Presented by RŌG Health

Eggs 435: Design. Deploy. Develop yourself with Caleb Mellas

EPISODE 435 • OCTOBER 9, 2025 • 50 MIN

Episode Summary

In this episode, we explore the journey of Caleb Mellas, a senior software engineer and tech lead at Olo Inc. Caleb shares his transition from landscaping to software engineering, the challenges of freelancing, and the impact of imposter syndrome on his career. He discusses his experiences at Wisely, the acquisition by Olo, and his recent shift into engineering management. Throughout the conversation, Caleb emphasizes the importance of continuous learning, building a strong professional network, and the value of soft skills in advancing one's career.


Key Takeaways

  • Imposter syndrome can be a sign of growth.
  • Starting as a landscaper, Caleb found his passion in tech.
  • Freelancing taught him valuable lessons about income stability.
  • Transitioning to full-time work brought new challenges.
  • Building a strong network is crucial for career growth.
  • Continuous learning is essential in the tech industry.
  • The acquisition of Wisely led to new opportunities at Olo.
  • Engineering management requires a different skill set than coding.
  • Soft skills are vital for career advancement.
  • Sharing experiences on LinkedIn can help others in their careers.

Chapters

00:00 Introduction to Caleb Mellis and His Journey
03:00 Transitioning from Landscaping to Software Engineering
05:55 Freelancing and Overcoming Imposter Syndrome
09:07 Navigating the Feast and Famine Cycle in Freelancing
12:05 From Freelance to Full-Time: The Shift in Mindset
14:59 Learning New Technologies and Overcoming Challenges
17:52 The Importance of Consistent Learning and Growth
21:12 Interviewing Strategies and Standing Out in the Tech Industry
24:39 Going Above and Beyond in Job Applications
27:15 The Importance of Relationship Development in Interviews
29:09 Navigating Early Career Challenges
32:41 Innovative Solutions in Restaurant Technology
35:01 Developing a Growth Mindset
37:31 Experiencing Company Acquisition
40:28 Transitioning from Engineer to Manager
44:51 Balancing Technical Skills and Leadership
47:16 Building a Professional Network on LinkedIn

Show Credits

Guest: Caleb Mellas

Credits:

Hosted by Ryan Roghaar

Produced by Ryan Roghaar

Theme music: "Perfect Day" by OPM 

 

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