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The 5 Questions Every Business Owner Needs to Ask Before Hiring a Virtual Assistant


Whether you’re the founder of a start-up, a small business owner or an independent consultant, inevitably you wear all the hats.

In fact, as founder of The Upside, I’ve been CEO, CMO, COO and CTO (just to name a few) since the initial launch of my business. Scarily, I was even my own lawyer at one point.

But as a bootstrapped founder, I was so used to doing everything myself, that when The Upside finally had the revenue to support hiring additional help, I had trouble letting the work go, even though I absolutely needed to in order to have the bandwidth to scale my company.

In our latest article for Thrive Global, we ask Michelle Penczak, founder of SquaredAway and virtual assistant expert: How do you find the perfect virtual assistant?

Read the full piece here.

Named Marine Corps Base Kaneohe Bay Military Spouse of the Year 2019, Michelle Penczak is a virtual assistant by trade and a military spouse by love. Her husband Sean is a pilot in the Marine Corps. Through multiple relocations and deployments, Michelle has built a vibrant, thriving independent virtual assistant business for herself over the past 5 years. Her own experience as a military spouse gives her unique insight into the multitude of challenges facing other military spouses who want to have a career of their own, but struggle to find gainful employment local to their latest duty station. SquaredAway’s pool of unique & talented personalities is where a significant amount of her assistants are chosen.

Erin Halper is the founder and CEO of The Upside, a platform that launches and grows independent consultancies for ambitious professionals redefining success beyond the 9-5. Since launching The Upside in 2017, Erin has advised more than 1,000 professionals on how to build a thriving consultancy, and has matched more than 100 businesses with consultants and freelancers in The Upside’s network.

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