I failed 22 times... then I built a $2.5B Company | Christina Cacioppo from Vanta

**Christina Cacioppo** (0:00)
And at the time, my email was Christina at usv.com. And it was like the right side, that usv.com is way more powerful than the left side. And now you're giving that up. And so what are you?

**Shaan Puri** (0:09)
You're betting on the left side.

**Christina Cacioppo** (0:10)
You're betting on the left side. And like, why would you do that? And like, what do you think will happen here?

**Shaan Puri** (0:24)
I don't know if you know this fun fact. Do you know what you, Katy Perry and Serena Williams have in common?

**Christina Cacioppo** (0:29)
I've got nothing.

**Shaan Puri** (0:31)
You're all on Forbes' self-made women's list.

**Christina Cacioppo** (0:34)
I hate that list.

**Shaan Puri** (0:34)
You are ahead of them. Isn't that kind of amazing?

**Christina Cacioppo** (0:36)
I would have preferred that list never existed.

**Shaan Puri** (0:39)
You have that Midwest modesty.

**Christina Cacioppo** (0:41)
Yes. Nothing good will come from that list. Yeah.

**Shaan Puri** (0:44)
Those lists are made for the wrong type of people. Yes.

**Christina Cacioppo** (0:49)
Or jail time later or something. Trevor will laugh at that. I was never on 30 Under 30, and I'm deeply glad about that now.

**Shaan Puri** (0:55)
Yeah. That turned out to be an anti-signal. When I was thinking about this episode, the way I think about it is where you are today is where a lot of people want to be. You have a company that's working, it's got a cool startup name, it's got a cool office in San Francisco. Last valuation, I believe 2.4 or 5 billion, but who's counting? Today, you're at where a lot of people want to be. But if we rewind the tape, to me when I looked at your story, I think the through line for this is not counting yourself out. So I'm going to put that out there. That might be true or might not be true. But the basics of it is you had a good job and you quit to try something new, to try to make it on your own, which a lot of people want to do, but they don't take the leap. You took the leap and it's not like it hit right away and you created Vanta and you created this multi-billion dollar company right off the bat. You did like 35 things wrong or 35 projects that went nowhere. And I love that because I spent eight years of my life banging my head against the wall with failure after failure after failure. Each time believing this is the time. Let's start where you have a good job.

**Christina Cacioppo** (2:00)
Yeah.

**Shaan Puri** (2:01)
You have the job at USB, which I think you kind of hustled your way into.

**Christina Cacioppo** (2:05)
I was a stumble hustled.

**Shaan Puri** (2:07)
Okay.

**Christina Cacioppo** (2:07)
I didn't like a hustle. They announced that job. They do all their jobs on the Internet and said, hey, fill out this form if you want this job, send us some links to your web presence. I literally sent them three links to my web presence and didn't e-mail anyone who knew them. Turned out I knew people from school who didn't pull anything, just sent them links and put them in a form and was like, well, now I'll go back to making slides.

**Shaan Puri** (2:34)
What kind of links?

**Christina Cacioppo** (2:36)
It was Twitter, Flickr, through the era of this, and I had started a design blog a couple months before, and I lived in Berlin because I wanted to be like a designer who lives in Berlin, and those people seemed to have a design blog, so I started one, and that was it. They hired me, which is crazy.

**Shaan Puri** (2:59)
All right. Let's take a quick break because I want to talk to you about some new stuff that HubSpot has. Now, they let me freestyle this ad here, so I'm going to actually tell you what I think is interesting. So they have this thing called the Fall Spotlight, showing all the new features that they released in the last few months, and the ones that stood out to me were Breeze Intelligence. I don't know if you've seen this, but if you're in HubSpot and you have, let's say, a customer there, you can just basically add intelligence to that customer, the estimated revenue for that company, how many employees it has, maybe their email address or their location, if they've ever visited your page or not. And so you can enrich all of your data automatically with one click using this thing called Breeze Intelligence. They actually acquired a really cool company called Clearbit and it's become Breeze, which is great because now it's built in. I always hated using two different tools to try to do this. Now it's all in one place. And so all the data you had about your customers now just got smarter. So check it out. You can actually see all the stuff they released. It's a really cool website. Go to hubspot.com/spotlight to see them all and get the demos yourself. Back to this episode.