Stella Ashaolu, founder & CEO of WeSolv speaks with Activate cohort

Event Recaps
Nov 30, 2021

On November 5, 2021 the participants in the Activate program virtually welcomed Stella Ashaolu, founder & CEO of WeSolv and co-founder and investor of Fifth Star Funds to the cohort's weekly meeting for an inspirational talk and Q&A.

Ashaolu started by sharing her story with us. A proud Bruin (a.k.a. University of California, Los Angeles), her early work as a business and strategy manager made Stella Ashaolu realize she was more interested in business than in law. Further, her experience as a consultant with Fortune 500 companies and their selection strategies as well as some personal experience allowed Stella to recognize the unrealistic expectations and strained power imbalances across the board. This led to the creation of WeSolv. By leveraging performance data and transferable skills, WeSolv has been able to promote a more diverse group of candidates to top companies. But her company didn’t spring up overnight.

Ashaolu went on to illustrate how she built her business by learning while doing. Networking not only with peers, but through entrepreneurial organizations helped her to gain support, and create an early MVP (minimum viable product) to test with clients, which helped her earn her legitimacy.

There is value in creating relationships throughout your journey, and having dignity at the same time as humility. She adapted a well known phrase with her advice to the cohort members in saying: “Closed mouths don’t get fed, but I will not beg.” Ashaolu explained that entrepreneurs should not be ashamed of admitting or asking for help, but to work with people who believe in you and your project. Stella used meet up groups and cohorts to build relationships that helped her climb to the top, and further advocated for putting together an MVP even if all you have is “duct tape, shoe string, and bubblegum.”

“Real performance is the most indicative of being hired by a company, and also indicative of future success.”

She stressed the importance of listening to your customer, and building off of your MVP. Stella knew first hand that there were improvements to be made in the hiring process, but she wasn’t the person who needed to be convinced. One of the keys to assessing value for potential clients was creating “value lanes” within the WeSolv pricing model to find out where their customers were most interested. 

“I learned really quickly you can’t be the source of your customer discovery.”

In the summer of 2020, Stella Ashaolu and her team took what they learned and started creating Fifth Star Funds, a venture capital fund that acts as the “friends and family” funding round for Black founders in Chicago. From their LinkedIn page: 

“The Chicago flag features four stars that represent pivotal events in our city’s history; we contend that the Fifth Star belongs to underrepresented founders and the extraordinary impact they will have on our city’s future.”

Ashaolu’s talk made it clear that the people involved in your business are vital to its success. It’s crucial to listen to your clients and customers, create a strong and positive network of people who believe in you and what you’re doing, and build a team of people who share your vision for the culture of the company. In the end, the hardest part of transitioning from “learning to doing” was learning what not to do and learning the narrative so you can understand how to change it.

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