When we originally opened the bakery component, we assumed that families would steer clear of us because the dispensary was on-premise; we thought that a lot of parents might not want to be seen bringing their kids into a cannabis dispensary despite the bakery. We were wrong — families, especially those with kids, have been coming in since day one.
Scott Weiner: How Merging Hospitality, Craft Food, and Cannabis is Revolutionizing the Consumer Retail Experience
The Fifty/50 Group leader shares insights on breaking down mainstream stigmas, introducing legal consumption lounges, and navigating the evolving cannabis landscape in Illinois.

As part of my series about “5 Things I Wish Someone Told Me Before I Started Leading a Cannabis Business” I had the pleasure of interviewing Scott Weiner.
Scott Weiner — a Northbrook, IL, native — traces his love and passion for the restaurant and hospitality business back to taking his first job waiting tables at Johnny Rockets as a teenager. Working at a variety of other restaurants in the Chicagoland area, Scott focused and prepared for a career in the hospitality industry at an early age.
Upon graduating high school, Scott moved to Las Vegas where he spent four years as a cook at various concepts with China Grill Management while simultaneously earning his bachelor’s degree in hospitality administration, majoring in beverage management, from the University of Nevada Las Vegas. While in college, Scott also earned his sommelier license through the Court of Master Sommeliers. Prior to opening his first restaurant, The Fifty/50 in2 March 2008, Scott worked with Lettuce Entertain You managing Joe’s Seafood, Prime Steak, and Stone Crab in Chicago where he focused on operations while rounding out his education surrounded by great leaders and mentors.
Today, Scott captains the leadership team of the Fifty/50 Group, helping create and develop new concepts, and he is responsible for the day-to-day financial success of the group. A key to the group’s success has been developing and managing their own assets over their 15- year history while also managing properties for private equity groups such as Blackstone, Beacon Capital, the CME Group, Marquis Development, First Hospitality, Second City Theaters, and more over the years. The Fifty/50 Group currently owns or manages 21 different concepts across the Chicagoland area and is in construction or development in eight more establishments that are slated to open over the next three years.
In 2019, Crains Chicago named Scott to the prestigious 40-under-40 list. He is also an active officer on the executive board for the Illinois Restaurant Association, serving as the vice chairman while focusing on government relations. Scott volunteers weekly at the Friendship Center in Lincoln Square personally cooking 150 dinners per week for those in need and resides in northwest Chicago with his wife, two boys, and a dog named Balki Bartokomous.
Thank you so much for doing this with us! Can you share with us the story about what brought you to this specific career path?
I am a local restaurant operator of a Chicago-based company called the Fifty/50 Group. A few years ago as I became aware of and a guest at various cannabis-focused dinners that were popping up across the city, I started to look for think about the various ways that cannabis, food, and hospitality all intersected. That drove me to look for various opportunities to break into the space, and eventually, I met the right partners that shared similar values and believed in the idea.
Can you share the most interesting story that happened to you since you began leading your company? Can you tell us what lesson you learned from that?
When we originally opened the bakery component, we assumed that families would steer clear of us because the dispensary was on-premise; we thought that a lot of parents might not want to be seen bringing their kids into a cannabis dispensary despite the bakery. We were wrong — families, especially those with kids, have been coming in since day one. Often times mom or dad goes next door into the dispensary while the other parent stays with the kids.
What I took from this, was that there is still a lot to be learned about people’s relationship with cannabis at various times in their life and certain stigmas that might have been there 2–3 years ago in an area like this are breaking down.
Can you share a story about the funniest mistake you made when you first started? Can you tell us what lesson you learned from that?
I spent a lot of time working with our agents in the inventory area when we first opened. We definitely purchased much more products than we needed, and I spent a lot of time learning about the different skus. I still have a relatively low tolerance for THC and I got a little too ambitious with this infused pre-roll that was maybe 45% THC.
I learned to take it slow and while there are so many products out there that seem amazing, I probably will never enjoy that type of product. When looking Flower that is low in THC, I notice that there are very few strains in Illinois less than 18% THC. I wish there was a flower out there around 10%, and it should be called Training Wheels.
Are you working on any exciting projects now? How do you think that will help people?
We are under construction on the next two OKAY Cannabis Experiences which include the bakery and bar component. Two of them will also have consumption lounges with the first consumption component opening in June.
We are working with a local group called AMPLIFY, which works with and mentors youth that have touched the justice system. We’ve hired 8 of them for our city location and we are looking forward to creating a way for everyone to get involved in the cannabis industry.
I also love seeing that the OKAY concept will offer consumption in Illinois. It’s still rather unique to see near Chicago, legally, and I think that it will continue to help make cannabis use a normal part of everyday society.
From a non-cannabis side of my business, we are working on four restaurants, one of which is in partnership with one of the Midwest’s best-known craft brewers who has a taproom in Indiana, just outside of Chicago. Later this year, we are also opening a small bar & restaurant at the Second City that is being built in Brooklyn. We have a lot of exciting “pinch me” projects in the works.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
I’ve been fortunate to have a great group of partners and co-workers in the Fifty/50 Restaurant Group. Having a supportive company infrastructure and amazing professionals has allowed me to focus on a lot of the fun stuff.
This industry is young, dynamic, and creative. Does your company use any clever and innovative marketing strategies that you think large legacy companies should consider adopting?
A lot of our marketing has so far been geared toward the uniqueness of our establishment. We pay a lot of attention to what our competitors are doing, one of which bought out every billboard within every direction of us for the first 3 months of us being open. Right now, I’d say that I’m learning from the competition. The innovativeness for us is in our experience which ultimately is very unique to our market and is still evolving.
Can you share 3 things that most excite you about the Cannabis industry? Can you share 3 things that most concern you?
- I’m excited about the future of hospitality, food, and cannabis. I think it’s only in its infancy.
- I’m excited to see all of the new people who are getting into this business from various walks of life.
- I’m excited to see the “craft grow” revolution take over in Illinois.
- I’m nervous about banking and tax laws. Because vast elements of the cannabis industry are still underground and not legal federally, it ultimately creates a lot of vultures that take advantage of people in the industry. I also think that the absorbent sales tax rates that Illinois charges is going to become a major deterrent if they don’t match what other states charge.
- I’m nervous about the legacy market. I recently had a friend show me an app and website from a legal cannabis company that delivers to people’s doors in Chicago. They undercut taxes and they are also buying from Michigan because of how cheap their flower is. Extremely professional operation with regular drivers… I was even more terrified to learn that the company doing this actually is a legal cannabis entity from Michigan that is behind this as they are struggling to survive in Michigan and turning to illegal behavior.
- In general, I am also nervous about delivery. As a restauranteur, I saw what bad actors like Grub Hub, Uber Eats, and others did to restaurants and to drivers both.
Can you share your “5 Things I Wish Someone Told Me Before I Started Leading a Cannabis Business”? Please share a story or example for each.
1. If you build it, they won’t always come (right away). It’s a more established market than I had thought in Illinois, and we will have to grind.
2. Restaurant management mentality is a lot different than Retail. I last worked in retail about 27 years ago, I’m 42, and I forgot how different it is.
3. There are some first-generation cannabis industry people that are not happy about seeing the industry change too fast.
4. Craft Grow was going to be very very late to the party in Illinois due to all of the hoops they’ve had to jump through. My business model might have been slightly tweaked. I am ultimately selling the same product that my competition is.
5. The POS systems are all in their infancy and there are only a few out there that aren’t harvesting your customers’ data…
What advice would you give to other CEOs or founders to help their employees to thrive?
For me, a relative outsider in this industry, I’ve been getting in the trenches when I can with my hourly employees. Our hourly agents are the superstars, and I don’t know if my employees are thriving yet, but I’ll find out sooner being on the ground floor with them.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
I’d start a movement today to outlaw all television, radio, and billboard advertising for Kars for Kids. I think that those constant commercials are the source of roughly 12.5% of this country’s anxiety and general anger.
What is the best way our readers can follow you on social media?
@scottthe50 on Instagram
@okay.dispensary on Instagram
https://www.facebook.com/okaydispensary
This was very inspiring. Thank you so much for joining us!
Authority Magazine Editorial Staff
Editorial Desk · Authority MagazineThe Authority Magazine Editorial Desk produces, verifies, and edits long-form primary-source interviews with executives, innovators, clinicians, creators, and social impact leaders across Business, Tech, Pop Culture, Wellness, and Social Impact.

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