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EPISODE · Oct 9, 2025 · 50 MIN

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

from EGGS! The Podcast · host Ryan Roghaar and Michael Smith

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! Mike "DJ Ontic": Shows and info: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠djontic.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ @djontic on twitter Ryan Roghaar: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠rogha.ar

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

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