Melissa Armstrong is the founder of SteadyHand Accounting & Advisory, a firm dedicated to helping businesses gain financial clarity, optimize operations, and scale strategically. A third-generation accountant, Melissa’s journey began at Deloitte, where she worked in tax compliance before moving into financial planning at Banco Popular. Her career has spanned various roles, including corporate controller positions and advisory roles at firms like Plant Moran. Now, as an independent financial consultant, she provides fractional controller services, financial oversight, and advisory support to businesses that need strategic financial leadership. In our conversation, we delve into:

• Transitioning from Big Four firms to entrepreneurship

• The evolution of accounting as a profession

• The value of fractional controller services for businesses

• How growing up in an accounting family shaped her career

• The role of community and networking in business success

• Leveraging AI and automation in accounting

• Challenges facing the accounting profession and its future

1. Accounting is a Borderless Profession : Despite regional differences in financial regulations and business environments, accounting principles remain universal. Mastering financial fundamentals allows professionals to work across industries and geographies.

2. Entrepreneurship Demands Purposeful Reinvention: Transitioning from a structured corporate role to building an independent firm requires continuous learning and reinvention. Entrepreneurs must develop new skills beyond accounting such as business development, marketing, and leadership, to sustain and grow their ventures.

3. Technology Liberates Human Potential: Automation, AI, and digital transformation are redefining the role of accountants. By leveraging these tools, financial professionals can reduce time spent on transactional tasks and focus on strategic advisory.

4. Authentic Relationships Drive Professional Success: Technical skills are essential, but relationships build careers. Trust, transparency, and strong client communication are key factors in long-term business success. A focus on relationship-building whether with clients, mentors, or colleagues can lead to referrals, partnerships, and new opportunities.

5. The Profession's Survival Requires Evolution: Accounting is undergoing a fundamental shift. With increasing automation, firms that rely solely on compliance work may struggle to survive. The future of the profession lies in strategic advisory, financial planning, and value-driven services. Accountants who embrace change and develop expertise in emerging financial trends will be best positioned for success.

6. Cross-Disciplinary Experience Creates Competitive Advantage: A diverse background in tax, financial planning, and corporate finance provides a well-rounded perspective that benefits businesses. Professionals who expand their expertise beyond traditional accounting such as gaining exposure to business strategy, operations, and technology will have a stronger competitive edge in the evolving industry.

Where to Find Melissa Armstrong:

• Website: https://steadyhandaccounting.com/

• LinkedIn: https://www.linkedin.com/in/armstrongmelissacpa/

  
  

In this episode, we cover:

• 01:57 – Introduction to Melissa's Journey

• 07:45 – The Landscape of Accounting in Puerto Rico

• 14:52 – Starting Capitalized Consulting

• 22:40 – The Evolution of the Accounting Profession

• 24:50 – The Value of Accounting Professionals

• 31:19 – Embracing AI in Accounting

• 34:20 – Technology Adoption in Accounting Firms

• 38:47 – The Fast Five Questions

  
  

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Doyin Ogunbajo is the founder of ASO Financial, a firm dedicated to providing strategic accounting, tax, and financial advisory services to businesses. With over 13 years of experience, he has worked with major clients, including the U.S. Department of Defense, FCC, and Department of Homeland Security. Before launching ASO Financial, Doyin worked at EY, where he specialized in financial reporting and tax solutions, and Deloitte, where he served as an ERS Consultant supporting risk assessment and internal controls for government clients. Today, he leverages his deep expertise to help businesses thrive and navigate financial complexities. In our conversation, we delve into:

• Transitioning from Big Four firms to entrepreneurship

• The value of financial advisory services in small businesses

• How government and nonprofit experience shaped his approach

• The role of technology in modern accounting firms

• Business development strategies for firm owners

• The impact of community and networking in accounting

• The future of accounting and the profession’s talent shortage

1. Accounting as a Universal Skill: Despite differences in regulations and business environments, accounting principles remain the same across industries and regions. Mastering financial fundamentals and adapting them to different contexts is essential for long-term success.

2. Entrepreneurship Requires Adaptability: Transitioning from a structured corporate environment to running an independent firm presents unique challenges. Building a business requires balancing client acquisition, branding, and operational efficiency while staying resilient through uncertainties.

3. Community and Networking Are Key to Growth: Success in accounting isn’t just about expertise—it’s about relationships. Engaging with other professionals, sharing insights, and collaborating within a strong network can lead to new opportunities and business growth.

4. Technology is Reshaping Accounting: Embracing automation, AI-driven insights, and digital tools can help accountants streamline workflows, improve efficiency, and enhance client communication. Staying ahead of technological advancements is crucial for firm owners.

5. Client Communication Must Be Strategic: Effective communication saves time and builds stronger relationships. Setting clear expectations, using automation where possible, and leveraging tools like video messaging can simplify complex financial concepts and improve client interactions.

6. Fixed Pricing Models Build Trust: Shifting from hourly billing to fixed pricing improves transparency, strengthens client relationships, and provides more predictable revenue streams. Businesses benefit from knowing costs upfront, and firms gain stability in long-term partnerships.

7. The Future of Accounting is Advisory-Driven: With automation handling transactional tasks, accountants will need to focus more on advisory roles. Businesses increasingly rely on accountants for strategic financial guidance, making this an essential shift for the industry.

Where to Find Doyin Ogunbajo:

• Website: asofinancial.com

• LinkedIn: https://www.linkedin.com/in/doyinthecpa/

In this episode, we cover:

• 01:27 Introduction and Background

• 04:13 Passion for Accounting

• 06:37 Cultural Perspectives on Accounting

• 09:22 Transitioning to Entrepreneurship

• 11:55 Client Preferences and Impact

• 14:23 Business Development Strategies

• 16:56 The Role of Community in Business

• 22:07 Leveraging Technology for Efficiency

• 37:52 The Role of AI in Modern Accounting

• 46:48 The Future of Accounting Professionals

• 49:30 The Fast Five Questions

References:

• EY: https://www.ey.com

Thomas Kim is the founder of the Wonderful Tax Group, a firm dedicated to simplifying accounting and taxes, and providing personalized financial solutions for individuals and businesses. Previously, he spent over seven years as an Accounting Controller at Tabular LLC, managing everything from financial statements to audit support for diverse industries like tech startups, non-profits, and medical practices. Before that, he played a key role as an Accounting Consultant at CliftonLarsonAllen LLP, streamlining financial operations for a $20MM advertising agency. In our conversation, we delve into:

• Challenges of transitioning from corporate to freelance accounting

• The undervalued yet critical role of bookkeeping

• Why specialization is key in the evolving accounting industry

• AI’s impact on tax services and accounting automation

• How to build strong client relationships and trust

• The role of technology in reshaping accounting workflows

1. Balancing Persistence and Patience: Success requires knowing when to push forward and when to pivot. While persistence is crucial for making progress, understanding when to take a step back, re-evaluate, and change strategies is just as important.

2. Bookkeeping’s Value: Bookkeeping is often seen as a low-priority task, but it serves as the foundation for financial decision-making. Without proper bookkeeping, businesses struggle with compliance, cash flow management, and long-term financial planning. Accurate books are an asset, not just a requirement, and recognizing their importance can prevent costly mistakes down the line.

3. Specialization Matters: In an increasingly complex financial landscape, professionals who specialize in tax services, advisory roles, or niche financial services will have a competitive edge. The ability to provide tailored solutions and deep expertise in a specific area will be in higher demand as businesses seek professionals who can address their unique needs efficiently.

4. AI and Automation: While AI and automation are transforming the accounting profession by streamlining processes and reducing manual workloads, they cannot replace human expertise. Accountants and bookkeepers must learn how to integrate AI tools effectively to enhance their work while maintaining the critical thinking and analytical skills that software alone cannot provide.

5. Independence vs. Prestige: Many professionals face the dilemma of choosing between the stability of corporate careers and the freedom of entrepreneurship. While corporate jobs offer structured career progression and prestige, running an independent practice provides autonomy and the ability to build something truly one’s own.

6. Navigating Ethical Dilemmas: Accountants frequently encounter ethical challenges when working with clients who may be disorganized or non-compliant with regulations. Developing strong ethical guidelines and maintaining professional integrity ensures that accountants make decisions that protect both themselves and their clients, even when difficult conversations are required.

Where to find Thomas Kim:

• LinkedIn: https://www.linkedin.com/in/tk365/

In this episode, we cover:

• 01:13 Introduction and Background

• 04:16 Transitioning from Corporate to Freelance Accounting

• 06:45 The Move into Tax Services

• 09:21 Understanding the Role of an Enrolled Agent

• 12:06 Client Focus and Industry Experience

• 17:12 Success and Failure Stories

• 20:04 Adapting to Technology in Accounting

• 22:34 The Future of Accounting Technology

• 35:35 The Role of AI in Accounting

• 46:03 Future Trends in Accounting

• 50:18 Fast Five Questions

References:

• TaxJar: https://www.taxjar.com/