Second-Generation Entrepreneur Shares 4 Lessons on Impact of Entrepreneurship at Home



“If you know how to sell, you won’t be broke a day in your life.” My dad, Keith Williams, the Senior Pastor of Cornerstone Christian Fellowship and serial entrepreneur, has told me this since before I could legally hold down a job.

For most of my life, my father exposed me to entrepreneurship, business leadership, and relying on myself for a paycheck. I couldn’t be more thankful for the environment he and my mom, Valerie Williams, created – an environment of support that I hope to pass down to my daughter, too.

Seeing my father build a seven-figure business taught me that I could do that and more. His example as an entrepreneur is crucial to my journey as one today. Many studies suggest that less than 3% of women-owned businesses hit seven figures in annual revenue and little data was found on what percentage of Black woman owned companies achieve this milestone. There is zero doubt in my mind that growing up seeing my parents own a company helped me beat the odds, not by just teaching me business strategies, but by showing me how to dream – a gift my husband and I want to give to our daughter. As I think back on what helped me grow my own seven-figure company, I often recall the wisdom I learned in my home growing up – and the lessons my parents continue to teach me today.

Here are five powerful lessons I learned by growing up in a home where entrepreneurship is encouraged!

Lesson 1: Don’t be afraid to work in front of your kids — ditch the guilt and instead explain to them why you’re working and what you do

If you knew my dad growing up, you knew he had a car phone. He loved that thing. It’s not as impressive now, but when I was growing up? A car phone meant that you were all business. And my dad used that car phone, too. I remember my dad was always taking calls and often worked long hours. He managed to still show up to our events at school, but it was in between long hours at the office. My dad’s office was great. I remained fascinated by the stacks of paper on his desk and the fact he had a receptionist. At the time, I thought those stacks were just as cool as stacks of dollar bills.

My mom worked just as hard, too. And through that example, I learned how to work hard. I learned that if I could sell, I could hold a job and support my family. I learned I didn’t have to rely on anyone but myself for a paycheck, and that a paycheck could be used to positively support the community around me.

Here’s the key; I actively remember my parents explaining that they worked to pay bills and ensure we had money to travel, tithe, and employ people. They never made me feel bad for needing to provide but did explain that by allowing them to work, I was contributing to the family too. My daughter is only two years old, but has a similar exposure to entrepreneurship. My husband and I teach her the value of hard work.

Dear parents, stop letting people make you feel guilty for working. Let them kids see you work – and instead of feeling bad, explain to them that by giving you some space to work, they are helping the family too! I know, I know,  “let them kids see you work” isn’t proper grammar, but it needed to be said! As a toddler mom and wife it’s easy to feel bad for working, but remembering how I was taught that work is contribution helps me to ditch the guilt – at least on some days!

Lesson 2: Losing is necessary and you need to learn how to lose as much as you need to learn how to win — it builds character

The constant rejection and perseverance that comes with running a business can turn aspiring entrepreneurs away from entrepreneurship. But before I started my company, Speak Your Way To Cash, I took a sales job. In that job, I kept my dad’s advice in the back of my mind: “Sometimes losing keeps you humble.You can’t win everything every single time.” He would often go on to tell me, “this may not be the right person to give you a ‘yes,’ but that person is out there – don’t let anyone give you the no that stops you.” My dad may not have been directly talking about entrepreneurship, but this wisdom guided me as I navigated my early days as an entrepreneur. I feel like a big lesson I learned from my parents was how to lose without giving up. Resilience is critical – especially when instant gratification seems to be what what everyone wants nowadays.

Lesson 3: Never make your kids the scapegoats for your dreams — show them what’s possible by going after your own dreams with resilience

When my parents  told me to follow my dreams, I believed them, because they were the manifestation of that advice. I saw my mom go back to school to finish first her undergraduate degree, then her M.B.A. I saw her start at her company as a secretary and then become a senior project manager at one of the largest insurance companies in the world. I saw her follow her dreams. And seeing that first-hand deeply impacted me as a business woman and an entrepreneur. After graduating from college, I worked in sales, then I applied to law school and got rejected from every law school that I applied to, but I didn’t give up. I reapplied the following year because I saw my mom go back to school. Eventually, I not only got into law school, but graduated with honors from Northwestern University Pritzker School of Law. Upon graduation, I worked as a federal trial lawyer at a top law firm in Chicago – again, only after they rejected me the first time I applied. These were corporate experiences but all of them played a huge role in building the resilience I rely on today as an entrepreneur.

In my work as a business coach and professional speaker, I encounter a lot of parents who step away from entrepreneurship because of their children. My parents taught me to do the opposite. They pursued their dreams in front of us – me and my brother, Wilbert Williams, who owns an athletic apparel brand, Suburban Knight Clothing. We  saw how happy our parents were when they pursued their purpose, so I’m determined to do the same. When my daughter starts to forge her career path and make decisions about the life she wants to live, I can only hope that she will reflect on her experiences growing up in the same way I reflect on mine.

To my fellow entrepreneurs, we can prove to our kids that it’s possible to achieve our dreams by achieving our own.

Lesson 4: Generational wealth is about more than money

My daughter is only two years old, but I want her to have the same exposure to entrepreneurship that I had. Why? Because generational wealth is about more than the money and resources you leave when you’re gone. It’s also about the wisdom and insight you can provide while you’re here. And, if people can pass down generational curses, they can surely pass down generational blessings, wisdom and peace.

But how do you pass this down? Here’s three tips.

You’ve got to build skills

My clients are in their 30s, 40s, 50s, and 60s putting in the work to develop skills that they can directly apply to their businesses. If you want to see the fruit of your labor in your lifetime and generations to come, it’s time to build a foundation of skills now. I promise you there is so much value in your kids seeing you learn and then eventually master a new skill – it builds immeasurable confidence. Find out where you are deficient. Gather materials that can help you fill in those gaps.

Build great relationships

When you surround yourself with people who support you, you will go farther. This is the beauty of being raised by parents who support entrepreneurship. When I decided to pursue it, their backing was and continues to be a blessing. As an adult, you can find this support in networking groups and masterminds. Even if you didn’t have a high level of familial support growing up, you can get it now! And although many of these professional groups require a monetary investment, a free place to find community is in Facebook Groups. One such group is the Speak Your Way To Cash Facebook Group.

Get advice and coaching

Coaches can help you identify the skills you need to succeed in business, and they collapse time by telling you how to avoid costly mistakes that they’ve overcome.

It’s 2023. This is the year of building generational wealth for our children, in the form of wisdom, skills, confidence, and positive belief systems.

I want to help you take a step in the right direction today. If you want a free resource on building confidence as an entrepreneur so you can increase sales, dream bigger and teach your children to do the same? Get a free preview of the first 60+ pages of my book, Speak Your Way To Cash by clicking here.

About the author

Ashley Kirkwood and her husband Chris run an executive coaching firm called Speak Your Way To Cash®️. There, they train speakers, experts, entrepreneurs and authors to sell more services, land large contracts, and close licensing deals. Thousands of speakers have been helped through her book, event, podcast, and Facebook group all entitled,  “Speak Your Way To Cash®️. She’s recognized as a thought leader by Forbes, Fox32, NBC5, and more.





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