ByteSized

What’s the Biggest Financial Mistake in Tech Projects?

Most technology projects don’t fail because of bad software, they fail because of bad budgeting. In this episode, Kristy Barber joins the conversation to unpack the most common financial mistakes organizations make when funding new technology. From underestimating total project costs to overlooking hidden expenses like integrations, travel, and internal labor, Kristy and Adam share real examples of how projects derail when budgets stop at the order form. The discussion also explores the cost of inaction, why small pivots can become massive budget risks, and how to build a realistic financial strategy that keeps implementations on track from kickoff to go-live.
 
Watch the full episode here: https://www.youtube.com/live/n557EkJaWag 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

What Happens When Finance and IT Don’t Speak the Same Language?

When finance is focused on budgets and IT is focused on speed, alignment can feel impossible. In this episode, Kristy Barber joins the discussion to unpack why these two teams often operate on different timelines and how leaders can bridge the gap. The conversation explores how company structure, reporting lines, and budgeting cycles shape decision-making, and why many digital transformations stall on the hill of funding and unrealistic timelines. Kristy shares practical advice for setting expectations early, building cross-functional alignment, and ensuring technology priorities stay grounded in business outcomes, not departmental agendas.
 
Watch the full episode here: https://www.youtube.com/live/n557EkJaWag 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Can You Still Capitalize SaaS in a Subscription-Driven World?

The CapEx vs. OpEx debate has never been trickier. In this episode, Kristy Barber breaks down why modern accounting rules haven’t kept pace with the shift to subscription-based software and what that means for finance leaders. She explores how companies are managing SaaS costs under today’s GAAP and FASB standards, why the 80s-era playbook no longer applies, and how missteps in classification can distort your financial health. The conversation also covers why annual audits remain essential and how to navigate the gray areas as business models evolve.
 
Watch the full episode here: https://www.youtube.com/live/n557EkJaWag 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

CapEx vs. OpEx: Getting Technology Budgets Right

When should a new system be treated as a capital investment versus an operating expense? In this episode, Kristy Barber joins the discussion to break down how finance and technology teams can align on budgeting for modern systems. The conversation explores how cloud software, subscriptions, and automation have reshaped accounting strategies and why misclassifying expenses can cause serious financial and compliance issues. From understanding depreciation rules to planning for ROI and exit strategies, Kristy shares how to structure tech investments the right way so they drive long-term value instead of creating hidden costs.
 
Watch the full episode here: https://www.youtube.com/live/n557EkJaWag 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Reinvent or Reset: Lessons from the AI Acceleration Curve

Transformation is no longer slowing down; it is moving faster than most leaders can adapt. In this episode, Richard explains why legacy debt, both technological and human, is the biggest barrier to progress and how traditional vendors are struggling to keep up. Using General Motors’ acquisition and spinout of EDS as a case study, he breaks down what real reinvention looks like when it becomes a growth strategy instead of a one-time pivot. The discussion wraps with clear takeaways on how modern enterprises can reset, modernize, and lead in an AI-driven economy.
 
Watch the full episode here: https://youtube.com/live/1OIXEDvi5ww
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Rethinking Cost and Culture in the Age of AI

What happens when digital workers enter the org chart? In this episode, we explore how AI is forcing leaders to rethink everything from cost structures to culture. The conversation dives into why successful companies are shifting from fixed to variable cost models tied to revenue and how AI can target inefficiency instead of simply cutting headcount. We also look at the growing divide between shareholders focused solely on returns and those factoring social impact into performance. For executives navigating digital transformation, this episode outlines the real tradeoffs, cultural risks, and practical steps to modernize without losing the human element.
 
Watch the full episode here: https://youtube.com/live/1OIXEDvi5ww
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

The Digital Revolution vs. The Industrial Revolution

The world is shifting from industrial growth to digital reinvention, and the implications reach far beyond technology. In this episode, Richard breaks down how global GDP, workforce dynamics, and automation are reshaping the economy. He explains why the digital revolution isn’t about job creation but about redistribution of value and continuous reinvention. From digital workers that never sleep to individuals redefining their own operating models, this conversation explores how both people and organizations can adapt to a permanently changing future.
 
Watch the full episode here: https://youtube.com/live/1OIXEDvi5ww
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Educating the Workforce for the AI Revolution

How can organizations and individuals prepare for the digital revolution? In this episode, we explore why education, not hype, is the key to adapting to AI. Richard explains how companies can inform employees about what AI really means for their roles, income, and opportunities. The discussion highlights the importance of financial awareness, skill development, and wealth creativity to help people build stronger, more flexible careers in the era of digital transformation.
 
Watch the full episode here: https://youtube.com/live/1OIXEDvi5ww
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

AI, Digital Workers, and the Future of Human Work

Are AI digital workers replacing humans or changing how we work? In this episode, Richard explores how automation is reshaping the global workforce, why many daily tasks could already be handled by AI, and how shareholder priorities influence business decisions. He explains the rise of fusion work, where humans and digital workers collaborate, and how leaders can balance efficiency, profit, and human value in the modern workplace.
 
Watch the full episode here: https://youtube.com/live/1OIXEDvi5ww
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Leading Supply Chains Through Disruption

When a supply chain disruption hits, what’s your first instinct as a leader? In this episode, Greg explores how today’s most effective supply chain leaders respond under pressure. Instead of assigning blame, they focus on customer impact, evaluate options, and empower their teams to make confident, data-driven recommendations. We discuss how this shift builds organizational maturity, improves agility, and turns disruption into an opportunity for smarter, faster decisions that strengthen the entire value chain.
 
Watch the full episode here: https://youtube.com/live/Ro9iRzlV7RY?feature=share
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial