Key Learnings
Hard-won lessons from a team of accomplished leaders — each one expanded by AI with real-world evidence.
Browse by theme
- Business: Business (26) · Entrepreneurship (60) · Leadership (58) · Business Strategy (34) · Sales & Marketing (23) · Customer Experience (4) · Execution (29)
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Browse by thought leader
- Chuck Rutledge (5)
- Dan Lynn (89)
- Elazar Aslan (12)
- Steven Goldthwaite (1)
All 107 Key Learnings, newest first
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Let Them Walk to the Bus Stop
When we raised our kids, my wife and I built our approach around a few core beliefs: we wanted them to be independent, to know how to work, and to experience the natural consequences of their own…
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Never Eat The Last One
My mom was a wonderful lady. She gave me a lot of great advice over the course of my life. But a few of the ones she gave me when I was a teenager are the ones I still smile about — and still think…
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Ask and You Shall Receive
Asking for referrals has always been a big part of my sales process. Then, while at ADP, I helped develop the company's client referral program. And later in my career I founded a technology company…
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The Fire Was Always Burning
There's a widespread belief that work and life have gotten harder, and that organizations are more dysfunctional than they used to be. Part of that is fair. Some workplaces are genuinely better run…
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Count the Votes Before You Get to the Senate Floor
One of my bosses at ADP, Brad Smith, had a saying I've carried with me ever since: "Count the votes before you get to the senate floor."
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Work Like It's a Mission, Live Like It's an Adventure
Some of my most inspiring people I know share a trait: they don't treat work like a job, they treat it like a mission. They work incredibly hard because the work has meaning to them, and they carry…
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Life Happiness Formula
Years ago, my life felt like it was running me. I had a demanding job, I was getting my MBA at night, and I had two kids under the age of two at home. Every hour was spoken for, and the things that…
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Choose Your People, Not Just Your Position
I’ve worked as a research engineer, product manager, project manager, and in marketing and business development—at Fortune 500s, early-stage startups, and nonprofits. Across all of it, one pattern…
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You Have Arrived.
In 2003, I bought a BMW 530i.
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The Steak Story
There is a steakhouse in Brooklyn, New York, that is the epitome of a big city steakhouse. Not only does it have career waiters and original wooden floors and furniture, but it is actually very good.…
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Eddie and the Parrot
It was one of my family’s best traditions. Every summer my father would rent a beach house for a week down the famous Jersey Shore, in the southern part of New Jersey. All my siblings came from…
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Bits & Bytes
It was my last interview for a senior marketing position with this Fortune 100 company. I needed to meet with the CEO for his final nod. The only issue I had was that I’m a Marketing person, he a…
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Princeton
It was a time before most parents began taking vacations to scout colleges with their teenage kids. To help you select and get in to your college of choice, there were books, guides, and those…
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Shwarma
There is a middle eastern food called shwarma. Actually it is called many things and it is made of many things. A revolving vertical spit made of lamb or beef or turkey or probably at times, mystery…
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Getting Directions
It was an interview disguised as a dinner. I had met with the CEO in New York, for a possible assignment of major scope. Although the multi-hour meeting went well, he felt a meeting with the Board of…
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Boardwalking
It was a summer day, though it was late September. A perfect evening for a stroll on the boardwalk. I wasn’t alone in my opinion as the boardwalk in Ocean Grove, NJ had a lot more people doing the…
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The Pebbles
My fiancé and I were preparing to go on a ten-day silent retreat. I had been many times over the years, she only once before. Regardless of one’s “experience,” each retreat carries its own power. We…
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Punch-Buggy
My girlfriend taught me a game she used to play when she was a kid. Since I didn’t spend my early childhood in America, there was always another game, story or tradition that I would need to learn. I…
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Scheherazade
I have very fond memories of my childhood in Iran. I don’t know if indeed it was good or those memories are some euphoric recall. I have older siblings and many, many cousins—we all remember it…
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July 4th
I love fireworks. I’m not sure where that attraction came from, but I can barely remember a time that I wasn’t in total awe of them. Perhaps it was when I was a child in Iran and we would go, by…
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The Rainbow Room
I don’t know if it was just Murphy’s Law haunting me that day or the anxiety of a first date with a woman who I thought might be “the one.” That particular day, though, was a series of ongoing…
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The Retirement Spending Wedge
A good friend of mine spent his career as VP of HR for a manufacturing company. He was older than me, and over the years he watched hundreds of colleagues retire. He also watched what happened to…
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The Napkin and the Envelope
In the late 1990s, ADP was recruiting me away from AT&T. The courtship started with a dinner with Brad Smith — yes, that Brad Smith, who would go on to become the CEO of Intuit. It took me about ten…
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Lunch Money
When I started at ADP in 1997, I met a great, ambitious salesperson named Scott Delea. We hit it off instantly, and we discovered we shared the same dream: someday, each of us wanted to build a…
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Start At Zero
We have all sat through the corporate ritual. The meeting room settles, the leader opens the floor, and the instruction is given: "Let's go around the room and share a bit about our backgrounds."
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Some Bushes Can't Be Trees
In 1998, I was promoted into a new VP of Marketing role at a Fortune 500 company and inherited a team of very talented people. They were great at what they did — traditional, old-world marketing. The…
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Forming, Storming, Norming, Performing
During my MBA, I learned a simple model about how teams develop. Nearly thirty years later, it may be the thing from those classrooms I quote most often.
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Buckets
Most problems are one big complicated mess. It's hard for people to get their arms around them and know how to start. "I'm not happy at work." or "My life is crazy and I feel out of control." Stated…
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They Can't Even Define Intelligence, Much Less Measure It
I wasn’t the best student. It wasn’t that I didn’t like learning. I did. I was curious about all kinds of things. The problem was that they weren’t always the things I was supposed to be learning. I…
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Back In Black
I had a wonderful, life-long friend named Dave Kreutzer. We grew up in the same neighborhood. In high school, we were allowed days off to visit colleges. So one day Dave and I borrowed a friend's…
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If You Can Get 1, You Can Get 100.
When you're testing marketing campaigns, lead generation programs, or sales plays, you have to try a lot of things. Most of them won't work. That's not failure — that's what testing is.
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Behind The PBX
In 1990, I was just starting my sales career at AT&T. One morning I got a frantic call from my contact at McGettigan's Travel — a great, historic Philadelphia travel agency, still run by the…
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Gone To Lunch
Early in my career, I was always too busy for lunch. I'd skip it entirely, or I'd run down to the cafeteria, grab something, and carry it right back to my office so I could keep working. To me, that…
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My Car Was Stolen. My Car Was Stolen.
My first car was a 1983 Mazda RX7 GLX. Silver exterior, red leather interior, stick shift, fully loaded, with that unique RX7 rotary engine. It was the kind of car you'd walk away from, then turn…
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A Clear Blue Sky
Early in my career, I was in sales at AT&T, in an office in Bala Cynwyd, Pennsylvania — top floor. One April afternoon in 1991, a colleague suddenly yelled: "Oh my god! Oh my god! I just saw a plane…
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Congratulations! Well, Kind Of.
When I started in sales at AT&T in 1988, I did ride-alongs with some of our best salespeople. You learn more watching a great rep for a day than you do in a week of training.
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What She Saw In Me
One of my bosses back at AT&T, Mary Upchurch, shaped my career in many ways. But there's one thing about Mary that mattered more than all the rest.
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What Kind of Leader Will You Be During The Tough Times?
I had a great boss at AT&T named Mary Upchurch. I learned a lot from her — lessons I've carried through my whole career.
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Left to Right Thinking?
If you've read my "Right to Left Thinking" post, you know how my mind works. I start with where I want to end up — a specific goal, a real date — and I work backward to today. It's served me well for…
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But Maybe They Really Should Match
My first job out of college was at Marine Midland Bank, in the World Trade Center in New York City. My mom was so proud. "My son is a banker," she'd tell people.
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The Lyin' King
When I started my career at ADP, I was a Director of Marketing. This was 1997 — and back then, AOL was one of the most powerful companies on the planet.
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The Pregnant Pause
When I worked at ADP, one of the senior-most leaders was an ex-McKinsey consultant. Initially, I had a really hard time connecting with him. Our meetings just didn't flow.
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Half & Half
Back in 2003, I was on a flight, sitting next to a woman I'd never met. I started a conversation and at one point she asked me what I did.
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The Girl Got Hot
There's a great Weezer song called "The Girl Got Hot." There is one line that says "What used to mean a little now means a lot”. It's about someone who used to get overlooked suddenly becomes the one…
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Just One Thing
Early in my career, I landed a tough new job — the kind where you feel like you have everything to prove. So I did what ambitious people do: I went away and built a plan. Not just any plan. A really…
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When Things Are Going Great - Panic!
The moment you think things are going great and you are exceeding your targets is exactly the time to force yourself and your team to worry. Building a business is so hard and takes so much out of…
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There Are No Right Answers
The most important thing I learned while getting my MBA was that there are no right answers. Sure, there are to math problems but not to business strategies and decisions. There are really no right…
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The Idea, The Idea, The Idea
So you want to have your own business do you? What are you going to do?
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The Dream
Ever since I started working, I dreamt about having my own business. I'd actually lay awake at night trying to come up with the idea. I told everyone I met that some day I would have my own business.…
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Managing a Small Business in a Difficult Economic Environment
Well, the good news is that we finally started a business. The bad news is that we picked the absolute worst time to start a business. March of 2000 wasn't exactly the perfect time to get started. In…
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The Power of Now
While doing some deep research on how the mind works, I learned that most of us spend our time somewhere other than where we are. We replay the past or worry about the future, and the moment we're…
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We Will Have Fun - Damn It!
In my experience, a company's culture typically reflects its owners or leadership. During the first 3 years of our start-up venture you could summarize the culture in one word - "Serious". Well, you…
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Nobody Likes Change
When I was in high school I frequently visited the local gym to work out. The place was a mess. It had a very small work out room. The mirrors were cracked. The bars were bent after years of use. The…
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Champions Come Out At Tournament Time
I love March. Spring is just days away. Baseball is in the middle of Spring Training. The Masters is not far away. The NCAA Tournament (aka March Madness) has just tipped off. It's an exciting time…
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Is It Just Noise or Is It Relevant Noise?
In 2004 we built an AI business called RelevantNoise. That's right, over 20 years ago we built an AI-powered technology platform that leveraged machine learning and natural language processing. It…
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The Essence is the Moat
I had an interesting insight about AI while building this platform.
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Follow The Goosebumps
Have you ever sold something that gets you so excited that it gives you goosebumps when you talk about it? Well, it is an amazing feeling. It's easy to sell because customers can feel your passion.…
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The Possibilities of Tomorrow
Remember, people don’t buy from you just because of what you can do for them today. They also buy from you because of the possibilities of what you will be able to do for them tomorrow. So, make sure…
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The Glass Is Half Full
If you're coming out of college right now, I know the job market feels brutal. Applications disappear into the void, entry-level roles are scarce, AI is replacing a lot of entry-level roles, and it's…
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Happiness is in the Experience
My wife and I were sitting outside having breakfast at a little restaurant in Florida. It was a beautiful day—the perfect temperature—and the restaurant had an incredibly vibrant energy.
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Man in the mirror
When my father was about 88 years old he told me "the man I see in the mirror is different than the man I see in the photo on my driver's license. The photo on my driver's license is that of an old…
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A Vortex of Your Own Doing
"A vortex of your own doing." I say it all the time — usually to myself but also to other driven professionals.
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Climb the Ladder. Just Not That One.
We spend our whole lives climbing the ladder. That's the deal we're handed early: work hard, reach the next rung, then the next — more responsibility, more income, more security. And for most of your…
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When the Noise Stops
Some friends of mine were commodity brokers in New York. One day I went to visit them, and they took me to a booth that looked down over the trading floor. It was pretty amazing to see — the floor…
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A Fair Exchange of Value
In my advisory work, I say this all of the time: "It has to be a fair exchange of value." It's one of the basic concepts I've learned throughout my business career — an unfair deal will eventually…
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If you believe…
When I was a young manager at AT&T, one of my bosses was a former BCG consultant named Bob Napor. Our job was to help AT&T's executives make big decisions by framing the issues clearly. I'd just come…
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How To Get Started
The big question I had when starting the business was where to get started. How do you prioritize and focus? Do you build the infrastructure so that you can do the work? Do you hire people who can do…
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The "A-Team"
Obviously, when you are starting a company, you want to hire the best possible people. Everyone will tell you that. Yes, my advice is the same - hire the best possible people. However, I would also…
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The Voice in Your Head
There's a voice in your head and it's not you. What? Yep. Most people laugh when you say that. But, it's true. It narrates, judges, worries, replays — almost constantly. Most people never notice it,…
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Do Something
You have a choice - do something or do nothing. In my experience, doing something is the right choice. So, do something.
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On a scale of 1-10
Here's something I've said my whole career. On a scale of 1 to 10 — 1 being the worst, 10 being the best — a 1 is better than a zero.
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Points of Leverage
At some point, every company ends up in a room that really matters — a funding round, a strategic partnership, an acquisition. And here's the thing most people miss: the leverage you have in that…
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More Good Than Bad
When I was building my company, I'd call my wife on the drive home. She'd ask how my day went, and my answer was almost always the same: "Good and bad — but more good than bad."
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Work Happiness Formula
I've had a long career and spent a lot of time in different types of jobs and various types of projects. Over time I learned what the drivers of happiness were for me. In fact, I came up with my…
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I Saw the Future - Fable 5
In June of 2026, my son texted me out of nowhere: "97 agents, 9.4 million tokens. 1.5 hours. But I saw the future."
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Having All of the Leverage
Many years ago, I owned a historic building on Main Street in the center of Flemington, New Jersey. The building had an incredible past and, in modern times was home to my wife's gift shop and was…
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Moses with the Tablets
When we built our first internet company, it was 1999 and the web was still new to most enterprises. Companies knew it mattered but had no idea how to use it to drive brand awareness, brand…
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All Gravy Trains Come To An End
Every so often you land a client who pays you a lot for not much — high revenue, low effort, almost no expense. It feels fantastic. Pure gravy.
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Fix The Broken Window First
About 25 years ago, I bought an old building from 1882. It was full of history and sat right in the middle of our town — but it had fallen into disrepair. Broken windows, chipping paint, weeds…
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All Driveway vs. All American
Sometimes I worry that we're playing the game at too low a level — too small. Like we're the best basketball players in the neighborhood, proud to win in our own driveway, when there's a whole…
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What I Learned From "Shark Tank"
One of the greatest challenges for a technology entrepreneur is scaling sales. Even if you have an incredible application, it can take far too much time and money to create awareness and win…
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Confidence Speaks in a Quiet Voice
Real confidence doesn't need to announce itself. The people who are surest of themselves are usually the calmest in the room — they don't oversell, overexplain, or shout.
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Always Make Them Want You
I had a great boss, Brad Smith, who gave me advice I've used ever since: always make them want you.
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The Chicken and The Egg
Every two-sided business starts with a paradox. Uber is the classic example: drivers wouldn't sign up because there were no riders, and riders wouldn't use it because there were no drivers. Each side…
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The Flywheel Effect
One of the most useful ideas I've ever come across is Jim Collins' flywheel — from Good to Great and his follow-up monograph, Turning the Flywheel. Understand it, and you understand how great…
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You Have to be In It to Win It
You can't really understand something transformative by reading about it from a distance. You have to get your hands dirty — be in it.
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Fail Fast, Scale Fast
Most people are slow to quit. They keep pouring time into an idea long after the evidence says it's not working — because stopping feels like losing.
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Leave with Them Standing in the Aisles
One of my early bosses taught me a lesson I've never forgotten: always leave on a high. Run through the finish line. Leave with them standing in the aisles, giving you a standing ovation.
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With Change Comes Opportunity
Some people hate change. They see every shift as a threat — the glass half empty, something being taken away.
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The Burning Platform
I had a boss who used to say you can't move a team without a burning platform. I've preached it ever since. People don't change when standing still feels safe — they change when staying put becomes…
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It's 1995 All Over Again
In 1995, you could feel something enormous beginning. The internet was just arriving, and the possibilities gave me goosebumps. I didn't have it all figured out — nobody did — but it was impossible…
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This Too Shall Pass
For many years big problems would really impact me. I wouldn't be able to sleep because I couldn't get the issue out of my mind.
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Desire What You Have
I spent a lot of time studying how the mind works by reading a lot of books on the topic. One of the things I learned is that most people live in a permanent state of wanting — the next deal, the…
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5, 4, 3, 2, 1 Lift Off!
I was listening to a podcast the other day and someone mentioned that when they wake up in the morning, in order to get fired up to attack the new day, they think of themselves as a rocket and say 5,…
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Pretend You Didn't Get The Message
We had been in business for about a year and I was excited about the day in front of me. I had two prospect calls with senior marketing people in two Fortune 500 companies. It was a beautiful day, I…
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"The Believers" vs "The Non-Believers"
As everyone knows, hiring great people is critical. You are only as good as your team. So, the interview process is incredibly important. In fact, we spend a tremendous amount of time interviewing…
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Get The Biggest, Best and Brag
Early in my career I remember someone saying "Marketing 101 – Get The Biggest, Best and Brag". This meant to do whatever it takes to get the best brand name companies on your client list and brag…
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Just Get Started
Do you want to have your own business? Well, I always did. When I was working at ADP and mentioned my goal to Steven Goldthwaite, an experienced entrepreneur, his advice was to just get started. He…
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Getting Better
If you want to get better at business, you have to work with people who are better at business than you.
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Best Places to Work in America
Our first company was honored as the #1 Best Place to work in New Jersey and one of the 50 Best Places to Work in America. One of the awards was announced before an audience of more than 12,000 at…
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Where's The Elephant?
As everyone knows, depending on how a business is doing, there is typically more pressure on one part of the organization than on other parts (e.g., Sales vs. Operations). If revenues are below plan,…
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From Good to Great
Do you want to create a truly great company? Not just good but great? One of the best?
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Taking a Step Back to the Basics
Old is new again. Just because the book or framework or model is old, it doesn't mean it can't be helpful today. In the late 1980s and early 1990s I was introduced to Michael E. Porter and several of…
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Ensuring Acquisition Success
While working at AT&T earlier in my career, I was fortunate enough to participate on several very strategic projects. Many were code-named projects like "Raptor", "Eagle", "Maple", "Seagull", etc.…
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Yes, But Are You Really Any Good At Selling Vacuum Cleaners?
When you first start a business, getting customers is the biggest challenge. Since you don't have any credibility, it's very hard to convince someone to do business with you. Think about it - you…
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Crawl, Walk, Run
I've been criticized several times for my "Crawl, Walk, Run" approach to running a business. I was told that the best managers have a much more aggressive style. Their approach to business is just…
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Right To Left Thinking
When people tell me about their goals, my first question is always the same: "Great — what exactly do you want to do, and when do you want to do it by?"
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