What does a day in the life of a startup CTO really look like? Mo El Mahallawy, CTO and co-founder of Shepherd, shares the unfiltered journey from being engineer number one to leading a 50-person Series A company. He opens up about the hardest phases of building, what shifts as your company scales, and how he manages energy, priorities, and mental health along the way. This episode is a practical playbook for any founder, CTO, or tech leader navigating growth.

Key Takeaways

• The early days as a startup CTO are often the hardest—you're coding, recruiting, managing, and wearing every hat at once.

• Growth means trading code for vision: shifting from building features to setting direction and enabling your team.

• Time management is only half the battle—energy management and knowing when you do your best work is equally critical.

• Planning is a mental health strategy: when you control your roadmap, you avoid the burnout of constant reaction mode.

• Taking big swings matters more than just paying down tech debt—bets move the business forward.

Timestamped Highlights

02:41 – The origins of Shepherd and why Mo left Airbnb to build in insurance tech.

07:28 – What makes the early-stage CTO role one of the toughest in startups.

10:44 – Mo’s brutally honest description of those days: “like chewing glass.”

16:45 – How the CTO role evolves post-Series A and the challenges of stepping out of code.

20:44 – Why energy balance beats pure time management.

26:42 – Mo’s take on mental health and how planning became his best defense against fatigue.

A line worth remembering

“Your life is going to suck, and then it’s going to be great—but your job is to make this work.”

Pro Tips

• Use your strongest energy hours for high-leverage work, not busywork.

• Build your network early at iconic companies—you’ll rely on those relationships later.

• Don’t shy away from big bets; they create momentum that tech debt never will.

Call to Action

If you found Mo’s story valuable, share this episode with someone thinking about becoming a founder or CTO. And don’t forget to follow the show on your favorite podcast app so you never miss the next set of scaling playbooks.