When everything works, you learn the wrong lessons artwork

When everything works, you learn the wrong lessons

My First Million

January 15, 2026

Get our Resource Vault - a curated collection of pro-level business resources: https://clickhubspot.com/ebh Episode 785:  Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talks to Nick Huber ( https://x.com/sweatystartup ) about the biggest bet he ever made and the mistakes he learned the hard way.
**SPEAKER_1** (0:00)
All right, look, on YouTube, everybody talks about how they're crushing it. Every business podcast, every business influencer is talking about how great everything is going. But on today's podcast, my buddy Nick is coming on, and he's doing the opposite. He's talking about a bunch of the big mistakes he's made. He's eating humble pie publicly on the podcast today and talking about some of the things he's learned from it. So I want you to tune in to this episode. He's talking about how he made the biggest acquisition of his life when he bought somewhere.com, how he might have screwed up certain things and how he's trying to recover from those. It's another side to Nick. If you know Nick, he's a popular guy online, but you don't always get to see the humble side. And so I think it's a great episode with Nick.

**SPEAKER_2** (0:38)
Enjoy. All right, what's up?

**SPEAKER_1** (0:48)
We got Nick Huber here, friend of the pod. Nick, what's up, man?

**SPEAKER_3** (0:51)
Shaan, thanks for having me. It's been a long time.

**SPEAKER_1** (0:53)
Dude, you've wrote something. So we have every guest do a little prep doc of like, hey, what are some things on your mind, stories, ideas that you want to share? And you wrote one that I think is very interesting to people who've been following Nick Huber. So you built up this personality online of being confident, borderline cocky. You have strong opinions. You are not afraid to piss some people off. And you said this in the document. You said, I have been humbled of my cocky attitude in my thirties. Is this a, do we have a heel turn? What's the face turn like in wrestling where the bad guy becomes good? What's going on?

**SPEAKER_3** (1:30)
Yeah, man, I think the last five years in business, I mean, five years ago, you guys had me on the pod. I felt like I knew everything, man. Like, and I think it was that irrational confidence early in my career that I wouldn't trade for anything because I think it led to a lot of success and me putting myself out there. But yeah, man, like you just realize that business is hard. Business is really hard. So it's not the same as it was 2024, 2025, or not the same as 2022, 2023 for any entrepreneur I know.

**SPEAKER_1** (1:57)
So give me an example of how Nick, what Nick was thinking then versus Nick thinking now, because there's this great phrase, everyone's a genius in a bull market. I think part of what you're going to talk about is like back in 2020, 2021, 2019, like during that era, it felt like you could do no wrong. But like give me a, Nick back then, he was thinking XYZ about himself or the world. And now what is Nick thinking?

**SPEAKER_3** (2:20)
I thought business was easy. I thought building executive teams was easy. I thought customers just came. I thought I could do no wrong because I had this personal brand, started all these companies, started 10 plus companies over a three year period.

**SPEAKER_1** (2:31)
Might as touch.

**SPEAKER_3** (2:32)
Four of them have been shut down. So yeah, it's not all roses.

**SPEAKER_1** (2:37)
It's not all roses. But you are, I guess older and wiser now, and it's sure something shut down, but other things you've sort of doubled down on and have started to work. What do you think caused that? Was it just market kicking your ass a little bit in certain areas that sort of made you reassess? Were you wrong about a specific thing?

**SPEAKER_3** (2:56)
I thought with a personal brand that's strong enough, you could get into an agency business of any kind and go to the moon. Whether or not you do a couple of things right, a couple of things wrong, whatever. And then yeah, the algorithm changed, like the business got a little harder. People started really watching how they're spending money. So I just think it's harder now than it was, man. Like I know a lot of people who are making less money now than they were three years ago.

**SPEAKER_1** (3:19)
Right, right. OK, I want to jump around into some of your new ideas. So things you're feeling, thinking right now. So, you know, you mentioned being sort of humbled and you mentioned your portfolio going from how many companies did you have kind of like at your peak and how many do you have?

**SPEAKER_3** (3:34)
Eleven. Yeah, I started eleven companies from, you know, 2016 was my first, you know.

**SPEAKER_1** (3:40)
You were like, I'm going to do an SEO company. I got a storage company. I got a, what else did you have? You had a bunch of other stuff.

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