An Interview With Chad Silverstein
Relationships are Vital: Most people focus on grades and extracurriculars but don’t bother to keep in contact with the people they meet on campus. Mathematically, there’s a good chance that at least a handful of those people will be important or know someone important. I’m not saying you should meet people just to leech off them, but knowing someone who can give you backdoor access to the exclusive party makes life easier.
We are starting a new interview series about the world of entrepreneurship beyond the classroom — a realm where theory meets grit, and education meets real-world challenges. We want to hear about critical business wisdom that often goes unspoken in academic settings. I had the honor of interviewing Lenny Richardson, owner of Productivity Accelerator.
Lenny Richardson is an Author, Real Estate Consultant, and the owner of Productivity Accelerator, a company that helps busy young professionals and entrepreneurs simplify high output in their lives. His core mission is helping other excel in life by building what he refers to as the “Pillars of Eudaimonia”.
Thanks for being part of this series. Let’s jump in and focus on your early years. Can you share who was your biggest influence when you were young and provide specific examples of what you learned from them that helped shape who you’ve become and how you live your life today?
Absolutely, Chad. I’m happy to contribute to this series. Technically, I’d say my parents were my biggest influences. While true, it’s a cliché that most people would give. So, a very close runner-up would be my junior year of high school, Literature teacher Joseph Coyle. He pushed me to step outside of my comfort zone and challenge myself.
I still recall taking Mr. Coyle’s class, Censorship in Literature, which was exclusive to students with certain grades in English leading up to junior year. As the name suggests, the course focused on books that have been discouraged, banned, or censored for various reasons. Despite knowing junior year was crucial for college, I didn’t take it seriously. In fact, I wasn’t taking most of my classes as seriously as I could have.
While most teachers were helpful, they didn’t push me to succeed. I felt like just another student in an ocean of young men at this all-boys school.
Mr. Coyle, however, would pull me aside and heavily critique my work. He’d call me out and explain how he knew I could do better. While it seemed harsh, I felt like he actually saw real potential in me. This encouraged me to work harder to live up to his expectations. During this period, I began to read more and take my work more seriously. These positive habits trickled down into my general life, and I began taking my work in other classes and extracurriculars more seriously.
I remember putting in a lot of effort on two reports after completely failing an assignment on Harry Potter and the Sorcerer’s Stone. The reports were on Fight Club by Chuck Palahniuk and Requiem for a Dream by Hubert Selby Jr. After submitting the reports and getting high scores, I still recall the note stating, “I knew you could do great if you applied yourself. You’re a diamond in the rough.” That encouragement truly helped me stay motivated in the latter half of high school and even in college. In a sense, Mr. Coyle taught me to hold myself to a higher standard and take more pride in my work and who I am.
Staying on the topic of influence, who has been your biggest catalyst more recently and what can you share that you’ve learned from them that led you to making changes in your life?
I try to draw influence from successful people. Recently, entrepreneurs like Ryan Serhant from the Netflix series Owning Manhattan have caught my attention. However, my biggest catalyst isn’t a real person, but rather a fictional character named Eddie Morra from the 2011 movie Limitless, starring Bradley Cooper. Eddie’s demeanor and rapid success are truly aspirational.
The most significant lesson I’ve learned from Eddie Morra isn’t explicitly stated in the movie but is something I’ve interpreted after watching it numerous times. In the movie, Eddie stumbles upon a pill that enhances his intelligence, allowing him to live his ideal lifestyle by getting rich, thinking faster, being more charismatic, and essentially becoming a better version of himself. However, the key takeaway for me is that being ‘limitless’ doesn’t need to come from an external force like a pill or drug.
The true secret to being limitless is having an absolute belief in yourself that you’ll come up with an answer to any problem you face. Consistently, in the movie, when faced with a problem, any character who takes the pill immediately comes up with a series of solutions. These solutions aren’t always perfect, but they provide a sense of hope and direction. I see the pill as a mechanism to encourage self-belief.
In my own life, I’ve found that my lack of progress was often due to a lack of belief. While it would be nice to simply take a pill to instill absolute self-belief, I’ve found that acknowledging doubt and shifting my mindset from disbelief to belief has been immensely useful.
In this interview series, we aim to reveal what seasoned entrepreneurs wish they had known when they were starting out and capture what the textbooks and college professors left out.
Hopefully, this answer won’t come off as too obvious, but one of the biggest lessons I wish I knew in college that would’ve made a massive impact on my life is that grades don’t matter as much as relationships. Throughout high school, nearly everyone — from my parents to teachers and even my advisors — indicated that grades were vital to lifelong success. I haven’t found this to be true in my own life, nor is it often the case for most college graduates. Sure, there are fields where good grades are necessary. My plan post-undergrad was to go to law school and become a corporate attorney, which would certainly require good grades. However, those grades wouldn’t guarantee success as an attorney, and success was my real goal.
Since graduating, I’ve worked at a law firm, where the attorneys never asked about my grades. In most careers, a student’s grades are fairly irrelevant, assuming they can produce results in their field. However, relationships have been massively important. I’ve seen numerous entrepreneurs find success primarily by meeting the right person at the right time. Even for landing a great career — arguably the goal for most college students — knowing a manager, high-level employee, or someone influential within the company is far more valuable than sending out endless resumes.
For instance, I know an engineer who lost his job during the recent pandemic in 2020. He had great grades in college but struggled to find a new job despite sending out countless resumes. Eventually, he asked around to see if anyone was hiring. My roommates at the time knew their company was always looking for engineers but wasn’t actively posting job openings. One of my friends, a supervisor at the firm, personally took the engineer’s resume to the hiring department. Within a month, he got the position because he had the backing of my roommate. Did they care about his grades? Probably not. But social proof and the referral from someone trusted had significant power.
Despite the power of relationships, nearly no college professors, advisors, or anyone else encourage students to pursue this. This is the biggest lesson I wish I had learned earlier.
Mistakes are invaluable. Can you name one specific mistake that you made early on, and learned the most from, but wish you’d been forewarned about?
One of the biggest mistakes I used to make was stressing out too much. Over the years, I’ve embraced the mantra, “Don’t sweat the small stuff. And understand, most of it is small stuff.” This sounds easy but is actually quite difficult in practice.
Throughout my student life, I stressed about so many things. I’d stress about what my peers thought of me. I’d stress about waking up late and missing a class. I’d stress about the work my professors were giving me. I’d stress about getting an 86 on a test instead of a 93. Unfortunately, I failed to recognize how inconsequential 95% of those things truly were. I can’t recall a single issue I stressed about that made a genuinely massive impact on my life.
In my opinion, the big results in life come from a lot of small activities that add up slowly over time. While I don’t have a specific instance of stress as a big learning experience, I do believe that allowing myself to be stressed throughout most of college was a massive mistake. I wish someone had warned me about this.
Is there a leadership myth you believed early on that you’ve since debunked through your real-world experience?
When I was young, I believed that great leaders are naturals, with traits genetically embedded within them. However, through real-world experience, I’ve learned that leadership is about intentional actions aimed at the positive performance of the group. Leadership traits must be developed and enhanced over time.
Many people confuse a boss with a leader. Some may hold a boss-like position, outranking others in a company or group setting, like a manager placed there due to nepotism. On the surface, it seems like they’re in this leadership position solely because they’re the offspring of the owner. But this isn’t quite the case. While they may be demanding and give orders, these managers are not true leaders and often not even effective bosses.
In my experience, a leader curates their communication, actions, and mannerisms to benefit the group and/or individual at any given time. Their behavior is not static. A leader isn’t just about commanding others but understanding and realizing that working with both the collective and individuals is the most effective way for the group to achieve their goals.
What’s the key operational insight you’ve gained since running your business that was never mentioned in any classroom?
One of the biggest insights I’ve learned, which was never mentioned in a classroom, is that what works for a few will not necessarily work for everyone. In a classroom setting, students often subconsciously believe that a one-to-many approach is efficient. We see one teacher giving a lecture to a handful or even a hundred students at a time, which can work when individuals are responsible for themselves.
However, in a group setting like a business, every employee, contractor, or staff member is important. The lagging performance of one individual could be detrimental to the business as a whole. With this in mind, taking the time to understand how to motivate or educate everyone collectively and individually is necessary.
Did college prepare you for scaling a business? What specifically was missing?
I will openly say that college did not prepare or educate me at all on how to scale a business. In my opinion, college teaches people to think within the box and perform in a manner that’s accepted by the majority. It focuses on specific, easily identifiable metrics like grades, considering them indicators of success. However, when it comes to scaling a business, those rules don’t apply.
A business can scale in a single year due to invisible metrics, like views on social media or general attention, which are difficult to track and quantify. In many businesses, standing out and separating oneself from the masses requires an owner and the company, by extension, to think outside the box. This approach is almost vital for scaling a business, at least in my current experience.
Any unexpected challenges in team dynamics that your academic experience didn’t prepare you for? How did you handle it?
My answer to this question might be a bit unexpected. When it comes to unexpected challenges in team dynamics, I believe college indirectly taught this fairly well. In my experience, the team dynamic aspect doesn’t stray too far from what one might experience in college group assignments.
There will always be a few people who are the most ambitious and contribute the most to the project. Some people do the bare minimum and nothing more. And there are those who try to fly under the radar, doing as little as possible while still hoping to get credit or reap the rewards. So, in that sense, I do think the academic experience prepared me fairly well.
Navigating team dynamics, in my opinion, comes down to understanding your role in the team, understanding the motivations and personalities of as many people as possible within the team, and playing to individuals’ strengths, weaknesses, and motivations. This is easier said than done, but I think it is the ideal strategy to ensure group cohesion.
Have you had to unlearn any widely-accepted business ‘wisdom’ in your journey? What was it and how did it affect your strategy?
Absolutely! Every year, I find myself unlearning and relearning certain things. That’s the nature of entrepreneurship — it’s dynamic. Some things work perfectly today but stop working tomorrow. I could go on for hours about the business wisdom I had to unlearn. Here are a few examples. Some will be smaller and less consequential, while others will be more impactful.
The first idea I had to unlearn is that having a website is a necessity in the modern era. While having a website can certainly help, it isn’t always necessary. However, depending on the industry, not having a website might be extremely detrimental for many businesses.
Another piece of business wisdom I’ve found incorrect is the need for an in-depth business plan before launching a business. A business plan can be unnecessary and, in many situations, a hindrance. Over the past decade as an entrepreneur, I’ve learned that taking action, even when imperfect, is much better than over analyzing and planning things out. A business plan requires too much guessing and creates a tight box to fit in. To be clear, I’m not advocating for haphazardly starting a business without any thought. However, I don’t think you need to spend months overthinking every detail about branding, attracting leads, servicing clients, or fulfilling products. No plan is perfect, and all plans are prone to unknown variables that will force you to pivot or quit.
The final piece of business advice I found incorrect is, “The customer is always right.” I hate this phrase because it’s incorrect on the surface, creates entitlement in customers, and is misinterpreted by everyone. I’ve worked my fair share of supervisory, managerial, and leadership positions. Often, I see rude or demanding customers, and their go-to line is, “The customer is always right.” I believe this phrase means the customer is right when it comes to what products to sell and how to sell them from a business owner’s perspective. It doesn’t mean that anything a customer says should be accepted because they’re willing to spend money.
Imagine a small corner store where a customer wants to buy a $10 item for $1, solely because he’s a customer and should be right. This line of thinking is nonsensical and leads to a race to the bottom for everyone.
What’s your advice for new entrepreneurs? What are your “5 Things You Won’t Learn in College But Must Know to Succeed in Business”?
- Relationships are Vital: Most people focus on grades and extracurriculars but don’t bother to keep in contact with the people they meet on campus. Mathematically, there’s a good chance that at least a handful of those people will be important or know someone important. I’m not saying you should meet people just to leech off them, but knowing someone who can give you backdoor access to the exclusive party makes life easier.
- Sometimes, Strangers are More Important than Friends and Acquaintances: This is similar to my first point. College doesn’t emphasize relationships unless you’re in a specific organization or a fraternity/sorority. Even then, the focus is on group cohesion. It’s good to have your tribe, but there’s value in constantly meeting new people. I heard a great statement: “Most people suggest it’s what you know that matters. Others swear it’s who you know that matters most. But it’s not what you know or who you know that matters. It’s how many people know you.” This insight was never shared in any college course, book, seminar, or professor’s lecture.
- Grades Reflect Memorization, But Entrepreneurship is About Execution: College courses often emphasize memorization and regurgitation, leaving little room for flexible comprehension or opposing viewpoints. Typically, professors look for specific answers. However, the real world, especially entrepreneurship, isn’t always that binary. In my sophomore year of college, I was an engineering major deciding between Industrial and Biomedical Engineering. In a chemistry class, the professor asked about a chemical equation. A far-too-advanced student suggested the answer would vary since not all details were provided. The professor responded, “Technically, you’re right. However, I’m looking for one specific answer.” This shows that multiple answers can exist for the same problem, similar to real life. If you tackle every problem the exact same way, you set yourself up for failure.
- Classrooms Teach Binary Logic, But Entrepreneurship Defies It: Classrooms teach that there are right and wrong answers, and reward or punish instantly. However, entrepreneurship isn’t about right or wrong answers. It’s about what works and what doesn’t, and what works today may not work tomorrow.
- Time is the Most Valuable Asset: College doesn’t teach strategies to learn faster, save time, be more efficient, or productive. These skills apply to all aspects of life and can make life better and easier when applied. Imagine a student who studies for 20 minutes a day and retains all the information instead of studying for 2–3 hours a day. Imagine a busy attorney who organizes her day better and gets more done with less effort, like Harvey Specter from Suits. Imagine an entrepreneur who cuts out useless work and focuses on the 1–3 things that drive revenue and profit, enjoying work-life balance. College doesn’t teach this, but these skills are vital for a successful business with longevity.
How do you ensure your team not just understands but embodies your business principles? Any techniques you wish you’d known earlier?
This is something I still work on and will likely continue to work on forever. The primary thing that comes to mind is expressing the vision of where you’d like the company and team to be, and by extension, emphasizing the why. Many team leaders, bosses, and managers expect employees to follow authority blindly. While people will follow authority, they do so solely as a means to a personal end. This means they’re not truly invested in the team, just in themselves.
If you want team members to embody your business principles, it’s important to share where the principles come from and why they exist. This helps people see things more clearly from the business’s perspective. One of the best techniques to achieve this is telling a good story. Tell a story about where the business principle came from and why you chose it. I do this all the time in my personal and professional life, and I find it helps everyone stay on the same page.
If we were sitting together two years from now, looking back at the past 24 months, what specifically has to happen for you personally and professionally, for you to be happy with your results?
That’s a fantastic question. I always measure progress through the lens of building what I call the “Pillars of Eudaimonia”. So, I’m constantly tracking these pillars of Health, Wealth, and Relationships. If I see objective improvements in those areas, I consider my time to be meaningful. With that in mind, if we were to sit together again in 24 months, I’d have to see significant improvements in all 3 of those areas. When it comes to health, this might sound silly, but I’d specifically want more defined abs.
I’ve been working on my physique for a while now and my current goal is to have more defined abs. So, if I couldn’t manage to pull that off in 2 years, I’d see that as a massive failure. Financially, I’d specifically like to see Productivity Accelerator as a more popular business. If, by that time, I could have 10–15 clients that are absolutely crushing it in life and building their own pillars of Eudaimonia, that would make me extremely happy. Finally, when it comes to the relationship pillar, outside of improving the relationship with my wife, I’d love to say that I casually go on at least one big trip a quarter. If I could make that goal a reality, and not feel guilty about it, in 2 years, I’d consider that a massive win.
Looking back over the last two years, what key accomplishments make you satisfied with your progress?
“Satisfied” is an interesting word because I’m never truly satisfied. Certainly happy or content, but never really satisfied. I can see that as both a blessing and a curse. However, if I had to list two accomplishments that get me as close to satisfied as possible, they would be writing my book 27 x 27 in 2020 and choosing not to finalize my major as an engineering college student in 2013.
Writing the book is something most people will not do. Even if only one person ever reads it, there was and still is a massive sense of achievement in taking the hours every day for several months to plan, write drafts, and eventually get the book published. It wasn’t about the sales or performance of the book itself but rather following through with a big goal. That’s why writing the book was a satisfying accomplishment.
As for not becoming an engineer, on the surface, it doesn’t sound like an accomplishment. It sounds like the opposite. But at the time, I knew that being an engineer wouldn’t set me up for the future I desired. I saw an alternative that was difficult on the front end but massively rewarding on the back end. I had no idea just how difficult life would get as a result of my decision. But I never regretted it. My life has turned out amazingly as a result, and is still progressing wonderfully.
What makes it a satisfying accomplishment comes down to pushing against what everyone told me was the best decision. It was probably one of the first times, if not the first, where I made a big decision for my own interest. Many people make decisions not to please themselves but to please others. They take jobs or careers they don’t like because of parental pressure or high expectations. They spend their time doing things that don’t really matter outside of making a handful of people slightly happy. Constantly sacrificing your future to please everyone in the present is a terrible idea and hurts everyone around you, even when they don’t realize it.
To me, it’s like a natural-born artist who becomes a doctor because his parents think it’ll lead to a more financially stable future. Sure, their intent is good, but they’re sacrificing the spirit and joy of their own son to please themselves. Meanwhile, had they allowed their son to pursue his creative passion, not only would he be happier knowing he was in control of his life, but there’s also a good chance he’d be an amazing artist, make it work, and potentially live a higher quality lifestyle than if he were a doctor.
So, making such a tough decision to live for myself is a major, satisfying accomplishment. Especially because it’s a decision I think very few people would be willing to make.
As someone with significant influence, what’s the one change you’d like to inspire that would benefit the most people?
If there’s one thing I could suggest to benefit the most people, it would be to be more open-minded. Too often, people are grounded in their beliefs and perspectives without knowing where they come from. This is a hindrance. A better life or new opportunities could literally be right in front of them. But if they’re close-minded or unwilling to try something new, they’ll always miss out and stay stuck in potentially negative situations.
How can our readers keep up with your work?
The best place for readers to find me is on my website: www.lennyrichardson.online. They can also reach out to me directly via instagram @leviticusrich. And if they’re interested in learning more ways to boost productivity without the stress, they can check out my website www.productivityaccelerator.org.
Thank you so much for joining us! We wish you only success.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
Lenny Richardson Of Productivity Accelerator On 5 Things They Forgot To Mention In College was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.