I am going to refer a lot in this article about “family businesses”, where struggles can happen with multi-generations of family members presently active in the business but the ideas and suggestions on how you can fix it will coordinate with any business.

Why GaryVee is wrong about family business

I’m assuming most people know who Gary Vaynerchuk is but in case you don’t, Gary is a famous entrepreneur, speaker, and business investor.

Gary jumped started his carrier by joining his father’s liquor store and by using digital marketing and Youtube, and turned a 3 million dollar company to a 60 million dollar company in a short time frame.

I recently listened to his podcast which was a recording from a past keynote speech. In the end, Gary received this question from the audience:

“Gary, how do I get buy-in from my father/mother who owns our company that social media and branding are important and will help take our business into the future”

Gary responded with, well you have two options in a family business.

  • Shut up and wait your turn because your Daddy or Mommy built a great business and why should they change to make you happy
  • Ask them every day until they get so annoyed they give in.

Here is where he is wrong, and while I don’t disagree with those two options, there is a 3rd and most important one that he is missing.

“Just do it”

Follow the advice of ask for forgiveness, not permission.

Now I have followed GaryVee for a while and I can almost guarantee he didn’t follow his advice from above and he grew the company by implementing what he thought was going to work. Not by sitting there waiting for his Dad’s permission. He put in the work and made it happen.

The Typical Family Insurance Agency

For those that don’t know I am part of a 3rd generation insurance agency in New York. My Grandfather started it and was sold to my father and uncle until I arrived in 2006.

Joining any family business is difficult but joining a legacy multigenerational insurance agency is even harder. And since this audience is mostly insurance professionals, you will have a deeper understanding of what I am talking about.

The insurance industry as a whole has been fighting from behind for decades when it comes to innovation, technology, and adaptation. We have consistently been a reactive industry, waiting until we have to make changes rather than pushing for change.

The agency owners of the past were not like today’s modern-day Seth Zaremba, they were comfortable and content.

Why is that?

Because business has always been good. For generations, agency owners have made extremely comfortable livings with low stress and more hours logged on the golf course or in the fishing boat than most retired people.

So, what can you do as the incoming generation, the young hotshot producer, the future owner of your family, or (any family) agency?

Eliminate Fear

The number one thing you need to do is to eliminate the fears of the ownership. Older generation agency owners do not like taking risks especially if they are comfortable.

If they don’t see the need or they don’t have the desire to adjust or change they aren’t going to.

Each agency owner’s fears might be different so make sure you assess your situation first.

Here are my top 3 fears that seasoned agency owners might have:

  1. Afraid of the costs
  2. Afraid of change
  3. Afraid of failure

Afraid of the cost

Whether this is a personality trait or generational one, many seasoned business owners don’t adjust well to the increased costs of running a business. Add on the fact they might not see the need or understand what you are trying to accomplish only fuels this push back.

Whether it is investing in the technology to drive change or the simple price increase to the everyday products, increased business expenses cause frustration to the older agency owner.

Why is this and how you solve this problem.

Remember that agency owner that is spending his time on the golf course or out of the office?

Yea, that is who I am talking about because no matter how much money they have or how comfortable their lifestyle is, making changes that can negatively affect that lifestyle is not worth any positive change that could arise from it.

The insurance industry allows us to make as much money as we possibly can but most do not use that as their driving force to work hard, and I don’t blame them.

So how do you as the up and comer handle this?

Easy, invest your own money. You want technology to improve the way you do business, then do it.

Stop expecting or waiting for someone else to pay for things you want. When it works out for you and the business, the owner will see it. They will see the change and how it has made them more money without costing them anything. This opens up the conversation to other future ideas because you have the data

“Stop expecting or waiting for someone else to pay for things you want. When it works out for you and the business, the owner will see it. They will see the change and how it has made them more money without costing them anything.”

Mike Crowley

Afraid of Change

Do you know what will make a seasoned agency owner happier than saving money?

Not having to learn how to use some new tools or technology for it to work.

Using the scenario we just discussed, adding the fact that the owner/family member did not have to invest any money but also didn’t have to learn or change “their ways” is a Win/Win.

This will open up the opportunity to continue to push down the road of change.

Afraid of Failure

Insurance professionals have been afraid of failure for generations, that is nothing new.

You see it even today when insurance superstars like Ryan Hanley talked about how video marketing changed the game in 2011 and how sales professionals can copy what he did to drive new business sales.

Still, it took like 9 years before anyone copied what he did an accomplished it. (Shoutout to Ryan for the push and also Chris Greene for continuing through and not stopping)

Why did it take so long? Everyone was afraid to fail, afraid to step out of their comfort zone.

I purposely put these 3 fears in this order for this reason. Because in most situations it is going to be a combination of all of them.

Figuring out what your family members or current agency owner’s fears are is going to be crucial in putting the steps together to make real change in your agency.

Don’t wait for it to change

I am not sure what your situation is, but if you are still reading this article there is a good chance you either have been part of a family agency, been in this situation before or currently are.

The biggest advice I can give anyone that might be sitting in this situation, frustrated with the way the lack of change and progression their agency or business is making. Is to be patient.

Change is not going to happen overnight and the harder you push the more push back you will get. Remember who are you to push them to make a change when they are comfortable. Put your money (both actual money and time) where your mouth is.

Make it happen, make the changes, and it will work out for you in the end.

It is those family businesses where the younger generation thinks they should be handed everything that quickly fails.

If there is anything I can do for you or you need a sounding board to run ideas on, feel free to reach out to me. My contact information including social media links are on our website,

“Make it happen, make the changes, and it will work out for you in the end.”

Mike Crowley

Mike Crowley

Mike's the third generation agency owner of Crowley Insurance in Syracuse NY. He joined his family business in 2006 after graduating college and has changed the mindset of his traditional home town family agency to one of the most advanced small independent agencies in New York. In 2018, he won IAOA's Innovation award and was on the cover of IA Magazine. Mike was born for the insurance industry and has a passion of helping others. He just recently finished a 4 year term as President of the Big I Local CNY Association. When not working, he loves spending time with his wife, Kim and two kids, Emma & Jack.


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