Young Caucasian male job seeker handing over resume to Latin American female human resources recruiter at workplace interview. Human resources, business recruitment and job interview concept
In 2015, Christopher Gray, founder of scholarship app Scholly, appeared on Shark Tank and secured a $40,000 investment for 15% equity from investors Lori Greiner and Daymond John. This made Gray one of the few to secure a share of the less than 0.5% of venture capital funding allocated to Black founders. Eight years later, and after spending more than $100 million promoting scholarships, Gray sold Scholly to Sallie Mae for an undisclosed but undoubtedly substantial price. They were likely the first brothers to get a free check from Sallie Mae with no repayments or debt.
After successfully navigating the education funding challenge with Scholly by Sallie, currently the top scholarship app, Gray shifted his focus to preparing young professionals to make the transition from college to career. Along with CEO Chandler Malone, also an innovative entrepreneur, he co-founded Path, an all-in-one AI-powered tool designed to streamline resume building, career coaching, test prep, and discovering personal passions.
The platform is already making progress: “We launched earlier this year with a lot of input and positive feedback from many of our users,” Gray told ESSENCE. “We’re currently working toward a potential agreement with the Department of Labor.”
If Gray has the King Midas chops for securing strategic capital and valuable partnerships, Malone’s superpower is fueling entrepreneurship and tech success. Prior to co-founding Path, he founded Bootup, which helped over 2,500 people land their first tech jobs and generated over $200 million in annual payroll at major companies including JP Morgan Chase. Additionally, his venture studio, The Family, has an estimated market cap of over $300 million and has deployed significant capital to Black and brown entrepreneurs.
After leading millions of dollars in scholarships, job placements, and salaries through their respective technology ventures, Gray and Malone have teamed up to ease the transition from college to career. I spoke with the founders about their latest ventures and the keys to their entrepreneurial success. Here’s what they had to say:
Chandler, as a startup funder and founder, what personal qualities or traits are most important to overcoming obstacles and achieving great success?
CM: Resilience and tenacity. When you look at people who have achieved something remarkable for others or for themselves, they all experienced periods of discouragement. Perhaps there were times when they didn’t have access to the resources or the allocation they needed. But they wouldn’t have been able to achieve anything for themselves or their families if they hadn’t found a way to persevere.
A lot of smart and talented people start startups, but their first idea rarely works. Ideas are essential for success, but what do you think is the difference between ventures that ultimately succeed and those that fail?
CM: I love this question. You can work for money, or you can work for a mission. Working for a mission makes it a lot easier to persevere through the hard times. When we think about the nature of the work we do, it has a lot to do with empowerment, creating opportunity, and putting other people in the best situations.
Chandler, that’s a really useful compass check for entrepreneurs. Christopher, everyone I know is very purpose-driven, is this commonality part of what drew you to partner with Chandler on Path?
CG: Totally right. When you really think about it, it’s all about relationships. Whether it was you and I meeting on a panel[at the Black Commerce Conference]or just knowing each other, Aisha[Bow, StemBoard founder]you want to work with people that you like and respect. It was the same with Chandler. We met at another company, about two years before Path.
This is actually an important point. I think you can see that a lack of relationships can sometimes be a barrier to accessing capital, especially in the black founder community. My advice to younger readers is to not get transactional with potential investors or co-founders. Even if they say no, maintain the relationships as much as you can. Even now, I would love to get to know some of the young people I met at the conference. I would love to spend time with them to understand what they’re doing.
That’s exactly what Chandler and I did organically through something completely different. So, I think it was a no-brainer, given the synergies, because we sold the company, we had a windfall, we were able to put the capital to work on another venture.
And the synergies are manifold. Chandler, can you explain what Path is, how it works, and how has your and Christopher’s combined knowledge, experience, and skills positioned you to bring the app to market?
CM: At a high level, Path leverages AI to streamline career development: our Career Coach provides personalized guidance using insights from thousands of conversations with career counselors, and our Resume Tool optimizes your chances of getting through our Applicant Tracking System.
What makes Path different is that it doesn’t rely on general best practices or broad tips. It tailors advice to the user’s needs. For example, say you’ve been laid off and are worried about your industry as a whole. With that prompt, Path can help you understand and identify transferable skills or determine what new skills you could add to land a position in a different industry.
The world is changing and evolving faster than ever before, so we need to be constantly learning and adapting. Skills Trainers create custom curriculum and assessments for the skills you want to master.
So, Path is like having a virtual personal career coach.
CM: Yes. And to answer the second part of your question, what was helpful about this collaboration was that I was able to leverage my experience at Scholly and Bootup to address challenges and opportunities in the field of career development. And we are both driven by the opportunity to support and uplift our communities.
Chandler Malone and Christopher Gray help young professionals navigate the complexities of today’s globally competitive job market. Their combined experience offers budding founders valuable insight and guidance on the value of networking, relationship building, and the power of mission and intention.
Some quotes have been lightly edited for clarity and brevity.
