Bridget Way spent nearly two decades in the trenches of tax season before asking one question that reshaped her entire business: what if doing great work didn't have to mean burning out?A CPA based in the mountains of Colorado, Bridget rebuilt her firm around AI after a disconnected family trip to Utah during COVID convinced her there had to be a better way to work — one where technology creates more capacity while preserving the relationships that make the job meaningful.
In this conversation, Bridget and Joe cover:
• The funeral story about her grandfather (also an accountant) that reshaped how she saw the profession
• Why she calls herself a "QuickBooks desktop warrior" and how cloud accounting changed everything
• The panic-call moment in Utah that triggered her shift to boundaries and automation
• How she quantified saving 500 hours in year one of using AI
• Why she believes AI won't replace small accounting firms — and how she uses it as a "personal assistant" instead
• The generational shift in accounting culture (Gen X grind vs. Gen Z boundaries)
• How "firing" the wrong-fit clients gave her freedom
• What her grandfather — an old-school Enrolled Agent who refused computers — might think of her AI-powered practice today
Bridget is the author of Upskill or Out: AI, Small Business, and the New American Dream — part personal story, part practical guide to using AI to build a stronger, more sustainable business.
Learn more about Bridget at
https://www.upskillorout.com.
Chapters
00:00 – Intro: Bridget's journey from tax-season burnout to AI-powered firm
00:23 – Meet Bridget Way, CPA and author of *Upskill or Out*
01:01 – The story of her grandfather's funeral and its impact
02:23 – Seeing her grandfather, the accountant, in a new light
03:17 – Young Bridget: marketing major turned numbers person
04:10 – What is an Enrolled Agent vs. a CPA?
05:01 – Confessions of a "QuickBooks desktop warrior"
06:12 – The rise of cloud accounting and alternatives to QuickBooks
07:01 – Transferable skills and the post-COVID hiring shift
07:59 – The Utah trip: the moment everything changed
09:36 – Realizing "I don't have to work 16-hour days"
09:55 – Changing the business model — and the client fallout
11:37 – The AICPA Vegas conference "tech awakening"
13:15 – First AI experiment: cleaning up a messy client file
14:40 – The automation hack that saves the most time and money
16:44 – How she quantified saving 500 hours in year one
17:45 – Why AI won't replace small accounting firms
18:31 – Using AI as a "personal assistant" to punch above her weight
19:30 – Bundling in HR and other adjacent services for clients
20:12 – The post-COVID accountant shortage and AI stepping in
21:09 – Are Gen Z accountants embracing AI and boundaries?
22:34 – AI absorbing the "mundane" work so people don't have to
22:54 – Gen X banter: adapting through the pre/post-internet era
23:22 – How Millennials and Gen Z reshaped work-life boundaries
24:52 – Does tax season still get "crazy" in her practice?
25:43 – The ski trip during tax season story
26:15 – Handling clients who think "a computer is doing my taxes"
27:47 – "You know you've made it when you can fire clients"
29:09 – Redefining success: time and presence over the corner office
30:27 – "You're less edgy during tax time now" — her kids notice the change
32:04 – What would her grandfather think of her AI-powered practice today?
33:42 – Where to find Bridget's book and close
