The Possible Pitfalls of the Lifestyle Firm and Special Guest Tyler Winn


In Episode 60, Jason and Greg continue a previous discussion (see Episode 58) about the possible pitfalls of the Lifestyle Firm. Much of it centers around considering the people involved and the processes you need to serve. Also being careful about your assumptions is key. Then Tyler Winn of Cirrus Payroll joins them and shares how he has designed his firm to fit his lifestyle. The guys discuss Tyler’s ability to work from anywhere as well as his decision to niche with a service and how he is fighting the commoditization of payroll as a service.

Thank you to our sponsor Avalara. And be sure to check out Trustfile while visiting their site as well as their Avacash referral program (where YOU can earn cash!).

Mentioned in the show:

Cirrus Payroll
Epsiode 58: The Truth of the Lifestyle Firm
Tim Williams
Episode 44 with Josh Zweig
Wifi in the Dominican (LiveCA article)
Deeper Weekend

Audio Engineering by: Aaron Dowd

Produced by: Jennifer Blumer

About our guest: Tyler Winn

Tyler Winn helps small business owners effortlessly manage payroll with easy online systems managed by skilled professionals.

He is a CPA and loves working with other CPAs, accountants, and bookkeepers who want to outsource their clients’ payroll to a reliable and easy-to-work with service. His team speaks “accountant” and acts as an extension of your team to serve your clients in the payroll arena.

Tyler has been a member of Thriveal for about 5 years and enjoys serving his clients from Oklahoma or anywhere in the world with a good wifi connection. He and his wife travel frequently as a part of enjoying his lifestyle firm.

Tyler Winn


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