243: Side Hustle Coaching: I’ve Got Some Traction, Now What?

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Sarah Miller is still in college (and plays soccer for her school) but that hasn’t stopped her from starting a pretty cool side hustle: painting custom pet portraits.

She’s done 300 paintings so far!

But the business isn’t without its challenges. As a freelance artist, she’d like to raise her rates, expand her marketing efforts to land new clients, and figure out how to make her work less of a time-for-money tradeoff.

To help me brainstorm some ideas for Sarah, I invited Don the Idea Guy back on the program to join us on a call.

As you might remember, Don is a creative genius and in this episode he definitely doesn’t disappoint. Together we walk through a dozen different ways Sarah could take her operation to the next level and open up new income streams.

Even if your business has nothing to do with painting wiener dogs, I think this conversation will get your gears turning because the broader strategies can apply to lots of different business models.

Among the suggestions:

  • Raise prices for the custom work.
  • Create off-the-shelf prints for the most popular breeds (from the library of work Sarah’s already done).
  • Use print-on-demand marketplaces to instantly expand inventory and sales options.
  • Her various upsell and cross-sell opportunities.
  • Partner with influential pet bloggers and Facebook group administrators.
  • Partner with pet-related stores w/ a low-tech coupon code-based affiliate program.
  • Partner with other pet-related Etsy sellers to cross-promote each other’s products.
  • Tap into your database of existing customers for upsells and referrals.
  • Turn the preliminary pencil sketches into other product offerings and maybe even adult coloring book templates.
  • Teach others the skill of painting on Udemy.

I think you’ll like it!

Here’s an example of Sarah’s work:

And if you want more Don the Idea Guy, he’s been on the show twice before:

Check out the show and let me know what you think!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

8 thoughts on “243: Side Hustle Coaching: I’ve Got Some Traction, Now What?”

  1. Great show Nick! In my own anecdotal research over the past 20 years in the art biz it seems terrible artists (but great marketers) can do quite well financially while great artists but terrible marketers don’t stand a chance. It’s sad, but true, just how important marketing is. It’s everything really when it comes to generating income. I’m glad to see this young lady is majoring in marketing and not art, like I did. … hopefully it serves her well :)

  2. Love the coaching podcasts! Took away several notes on how I can implement the ideas in this call. I’ve listened to several podcasts aimed at artists and this one had some of the best do-it-now items I’ve heard. Thank you :)

  3. Hello. I loved this episode. I have a pet business and I just loved the ideas. It gave me ways to branch out of what I am doing, and reminded me again how pet owners think. You and Don are great together. I would love to have feedback and ideas like you did for Sarah.

  4. The only thing I enjoy more than recording these episodes with Nick is reading the awesome comments after Side Hustle Nation gets a chance to listen — thanks for the great feedback. I’m happy to be a “citizen” of Side Hustle Nation!

  5. Enjoyed hearing the brainstorming and idea-generation. I completely understand the idea of going with the most popular dogs to widen your market based, but I wonder if later a switch to other breeds may be advantageous. For example, Afghan Hounds — not very many of them, but my impression is that people who get them are: a) are really proud of that breed, and b) rarely see art or other products customized to their animals. Perhaps there is a sweet-spot of breeds that are a little less popular, but also very unique. I’m thinking like: Cavalier King Charles, Bichon Frise, and Bernese Mountain Dogs. In other words, instead of competing for a sliver of the Labrador Retriever market, you get 50%+ of the Bichon Frise market and others. This would only work if you have a broad market range and people could find your work. Best of luck Sarah!

  6. @Jason, absolutely!
    There is an audience for everything — you just have to find it. Your idea to feature some passionate-but-perhaps-not-as-massively-popular breeds is totally valid. But since Sarah was just starting to branch out, I wanted to make it as easy as possible, and not have to search too hard for this new target customer. Going with the most popular breeds meant she’d have the largest audience. However, easiest to test some passion-level breeds along the way — but I’d probably go with a 2:1 ratio until one strategy proves more profitable (or more fun!)


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