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Gail Doby - The Top 10 Challenges Small Business Owners Face

This show is going to be a bit different. You get to listen in on an open conversation with another self-employed business owner that gets it. Gail Doby is the cofounder of Gail Doby Coaching and Consulting. She has a BSBA in finance and ran her own Denver-based design firm for two decades. She has helped designers, architects, and other creatives increase their revenue by up to 512%. What the world needs now is real in the trenches business conversations. The two of us combined have over 74 years of actual business experience. We get open and honest and talk about the top 10 challenges that small business owners face.

We talk about getting paid what you're worth. The importance of being a stellar listener and conquering those money mindset issues. The importance of having a great financial model. The usefulness of business plans and how having structure can also be more important than having a business plan. We also cover money issues, financial planning, and managing the ups and downs. We also talk about the importance of having money in the bank and how it can buy you time when things become uncertain.

Too many people focus on sales instead of profit. We talk about why this isn't the best strategy. We also have a great conversation about how people work against themselves. Hint: have the courage to raise or even double your rates. We talk about how success and personal development are directly correlated. This conversation is peppered with real business stories and mindset shift strategies that will make a difference. We also talk about systems, organization, and the best place to apply your valuable time and effort.

And be sure to subscribe to The Self-Employed Life in Apple podcasts or follow us on Spotify or wherever you listen to podcasts so you don’t miss an episode.

Everything you need can all be found at

Gail Doby thank you so much for being here!

Remember, you might be in business FOR yourself but you are not in business BY yourself.

Be your best self. Be proud and keep changing the world.

Guest Contact

Contact Jeffrey

Valuable complimentary resources to help you-

  • The Self-Employed Business Institute- You know you're really good at what you do. You're talented, you have a skill set. The problem is you're probably in a field where there is no business education. This is common amongst self-employed people! And, there's no business education out there for us! You also know that being self-employed is unique and you need better strategies, coaching, support, and accountability. The Self-Employed Business Institute, a five-month online education is exactly what you need. Check it out!

  • Take The Self-Employed Assessment! Ever feel like you're all over the place? Or frustrated it seems like you have everything you need for your business success but it's somehow not coming together? Take this short quiz to discover the biggest hidden gap that’s keeping you from having a thriving Self-Employed Ecosystem. You’ll find out what part of your business needs attention and you'll also get a few laser-focused insights to help you start closing that gap.

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Host Jeffrey Shaw is a Small Business Consultant, Brand Management Consultant, Business Coach for Entrepreneurs, Keynote Speaker, TEDx Speaker and author of LINGO and The Self Employed Life (May 2021). Supporting self-employed business owners with business and personal development strategies they need to create sustainable success.


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