40 Lessons From 40 Years of Chris Dessi

Chris Dessi, the CEO of Silverback Social and Creator of the Westchester Digital Summit, is turning 40 years old this week. I am lucky to have literally had the chance to work side by side with Chris. Our team learns from Chris multiple times a day and I thought what better way to honor him than to share 40 of his lessons that have helped us succeed and develop.


  1. Silent Car Rides – Have a long trip with a friend, loved one, colleague (one that you like) Turn the radio off. You get to know one another on a deeper level and build a more lasting connection.
  2. Ask Questions – I’ve watched Chris control entire conversations by speaking about 10% of the time. Ask genuine questions and listen.
  3. Wait for people to finish talking – Silence is powerful. Allow people to finish their thoughts completely, wait a second and then respond.
  4. Frames – Chris read the book “Pitch Anything” by Oren Klaff probably 4 times in a row. Oren should send Chris a check for how many people he told about this book. One lesson in the book is the power of framing conversations from business development to day-to-day interactions.
  5. Don’t be afraid to poke fun at yourself – Chris is always the first one to call himself out on anything – he even has a ridiculously popular sweat schedule Facebook post that welcomes summer and winter, or when Chris starts sweating (generally April) until he finishes (generally October).
  6. Love Shiny Objects – Chris is easily distracted; he will admit it (see no. 5). Whether it’s a sunset from our office window or any other spur of the moment distraction, Chris takes a moment to live in the present and enjoy it.
  7. Get in the zone – The opposite of that occurs when Chris’ headphones go on. Lock Chris in a room with his headphones on and he could probably paint a picture, solve a Rubik’s cube and build a robot. I don’t know what he listens to, probably a band from before I was born, but having the ability to get into a zone and accomplish the task at hand is a huge asset for someone with a never-ending task list.
  8. Reach and Reverse Engineer – Chris constantly pushes the limits. If you have a great idea, don’t feel like you need to know every bit of how to make it come to fruition right away. Go for it and figure it out on the way. It’s how we started the Westchester Digital Summit.
  9. You’ve got to ask – Whether in business or life, the worst that can happen if you ask a question is someone says no and you are right back where you started.
  10. Eye Contact – Be genuine and look people in the eyes as you’re talking to them. If it’s a girl, stare until its awkward and then smile J.
  11. Meditate – Place an emphasis on mindfulness. Find 15-30 mins a day to meditate. If you are like me and have trouble focusing for 15 mins, download an App to help. Chris recommended the HeadSpace app to me.
  12. Take care of yourself – You can’t help others without helping yourself. As a business owner the work never stops but instead of working around the clock, use those hours to take care of yourself. Exercise, eat right, spend time with your family and you will be more efficient and productive in less time while in the office.
  13. Audio Books – Listening to audio books is a great way to learn, yes, but the larger lesson is make the most out of the time you have. Car rides, train rides, gym time, are all opportunities to learn that don’t take from your time with family or at the office.
  14. Watch Documentaries – Chris is always looking to learn more. The documentaries he watches are not just business, but education that help make him a well-rounded individual. He picks up lessons from everything and is quick to share with his team and apply to his life.
  15. What you appreciate appreciates – Chris is always looking for ways to help others and has been a part of multiple well-documented giving challenges that have really helped people.
  16. Family First – Our agency resides in White Plains, NY. The main reason? Chris wanted to be closer to his wife and two daughters. Almost all of our mornings at the office start on a high note because Chris comes in talking about the amazing, funny, and adorable things that happened in the morning helping Talia & Olivia get ready for their days at school.
  17. And Also Second – When Chris’ father was sick, he was always ready to drop everything to be with his dad or to help his mother. He has worked from hospital rooms and through the night to get his work done after his responsibility to his family was fulfilled.
  18. The Importance of your Wife – Chris often credits any success that he has as an entrepreneur to the support and assistance he receives from his wife Laura. I’ve never heard Chris speak negatively about Laura, and we spend A LOT of time together. Instead, he lights up with excitement when he tells stories about her, when she calls or when he recalls stories about when they were first dating. I am not married, but I learned a lot about the qualities to look for in a spouse from hearing Chris speak about Laura.
  19. The What if Game – Chris fondly talks about when he and Laura were first dating and they would walk throughout NYC and talk about scenarios if money were no object – where would you shop, what would you buy, where would you live, where would you travel. Not only were they spending quality time together but also they were building the vision for their dream future. Don’t be afraid to dream big, paint the picture; you may just be able to make it a reality.
  20. The Power of the Conjure – Countless times Chris has mentioned a person or an action out of the blue and shortly there after we heard from that person or the action came to fruition. We call it “conjuring” and we all have the ability to do it.
  21. Have you ever made an exception? In customer service situations, Chris almost never gets impatient. He simply asks the person “have you ever made an exception?” If the person says yes, Chris responds with “Would you be willing to make one here?” I’m amazed by how often this works.
  22. Don’t sell, teach – When I met Chris he was already an accomplished salesman. He taught me that the best selling is education and if you show people why your product/or service will really benefit them, you’re never really selling.
  23. Cultivate Relationships – Chris remains close with friends from grammar school up through high school. As individuals mature and families grow, this becomes harder and harder to do. Chris makes a point of keeping in touch as often as possible. If he were ever in a bind, there is a huge list of people who would drop everything to help him. In fact, I met Chris through a friend of his from first grade.
  24. Empower the people you are managing – Chris invests in his employees. No one is more confident in his or her employees abilities than Chris. He is quick to give them the support step out of their comfort zone and reach for new heights but also quicker to support and help them learn from any mistakes they might make.
  25. When given an opportunity say yes before you can be scared – In 2009 an EMS driver was fired for posts he made on Facebook about his employer. It was an emerging story and Fox needed an expert to talk about it. They called Chris and that afternoon he was on National TV.
  26. Be Yourself – The Fox news producer found Chris by Googling “social media expert” and coming across Chris’ blog post entitled “If You Claim to be a Social Media Expert, You’re Full of Shit” and even wrote an updated post on the subject recently.
  27. Even when you’re good, you can always get better – After five years of regular TV appearances and speaking engagements Chris sought the assistance of an on-air news trainer. He learned so much from that training that he went from good to great with his appearances and presentations.
  28. We are all human – When I first started working with Chris we were networking with extremely successful individuals (and we still are). Where I was instantly intimidated, Chris would walk right up to anyone and start a conversation. Within minutes, there would be laughter. Be confident in your abilities to bring value to people no matter how senior, good looking or intimidating they are.
  29. Value your time – Your time is your most valuable asset. Lunch meetings are great but more often than not, that’s two hours out of the office plus the time it takes to get back in to a good work rhythm. Chris has taught me to make the most of my days: calls instead of meetings, 15 minutes instead of a half hour, and many other ways to maximize my productivity.
  30. Lead from the front – When we engaged a very large client Chris worked around the clock while on the first “vacation” he had taken in 3 years. It was hectic, not relaxing, but necessary and he never questioned that, just did what had to be done.
  31. Substitute Complaints for Recognition – Chris rarely ever complains. Instead he focuses on offering recognition to others. One of my favorite things he taught me is to send a surprise email or text to someone listing three reasons why you admire them. I’ve done it twice and it has lead to two incredible conversations. I need to do it more.
  32. Don’t forget where you came from – Chris is always willing to make time in his schedule to speak at events both at Loyola where he attended college and in Mahopac where he grew up. In fact our first Digital Summit outside of Westchester was in Baltimore where Chris offered free or discounted tickets to alumni.
  33. Can’t Beat Custom – Chris always made sure he was dressed for success. He clued me in to the fact that if you’re willing to wait 3-4 months for your clothes, you could get custom shirts/jackets for the same price as you would in a department store. As a rite of passage he purchased custom shirts for his first three Silverback Employees to welcome them to the team.
  34. Get Your Shoes Shined by an Expert – Sounds silly, but appearance translates in to confidence, which translates in to success. Chris bought me my first shoe shine in Grand Central a few years ago, and I can’t say I closed any deals that day but I felt like I could take over the world.
  35. Embrace Boring – I like to move at a fast pace. Occasionally Chris will ask me how my weekend was and I will say “boring”. His lesson is, enjoy it. As life goes on and you start a family, boring is hard to come by. Embrace it.
  36. Email: Less is More – Sometimes when I am writing an important email I will have Chris look it over. The final product is usually a third, sometimes a quarter less than what I originally wrote and 100% better. Remove the fluff, get to the point and the recipient will appreciate it.
  37. Write an Angry email but don’t send it – We all get those emails that just frustrate us. Our first instinct is to hit reply and start typing. Go for it, get it all out. Read it, read it out loud if you have to, and then delete it. If it requires a response at all visit the next day when you’ve had an opportunity to sleep on it.
  38. Put things in perspective – In a fast-paced society, especially in New York, we are quick to let little things bother us. A nasty email, missed opportunity, extended commute. When Chris’ father was sick he would talk about perspective and how small and trivial a lot of the things we are quick to get upset over are. You shouldn’t have to have a sick loved one to realize that, it’s the case for all of us. Think big picture.
  39. Slow down and Enjoy the Journey – When you have goals, it’s easy to get caught up in the “What’s next,” “How can we get there,” and “We need to move now.” Take the time to enjoy the process and have reverence for how far you’ve come. This will help provide the motivation to keep going.
  40. Another Chapter in the Book ­– Often times if we have a bump in the road, we talk about how it will be another chapter in the book that we write after we achieve our goals. Failures, mistakes, course corrections happen. That doesn’t mean the outcome won’t be exactly what you planned for or even exceed it. Next time you get thrown a curveball just write it off as another chapter in your book of success.


Earlier this month Chris’ father passed away after a six-year battle with ALS. By the time I started working with Chris, Adrian Dessi was already confined to a wheelchair, having some difficulty communicating. Throughout knowing Chris and the few days of services for his father, a picture was painted of a genuine, hard working, honorable, brilliant man full of life and love for his family. I was bummed that I didn’t have the opportunity to know Adrian in his prime, before he was sick. Then I thought about it and realized so much of what Chris is, of the 40 lessons I just mentioned, he learned from his mother and father. I may not have known Adrian well, but I am learning from him, through Chris, every day. Cheers to the next 40 years and countless lessons.


Learn anything from Chris in the last 40 years? Share it here as an added benefit for all.

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