This Week in Startups - Ask an Angel! Startup funding overview, investor red flags, negotiating early-stage terms | E1694

Episode Date: March 10, 2023

Zach Coelius is BACK with Jason to take questions from founders and investors! They cover investing on Zoom post-COVID (6:07), diligence red flags (13:13), investor red flags (27:32), building relatio...nships prior to fundraising (48:59), and more! (0:00) Jason Kicks off the show (1:21) Managing time as an angel (6:07) Moving to zoom instead of the room (9:50) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (10:54) Servicing new deals vs. existing ones (13:13) Red flags to look for in a syndicate startup deal (20:18) Coda - The All-in-one doc for teams, sign up for free at https://coda.io/twist (21:47) Your options when there is no path to profitability (27:32) Red flags when courting angel investors (41:10) Contra - Get $500 off your first hire at https://contra.com/twist (42:35) Assumptions that have evolved (45:23) Recent learnings in the past few years (48:59) Building genuine relationships with investors (53:40) Difficulties in startups (57:37) Negotiating terms on deals FOLLOW Zach: https://twitter.com/zachcoelius FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Transcript
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Starting point is 00:00:00 All right, everybody. The number one, most frequent guests on the program is back today. Zach Collius is here for Ask an Angel. We did it live on YouTube and we got a ton of great questions, raising money on Zoom post-COVID, red flags to consider when reviewing syndicate and startup deals as an investor and concepts that early in our careers we believed in, but maybe we think differently about now how you can form relationship with VCs before you build your startup. and investor red flags.
Starting point is 00:00:31 What kind of people should you look out for us, a startup founder that you don't want on your cap table? And so much more. Stick with us. It's going to be a great show. Zach is amazing. This weekend startups is brought to you by Vanta. Compliance and security shouldn't be a deal breaker for startups to win new business.
Starting point is 00:00:47 Vanta makes it easy for companies to get a sock to report fast. Twist listeners can get $1,000 off for a limited time at vanta.com slash twist. Coda. Coda is the all in one. and doc for teams. If you've got a stack of niche workflow tools or you're buried in docks and spreadsheets, Cota is the doc that brings it all together. Startups can sign up for free at coda.io slash twist and Contra. Contra is a commission-free marketplace for freelancers and independent creators. Get $500 off your first hire at contra.com slash twist.
Starting point is 00:01:21 Okay, everybody, we're live on the YouTube right now with Ask an Angel. This is a series that I've been doing for years with my friend Zach Colius. Who's Zach Collius? He's a serial entrepreneur. He got into Angel investing and early stage investing at the same time I did
Starting point is 00:01:34 just about 10 years ago, correct, Zach? Yeah, yeah, 2015. Spring 15. He runs Coelius Capital. That's his last name, C-O-E-L-U-S. You can follow him, Zach Collius on Twitter. And, you know, as far as investors go,
Starting point is 00:01:51 I have a sign behind me that says, do the work. That sign's there for me. Not for y'all, but if you benefit from it, I'm super happy. But people who do the work in our industry tend to gravitate towards each other. Zach and I have a great collaboration here
Starting point is 00:02:04 because we both do the work. And man, it's a lot of work. What do you, I'm going to start with, welcome back for your 17, 18, 19, 20, whatever. Who knows? I stopped counting. But I think about a pod more than anybody now. Cool.
Starting point is 00:02:20 So what is, if you were to draw up high chart, This is my question And then we'll get to the audience's questions here If you were to draw a pie chart In the life of an angel An early stage investor In their You know getting you know
Starting point is 00:02:37 Towards the end of their first decade Of investing Now you've got a book of business You've got existing startups You got LPs There's a lot going on here Yeah yeah yeah And some of the major pie slices
Starting point is 00:02:47 Would be meeting new founders Servicing existing investors And then doing the crazy Meshuggets associated with managing LPs and administration. Yeah. Just those three pie charts. How do you break it up today?
Starting point is 00:03:02 Rough percentages. I would add a fourth one, which is being a free, fun, individual, enjoying life. So when I was a founder, you know, my last company, we started in 2005 and ran that for over a decade. And it was nonstop.
Starting point is 00:03:22 It was 24 hours a day. it was your entire life and soul and every ounce of your being was going into trying to making this work. And there was never a moment to be like, I'm not 100%. And I think one of my favorite things about being an investor is that there's a real 80-20 rule in this business, at least that I found in my experience, where 20% of my time provides 80% of the value. And the rest of it has this very fast depreciating curve. And so, like, you know, the best founders are people I know or they come from people I know. And, you know, and that's a really small slice of my time, but it's where all the value is.
Starting point is 00:04:03 And so what I found really quickly in this job is that like, I can spend my time doing the work. And then there's all this other time that I could go enjoy life. And I was like, oh, my God, I'm going to do that because I spent a decade getting my head bashed in being a founder. And God, it's so good. And I'm just trying to constantly do that and keep that. that sort of like, I wouldn't say balance. It's not balance.
Starting point is 00:04:26 It's more of just like joy in my life. Got it. Like the opportunity to go explore the world. Like I'm trying to go to every country in the world. And that's like, that takes time. And it's awesome. And it's like super cool.
Starting point is 00:04:38 And so like stuff like that. How many countries have you been to? How many continents have you been to? How you keep in Antarctica yet? But I've been to 90 something countries. Wow. And in a good year, I'll get 10 new ones. You know, we'll see.
Starting point is 00:04:50 Wow. And you've remote work there. Yeah, yeah. You can do this job anywhere, right? Yeah. That's another great thing about it. The job has changed significantly. Everything used to be in the room. Yeah.
Starting point is 00:05:02 To take a meeting and then founders would fly in to see you. So maybe you're obligated to take them to lunch. Yeah. Because just doing a half hour meeting with them would be a jerk move. So now you're at three or four hours. And basically it's the whole day if somebody flies in to see or at least half the day. And you still feel like a jerk for only spending half a day with them if they flew in from New York or L.A. or whatever. So this Zoom thing has changed everything.
Starting point is 00:05:24 You can do a lot more meetings. You'll be a lot more efficient in board meetings. I have an in-person board meeting today. But yeah, the board meetings going virtual has been a godsend as well. Oh, yeah. I mean, I don't sit on boards. Otherwise, it would really change a lot of parts of my business. But yeah, no, Zoom and Zoom.
Starting point is 00:05:43 I was really worried early on when we first started investing via Zoom in the beginning of COVID. I was like, oh, how's this going to work? But so far, I mean. the performance of that portfolio has been is very good. What do you attribute that fact to? So Zoom, doing meetings on Zoom as opposed to in person, is as good or better than it was pre-COVID,
Starting point is 00:06:05 and people are sticking with that model. What do you attribute better selecting and better picking and more efficiency? What is causing the lift from moving to Zoom instead of the room? I think one thing that's happening is that the founders are able, because they don't have to go in person to Sand Hill. They don't have to show up and run around San Francisco to meet with people in person. They can have more meetings. And as a result, they get to basically more rapidly kind of sort through who makes sense and who doesn't. And as an investor on the other side, we get to do the same thing.
Starting point is 00:06:45 Like, I get to see a lot of pitches like and decide. which ones I want to take. And I think the, so the volume of deal flow that I'm getting, I think is up as like is significantly up. And as someone who for me, I really specialize in trying to find weird stuff. Like I like stuff that like nobody else likes and that like,
Starting point is 00:07:04 and so the broader my aperture, the higher the opportunity of finding something that is like, is really kind of like going to fit my style. And so that that seems to be a big driver. The other thing is that like, I actually don't think that my in-person is substantially better than my Zoom read on a person. So, like, think about a poker read.
Starting point is 00:07:28 Like, when I'm sitting with somebody in Zoom and I'm sitting with somebody in person, I don't think it's, like, order of magnitude difference. I do think, like, phone call versus Zoom, big difference. Like, or phone call versus, like, meeting in person, big difference. But Zoom, I'm, it's not clear yet, but I think I'm pretty close. Like, it's... Yeah.
Starting point is 00:07:45 My theory on this is, is that the in-room stuff creates a lot of obligation. It creates a lot of reciprocation effect. Okay, we've been in the same room. So now there's like a relationship being built. Yeah. And then that can drive people to make decisions based on the vibe, the relationship, which founders know.
Starting point is 00:08:06 Yeah. And investors know. So investors really want to get in the room with a hot deal and try to build relationship fabric. They want to go on a hike with you. They want to have dinner with you if it's a hot deal. Yeah. Founders know this as well.
Starting point is 00:08:16 that's why they want to get in the room with you, or previously did, because they want to use that time to build a relationship and have it be harder for you to say no, ultimately. Okay, great, those are sales techniques. We get it. Person comes on the lot. They want you to spend a long time on the lot,
Starting point is 00:08:31 and then the chance of you buying a cargo up. Okay, this is just known. So then if you move to Zoom, and people become a little bit more dispassionate, a little bit more objective, in terms of picking their investor and picking the founder to back, And like you're saying, you can see three times as many, four times as many people on both sides of the table.
Starting point is 00:08:52 What that means ultimately is you find better matches for investors and companies and products. And then we have more time to do diligence, look at the numbers, talk to customers, and do things that are less performative, less relationship building in the room. So then what's lost is relationship fabric being built for when things go wrong. So I have just instituted in our firm since we're so good at ripping through tons of introductory meetings and founders are so good at it now. Well, after we make the investment,
Starting point is 00:09:24 we realize we haven't spent a lot of time with these founders in a room. So do we have a deep relationship fabric? We don't. And so now I'm like, okay, more Zooms post-investment, more breaking bread, having a meal. So I'm just starting to think about that a lot more.
Starting point is 00:09:39 And I think people should so that when things get hard, you got that relationship fabric to fall back on. So it's, uh, it's, it's really interesting how things have changed. Listen, it's 2023. The macro picture is a little shaky. It's uneasy out there and tech is getting hit super hard. As such, you cannot afford to lose sales for silly stuff like not having your sock two right now. If you are unsure about your sock two, you need to check out Vanta. Vanta makes it incredibly easy to get and renew your sock two. On average Vanta customers are sock two compliant in
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Starting point is 00:10:52 for $1,000 off your sock tube. So servicing new deals versus existing deals. Yeah. Percentage of time. Yeah, yeah, yeah, I'm actually your original questions. So I probably spend
Starting point is 00:11:05 third, no more, probably 40 to 50% of my time looking at new stuff. Right. And then I'm probably spending 30 to 40% of my time helping existing companies. And thankfully, the admin stuff is not too bad.
Starting point is 00:11:22 It's all been attracted now. You have service providers like Carta, like AngelLess. They've just taken all that back office and made it into a product. So you don't need to. I hired someone who's been amazing to like help me on my audit work. Right. And oh God, we're doing the audit this year. And compared to last year, it's like night and day.
Starting point is 00:11:42 She's a pro. And it's like, it's like, watch it pro at work. You're like, damn, that's good. They've done it before. Yeah, yeah. Explain what the audit is for venture capitalists, why this is painful for us. And what the purpose of, an audit of your portfolio is every year. Yeah.
Starting point is 00:12:00 So, I mean, I have LPs who give me their money to invest. And so every year we go through a process where we hire a effectively an accounting firm to go through and they look at all the different companies, all the positions in the portfolio, where they marked. They basically, they'll Google them all and they'll be like, hey, this firm announced the fundraise and we haven't changed the mark why. Or this firm did this and that so then we go through and we basically like answer all their questions, provide all the supporting documentation and effectively sort of say that the portfolio is what we said it was and that it's worth what we said it was and that they, you know, hopefully there's no bad shit going on. And so the LPs use that
Starting point is 00:12:43 to basically feel comfortable with the fact that we're doing our job and that when we call them for more capital, that, you know, they should give it to us. Fantastic, yeah. And so it's an arduous process. And then you have to get in touch with every single founder. You've got to get all this information. And, you know, it's important for founders to keep their investors up to date. And the audit is like the ultimate backstop of that.
Starting point is 00:13:03 We have no choice but to get information from you. So founders, please. When we ask you for that information, make our lives easier. Please. All right. Here come to the questions. First question comes from almost. Omar asks, when reviewing an Angelus syndicate startup investment deal, what should we consider as red flags?
Starting point is 00:13:20 Okay. So when you're being invited to a syndicate, what are the red flags you should look for? Okay. Now, if it's one of Zach's deals and it goes out to his syndicate or one of my deals at the syndicate.com, I'm no longer on Angelus. We do it ourselves, but Angelus is awesome. What are the red flags in deals that people should look for? Red flags are tricky. Okay.
Starting point is 00:13:46 Explain what. So one of the things that most investors on Angelus do is they'll go in and they'll look for deals that are being led by well-known VC firms. So Sequoia or Andreessen or, you know, Greylock or Benchmark is leading around, right? And so usually if you were to be an LP in one of those funds, you'd be very excited to be an LP in one of those funds. And so being able to be invested alongside them is, you know, historically has been a very good deal. one red flag that we've seen over the last couple years, certainly since the last sort of called 18 months, is those companies that basically had been funded by a lot of fancy VC firms at incredibly high prices in 2020 and 2021, crazy prices, stupid prices, they started to run out of money.
Starting point is 00:14:31 And so then the, you know, and those deals were not that, the first deal, that was not available on Angelis. They were, those deals were like sharp elbowed. everyone was fighting for allocation and getting an allocation on an individualist only happened if you were already a significant insider in the company. And even then you had to go to war. Like, for instance, I'm in Mercury, the bank. And like, I've been there since the beginning. And I've had to fight like crazy to get my allocations in the subsequent rounds. And I got, I got by some good friends who led, who led subsequent rounds who literally were like, well, bummer. And they're like, good friends. Really? Oh, yeah. Not friends anymore in my book. Yeah. Well, there were, that, that, that definitely
Starting point is 00:15:08 through a big damper on our relationship from my side of things. But anyway, I have a simple rule with that, by the way. We're getting super inside baseball here, but that's why people are listening. I tell people, if you screw me like that, and I'm a point guard, and when I bring the ball up the court the next time,
Starting point is 00:15:21 just be prepared. I may not pass it to you. I may pass it to your competitor. So if you want to play sharp elbow games, just be prepared that maybe I come up the court with the next Uber and, you know, it goes to your competitor. Totally.
Starting point is 00:15:33 I consider them personal friends still. They're my friends. I hang out with them. I see them on a regular basis, but the ball will not be past their direction. And it's going to go to other people. Oh, yeah. No, no. Yeah. Like, that's my job. My job is to basically just like you. It's like, I'm, bring the ball to court. And, and, and then when the time comes to pass it to people who are going to pass it back to me,
Starting point is 00:15:52 not people who are going to take it and, you know, hoard it. Tribble it and off their foot into the stands. Okay. So that was a red flag. Now they're coming back to Angelist or syndication. Yeah. So now all of a sudden, these steals are suddenly getting bridge rounds because the VCs are trying to keep the companies a lot. They're not doing well enough and they probably never will do well enough to raise at an up round. So we're getting flat rounds or we're getting bridge rounds. We're getting notes. Especially if you're seeing a note going into an existing company that has a well-known VC who led a previous round, that means it's a bridge round.
Starting point is 00:16:24 And suddenly, if it's suddenly a bridge round, a note and a well-known VC is in the deal, they say. And it's basically happening with a note. That's a red fight. Because what that means is that they basically have said, oh, let's go get some. dumb money from Angelis to keep this company alive so that maybe the company can get to a next upround, at which point we will basically go out and raise it, funded ourselves, that we won't give it to Angelus. So there's a lot of, so there's two strategies that have worked well historically in Angelus as a lead. One strategy is sort of the long-term greedy strategy, which is
Starting point is 00:17:00 basically think about it like every deal you do is going to be on your permanent record, and which is true, it's public and permanent, and you do a deal, and 10 years from now where people are going to be like, why did you do that stupid, a deal? Why did you do that?
Starting point is 00:17:11 Yes. And so that sets up your career as a investor to basically be, to use Angelus as a source of capital, but to be very careful about your record. The other strategy, which a bunch of people unfortunately have done, is effectively just a spray and pray,
Starting point is 00:17:26 do a ton of deals and get deal by deal carry because you don't care about the losers and the winners will pay you. and just... So who cares about your reputation or your track record? You're just going to put as much, you know,
Starting point is 00:17:41 as much food on the buffet as possible. And it's up to you to figure out if it's good or not. You being the syndicate member. These are really important red flags for people to notice. And over time, people have learned to know the difference.
Starting point is 00:17:54 One red flag, I'll point out is, you know, high valuations and not a lot of traction. Or, you know, a deal. memo, and we really put a lot of care into our deal memos, but a lack of due diligence and a lack of data in the deal memo. So you got a high price. They want $25 million, $35 million, but they don't
Starting point is 00:18:14 actually have, I don't know, quarterly, monthly revenue spend charts in there. Now, the company's been around it, the product's been in market for six quarters, and you don't know the revenue per quarter, you don't know the growth rate. If that stuff's missing, then, and they're talking about the product roadmap and it's a high valuation, you have to ask, well, the people who have performance will share their performance. The people who have a lack of performance will share roadmaps, plans, features, you know, events that they spoke at. Stories. You know, hires they've made, press hits.
Starting point is 00:18:51 Yeah. So I really like a focus on the business. And it becomes very clear. And you'll see it in when you get updates as well after you've invested. If the updates include, if there's growth. and revenue and customers being signed. Yeah. Founders are going to take credit for that.
Starting point is 00:19:06 It's at the top of the email. First thing. Check out our 20% month over month growth. Yes. And so founders are smart. So you just have to understand if they're selling performance. Yep. Or promise.
Starting point is 00:19:17 Well, if you're selling the promise, you know, you've got to be careful to not have every single thing in your portfolio of selling promise. And you've got to have some things that are selling the performance. One thing I would say with syndicates in particular is, I've got 5,000 people in mine. You've got 50,000 in yours.
Starting point is 00:19:35 Not 11. Yeah. Okay, a lot. But anyway, so when I talk to a founder and they're like, oh, what are you going to share with these 5,000 people that I don't know? Yes. I'm like, you get to decide what you are willing to let me share. So if you're, can I put revenue numbers in? I'd like to put that in there.
Starting point is 00:19:51 Can I put in sort of like a month or month growth rates? But sometimes they're like, no, I'm not sharing that information. And so there are, I've had deals where I've been like, look, I can't share anything. I'm doing this deal. My money is going into it. So you can trust me or not. Make your own decision. But I can't tell you any specifics about sort of where the business is at.
Starting point is 00:20:10 So that does happen. And so it's like it's a balance there. It's a balance, yeah. 2023 is here. And this is the year you need to perform. You need to be focused. And I want your startup firing on all cylinders. And how are you going to do that?
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Starting point is 00:21:48 From the YouTube pre-show, people got into the YouTube channel, YouTube.com slash this week in, sign up, hit the bell so you can get notifications when to go live, but somebody asked while the show was up, but leaves the show in the chat room up so you can get the questions in early, for your portfolio founders who are, raised at the top and have no path to profitability in the short term other than cutting staff, what other options are there besides closing shop? Wow. What are the options here? You don't have a path to profitability. And yeah. I mean, so I think in today's market, I think there's a couple things going on. This happened to a number of my companies and I'm,
Starting point is 00:22:29 we're working through it right now, which is like you you raised, you got to, a million in revenue, the business was doing really well. And then in 2021, some crazy VC firm came along and here, here's 20 on 100 post. And everyone's like, woohoo, $20 million. Yeah, we're going to be able to do a lot of $1 with that. And now they're at, you know, a couple million in revenue, a few million in revenue, hopefully. But the valuation, the multiple that they're seeing in the market is not going to get them an up round. And so then the question then becomes, do you pivot, like just change your business entirely, which is dangerous. And I'm, my office business, I did that a number of times, and it's like, it's a non-trivial thing to do.
Starting point is 00:23:07 Do you take more product risk, which I'll come back to? Or do you basically try to sell or shut down the business? And my argument for all these founders today is like, look, we seem to be at a step change with AI changing the game on the field in a substantial, non-linear way. So, like, you can think of sort of like the last decade, the technology is improving over and over and over again. but we haven't had a major step change since mobile. AI appears to have done that.
Starting point is 00:23:37 And I mean, I like to argue that AI probably is the real Web 3. So the crypto fraudsters base were like, Web 3, Web 3, we all know that with bullshit. But AI appears to have totally changed the game. And so I think for a lot of those founders, this is the opportunity to take the capital that they have and this new platform and make a bet on it and try to figure out how to basically get a step change in their business. And some of them will succeed and some will fail.
Starting point is 00:24:04 So, for instance, in my company, we had raised like a million bucks in 2008 from Reid Hoffman and the Google Analytics founders and all these amazing founders. And we had this business. And literally Lehman happened and we were like, oh, we're so. And we saw this new technology at that point in time called Real Time Bidding, which is what we had just gotten started. And we were like, well, let's bet on this thing. If it works, like, we'll survive.
Starting point is 00:24:30 And if it were f***ed anyway, if it fails, because, like, our core business wasn't going to make it through. And so we bet our entire business on this new protocol. And it worked. And that became a success. And I think AI gives a similar opportunity. So, bold, logical decision making. You have to look at the field, the game on the field, as you're saying, and pick a, make a plan and execute as well as you can against that plan. And that does sometimes mean cutting the staff in half, retreating and extending the runway.
Starting point is 00:24:58 So I literally got an email. third riff from a startup. They finally got the message, you know, 5%, 10%, 20% riff. We should have just done a 40% riff at the start or whatever it was. And, you know, I think they're going to make it. They have, you know, 12 plus months or runway, and they've got a good plan. And I think they can get to break even with the money to have. But it was literally one year of having this discussion. And so they could have made these cuts at the beginning a little more severe and had 24 months the runway, but it is what it is. Sometimes founders are going to take their time
Starting point is 00:25:31 on the cuts. And you know, some individuals do their best work when their back is up against the wall. Yeah. And that's just human nature. You know, you see that with people... Like, when I literally feel the best when I'm literally almost getting it. I'm like, I got nothing to lose now. I'm just going to start fucking jamming. It is a,
Starting point is 00:25:48 it is something that builds your focus. I have to say, when I was doing this skiing and they were like, you have to get more speed or you're going to be buried under the snow and it was a white out condition and my guide when they got 10 feet
Starting point is 00:26:03 feet past me I couldn't see them and I had to use a whistle and I had to follow the whistle and I was like, you know what? I'm going to just go faster. F it. And if I fall, I'm going to fall in powder. And literally I, that's when it clicked for me
Starting point is 00:26:19 that speed is your friend in the powder except for the one time when it was such white out conditions I didn't see the fact that there was a giant kind of like mogul or just like the whole hill. Just plowed and I hit a mogul. I kid you not, I went five,
Starting point is 00:26:36 10 feet in the air. I didn't see it. So I was completely unprepared for it. So now I'm good. You know that thing when you're in the air and you realize I'm in the air? I'm not going to land on my skis. I'm going to land on my back. And I'm like,
Starting point is 00:26:50 oh, this is the end of my season moment. And I'm in the air on my back. And I land. on my back, one of the skis pops off. And it was like landing in a pool. I just landed in a five foot bank of snow. And I was fun. Yeah. And I was like, oh, wow, this is different. If you do fall, it's not a big deal. Uh, yeah, listen, your mileage may vary, but the point is, sometimes you got to take a leap of faith and you got to go for it. And I think the investors would rather
Starting point is 00:27:21 that than you going in a circle. Yeah. Or going so slow down the mountain that you get lost and eaten by wolves. Okay. From the YouTube live chat, here we go. We're cooking with oil now. From a founder's perspective, what are the red flag personality types to be aware of when courting angel investors assuming the angel is relatively new? Okay, great.
Starting point is 00:27:41 So, what are red flags with investors? We see investor bad behavior all the time. What are some early red flags? I mean, sometimes we see it with co-investors. Who are the people that you should avoid? I think there's two that I'm really scared of having dealt with them myself a lot.
Starting point is 00:28:01 One is the, I'm doing this angel investing thing to get rich. Folks, they tend to be very finance oriented. They're going to talk a lot about valuations and portfolio construction and like, and they're thinking about it like it's, you know, they're on Wall Street and they're like, they're making bats. Unfortunately, those people get impatient very, very rapidly. This is a business where it takes forever, and you have to be patient. And forcing things to happen doesn't work in this business.
Starting point is 00:28:33 And those folks can become really painful to deal with it. Okay. So, category one, the impatient folks. They think they're going to get rich doing this. That makes an efficient. Yeah. Well, and you know, if you do have that outlook, you better have a get rich slowly and get rich diversified with using the power law.
Starting point is 00:28:54 And so I think it's fine to have the aspiration to do well investing in this category. You know, that's kind of the point. Yeah. Is that you could have outliers. But you better understand that it takes 25 investments and you have to be graceful in failure. I have had a challenge with this in my early years because it would be very frustrating to find out a founder shut the company down three months ago. And I've been trying to get updates from them for a year. You know, like, oh, yeah, we shut the company down.
Starting point is 00:29:20 And I'm like, what? Oh, three months ago. Yeah. What? Yeah. You didn't even tell me? Yeah. No, you didn't even try to get a bridge round?
Starting point is 00:29:26 Wow, okay, interesting. This is the Wow West, folks. And so you just have to be prepared. And I don't know when you first experienced outright fraud or malfeasance in your portfolio. I didn't experience it for the first 50 investments, but when you hit two or 300, okay, yeah, somebody's going to do something Varanos-like, right? And I've had it happen once or twice. We'll find out in the second case.
Starting point is 00:29:51 So you never know. and it's really hard. Any other archetypes of investors to avoid? Yeah. And then how do identify them? I'm not sure how to identify the finance, brough, who wants to get rich quick. But I would think the number of investments they have and their reputation with other
Starting point is 00:30:08 investor, how long they've been doing it, maybe? Yeah, I just, look, you should always do references on angel investors. It's trivial to do it. It won't take you more than, like, a few minutes to send out some emails. Like, you're going to know people in common with them. Like, do the work. Like, if you're raising money from an investor and you haven't done references on them, you are up.
Starting point is 00:30:31 So, and, you know, I've had a couple situations where there are people who I've worked with who just turned out to really suck. And founders call me up and they're like, hey, and I'm like, run for your life. Yeah, exactly. Yeah. It is, I'll give you one while you think of your next one. Yeah, go ahead. Yeah.
Starting point is 00:30:47 The investor who wants to run the company themselves, and they have a lot of ideas is one and there is a kind of side archetype to this one where they want to send the management team
Starting point is 00:31:03 on never ending research projects, analytics. So they, number one, think they can run the company so they're like, hey,
Starting point is 00:31:14 well, why don't we do this? Or you should do this or, you know, they're not asking things like, have we considered, you know,
Starting point is 00:31:21 uh, white labor, blame the product and what are your thoughts on that, which is how I learned to ask questions from Ruloff and Bill Gurley and other folks is like, hey, let's have a conversation about let's pose it as a discussion as opposed to an edict, even if you think it's the right thing to do. But man, I'm on some of these boards and I'll see somebody come in and they haven't prepared. They don't have a prepared mind as Doug Leone and Michael Moritz talk about, you're having a prepared mind coming into this. If you don't have the prepared mind and then you are sending the
Starting point is 00:31:48 team on, hey, can I get a report? on all the clients by their length and the churn and how many customers we have it. And it's like, whoa, whoa, whoa,
Starting point is 00:31:58 we have four clients. We can just talk about each of the four. We can do it right now. We don't need to make an extensive report. Okay, so that's an archetype for me. And the way I identify those early
Starting point is 00:32:08 is they use non-standard documents. And they argue over things that don't matter in those documents. So I try to be standard documents, let's just use the standard documents so we don't have downstream problems where investors are like, oh, you did non-centered documents.
Starting point is 00:32:25 And even in our side letters, you know, we ask for very simple things. If we own over 5%, maybe we should have a board observer seat. If we over 10%, we should have the option to join the board, if you do choose to do board meetings at some point, and can we get updates?
Starting point is 00:32:37 You know, like really simple, like requests. And even putting them in there is more to a level set with the founder that, hey, we just think there should be governance when this company hits a million in revenue or something. and there should be some planning. So when you're in the product market phase, product discovery phase,
Starting point is 00:32:55 maybe you don't need to have these things. But when you do get to that one million, like you mentioned earlier for startups, yeah, maybe we should be thinking how the one turns into three and the three turns into nine and that might take more planning. Yeah, yeah.
Starting point is 00:33:06 It might take more planning. Have you made a plan? Do you want to go over the plan? I mean, that's literally what I said to them. Have you made a plan? Should we go over the plan? Hope is not a plan. So why don't we make a plan?
Starting point is 00:33:17 Even we can change it. I mean, I literally give all these disclaimers, like, uh, okay, you have any other archetypes? Yeah, I was actually gonna,
Starting point is 00:33:26 busy body, I was the busy body micromanager, usually often like, either a former former manager at a corporate, those are the worst. Like, if they're a manager at a corporate, like,
Starting point is 00:33:35 they're just used to like, like, they're used to performative work and reports and decks and like being the smartest person in the 10 person meeting because they know something about the business. Correct. And like, yeah,
Starting point is 00:33:49 and literally the, The way I say to my founders is like, if I do my job correctly, you don't need to call me because you don't need me because you're amazing. And I'm here to basically be helpful if you need an introduction or whatever when you're trying to raise money. But generally,
Starting point is 00:34:03 that means I've picked a good entrepreneur. And you shouldn't have me taking your time. So I should never ask you to do something that literally you think is a waste of time. And at the point that I ask you ever to do something that you think is a waste of time and it's a cost of the business, please tell me that. You're like, please tell me, hey, this is why I think this is a cost, not a positive ad. And then I can tell you why I think it's going to help the business or not. But my job is not to put costs some entrepreneurs.
Starting point is 00:34:32 My job is to stay the fuck out of the way and let them go execute and perform. And my job is to pick people who don't need me. But the corporate people, oh my God, they just like, they live in this like kabuki world. There's a time for them. You know, if you get to Series B or Series C. No, there's never times of people. Okay, well, there might be a time for somebody with, not the busy body ones, but somebody with deep domain expertise in finance.
Starting point is 00:34:57 Sure. And you're thinking about doing a venture debt and you don't have a CFO and this person's an investor and they got a lot of CFO experience and you can put them on a mission to get four venture debt quotes and you can like use their mutant strength to not derail the management team, but to do work for the management team. And so that goes to how do you manage your investors. And so, you know, that's a really great thing to do is to tell people like, hey, yeah, no, we're good on the product side. The three features you came up with, they're actually on the roadmap, and two of them are low priority.
Starting point is 00:35:29 We already talked to our customer, but the one you got there, yeah, that one is high priority. You'll probably see that in Q2 of this year. You know what we could use your help on? We really need a CFO. Would you be willing to help us find a CFO and maybe do the first round of interviews with 10 of them for an hour or? reach and now all of a sudden that person's like, oh, no, I just wanted to throw bombs into the management team to waste time and I put 50K into the company and now I'm creating 150K in costs.
Starting point is 00:35:59 Costs, like, don't be that person. It's hard enough to run these companies, you know. And if you are going to be that person, you better bring more value than the chaos you're causing. Just don't be chaotic. Like, you nailed it. It's like you've got to win the question game with your investors. When they ask you a question, you got to ask them for help.
Starting point is 00:36:16 You got to be like, and not help about their question because they're going to run tangent on that. Be like, what's the thing that I can use this person for to actually move the business forward and put the onus back on them? And then they can, their costs can be basically balanced by the value they add. And the posers, they will just run away very rapidly when you do that. Yeah, I mean, how can I be helpful is a meme for a reason. Yeah. Some founders do need help. Some founders do not.
Starting point is 00:36:46 Some founders need you to just say, high five, that's awesome. Keep going, Travis. Yeah, good. Nothing to add. Uber's doing just fine. And if you do, you know, want to talk about something that's in my wheelhouse, let me know. And you know what?
Starting point is 00:37:01 Travis would call me when there was a PR crisis or there was the public didn't understand search pricing or something like that. And we would, you know, a handful of times have a really good talk about communicating surge pricing to the public, you know. Or, you know, Elon and I had a talk because I knew about affiliate programs. And I wasn't an investor in Tesla, but I helped him architect the referral program, if you remember, for Model 3. And we just talked about it for, I don't know, maybe an hour or one time, just we were having dinner or something or flying somewhere. And we just had an hour-long conversation about the strategy party.
Starting point is 00:37:42 It was too successful. He had to turn it off, if you remember. People sold so many Model 3. somebody got two free cars because you got $5,000 in credits. Great. That's a good deal. That's a good program.
Starting point is 00:37:53 It was, yeah, too successful is a good, yeah, that's a good outcome. That means you win. Otherwise, literally two outcomes. That's great. And so, you know, these kind of discussions where you can be helpful
Starting point is 00:38:03 and it's in your wheelhouse is I think what you have to be self-aware of as a potential investor. And then, yeah, you know, you have to manage these people. And I have a new technique. Hmm. if I am not being helpful and you don't want me as an investor, I am more than willing to sell my shares in a company.
Starting point is 00:38:23 So if you don't want me around, I get it. And I've literally had two instances in 350 where I said, you know, I think we philosophically differ here. Maybe I shouldn't be an investor anymore. And, you know, in one case, it was because people were doing stuff that I didn't consider ethical. And I just wasn't comfortable.
Starting point is 00:38:44 you know, just from a legal perspective. And I exited that investment. And then in one case, you know, they didn't want, a founder didn't want to share with us the information that was driving the business. And I was like, okay, that's odd.
Starting point is 00:39:03 And this is normal information that you would share with people with this percentage ownership. And they just were like, we're not sharing any information. It was just a huge red, flag for me and I was like, this is a trust issue. Like, if you don't trust me, we shouldn't be a business together. Just, and it was like a million dollar investment and we exited.
Starting point is 00:39:23 So in these situations, I don't, have you ever had that happen where you wrote off an investment? We just saw that with Citizen and Sequoia. There was the FT story. Yeah. Where there's a cram down around. That's not too uncommon. But have you been in it where you have to separate from the founder and how did you handle it? Yes.
Starting point is 00:39:39 And you could abstract it, you know, so. I had one where. they were just doing a really poor job communicating. And, um, and I, I literally, you know, I called the founder up and I was like, look, just let you know. I've asked multiple times for these things. You've chosen not to do them. I'm not asking for a lot.
Starting point is 00:40:03 Um, and so like, I'm stepping back. They didn't have the money to buy me out and I wouldn't have asked for them to. But I was like, look, I'm writing this to zero. And as far as I'm concerned, good luck. Now, I subsequently actually just recently found met the guy who went in and helped turn around that company. Now the company's doing great and there was like a leadership change and they turned
Starting point is 00:40:25 around everything. And so I met the VC from the bigger VC firm who went in and did the work, like helped him rebuild that business. And he was like, oh my God. And I was like, you did God's work, my friend. Thank you. Because it was, it was bad. I mean, listen, people can disappoint you in.
Starting point is 00:40:43 all relationships. This is a business partnership, customer, employee, founders management team, investors, service providers. People can disappoint each other. There's so much opportunity. My best advice is if it's not working out to just say, hey, for the sake of just being professional, this isn't working out for me. I'm guessing it's probably not working out for you. Why don't we move on to this type of relationship, right? Listen, we all know, hiring world-class freelancers is a game changer for your startup or even if you're working a big company. You want to have a great talent marketplace where you can find these people, but then you're always worried, oh my God, it's all my money going to go to commissions.
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Starting point is 00:42:23 with $500 worth of designer or developer time. Contra.com slash twist right now. Go get that 500. Okay, from the live chat, Vicki asked what's a concept you thought was true early in your career and that you followed and that you now think about differently? You have a credo or an assumption
Starting point is 00:42:41 a heuristic, Zach, that you believed early that you now changed your mind about or you've evolved on. I don't know. It's a really good question because it makes a thing. One thing that came to mind was, you know, that I could read founders
Starting point is 00:43:03 like a poker player. And I really thought I could look into people's eyes and know if they're going to be a winner or not. Yeah. And I do think I do that better than the average investor. But I think that I may have over indexed in my belief of my ability to do that because so much of my deal flow came for my network.
Starting point is 00:43:26 And my network was filled with so many amazing people. So my attribution was early on, look at how great a picker I am. And it was like, this is like things that are floating around your immediate circle. And your immediate circle is, well, you know, people I'm friends with. These are all, you know, high-end entrepreneurs who are doing incredible stuff in the world and capital allocators. Of course, it's going to be like high-end stuff, right? Yeah. So, like, you know, Bob Dylan's like, wow, you know, I can pick people to sign for my record label who are really smart.
Starting point is 00:43:57 It's like, well, just everybody's hanging out with Bob Dylan in the 60s, 70s and 80s. You know, like they're all in his orbit. So now I have moved to let's look at what the customer has to say in addition to what I think. And I know what I'm finding? Frequently, I'm able to read people and how good they are at building a simple product that solves a problem in the world and being obsessed with customers. And then when I talk to customers, it's clear they're obsessed with them. And it's clear they're building stuff for them. Yeah.
Starting point is 00:44:29 So here we go, right? Yeah. Yeah. You have any of you? Yeah. You know, I've just been continually impressed with just how deep the learning curve is for this business. I mean, capital allocating.
Starting point is 00:44:45 It just, there's just so much to learn. And I'm learning new stuff every day. And you're a decade in. Exactly. Yeah. Not counting your entrepreneurial career. I know.
Starting point is 00:44:56 And I would, you know, I spent a lot of time helping companies raise money and advising and doing this work before I did this work. So it's just, it's great. It's, it's this,
Starting point is 00:45:05 the self actualization of learning and becoming better at the job is still very, very alive. I think of that ever, way I would be probably sad, probably just immediately retire. But yeah, no, it's, it's really, I'm really enjoying it. It's really fun. I'm learning a lot too. One of the recent learnings I had. So I'll rephrase this question, any recent learnings or, you know, in the last year or two. And one of the recent learnings I'm having is what a profound impact we can have on founders post investment. And I think I under index to this again, my own ego, thinking I could
Starting point is 00:45:37 pick people. And that did work early in my career. But once we pick people, I've realized when We do a great job of teaching them how to do a board meeting, teaching them how to make a two-year plan, teaching them how to think about customer acquisition, teaching them about accounting, silly stuff, or seemingly silly stuff. But founders don't know accounting necessarily. They haven't done accrual versus, you know, cash-based accounting.
Starting point is 00:46:07 These are concepts that they may just not have run into yet. And so getting them focused on things that can build a stable, scalable business, I was like, yeah, everybody will figure that out. But sometimes they figure it out and takes them a year. And we could have them figure it out in 10 days with the help of a service provider, with the help of another founder.
Starting point is 00:46:27 And so that I underestimated and maybe under-indexed on as well. So I'm really thinking about supporting the founder's post-investment a bit more and then identifying, hey, where is the zone of excellence for this founder? and where are their blind spots? And so my ability to say, this founder is so good at product, but they're not good at hiring and finding people that will level them up.
Starting point is 00:46:50 Oh, this person is great at hiring, incredible people and spending money. They're just not focused on the customer or whatever it is, right? And that's something where every time we invest more in it, we see greater outcomes. So, you know,
Starting point is 00:47:04 they get to their next round of funding. So I've just been thinking about that. And then also as your portfolio gets larger, identifying when the inflection point is. And that's something I'm really starting to study. And I have a new rule. It's 40K a month in revenue. Okay.
Starting point is 00:47:22 All right. That's when my eye is for you. Yeah. Because here's the thing. Can't be my mistake. Yeah. When you hit 500K, 5, 10, 15, 20K.
Starting point is 00:47:33 Yeah. You could just get one customer. You could get a whatever, you know, you get a little bit of traction. maybe you're spending $2 to make one. You know, it's just in an early stage startup. It's a sign of life. But when they get to...
Starting point is 00:47:45 You can be your friends doing that. Yeah, it can be all kinds of things happening. You know, people just trying a product, but it just doesn't have market pull. When I see them hit that 40K a month, I times it by 12, hits 500. I'm like, yeah, they figured something out. That's what you get excited.
Starting point is 00:48:01 And then I say, hey, should we have a board meeting? Maybe make a plan and see if we can triple it. Yeah, yeah, yeah. People were like, yeah, you know, I was told don't do board meetings until series A or whatever. I'm like, yeah, but you have 500K and you want a series A. Do you want to make a plan to get it to 1.5? Because if you get to 1.5, you're going to get a series A. Yeah.
Starting point is 00:48:20 At 500K, you're not. Yeah, no, I like that. Yeah, not right. Not these days. I don't think so. I think the bogey, what do you think the bogey is now to, you know, lock in a series A? I mean, you was. 3x plus annual growth
Starting point is 00:48:35 you know over a million in error that's I think that's lock in like when you start to and not being in a crowded category that's full of a bunch of actually having a viable path to being a big business
Starting point is 00:48:49 all the things that are normal but a lot of people seem to forget yeah you got okay Emmett has a question would you recommend building the relationships with VCs and Angels months before deciding to build a product or company
Starting point is 00:49:01 how would you go about doing that? So, sure. Yeah, like, if you have a natural way to build relationships with BCs, natural meaning you do the things that they enjoy doing and you get to hang out with them, not in a professional transactional setting, but in a, you know, you kiteboard with them, you ski with them, you hike with them, you cook with them, you do yoga with them, whatever these things are, for sure. I mean, one of the best things that ever happened to me in my career in Silicon Valley was I started playing poker with the VCs when I just moved here. And all of a sudden,
Starting point is 00:49:34 I'm hanging out with a bunch of VCs as a 25-year-old kid just, you know, at their Sand Hill offices. And God, it was so powerful. Like, I got to learn by osmosis. I got to build a lot of long-term lifetime relationships.
Starting point is 00:49:49 These are still my good friends. That's, yeah, if there's a way to do that, it's a superpower. You should, you should watch into that. But the way not to do it is to say,
Starting point is 00:49:58 can I get your feedback on my idea? because if they're doing well, they're just like, well, just go build something and then let's talk about what you built. This is not my idea to help you come up with an idea. This ideation obsession, it's like,
Starting point is 00:50:14 I feel like when you're in that ideation phase, that's up to you. Like, unless you have a great relationship with the person, you're at the poker table anyway, and you're where you're, you're drinking some coconut water on the beach, you've got nothing to talk about anyway.
Starting point is 00:50:28 You're like, I'm thinking about AI. I wonder if it would have a problem. apply to sports in some way. And you can have a brainstorm there, but the activity is first and this is second. You know, can I get coffee with you to go over my ideas? It's like really selfish with a busy person. It just shows that you're not considering what you talked about enjoying your life.
Starting point is 00:50:49 Maybe they have a family. Maybe they've got obligations. People get busy when they're older. When you're young, you have time, not money. And when you're older, you have money and not time. And so you're, you really have to, I know people who will just give people an angel investment to get them out of their hair. No, no. I wouldn't do that.
Starting point is 00:51:10 But like, I'm just saying, somebody in their life was a relationship. And they're like, yeah, no, I'll put 5K in, you know, whatever. Yeah, I want to support you, whatever. But yeah. All right, Bob G. One thing I would add is Twitter. Oh, my God. That's great one.
Starting point is 00:51:22 I've built a lot of relationships with people on Twitter. People who just engage in my comments and I engage in their comments. built a relationship over the years where now if they were to reach out and basically be like, hey, I'm starting a company, here's the deck. I would immediately read that. Because I've built respect for their thinking and the way that they engage
Starting point is 00:51:41 and the way that they approach the world as a result of a natural organic Twitter interaction, which leads to me prioritizing the way that I interact with them when they reach out with a pitch. As opposed to the dozens of cold emails I get every day. I mean, I literally go through and just
Starting point is 00:51:57 read it real quickly, no, this is not my archive, archive, archive. But if you're clever, intelligent, maybe on the margins, you're a little spicy, but not a jerk. And you're that reply guy, as they say. It could be a guy. It could be a they-them.
Starting point is 00:52:12 It could be any gender you like. But reply guy kind of rhymes a bit. The reply guy archetype is a real thing, right? And there are some people who have built massive relationships just replying to people who are powerful. and Twitter uniquely allows you to do that. And so keep it intelligent, keep it respectful. Don't be a jerk.
Starting point is 00:52:36 But you can be spicy on the margins. That's fine. That'd be fun. Yeah, clever. I like clever and fascinating. Those are words, if somebody's clever and fascinating, yeah.
Starting point is 00:52:45 They're insightful. You know, oftentimes- Insightful great. If you basically, like, somebody is talking about something, there's a thread going on about something, and then you're like, oh, what about this?
Starting point is 00:52:54 Here's another way to think about it. Here's a link to something interesting. You're adding to the conversation. Like, you know, I, when people do that, that to me, I enjoy reading those things, being like, oh, that's a cool way to change my thinking. Austin Al-Read. And he wound up getting Austin, A-U-S-T-E-N. He was like a reply guy.
Starting point is 00:53:12 So go look at his replies from the early days. All he did was like when he was building his business is reply, reply, reply. And I think that's, and he's got a, I'm looking at it right now, he's got a quarter million followers. So that's a thing. That's a thing. All right. ex ante asks how hard oh wait there's one more from bob g bob g s what startups OG bob g is back what startups that you invested in faced the most difficult early
Starting point is 00:53:39 challenges what did you personally learn from it wow okay good Zach you got a um I got anybody I mean the guy there's a myriad right like it looks startups is a rocket ship ride into the walls of real personal incompetence and so like whether you're like literally Elon or the youngest, freshest entrepreneur on the streets, you go into the market and when you're Elon, day one, it's a multi-billion dollar business and you hire a thousand of the best people in the world. But like, you're, and because your competence is so high, your bar is so high, you crush, but you will immediately hit your limitations and you will just get your face ripped off. And it will just be in a continual process of getting your face ripped off,
Starting point is 00:54:22 stitching yourself back together, solving the problem, hopefully, repeat over and over and over again. And it doesn't matter where you are in the life cycle of entrepreneur. And so, I mean, honestly, every company that I've interacted with from start to finish, it's just a never-ending series of challenges. And the question is just like, can they work through them? And, you know, are they good at figuring out who's the right person asked for help? How do I solve this problem? And then rinse repeat, rinse, repeat, rinse, repeat. I mean, look at, look at Elon over at Twitter. Are you a personal experience with that? I mean, God, the guy just, his level of incompetence is way higher than any of us every week.
Starting point is 00:54:56 But, I mean, he literally just jumped into the shark pit and said, let's go. I mean, it's a very astute observation. He's built some of the most legendary companies in the history of commerce, and now he has to do a turnaround. Oh, my God. With a company that's at scale. Who all hate him. And, yeah, maybe a certain percentage of the people there hate capitalism. Yeah.
Starting point is 00:55:20 And profits. Yeah. And working for a living. And working. Yeah. And doing work or coming to an office and doing work. I mean, it is crazy when you think about it. Like a lot of companies got hijacked by the employee base.
Starting point is 00:55:34 Google, probably the number one example where, you know, they just all of a sudden, the company became a miserable place to work. And the people who were running the place and, you know, the, you know, defining the culture are the people who Larry and Sergei would least like to have dinner with or go kiteboarding with or have coffee with. And it's like, how did that happen? You know, and it's like, they need to go in there literally. And, you know, and Sergey's back in town,
Starting point is 00:56:05 according to many reports hanging out. I don't know if Larry's going to come back, but they need to just start firing people who are not there to do work like Zuckerberg is. It has to be, you know, the people who want to manage work or, you know, theatrically do work,
Starting point is 00:56:26 take credit for workers' work. They're going to have to rethink that. And that might mean letting go of people who, yeah, have some amount of notability or notoriety, whatever it is inside the organization. But, you know, when you look at what they're actually doing, the output,
Starting point is 00:56:47 that's the problem. And I'm pretty happy with myself that I've built organizations, you know, the small ones that I operate, where everybody's actually doing work, not just sitting around taking credit for everybody else's. All right. We'll do a last question here, I think, because we are. And meta, did you see MET is doing thousands more layoffs in their efficiency thing? I'm like, whoa, I bought that stock at $94 in my day trading. Good job. It's like, whoa, I don't even know what it's trading at.
Starting point is 00:57:16 And I wonder what MET is trading it. Let me look it up here. I'm at a stock. I mean, when are they going to trade changed? You're an addict. I'm not an, oh, 181. Whoa, I literally, uh, pretty close to doubling my money here. Whoa.
Starting point is 00:57:27 Nice, nice. Uh, what a crazy trade that was. All right. Good job. Good job. Good job, everybody. Okay, here we go. How hard do you negotiate on terms during your early stage deals?
Starting point is 00:57:36 Is your preference to fund on a fairly standard safe rather than an equity round of lots of terms? Of course, we want to do standard terms. So let's just go to the first part of the question. This is from ex ante. How hard do you negotiate our terms? I kind of live by the Warren Buffett school. I try to live by the Warren Buffett School for everything.
Starting point is 00:57:53 That guy's just like, he literally just, he, he sent so many examples. I'm just like, just re-follow the book. If they set a price, I take it or I leave it. And that's it. I'm not, I'm not negotiating. It's like, like, you can give me the price and I will say yes to it. I'll say no to it. Will you tell them that you're passing based on valuation?
Starting point is 00:58:11 Yeah, yeah, of course, yeah. Yeah, me too. And then they're like, they're like, well, and I'm like, at that point, like, like, that we didn't come together in the right way. And thankfully that doesn't seem to happen too often. Usually it's like, if I want to do the deal, I think the price is fair. You know, then I'll say yes.
Starting point is 00:58:30 And then if I'm setting the price, you know, let's say they really don't want to set the price. You know, I come up with a fair number. And I'm like, this is my number. And not negotiating because this is the number. And, yeah. Now, there are situations where it becomes competitive. and that gets a little more dicey.
Starting point is 00:58:50 And they're just like I come up with the number that I want to pay and pay it or I lose a deal. But it's not about it's not about negotiating oftentimes. Yeah, I have the exact same philosophy. If you are asking us to make an offer, we will ask you two or three times. What is your target valuation is the way I like to phrase it? They're like, well, we want you to tell us. And I'm like, well, what would be a valuation you think is fair?
Starting point is 00:59:18 And they're like, well, we want the market to tell us. And I'm like, okay, what would be a valuation minimum that you would accept? Literally, I've got like seven ways to ask this. If an investor is asking you to come with a valuation, I suggest you just come up with one that you think is fair. If you want that investor, because then you move the conversation along, if you're over-optimizing on valuation in a market like this, my lord, what are you doing? I could understand that technique. if you don't need money in 2021 and you're trying to see if somebody will do some stupid valuation at a FOMO, sure, you know.
Starting point is 00:59:50 Oh, you want to invest in Stripe? Yeah, our last round was $50 billion. We don't need money, but you're free to give a term sheet and I have a fiduciary responsibility to review it with my board. You can take that approach. Yeah. And I'm sure they did. And I'm sure people lobbed in term sheets that were absurd and, you know, fascinating.
Starting point is 01:00:05 But in the early stage, what, how much money do you need to make it to the next level and how much dilution do you want? So, okay, you need $3 million. Okay, you want to dilute no more than 20%. Okay, so you got a $15 million evaluation, a $20 million evaluation, it's somewhere in that range. And then you just test it with the market. And if you're happy with that valuation and you think it's reasonable, but then both sides of the table can feel like they, you know, did a reasonable transaction and you can get back to work. If you're optimizing for that extra $5 million, the most talented investors will say, okay, you know what, maybe I'll invest in the next round. So let me know.
Starting point is 01:00:42 and then you get some sucker at the table who's trying to, and we talked about it before, maybe you're getting, you know, the finance guy or the, you know, send you on a wild goose chase mission gal
Starting point is 01:00:56 who, you know, you don't want as investors. Now you just added somebody to the cap table because you're optimizing for valuation. It's a red flag for me. Like,
Starting point is 01:01:05 in fact, at the point that the entrepreneur is more focused on the valuation than our relationship and the business that's going to be built there, that for me is like probably not a deal I want to do. Yeah, it's kind of weird. It would be like going to like a great restaurant and they're like trying to get you to buy.
Starting point is 01:01:21 It's like that guy who drops salt down his dirty arm and then expect you to eat a gold steak for a thousand dollars. It's like, that's not the steakhouse I want to go to by the way. That guy's brilliant though. I mean, he doesn't mean like. But it's brilliant. Yeah. If you pay a thousand dollars for a steak from him, because you could go to an incredible. Yeah, there's suckers born every day.
Starting point is 01:01:41 but like I'm not going there to see you in sunglasses and a dirty white t-shirt drop salt down your greasy, sweaty arm onto my steak, and I don't want gold leaf on the steak. Salt Bay, it's the dumbest thing I've ever seen. Come on, it's brilliant. Respect the game. I mean, it's brilliant for suckers. Brilliant.
Starting point is 01:02:02 But that's insert, do me a favor, insert Zach doing salt bay, like a meme of it right here. It's just not what I'm interested in. Like, that's the equivalent of like optimizing for your valuation. You look like an idiot, right? Or me trying to grind you down on valuation. You know, if you ask me what the valuation is, I'm like, well, public comp is four times revenue. You're a private company growing faster, so eight times revenue, ten times revenue, whatever you think is fair.
Starting point is 01:02:33 And you can get to this range pretty quickly. So don't over-optimized. Is the broad-based answer? It's a red fine. job. Let's let everybody know if you want to get in touch with Zach and you got a great idea. Best way to do that is to get into
Starting point is 01:02:49 his network, meet some of his founders or co-investors and get an intro. But you could always be reply gal or guy. Pay them if you're non-binary and just reply to him with intelligence stuff on Twitter. A gender neutral
Starting point is 01:03:05 reply guy. No, no, no, no. A general neutral singular. Like, so we have he, she, And we just need a, because this day is plural. Like, it's a plural word. I'm trying to evolve here and make sure I get it right. I think like V. I like y'all.
Starting point is 01:03:20 I just use y'all. Y'all. When I come in meetings, I'm like, y'all got to work harder. Yeah. I just Bill Gourliott. Yeah. Y'all are not hitting the standard that we need to hit at this company. Y'all need to work harder.
Starting point is 01:03:31 I just go with you. And I like typing it. I like a Y, a poshchry, A-L-L, y'all. It just rolls off the tongue. It's not gender specific. Howdy? Y'all. How do y'all?
Starting point is 01:03:43 How are y'all? Do you guys want to wrap the show with Salt Bay decorating $150 burger at his restaurant? Oh, please. Yeah, show me this. Show me this. This is going to be painful. No, essentially, no. Oh, so gross.
Starting point is 01:03:55 Look, you're too close to the food. This idea that he's getting so close to the thing, you know, and there's no way that burger's worth it. You're such a hater. And the gold leaf is stupid. Oh, you're a hater. You're a hater. No, I'm not a hater. It doesn't add to the food.
Starting point is 01:04:10 If you want, of course, it does it show. was a disrespect for cuisine. Yeah, it's just garbage. This is someone recreating it with a Big Mac. Oh, he just, he's putting gold leaf on a wopper. This is genius. So the gold leaf on the wopper. Oh, this is so great.
Starting point is 01:04:30 And then he's going to squeeze it. No, you know what? I went to Shakehack yesterday. Burger's 12 bucks. Double, double, maybe 13 bucks. I don't know. I tipped 14. I mean, I mean, I was like, whoa, 14 bucks.
Starting point is 01:04:45 And I was like, you know what? Worth it. It was delicious. I guarantee that Truffle burger I had at Shake Shack is better than that monstrosity covered in gold leaf. You know what? You put gold leaf on a burger. What you're telling me is the burger's not good enough. Respect the game.
Starting point is 01:05:00 The man's got game. I mean, maybe. He's a performer. I think he's a performer. And you know what? That's the point. I'm not looking for formative. I'm looking.
Starting point is 01:05:11 hint for a great burger, great snake. All right, listen, great jobs out. It's all that to be. You too. And just follow Zach Collius. Interact with him. Go heliskeying with him. Go hell-liskeying with one of the owners of one of the football teams,
Starting point is 01:05:27 some of the NFL teams. And I didn't even know until like halfway through someone was like, oh, that guy owns his football team. I was like, oh, that's pretty cool. He's actually a really cool guy. Like, so, yeah, that's a good way to get to know people. Tell Jed Yorker said, huh? It was a joke.
Starting point is 01:05:41 It was a joke. It wasn't in January. Believe it out. Jet's a cool cat from the 49ers. Cool cat. Nice guy. All right, everybody.
Starting point is 01:05:48 Keep it joyful. Oh, there he is. There's Zach. Sprinkling that salt on his portfolio there. Actually, fixed a good picture for it. It looks great.
Starting point is 01:05:56 So handsome. I don't want to make this a hurrah. I don't want you to call this week's HR, but you look great. Oh, thank you, yeah. Yeah.
Starting point is 01:06:03 It's, you know, they use a special facial Mr. I'll have to add that to my Yeah, yeah. You have a mister. Well, one of my companies.
Starting point is 01:06:16 Oh, tell us. This is a miss for mister? Oh, no, no. It's way better than that. So basically they... Is it a non-gender mister? No, come on now. No, so basically, it turns out if you're going to add
Starting point is 01:06:27 chemicals to your face, they have to get to the pores of your skin. And your skin is actually very thick and it doesn't like things to go into your face. Ah, right. And so if you want to look young and healthy, and basically, you know, you want to be, you want to be beautiful. You've got to basically use nanoparticles to basically add.
Starting point is 01:06:48 Nano particles. Nano particles. Yeah. Well, what's the name of this startup? We're all pins and needles here. I know. You've got to keep you on the, for your, for your skin. You got nanoparticles.
Starting point is 01:07:03 Incredible. I literally. Is this one of these Korean, I think it's one of these Korean beauty. products. That's like my wife's Korean, so I'm very up on all these. No, no, the company's called Droplet. I don't know about nanoparticles, nor do I know anything about facial stuff, but the founder is amazing. And she reached out, and I've known her for a long, long time. And other investors are smart. And so I was like, okay, whatever, I'm long for the ride. And so then I got one, and I started using it and makes me look pretty.
Starting point is 01:07:29 So, you know, drop wood for your skin. Droplet. Dot.io. Droplet. D-R-O-P-L-E-T-E dot I-O. Use the promo code Zach. For $50 on your droplet. Look at that.
Starting point is 01:07:43 Yeah. Anyway, nanoparticles, they do seem to work. I don't make myself look pretty for your show, Jason. I got to, your unpaid talent has got to look pretty. Absolutely. You look handsome. All right, everybody. We'll see you next time.
Starting point is 01:07:56 Bye-bye.

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