
Lawyer Joke:
“How many lawyer jokes are there? Only three. The rest are true stories!”
This is just one of the countless examples of lawyer jokes, showcasing the disdain and mistrust people have for attorneys. Much truth is often spoken in jest, yet, somehow, no one has ever taken the problem seriously. As a result, business owners throw away over $160 Billion each year – in the U.S. alone – avoiding lawyers, making mistakes, and litigating. Insanity is doing the same thing over and over and expecting different results!
Legalucy is the number one pre-lawyer legal platform on the market. We help business owners narrow down issues, using AI, before engaging a lawyer. They receive step-by-step guidance to solve the issue fast, gain access to forms, and gain insights about how a lawyer can help. They can hire lawyers right on the platform. Our AI-powered interactive pre-lawyer assistant learns and makes increasingly customized recommendations across time to build trust, so they won’t want to go elsewhere. Plus, our compliance dashboard upgrades will provide proactive legal alerts and reminders, keeping businesses safe and secure.
Outdated models focus on lawyer matching. However, people don’t WANT to be matched with a lawyer. Plus, they assume people KNOW what help they need, but business owners are confused. Our proprietary DSLM and culture-powered AI provides businesses with on-demand solutions, and like Canva which is valued at over $40 Billion in 2025, our platform is sticky, attracts users, and encourages upgrades. Plus, we send over high-quality, vetted leads to the firm, to eliminate inefficient consultations and provide lucrative business opportunities to lawyers.
How do you see AI transforming the legal landscape in the next 5–10 years, and how is Legalucy preparing to stay ahead of these changes?
Legalucy (lucy technologies, inc.) is a first mover and category creator in legal with our proprietary DSLM and culture-powered AI. Our CTO, Michele Ellie Ahi, is a Silicon Valley Tech Guru – a leader with decades of experience in global tech development. The team at Legalucy works diligently to ensure access to justice for ALL people, while also helping legal professionals focus on billable tasks and eliminate inefficient consultations.
In year three, with our industry-agnostic technology, LUCY will expand into tax, HR, and lending. Legalucy is currently the #1 pre-lawyer legal platform on the market, and LUCY will become the most adopted AI platform worldwide for business owners.
As a finance attorney and tech entrepreneur, how do you balance maintaining legal excellence while driving innovation in AI and legal tech?
Based in Silicon Valley, California, USA, a region often lovingly highlighted as the “land of milk and honey,” LUCY is strongly positioned to stay ahead of the curve as a first mover, category creator, and market leader in fintech and legal tech, by gaining access to excellent Silicon Valley educational experiences, cutting edge business opportunities, advanced AI and tech resources, teammates, and partnerships that companies and founders in other areas of the world could only dream of. We are grateful!
In addition, the Mediterranean climate and mountainous, coastal terrain in the Bay Area of California provide founders, team members, and partners with a diverse range of self-care opportunities, such as hiking, to enhance the ability to clear the mind, reflect, meet with partners, and innovate. For example, Legalucy recently partnered with brilliant mentor, John Majeski, General Partner at the Silicon Valley Women Founders Fund, to establish a “Tech Hikers Club,” to provide opportunities for entrepreneurs from around the world to meet with tech-focused investors while experiencing an immersive hiking adventure. In the land of milk and honey, we are blessed and lucky! $$$$$$$
What were some of the biggest challenges you faced while building Legalucy, and what milestones are you most proud of?
At Legalucy, our biggest challenge has become our biggest opportunity to expand. To clarify, because women were historically prevented under the law from controlling their finances and building wealth, society is now in a position globally where rebels, underdogs, and allies in business are being challenged to build a brand new ecosystem in entrepreneurship and investing that works well for ALL. Challenge accepted!
The outdated Silicon Valley and beyond Venture Capital ecosystem inspired me to become a technology investor and fund Legalucy on my own. Going “all in” as an investor is the single best entrepreneurial decision I have made that I am most proud of. I became a CA commercial finance litigator at my own firm so that I could personally bootstrap Legalucy to hit significant milestones with limited external resources. Following a coveted internship at Google during law school, I was in a uniquely strong position where I could have easily pursued a career as a big firm lawyer and banked cash like many of my peers. I come from a family of entrepreneurs, however, and viewing the world through this innovative lens, and with testing and experience, I recognized the HUGE problems small business owners were facing in legal and the much bigger opportunity presented to solve these issues, by leveraging Legalucy’s proprietary DSLM to ensure access to justice for ALL at a global scale. Rather than pursuing the typical attorney path, I took big risks and made bold moves as a Silicon Valley AI and tech entrepreneur and investor to build Legalucy (lucy technologies, inc.).
Our team has hit amazing milestones! Our premier product, Legalucy, has helped over 4,200 business owners. We completed a paid pilot program, proving our financial hypothesis. We were featured on the cover of the Silicon Valley Business Journal Book of Lists and were highlighted by The LegalTech Fund as a top early-stage Gen-AI company. We were showcased at Stella’s Women’s Venture Summit by the keynote on stage. I recently advised U.S. President Donald Trump and Elon Musk regarding Legalucy’s vision to change the way legal gets done. We accepted our first VC funding commitment from a well-vetted, good-fit partner. I was invited to be an ongoing contributor at Entrepreneur Magazine (with an audience of 20 Million unique monthly visitors and 15 Million social media followers).
What are the most valuable lessons you’ve learned as an entrepreneur, and how have they shaped your leadership style?
Most Valuable Lessons I’ve Learned:
Follow the money. Become an investor. Make bold moves. Research potential partners, carefully select meetings, and say no to those who are not a good fit. Persevere. Persevere. Persevere. And always remember to have FUN!
