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The Sassy Strategist: Build a Profitable Business and a Lifestyle You Love

The Sassy Strategist Podcast brings you the "how-to's" of building your business so that you can achieve high profits, long-term success, and a fulfilling life. If you're a solopreneur or small business owner and offer creative, professional, or consumer services, this podcast is for you.

Host, Kim Dawson shares insight and effective strategies to help you build a profitable business that brings you joy, purpose, and the lifestyle you desire. Kim also interviews subject matter experts to share their experience and expertise on a variety of small business topics.

About the Host: Kim Dawson is a Business Strategist, Author, Speaker, and Entrepreneur specializing in helping solopreneurs and small business owners enjoy financial freedom and a fulfilling, well-balanced life. Kim strives to help you create financial security from your business, along with more free time, more joy, and less stress. Her specialty areas include revenue generation, profit strategy, pricing, scaling, business development & growth. Kim is the author of "Passion To Profits: Your Guide To Building A Successful Business You Love."

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Oct 30, 2020

Like many small business owners, Abby started her business on the side, working as a copywriter and content creator, while working full-time as a school teacher. She now runs a successful business with employees of her own.

On this episode of the podcast, Abby and I talk about taking your business through many different stages of growth, including updating, or even changing your services as your expertise and your market grow, learning to let go as we begin to hire contractors and employees, and the many mistakes we make along the way (Abby confesses to going through several hires early on before realizing she wasn’t prepared to hire effectively just yet!). 

We also discuss the pros and cons of hiring contractors vs. employees, and when it’s time to transition from the former to the latter. As an added bonus, we also discuss specifically hiring a content strategist for your business as one of several people you may want to add to your contractor team, and why doing so can really fuel your business forward.

“If you’ve been in business for 5-6 years, going the DIY route or educating yourself on [content creation] is not what you need. You need to delegate this work out at this point in your business.” - Abby Herman




  • Marketing is critical, even when business is good - “Stopping when you’re full creates hills and valleys in your income”
  • As a CEO, your job is to run your company, and it’s not doing all the things in your business.
  • Many business owners may start with independent contractors, but there is a limitation with hiring contractors, and you will need to eventually transition to hiring employees.

  • Letting go as a business owner is hard - but understand you are building a relationship with someone when you hire them, and this takes time. Be patient with the process.




Abby Herman is a content strategist and coach for service-based business owners who want to gain visibility for their businesses with personalized content strategies and implementation. She specializes in idea generation and content strategy and delivery so her clients can keep on doing what they love in their businesses, making the marketing piece feel easy. Abby is the voice behind the Stories in Small Business podcast where she features guests and solo episodes to talk about business growth and mindset, content strategy and visibility. She hosts Content Mastery Lab, a growing membership program to help newer business owners DIY their content marketing, because she knows from experience that there’s nothing more frustrating than not knowing where to start. You can connect with her on Instagram, Facebook and LinkedIn.