In this episode, Amir welcomes back Dennis Mortensen — serial entrepreneur, former founder of x.ai, and now CEO of LaunchBrightly — for an unfiltered dive into the emotional highs and lows of entrepreneurship. From building and exiting companies to walking 25km across Manhattan for clarity, Dennis shares what it truly means to love the game of startups.

This isn’t your average "build and exit" story. It’s a deep conversation about why founders keep going, how they process failure, and what it really takes to stay in the arena. Whether you’re building your first SaaS product, pivoting after a setback, or just trying to keep your team motivated — this one’s for you.

🔑 Key Takeaways:

Startups as a 50-year fund: Entrepreneurship isn’t a one-shot game—it’s a lifelong portfolio of experiments.

The emotional resilience game: Success is less about the idea, more about your ability to handle the mental load.

Pivot with purpose: Pivoting is valid—only if you're still chasing the same pain point.

List of hate > list of ideas: Great startups often begin with a problem you just can’t stand.

Focus beats distraction: Dennis avoids advisory roles and side hustles to stay sharp on his core mission.

Reset rituals matter: Dennis’s 3-hour phone-free walks through Manhattan help him stay grounded and creative.

⏱️ Timestamped Highlights:

[00:00:00] – Catching up with Dennis and his new startup, LaunchBrightly

[00:02:00] – Automating product screenshots: why it matters more than you think

[00:05:00] – The “list of hate”: Dennis’s system for surfacing real startup ideas

[00:08:00] – Startups as skill-based games with mostly unknown rules

[00:10:00] – Life without predefined benchmarks — why it breaks most people

[00:14:00] – Why Dennis loves the zero-to-one chaos (and what that says about him)

[00:18:00] – Managing the founder’s emotional rollercoaster

[00:20:00] – How early fatherhood helped Dennis separate self-worth from business outcomes

[00:24:00] – The rise (and risk) of glorifying entrepreneurship on social media

[00:28:00] – Pivoting: what’s valid and what’s just survival-mode flailing

[00:32:00] – When a startup should die — and why that’s not failure

[00:33:00] – Dennis’s long walks: a no-tech ritual for clarity and sanity

[00:35:00] – How to connect with Dennis (and maybe join him on a Manhattan walk)

💬 Featured Quote:

“You should separate your self-worth from the sport you’re playing. I might not have won this race, but I’m as valuable today as I was yesterday.” — Dennis Mortensen