We caught up with the brilliant and insightful Sydni Joseph a few weeks ago and have shared our conversation below.
Hi Sydni, thank you for being such a positive, uplifting person. We’ve noticed that so many of the successful folks we’ve had the good fortune of connecting with have high levels of optimism and so we’d love to hear about your optimism and where you think it comes from.
I absolutely love this question, as I have been asked this since the day I entered the world. I wish I had a better answer other than that my optimism truly is rooted in the deepest parts of my being. For as long as I can remember, I have always had the intrinsic motivation to see the glass as half full, the sun when the weather app shows “partly cloudy,” and the silver lining when it feels like everything is falling apart. Remaining optimistic has allowed me to reach some of my highest highs and has gotten me out of some of my lowest lows, and for that, I am grateful. I do not have a clear indication of who, what, where, or when my optimism comes from, but I know it is always there and can confidently say it makes me the person I am.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
Of course! I am a Co-Founder of Big Plan Holdings where I began my professional career at a young age. I run point on new business development, creative brand direction, event planning and production, investor relations management, and standard operating procedures for Big Plan Holdings – with a keen focus on the cannabis industry. I am a college graduate from the University of Kentucky where I received a Bachelor of Business in Marketing along with a Bachelor of Science in Fashion Merchandising, Apparel, and Textiles. I finished my academic career with a dual degree and summa cum laude highest honors. Empowering women in business is incredibly important to me, as I fortunately have the privilege of being a young female entrepreneur myself.
I co-founded and launched a women’s luxury CBD subscription box company, 3rd Eye Hi, at 20 years old, gaining tremendous insight on start-ups, marketing strategy, B2C and B2B distribution channels, ecommerce, SOPs, budget and inventory management, and business plan development. At Big Plan Holdings, I see every cannabis deal that comes through the company’s robust pipeline – both plant touching and non-plant touching – including real estate, technology, delivery services, marketing platforms, single-tenant dispensaries, multi-state operators, cultivation facilities, manufacturers, ATM providers, funds, license acquisitions, sale leasebacks, music festivals, beverages, CPGs, and much more. I perform the bulk of the company’s due diligence, vetting each deal based on their team, path to profitability, timeline for ROI, existing industry landscape, and its potential placement in Big Plan Holdings’ existing portfolio. I prepare investor-facing materials and participates in the capital raising process for deals that Big Plan Holdings syndicates, as well. Seeing 300+ deals a year, it is my mission to offer industry-leading investment opportunities to other young women looking to safely deploy their capital into the cannabis space.
In addition, I am the Director of Special Events for American Paint – a hat design experiential retail concept in the heart of Nashville, Tennessee. I spent my last three academic years as a Student Event Manager at the University of Kentucky’s Special Events Office. During Summer and Winter breaks, I was a Special Events Assistant at Kehoe Designs – Chicago’s leading luxury event production company – where I worked on celebrity weddings, music festivals, galas, and Fortune 500 corporate events.
I currently serve on the Stevenson Foundation’s Board of Directors, is a Board Member of the Musicians On Call’s Music Industry Advisory Board, sit on the Council of the Chicagoland Chamber of Commerce’s ‘Emerging Leaders,’ and am the Chair of the Emerging Leaders’ Relationship & Networking Committee. I split time between Chicago, Illinois and Nashville, Tennessee, and I am eager to learn, grow, and network to further expand my personal and professional experience and expertise.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
I have found that the most integral parts of my journey have been strong communication, the willingness to learn, and being as worldly as I can.
As it relates to communication, my biggest piece of advice is to practice an open-door policy – encourage conversations, challenge people’s thoughts, and be a safe space for those who need it. Be the person that your peers, colleagues, higherups, etc. can rely on to effectively articulate what needs to be said, done, or understood. Being known as an inadequate communicator is never beneficial, so practice this until it becomes second nature. Lastly, remember communication comes in many forms — verbal, nonverbal, written, etc. — and the better you are at all types, the greater the professional you will be.
Be a teacher as much as you are a student and never stop learning. The moment you stop learning is the moment you stop growing. I cannot stress this enough — take every opportunity to ask questions, do a deeper dive into unfamiliar content, and surround yourself with those who are wiser and have more experience than you do.
Finally, never miss a chance to experience something new. The more people you interact with, the more places you visit, and the more things you try, the vaster your network and greater your knowledge on the world around you.
What do you do when you feel overwhelmed? Any advice or strategies?
I know I am overwhelmed when I find myself overanalyzing small inconveniences and turning them into larger stressors. As someone who strives to be as self aware as possible, I have found that the greatest thing I can do is implement physical and mental separation from anything that takes my mind back to its overwhelmed state. I get off my computer, put my phone on “Do Not Disturb,” and go for a walk or take a workout class. Physical activity while disconnected from technology has been my greatest “reset” button and helps me realign my focus and get out of my own way.
Contact Info:
- Website: https://www.bigplanholdings.com/
- Linkedin: https://www.linkedin.com/in/sydni-joseph-12801818a/

