Unemployable with Jeff Dudan – Episode #239

Title: If You Don’t Fix THIS, You’ll Never Sell: Lessons From CEO at Decimal, Matt Tait
Date: December 30, 2025
Host: Jeff Dudan
Guest: Matt Tait, CEO/Co-Founder, Decimal

Episode Overview

In this episode of Unemployable, Jeff Dudan sits down with Matt Tait, CEO and co-founder at Decimal, to dive into the intersection of technology, accounting, and entrepreneurship. They unpack Matt’s transition from law to leading a pioneering AI-driven bookkeeping and tax franchise, offer a candid discussion on business failures and successes, and reveal the key attributes of a successful founder and franchisee. With actionable insights for aspiring business owners and those scaling service-based companies, this episode explores the systems, mindsets, and technologies redefining professional services—particularly for small-to-midsize businesses.

Key Discussion Points & Insights

The Future of AI in Professional Services

[01:30]

• Hybrid Success: Matt emphasizes the necessity of blending AI with the human factors of trust, accountability, and credibility.
  • Quote (Matt Tait, 01:55): "The glue in professional services is the trust, accountability, and credibility that humans bring. AI can’t do that—and I don’t believe it ever will."
• Rate of Change: Technology is evolving rapidly, making system flexibility and adaptability critical for companies—what worked for ten years is now outdated in months.
  • Quote (Matt Tait, 03:44): "Now you are seeing the rate of change decreasing to months, if not days. You have to be nimble enough to keep up with that.”

Matt Tait’s Entrepreneurial Journey

[04:27]

• Roots in Entrepreneurship: Growing up surrounded by business owners, Matt pursued law after advice from family, using it as a toolkit for eventual business ownership.
• Failures Before Success: Decimal is his fourth business—two succeeded, one failed, and lessons from each shaped Decimal’s explosive growth.
  • Quote (Matt Tait, 06:34): "I learn better from failure than from success. At Decimal, being imperfect is a superpower—it lets the team work together toward a more perfect goal."

Building Winning Teams

[08:14–15:55]

• Self-Awareness & Humility: Prefer hiring those with genuine self-reflection and the ability to admit failures over resumes filled with only accolades.
• Business Athletes: More than just sports experience, it’s about relentless preparation, measured tempo, and the willingness to "rush the conflict."
  • Quote (Jeff Dudan, 13:28): "I look for someone who rushes the conflict… Bad news ages very poorly. The person who can most accurately describe reality without laying blame emerges as the leader."
• Systems Thinking: Critical for franchisees and team members alike—to see both the “box” (structure) and when to break out of it for breakthroughs.
  • Quote (Matt Tait, 15:55): "Systems thinkers aren’t looking to assign blame; they’re looking for solutions today and tomorrow."

Decimal: Model & Mission

[17:09–21:46]

• What is Decimal?
  • AI-enabled bookkeeping and tax franchise, supplying the technology, operational support, and playbooks that made their original firm one of the fastest-growing in the US.
  • Now franchising: “helping others start their own firms with our tech and systems.”
• Ideal Client: Small to mid-sized businesses ($500k–$20M revenue), often using QuickBooks.
• Franchisee Role: Focuses on business development and client relationships while the central team manages operations and tech backbone.
  • Quote (Matt Tait, 19:56): "If you’re a franchisee, you focus on growing, adding clients, and helping your clients—you hire a much smaller team, and we handle the rest."
• Service Buckets: Bookkeeping, tax (returns and strategy), operational help (A/P, A/R, payroll), and advisory/M&A.

Franchising vs. Direct Model

[27:44–35:04]

• Why Franchise? Franchising empowers more small business entrepreneurs, leverages local presence, and has massive potential given the fragmented state of the accounting industry.
• Community & Collaborative Network: Early franchisees already collaborate, sharing resources and referrals, amplifying strengths across the network.
• Tech’s Role: Decimal integrates best-in-class software (e.g., Ramp, Gusto, Bill.com), reducing manual errors and inefficiency.

Advisory: From Day One to Exit Planning

[23:42–43:00]

• Starting with ‘What’s Your Goal?’ Client engagement begins by understanding business owners’ ultimate ambitions, whether growth or exit.
• The Big Mistake in Financial Literacy: Most owners fail to understand their true numbers, how EBITDA is calculated, or how financials should be presented for sale.
  • Quote (Matt Tait, 39:45): "Every two or three years, every company should get a snapshot of what their business would trade at today. It’s more than EBITDA—it’s how involved you are, how replaceable you are."
• Educational Focus: Advocacy for recurring benchmarking and financial education for clients; stories about businesses not opening even their monthly financials.
  • Quote (Matt Tait, 45:41): "We had 600 clients—under 30% even opened the email with their P&L. Under half clicked through, under half of those stayed five minutes. And these were $2–$20 million companies."

Outsourcing, Offshoring & The Global Workforce

[47:28–50:21]

• Efficient Resourcing: Technology is foundational, offshore teams handle the bulk of processing, freeing up US staff for relationship-building and quality control.
  • Quote (Matt Tait, 48:31): "US staff now focus on relationships only—and that’s perfect, because trust, relationship, and retention drive revenue. Grace comes from the human connection."

The Value of Data & Benchmarking

[51:07–54:17]

• Secondary Value Driver: Aggregated client data offers immense value for benchmarking and trend prediction.
• Benchmarking Trap: Beware of aiming for “average”—targeting best-in-class is the only way to win.
  • Quote (Matt Tait, 53:47): "Average gross margin for bookkeeping firms is 18–21%. Decimal’s is just below 60%."
  • Quote (Jeff Dudan, 54:01): "Average is just one data point above ‘you suck’."

Leadership Style & Motivation

[35:59–37:11]

• Fun but Demanding: Matt’s known for "fun but demanding… sometimes the disappointed dad," using honesty and transparency about failures to motivate.
  • Quote (Matt Tait, 36:11): "Disappointment is a great motivator for your best people. But I think praise is too. I’m deeply transparent and authentic, because talking through my own failures motivates others to try again."

Future Directions: Decimal Extensions & The Role of AI

[37:11–58:23]

• Community-Driven Expansion: As more franchisees join, the cumulative skillset of the network expands—potentially enabling business brokering or even investment banking services.
• AI’s Role in Law & Accounting: Next frontier is AI deployment in law firms; accounting tools lag but will catch up.
  • Quote (Matt Tait, 56:51): "There are much more mature AI tools for lawyers than for accountants right now."

Notable Quotes & Moments

• On Human Factors in AI Services:
  • “AI can’t do trust, accountability, and credibility. The best firms will blend tech with humans.” (Matt Tait, 01:55)
• On Embracing Imperfection:
  • “At Decimal, being imperfect is a superpower…it lets others be imperfect too, and work for a more perfect goal.” (Matt Tait, 06:34)
• On Urgency in Conflict:
  • “Bad news ages poorly. The person who can most accurately describe reality without blame emerges as a leader.” (Jeff Dudan, 13:28)
• On Average vs. Best:
  • "Average is just one data point above ‘you suck’." (Jeff Dudan, 54:01)
  • "If you're playing on averages, you're running a bad business. You should be playing towards the ideal." (Matt Tait, 53:48)
• On Motivating Teams:
  • “Disappointment is a great motivator…but praise is too. Talking about my failures makes it okay for others to fail, then get up and be better.” (Matt Tait, 36:21)
• On Business Advice for Future Entrepreneurs:
  • "Tell more people you’re proud of them.” (Matt Tait, 60:00)
  • Referencing Mr. Rogers: “More men need to tell each other they’re proud of them.”

Timestamps for Major Segments

| Segment | Timestamp | |-------------------------------------------------|-----------------| | AI in Professional Services | 01:30 – 04:27 | | Matt’s Early Career & Lessons | 04:27 – 07:43 | | Building Great Teams & The Business Athlete | 08:14 – 17:09 | | Decimal’s Franchise Model & Services | 17:09 – 23:42 | | Advisory & Exit Strategy Conversations | 23:42 – 27:44 | | Franchising vs. Direct, Community Building | 27:44 – 35:04 | | Data, Benchmarking, & Financial Literacy | 35:04 – 54:17 | | Globalized Workforce & Outsourcing | 47:28 – 51:07 | | Product Extensions, AI, and Future Trends | 51:07 – 58:23 | | Closing Curveball & Life Lesson | 55:38 – 60:03 |

Memorable Moments

• The “Land and Expand” Approach: Using a “tip of the spear” service to get a foot in the door and then solve more and more pain points for clients—leading to long-term partnerships. (34:02–35:08)
• Financial Literacy Gap: Less than 30% of business clients even glance at their financial statements monthly.
• Curveball Q&A: Matt would build a consulting company for deploying AI in professional services if he had to start over.
• Final Impact Sentence: Matt channels Mr. Rogers: “Tell more people you’re proud of them.” (60:00)

Conclusion

A candid, action-packed conversation for anyone considering their next leap in business ownership, scaling professional services, or applying AI to traditional industries. Matt Tait offers a roadmap for blending technology and the human element, developing teams for resilience, and never underestimating the power of honest, actionable feedback—all while highlighting the transformative opportunity of franchising in overlooked service sectors.