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October 9, 2025 50 mins

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.


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


Credits:

Hosted by Ryan Roghaar

Produced by Ryan Roghaar

Theme music: "Perfect Day" by OPM 

 

The Eggs Podcast Spotify playlist:

bit.ly/eggstunes


The Plugs:

The Show: eggscast.com

@eggshow on X and Instagram


On iTunes: itun.es/i6dX3pCOn

Stitcher: bit.ly/eggs_on_stitcher

Also available on Google Play Music!


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Ryan Roghaar:

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