Restaurant Reservations: Returning to the Family Business


In my favorite half-hour comedy, How I Met Your Mother, the characters Lily and Marshall had a series of long-term bets about the future.

“Barney will watch the sex tape.”

“Marshall will go bald.”

“Ted and Robin will end up together.”

This inspired me to keep track of my own bets for certain decisions in my life. I’d record the decision, write down a few sentences about my reasoning, and revisit it a year (or more) later.

For example, should I buy Snap? Will I work in Hollywood again? How far along will VR be in one year?

With most of these bets, I make the decision and move on. I’m curious about them, but the curiosity doesn’t keep me up at night.

Will I return to the restaurant business?

Except… for this one bet that’s been sitting there for a while, and I still don’t know which way it’ll go. It’s been in the back of my mind for the last 2 years.

I’d say that you can make about 95% of decisions quickly,  because in the grand scheme of things, they don’t matter. The remaining 5%… take a bit longer. Clearly, this falls into the latter category.

This post isn’t a neat, orderly “how-to” post with 7 steps for decision making. It’s more of a snapshot of how I’m thinking about the bet right now

Here’s the bet I’m struggling to answer: Will I eventually return to the restaurant business?

To make sense of the bet, I’ll look at it through a series of questions:

  • Why is the bet in play?
  • What’s the desired outcome?
  • What’s stopping me?
  • What are potential solutions?

Why is the bet in play?

It’s been in the periphery for the last two years or so, since I moved from Los Angeles to New York City. In LA, it wasn’t a question. I was working towards being a television writer, living and working 3,000 miles away from the family business. There was no way for me to work with the restaurants — in fact, that had been one of the reasons for going to LA in the first place. I talked it over with my family and we agreed it didn’t make sense.

But since moving back to New York City, distance is no longer an issue. Plus, I’m looking to move back to Albany in the future, and suddenly the definitive “no” has inched worm-like towards “maybe.”

Plus, at the time, it was important for me to get away from the family business. I learned different industries (entertainment, production, marketing, growth, self-help) and different schools of thought. I worked with a range of different operators, some great and some terrible. It’s shaped me into a different person, someone who’s ready for this challenge.

What’s stopping me?

I asked my dad, “When you’re retired, and if you sell off the restaurants, will it be a sad day for you? To sell off these businesses you spent all this time building?

“Nope,” he said.


“They don’t have sentimental value,” he admitted. “They were a means to make a living. We worked hard, they made money. And when I sell I’ll be glad I don’t have to deal with the headaches.”

Maybe it’s the difference in our ages or maybe I’m more romantic than him, but there’s a desire to build on what my dad started, what my whole family got to be a part of, since the beginning.

Don’t get me wrong — I’m pragmatic about it as well. I’m not a chef or a restauranteur. I’m not interested in creating a hip restaurant that follows the trends like “beyond meat” or “sour beer.” Thinking about that literally does nothing for me.

What does interest me?

  • Acquiring and retaining customers
  • The consumer shift from dining in to eating out that’s engulfed major cities
  • The challenge of maintaining a profit margin when Grubhub and UberEats take 30% of your delivery receipts
  • Building a team that can handle the store, then expanding
  • Leveraging those wins into other ventures

Restaurants aren’t the only thing I want to do, but they’ve created opportunities for my family (literally, everyone in my family). So it’s tempting to keep doing it , for the future opportunities it’ll create.

Before I moved to Los Angeles, my Dad tried getting me to stay. He said we could build up the restaurants together. The sentiment was right, but the timing was wrong.

Now, he recommends against going into the restaurant industry. Both my parents do. It’s a hard way to earn a living (more on that later). I think he sees that I already live a great life (I do) and if I switch industries, I’m giving that all up…. for what?

What are the barriers?

Last weekend I visited Albany to view a house. My dad took the day off.

On his day off, he coordinated getting a new fry cook up from Boston: schedule the time, get someone to pick him up from the bus station, and drop him off at the restaurant. At 3pm, after we viewed the house, my dad left to go meet him, and drive him to the shared dormitory for the staff.

That night, after the dinner rush, someone broke one of the knobs on the stove. It started leaking gas. There was no valve that could cut off gas to the stove, so they killed the gas to the entire restaurant and closed early. My dad was on the phone until 10pm trying to get someone over there by 8am the next day, so he could  open for dim sum on time.

The next morning, his manager accidentally ran a red light and got into a car accident. He came over to borrow a car.

All this coordination, he does in English, Cantonese, and Mandarin.

Combine that with keeping up with changing consumer palettes and even faster changes in technology, it’s a lot. It’ll become the only thing you think about. The job is putting out fires, at all hours of the day.

Chinese restaurants have it particularly tough with historically lower margins. There’s the perception you “get it all” when you order Chinese: your main dish, the egg roll, fried rice, soup and a can of soda… for $7.99. The image persists even as we try and shift to a more upscale experience — it’s hard to change perception after over 100 years, when Americans first started eating dishes like Chop Suey.

What are potential solutions?

Tactically, there are a lot of different potential solutions. Here’s an example:

Sell the Chinese restaurant and get into something smaller and more manageable.

A few months back, I took my family to a ramen restaurant in Astoria called Tamashii. While waiting for a table, my dad sized up the place: estimating the square footage, the flow of the customers in and out, and number of staff on the floor and in the back (it was open kitchen). “This place is a gold mine,” he concluded.

“You could open something like this, have 2 people in front, 2 in the back, and it’d do really well, Keep everything simple.”

Ultimately though, all solutions ladder up to two fundamental beliefs that must be in place first:

One, a belief in systems. That systems exist to solve all of these challenges and remove one operator from doing it all himself. A system would ensure that I wouldn’t have to handle the hiring and coordinating of staff on my own. Or when a valve breaks, the staff would know exactly what to do on their own.

Second, the belief you’re capable of building these systems.

If I didn’t believe I could solve the language barrier problem or the hiring challenges, then it would be  a non-starter. It’s easy to look at the situation, say “that’s too hard,” and not try.

It is hard. But it can be done, because other operators have succeeded.

Is it worth sacrificing my current lifestyle for a more difficult one? Maybe not. But no matter what your line of work is, building something great doesn’t lead to an easy life. This is contrary to the insta-rich schemes being peddled at the moment, whether it’s a dropshipping business, becoming an Instagram influencer, selling courses, or trading crypto. I have friends who do well in each — they all work extremely hard.

It’s more a question of trade-offs: Is the work worth it? Do you have the talent and ambition to build something great?

And do you have a powerful enough reason to stick with it, even when it’s hard?

Photo Credit: Thomas Hawk

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