An Interview With Chad Silverstein
Let people underestimate you and they’ll undermine themselves. That turned out to be more practical than I expected.
In the world of business and within every industry, there are forward-thinking leaders who go against the status quo and find success. Their courage to take risks, embrace innovation, and inspire collaboration separates them from the competition. Until 2002, Apple’s famous slogan was “Think Different”. This attitude likely helped them become one of the most successful organizations in history. This interview series aims to showcase visionary leaders and their “status quo-breaking” approach to doing business.
As a part of this series, we had the pleasure to interview Jacob Schlichter.
Jacob Schlichter is a Minnesota-based entrepreneur, photographer, and founder of The Smoking Tree — the first state-licensed micro retail cannabis operation in Minnesota. A longtime advocate for cannabis legalization, he was present at the signing of HF 100 alongside Governor Tim Walz when adult-use cannabis became law in the state, and has since defended those laws through his own legal efforts tied to his business. He is also the creative founder behind SLICKS, a fashion-forward brand focused on culture and identity, and is known across regulated industries and creative ventures for building businesses grounded in execution, long-term thinking, and genuine community investment.
Thank you so much for joining us in this interview series! Our readers would love to get to know you a bit better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?
The first thing I think about when someone asks about growing up is our house next to the train tracks in southern Minnesota. When trains went by, they’d shake the whole neighborhood. I remember the nearby park and the corner mart where we’d get donuts and snacks. I was lucky to grow up on a street where neighbors didn’t mind us being loud or cutting through their yards. I was a curious kid — always asking questions, probably to the point of annoying people.
From early on I was drawn to understanding why things were the way they were. I naturally gravitated toward different groups of people and tried to figure out how social dynamics worked. I was extroverted by nature and spent a lot of time socializing both in and outside of school. I genuinely liked being around different personalities. At the same time, I never felt like I fully belonged in just one place, which pushed me to find common ground with a lot of different kinds of people.
I was a big reader and would stay up late sneaking in extra chapters. Books like The Phantom Tollbooth, Fahrenheit 451, and the Hardy Boys series shaped how I think about imagination and problem-solving. I also grew up reading National Geographic and MAKE Magazine, which fed a real interest in how things work — wildlife, space, exploration. I was constantly building with LEGOs, Lincoln Logs, and Erector sets. Hands-on thinking came naturally.
I didn’t realize it at the time, but I also loved the flow state that came from physical activity. One of my favorite things in elementary school was the mileage club — I’d spend most of recess running laps. I carried that into track and cross country later on.
My home life gave me both structure and independence. My mom emphasized discipline and respect for authority. My dad emphasized practicality and resilience. My step-parents pushed independent thinking and forming my own perspective. It was a good mix, even if it didn’t always feel that way at the time.
We always had pets, which I think built early empathy and observation skills — something that later became important in my wildlife photography.
Academically I was consistent. Honors classes, decent grades, orchestra, sports, science olympiad, chess club. I got Character Counts awards and worked as a teacher’s assistant for a while. I took that stuff seriously.
Outside of school, I spent a lot of time in games like RuneScape, Club Penguin, and Call of Duty. Those actually helped me build real friendships and understand how groups work. At some point I moved into leading teams in multiplayer environments — building groups that sometimes had hundreds of people. Being that young and responsible for a group that size was intense. I had to learn how to delegate, keep people engaged, and coordinate against competing groups. I didn’t always get it right, but I was getting real experience in leadership without realizing it.
A big chunk of my teenage years I lived on my own, which forced a level of self-management most people don’t deal with at that age. It accelerated my independence fast. Fortunately it didn’t isolate me — friends would come by, give me rides, keep me included. I also had close friends online from around the world.
In high school I started exploring entrepreneurship and creative work while holding down jobs at the same time. Gaming evolved into creating digital assets — fonts, clothing designs, in-game items. I learned basic coding and ran my own server. Then photography took over my senior year and opened the door to everything creative that came after. I’m still grateful to my photography teacher for taking a chance on me and lending me one of the school’s cameras.
My senior year I was involved in a serious snowmobiling accident that caused a TBI and a long recovery. About a year later, I lost a close friend to addiction. Those two things changed how I think about resilience, responsibility, and looking out for the people around me.
Looking back, my upbringing wasn’t linear, but there was always a pattern: observe, explore deeply, build something, turn the experience into something useful.
Can you give us a glimpse into your journey into this industry and share a story about one of the most significant challenges you faced when you first started out? How did you end up resolving that challenge?
My path into this industry wasn’t something I planned. After high school I was dealing with a lot of uncertainty and trying to figure out what direction to go. A friend encouraged me to try cannabis for the first time — something I’d previously been strongly against. I did my own research, realized it wasn’t what I’d been taught growing up, and that sparked something.
That curiosity eventually turned into action. I went from being a casual consumer to building a cannabis fashion brand, then working as the apparel head for Tommy Chong’s brand. During that time I also volunteered to educate people about cannabis use and helped register thousands of people to vote. That work led to me being present at the signing of HF 100, standing alongside Tim Walz and Jesse Ventura when adult-use cannabis was legalized in Minnesota. The work has since extended into defending cannabis laws through my own legal efforts tied to his business registration.
Most people assume the biggest challenge I faced was legal or public-facing. But honestly, the hardest part has been personal. I’ve lost multiple friends to addiction over the years. That changes how you see everything — substance use, education, harm reduction, all of it.
Losing people close to me forced me to approach this space differently. I became more focused on education and prevention, and on creating alternatives that help people make better decisions.
Channeling that grief into something constructive wasn’t easy or clean. I had to learn how to let emotion drive action instead of letting it stall me. Over time that became the resolution — building, educating, contributing in ways that might actually help someone else.
What started as curiosity turned into responsibility, and eventually into a long-term commitment to this space that’s grounded in experience and purpose — not money, hype, or ego.
Who has been the most significant influence in your business journey, and what is the most significant lesson or insight you have learned from them?
Honestly, I can’t point to one person and feel good about that answer. There are too many people who’ve played a real role, and singling out one wouldn’t be accurate. They say it takes a village to raise a king, and I feel that in my bones.
All four of my parents shaped my foundation in different ways — discipline, practicality, independent thinking, and the freedom to pursue my passions as long as I had a plan behind them. My grandparents, the ones I was fortunate enough to spend time with, each left something with me too — a sense of community, an entrepreneurial spirit, and some early lessons about how to carry yourself in the world.
One of the most useful things I was taught young was to never show your full hand. Let people underestimate you and they’ll undermine themselves. That turned out to be more practical than I expected. When my business registration was denied and people tried to spread rumors to discredit me, none of them knew I had already accounted for major legal challenges in my business plan for The Smoking Tree. I had thought it through well in advance. They assumed they knew what they were dealing with. They didn’t.
I’ve also had people in my professional life — managers, collaborators, people I’ve worked alongside in this industry — who showed up for me consistently during some genuinely hard stretches. That kind of steady, quiet support from people who didn’t have to give it means a lot and has shaped how I try to show up for the people around me.
There are more people I could name, and I wish I could do all of them justice here. But the common thread is this: think ahead, stay true to what you’re building, and surround yourself with people who actually believe in you.
Can you share a story about something specific that happened early on that you would consider a failure but ended up being a blessing in disguise or ended up being one of the most valuable lessons you had to learn on your own?
Early on I launched my first cannabis-oriented fashion brand with a small group of partners. Things started well — there was real momentum and a shared creative energy that felt genuine.
Over time it became clear we weren’t aligned. Priorities started to diverge. Expectations that had never really been spelled out started creating friction. Eventually the partnership broke down entirely.
On top of that, I was dealing with a lot of personal pressure at the time, so it felt like multiple things were unraveling at once.
What I took from it is that business partnerships really are a lot like marriages. Growing up around divorce, I recognized the pattern — but I recognized it too late. By the time we were having the real conversations about roles, expectations, and direction, too much had already compounded for it to fully reset.
What I should have done from day one: treated it like a long-term commitment. Been explicit about intentions, strengths, limitations, and what everyone was actually bringing. Without that clarity up front, small misalignments just keep stacking.
It wasn’t just a failure — it was probably the most useful thing that happened to me early on in terms of how I think about choosing and structuring partnerships. That lesson has shaped every collaboration I’ve entered into since.
Leading anything is hard, especially when grappling with a difficult situation where it seems that no matter what you decide, it will have a negative impact on those around you. Can you share a story about a situation you faced that required making a “hard call” or a tough decision between two paths?
Not too long ago, my cannabis business registration was denied. That left me with a real decision to make.
Option one: accept the outcome, stay quiet, move on. Option two: challenge it — knowing it would bring attention, cost time and money, and make everything more complicated.
Neither was easy.
What made it harder was that it wasn’t just about me. There were employees depending on the outcome and investors who had committed capital. And if I chose not to act, I was also potentially contributing to a pattern that could affect other business owners navigating the same process.
I chose to challenge it. That came down to principle. I wasn’t willing to accept something I believed needed to be questioned — especially when the implications reached beyond my own situation.
The hardest part wasn’t the decision itself. It was stepping into a more visible position where you don’t fully control how things unfold or how they’re perceived. That’s uncomfortable.
Two things helped me stay grounded through it. First, I did a lot of research and worked with professionals to understand my position clearly — that helped me feel more confident and communicate better when things got stressful. Second, having people around me who were supportive made it easier to keep moving with clarity instead of getting stuck in the uncertainty.
Let’s shift our focus to the core of this interview about ‘Successful Rule Breakers’. Why did you decide to “break the rules”? Early on, did you identify a particular problem or issue in how businesses in your industry generally operated? What specifically compelled you to address this and want to do things differently? Please share how you went about implementing those changes and the impact they had.
Early on I noticed that a lot of operators were moving through the licensing process one step at a time — treating each requirement as its own isolated task. That approach created real delays, especially in a regulatory environment where timing and coordination matter a lot.
Under the Office of Cannabis Management’s structure, you had to secure a physical location, complete a full buildout, and be ready to operate before you could even qualify for a state license. That’s a significant upfront commitment — leasing a space, preparing it for inspection — before you had approval in hand.
Finding the right location alone added time and complexity. On top of that, we had to prepare detailed SOPs as part of the application, meaning compliance and daily operations had to be fully documented before anything was even reviewed.
My approach was to run those things in parallel rather than sequentially. I worked directly with local government contacts to stay aligned on zoning and compliance, kept communication open across relevant departments so questions could get answered as they came up, and built in real adaptability — having contractors ready during inspection phases so adjustments could happen on the spot instead of triggering delays.
That combination — preparation, direct coordination, and real-time flexibility — let me move through a still-developing regulatory system without giving up compliance, quality, or timing.
The result was becoming the first state-licensed micro retail license holder in Minnesota. That was a meaningful milestone, and it came directly from treating the process as something to be navigated strategically rather than just checked off line by line.
In the ever-changing business landscape, how exactly do you decide when to adhere to industry norms versus “breaking the rules” and forging your own way? Can you share an example?
I don’t really think in terms of “breaking rules.” I think more about whether a norm is still doing what it was originally meant to do — or whether it’s just become a habit that nobody’s questioned in a while.
A good example is the idea that you have to “work your way up” through formal channels before you can talk to anyone who matters. In practice, I’ve found that’s mostly a social expectation, not an actual rule.
If I believe in something or see an opportunity, I reach out directly. I’ve cold emailed and cold called owners and decision-makers at much larger companies to pitch ideas or start conversations, with no formal access point or introduction. Sometimes it works. Sometimes it doesn’t. But I’ve never operated from the assumption that I need permission to communicate.
The principle underneath that: if one path isn’t working, it’s fair to look for another one — as long as you’re operating ethically and not compromising your values in the process.
That said, I think it’s worth being clear about the difference between questioning outdated norms and ignoring boundaries that exist for real reasons. Legal, ethical, safety-related rules aren’t “norms” — they’re limits. There’s a real difference between finding a smarter way to do something and cutting corners.
The goal is never to break rules for its own sake. It’s to stay intentional about which structures are actually necessary and which ones are just habits — and to move through the world with your integrity intact.
What guidance or insight can you offer to new entrepreneurs trying to follow existing and accepted industry norms while at the same time trying to differentiate themselves in the marketplace?
Once you actually understand how an industry is structured, you start to see the difference between what’s necessary and what’s just habit. That gap is usually where there’s room to do something differently.
A lot of entrepreneurs try to skip the foundations and differentiate too early. In my experience that creates more problems than it solves. You have to understand how an industry works before you can credibly challenge any part of it.
I’d also say: it’s okay not to be first, and it’s okay not to get it right the first time. I see a lot of people my age get completely paralyzed — by fear of failure, fear of being judged, fear of confrontation. That hesitation keeps people from ever starting.
The most important move is just to act. Start. Learn. Adjust. Keep going.
It’s easy to overthink whether something’s been done before or whether you’re doing it perfectly. None of that matters as much as people think. What matters is execution and perspective.
At some point you have to give yourself permission to try — not because the outcome is guaranteed, but because the cost of not trying is almost always higher than people realize.
If you genuinely want to do something, it’s worth finding out what happens when you actually do it.
Here is the main question of our interview. To make an impact, you have to champion change, get creative, and take risks. Please think back about the decisions you’ve made that have helped your business get to where it is today, and share your top 5 strategies or decisions that helped you succeed by doing things differently.
1. Moving quickly without waiting for perfect clarity
I’ve never waited for perfect conditions before taking action. When I was pursuing my state license, I knew there would be obstacles and things to revise along the way. I moved forward anyway, focused on learning fast and adapting rather than stalling until everything was certain.
Practically speaking, that meant securing a location and starting early-stage planning before every variable was locked in. Waiting for full certainty would have delayed the whole process. Moving when I did kept me ahead while others were still preparing.
2. Direct communication instead of working through layers
I’ve always preferred going straight to the source rather than relying on assumptions or intermediaries. Throughout the licensing process I stayed in consistent contact with city and state representatives to confirm requirements and keep expectations clear.
There was a specific moment where I received guidance that, after reviewing it closely, didn’t fully align with my reading of the actual statutes. Instead of moving forward blindly, I went back to the source language myself and asked more questions before acting. That process helped me avoid a decision that could have set me back significantly — and it reinforced that staying engaged and asking direct questions matters, even when you’re working with experienced professionals.
3. Staying close to execution and knowing when to own it directly
I stay close to the work throughout — not just at the start. I delegate when it makes sense, but I take direct ownership of anything where quality or outcomes really depend on it.
For the licensing and buildout, I handled most of the preparation and documentation myself rather than outsourcing it. That gave me a much deeper understanding of the process and let me respond quickly when adjustments were needed, instead of waiting on back-and-forth.
4. Watching for friction and fixing it in real time
Once you’re in the details, you start seeing exactly where time and energy are being lost. I focus on those points early and make adjustments fast.
One example: I coordinated contractors to be available during inspection windows so that if something needed to change, it could be handled on the spot. That eliminated the scheduling delays and follow-up visits that would have otherwise slowed things down. Small improvements like that don’t seem like much individually, but they compound.
5. Building flexibility in from the start
I rarely plan around a single expected outcome. I build in contingencies so I can adjust when things shift.
During the licensing and buildout process I planned for multiple scenarios around timing, approvals, and operational readiness. When things changed — and they did — I could adapt without losing momentum or having to restart major parts of the process. That flexibility made a real difference.
As a leader, how do you rally others to align with your vision? Also, how do you identify those who may not be fully committed or even silently sabotaging or undermining your efforts? What steps do you take to address these situations?
Rallying people starts with clarity. I make sure everyone understands not just what we’re doing, but why — and what success actually looks like day to day. When expectations are clear and direction is consistent, alignment usually follows through execution. You don’t have to keep selling people on a vision if they genuinely understand it.
I try to build teams where people are self-motivated and bring different strengths than I do. I don’t assume I have all the answers. Surrounding myself with people who complement my blind spots makes the whole operation stronger.
I also lead by example. When standards are high and I’m consistent in how I execute, it sets the tone without me having to say much.
When it comes to spotting misalignment, I focus less on intent and more on behavior over time. Consistency, follow-through, communication, ownership — those things tell you what you need to know pretty quickly. When they start breaking down, it usually shows up in execution before anyone says anything directly.
I also try to remember that misalignment isn’t always about attitude or commitment. People are dealing with things outside of work, and that affects performance. I pay attention to where someone’s head is at and try to understand the full picture before drawing conclusions.
In most cases I address things directly through a conversation first. My goal is to understand the context, clear up any ambiguity, and see if alignment can be restored. A lot of misalignment comes from unclear expectations or miscommunication — and that’s fixable once it’s named.
But not everything gets fixed. If issues persist, or if trust breaks down and doesn’t recover, I don’t force it. I adjust responsibilities or restructure the team so everyone can stay focused and effective.
Throughout all of it I try not to operate from frustration. I assume most problems come from misalignment or outside stress rather than bad intent — while still making whatever decisions protect the work and the people doing it.
Imagine we’re sitting down together two years from now, looking back at your company’s last 24 months. What specific accomplishments would have to happen for you to be happy with your progress?
Two years from now I’d want The Smoking Tree to be running with real stability — not just surviving, but operating smoothly with strong internal structure and a team that knows their roles and has what they need to do them well.
A big marker of success for me is the people. I’d want to see a team that’s genuinely growing in their roles, with long-term opportunity in front of them, and a real sense that they’re part of something worth sticking around for.
Beyond the internal side, I’d want the business to be in a position to give back in a more intentional way. That might look like supporting local organizations like the Albert Lea Art Center, contributing to education around addiction awareness, or being involved in community initiatives tied to harm reduction and public health. Those things matter to me and I want the business to reflect that.
More broadly, I’d consider the last two years a success if the growth was stable and responsible — if we grew without losing alignment with the values the business was built on. Growth for its own sake doesn’t interest me. Growth that improves the environment around it does.
At the end of those 24 months, I’d want the business to be stronger, the people involved to be better off than when they started, and the work to be contributing positively — both inside and out.
You are a person of enormous 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. 🙂
If I could put real energy behind one thing, it would be building healthier, better-informed, more connected communities — through education, support, and genuine access to resources around addiction, mental health, and opportunity.
The place I’d start is how we talk about addiction. So much harm comes from stigma, misinformation, and people not getting help until it’s too late. If we reduced that stigma, leaned harder into harm reduction and early intervention, and gave people better tools to understand risk, I think outcomes would improve significantly. I also believe there’s a strong public health case for expanding legalization and regulation of certain substances within a structured framework. Regulated systems reduce harm, improve safety, and create accountability that unregulated markets simply can’t offer. The goal is to help people make more informed decisions and get support without judgment.
Alongside that, I’d invest heavily in local communities through education and the arts. Places like local art centers do something that’s hard to quantify — they create connection, give people somewhere to belong, and open doors for expression and creativity, especially in smaller communities that often feel overlooked. Those spaces matter more than people realize.
And I’d push for real civic awareness. People should understand how their government works and have meaningful ways to engage with it. I’d want to see more transparency and more accountability when institutional decisions hurt individuals or communities. A healthy society depends on people having the tools to actually participate in the systems that shape their lives.
Of course, this is all easier said than done. But I think a little effort from all of us goes a long way toward leaving the world better than when we were born on it. I’m not just talking about our kids here — I’m talking about our great-grandkids and beyond. Are we actually doing things that set them up for a successful future? That’s the question I keep coming back to, and I think it’s one worth taking seriously.
How can our readers continue to follow you or your company online?
You can continue to follow my work and updates through the following platforms:
The Smoking Tree: https://www.TheSmokingTree.com
SLICKS: https://www.GetSlicks.com
Photography: https://www.JacobFox.Art
Everything Else: https://www.JacobTheFox.com
Thank you so much for sharing all of these insights. We wish you continued success and good health!
About The Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Jacob Schlichter Of The Smoking Tree On Successful Rule Breakers was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.