Lessons learned growing up with entrepreneurs

Scott Wolfe Jr
The Startup
Published in
14 min readDec 12, 2019
The Clintons visiting my parents' laundromat & po-boy shop, Melbas, in New Orleans.

My kids played with some gumball machine toys in the middle of a small circus a few weeks ago, and from time to time, were forced to make eye contact and shake hands with Hillary, Chelsea, and Bill Clinton.

Too young to know much about the Clintons or the rarity of spending an intimate hour with a former first family, they were getting many varied and layered lessons that Saturday morning. I know that from experience. In fact, despite turning 39 recently, I’m still learning from my mom and dad.

I had a rush of memories wash over me as I watched my mom discuss her involvement in a children’s literacy program with Hillary and Chelsea. Certainly, this was an exceptional moment, but it merely reminded me of so many other moments, when, at various ages and heights, I looked up to see my parents doing something else remarkable.

From birth, I’ve tagged along on their entrepreneurial journey as a spectator, a participant, a critic, and an admirer. But mostly — because of the lessons received through the ups, downs, twists, and turns — I’ve been and continue to be a student and benefactor.

Here is what I’ve learned.

Overwhelm

You can do something poorly, you can do something well, you can do something great, but if you want to stand out and succeed, then you ought to do something that completely over-delivers and overwhelms.

Growing up, I had a variety of duties at my parents' small grocery stores. Stocking the shelves (better put the labels facing out!), bagging groceries (walk them to the car!), even counting money (make all the heads face up and the same way!).

One of my jobs was wrapping produce, cold cuts, and similar items. After pouring through a box of grapes, sorting them into trays, and wrapping them in plastic, my mom would come over to inspect. She’d turn the trays over and look at the bottom to see whether the plastic melted out smoothly, or clumped together. You had to do the clumpy ones over again.

Walter Isaacson tells a story similar to this in his biography of Steve Jobs. Jobs would reject designs of logic boards inside Apple machines because they were not straight enough. This, of course, despite the fact that the boards were inside the machines and unseen. It seems that Jobs got that trait from his dad. Jobs told Isaacson that his dad, a carpenter, really cared about the quality of his designs and work, even the parts you would not see.

This may all be somewhat neurotic.

It definitely plots somewhere on the neurosis spectrum. At times, focusing on some detail “that you cannot see” falls flat off the spectrum and is squarely neurotic.

But then there are all the other times.

In those times, these things are not “details,” but are instead the markers of doing something so well, and so correctly, and so perfectly, that you overdeliver and overwhelm. And that is how you stand out in anything, and how you succeed in anything.

Chip & Dan Heath have a great study of this in their book, The Power of Moments. When summarizing the key thesis in a video, Dan Heath explains that doing things just right doesn’t “underwhelm or overwhelm, but just whelms.” Heath explains, “if you drive down the stretch of a road with no potholes at all…if your cable tv performs exactly as its supposed to…you’re not ecstatic, you’re just whelmed!”

No one ever remembers being “whelmed.”

And no one remembers being “whelmed.” Ever.

And if you live your life and you do your business by constantly whelming people, then no one will remember or care much. You’ll miss the promotion, you’ll miss the target, you’ll miss the opportunity, you’ll miss, miss, miss. To hit, you must overwhelm.

My parents gave me a great gift in teaching me what overwhelming looks like, how it feels, and surprisingly, how easy it is.

I have a vague memory of being in a car with my dad at one of our stores and sitting the parking lot, looking through the windshield at someone doing some work task. The job wasn’t being done particularly poorly or well; it just wasn’t all the way right. And I remember my dad watching it, telling me, “It’s surprising how easy it is to be successful.”

He was referring to the slight, tiny, minuscule difference between average and great.

When my parents were operating their grocery stores almost every conversation, everywhere — in the parking lots, over dinner, in the office — was suffocated by details. How many windows are enough to get light in? Are the windows, counters, meat cases, cooler doors, clean? Are the price labels straight? The signs the right colors? Does the canopy light up brightly enough at night? And on and on.

When you consume that tiny space between mediocre and great, you begin to overwhelm people. You begin to wow them. And then you’ll get addicted to it and be unable to stop. You’ll notice mediocre everywhere and it will drive you mad. You’ll be neurotic.

And you know what you’ll never be neurotic about? “Strategy.”

Action Eats Strategy For Breakfast

When I was born, my parents were 16 and 18 years old, they put me in a drawer to sleep, and they were briefly on welfare. Over the next 20 years, they traded the proverbial red paperclip for a house, building out a multi-million dollar regional grocery chain with hundreds of employees.

In all of the business conversations I’ve overheard or participated in, I’ve never, ever, ever, heard this word uttered: strategy. I don’t think my parents ever said it, or ever thought about it.

Peter Drucker is famously credited for the quip “Culture eats strategy for breakfast.” Growing up in an entrepreneurial family, this rings absolutely correct. And I would add something else here. That the “culture” must be a culture of action…because, really, action eats strategy for breakfast.

I’ll illustrate with a marketing idea. My parents had an idea to print bumper stickers for their meat markets. They printed red stickers with block white letters reading “YOU CAN’T BEAT WAGNER’S MEAT.”

The slogan for my parents’ grocery chain, Wagner’s. For 15–20 years, billboards & bumper stickers appeared all over the city with these 5 words in simple red & white, creating a compelling regional brand.

At the grocery stores there was always a stack of bumper stickers at the checkout counter. And a sticker would go in almost every bag. And then, the store would give away $100 a week to someone “caught” with the sticker on their car. And they would take pictures of the people getting the $100 and stick those photos on the wall. And so on and so forth.

Before you knew it, “YOU CAN’T BEAT WAGNER’S MEAT” bumper stickers were literally all over New Orleans. It was overwhelming. Even a touch controversial.

No one sat down and wrote out a marketing strategy for this. They just did it, and kept doing it, and pushed it, and kept pushing it, and poured bumper sticker activity on top of bumper sticker activity. Sure, if you’re the CEO of Oracle, you may need to think a little bit about strategy and make big investment/ROI decisions. There is some macro stuff involved there.

But for the rest of us? So much is just activity.

That’s why the Clintons came through my parent’s laundromat last weekend. There was no “strategy” to get them there. My mom just had an idea about giving away books, getting authors involved, and utilizing the space to drum up literacy (more on that later, in the “double bottom line” section). And then she just started with activity. Emailing people. Emailing more people. Using one success to “trade up the chain” (credit Ryan Holiday) to get another success.

And then out pops the Clintons. Or the bumper stickers. Or whatever else.

Be Enthusiastic

My parents put together a video for my high school graduation. It included some interviews from aunts, uncles, grandparents, and, of course, my parents. I watched it recently after my kids got their hands on it, and at the end, in my mom’s interview, she advises, “Don’t lose your enthusiasm. People follow enthusiasm.”

It’s interesting that my mom would cough up this advice in that video because it isn’t anything she told me before, or ever since. And it isn’t something you really teach to someone. You don’t teach a kid, an employee, an athlete — anyone — to have enthusiasm.

Yet, I learned it.

It’s safe to say that my dad wasn’t jumping out of his crib looking to run grocery stores. No one jumps out of their crib anxious to run a grocery store. Or to work at one. Or to work at a tech company. Or to do anything really. Even some professional athletes — literally living out their childhood dreams — struggle to maintain their enthusiasm for the “game.”

A few months ago, I wrote about this in “Career Advice You’ll Love or Hate; Your Choice,” as I tried to explain (to myself?) where “passion” came from. I quoted Michelangelo, who once remarked that “[i]f people knew how hard I worked to achieve my mastery, it wouldn’t seem so wonderful after all.” And I concluded on the point with this:

Passions are developed. Novelty is in the nuance. Careers aren’t planned. And curiosity, that little thing that leads you to more and more knowledge, and eventually, a deep understanding of something, is hard, grueling, and sometimes miserable work.

No one is enthusiastic about grocery stores out of the crib. No one is enthusiastic about anything out of the crib. But, out of the crib, everyone is enthusiastic about one thing: learning and getting better. My parents never lost that.

Learn

Pregnant and quickly married, my parents dropped out of high school, got GEDs, and then got on with their working life. Much later, my mom returned to finish school and ultimately scored a masters degree from Harvard(!), but until then, the formal education I got was far, far, far beyond their formal education.

Learning and education, though, are unrelated.

On family vacations, my mom and dad would stop at every meaningful grocery or convenience store around. We’d go and walk around the place for 30–40 minutes (kids love that!), and my parents would take photos, talk with the staff, and learn, learn, learn. I’d go to convenience store conferences with them and spend hours going through the exhibitor tables and learn, learn, learn. We didn’t have coffee table books, but instead, we had stacks of trade magazines and business books. Information. Was. Everywhere.

I just completed a nice biography of legendary Patriots coach, Bill Belichick, and the author talks about Belichick’s thirst for learning on a number of occasions; all of which reminded me of my parents:

Over the years, Belichick had proven he would go anywhere and talk to anyone who could lead him to the team-centric players he craved. While he was still in Cleveland, Belichick visited with Jerry West, the great Los Angeles Lakers executive and former player. West said Belichick asked him about managing a salary cap, and about the Lakers’ draft philosophy and how that might apply to what a football coach was searching for in the college game…Belichick visited Saban at LSU. He developed a friendship with Jimmy Johnson, who coached the Miami Hurricanes, the Cowboys, and the Dolphins…Belichick wasn’t only the best coach in the NFL; he was the best listener and brain-picker, too.

Belichick would later visit with New York Yankees GM Brian Cashman and manager Joe Torre to find out everything he could about how they prepared their players during the dynasty years. Cashman wanted to pick Belichick’s brain, too, but the football coach asked so many questions about their baseball approach that it remained a one-way conversation — just the way. Belichick always preferred it.

Something important to understand about all this “Brain-picking” is that it’s not about finding someone who has a solution, recipe, or instruction for you. Going to an “expert” for an answer is a bad idea. As explored in Chip & Dan Heath’s great book on decision-making, Decisive, experts are pretty awful at making predictions or giving you advice about what to do.

Instead, what you are seeking from experts and from “brain-picking” is information. You just want to learn more about something, and then, based on all the information you know, to forge your own path.

My parents never had a formal education, but they had curiosity, and they were always learning. And they taught me how to learn. And they taught me that, ultimately, the person with the answer is me.

Lose

After buying and operating small neighborhood grocery stores for almost ten years, I remember the day my parents opened the first store they built from the ground-up. It was my birthday. I skipped school and went out to the grand opening. It all went great. That location would go on to be one of their most successful until the day it washed away (Katrina).

I remember the day my parents opened their second store, too. I got to skip school and go to the grand opening. The mayor was there. The ribbon cut was fun. That one tanked.

Opening day for new grocery store on Feret Street that didn’t do so well.

I was too young to really understand the whole thing, but would overhear the worry and stress in conversations at home. And candidly, while my parents eventually climbed out of this challenge, I don’t know much about how they did it, what the challenges were specifically, and what lessons were learned. I just know that they lost here.

My memory is better about other failures. Alongside the business, my dad experimented with politics, too. He jumped into a local council election when I was about 12, disrupted some old hangers-on, and won in a landslide. Almost 10 years later, he threw his hat in the ring for Parish President of the city (which is like Mayor), got into a dirty, slugfest, and lost by a healthy margin.

Being something like 20 years old at the time, I remember that election well, and especially election night. The party quickly turned somber, the crowd evaporated, and the night was suddenly done. Our family alone and heading to bed almost like any normal night.

It was a tough election — and not just the result. The entire election was tough and my dad had been through a lot. I remember asking him that night something about whether it was all worth it, and he gave a reflective answer about how it was worth it because he was “in the arena,” so to speak. The thrill of victory and agony of defeat thing.

Through the years, my parents had store locations that went fantastically, and others that suffered. They won elections, and they lost elections. They got into legal and regulatory battles with New Orleans’s City Hall. They have trophies and battle scars. The losses were so commonplace that I’m forgetting to even mention the time they lost it all. Literally, all of it, when Hurricane Katrina flooded the city, all of their store locations save one, and flipped life upside down.

In the first 30 years of my life, I had front row seats to a lot of wins, a lot of fights, a lot of success…and a lot of hard, cold, disheartening loss.

But I learned that losing isn’t actually losing. It’s just part of winning.

Love

My parents fell in love with a few things — they loved their customers and they loved their employees. This had to be the case, because it consumed almost all of their waking thoughts. The dinner table conversation was never about profit margins, COGS, revenue growth, marketing budgets, or anything like that. The conversations were exclusively about how to make things better for their employees and their customers.

The grocery business is, of course, a service business. But this is too easily forgotten when you emphasize “business” instead of “service.” I learned to emphasize the “service,” and I think, that’s because my parents started with love.

The family’s grocery stores were scattered throughout New Orleans’ inner-city. It would grow to hundreds of employees, thousands of daily customers, and more than a hundred thousand daily passers-by. There was a lot of emphasis on this community and how to serve them.

First, there were really simple and practical things. Many of these neighborhoods did not have nice things. The grocery store status quo was small, dark, cluttered, grimy, and apathetic. My dad emphasized that their stores be clean, have lots of windows, modern design, good lighting inside and out, etc. It was really like walking into a Whole Foods quality facility in some of the city’s poorest neighborhoods. Not many people invested in facilities like this in places like this…even now. My parent’s choices here made good business sense, but it was the way they got to that “good sense” that stuck with me. They didn’t make these decisions because of a McKinsey report. They came to those decisions because they cared.

Second, there were a bunch of more nuanced things that really get lost in the weeds of their success.

There was an advertising “reader board” at the front of a store. My mom wrestled control from my dad, and instead of promoting 2-liters and leg quarters, she rotated inspirational quotes. This eventually became a calling card throughout the city with their reader boards getting hundreds of thousands of views every day in a time before the Internet, social media, and email; and delivering important-but-not-often-delivered messages to their communities. They would give away ice cream to kids who brought in report cards with A’s. Even the recent Clinton visit is connected to these projects. It’s part of a literacy program that my mom spun up at their po-boy shop and laundromat. A literacy program. At a po-boy shop.

A recent book signing at Melba’s with Sybil Haydel Morial and her “Witness to Change.”

There are tens or hundreds of other examples to go on. My parents started with love in how they thought about their business, and their communities. It impacted the communities they were in, the customers they served, and definitely, the people they employed. I’m 40 years old, and I can walk into my parent’s po-boy shop and eat the same macaroni and cheese that I had when I was 6, hugging someone who has been working with my parents ever since then. I think something like 15% — 20% of the employees at their po-boy shop, Melba’s, worked for my parents during their grocery store days. This in an industry with extreme turn-over rates, and in a community that not only lacks normal stability, but has also been torn apart by Hurricane Katrina.

My parents didn’t go into their businesses with a “care” thesis. They just cared. That’s how they started and how they got to the right answers. And they taught me to find the right answers by always starting with love.

Believe

One of the greatest gifts my parents gave me is the belief that I could just go out and do whatever I wanted. I now realize it’s a little strange, but I never looked for a “job,” or thought about getting a job, or really ever had a “job.” Looking for a job is really foreign to me, and I don’t know how to do it.

I can’t quite put my finger on this one because they never sat me down and explained: “believe in yourself, Scotty.” My parents just did what they did and were never overheard pondering whether they could. They just believed, I guess. And, luckily, so do I.

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Scott Wolfe Jr
The Startup

Co-Founder of ClaimSpot.com. Board Director, Advisor, Helper. Former CEO/Founder of Levelset (Acquired by PCOR, $500M).