My Dad, an original gangster of entrepreneurship

Omni Talk (click to subscribe) guest contributor and omnichannel expert Anne Mezzenga shares the poignant lessons she has learned from her father and how they inspire her to keep forging ahead as an entrepreneur.

Before Zuckerberg created Facebook and before “start-up” was something you mainly did to a lawn mower, there existed a thriving world of entrepreneurs well below our radar screens. These entrepreneurs did not work in Silicon Valley offices with massage rooms and kitchens full of organic persimmons. No, they were everyday people that worked in every neighborhood and in every town across our great country. They were and still are affectionately known as small business owners.

I am the daughter of two small business owners, and they both made it look so easy. As I’ve been forging ahead as a (relatively) young retail entrepreneur, I feel like I’ve been on a rollercoaster ride. And not a fancy schmancy Six Flags roller coaster ride either. I’m talking about an old janky wooden ride that clanks and shakes, and in which you put your survival in the hands of a carny at the bottom of the ride who may or may not be high on methamphetamines..

As with any carny’s drug addiction and any janky roller coaster, entrepreneurship offers high highs and low lows, along with the uneasy feeling of a complete free fall every so often. You don’t know when it’ll all be over or how you’ll come out after you land. But what I find interesting, and what inspires me to write this piece, is that none of what I bring up about this “start-up entrepreneur” lifestyle is at all surprising to my Dad whenever he asks me, “So, Annie, how is that ‘business’ of yours coming along?”


Because my Dad was a start-up entrepreneur before it was cool. My Dad was the OG of small business entrepreneurs, as in “Original Gangster” for all you non-hip hop fans out there.

My Dad started his career at 17-years-old by building his first house, and now, at 60-years-old, he’s created quite a successful building company. But you won’t see a feature on him in Fast Company or Entrepreneur magazine. No, for him, another Friday just means trying to figure out a way to get a small town city planner on board for his next project.

Although his industry is housing and real estate development, his industry is not that dissimilar from my business — retail. Retail has tons of local store owners, who, like my Dad, are also OG entrepreneurs. And those small mom-and-pop retailers that are still around to tell their tales, well, I’d say they, same as Dad, have a thing or two they could teach the next generation of entrepreneurs and start-ups.

So that’s exactly what I wanted to find out. I put a plate of bacon and eggs in front of my Dad, and I just listened and took notes on everything he had to say.

So fresh from the OG, here is my Dad’s advice on entrepreneurship:

Technology Creates New Business Opportunities

When I asked my Dad what he thought about the successful start-ups of the world and what was different for him starting his business 40 years ago versus today, he doesn’t hesitate in answering with a resounding, “The Internet.”  

Dad didn’t have YouTube to showcase his company’s ethos video about the housing development he built from a dream, a small business loan, and a handshake with a farmer for some land:

“We didn’t have the opportunity to scale business at the rate they can today. There was no potential to have worldwide customers. You could only build as many houses as there was demand for in the area you lived. Most of what I do is done manually so I could only build as much as I’m physically able, and as my subcontractors are able to. Now, if I wanted to, I could have a paid subscription channel on YouTube that produced videos showing people how to fix things they’d typically hire a contractor for. Suddenly I can have clients that are all over the world, not just people wanting to build houses in Minneapolis.” (Dad)

(BTW, props to my Dad on this one. How many parents out there have a knowledge of paid subscription channels on YouTube?)

This example was and, in some instances, is still true for small business retailers as well. They had to rely on things like good weather and drafting off of foot traffic from other community events, all the while being constrained by how much product they could physically hold within the four walls of their main street storefronts. They were reliant on customers who lived within a 10-mile radius of their shops; now their customers can shop their stores from thousands of miles away!

The capabilities that e-commerce introduces require some shifts in how the local shop has to think about their operations. They now need to think hard about how the experience of walking through their shop door on a side street in Brooklyn for a city dweller compares to that of a twenty-something in Kansas City shopping from her laptop. They have to ensure the brand experience is the same and as frictionless in the physical as it is in the digital.

The success of their small businesses now hinges on their abilities to adapt to these changes and to leverage technology to expand their traditionally “physical” businesses into an omnichannel world.

Word-of-Mouth is Paramount.

My Dad describes advertising before the internet as:

“Everything was managed by word of mouth. We didn’t have the internet to get more exposure or to expand our business.” (Dad)

So what he did and what most retail small business owners did so brilliantly was provide experiences for their clients that no one else could duplicate — special experiences that would lead their customers to tell two friends, who in turn would tell their two friends, and so on and so on.

Paying attention to the small details that anticipate and serve the needs of customers, whether in the form of building a laundry room on the same floor as the kids’ rooms  or reaching out with a phone call to a spouse of a customer in advance of an anniversary to select a gift that his or her wife has been eyeing while in the shop is what generates word of mouth.

This level of service and attention to detail holds value for customers and helps to determine the businesses they’ll shop and continue to support.

Build the Right Team.

You can’t always be working, although it feels like that happens all too often, so it’s imperative to find people who can run the business in your absence with the same vigor and heart as you would. This also means treating (and paying) your employees well.

Start-up companies and entrepreneurs are often in a state of flux, not always knowing when the next round of work will come in, or whether customers will shop when the buyers have anticipated they will. But modeling business around trying to bridge the gap for employees creates a trust and a loyalty that ensures they will do their best work and maintain a high standard for the business.

This concept is especially true, as both the retail and the housing industries face a shortage of qualified workers.

“The people I have working for me have worked for me for a long time, and know they’ll get paid and that they’ll probably have consistent work during slower times. Because I have good relationships with my subs, and they know they can depend on me, I have an easier time than a lot of builders out there trying to move projects along.”  (Dad)

Having a stable of qualified, loyal employees may not guarantee success, but it will help to maintain business as a start-up through the best and worst of times.

Relationships Matter

“One of the best things to do is to develop relationships that will help you weather the various ‘off-seasons’ that a start-up effort will throw your way,” Dad tells me.

For my Dad, this means maintaining good relationships with his best customers by establishing trust. Sometimes this means staying at their houses until 2AM to finish putting plate covers on outlets and handles on drawers in time for their kid’s grad party the next day. But it also means smaller smaller gestures too. I remember as a kid over the holidays driving around town as he hand delivered tins of cashews to thank the people he’d done work for that past year. It’s these kinds of things that keep his customers coming back to him year after year. Right now he’s working on his fifth project with the same family whose first house I remember him working on back when I was in grade school.

The same principle applies to start-up retailers. Start-up retailers rely on strong relationships with their customers. Start-up retailers strive to design store experiences that foster and deepen their relationships with their customers over time because, in today’s e-commerce world, it is imperative that they anticipate their customers’ wants in order to keep them coming back again and again.

Long-term love of their unique brand experiences is what gets start-up retailers through the tough times. Even if sales are down, strong branded start-ups can rely on their loyal customers to see them through the doldrums, just like my father’s most loyal customers see him through the down periods with small “house projects.” The integrity of start-up business owners and the priority they put into their relationships with customers give them the flexibility they need to weather the tough times.

While the above lessons originate simply from some fatherly advice over scrambled eggs and bacon at a local coffee shop — they are no less mighty.

They test the entrepreneur’s endurance, regardless of his or her chosen industry. Internalizing them can be the difference between success and failure. They help us to “play the game” as my Dad would say, so that even when the times are tough, when the highs are high and the lows are low, we will gladly hand over another ticket to the meth-addicted carny to ride the roller coaster again.



Chris Walton is an accomplished Senior Executive with nearly 20 years of success within the retail and retail technology industries. He is well-versed in merchandising, store operations, inventory management, product design, forecasting, e-commerce, pricing and promotions, and tech product development.

Chris was most recently a Vice President with Target, where he led the retailer’s Store of the Future project and also ran the Target’s home furnishing division for e-commerce. He previously worked for GAP, Inc., as a Distribution Analyst and Manager.

Chris holds a BA in Economics and History from Stanford University, and a MBA from Harvard Business School.

He likes to dress as Darth Vader for Halloween, and his wife also frequently asks him to ask Alexa, "to turn off the music."

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