I was a senior in high school during the 2008-2009 financial crisis. I watched as my mom went through a bankruptcy and a foreclosure. That experience, along with the birth of my son when I was 18, changed my life.
I had been business-minded as a kid, selling books on Amazon in middle school and baked goods in high school. But being a parent motivated me. It crystallized for me the importance of entrepreneurship.
Pursuing my side hustles has meant freedom and limitless earning potential, even when I had so much on my plate. For over 10 years, I was a single mom, raising two boys after my second child was born in 2014. There were times when I went to school while running a side hustle and working two other jobs. As time went on, I mastered the art of juggling multiple responsibilities and making it work.
In August of 2019, nine months after earning my MBA, I left the corporate world, where I had worked for a number of years in human resources, to become a full-time entrepreneur. Today, my husband and I run six businesses together. They are all profitable and bring in over $10,000 each month.
Here is what we've learned.
Before we got married in May, both my husband and I were both running two companies full time. We each lead hectic lives, but even with adapting to the realities of the pandemic, we understood that we could be better together. So we decided to combine forces to help grow our companies to new heights, even while things are so uncertain.
My companies are Money Talk With Tiff, which provides financial education and coaching that I launched in 2017, and DanJai's Natural Products, a homemade soap company I started in 2013. His businesses are Fly Dye Clothing Company, a custom tie-dye apparel company that he also started in 2013, and a video production firm he's run since 2005.
As newlyweds with four businesses and two kids, we had to figure out quickly how to make it all work. One thing we learned was to utilize each other's strengths.
While I'm not a natural salesperson, my husband can sell salt to a snail. We decided that he would take the lead when it came to promoting our businesses and reaching new customers. It doesn't matter where he goes, he is always talking about at least one of our companies.
But I am phenomenal at digital marketing and creating efficient admin processes. Things that would take him forever to do take me no time at all, so we decided that I would handle all the back-end tasks for each business. I created and managed all our websites and social media presences.
So I take the lead on bookkeeping, accounting, and human resources for the contractors we work with, like the freelancers who handle social media and PR support for Money Talk With Tiff. Dividing and conquering this way has allowed us to cover more ground and stay focused.
Since March, when our kids were sent home from school at the start of the pandemic, we have been working to find balance. But our side hustle passion hasn't dimmed. Over the last few months, we decided to start two additional ventures together.
We own a rental property, and in May we began developing land for another set of units. We also launched our logistics company, CatMan Express, LLC in July of this year. We began as a local courier business delivering office supplies, but now we move all types of freight around the country. And even though we launched in the midst of the pandemic, it hasn't slowed us down. As an essential business, we have been able to stay up and running.
So while our forays into logistics and real estate brought us up to six companies, we aren't intimidated by the scope of the work, because we have a system in place that helps us prioritize. We each have a main focus, which brings in the most income: For him, it's CatMan Express, LLC and for me, it's Money Talk With Tiff. The other four we consider our smaller side hustles.
Video by Stephen Parkhurst
In a given week, if we find ourselves running short of time, we turn our attention to our main businesses. This step is crucial because it prevents us from putting valuable time in a business that is not as important as another. Time management and flexibility is a big thing for us.
CatMan Express has my husband traveling for at least three weeks at a time. When he is home, he designs clothing items for Fly Dye and schedules as many video and photo shoots as possible for his video production company. That way, we can have products to sell on the website after he leaves to hit the road again.
And while my Money Talk speaking engagements have been canceled due to the pandemic, I have been able to pivot to holding events online. It isn't quite the same, but I've been making it work.
Video by Courtney Stith
It was always important to me to teach my kids everything I know about business and show them how they could support themselves in this way. So one of the most gratifying things about being an entrepreneur is getting my boys involved in our businesses.
Lately, they have been a big help with our tie-dye apparel company Fly Dye Clothing Company. The kids help us pick out colors, name products, and practice on their clothes, so when they get older, they can help out with the family business. The kids love telling their friends about our businesses and have even made some sales themselves. They are already talking about what companies they would like to own when they get older.
We all hold each other accountable and make sure we are progressing towards our individual and family goals. We are each others' sounding board and support. Sometimes that looks like reminding each other to put a new business idea on hold so we don't get spread too thin. And we remind each other to relax and take it easy when we start to feel overwhelmed.
When I was just starting out, my grandparents and my mother were, and continue to be, a tremendous help. When I was working on my MBA, they watched the kids two nights a week for three hours while I went to class after I had already worked my full-time job from 8-to-5. I'm so grateful for them. If I didn't have them, none of this would have been possible.
Ultimately, my best advice for anyone who is looking to start a business or side hustle right now is to find a strong support system, whether it's friends, family, or even fellow side hustlers. For entrepreneurs, that community is crucial to helping you and your ventures thrive.
Tiffany Grant of Money Talk With Tiff is an award-winning personal finance blogger, podcaster, coach, and educator. She has paid off over $50,000 in debt and has a goal to be debt-free by 30. She has helped many people become more in tune with their money by providing financial education in a down-to-earth and relatable format.
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