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Hayley Luckadoo: From College Dropout to a Serial Entrepreneur



Hayley Luckadoo from College Dropout to a Serial Entrepreneur

Please state your name, your position, and a bit of your Business.

I’m Hayley Luckadoo, serial entrepreneur, motivational speaker, and business coach. In addition to my speaking and hosting the Females on Fire podcast, I currently run my digital marketing firm, Luckadoo Media Co., where we help entrepreneurs and small business owners reclaim their time and build their online presence. I offer courses and a coaching program for women in business and spend my days focusing on creating content that empowers women to create a growth mindset, go all in, and turn their “what if’s” into tangible realities.


How did the business start?

I was about to head into my last year of college (after having finally settled on a Criminal Justice major after trying just about everything) and was engaged to the man I’d been dating for almost 6 years. I had a rock bottom moment – my fiancé left one month before the wedding at the same time I found out my financial aid had been cut and I wouldn’t be able to complete my last year of school. I knew I had to do something to pay the bills, and couldn’t handle the idea of getting another job in retail or waiting tables.

Even though it hadn’t worked out, I had just planned my own wedding, so I knew I had the skills to do that and I had plenty of friends getting married. I convinced them to pay me a little and refer me to their friends. Within 6 months, I couldn’t take on any more clients and realized I needed to learn how to run a business.

I ran my wedding planning business for almost 6 years, but in my 3rd year, I started helping other wedding professionals with the back-end and marketing side of their business, because I realized that was the part of running a company that I was so passionate about. Everyone I helped told me I should be doing this professionally, so I told my husband of only a few months that I wanted to start a second company.

My small virtual assistant company has transitioned and grown so much in the last 3 years (which is why I finally stopped planning weddings) and is now a digital marketing firm where my husband also helps out, called Luckadoo Media Co. We help entrepreneurs reclaim their time and grow their online presence, and I love the work I do with that company.

In the last 18 months, I also started a coaching program for women in business, launched some courses, and started the Females on Fire podcast, which is where I found my love of speaking. Since then I started booking stages and conferences as a motivational speaker and found that it’s the biggest passion in my business thus far.

Needless to say, it’s been a crazy journey to this point and has been 6 years full of ups, downs, and tons of transitioning, but I can’t imagine being more passionate than I am and I love the ever-changing world of entrepreneurship that I get to be in.


What are the challenges you met and how did you manage to cope up with these challenges and reach your current status?

I started with nothing but challenges since I had no idea how to run a business. By the time I felt like I had a handle on it, I started a second company in a completely different industry, which is practically like starting over. I’ve faced all your typical challenges in business – from having to learn new things to not having enough people on your team, to dealing with clients who weren’t the best fit to work within the first place – but I always remind myself of where I started and how resilient I’ve always been. The simple reminder that I have always and will always figure it out (whatever it is) is enough to get me through whatever setback I’m facing at the moment.


Who influenced you in this industry and how did he/she influence you?

This seems like a copout answer, but I couldn’t possibly just pick one influence. I believe if you want to constantly keep learning and growing, you have to find a way to learn something from every person you come into contact with, which is what I’ve always done. Everyone has something they can teach you, even if it’s a way NOT to do something. You just have to pay attention and be willing to find the lessons. I’ve learned so much from so many people, but I also believe that everything you’ve ever wanted to know exists somewhere on the internet, free of charge. You just have to put in the work to research and find it.


How did you manage to market your business and compete with other agencies in your niche?

My marketing strategy has always been pretty simple. Where is my customer at right now / What platform are they on? And how can I best serve them and solve a problem for them in this season of their life/business? Once you answer those two questions, you have your marketing strategy and the only thing left is deciding how to best implement it. You can spend all day learning every platform and spending tons of money on ads, but if you aren’t solving the problem your customer actually has, then you won’t get anywhere. Don’t overcomplicate it – just meet them where they’re at.


What Best Practice/s can you share to our startup readers?

Take big risks. We often let the fear of failure, other people’s opinions, or our own excuses stop us from taking the risk that could take us to the next level. You have to let your ambition be bigger than your excuses. The worst that can happen is that you learn how not to do something and it takes a little longer than you wanted to get there. It’ll be so much worse for you if you wait and find out you should have tried sooner. Take the risk.


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  1. Pingback: Katherine Adams: Founder of Creative Legacy Group - The Weekly Trends

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