Have you ever felt overwhelmed by the financial side of your business or wondered if you need to hire some help? My guest on this episode is Holly Cain of Prosper Collective, and she’s cutting through the confusion around financial services, what exactly different financial professionals do, and when you might need one in your business.

Holly Cain smiling at desk - What kind of financial help do you need in your business?

To learn more about upLIFT, join my free Info Session: Thrive In Business, Up-Level Marketing, & Build Faith-Based Connections… Even If You Feel Scattered, Deal with Imposter Syndrome, or Don’t Have the Connections You Think Need. Visit https://upliftmentormind.com/ or text UPLIFT to (207) 544-4103.


Key Points Discussed:

  •  The 4 main financial roles and what they might do in your business:
    • CPA/Accountant: This person does your taxes; he or she is a tax advisor and should give you advice and strategy on how to maximize your tax position. You may talk to this person a couple times a year.
    • Bookkeeper: There is a wide range of what this role can look like. Typically they do your books (daily, weekly, or monthly transaction, reconciles, make sure things are entered correctly). They will also review your numbers with you at a certain cadence. You typically talk to this person monthly or weekly.
    • CFO (Chief Financial Officer): This person is responsible for your business’ full financial picture. They usually work with your bookkeeper, accountant, and financial planner to implement advice and strategy. They create plans to meet the business’ financial goals. You’ll likely talk to this person daily, or weekly or every other week.
    • Financial Planner: This person does your legacy planning (insurance, retirement, investing, estate planning). You would likely talk to this person quarterly or a couple times a year.
  • Why there is confusion about who does what in the financial sphere.
  • What Holly does in her financial business as a fractional CFO and bookkeeper.
  • How to know which professional you might need to access and at what stages of business
    • Starting out you need a CPA/Accountant
    • Next add on a bookkeeper when you can afford it (maybe around 50k total revenue)
    • Add on a financial planner – once you start making some money (when you have consistent profit) – this person is a bridge between your personal and business finances
    • Add on a CFO – potentially when you are making more than six figures or when your financial picture needs more attention on a regular basis, when you need decision making abilities more often; this person provides strategy and works with all the others
  • How to decide if you want to hire out or do things yourself.
  • How to get in touch with Holly, and her free guide with questions to ask and red flags to look out for when you’re considering hiring a financial professional. Grab the guide here.
  • More financial training available inside Esther’s new program, upLIFT. Join the upLIFT Info Session on June 7th to get all the details! Visit upliftmentormind.com or text UPLIFT to (207) 544-4103!


  • “Do you want to do it, and is it a good use of your time?” -Esther Littlefield
  • “Sometimes we hesitate to admit we don’t know.” -Esther Littlefield
  • “It’s ok to say ‘I don’t know who I need in my business and can you help me figure it out?’” -Esther Littlefield
  • “You got into business because you have a zone of genius in [an] area.” -Holly Cain
  • “Just because you are a business owner doesn’t mean you know all the things about business.” -Holly Cain
  • “It’s about filling out the team with a really robust amount of knowledge that you may not have, so you have the freedom and the mental space to actually do the thing you know how to do well…I find those people are the most successful in business.” -Holly Cain
  • “Whenever possible, delegating and bringing other people in can make a huge difference.” -Esther Littlefield

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