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Grow Your Side Hustle With Instagram Direct Messaging Personalized, helpful outreach can go a long way.

By Nick Wolny Edited by Frances Dodds

Opinions expressed by Entrepreneur contributors are their own.

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As Instagram passes the ten-year mark, the social media app has become more popular than ever, especially for businesses: A third of all Instagram Stories come from business accounts, and 20% of these posts elicit at least one direct message from a consumer.

While new video filters and widgets roll out each month to help us create better content and express ourselves, the app's most lucrative feature is one that entrepreneurs may easily overlook: Direct messaging.

Business owners and consumers alike are becoming increasingly comfortable with conversation within the direct messaging function. This is a big opportunity if you're just getting started with a new product or service and need a scrappy, zero-cost outreach strategy.

With direct messages, you can privately build your network and even pitch your services. Since Instagram also houses all your past posts on your profile for browsing, you can show off your work and let prospects vet you without ever leaving the app.

Users now spend nearly an hour a day on Instagram alone, and you can use that hour to cash in on your side hustle. Here are three suggestions for using Instagram DMs as a lead generation strategy.

Related: 8 Examples of Brilliant Instagram Marketing

Offer free help at the outset

Personalization continues to be a white-hot trend in marketing. Rather than copy-and-pasting a bland message a hundred times over and spamming everyone in sight, take a moment to examine the account of each prospective business you find. Identify where you might be able to help out. Then send a thoughtful, customized message and offer to serve them — for free, at first.

Almost no one is willing to spend the time or resources it takes to offer a pro bono trial period, which is why this approach can give you a competitive advantage. If and when you deliver great results, the receiving party is more likely to engage with you, refer you, or even buy from you.

In psychology, it's called the law of reciprocity. When you go out of your way to help someone, they're more likely to be open to working with you or helping you in the future.

The key is to make it dead-simple for your prospect to say yes. Here are a few things to keep in mind:

  • Avoid open-ended questions. "Need help with something?" is a death trap because it asks an already-busy business owner to stop what they're doing, think, and then type out a response to a stranger in their inbox. Lead with a simple yes/no question instead.

  • Offer something that decompresses them. Perhaps you offer a free trial of your service, or a way for them to produce more marketing content (writing, photo editing, videos) without lifting a finger on their end.

  • Keep it short. In a texting, direct-messaging culture, short and sweet will help to encourage conversation. If you drone on and on about how great you are, the conversation feels more like a monologue than dialogue.

It's much easier to retain an existing client than it is to close a new one. Make those on the receiving end of your direct messaging efforts feel like they are already clients of yours before they cough up a dime.

Related: How to Use Instagram: An Introduction to Instagram Marketing

Have a portfolio

Why Instagram in particular? Unlike other platforms likw LinkedIn or email outreach, Instagram makes it easy for users to jump from the direct message inbox straight to your profile to vet you and see examples of your work.

Over 80% of prospects want to see how your product or service works within the very first touch point. Use your own account's feed and Story highlights to show off past work and and generate interest. The advantage of doing free work is that you'll build your portfolio, and being able to show someone what you do is so much more powerful than trying to explain to them what you do.

When doing free work or just getting started with a side hustle, keep a few things in mind:

  • Document the before and after. Your free work might lead to an impressive transformation in business or personal results. Before-and-after content is clean, compelling and easy to understand, but may be harder to create if you forget to document day one.

  • Use yourself as an example. Do you create video montages? Even if you're pitching businesses, content in which you are the subject can help to illustrate the point and show off your technical prowess.

  • Ask happy clients if you can name-drop. In the age of the Internet, prospects spend more time weighing their options and comparing services than ever before. If you've done work for another client and they were pleased with the results, name-dropping them and making them available for questions could be what seals the deal for your next client.

Develop thick skin

You're going to get quite a few no's and even more prospects will flat-out ignore you. Don't let this discourage you: Sales is ultimately a numbers game, and receiving rejections is just business as usual. Consider these statistics on sales conversion metrics:

  • 44% of salespeople give up on a prospect after one phone call

  • 63% of people who ask for more information won't buy for over three months

  • Replying to a lead within one hour makes it 7 times more likely you'll have meaningful conversation with an important decision-maker.

No matter what industry your side hustle falls into, strong sales muscles will help you grow. If you're willing to put in the work, Instagram can serve as more than a highlight reel of picture-perfect selfies and vacation photos. Play the long game, set time aside each week to prioritize outreach, and you'll welcome both rejections and revenue with open arms.

Related: 7 Marketing Tips to Help Grow Your Brand on Instagram

Nick Wolny

Editor, Journalist, Consultant

A self-described “editorial mutt,” Nick Wolny is an editor, journalist and marketing consultant of seven years. He writes and edits about money, business, technology, LGBTQ life and how they intertwine. Learn more at

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