We recently connected with Diana Jacobs and have shared our conversation below.
Alright, Diana thanks for taking the time to share your stories and insights with us today. Alright, so one thing we think people don’t talk about nearly enough is investments – either time or money. What’s one of the best or worst investments you’ve made and what did you learned from the experience?
As a business owner you definitely have to be prepared for ANYTHING and also listen to the ones who you know for a fact has your BEST interest!
Last year I was blessed to be able to bring my vision to life for my fourth business. I budgeted everything, met my deadlines, obtained a lot of help with this event, and was successful in executing everything. The problem was that I should have scaled back drastically and made a realistic goal of attendees. Even my best friend (since second grade) suggested that I might need to scale thigs back, but NOOOOOOOOOOOO I just had to keep everything I already did and kept the goal as the same. Do not get me wrong the event turned out to be wonderful to the point guest were asking me if I can bring the event to their city and guest did not believe me when I would tell them this was the 1st Annual event for the brand, but I learned that my vision was too big for the brand!
I was expecting 200 people and 60 people attended. Sixty people is still a lot for it to be my first huge event for the brand, but when I tell you I did not make a penny……..I didn’t even pinch a penny compared to what I put into it LOL.
This investment was definitely a loss (not my first L), but I LEARNED from it!
If I had listened to my best friend, I would have made a profit, if I would have stopped and thought things through more, I would have made a profit. Oh well, because as a business owner you must be prepared to expect some L’s, but always make sure you learn from them. You also must check yourself and be real with yourself at times. No one is perfect and no one is alike, so it is always good to remember that you are creating your own blueprint, and everyone gets the same 24 hours in a day so make sure you know what you are going to do with yours.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
Born and raised in Toledo, Ohio. I am a Junior, my mom named me after her. My background is Criminal Justice. I have both a Master’s and Bachelor’s degree in CJ from Bowling Green State University. I have a beautiful 10 year old daughter that is my everything! In 2016 I decided that I finally wanted to create a 501(c)(3) non-profit youth program for both young men and women. I stated reaching out to other’s who I have seen in a position that I wanted to be in. Almost everyone that I reached out to regarding the process told me they “did not have the time to help me and/or they paid someone to do it for them”. That right there told me that I needed to sit my butt down and learn how to do it myself. I filed all the required documents and submitted everything. Thirty days later I received mail from the IRS and Ohio Secretary of State informing me that everything was correct, and that Kings & Queens Youth Program is an active non-profit in the state of Ohio. This led me to looking into how to create sufficient LLC’s, EIN’s, and over the years more. This also allowed me to create the second business Loner Inc. Loner Inc. was created in 2018 and has been assisting with business start-up with a 99% accuracy/approval rate.
From 2016 to 2018 I was still working a 9-5 while running my youth program and Loner Inc. September 2018 I decided after having my convo with God to take a leap and resign so I can put all my energy into my businesses. Keep in mind I’ve been working since I was ten years old at a friend of the family restaurant. Ever since then I’ve always worked, even multiple jobs at once. Making this decision was scary, but since I trust God, I knew he wasn’t going to fail me and I’m sure not going to fail myself!
The rest of 2018 was hard financially, to the point I started working dead-in jobs. I thought to myself what the point of me resigning from the job I had in my field, so in 2019 I created a plus size boutique called Pretty & Thick boutique. Business ran slow, in addition to learning how to certify, open, and operate a food truck. Then in 2020 COVID-19 happened. With COVID-19 happening that opened the door for Loner Inc. Everyone wanted to start a business which was a great thing for everyone.
Opening my boutique probably was not a smart move at the time, but that’s another L amongst my L’s through this journey, but I learned from that L and can always fall back on it if need be.
In 2021 I opened my fourth business Sitting Pretty Stoned. SPS provides your everyday stoner needs and is currently in the process of being rebranded, I also have two great friends that approached me about becoming partners, so now I am happy to be able to have business partners with this business. I’ve always done things by myself so having two additional brains, in addition to knowing they want the best for you and the brand is a bonus! I’m looking forward to seeing how far we will be taking Sitting Pretty Stoned!
I’m still learning every day and you should so you can get better at your craft. Generational Wealth is the main goal for my people and me. Consistency & Patience is the two main components that goes along with being a business owner, and always remember to be PROUD of yourself no matter what happens!

Let’s talk about resilience next – do you have a story you can share with us?
When I decided to resign from my job, I did not have any financial back up at all! All I knew is that I had my talk with God, he told me that he got me no matter what, and everything else will be figured out! Well let me tell you, when I had to pawn stuff to make my rent then that’s when I had to tell myself that I wasn’t putting enough work into my craft! You still must put the work in no matter what.
September 2023 will make it my fifth year being self-employed, and I plan on keeping it that way and continually growing in every aspect of my life,
I sometimes get asked the question “How did you know you were ready to make that step to becoming a business owner?”, and all I can say is that you will know when God and/or your preferred higher power speaks to you and when you are tired making money for someone else. Everyone’s journey is their own journey, so do what work for you. We as people cannot compare ourselves to the next person that may be in the position you are working towards, until then just make sure you clap for them all the time while you are working and waiting patiently for your flowers.

Can you talk to us about manufacturing? How’d you figure it all out? We’d love to hear the story.
Back in 2018 after I resigned from my job, I also thought I was going to start a t-shirt business. I thought wrong, because I was able to press one shirt and gave up after that when I couldn’t press another shirt LOL. Now fast-forward to 2023 and my business partners and I are pressing our own apparel for Sitting Pretty Stoned.
The difference between 2018 and now is that I did the research and learned from another good friend this time. This friend was learning the shirt business last year and would ask me different questions about it, but I honestly couldn’t help her because my t-shirt business was short lived. Once my business partners and I decided to do production on our own, I knew exactly who to turn to for help. She helped us with no problem and helped us out a lot.
As a business owner you always want to do your research and be around people that are like-minded. People who don’t mind helping or providing information. It’s money out here for everyone, so why not assist others…..we all get the same 24 hours in a day it just all depends on how you execute YOUR 24 hours.
Contact Info:
- Instagram: Sittingprettystoned419
- Facebook: Sitting Pretty Stoned
- Other: [email protected] [email protected] [email protected]

