In this episode, your hosts, Ben Nadel and Ryan Brown, sit down with Steve Leve from ShareASale to dive into the challenges and lessons learned from navigating an acquisition, managing technical debt, and executing large-scale migrations. They explore the impact of legacy systems, the balance between maintaining old infrastructure and innovating new solutions, and the role of AI in modern software development.

Key Points:

• Steve shares his journey from a small-town coder to a principal architect at ShareASale.

• The team discusses the challenges of merging companies post-acquisition, including business model differences and technical debt.

• Lessons from large-scale infrastructure migrations, including moving from ColdFusion monoliths to modern architectures.

• The importance of balancing innovation with maintaining existing systems and the trade-offs of cloud computing.

• How AI is reshaping development practices, from documentation to automated testing.

Migrating an entire business platform brings its share of surprises and roadblocks.

• Steve shares his experience of being acquired by AWIN and the growing pains that followed.

• The team discusses the complexities of merging different operational and technological approaches.

• They reflect on the unexpected technical challenges, including a looming data center shutdown and hardcoded infrastructure dependencies.

• The importance of knowledge sharing within a team to prevent reliance on a single expert.

Navigating technical debt is all about prioritization and timing.

• The group explores the idea that not all technical debt needs to be fixed—only what blocks innovation or scaling.

• Steve emphasizes "tidy first" as an approach to incrementally improving code rather than massive rewrites.

• Real-world examples of how debt manifests in migrations and why some old code surprisingly holds up.

• The discussion touches on key strategies for managing technical debt within an evolving business landscape.

Migrating to AWS and cloud adoption brings new efficiencies but also new constraints.

• Steve and Ben share stories of migrating to AWS, the surprises along the way, and the need for expert help.

• Lessons on the hidden costs of cloud adoption and why simply lifting and shifting to the cloud isn't always the best strategy.

• The team debates the trade-offs between autoscaling, managed services, and maintaining on-premise solutions.

• Real-world examples of cost-efficient cloud migration strategies.

Strangler patterns, AI-driven documentation, and the future of software development.

• The team discusses the strangler pattern as a way to incrementally transition from legacy systems to modern platforms.

• Steve shares insights on how AI is being used for documentation, testing, and even code analysis.

• The group speculates on how AI-driven tools can improve developer efficiency and streamline migrations.

• They reflect on the importance of keeping up with evolving tech while maintaining a pragmatic approach to change.

This episode is packed with practical insights, real-world experiences, and candid discussions about the messy, challenging, and ultimately rewarding process of managing technical debt, cloud migration, and acquisitions. Whether you're a developer, architect, or IT leader, there's something valuable here for you!