We commonly hear founders and leaders talk about scaling, exits, and wins. What doesn't get talked about as often are the messy inflection points—the pivots, the resistance, and the reinventions that shape who they become as leaders. This podcast interview pulls back the curtain on the parts we often don’t hear about in the founder/builder journey.

In this unfiltered live conversation, I’ll be having a candid discussion on these very topics with Chris Estreich.

Chris Estreich is a serial entrepreneur and technologist with over a decade of experience scaling innovative consumer platforms. He was the Co-Founder and CTO of Tophatter, a mobile-first ecommerce marketplace that grew to around $100 million in annual revenue and $300 million in GMV (gross merchandise volume). In his role as CTO, Chris provided the technical oversight for the product and engineering teams, guiding the development of Tophatter’s real-time auction platform that combined fast-paced shopping with marketplace efficiency.

Today, Chris is a Founding Engineer at Roo Code, where he is working on the cutting edge of agentic coding, building tools that help developers collaborate with AI to accelerate software creation.

Chris and I worked together for over 4 years at Tophatter, and I’m excited for him to share his thoughtful, insightful wisdom! Chris has lived through the highs and lows of scaling and personal inflection points. Known for his experimentation ethos and ability to find “fast moving water,” Chris is one of the best I know at pivoting quickly, taking fast action, and innovating smartly.

We’ll explore:

• Lessons from scaling from 0 to $100 million in annual revenue (and pivoting many times)

• How AI is reshaping the founder’s journey—and what advice Chris would give founders starting in AI today

• How introverted leaders can leverage your strengths and stay true to yourself

• Chris’s personal inflection point after Tophatter, and why he once thought coaching was a waste of time (and the surprising lessons from embracing it)
  

💡 For founders, CEOs, and executives navigating inflection points and identity shifts in an AI-forward world.

Find the full podcast here:

LinkedIn: https://www.linkedin.com/events/whatfoundersdon-ttalkabout-infl7362968134682636289/theater/

YouTube: https://www.youtube.com/live/V6UDm9O4PrM?si=M0XjigyVPjdsZSCp

and Apple Podcasts, Spotify, Amazon etc.

👉 To connect with Chris Estreich, follow him on LinkedIn or Twitter/X.

LinkedIn: https://www.linkedin.com/in/chrisestreich/

X/Twitter: @cte

And yes he really did get that username! Twitter early adopters in da house!!! He joined Twitter in April 2007; I joined May 2007.

👉To connect with me:

If you’re an executive or founder facing an important inflection point for you, I help people use their zone of genius to find clarity and confidence in strategically navigating this transition and journey. We can set up a 10-min clarity call to see if I can help you.

✅ You can book a call on my LinkedIn profile or message me on LinkedIn.

Thank you so much for joining us! Wishing you your best energy thriving in your zone of genius!! 🔥