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Starting an Encore Business? Chat with a Few Smart Millennials First

By Donna Kastner June 12, 2022 Managing Money

Human beings are naturally hard-wired to favor encounters and exchanges with like-minded people.

This website is proof positive of that inclination and it makes sense. Who else but another 60-something might grasp all (or most) of life’s intricacies than someone walking the very same journey?

But for new business start-ups, especially those launched in today’s change-charged business environment, a healthy dose of innovation and new perspective-taking is needed to ensure a prosperous future.

And today’s most successful entrepreneurs tend to take a different path to idea discovery.

Innovators Network Differently

Authors Jeffrey Dyer, Hal Gregersen and Clayton Christensen engaged in a six-year study of the world’s most successful innovators before writing their book, The Innovators DNA: Mastering the Five Skills of Disruptive Innovators.

While all five skills they call out (associating, questioning, observing, networking, and experimenting) are important, I’d like to focus on networking.

Through their research, these three authors learned that innovators network to discover something new and surprising – something they’re less apt to find in conversations with like-minded people. They network with people who are looking at a situation through a new and different lens.

Truth be told, many are also road-testing a few half-baked ideas to better understand how they’re viewed by others not like them and what additional refinements might be needed to get these ideas to the finish line.

My Millennial Discovery Moment

Several months ago, I received an invitation to be a guest lecturer for a data analytics class at a local university. This class was chock-full of Millennials who would pore over data to assess the financial health for a wide range of businesses and organizations. Given the start-up nature of my business, the professor thought this class might enjoying digging into my business plan and cross-checking it with their data.

Without burdening you with too many details, suffice it to say that I’m one-year deep into boot-strapping a business start-up that’s not projected to generate revenue until a year from now. To make things a bit more challenging, I’m managing a full-time consultant practice, while starting up another business that serves a micro-niche segment of the Baby Boomer generation.

With 50 minutes on the clock and 25 students eager to help, we started with a quick scan of data I had collected and analyzed. This included: target Market Demographics (age, location, income, education, etc.), target Market Psychographics (values, goals and objectives, habits, hobbies, etc.), and digital insights (website traffic, podcast downloads, social media activity, etc.).

Starting with roughly 75 million Boomers in the United States, I continued to add filters to winnow this market down further. These filters included age, annual income, education, geographic location, and retirement readiness. With all filters applied, we landed on a more manageable five million or so potential customers.

Going into that class, I felt like I had a good handle on things. I certainly didn’t know everything, but felt confident about the insights gleaned so far. That is, until these Millennials started probing my plan.

These students asked plenty of smart questions and even challenged a few assumptions. Our discussion and debate revealed a few blind spots in my business strategy. There was one blind spot that if left unchecked, could slow down growth for this still fragile start-up. That single hour of discussion produced more value than I imagined and I was grateful.

By the way, in today’s contentious culture where differing views tend to result in stalemates and arguments, it was refreshing to encounter students who could challenge someone older, yet do so respectfully. Let’s hope these students represent what we can expect from tomorrow’s leaders.

A Closer Look at Knowing

There’s a model I’ve embraced as I build out my business plan that might be helpful as you launch your own encore business. It’s called The Four Boxes of Knowing (hat tip to Skip Walter).

  • What You Know
  • What You Know That’s Wrong
  • What You Don’t Know
  • What You Don’t Know You Don’t Know

Each box holds valuable insights that will help you ramp up your encore business faster, but make sure you’re collecting feedback from a diverse set of experts – a wider and richer swath that’s intergenerational.

You might start by chatting with a few smart Millennials. It’s a step I almost missed, because I didn’t know what I didn’t know.

Are you thinking about starting an encore business? If you are starting a new business, who have you reached out to for feedback and advice? What kind of new business would you consider starting in your 60s? Please join the conversation.

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The Author

Donna Kastner is founder of Retirepreneur, a collaborative community for professionals in their 50s and 60s, striving for a smooth segue from full-time job to part-time consulting practice. Through articles, videos, podcasts and workshops, Donna’s ushering in new conversations about blending work and retirement. You can visit her website here http://retirepreneur.com, or find her on Facebook and Twitter.

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