In 2015, Christopher Gray, founder of the scholarship app Scholly, appeared on Shark Tank, securing a $40,000 investment for a 15% stake from investors Lori Greiner and Daymond John. The achievement made him one of few to secure a slice of the less than 0.5% of venture capital funding allocated to Black founders. Eight years and more than $100 million in facilitated scholarships later; Gray sold Scholly to Sallie Mae for an undisclosed but undoubtedly substantial price tag—perhaps the first brother ever to snag a check from Sallie Mae free and clear, with no payback or debt.
Having successfully tackled the challenge of educational funding with Scholly by Sallie—now the top scholarship app—Gray has shifted his focus to preparing young professionals transition from college to career. Alongside CEO Chandler Malone, an innovative entrepreneur in his own right, he co-founded Path, an AI-powered, all-in-one tool designed to streamline resume writing, career coaching, test prepping, and discovering personal passions.
The platform is already making headway. “We launched this year with a lot of views and positive feedback from users,” Gray told ESSENCE. “Now, we’re working on potential agreements with the Department of Labor.”
If Gray has a Midas touch for securing strategic funding and valuable partnerships, Malone’s superpower lies in fueling entrepreneurial ventures and driving tech job success. Before co-founding Path, he founded Bootup, helping over 2,500 people secure their first tech jobs, generating over $200 million in annualized salaries at major companies, including JP Morgan Chase. Additionally, his venture studio, The Family, with an estimated market cap of over $300 million, has poured substantially into Black and Brown entrepreneurs.
After directing millions in scholarships, job placements, and salaries through their respective tech ventures, Gray and Malone have joined forces to ease the college-to-career transition. I spoke with the founders about their latest venture and the keys to success on their entrepreneurial path. Here’s what they had to say:
Chandler, as a startup funder and founder, what personal qualities or characteristics are most important for overcoming obstacles and achieving significant success?
CM: Resiliency and relentlessness. You look at anyone who’s been able to accomplish anything worth note, for others or themselves, and they’ve faced a trough of discouragement. There’s been a period where maybe they didn’t have access to the resources or to the distribution they needed. But, none of those people ever were able to accomplish whatever that was for themselves or for their family if they weren’t able to find a way to persevere.
Many smart and capable people launch startups, but their first ideas rarely take off. While it’s often part of getting to success, what do you see as the differentiator between the ventures that ultimately thrive and those that flame out?
CM: I mean, I love this question. I think—you can work for money, or you can work for a mission, right? When you’re working for a mission, it makes persevering through difficult times a lot easier. And I mean, if you look at the nature of the work that we’re doing, it is very much about trying to empower, create opportunities, and put other people in the best situation.
That’s so helpful, Chandler, as a compass-check for entrepreneurs. Christopher, as someone I know to be very purpose-driven, was this commonality part of what attracted you to partner with Chandler on Path?
CG: Absolutely. When you think about it, it’s really all about relationships. Whether it’s you and I connecting on a panel [at the Black Commerce Conference] or having a mutual in Aisha [Bowe, StemBoard founder], you want to work with people you like and respect. It was the same with Chandler. We met through another company, maybe two years before Path.
This is actually an important point. I think we see, especially in the Black founder community, how a lack of relationships sometimes blocks access to capital. What I encourage young readers to do is: Don’t be transactional with potential investors or co-founders. Even if they tell you no [on funding], maintain those relationships as much as you can. Even now, with some of the kids I met at the conference, I want to get to know them; I like to spend time with people to understand what they have going on.
That’s exactly what Chandler and I did, organically, through a whole other thing. So, upon selling the company, having this windfall, and being able to deploy capital and work on another venture, I think it was a no-brainer with all the synergies.
And those synergies are diverse. Chandler, can you explain what Path is and how it works? Also, how has your combined knowledge, experience, and skills positioned you and Christopher to bring the app to market?
CM: At a high level, Path uses AI to streamline career development. The Career Coach leverages insights from thousands of conversations with career counselors to provide personalized guidance, while the resume tool optimizes your chances of passing applicant tracking systems.
What differentiates Path is that it doesn’t rely on generic best practices or broad tips. It tailors advice specifically for users’ needs. Say, for example, you’ve been laid off and are concerned about your industry as a whole. With that prompt, Path can help you understand and identify your transferable skills, or it can help you determine what new skills you can add to position you in another industry.
The world is changing and evolving faster than ever. So, we all have to be adaptable with a continuous learning mindset.The Skills Trainer creates custom curricula and assessments for any skill you want to develop.
So, truly, Path is like having a virtual, personal career coach.
CM: That’s right. And, to answer the second part of your question, what has been helpful about this collaboration is that we’ve been able to lean on our experiences with Scholly and Bootup to address the challenges and opportunities in the career development space. That, and we’re both driven by the chance to support and uplift our community.
Chandler Malone and Christopher Gray are empowering young professionals to conquer the complexities of today’s globally competitive job market. Their combined experiences offer invaluable insights and guidance to rising founders on the value of networking, building relationships, and the power of mission and intention.
Some quotes have been slightly edited for clarity and brevity.
