Georgetown Alumnus Launches Coaching Startup With Georgetown Startup Accelerator

Tony Lin (C’14) co-founded Skye, an innovative platform that matches entrepreneurs and executives with personalized and experienced mentors who offer specialized coaching services that aim to guide a professional’s career and unique leadership journey. 

Lin, along with the startup’s co-founders, Jessica Wolf, and Gabriel Chen, launched Skye with the help of the Georgetown Startup Accelerator (GSA), an initiative led by Georgetown Entrepreneurship that helps alumni entrepreneurs gain access to more experienced mentors, peers, and leading subject matter experts to help manage their early-stage startup ventures. 

The accelerator includes opportunities for alumni entrepreneurs to work with mentors one-on-one, attend weekly workshops led by expert guest speakers, and be in the company of like-minded professionals. Participant entrepreneurs receive guidance on areas such as benchmarking and goal setting, team management, sales and marketing, fundraising and investing, and finding product fit. Through GSA, the founders met Slade Smith (B’26), one of their angel investors.

The idea for Skye came together when Lin’s co-founder, Wolf, was attending a graduate degree program at Columbia University. It was during that time that she saw a need for a support system. “Therapy wasn’t quite the answer for me because I had some career considerations. And so, a coach felt right,” Wolf said. 

However, the journey of finding a coach tailored to her needs was difficult. Wolf said she struggled to find a coach who was “a good fit from a chemistry standpoint, pricing standpoint, and a quality fit.” That was when she saw the need for a “platform of scale” that could help entrepreneurs and young professionals find coaching experiences tailored to their needs. 

Seeking to create such a platform, Wolf approached Lin and Chen. The idea attracted Lin because it aligned with his personal values, as well as those of his alma mater, Georgetown University: women and men for others, or care for the whole person — cura personalis. 

Having benefited from mentors and coaches himself, Lin said the ability to help people find coaching and personal development opportunities is a way he can live up to the value of “women and men for others.” As one progresses in their career and entrepreneurship journey, he explained, they feel “less and less relatable” to the people around them. That is where the Skye coach plays an important role, according to Lin, becoming one’s confidant, thought partner, and someone they trust and work with on their own challenges. The coach also acts as an accountability partner.

The agenda of the coaching sessions, according to Lin, is driven by “what an individual wants to improve upon” with the coach playing a supporting role. “So it’s not the coach delivering something, the agenda is your agenda,” Lin said, adding that when he was coached himself, he was mentored by an experienced entrepreneur. 

“I asked the coach a lot of entrepreneurship questions that I wasn’t sure about,” Lin said. “Questions I did not want to ask publicly in an open forum but was comfortable enough to ask the mentor like, how do you do this? How should I think about this?” he said.

Coaching with Skye is a “safe space” for young professionals as entrepreneurs,” Lin explained.

The process to sign up is “simple and really approachable,” Wolf said. “You come to the platform, create a profile, which is done through a series of questions. From there, in about two minutes, you are paired with two coaches that we think are a good fit for you or you can immediately schedule a call with our team.” Alternatively, prospective clients can opt for a “slow approach” in matching with clients.

According to Wolf, Skye’s matching algorithm, written by Lin, uses data on a client’s “values, professional background, goals, and aspirations” gathered from the questionnaire to match clients with coaches. To supplement the algorithm, a team member from Skye also communicates via a phone call with the client to capture nuances uncaptured by the algorithm. The nuances can include “What’s happening in your work and life right now? What’s your biggest stressor? What keeps you up at night?” she said. After the matching process is complete, Skye provides clients with two coaching matches.

“We’re really trying to help people lead happier and more fulfilled lives, and we’re starting on that journey at a one-to-one scale, which we think is pretty powerful,” Wolf said. Long term, the startup plans to expand into “group coaching” and enable former clients to get coaching accreditation once they graduate from the program so that they can come “back into the platform and join our community” and become coaches themselves, she explained.

For Lin, he believes his experience as a Georgetown student and first-year residential assistant (RA) inspired him and has continued to guide him through the early days of Skye. Lin’s time as an RA taught him skills related to “working with people and building proto-communities and helping students become integrated into the Georgetown community — similar to the idea of coaching or mentorship — like Skye provides.”

“Something that really drives through the Georgetown community is an undertone of ‘how can we create solutions that help everyone?’ Lin said.