This content was created by Tim Draper. This content was uploaded by Tim Draper. This is a YouTube talk titled "Putting in the hours | Jason Calacanis" (posted Aug 30, 2017) featuring Jason Calacanis in a live Q&A/interview-style session with a moderator (labeled here as "Speaker B"). Calacanis shares anecdotes about his early angel investing, trading services for equity, mentorship, and practical hustle/career advice for founders, designers, and aspiring investors, and briefly promotes his book. The excerpt appears to be a motivational, instructional talk given to an audience (mentions Draper University and a summer cohort).
Chapters
And I wanted to share a little bit of that story of how I did it.
Right.
And I hope other people read it, deploy it, and become wealthy. That is sincerely and truly my goal. I don't need to sell books. The book is super cheap. It's $10 for an Audible book or $20. Books are the greatest value in the world. And so I just sincerely hope people read it and get some value from it, and some number of them either are able to raise money for their startup easier Or learn to be more successful from it, or learn to be angel investors and learn the craft. And you can do it without money.
Right.
My first gigs as an angel investor— I'm using air quotes for people listening— was as an advisor. I traded my skill in PR and marketing to a company called Zero Degrees, which was a business networking before LinkedIn. I made $16,000 when it sold as An advisor.
Right.
Then I went on the board of Savings.com and helped them with social media and blogging. And when they sold, I made $125,000. And my wife was like— she was here a minute ago— she's like, you're making $100,000 a year and you just did 12 board meetings over 3 years and got $125,000. That's like for 20 hours of work. It's like half a week of work. I was like, well, it's kind of more. It was like double that. So 40 hours of work.
Yeah.
She goes, be on more boards, be more— be an advisor to more companies. You can easily trade your skills to be an advisor. And then I was on the board of Dyn, the DNS routing company, and they sold to Oracle and I made $400,000 or $500,000 for being on the board of that company. So it just went up, up, up, up. And there were 2 or 3 that wound up being zero. But that's how I got some of my first cheddar to kind of put to work. If you're sitting here and you're a developer or a designer or a sales executive where you have some skills, you could trade those with a startup. So you can go to 5 startups if you're a designer and say, I look at— and you just watch them on AngelList. And if you see the ones I'm investing in on Crunchbase or Cyan Bannister or Kevin Rose or Sequoia, whoever it is like you think is a good investor, Y Combinator, whatever it is, and they raised $1 million or $500,000, you say—
I'm in.
Hi, I'm a designer. I saw your website, I saw your logo. I thought it was solid but not great. I designed a great one for you. It took me 10 hours.
Right.
I would like to do your design work for the next year. I'd like to give you this as a free gift. Maybe you can give me credit for it, or I could put it on my LinkedIn page, but I'd like to give you this for free. But I would like to trade you $25,000 a year in my design services in exchange for $25,000 in equity at your first round At your recent round's valuation. If you do that with 20 people, you'll get 5 of them.
Right.
This is the kind of hustle that could make you rich. There were people who did this with Uber and Airbnb. They traded services for equity. Most times it will be a zero, but you only need to be right once, as my good friend Mark Cuban told me. And I've been right 7 times. That's why I got to write the book, right? If you— I'm not the smartest kid in the class. I was a 71-year, 3-year average, but I was the most dogged.
Right.
In my adult life, I was the most dogged. After my family lost all their money and I was on my own, I had to be dogged. If you're dogged and you have those skills and you just hustle and you just put out help for people, you're a sales executive. You go tell somebody who's starting an enterprise company, I see you have 3 sales jobs open. I rewrote the job descriptions because what you're actually looking for is an SDR, and here's the skills they need, and I put it in bullet points for you. And for your senior execs, I don't recommend hiring a senior exec. I would hire 3 junior-level people who you think have potential, and I would get them equity, and I wouldn't put a director in yet. I would see which one of those could maybe move up to director position and be more efficient for you. And the directors don't do any direct selling, so what you're really looking for is somebody who's an up-and-comer. If I got that email when I was starting a company, I'd be like, who are you and when can we have coffee? Like, that's just a snap yes, right?
Right.
But people don't hustle. And that's why they— and they don't take risk. You have to be willing to take risk if you want to have an outsized return. You have to be willing to hustle and you have to be willing to put in more effort.
Right.
So look to the left and look to the right when you're sitting here in Draper University. If somebody is coming in before you and that same person is staying in after you, they're going to beat you in all likelihood. When I was starting my career, I looked to the left, I looked to the right. I said, I'm coming in before my boss, and I would never leave my office until my boss left. You know what happened? My boss went by my desk 3 times, and on the 3rd time, this was when I was 21 years old, he said, what are you doing here? And I looked on my desk, and I just didn't wanna leave before him, and I picked up the first book I saw, it was Novell Networking, and I said, I'm trying to get my Novell, I'm just getting, brushing up on Novell Networking. It wasn't true, I was just sitting there, like, doing some work, but I—
Mm-hmm.
I said, I'm just trying to be better at Novell networking. He's like, oh, that's great. Did you eat dinner yet? No, I didn't eat dinner. He goes, you want to get dinner with me? I said, sure. This is my boss's boss, Mike Savino. And I went around the corner in Manhattan with him. I had dinner. Now I'm having dinner with my boss's boss. We became lifelong friends. He got me my next 2 or 3 jobs. Now he's a venture partner with my firm, so he brings me deals.
Right.
This is 25 years later or 20, 20-some-odd years later. He became my mentor. He taught me everything I know about business, or almost everything I know, how to be a hustler, how to close deals, all because I refused to leave the office until he did.
Right.
That's what's missing. And that's why if you're listening to this and you're not successful yet, you're probably not refining your skills enough and you're probably not working hard enough. I hate to be the one to bring it up, but you got to take a deep look in the mirror and ask yourself, am I adding skills every year? What do I know this year that I didn't know last year? Who has learned a tangible, awesome skill in the past year? Raise your hand and be honest. Who learned a tangible— okay, it's about half the audience. For the other half, let's get moving. Let's get to work. Let's take the work seriously.
Right.
You have to do the work. Nothing is promised to you. Nothing is given to you. And it's a massively competitive world. If you got a participation trophy, They lie to you. You get ungats, nothing, nada, and zero for showing up.
Right.
You're entitled to zero for showing up. You have to do the work. And man, I meet with 20 founders a week, and half of the time I'm just so inspired, and the other half of the time I'm just shaking my head. This person is literally walking into a freeway. They have no idea. They got blinders on and they're just walking in front of a train. Like, I have no idea how hard this is. They have no skills, they have no hustle, and they expect, oh, I'm going to start working when you give me an investment.
What?
No investor wants to invest in somebody who's going to start the work when they get a check. We want to feel like the train's leaving the station. You're— you've got a rocket ship, you're getting work done. With or without our dollars.
Right. Thank you. No, that's amazing. And so guys, get to work. Come on. It actually was very easy on my part. You answered almost everything without me asking. So thank you so much for that.
I apologize. I'm fired up.
No, no.
I'm really excited.
I love it. Guys, you all are going to get a copy of the book and—
Are they really?
Yeah.
Do they all work here, or do they all work out of here?
They all actually— so half of them actually are going through our summer cohort.
I'm gonna come back because I live in Hillsborough, right up the block. I'm gonna come back one day and sign them all. So after you get them, pick a day and I'll come by for a burger and autograph every one.
Awesome. Yeah, that would be great.
It felt so good today. I was at PayPal and they had like copies of the book, and I got to sign like 70 copies of the book, and I just I thought, I like being an author.
We're getting early copies, so we've been working with your publisher to get them earlier than everybody else does, so that would be even better.
