Reinvent Yourself and Find Your People (By Friday)

Editor’s Note from MILF & Silver Fox (Nick and Liz to finesse)

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Elizabeth (MILF): Personal story. I keep calling my employees my kids names and my kids my employees names…

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Nick (The Silver Fox): . It’s ok if you have more side hustles than google tabs open in your browser.

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Here’s the thing about starting a business in midlife: you’ve got all this wisdom and absolutely zero clue how to slide into anyone’s DMs professionally. You know your stuff. You just can’t find the people who need to know that you know your stuff. It’s like being the world’s best-kept secret, except you’re tired of keeping secrets and you’ve got orthodontist bills to pay.

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This week, we’re talking about finding your people without losing your mind (or what’s left of it).

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— MILF & Silver Fox

Midlife Crisis? More Like Midlife Calling

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Let’s address the elephant in the room wearing reading glasses and sensible shoes. 

You didn’t wake up one Tuesday and decide to start a business because you were “bored.” You woke up because your kid’s college portal just dropped a tuition bomb, your dad’s medical bills rival your mortgage, and your 401(k) just laughed out loud.  So, we are partnering with the small business funding platform Hello Alice to help you find funding and resources. 

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The average successful entrepreneur? 45 years old.

(MIT Sloan.)

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Entrepreneurs in their 40s are twice as likely to succeed as those in their 20s. Why? Because we actually know things,like how to fix the Wi-Fi, mediate sibling fights, and file for an EIN number without crying.

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And fellas, this one’s for you too. While women often lead the caregiving conversation, more men are now in the sandwich mix—balancing parents, kids, and careers with equal parts pride and exhaustion. For many, starting something new isn’t about escaping responsibility; it’s about finding purpose again in the middle of it all. The second season isn’t a midlife crisis—it’s a recalibration. A reminder that you’ve still got ideas, drive, and something meaningful left to build. Midlife isn’t winding down; it’s warming up. Just… with more ibuprofen.

Your Market Is Out There (Probably Googling the Same Thing at 2 A.M.)

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The beautiful mess of midlife entrepreneurship?

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Your ideal customer is probably another exhausted legend who needs exactly what you’re selling. They’re out there, half-asleep, scrolling with one eye open, whispering, “please let this fix my chaos.”

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Your potential audience might be:

• Other sandwich generation survivors who get the grind
  
  
• Caregivers juggling parents, partners, and post-it notes
  
  
• Parents managing the wild jungle of teens and tweens
  
  
• Anyone who’s ever sincerely Googled “how to adult”
  
  
• Fellow midlifers craving a sense of purpose (and a nap)
  
  

We succeed in midlife because we get real problems. (World Economic Forum.)

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Market Research That Won’t Make You Want to Nap

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Traditional market research feels like doing taxes while your mother-in-law critiques your form. Skip that. Start with your own chaos.

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Ask: what problem did you solve in your life that made you think, “Other people need this”?

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Then do this:

• Lurk in Facebook groups (listen first, sell never)
  
  
• Read Amazon reviews for similar products
  
  
• Scroll Reddit—just… not too deep
  
  
• Pay attention to what your friends complain about after two glasses of wine
  
  

Voilà. Market research, midlife style.

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Market Fit: When Your Thing Meets Their Need (Without the Awkward Small Talk)

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Market fit is basically dating for businesses. You’re looking for that “where have you been all my life?” moment between what you offer and what people want.

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According to Forbes, entrepreneurs over 40 are better at reading people and situations. Translation: you’ve been around long enough to know when someone’s lying about “circling back.”

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Speaking Their Language (Not Corporate Buzzword Bingo)

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Your people don’t want to be onboarded into your ecosystem. They just want to know if your thing will make Tuesday suck less.

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Talk like a person. Write like a friend. Sell like someone who’s been there. Because you have. See how entrepreneurs tell their story on Elizabeth Gore’s podcast - The Big Idea on Yahoo Finance. 

(“Authentic communication” Yes Your Way Research.)

Finding Your People in the Digital Wild West

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Social media marketing can feel like trying to be cool at your teenager’s party: sweaty, confusing, and slightly humiliating. The secret? Don’t be everywhere—just where your people hang out.

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Reality check:

• Facebook: Where your actual customers are (and your mom)
  
  
• Instagram: Pretty, polished, and good for faking composure
  
  
• TikTok: Terrifying but powerful—like parenting
  
  
• LinkedIn: The world’s fanciest brag board
  
  

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The Numbers Game (Without the Rejection Tears)

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Sales in midlife isn’t about being pushy. It’s about being helpful at the right time.

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Older entrepreneurs succeed because we build better relationships. (American Economic Review.)

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We’ve spent decades reading rooms, moods, and passive-aggressive emails. Turns out, that’s business school.

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Laugh Line

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Follow your dreams… but maybe stretch first. 

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Life Line

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Start before you’re ready. Your business doesn’t need to be perfect—it needs to be helpful.

Test your ideas. Adjust. Go again.

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Your wisdom is your competitive advantage.

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Glossary Schmossary

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New to GenSando? Words are hard sometimes.

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Your decoder ring, straight from the cereal box of midlife, awaits:

👉 Glossary Schmossary

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Proof We’re Not Making This Up

• MIT Sloan: Age and High-Growth Entrepreneurship
  
• World Economic Forum: Why You Should Wait Until Your 40s to Become an Entrepreneur  
  
• Forbes: Too Old To Become An Entrepreneur?
  
• Startup Regions: Why the Average Successful Entrepreneur Is 45 Years Old  
  

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P.S. From MILF & Silver Fox

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A cold cup usually means you handled five other things first. Reheat it. We’re here while you rebuild yourself.