Next Avenue: How I’m teaching my grandsons to be entrepreneurs


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Gen Z digital natives have grown up comfortable in a world of technology, but they can also benefit from wisdom that comes from experience. Combining the expertise of Gen Z and boomer generations could be a new formula for a startup business to succeed. At least that’s what I’m finding in my own multigenerational experiment in entrepreneurship.

I’m a Woodside, Calif. boomer grandfather with two grandsons, 14 and 12, who’ve brought our combined skills to a novel collaboration. “Duckie” (me) provided the seed money to Gus and Milo Hamilton of Lake Forest Park, Wash. (them) so they could learn ways to digitally promote a new book I wrote about boomers transitioning to retirement. It’s been a win-win collaboration.

3 circumstances leading to our partnership

Three circumstances set the stage for this opportunity.

First, COVID-19 social distancing was causing our excellent grandfather/grandsons relationship to run the risk of being “Zoomed out.” The three of us were not willing to let that relationship erode.

Second, both of my grandsons were showing early signs of entrepreneurship. I thought that reinforcing this through new activities at a higher level of sophistication could add to their skills and confidence.

Third, my book “Shifting Gears; 50 Baby Boomers Share Their Meaningful Journeys in Retirement” needed a promotion boost. The book started strong, but I felt it needed new strategies to continue the progress and that digital marketing (such as placing Amazon ads) could be worth exploring.  

Also see: We owe it to our grandchildren: 2 ways to make a difference

Optimizing digital ad campaign outcomes within the complex algorithms has a steep learning curve, I knew, but I also felt that my grandsons had a natural affinity for this sort of activity.

The plan and the test

So, with input from their parents, I provided Milo and Gus with a Christmas gift: seed funding of $100 each to set up a book marketing business. They’d run their startup and would get a piece of the action based on their results. They’d get paid periodically based on consumer traffic generated by their ads as they learned the ins and out of the complex algorithms. 

Christmas morning was the first test. Would my grandsons understand the idea? Would they be interested? Would they be willing to give it a try?

I enlisted their grandmother and parents to help produce the best pitch to recruit the new presidents, developing a compelling visual presentation. (Recruiting top talent to a startup is always a critical factor for success, but this effort, I must say, was extraordinary.)

A series of envelopes had captivating visual hints about what was to come.

The presentation had the initial enticement and curiosity builder of giving them the title of president of their first startup. As each envelope was opened, another hint built the suspense, using pictures to show the elements of a new venture:

  1. Taking a gamble
  2. Having a bright idea
  3. Being on target
  4. Using digital marketing
  5. Developing new skills
  6. Measuring the sweetness of success
Brainstorming the business

Once their curiosity had been piqued, we had an initial brainstorming of the book promotion business, emphasizing the autonomy they’d have. By the end of the discussion, Gus and Milo were mesmerized and anxious to get started. We scheduled weekly update calls for us all to learn new skills, build the business and measure our progress.

Gus and Milo began their work using a multiple-choice format. In their first campaign, they had existing ad copy from which they picked their preferred ad. They set initial budgets of $2 a day to figure out what works.

And they planned to use the principle of trial and error to optimize results: Try a promotional strategy; if it succeeds, build on it; and if it doesn’t, kill it quickly.

After their initial learning curve and continuing progress on four campaigns, two new projects are now under way. Each president is developing an ad campaign for the book as a gift — one for Mother’s Day, one for Father’s Day.

While they are bringing these gift campaign to launch stage, Milo and Gus are already looking ahead to a campaign promoting an upcoming audiobook.

Related: How entrepreneurs can raise money for a new business—and the advantages if you’re over 50

How it’s been going

So, how are they (and I) doing in the third month of this operation?

Both boys have already generated over $200 for their share of the profits, exceeding all our expectations. Measures of sales, advertising cost of sales and profits to the participants have set new records in the latest month.

Also on MarketWatch: What to do when you don’t like your grandchildren

For me, the project has been a delight. The renewed connection to my grandsons is the highlight.

And here’s my grandsons’ view on the collaboration:

President Milo: “I feel like it’s pretty mind-blowing as I got a Christmas gift to create a mini startup company. If something doesn’t work, then you fix it, using problem-solving steps.”

President Gus: “I think it’s cool because I feel like this is the future of how things are going to work. Everything is going to go online, and it’s important to know how to do this now instead of learning later.”

So far, I’d say the experiment is a huge success: Each generation has brought their own skills to the business, learning from each other to build impressive results. But the biggest payoff has been the building of the generational bridge between Gen Z grandsons and this boomer grandparent.

Richard Haiduck is author of “Shifting Gears: 50 Baby Boomers Share Their Journeys in Retirement.” 

This article is part of “America’s Entrepreneurs,” a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur and Innovation Exchange. This article is reprinted by permission from, © 2021 Twin Cities Public Television, Inc. All rights reserved.

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