Cliff Weitzman (Speechify): How to Learn Anything

Blake: This is a follow up episode to last week's conversation with Cliff Weitzman, founder, CEO of Speechify and his 28 rules for turning 28. It's an awesome video and he has an awesome YouTube channel, so I highly recommend you go check that out. And on that episode from last week, we talked about some of the more businessy rules, things that you can apply in the workplace. There was lots of other advice that kind of came out of that. But on today for the follow up conversation, I kind of wanted to dive into some of the more personal side of things and sort of personal growth side of things, as well. So there's a great rule that I think that we can unpack here and it's rule number 25 from your list. Which is to find the best people in the world at a skill and DM them. So what does this look like in real life and how do you practice this role?

Cliff Weitzman: Oh my gosh. So this is probably one of the things that's added the most value to my life, I'd say in the last decade. It started when I was in college and when I was young, I was very into parkour and tricking and gymnastics. And there are certain moves that like exist today that didn't exist before. Like people are now doing standing double back flips, that's insane or Websters or corks, whatever. And so you might not know someone in your local community that can do it, but someone could do it. And if you're really good and you want to learn it, like someone's got to teach you. And so what I started doing is every time I'd see a video on Instagram or YouTube, of someone doing a trick that I didn't know how to do, I'd DM'd them and I'd ask them to hop on a FaceTime with me. And I'd pick up in the gym and I would like have someone hold the phone and I would try the move and they'd critique me. And then later when I started doing well with Speechify, I'd find the best trickers I could find in the world. The people with the best flow, who could do moves that nobody else could do. And I DM them, I was like," Hey, could I pay you to coach me one on one? How much would I need to pay you per hour to do this?" And typically it's like$ 45. And what I'll do is I'll get a tripod with me and my phone and my AirPods with some like little things, so they don't fly out. And we'll do an hour session when I go to open gym and they'll coach me. And it keeps me accountable and it made me an incredibly better athlete than I was before. So I started with parkour and then I also make a lot of music. Interestingly enough, the best performing ad for Speechify right now is a rap song I wrote about my experience with dyslexia. And so what I did when I started to have this idea, even before that, is every time I'd see an up and coming artist, assume someone who's got like a hundred thousand followers, ish up all the way up to like two, three million. I would DM them on Instagram. And my favorite way of doing this is I'll send a voice memo and I'll be very specific, I'll be this one specific thing that you did reminds me of a mix between Lin- Manuel Miranda, Logic and Jon Bellion. I love your flow here. I want to write this. Would you be down to coach me doing this? And almost universally people respond," Oh, don't worry about paying me. Here's my number. Happy to do what with you." And so what I'll do like four Zoom sessions with them where I'll show them my work, they'll critique me, it just makes me so much better. But I do the same thing with entrepreneurs constantly. I love learning from operators and I'm literally all day, if I see someone doing something awesome, I message them. Either on Twitter, Instagram, LinkedIn, email, I get someone to introduce me and it'll be like," Hey, name. I think you're awesome because of X. I'm Cliff and I did Y. I have this specific question. Do you have time for like a quick Zoom?" And so I constantly do this and I highly recommend doing it yourself. One of my biggest desires in life is to have the most amazing friends. It happens to be that those people don't all live in San Francisco in The Bay area, so they have to come from all over the world.