Paul Orlando didn’t set out to become an entrepreneur.
Earlier in his career, he worked in corporate roles at AT&T and in management consulting, advising large Fortune 100 and Fortune 500 companies. Then a restructuring eliminated his entire practice, and instead of looking for another job like it, Paul started exploring what else he could build.
That eventually led to Chatfe, a startup that began as a way for strangers to have spoken conversations and later focused on connecting people recovering at home with others who understood what they were going through.
The experience changed the way Paul thought about entrepreneurship.
Today, he runs the startup incubator at USC, teaches entrepreneurship, writes about startups and business strategy, and has worked with hundreds of founders across different industries and countries.
Along the way, he’s learned that entrepreneurship isn’t about avoiding every mistake. Some mistakes are unavoidable. The real skill is recognizing patterns, adapting quickly, and understanding which decisions you can make better next time.
This conversation goes far beyond startups. We talk about:
Why Paul says he was essentially “forced” into entrepreneurship
What building his first startup taught him about figuring things out
The simple co-founder conversation that he says can prevent major problems later
What entrepreneurship can actually be taught and what may be harder to teach
Why “agency” and the ability to figure things out matter so much
How AI is changing what a solo founder can build
Why Paul made AI mandatory in his classrooms rather than banning it
What happened when he gave the same assignment before and after ChatGPT
Why he believes some things still need to be learned the hard way
What he learned building startup ecosystems in New York, Hong Kong, and Los Angeles
How culture can dramatically change the speed at which people build relationships and businesses
Why Hong Kong had incredible connectivity but a very different startup culture
Why being too early can be more dangerous than being too late
How to think about “Why Now?” without pretending you can predict the future
What founders should look for when deciding whether a market is actually ready
The things Paul believes won’t change even as technology does
Why economic resilience requires both a financial buffer and the ability to change direction
How having side projects can create optionality when your career changes unexpectedly
The 30-day “rejection therapy” challenge he gives his students
What more than 300 companies have taught him about the fundamentals of building a business
Why understanding customers, sales, and unit economics still matters—even in the age of AI
Whether Paul would ever become a founder again
Paul’s story is a reminder that careers rarely unfold according to plan.
Sometimes a layoff becomes a startup. A startup becomes a lesson.
And a lesson becomes a career helping other people build what comes next.
🎧 Listen to the episode
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A Line From the Conversation
“It is more dangerous to go in early because if the business model does not mean that we could build a financially sustainable business for years, then we are just losing money.”
Favorite Book
Erewhon by Samuel Butler
Paul’s recent pick is a particularly fitting one for this conversation: a utopian novel about a society that has deliberately prohibited certain technologies. It became a jumping-off point for a conversation about our relationship with technology, what happens when we intentionally stop technological progress, and how dependent we have already become on tools like AI.
In This Episode
In this conversation:
(00:00) Intro — Paul’s unconventional path into entrepreneurship
(02:00) From corporate jobs to becoming a founder
(03:39) Building Chat Faye and discovering the founder journey
(05:48) Can entrepreneurs avoid mistakes?
(07:26) The co-founder mistake that can be prevented
(10:34) What Paul learned from founders as an incubator leader
(12:51) Can entrepreneurship actually be taught?
(15:15) Agency, resilience & figuring things out
(17:05) Solo founders and what AI changes
(18:38) How Paul accidentally ended up teaching at USC
(22:05) Teaching entrepreneurship in the age of AI
(23:22) What happened when ChatGPT entered the classroom
(25:08) The AI experiment that changed what Paul saw in his students
(27:15) Learning the hard way in an AI world
(30:07) Reading old books, screens & staying curious
(33:26) Building startup ecosystems across New York, Hong Kong & LA
(36:14) Why Hong Kong moved at a different speed
(39:42) The challenges of building startups in Hong Kong
(45:15) Why being too early can be more dangerous than being too late
(47:16) Understanding “Why Now?”
(49:49) What do you do when you’re too early?
(53:32) What doesn’t change in a rapidly changing world?
(57:52) Economic resilience & surviving uncertainty
(01:01:22) Staying agile when your industry disappears
(01:04:15) The 30-day rejection therapy challenge
(01:06:40) What 300+ companies have taught Paul
(01:11:12) Would Paul become a founder again?
(01:12:05) Erewhon, technology & the future
(01:14:45) Final thoughts
The world is changing faster than ever.
But some things remain remarkably constant: understand your customer, build something people will pay for, learn continuously, and be willing to change direction when reality tells you to.
Paul’s journey is ultimately about that tension: knowing what to hold onto, knowing what to change, and learning how to keep moving when the path isn’t obvious.
If you’ve ever wondered whether you’re too early, too late, or simply on the wrong path, this conversation is for you.
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