How Retirees (And Teens) Can Find Their First Side Hustle Customers
The 2025 MarketWatch Guides Side Hustles Survey shows 72% of Gen Zers have worked a side hustle in the last year. But these often micro-entrepreneurial ventures aren't just for twenty-somethings. The same survey indicated 31% of those in the Baby Boomer/Silent Generation age bracket are running side gigs. With nearly one in four of all people using these small businesses to create additional spending cash, you can be sure they're becoming a viable strategy for retirees.
At the other end of the spectrum, even teens are getting in the game. Teenage side hustles can go well beyond the lemonade stand meme popularized generations ago. These money-making opportunities can produce enough revenue to fully fund the annual contribution of a Child IRA.
But it all starts with Customer #1. That person (or entity) validates your hustle. It gives you the confidence and the momentum to push on.
After that, it all gets easier.
Face it, the excitement of starting a new business—and that's precisely what a side hustle represents—can overwhelm you. But in a good way. The joy of creating something that never existed empowers you. The job of convincing someone to buy it, however, may overpower you.
That's normal. That shouldn't hold you back. In fact, here's a piece of common-sense advice that may just calm any nerves you have. Most new entrepreneurs overlook their greatest asset—the people they already know. In business jargon, that's called your 'existing network.'
Here's the crazy thing. You don't even have to use a sales pitch. You just need to have a normal chat over coffee (or whatever beverage you prefer). These people—friends, family, former coworkers—they all know you. You don't have to pretend to be someone you're not. Besides, they'd see right through that façade.
Be yourself. Be conversational. Merely let them know what you're up to.
And don't do all the talking. Purposely pause at points where it's natural for them to start asking questions.
That's the key. Get them talking. Get them curious. Get them to probe you. The more they talk, the more they convince themselves they're interested. That's when you can switch into sales mode, if you even have to. Very often, they'll sell themselves.
'I received my first customer by doing market research and reaching out to a group of friends for feedback,' says Judy Ta, a business coach at Judy Ta LLC in Torrance, California. 'I would ask them about challenges they have, competitors, thoughts about my industry, and for feedback on my business idea. One expressed interest, so I transitioned it into a sales pitch, which led to a follow-up conversation and my first sale.'
Retirees generally have vast personal and professional networks. You don't have to speak to all of them. Pick the ones most likely to offer reliable feedback. This is so natural that even an introvert can do it.
So, rest easy. You don't need to be a social media influencer to make sales.
After that first sale, strike while the adrenaline is still flowing. Don't let any lack of sales experience constrain you.
You don't need a fancy online presence to get started (although, face it, this does help, especially if your potential buyers expect it). Many retirees succeed by leaning on that old-school tradition: the human connection. This means hawking your goods face-to-face. If you don't have a marketing background, you might find the act of selling a bit intimidating.
'I retired from the Air Force after 27 years and started my own company,' says Bill Barrington, founder of Barrington Leadership Group in Arlington, Virginia. 'My greatest challenges were self-promotion and marketing—neither are skills that are taught in the military.'
Like any new skill, you can learn the art of selling through small steps and reframing the concept. Maybe you're not selling. Maybe you're solving a problem.
Or perhaps you should consider how you learned new things when you were still in high school.
What motivates teenagers? Independence? Control? Rewards? When you think about it, these are the same things that motivate many adults and, most especially, entrepreneurs.
Why is it that teens know the purpose of all the remotes in your house? Why is it that, when your computer raises your ire, you call your teenage grandchild for advice? Heck, it's getting so bad you need a high schooler to show you how to run the dishwasher.
It's not that they're smarter than you. It's that, when they put their mind to doing something, they energetically dive in. They can do that because they have a lot of free time.
You know who else has free time? Retirees.
And if you're ready to return the favor for all the times your eighth-grade grandson cleaned out your gutters (or the inbox in your email), now's the time to teach him about the power of compound interest. Better yet, you can have him run his own side hustle in tandem with you. Side-by-side side hustles. Not only can you both learn, but you can both learn together.
You see how reframing works? You went from dreading the idea of 'selling' to enjoying quality time with your kids or grandkids.
'Many of the moms I coach start carts with their kids — not just to make money, but to build something together,' says Jennie Blackwood, founder of Social Graze Charcuterie Bar + Cart to Cashflow Coaching in Loomis, California. 'It becomes a bonding experience and a hands-on way to teach teens business basics, customer service, budgeting, and pride in ownership. Some even go on to run their own carts, and I've seen families use the earnings to open Roth IRAs or save for college. But beyond the money, it's about mindset. These moms are saying, 'I want my kids to see you don't have to follow the grain—if mom can build something from scratch, so can you.' And that belief is worth more than any startup capital.'
Who knows? If you're working with your child or grandchild, consider practicing together to discuss the features and benefits of each of your side hustles. This will give you a chance to see what life is like on both sides of the selling fence.
If you've never started a business before, particularly if you're retired, it's easy to fall prey to the burden of perfection. Accomplished entrepreneurs know that the secret to success is simply to start. Don't delay. Start scrappy. You can refine things as you go along.
What's that famous GE catch phrase? 'Ready. Fire! Aim.' Don't be afraid to fix things on the fly. Don't overemphasize your 'grand opening.' This is only a side hustle. Speed tends to reward. Winners get there first. Those who hesitate fall behind.
'They get caught in the trap of 'I need everything perfect first,'' says Blackwood. 'Logo, pricing, website—they delay action until they have it all figured out. But done beats perfect every time. Share the journey. Show your face. Talk about your idea before it's polished. The people who support you early are buying you, not your branding.'
Indeed, you'll find your confidence won't start building until after the first few sales, not before. Why? It's your authenticity and connection that seal the deal, not your product. After that, if your product truly solves a significant problem, it will begin selling itself.
What evidence should you be looking for that your side hustle is selling itself? That depends on your product and the marketing method you use. If you're selling a book, you'll begin to see sales go up without any advertising. If you're providing a service like cleaning out gutters (or email inboxes), the phone will start ringing before you're done with your next job.
This implies you've got sustainable word-of-mouth advertising. You stoke this by focusing on referrals, obtaining testimonials, and public visibility. (Of course, a consistent, well-performing product underpins all of this.) Remind satisfied clients to refer you to a friend. Ask them to provide a testimonial you can use. Above all, make sure people see you out there, wherever your potential customers hang out.
'Referrals were key,' says Chris Sorensen, CEO at PhoneBurner in Seattle, Washington. 'I made sure each customer had a great experience, then simply asked if they knew anyone else who could benefit. That steady word-of-mouth helped me grow without needing a big marketing budget.'
Also, social sharing and gratitude posts offer a double bang. Not only do they get your name out, but they get your customers' names out, too. Everyone appreciates a 'thank you' (remember the response you got to those handwritten thank-you notes your mother forced you to write?). Doing this can create a reciprocity cycle that can, in turn, become a mini-marketing engine for organic growth.
You don't need a business plan. You don't need a marketing degree. All you need is an idea, a network, and the will to act.
It doesn't matter which end of the age spectrum you're on. Whether you're a senior side hustler seeking more spending money or a teen entrepreneur looking to fund a Child IRA, these tips work.
Are you intrigued by the opportunities a side hustle can offer you? Use your hobby as a launching pad. It makes the journey easier than you can imagine. Not only does the internet offer a seamless distribution opportunity, but it also serves as a free resource library.
Would you like to find out more about senior side hustles and other entrepreneurial topics? Click here to sign up for Chris Carosa's newsletter and receive a free three-step checklist to determine if your idea has what it takes to succeed.
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