139. How to Angel Invest like the Best, Part 2 (Jason Calacanis)

**SPEAKER_1** (0:03)
Welcome to the podcast about Investing in Startups, where existing investors can learn how to get the best deal possible. And those that have never before invested in startups can learn the keys to success from the venture experts.
Your host is Nick Moran, and this is The Full Ratchet.

**Nick Moran** (0:22)
Welcome back for part two of the discussion with Jason Calacanis. The response to part one has been overwhelmingly positive. I can't remember the last time I received so many emails about an episode. Clearly it struck a nerve with many of you, so I'm happy to release part two today. For this installment, I did not have time to include the usual tip of the week. However, I did include five takeaways instead of the usual three. There were numerous valuable insights from Jason, hence the additional takeaways that we'll recap at the end of the episode. Quickly, I wanted to congratulate David Rabi and the team at Tovala for officially launching their product. It's a smart oven and companion meal service. As one of our investments, we've featured Tovala on the program here before, and David actually made an appearance very recently on Jason's This Week in Startups podcast. It was a fantastic episode and I'd encourage everyone to check it out. Tovala has a limited release of 2,000 ovens available right now, and I hear they're going fast. My wife and I have been using the service for months now, and we've been blown away by the food quality. The meals are far better than anything we've had from Blue Apron, and they're certainly better than the unhealthy takeout options nearby. With the new addition to our family, and my wife's three-month maternity leave, we've even increased our meal plan from six meals per week to nine. I never imagined my super picky wife would be loving the food so much.
She now wants to even have it as an option for lunch, as she's been busy with the baby. Amazing.
So, once again, congrats to the team. You've created a better lifestyle for my family. We're spending more quality time together and eating much more healthy, delicious food. I look forward to thanking you guys in person soon. Okay, as for the interview with Jason, in part two, we cover his thoughts on the original Sequoia Scout program and the many similar programs today. How he does such high volume of investments when he insists on spending hours with every startup founder that pitches.
If he's really investing in the angel round, when it seems that he's been targeting post seed. His response to those who claim that VCs get access to all the best deals. And finally, his strategy with the Syndicate and the types of deals he's looking for. Here's part two of the interview with Jason Calacanis.
So you did mention Sequoia. And I believe you were the first Scout for Sequoia years ago.
And now it seems like all the big firms have their own sort of Scout or investment programs and some of the earlier stage funds or investors. You know, what are your thoughts on this?

**Jason Calacanis** (3:16)
It's obviously a program that works.
You know, when Rulof Kota came up with it, he asked me for my opinion on it. And he's like, we give you the money, we split the returns 50-50. I said, what's the catch? He's like, oh, you have to fill out a deal memo. I was like, F that. I don't want to fill out any paperwork. I'll just make this one page. And it just says what you think, why you think this will work. And I was like, I don't know if I want to fill out one page.
And I was like, pretty stupid on my part. And in the book, actually, I talk about the value of writing deal memos and writing pieces, right?

**Nick Moran** (3:47)
So you do it for the syndicate investments still.

**Jason Calacanis** (3:49)
I do it for the syndicate investments. I write public blog posts, why we invested $378,000 in com.com when everybody told me that was going to be a failed investment. And I'll be putting that back in people's faces shortly. I cannot wait for that day. But it's, yeah, I learned a lot from that program and the association and I think it's wise that other venture firms have scouts out there because a venture firm putting $500 million to work does not have the ability to write $50,000 checks.
I mean, just think about the number of $50,000 checks they'd have to write to deploy 500 million or even 100 million. It's impossible.
You know, I'm writing $100,000 checks right now and I'm going to try to deploy 200 of them in the next three or four years. That's a lot of check writing. That's a lot of babies to have some-