Uploaded December 2025 | Updated September 2026, 2 hours ago
Entrepreneurship looks like freedom from the outside. Build what you want, work when you want, travel whenever. And yes, that part is real. But there’s also a dark side that people rarely talk about.
My friend @ShawhinTalebi felt it right after transitioning from his technical role at Toyota into full-time entrepreneurship. The freedom is incredible… but the loneliness hits harder than expected. The deeper you go, the fewer people truly relate to your goals, your problems, or the mix of technical and business decisions you now live with every day.
As a technical founder, it’s even more intense. You no longer have that “army of engineers” to bounce ideas with. Your old friends might not get the technical side, and very few understand the business side. You become this strange in-between alien navigating both worlds alone.
It’s not talked about enough, and if you go down this path, you need to know it’s part of the journey. The freedom is amazing, but it comes with a cost.
I’m Louis-François, PhD dropout, now CTO & co-founder at Towards AI. Follow me for tomorrow’s no-BS AI roundup 🚀
#entrepreneurship #founderlife #startuplife
Entrepreneurship looks like freedom from the outside. Build what you want, work when you want, travel whenever. And yes, that part is real. But there’s also a dark side that people rarely talk about.
My friend @ShawhinTalebi felt it right after transitioning from his technical role at Toyota into full-time entrepreneurship. The freedom is incredible… but the loneliness hits harder than expected. The deeper you go, the fewer people truly relate to your goals, your problems, or the mix of technical and business decisions you now live with every day.
As a technical founder, it’s even more intense. You no longer have that “army of engineers” to bounce ideas with. Your old friends might not get the technical side, and very few understand the business side. You become this strange in-between alien navigating both worlds alone.
It’s not talked about enough, and if you go down this path, you need to know it’s part of the journey. The freedom is amazing, but it comes with a cost.
I’m Louis-François, PhD dropout, now CTO & co-founder at Towards AI. Follow me for tomorrow’s no-BS AI roundup 🚀
#entrepreneurship #founderlife #startuplife
