Attorney Asha Wilkerson on Building a Business and Leaving a Legacy

6 Minutes Read

Episode 60

Today Asha Wilkerson and I dive into building a business and leaving a legacy. Asha is an attorney by training and teacher by heart. She shares how after almost 10 years of running her law practice, she decided to shift her focus and build a membership community focusing on the needs of BIPOC entrepreneurs. 

She shares the book she probably shouldn’t have read early on in her career and the shift in the hustle mentality of entrepreneurs. 

Curious to know how the pandemic shifted her thinking as a business owner? Tune in to this episode. 

Here are three reasons why you should listen to the full Episode:

  1. Get insight into why Asha Wilkerson decided to shift her focus and build a membership community focus on the needs of BIPOC entrepreneurs.
  2. The shift in the hustle mentality of today’s entrepreneurs; why the traditional law practice didn’t work, the role of mentorship in her life, and that of her students.
  3. How the pandemic shifted her thinking as a business owner.

Episode Highlights

Asha Wilkerson’s thoughts on building a business that leaves a legacy 

    • People give themselves to the business but don’t understand how to craft the business to give back to the person. 
    • We start to have freedom and control of our destiny but don’t know how to make that happen. 
    • Do your passion. 
    • Make your passion work for you.  

Building a business and leaving a legacy

    • A sole proprietorship is an extension of the person of the individual.
    • Allow yourself to think about maybe one day you do want to sell your business.
    • Selling your business is a way to generate revenue and change the future.

Work in a way that gives you more freedom 

    • It’s training our minds to think about not being stuck at a desk.
    • Switch our mindset and start looking at our businesses like we would some other corporation or LLC.
    • It is your labor of love, but remove yourself from it. 
    • How would you evaluate this company? 
    • How would you run this company? 
    • What suggestions would you have for the owner if you were an employee? 
    • How would you implement those? 
    • Grow your business and build it in a life-giving way. 

Asha Wilkerson’s thoughts on BOPIC communities celebrating entrepreneurship

    • It’s psychological.
    • It comes from the history of the United States and being overdetermined. 
    • There’s a lot of freedom in entrepreneurship because you get to decide how you want to do it. 
    • There are not enough mentors or enough people in the BIPOC communities that have come before and shown how to run a business. 
    • Don’t just hustle for the sake of being busy; hustle smart. 

Did Asha Wilkerson always envision law school being part of her future?

    • She was not the kid that always wanted to be an attorney. 
    • Asha loved Law and Order but wanted to be like Dr. Wong, a forensic psychologist. 
    • The Dean of Admissions came into her Black Student Union and said they had opportunities for undergraduate students interested in law. 
    • The city cut the funding to the Boys and Girls Club in Portland, and that stopped her original plan to go home and work for the summer due to funding. So she applied to the summer law program.
    • Asha’s philosophy – Try and see what happens if the door opens. 
    • Law gave Asha the foundation to be able to help people in different ways. 

The biggest mistakes that entrepreneurs make could potentially destroy their business. 

    • Number one, not having enough information. 
    • You need to have people with the proper background placed around you to mentor you and give you information.
    • Build a team of attorneys, accountants, business coaches. 
    • If that’s too expensive in the beginning, join Facebook groups and communities to get the information. 
    • Make sure that your business is in alignment with what you want. 

Where did Asha Wilkerson’s mindset, passion, and focus originate? 

    • Asha’s mom and auntie are both career educators. 
    • She doesn’t need to be in control. 
    • There is enough for everyone.
    • She isn’t in competition with anybody. 
    • Don’t think about selling to somebody.
    • Think about the service that you are providing.
    • Know that your message comes through that. 
    • Coming from a place of service in your business will never steer your wrong. 

Change, Grow, Pivot

    • We see the wins on social media, but we don’t talk about the low points. 
    • It’s ok to pivot on your journey. 
    • Things have a season, and it doesn’t have to be the same way all the time. 
    • You can change, you can grow, you can pivot. 
    • Continue to innovate and change and offer something different or tweak it to fit what you want to do. 
    • Everyone is unique. Your company can be just as unique as you are. 
    • Don’t be afraid to pivot and make the change. 
    • Pivoting is not a sign of failure. 
    • Pivoting is a sign of growth. 
    • If you are not comfortable anymore with working the past two years, that is a sign of growth. 

How Asha Wilkerson gets mentorship and who speaks into her

    • She is part of the Rachael Rogers membership community.
    • She recommends being in a group of people from all stages but going in the same direction. 
    • If you are getting legal advice or tax advice, make sure that those giving the information are licensed professionals. 

How has the pandemic and social distancing affected Asha Wilkerson’s thinking as an entrepreneur?

    • She started thinking about how you can survive anything. 
    • People felt that you had to have a brick-and-mortar business. 
    • The pandemic made people think about how their business is running. 
    • Is the previous thought true? Is there another truth that you can latch on to now and grow? 
    • People are now taking the time to research because we have more time in our schedules. 
    • Follow your dreams, don’t wait. 
    • Figure out a way to do it.

How is Asha Wilkerson’s coaching community model setup? 

    • Transcend, her vision come to life. 
    • It is an online community resource for black and brown entrepreneurs.
    • Centering on the stories of black and brown entrepreneurs.
    • Her community is centered around the needs of our under-resourced community. 
    • A monthly membership with a theme each month is offered within her community.

How does Asha Wilkerson want to be remembered?

    • She wants people to say that something she said, or did, or showed them changed something for them.
    • She hopes to leave a positive impact that inspires change in people. 

3 Powerful Quotes from this Episode

The MindShift

00:01 - “So, for example, in my own life, starting my law practice, it wasn’t necessarily something I thought I wanted. I kind of started it out of necessity. I was working for a law firm, and they had layoffs, and I was one of the last people to get hired. So I was one of the first people to get let go in the layoffs. And I was taking contract work and applying for other jobs. And one of my friends said to me, she asked, you’re already doing the work. Why don’t you just open your practice? I was like, Why don’t…what…didn’t even cross my mind. I had no desire to be an entrepreneur to do my own thing, right. And then I realized that by going to law school, I had become the asset, right? I was the skill I didn’t need somebody else to empower me to do the work. So I started doing the work and started and opened up my practice.”


Hustle mentality

10:51 - “There is still some hustle to it; it just looks different. You do have to be the one to go and get the business. You do have to put in the work, there is still that hard work component to entrepreneurship, but it’s hustle smart. Don’t just hustle for the sake of being busy and saying you’re doing all of these things, hustle smart, so that your hustle becomes systematize. And you don’t have to keep you know, quote-unquote hustling anymore.”


Mindset Shift

27:05 - “There are models that are out there, but everybody is unique. And your company can be just as unique as you are. So don’t be afraid to pivot and to make the change. It’s not a sign of failure. It’s really a sign of growth that you have it, and maybe you did it only for a week, maybe you did it for two years. But that rubbed, that discomfort, don’t try and ignore it and feel like you’re failing, if you’re not comfortable anymore with what had been working for the past two years. That’s a sign of growth, and now you’re moving on to something else. And that’s ok. Getting to that point, I had to learn those lessons. I don’t want to just say it was a struggle, I went through the struggles, but the struggles taught me that it’s ok to pivot. That’s not a failure. That’s just a sign of growth. And that’s that mindset shift, right? “



Join the Transcend Membership Community 
Connect with Asha Wilkerson: Instagram | LinkedIn 

Books mentioned: 
4-Hour Work Week
Hustle Harder, Hustle Smarter 


About Asha Wilkerson

After almost 10 years of running her law practice, Asha Wilkerson decided to shift her focus and build a membership community focusing on centering the needs of BIPOC entrepreneurs. In the community, she calls in experts, and together they teach about proper business foundations (LLCs and corporations), how to take advantage of those resources, financial planning, tax planning, and retirement planning. They also discuss protecting yourself and your business through contracts, intellectual property tools, and what it takes to grow and scale within the community. 

In our community, it’s not uncommon for us to have to work until we die. I want to change that. Instead of working for your business, I want us to learn how to make the business work for us. 


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Thanks for listening,


Picture of Darrell Evans

Darrell Evans

Darrell Evans is a serial entrepreneur, investor, and Co-founder/CEO of Yokel Local Digital Marketing Agency. He and his teams have helped businesses generate over $300M+ in revenue online. Every month, he leads virtual workshops teaching actionable strategies and tips from his experience helping companies market, grow, and scale.