cash bags, casinos & audits: how first jobs shape us | arc

“as an auditor, you learn how non-financial events end up having a financial impact.”

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accounting arc
with liz mason, byron patrick, and donny shimamoto
center for accounting transformation

on this episode of accounting arc, liz mason, cpa; byron patrick, cpa.citp, cgma; and donny shimamoto, cpa.citp, cgma, revisit their first accounting jobs. the conversation underscores how early exposure to operations, technology, and industry economics cultivates the judgment accountants need to interpret business realities.

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from hustling down the beach with bags of money to deploying field laptops with new tech to counting millions of dollars over 15 hours, each host shares a unique accounting beginning, but all have the same clear messaging.

patrick, ceo of verifyiq and co-founder and educator of tb academy, got his introduction to accounting in a family-owned hospitality group that ran 13 hotels and four restaurants in ocean city, maryland. in addition to payables and helping with consolidations, he was tasked with physically transporting locked cash bags between properties—a reflection of a largely cash-based environment. “there were controls in place,” he recalls, but the experience made risk tangible and emphasized the importance of separation of duties and reconciliation. the role also hinted at a future in accounting technology as he helped set up computers across locations.

for shimamoto, founder and managing director of intraprisetechknowlogies llc and founder and inspiration architect for the center for accounting transformation, his first paid job focused on data entry and month-end ap work at a logistics company. however, his first internship moved him squarely into technology at coopers & lybrand—later pwc after the 1998 merger with pricewaterhouse—where he deployed laptops and helped roll out a lotus notes–based paperless audit platform. he was simultaneously upgrading a novell netware network, applying classroom learning directly in the field. the experience illustrates how technology has long been integral to audit and assurance, predating today’s cloud and ai tools.
mason, ceo of high rock accounting, began in casino audits, a niche that demanded strict control awareness. as a junior auditor, she observed cash drops on the gaming floor, accompanied security, navigated metal detectors, and followed procedures that required visible hands and no personal items inside the count room. when counting machines failed during a year-end observation, she watched teams hand-count several million dollars over 15 hours. the episode was grueling, but it cemented an appreciation for process, redundancy, and documentation.

later, mason detected a significant year-over-year change in craps’ profitability and traced it to marketing that had attracted new, inexperienced players. verifying the explanation required matching tourist bus logs to revenue timings and documenting causation, not just correlation. it was an early lesson in connecting non-financial drivers to financial results. “you become a financial interpreter,” she says, translating operations, strategy, and risk into the language of money.

the hosts suggest that new professionals consider sectors that both interest them and possess healthy margins. mason is blunt: whether in-house or external, accountants are often treated as overhead, so working in profitable industries can improve compensation and resources. patrick adds that nearly every domain—from sports to hospitality to nonprofits—needs accountants, making it possible to align work with personal interests.

for patrick, public accounting provided rapid exposure to diverse organizations and models, accelerating his understanding of what drives (or undermines) profitability. shimamoto echoes that breadth, noting that auditors must learn to anticipate how business events—tariffs, supply chain disruptions, technology changes—will ripple through costs and revenues, and ultimately the financial statements.

across their stories, a throughline emerges: early roles that force close contact with operations and systems help accountants develop judgment—the ability to connect events to effects. that judgment becomes indispensable as the profession embraces new tools and addresses evolving expectations.

6 key takeaways

  1. first roles that put you near operations and controls (hotels, gaming floors, logistics) accelerate learning far beyond debits and credits.
  2. early exposure to technology (from lotus notes and netware to today’s ai) shows how tools shape audit and advisory work.
  3. the best accountants become financial interpreters, connecting business events—like marketing campaigns—to measurable financial outcomes.
  4. industry selection matters. where margins are healthy, accountants typically have more resources and impact.
  5. public accounting is a launchpad: varied clients build pattern recognition and professional judgment quickly.
  6. grit and odd hours (yes, 2 a.m. observations) often come with the territory—but the experience compounds over a career.

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