We recently connected with Lakeya Cherry and have shared our conversation below.

Hi Lakeya, thanks for joining us today. Day to day the world can seem like a tough place, but there’s also so much kindness in the world and we think talking about that kindness helps spread it and make the world a nicer, kinder place. Can you share a story of a time when someone did something really kind for you?

Earlier this year, I had an opportunity to attend TED Vancouver for the first time. While I’ve attended TED Women in past years, this was my first time attending TED and my first conference since the pandemic. I was excited because “Who doesn’t love TED talks?” but also admittedly fearful of not “fitting in” or being accepted into this community.

During TED, there are opportunities to meet fellow attendees during outings and dinner conversations. During one of the evenings, I attended a dinner focused on leadership. I was initially reluctant to attend after a long, stimulating day, but encountered one of the feature speakers, who introduced herself to me and my friend and encouraged us to not skip this dinner, but to show up, be ourselves, and have fun.

I took her advice and showed up. At my table, we did introductions and shared more about who we are, what we do, and our beliefs around leadership. I vividly recall taking a deep breath before sharing my story. I had made a conscious decision to show up as my authentic self and to speak from the heart about what mattered to me.

One of the attendees appreciated hearing my story and contacted me shortly after the event to convey their belief in me, and my business, and to extend a gift in support of its future.

This gift was so kind and extremely unexpected. It not only reminded me that there are people out there who do not know you but who believe in you and want you to succeed, but also it reminded me of the power of being true to yourself. I am forever grateful for this gift and reminded of the importance of authenticity and paying it forward.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am an executive leadership coach, CEO of Lakeya Cherry LLC, a coaching and consulting business, and Partner at Evolution, Silicon Valley’s premier coaching, consulting, and investment firm for start-ups & high-growth companies to drive long-term, holistic success. I previously served a 9-year term as the CEO of an international nonprofit organization.

The first few years as a CEO were daunting. I experienced a lot of self-doubt and insecurities about whether I was the right person for this role. I was challenged to further develop myself as a leader and to have better boundaries. Externally, I was making moves, but internally, I was in scrambles. During this time, I learned about a coaching program for women leaders in the social impact space and applied. Once accepted, I had the opportunity to work with an executive coach for 11 months and had a transformative experience. I realized that I wanted to become a coach someday and support other emerging and seasoned leaders. This goal was put on hold for many years, but after completing my doctoral program in 2020, I realized it was time.

In my business and as a Partner of Evolution, I serve as a coach, trainer/facilitator, speaker, and consultant/advisor. My services include individual and group coaching, bespoke workshops, and offsites. In addition, I also offer Google #IamRemarkable and customized Brené Brown Dare to Lead™, courage-building workshops.

My mission is to build the internal capacity of leaders through daring leadership, clear visioning, and unwavering intentionality. What this means is that I am committed to helping leaders to become more emotionally intelligent and to do inner work to address the roadblocks and barriers that prevent them from being the leaders they envision. I help them to determine where they need to be more courageous and carve out a vision and path for taking action. In addition, I support organizations by leading processes for them to do the same self-reflective action-oriented work of creating inclusive, courageous cultures where all people belong and are committed to the mission and vision of the organization.

I am really proud to be living in alignment with my two core values of growth and contribution. For years, I operated with a scarcity mindset and was fearful of taking risks. I am now challenging myself to go after what I want and embracing my fear. I want potential clients to know I am passionate about this work and will meet each of them where they are while also holding them accountable for progress.

Any insights you can share with us about how you built up your social media presence?

Branding is an important part of building a business that many people overlook. When I first became the CEO of the nonprofit organization I led, I realized that while this organization had existed for over 25+years, it had a very small audience. The website was outdated and it did not have a social media presence. I do not have a formal marketing background but knew social media was an avenue to build our brand and influence. We signed up for traditional social media accounts i.e. Facebook, Twitter, Linkedin, and Instagram, and began posting regularly. The more we posted, the more engagement we received. After a few months, our number of followers increased and continued to increase with every post, hashtag, photo, event offering, testimonial, etc.

For my own business, I’ve employed many of the same tactics to grow my own personal brand. My LLC has its own social media handles and I also try my best to post a few times a week on my personal LinkedIn account. I share personal stories, articles, and content such as quotes that resonate with my brand. In addition, I share testimonials, blog postings, podcast episodes, and other external media features.

It’s not always comfortable to promote myself or my business and its services all of the time, but I realize this is necessary for its growth.

For those just starting out, remember that word of mouth only takes you so far, marketing and building a social media presence can aid you with lead generation and conversion. People want to get to know you and your business. They want to see what you’re about and social media allows you to do this. Go at a slow and steady pace to build your comfort in this area. Also, a reminder that if this isn’t a strength, it may be worthwhile to consider investing in someone who can help handle these aspects of your business.

Can you talk to us about how your side-hustle turned into something more.

When I first started my business, I never would have imagined that I would someday be doing this line of work full-time. I started my business during the pandemic as a means to upskill while also generating additional income. I wanted to have a plan B just in case anything happened with my full-time career. I also had just completed my doctoral program and wanted to begin applying my skills in new ways with new audiences. I first decided to register for an LLC after being sought out by an association to design and facilitate their board retreat and another association to be a guest speaker. These requests were outside my CEO function, but opportunities I was interested in. I consulted with members of my personal board of advisors and they encouraged me to start an LLC and to slowly start taking on these types of opportunities as I had time. I listened to their advice and started the LLC and started using the brand I already had to promote a few different product offerings. My audience was receptive and began purchasing my services. I then used the money I made to cover the costs of a coaching program and a few certification programs. Once I completed my coaching program, I began offering discounted coaching sessions in order to obtain clients and build my brand as a coach. I used this money to pay for branding photos and a website. As you can see, each step was incremental. I made money and then reinvested it to grow the business further. The more visibility I/my brand got, the more my business began to grow. I also was fortunate to be invited to become a Partner of a firm, which provided additional opportunities and sources of income. After my first year of business, I realized that I was just a few thousand dollars shy of my nonprofit salary and this was from working just a few hours per week including after hours, weekends and that I loved the work I was doing and growing as a person, leader, and coach/consultant significantly. After my first year in business, opportunities continued to come my way, but I had to turn many down because I was still in a full-time CEO role, which took significant time. I realized that the work I was now doing as a side hustle gave me more energy and that if fear wasn’t an obstacle and I had to choose, I’d choose entrepreneurship and my business. I just completed my second year of business and officially left my last role on June 30th of this year. My business is growing, I am growing, and I am happy I trusted myself to take this leap. Full-time entrepreneurship is not “easy,” and can be scary, but for now, I am enjoying the ride.

Contact Info:

• Website: https://lakeyacherry.com/
• Instagram: https://www.instagram.com/lakeyacherry/
• Facebook: https://www.facebook.com/lakeyacherryllc
• Linkedin: https://www.linkedin.com/company/lakeya-cherry-llc
• Twitter: https://twitter.com/lakeya_cherry

Image Credits
Photography: DFinney Photo