Conversations with Jessica Dalby

Today we’d like to introduce you to Jessica Dalby.

Hi Jessica, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I am the CEO of Diggie The Progression Of Hip-Hop LLC & P.U.S.H. Entertainment. My husband/business partner Robb Dalby and I are retired from the United States Army. My husband retired from Fort Leavenworth, Kansas. We chose to make Kansas home and bought a house in Leavenworth, Kansas. Leavenworth and Kansas City has become our community and a place we love. 

We went to several events in Kansas City to support the local independent artists and cultivated some very long-lasting professional relationships. My husband always wanted to have a podcast discussing hip-hop culture, music, and its impact. When the pandemic hit there was so much divisiveness and disruption going on in society. Therefore, my husband grabbed a composition book and began to write down ideas and thoughts. I opened my cell phone and looked at him and said, “which podcast microphone do you like”? 

What initially started out as an idea and a vision on a clean sheet of paper in April 2020 has transformed into a full-blown company and movement. A video/audio podcast surrounding the hip-hop culture and music. The humble beginning steps in April 2020 launching on YouTube. Meeting LL Cool J on Instagram Live on May 20th, 2020. Establishing the business Diggie The Progression Of Hip-Hop LLC in August 2020. Creating our Clothing brand. Launching on all music audio podcast platforms on September 11th, 2020. 

Moving forward to establishing P.U.S.H. Entertainment in April 2021 as a full-service entertainment, artist development, business consulting, and management company working under the umbrella company Diggie The Progression Of Hip-Hop LLC. Creating and producing quality podcast shows, and amazing interviews. Cultivating a unique brand that encompasses inclusivity, and unity, and keeps social injustice awareness at the forefront.

I immediately saw the bigger vision and knew this was more. In less than 24 months in business we have peaked at #9 on the Apple Podcasts chart in the United States under music history. We are ranked in the top 10% globally. We have surpassed 1.4 million views on our YouTube channel. Our reach is global and now we look to revive the entertainment industry, music scene, and the arts in Kansas City. I believe it is time and accept the challenge. 

We all face challenges, but looking back would you describe it as a relatively smooth road?
I believe that without struggles you cannot reach higher levels in life and business. I have faced many struggles. From self-doubt to professional business financial struggles, I don’t regret any of it. Although, there were obstacles and challenges I have overcome them and continue to do so. I have learned from them. It has further propelled our business in more ways than none.

Taking a leap of faith as an entrepreneur is hard. It is scarier when you go all-in financially. However, I have done everything since day one with passion and purpose. As an avid researcher, I have chosen to always continue to educate myself. Seeking out a SCORE mentor and learning all the correct ways to establish a business. Listening to others but doing the research myself regarding our core target market and how do we stand apart.

The best rewards are from obstacles and challenges. I do not see myself as an entrepreneur. I am the CEO of Diggie The Progression Of Hip-Hop LLC and P.U.S.H. Entertainment. I pride myself on professionalism, transparency, and integrity, and love what I do.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I am self-taught. I established my business structure. I established a Duns & Bradstreet business profile. Outside of my husband/business partner, I run the businesses. He is the host, and content creator, and does the post-production. However, I love challenges and facing them head-on. I always say I do a little of a lot because that is the truth. I handle the day-to-day operations, the financial books, bookings, event planning, marketing, formulating new professional relationships and fostering those relationships, and with the most professional and purest intentions. I am not an expert in everything, but I like to say I can do just about anything that is thrown at me. I believe serving in the military has strengthened me to take on multiple roles and has propelled our businesses/brands to higher levels.

I am well versed in the entertainment business and that is something that is often overlooked. The music/entertainment industry in my opinion is 90% business and 10% talent. Therefore, understanding the ins/outs and all-around business side is helpful in continuing to propel our platform to higher levels. 

I will say that those who know me do know I am always supportive. Supporting whether it be via social media, purchasing merchandise from artists, or from local small businesses, doing the best I can to help get artists and businesses names out there and even out of Kansas City to other markets, etc. I believe support when genuine is most rewarding.

I have a platform I worked hard to build to the heights it has presently achieved, but one thing is my loyalty is strong and there are several artists, businesses, etc. in Kansas City that I will always support and look to work with and grow with. As a business, we have joined the KC Chamber of Commerce and are fostering relationships to push the needle, elevate, and put Kansas City back in the conversations as in my opinion they should be in. The remarkable talent that lives right here in our Kansas City community. A culmination of the arts. The priceless opportunity of cultivating this with surrounding businesses in Kansas City. The quality over quantity perspective. In business we often see competition. I see growing together and elevation. Everyone can shine and succeed together!  

What has been the most important lesson you’ve learned along your journey?
I continue to learn throughout this journey. However, I will say that the most important thing I have learned was that when you start something you are passionate about you will begin to see who truly wants you to succeed. Trust your intuition. Never be afraid to ask questions. Do your research. Always remember at the end of the day you are investing in your career or business whatever that may be and it’s important to do that with people who are professional and transparent. Lastly, when you feel like you just don’t know what to do whether it be artist development or aspiring to start a business and need business knowledge, I am here to help, and you can schedule a free 30-minute consultation with me. If I can’t help you, I will do what I can to try to point you in the right direction. We all have dreams. Now we turn those dreams into reality, professionally, strategically, and growing together for a flourishing Kansas City that will no longer be overlooked.  

Contact Info:

• Email: [email protected]
• Website: www.diggiea2.com
• Instagram: https://www.instagram.com/jessicadalby/
• Facebook: https://www.facebook.com/OfficialDiggieTheProgressionOfHipHopLLC
• Twitter: https://twitter.com/DiggieA2
• Youtube: https://www.youtube.com/c/DiggieA2TheProgressionofHipHop
• Other: www.linkedin.com/in/jessica-dalby

Image Credits
Cristina Popovic Photography