We recently connected with Jaden Oluwayomi and have shared our conversation below.

Hi Jaden, thanks for joining us today. We’d love to hear your thoughts about family businesses.

Owning a business has been an incredible blessing for our family. One of the things I cherish most about being an entrepreneur is the opportunity to work side-by-side with my husband every day. Running Journey Digital Solutions together has allowed us the flexibility to work from home while raising our young children—a gift we don’t take for granted.

But let’s be honest: working with your spouse isn’t always easy. In the beginning, small misunderstandings sometimes turned into bigger conflicts. I remember a time early on when we would argue over something as small as a social media post. Miscommunication and pride got in the way more than we care to admit.

Over time, we’ve learned that the keys to success—both in marriage and in business—are communication, grace, and respect. We don’t always agree on every decision, but we’ve learned to value each other’s opinions, even when we disagree. For our business, we’ve divided responsibilities based on our natural strengths and interests, but we’re always ready to step in and help each other when needed.

Journey Digital Solutions actually began as my side hustle before we got married. When my husband started getting more involved in the daily operations a year into our marriage, it was a tough adjustment. I had built this business myself and felt I knew what was best. Letting go of that control and handing over responsibilities was hard—I was stuck in the “this is my business” mindset. Shifting my perspective to see this as our business took time, but it transformed how we work together. Now, we approach everything as partners—both in life and in business—with an equal vote on opportunities and decisions.

Ultimately, we’re building this business not just for ourselves but for our family and future generations. Family businesses are an amazing way to create financial freedom and generational wealth, but that only becomes a reality if the next generation builds on the foundation you’ve established. Would I want my children to join our business someday? Absolutely—but only if it’s their passion and calling. At the end of the day, the legacy we’re building isn’t just financial; it’s about showing our children the value of teamwork, resilience, and chasing their dreams.

Family businesses come with their challenges, but the rewards—both personal and professional—make it all worthwhile.

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

I’m the founder of Journey Digital Solutions, a digital marketing agency specializing in helping service-based businesses grow their online presence and connect with their customers online. My journey into the marketing world began while I was working full-time in the nonprofit and government sectors.

I quickly realized that I had a passion for crafting digital strategies that are not only effective but also deeply human-centered. Because the goal is to build lasting relationships with your community so they become repeat customers. Over time, that passion evolved into a full-fledged business where I now get to work alongside my husband, serving incredible clients in industries like SaaS, real estate, healthcare, and more.

Can you tell us about a time you’ve had to pivot?

We are currently in the process of pivoting our business to support business owners in all stages of their growth. Our business currently offers digital marketing services, such as email marketing, SEO, social media, and more. Now, we’re developing a course for entrepreneurs to grow their businesses on social media without sacrificing precious family time or burning out. This course gives the exact strategies to reach customers online without being stuck to your phone 24/7.

Not all business owners are ready to hire someone to do their marketing, especially organic social media. This course will help equip those small business owners with the strategies and tools they need to build a successful social media presence. As the needs of business owners evolve, our business is committed to helping support in the best way possible.

We’d love to hear about how you met your business partner.

Some people say they don’t mix business with pleasure, but I believe that is the best way to build a small business. If you aren’t passionate about what you do, you’re more likely to give up when times get difficult. And they will get difficult at times.

Like many others today, I met my business partner and now husband on a dating app. At the peak of COVID-19, we started our long-distance relationship where he was working at a university in North Dakota, and I was working in marketing at a small non-profit in Colorado. We traveled back and forth each month so we could spend a couple of days together. We truly connected over our beliefs and passion to build a life that would bring a positive influence to those around us. One way we are achieving this goal is by building a business that helps other businesses grow through marketing their products and services.

Contact Info:

• Website: https://journeydigitalsolutions.com/
• Instagram: https://www.instagram.com/your.social.journey/
• Facebook: https://www.facebook.com/JourneyDigitalSolutions
• Linkedin: https://www.linkedin.com/in/jadenoluwayomi/

Image Credits

Photographer: https://www.instagram.com/innerimagesphotography/

Highly recommend her for all branding shoots