The 3 Biggest Lessons I Learned From Working in the Family Business

The first time you go into business, you need a good mentor, and there’s no one better than your own family — especially if they’ve done it before.

I learned how to manage employees, how to scale a business, and how to deliver the best possible experience to the consumer — all under the mentorship of family with three generations of business know-how.

There are stereotypes of working in the family business, but in my case I took away huge lessons I’ve applied to my career. My father, Elliott Greenberg, ran a dropshipping business. He applied scalable models and lessons he learned from his father before him, who installed jukeboxes and created an early mail-away coffee service for businesses in the 1950s.

Today, I work in a shared office with my father, and we continue to encourage and challenge each other on a daily basis.

The best thing about being in business with your family is they’ll shoot you straight. They’re more knowledgeable about your strengths and your weaknesses than anybody else. And you know they have your best interests at heart — because your best interests are the family’s best interests.

Here are the biggest lessons I learned while working in the family business:

1. Work outside the family business first

The first thing my father made me do before joining the family business was work somewhere else.

That’s preached by other family businesses too: you always want the children to do something else first. They’re going to gain skills and experience they wouldn’t get internally, and then bring them to the family business, which means growth.

In my case, before joining my dad at his dropshipping company, I had a variety of other jobs. I waited tables, sold telecommunications equipment, and worked in a pool supply store. I was an investment advisor for Chase Bank and later sold insurance — which, as you can guess has been hugely influential, since I now own and operate my own independent insurance company, True Blue Life Insurance.

Later, when I went to work with my father, I had a solid idea of what I could contribute to the family business. I was able to bring new assets to dropshipping because of my outside experience.

More than that, I had the encouragement I needed to apply those skills in a meaningful way.

2. Try new things and learn from failures

My father always encouraged me to try new things within the company.

He let me build a website, market all his products, and expand the business. He treated me like an asset — someone to be invested in when it comes to growth and learning.

Now, at my company, I think of my team members as assets. I let them try new things even if they’re likely to fail.

I try to bring the sense of familial support to my team members as they’re trying things because I know how it feels to grow while supported like that. And I’ve seen how companies can benefit from employees learning and trying new things while working there.

For example, I implicitly trust my customer service team to handle issues in what they think is the best way for the individual. I’ve borrowed from Nordstrom in this arena: “Use good judgement in all things.” This kind of trust frees up my team to come at customer issues from new angles.

As long as you learn from it and become better for it, failure isn’t a huge deal.

At the worst, you know what doesn’t work for your company. At the best, you’ve got a whole new way of doing things. And then you can begin to implement these new techniques in your bigger picture.

3. Build a passive and scalable business

My father believes that vision is more important than money.

What that means is, knowing what you’re going to build in the long run and how you want to affect the future has far more weight than the sales numbers at the end of the day. Basically: have a scalable plan.

My father learned this from his father.

My grandfather, back in the ‘50s, placed jukebox machines in bars and restaurants. He owned a bar, and saw the guy who came in once a week and collected all the money from the jukeboxes. After years of dealing with drunks every night, my grandfather said, “Forget this,” and went into the jukebox business instead.

This later expanded into placing both jukebox machines and coffee makers in local businesses. Then he started shipping them coffee. Now, mind you, this was well before subscription services and Amazon, and here he was, going to his mailbox picking up checks. He was dropshipping — a passive, scalable style of business that allowed him to expand into other products.

And now that’s what my father does — although it’s with janitorial supplies rather than coffee.

So, I learned from my grandfather first-hand about the importance of a roadmap, and a scalable vision — knowing where you’re going so you can always build better. Both my father and I have created businesses with clear and realistic opportunities for growth, and it’s thanks to my grandfather’s inherited wisdom.

Because of what I’ve learned from my family, and what I’ve benefited from in that supportive environment, I try to treat my team members like they’re part of my extended family.

Any good team will think of their coworkers like family. It’s part of what makes them feel encouraged to make risky decisions or mistakes. That safe learning environment helps them to perform better.

Because if you’re family, you know you won’t get left behind.

If you want to learn more about what I do, you can visit True Blue Life Insurance. And for more information about building your business, please visit my personal site to read more from me, including my book, The Salesman Who Doesn’t Sell.