First encounters with tech debt in legacy systems

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What if the biggest reason your team feels stuck isn’t money, but the weight of your own code?



In this episode, I sit down with Lou Franco, author of Swimming in Tech Debt and a veteran software engineer who’s been a founding engineer at three successful startups, a principal engineer at Trello through its Atlassian acquisition, and now an advisor to software teams.

We trace his journey from early lessons in fintech and startup acquisitions to the moments that exposed just how costly ignored tech debt can be. Lou shares what he learned from engineers on the ground, how small fixes can deliver outsized productivity gains, and why culture and process matter just as much as code when tackling debt.

You’ll Learn:

• The reason most engineering teams carry hidden tech debt without clear solutions
• What happens when day-to-day friction drags down delivery speed and morale
• The ROI of small, focused fixes that start paying back almost immediately
• The damage that builds when debt is ignored until it hits a breaking point
• The link between a product’s lifecycle stage and the right level of debt reduction
• Why dedicated engineering-led time creates accountability and better outcomes
• How visible progress metrics help leadership see the value of paying down debt
• The risk of jumping too fast into shiny new tech that stalls out in production
• The role of culture, style guides, and clear values in preventing runaway debt

Timestamps:

[00:00] Introduction

[05:01] Early lessons on tech debt in fintech and startups

[07:02] The exit interview that exposed ignored debt

[08:59] Small fixes that delivered immediate productivity gains

[11:00] When debt grows into brick walls and forced rewrites

[14:01] Building team culture and values to tackle debt

[16:59] Splitting engineering-led time from product-led work

[23:00] Measuring debt payoff with metrics and visibility

[29:01] Leading indicators of productivity and developer experience

[36:59] High-risk systems, regressions, and measured approaches

Resources Mentioned:

Swimming in Tech Debt by Lou Franco | Book

Crossing the Chasm by Geoffrey Moore | Book or Audiobook

You can connect with Lou on LinkedIn and find his book here.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.