In short
This Week in Startups - Episode E1940 Summary
Episode Title
How AI and Remote Work is Coming for Your Job Hosts: Jason Calacanis, David Weisburd Guests: Jeff Richards, Ryan Denehy Timestamp: [E1940](https://www.thisweekinstartups.com)
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Introduction
- Overview: The episode discusses the current landscape of startups, focusing on down rounds in venture capital, changing business operations due to market shifts, and the impact of AI and remote work on job availability.
- Key Topics:
- Down rounds and investment structures in venture capital.
- Operational changes in response to economic conditions.
- The effects of AI and remote work on employment dynamics.
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Key Discussions
- Down Rounds in Venture Capital (5:26)
- Definition: A down round occurs when a startup raises capital at a lower valuation than its previous round.
- Recent statistics show down rounds made up 11% of VC deals in 2023, reflecting a significant market shift.
- Expert Insight: Jeff Richards and Jason Calacanis suggest that down rounds, while concerning, do not necessarily indicate a company's long-term viability. Instead, they can be a part of a healthy investment cycle.
- Cram Down Rounds (21:67)
- Cram down rounds also known as "pay-to-play" rounds, require existing investors to invest additional capital or risk losing their stake.
- Implications: Founders may face intense negotiations during these rounds, which often lead to tensions among current investors and management.
- Changing Operations in Response to Market Shifts (23:24)
- Companies are adapting to new economic realities by scaling back excessive spending and optimizing resources.
- Advice for Founders: Focus on building sustainable business models, profitability, and maintaining a strong sense of financial discipline.
- AI Adoption and Remote Work (37:26)
- AI Integration: Companies like United Airlines are using AI for various functions, including chatbots and operational efficiencies.
- Impact on Employment: The rise of AI is expected to change job availability, with predictions of increased efficiency across sectors, but potential job displacement in certain roles.
- Market Insight: Small businesses are likely to benefit from AI adoption as it enables them to function more efficiently and effectively.
- Impact of Remote Work on the Global Economy (1:02:17)
- The rise of remote work has led to new economic dynamics, including offshore hiring.
- Companies can leverage global talent at a lower cost, affecting job availability in higher-cost regions.
- Discussion Point: The balance between onshore and offshore workforces will continue to evolve in the coming years.
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Key Takeaways
- Investor Perspective: Investors are becoming more discerning, looking for strong fundamentals in the companies they support.
- Founders' Advice: Build for the long term; short-term valuation changes should not dictate business decisions.
- AI’s Role: AI is a dual-edged sword; while it presents opportunities for efficiency and growth, it also raises concerns regarding job security.
- Remote Work's Future: The shift towards remote work is expected to continue, leading to changing employment landscapes and operational structures in various industries.
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Conclusion
- The episode emphasizes the importance of adaptability for startups in a rapidly evolving market influenced by economic pressures, technological advancements, and changing work environments.
- Founders are encouraged to focus on sustainable practices, invest in AI, and leverage remote work effectively to thrive in this new landscape.
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Sponsors
- NetSuite: A cloud financial system for streamlined business operations.
- OpenPhone: Business phone solutions for seamless communication.
- HiddenLayer: AI detection and response solutions for secure generative AI applications.
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Follow the Guests:
- Jeff Richards
- [Twitter](https://twitter.com/jrichlive)
- [LinkedIn](https://www.linkedin.com/in/jeffrichards)
- Ryan Denehy
- [Twitter](https://twitter.com/denehyxxl)
- [LinkedIn](https://www.linkedin.com/in/ryandenehy)
- Jason Calacanis
- [Twitter](https://twitter.com/jason)
- [LinkedIn](https://www.linkedin.com/in/jasoncalacanis)
- David Weisburd
- [Twitter](https://twitter.com/DWeisburd)
- [LinkedIn](https://www.linkedin.com/in/dweisburd)
Subscribe to the Podcast: [This Week in Startups](https://www.thisweekinstartups.com) on various platforms like Apple Podcasts, Spotify, etc.
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This markdown summary encapsulates the essential discussions and insights from the podcast episode, providing a thorough understanding of the topics addressed.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00Well, this is a moment in time. And I just took it. There you go right on my bag. Is it Elon? I'm stealing a mug. Is it? Yeah, have one. Then I actually need one. I don't know that much. But I mean, it's so classic. David, how are you doing? I'm doing well. I'm in Miami right now. One of the portfolio perks is an office setup for me whenever I come in. But you're based in New York, am I correct? I'm based in New York, yeah. That's that great view. Where is your office? We're in One World. We're on the 85th floor. Amazing. So that's 85th floor. Oh my Lord, how many floors are in the building? I think they call it 100, but I think if you actually count, it's probably like 92, 93.
0:39I think there's some marketing going on. You think what they do is they make the lobby like 10 floors and then they give them a little little bit of air cover how's your tooth done it's good the swelling's down and um i was talking to my wife and i'm like everybody's commenting on youtube of how bloated and how fat my face looks and she's like well it's welcome to being a woman everybody just talking about all your you know outside qualities and giving you a hard time but uh anyway the swelling's down my energy is off the off the charts i did a cold plunge today so i'm ready to go let's get to liquidity episode 13 we made it and we've got the uh we got the liquidity conference liquidity summit go to liquiditypod.com you'll see the summit page supposed to be 100 people i extended it to 125 david because you gave me so many great recommendations for lps 25 thank you very much for that you're you're a match and it's just uh gps lps three days in napa uh we get there the first week in june sunday monday tuesday wednesday sunday we arrive have some food and play poker just hang out monday talks all day dinner poker at night tuesday we have talks then in the afternoon we do activities so you go painting cooking class play pigeon shooting we have a bunch of different things to do in napa such a great place to go then we do food and poker again wednesday we have a closing brunch so it's pretty pretty fun agenda what's overall vision you haven't told me that much you know i'm trying to build relationships with all these different gps in the world because we've gotten earlier and earlier and the way as you know david for a while people will judge an early stage program like founder university or accelerator or y-combinator or tech stars is how many of those companies goes on go on to get future funding usually it's like 10 20 30 percent and so in order to get those numbers up um and we need to meet seed funds and series a funds and show them our inventory in other words hey these are the founders we've invested and we think are interesting and then match them so i just want to build relationships also i want to have fun and i just find three days together only gps only lps no founders no service providers you know like 50 service providers a month try to get into the event lawyers accountants headhunter real estate brokers because they're looking to sell but we want to have like a no sales kind of situation so there's other big events out there there's tons of family office events but this is my small one to pair with the podcast what david and i are doing here just to build relationships with people that we think are high quality to help us all trade notes and become better at what we do that's absolutely well i'm excited and jessica's coming so awesome all right well there you go with us as well absolutely you and i this is the same thing beauty and the beast right you get a 10, you put it with like a four, you average out to a seven.
3:32Beauty and the brains. Beauty and the brains, maybe. I think it's, in my case, it's beauty, the brains and the beast. All right, let's get started. This Week in Startups is brought to you by NetSuite, the number one cloud financial system bringing accounting, financial management, inventory, and HR into one platform, giving you one source of truth. By popular demand, NetSuite has extended its one-of-a-kind flexible financing program for a few more weeks. Head to netsuite.com slash liquidity. OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop.
4:16Twist listeners can get an extra 20 % off any plan for your first six months at openphone.com slash twist. and Hidden Layer. Generative AI is revolutionizing industries. Hidden Layer's AI detection and response solution secures your generative AI and LLMs for malicious attack, helping you generate more by enabling seamless and secure generative AI. Visit hiddenlayer.com slash twist to learn more. Welcome back to this week's liquidity podcast. With me today, I have Jeff Richards, managing partner at Notable Capital, formerly known as GGV. We have Ryan Dennehy, CEO of unicorn startup electric.ai.
5:02And of course, we have Jason Calacanis from the Launch Fund. I'm your moderator, David Weisberg, co-founder of 10x Capital. Today, we have several great topics on the docket, down rounds, something most people don't talk about, how do they work, and are they as bad as they sound? And we'll discuss how large corporates such as United airlines are integrating AI today. We'll finish with the latest three investments from Jeff and Jason. Let's dive right in. This September, Pitchfork reported that down rounds accounted for 11 % of all VC deals, more than any time in the past two decades. That being said, down rounds were still nowhere close to dot com numbers where they reached a record high of 58 % of all rounds.
5:45Jeff, when you look at 2024, do you take the over under the 11 % of down rounds that you had last year? It's a great question, David. Let's zoom out a little bit. So to me, the down round thing, and I answer this question coming from having been a founder, you know, back in the late 90s, early 2000s, which was kind of a crazy time to raise money and then deal with the aftermath of the dotcom bubble, where I raised capital and dealt with, you know, all kinds of different structures. But the down round question you mentioned, and we don't talk about it much, it's a little bit like Hollywood and Ozempic or plastic surgery.
6:16Nobody really knows who's done what. So it's very hard to make sense of that data. If you ask the question of what percent of private companies that raised in 21 or 22 have a lower stock price today, in the public markets, it's almost all, right? Almost every small cap and mid cap tech company has a lower stock price today. And they would all love to be back where they were, but they're down 60%, 70%. You look at the software market, multiples peaked in 21 at 20x forward revenue. Today, they're at 5 % to 6%. So even if you grew your business 3x or 4x in the last two to three years, you're fighting a headwind where multiples came down 75%.
6:55So I just don't know. I know the 11 % data point. I think it's a hard one to get your head around because the reality, companies that are raising money today are good companies. It is a very hard market to raise capital in if you're not a pure AI infrastructure play. And so those companies are great companies. We've seen a very challenging fundraising market. I'd be curious to see what Jason has seen over the last 12 months. But I can tell you that just dealing with the headwind of market multiples, folks that have been able to raise it a flat round, that's the new up round. And frankly, as an investor or as a founder, if you're playing the long game and you're looking five, 10 years out, an up or down round in the near term isn't going to impact the long term outlook of your business.
7:39You think about companies like Square or DoorDash that did down rounds, did rounds with structure. They went on to build multi$10 billion companies. It just didn't impact them in the long run. So our advice to founders, focus on the long run. Get whatever you need to get done to move on. Get the capital you need to build your business and go build your business. yeah when when a market crashes this severely and the tide goes out you figure out who's wearing swim trunks and who isn't uh as the famous expression goes i like your jeff uh plastic surgery one although with these celebrities when they start doing stuff to their face with the uh botox like when they start to i heard 20 30 year olds are doing botox anyway you sometimes if they go too far you can tell there really are two types here uh david there are down rounds okay you raised at 100 million now you're raising at 50 okay we get it then there's cram down rounds and so cram down rounds are a different beast and i just want to talk about those for a second because those are also happening and they're happening with very notable companies and these are also referred to as pay to play rounds as well that's actually a hollywood term if you hire somebody to do a movie if the movie gets made they get paid movie doesn't get paid made they still get paid pay to play what's happening with the cram down rounds is a founder goes out they try to raise money they can't there's too much of an overhang in the company company's making let's say 10 million dollars in revenue last round they raised that 200 million somebody put 30 million into the company for 50 they've got you know some cash left but they're still burning but they're back to growing so there's there's a company here but nobody wants to invest at that valuation and they don't want to invest with the 30 million they can't raise money they're still losing money what do they do they go to market or they have somebody inside the company who is one of the three or four investors and they say hey here's an idea have you considered a cram down round or a pay to play around and then they go to every single investor and say we're taking all of the preference stack 30 is owned and preferred they're getting five percent of the company you know that 30 goes down to five you're getting cut by whatever that is 80 percent uh so you go from owning 10 of the company to and by the way it's common shares so you lose all your protective provisions you don't get out first you don't have information rights you no longer have pro rata unless we're in we're raising 10 million for 20 of the company the 50 million dollar valuation right now you've already put 10 million in now to keep up your percentage here's how much you have to put in okay so you want to get back to 10 ownership you know and it's a 50 million dollar company up with 5 million in new capital in and uh then the founders they keep their common uh so they're fine and you know um the whole thing starts over again it creates a lot of bad feelings but it also forces people to put up or shut up but if your fund is completely deployed so jeff what fund is ggv on we're on fund uh eight yeah now notable capital uh so this was from fund two or fund three that fund's fully deployed what would you do jeff if you're faced with this, and I'm sure you've been faced with some of these cram downs.
10:44Now you're in this like very weird, precarious situation. You've got to re-underwrite the thing from first principles. And it's, it's contentious. It sucks. It's hard. And then how do you come up with the number? I've had situations where I own 1 % of the company. They're like, you now own 0.0001 % of the company. I'm like, is that fair? And it's never fair. When you get to that point, people are grasping at straws, right? As you know, I mean, you're in a desperate situation. The founder's desperate for capital. and you have a sharkish type investor who's coming in and saying, look, I could own 80 % of this company, put in$5 million and own 80 % of a company that was valued at 30 million.
11:20But very often what you have is an untenable situation where the company is essentially out of money. In many cases, they've already raised venture debt. They've got to pay a debt provider back. And so you've got a crossover PE type firm that comes in and says, look, we'll pay off the debt provider. We'll buy up a huge chunk of the company. It's a really challenging situation. I don't know about you, Jason. I think we're in the early days of that happening. We're in the second inning because companies raised so much money in 2021 that they've been able to run through 22, run through 23, which was a tough year for most.
11:49And unless you extended your runway for a very long period of time, which Ryan can talk about because he did that, you're now in a challenging situation and you're going to your investors and saying, gosh, this is the only option I have on the table. And it just gets very painful. And some investors have blocking rights to do the next round. So now you're in this like, you want to talk about a game of chicken uh or a standoff you know okay i can block the round and i'm not putting any more money in and we're six weeks to add a cash so i'm i'm literally dealing with i don't know you know we have 400 portfolio companies historically maybe 250 are active i'm dealing with you know a couple of these a month so it's this is a very real thing happening in the market there's two ways to protect yourself you know as a founder and as management team number one uh be profitable number two have a big cash reserve and when the when when the sun is shining you get that hey right and so i literally was on a board call the other day and i'm like we're crushing it shall we put 10 million dollars and sell 10 percent of the business for 10 million dollars or 10 of the business for 15 million dollars would we do that and the person's like we have 18 months of runway i'm like yeah we do let's we're strong raise money when you're strong.
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14:16Head to netsuite.com slash liquidity. that's netsuite.com slash liquidity ryan i guess your thoughts would be interesting here as a founder since jeff and i are out of the game for a little while no i'm glad i'm glad you brought up you know the idea of like the the crammed downs recaps rounds just that have a lot of structure that also make them unappealing define structure for people in the audience who they hear us say structure structure structure all the time what does it mean yeah i mean these are going to be terms where you know for example a new investor comes in and let's say that the founders really want to preserve that billion dollar unicorn valuation and the only person who's willing to give them money at that billion dollar valuation is they're going to want three times their money back before everybody else gets paid.
15:00And that's not unreasonable, is it? To have like, if you're putting money in at that ridiculous valuation? No, absolutely. And there's a bunch of funds who make a lot of money going around essentially just making those types of offers. But what I'm hearing in the market, I get at least one, sometimes two calls a week from other growth stage founders. I have the fortunate or unfortunate benefit of this is my third venture-backed startup. So I've seen a lot of messed up stuff. And so I get a lot of calls. And the most common thing I hear is founders are trying to defy gravity to avoid facing the music.
15:36And so what that means is, for example, is doing a lot of really unnatural things. Oh, if we can just add another$10 million net new, then maybe when we go back out to raise the money, we can clear the last round valuation. But to Jeff's point, which he's done a phenomenal job coaching me and his other founders on, is that doesn't matter. What matters is, are you building a good business? Particularly today, now that the tide's gone out, everybody has a sharper pencil. Yeah, you might be putting up impressive net new numbers, but your CAC's also through the roof. Your retention hasn't moved anywhere.
16:09And those are things that are really just only going to make your business weaker in the long run. So that's another one that I think way too many founders think that, oh, well, someone will do the round. It just might be at terms we don't like. Also not true. There's a really finite amount of... It is so much... And if I put my investor hat on and the 35 or so some odd companies I've angel invested in, That's another thing I hear a lot too. And the reality is many investors and Jason and Jeff, keep me honest on this one. But in many cases, you'd rather cut a check into a clean story without a lot of hair on it and know what you're getting versus going back to the hoop on something that maybe you've been in for a long time.
16:58The terms are complicated, a lot of bells and whistles. And so I think that's another thing that founders really have to let sink in. It's advice I give all the time. It's like, there might not be a round out there for you and you have to operate as if the money is far from guaranteed at any price. So I gave two pieces of advice. Hey, get to break even, have a war chest. You're giving a third, given to you by Jeff, which is have great business fundamentals. Like the business, which I guess is close to what we would call getting to break even, et cetera. But Jeff, the CAC's got to be right because people are going to reevaluate this thing from first principles.
17:37They're going to just re-underwrite it from a blank sheet of paper in these kind of situations. And I think what's happened, Jason, is, as you know, in a zero interest rate environment, people, you know, when you're getting literally zero to keep your money in a T-bill or a bank account, you're highly incentivized to throw money into the market, into risk capital, right? I want to bet on startups. I want to bet on crypto. I want to bet on whatever. When rates went up and people are getting paid 5%, 6%, 7 % or they're getting paid 9 % or 10 % or 11 % in a credit fund, those family offices, sovereign wealth funds, the big giant pools of capital of the world that couldn't wait to pump their money into Silicon Valley are suddenly gone.
18:15And so there's a lot fewer investors putting money into the market. And one of the things that I've been very public about on Twitter is when I got into venture capital in 2008, the US venture capital market was supposedly around$28 billion a year. somehow it ballooned up to$300 billion a year in 21 and 22. I would argue most of that was not venture capital. It wasn't going into seed A and B, series C companies. It was the 10 billion into Stripe at 50 billion. Not really venture capital. That's mid-cap tech. Those are IPOs. Or IPOs. And so what you have is the folks that were doing those rounds or even the growth rounds at 500 or a billion or a billion five, they have the option of buying public companies at those prices.
18:57They can say, gosh, I can buy a public company doing 500 million of revenue at 3 billion. Why would I take a flyer on this private one that has an inconsistent history, a rookie management team, et cetera, et cetera. And so the investor base that is evaluating your deal and your company has more time and they're more discerning. And to Ryan's point, the bar has been elevated. And so the way that they're looking at businesses today, the way that we're looking at businesses is just, we have very high bar and it's a great place to be as an investor. It's why I'm bullish in the next five years. I know you are as well.
19:27But as a founder, my advice to founders has been take the bull by the horns. If you're sitting on the beach and it's 80 degrees out and you're putting sun lotion on, and all of a sudden it starts hailing and it's 30 degrees, don't pretend like it's 80 degrees out and it's sunny. It's not sunny anymore. It's cold. Prepare for the cold, right? Get profitable, cut burn, get your business into a mode where it's attractive to those new investors who have a much higher bar than they used to. But take the bull by the horns, be responsible for your cash runway be responsible for your cap table don't run into a situation where you're passively going out to raise capital and ending up with a bunch of term sheets you don't really want and david i think one of the the situations here is if all this advice is being given for two or three years on you know various podcasts of note quietly in back rooms with uh investors and jeff talking to his portfolio me talking to my portfolio frack gerster out there saying get fit to public companies you know like the weather change the game changing on the field was known for two full years here and and people knew it was a hot market for the last two years of this nonsense and they were saying if you're a founder and you cannot navigate your firm financially uh at scale or you know getting to scale through this, what probably is going to happen is people behind the scenes are going to say this person isn't fit to serve.
20:56It's a hard thing to say because we're such a pro-founder community and being founder-friendly is critical for people like Jeff and I to get deals with people like Ryan. We want to be seen as founder-friendly, but you have to ask if it's been four years, you didn't do any layoffs and you ran this thing off a cliff and you had$40 million dollars in money in the bank and you still burned a million dollars a month knowing all of this well are you the best person to lead the next stage of this company and i think a lot of people would just say no and that's what i'm hearing on the back end yeah i think what's really happened is a lot of those founders that didn't change were basically paralyzed it's people go through crises it's not that they necessarily take wrong action is that they take no action so they've kind of been sitting around to Jeff's point, hoping that more capital will come in and there'll be this kind of Messiah that comes in and saves them rather than doing the difficult things.
21:51And the difficult things you have to wake up every morning. I've been a founder twice and you have to eat that frog, do the difficult thing every day. And then the next day, do the difficult thing. It could be 18, 24 months of eating crap until you basically are able to be above water. Juggling multiple devices and apps to run your business is a mess. Open Phone is here to make it simple by simplifying your business communications with one easy to use app. Open Phone has rethought every detail of what a modern business phone should be. And here's the magic. It works through a beautiful, elegant app on your phone, or you can just use it on your desktop, making it super easy to get a business phone number for your entire team.
22:32And you know how brilliant open phone is? My teams use it every single day. My sales team loves it. My ops team, they use it all day long. And here's the features that we love. You can create a shared phone number like customer support with multiple employees fielding all the calls and all the texts to that one number. At my investment firm launch, we pride ourselves on replying to every single call or email instantly. And open phone is the number one rated business phone on G2 for customer satisfaction. action. So here's your call to action. Super easy. Open phone is already affordable. Starts at just 13 bucks a month.
23:05But twist listeners get an extra 20 % off any plan for the first six months at openphone.com slash twist. And if you have existing numbers with other services, no problem. Open phone is going to port them over easy peasy lemon squeezy, no extra cost. Head over to openphone.com slash twist to start your free trial and get 20 % off. Ryan, you're in a really interesting position in that you raised almost at the height of the market. October 2021, you raised at a billion dollar valuation, raised$90 million. Then you kind of started to see the market. How did your operations evolve as the market changed?
23:39Wholesale changed across the board. I mean, so exactly to the point that all of you are making. And Jason, I'm glad you brought up the point that you just did. I ran into one of the partners at Diverse at an event. And he said, we're doing more CEO searches than we ever have in the last decade. And that's because at some point, your investors, your board, they're going to be sitting around the table and they're saying like, yes, you're an operator. Yes, you're a founder, but you're a steward of this capital on behalf of us and our LPs. You have a real responsibility to figure out where does the next incremental dollar need to go or not go.
24:20And I was just having this conversation with someone internally. There's a company that I won't name, but doing low nine figures. ARR raised a lot of money at the peak, had never done any layoffs. Staff would openly admit that there was a lot of bloat. And they announced a 5 % riff. The 5%, my COO said, he goes, that'll get rid of the Cheetos in the break room and not much else. I mean, it's no man's land. And so it's not just about making changes, but are you actually making the changes to an extent that they're going to make sense and really bend the arc of the business? And I think it's doubly hard when you're coming off the sugar high of raising money every six to eight months at a huge uptick.
25:10Never had to worry about money, at least for years and years. And yeah, correct. In our case, we raised over$100 million across two rounds between the end of 2021 and early 2022. Four months after we raised our Series D extension, I went back to the board of the investors and said, we're going to do our first riff. And then we did another one and then we did another one. and then we we committed to completely rewiring our go-to-market motion completely reimagining the product and the feature and functionality all of that to really guide us in a direction where we could still deliver on the mission of the company but we could do it orders of magnitude more efficiently and more effectively than we were doing it before i had to learn that the hard way my first two companies even though they both had small but successful exits were weeks away from running out of money.
26:05And what I knew coming out of those experiences in my first two companies is it's always in the final days when the movie's almost over that you go, oh, but we were just starting to figure it out. We were just, I mean, how many times - Let me ask you a question, Ryan. You did three riffs. When you look back on it, should you have done two? Should you have done one? Should you have ripped the band-aid off quicker? And then take me through the psychology of being a founder and how absolutely arduous, painful, and how much suffering goes into doing these reductions in workforce layoff. It's unbelievable.
26:39And obviously, we would have loved to have just won and done. I mean, that is always, you want to cut deep, you want to do it once, and move on and be able to focus and know you have the team. I think the difference with us is we were going from a model that was sort of a mix of software and services, a big inside sales model, to really reimagining this as pure SaaS, bottoms-up, product-led growth. And so it wasn't clear until a little bit further into the cycle exactly what the go-to-market mode, exactly what the 2.0 version of the business was going to look like. Only then did it become clear, hey, here's a cost structure that makes a lot more sense with what we know the business is today.
27:26And I don't think that... Not every business has that problem. I will say though, I think that there are a lot more companies out there that need to do a much more wholesale rewiring of how they make money, how they serve their customers. I think we all know it's like, yo, you can't cut your way to growth. You can and you can't. You can't cut your way to growth if you're just going to do the same thing you've been doing for the last 7 years with less money. if you commit to running a more efficient business and you and you commit to the product and the organizational change to do that you can absolutely spend less money and actually and grow faster and this is the high degree of difficulty ryan and jeff i would like your input on this because you and i were former founders who are now capital allocators you know you're being asked to cut costs and at the same time innovate in product uh and then increase sales and so So seemingly, this seems like, well, these are counterintuitive.
28:24Wait, we have to invest to get growth. It turns out, slowing down, getting rid of excess in an organization, and excess can come in many forms. It could come in just undisciplined marketing spend, undisciplined product development, whatever it is, undisciplined T &E and office space, whatever it is. But if you start getting efficient, and then you start having constraint, what you find in an organization is uh people figure out how to do things quicker and this is one of elon's tricks is he just says you know they're like oh this is gonna take six months he's like okay i give me a way to do it in six um days and i'm on a board right now and they showed me it's a it's an e-commerce company which they which one and they're they they stayed away from amazon for a long time they believed in building direct but they they had competitors and knockoffs just crushing it on amazon so we could not not be on amazon so we said okay we have to have an amazon strategy out of the gate it goes explosive and so they're like we're going to double amazon next year and i said hold on a second we're going to double amazon next year give me a plan for 10xing amazon this year and they were like what i'm like yeah we're starting from a very low point it's low single digit percentages of our sales give me a 10x show it to me in 10 days and then 10 weeks after that i want to see if we hit 10x or not and then i want to plan to go 10x again and you know most times that unrealistic thing i you know um you would think on its face jeff you know you seem like a lunatic you know what it did it worked inspired people and it worked yeah and people are like wow we we think we got a 5x from this we found this other thing there's subscribe and save you know we didn't realize how big amazon is in this other geo we found this consulting firm that said we can do coupons and we discovered coupons and i'm like this is what i'm talking about Let's do less with more.
30:17And I did the same thing with our team. I want to meet more founders. I want to do more introductory calls. Because I believe deal flow is your destiny in this business. So I said, how do we do 100 first-time calls per week? Oh, my God. 100. I mean, look at Jeff's eyes. 100 calls a week. We're a 21-person firm. That's great. It's just a lot. It's a lot. 70 people. I said, okay, here's how I want you to do it. Call it an introductory call. Tell the founder we don't want to waste their time. Framing matters. It's only going to be 15 minutes of them presenting their company and five minutes of us explaining to them how we invest and making sure we understand their vision and then determining if a second call with a more senior person is a good idea for them because we don't want to waste our time.
31:00So we reframed it. You know, shout out Scott Adams, creator of Gilbert. We reframed it. He's big on reframing, but that's a concept of psychology for decades. You know, to be only 20 minutes. Well, now, if it takes an hour to write the coverage or whatever, you know, round up to two hours of work for an associate or a researcher. Okay, yeah, they can do three a day, four a day. Okay, so now you do 15, 20 of these a week. Okay, how many people do you need? You need five people. Is that possible? I did 70 last week, 60 or 70. So I'm almost to 100. It all goes in a database. It's going to be pretty good for returns.
31:37It's a game changer. It's a game changer. The other thing I'd add, Jason, you know, Ryan gave some great context into what he did. I think the broader, some additional color I would give on his scenario because I was involved with it day to day, but he has a great set of advisors around him. He has Dick Kossel and Adam Bain, who used to run Twitter. He's got Tim. We've got a CEO on our board. We've got Emmanuel Scala, who was the chief customer officer at Toast. We've got Bob Goodman from Vessemer and myself. Ryan's got a good sounding board of people. And as we were heading into the late stages of 21 and into 22, he's raising all this capital.
32:14He wasn't afraid to call us either and say, hey, guys, there's some things in the business that aren't working. And I think we should put them on the table and talk about them. That led into that summertime conversation in 22, Ryan. I remember when you called me and said, hey, I think we got to blow this thing up. Like we got some things that are just not working in this business. And I want us to be in five or 10 years. I want to be a higher margin, higher growth, channel driven business. And here's how I think we should do it. a lot of founders are afraid to have that conversation with their board and with their investors.
32:42And so a lot of credit to Ryan. Some of that's being a third-time founder to have the confidence to do that. But a lot of it was building the relationships with those people over the years. He didn't just pull that board together in the summer of 22 off of some angel-less recruiting site. He had carefully handpicked these folks over years and built relationships. And so when the time came to really deal with this sort of like wartime mode, He had good people around him. And one of the things I see in the market today is I get these founders coming to us, Jason, at Series B and C who are still burning a ton of cash.
33:14And I say, well, who are your mentors and advisors? And they say, gosh, do you have any recommendations? They don't have anybody. They have nobody that's giving them good counsel. And in many cases, they've got junior investors on their board who aren't giving them great advice. And so it can be a really challenging and lonely place to be if you're a CEO. So one of my main pieces of advice, I know, Ryan, you share this with folks all the time, who are at Series A and B is cultivate those relationships with advisors, board members, people who actually want to have an interest in helping you be successful because you may not think you need them today when things are going well.
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33:49But when you hit stormy seas, it's invaluable. I don't know, Ryan, if you want to add any color to that. But to me, it was a huge part of your process. Yeah, absolutely. But the other part of it too, though, just kind of Jason, go back to your comment too, about when you throw that audacious goal out there, like Jeff, something you talk about a lot is just creating situations where there's nowhere to hide. And that's one of them. When you go to a team and you say, Oh yeah, I know we only put 100 customers on the new product last quarter. So this quarter we're going to do 1 ,000. You don't have any more money or any more people to do it.
34:24The right people are going to jump out of their chair and be like, I don't know how we're going to do it, but man, we're going to go try. And the wrong people are going to kick and scream and come back to you the next week with all the reasons why they can't do it. But now more than ever, as companies are making changes like this, that's one of the things that I think... And it's a piece of advice to give to other founders. That's what you need to ask of your people. It's not about the little incremental improvements each quarter. If you're going to reduce costs, let's really reduce costs. if we're going to launch a new product we want to scale quickly like let's really figure out how uh you know how far we can take it and and all of that is is made much much easier by having people around the table who are ex-operators who bring a diversity of viewpoints and um you know in my case seven out of ten times i bring a question to someone like a tim or emmanuel on my board they might just agree with me or kind of repeat that but it's you're building that muscle memory and that validation to trust your instincts and make decisions faster.
35:28And so I think all of these things are critical right now. Listen, we all know generative AI is revolutionizing every industry. In fact, we talk about it here on this podcast every week. And companies that are slow to leverage this technology, well, they're going to risk falling behind their competition. But new innovations also bring new threats. How do you safely accelerate your company's gen AI adoption while also managing the risk? Well, let me tell you about Hidden Layers AI detection and response platform. It's a security solution specifically designed for generative AI and large language models, LLMs, you know that.
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36:36So here's your CTA, the old call to action. With Hidden Layer, go from pause to possibilities and step into the future of secure AI innovation. Learn how to protect your Genitive AI today by visiting hiddenlayer.com slash twist. That's hiddenlayer.com slash TWIST. Speaking of cutting costs, United's CIO, Chief Information Officer Jason Birnbaum is going all in on AI. United is reportedly using AI for everything from chatbots to pilot announcements and will be piloting AI applications across the entire company. Ryan, you're founder and CEO of electric.ai, you were early on the AI thesis, and you help small businesses integrate IT solutions, including AI.
37:21What are you seeing across the thousands of SMBs that you service? My guess is that this airline CEO, a year and a half ago was all in on Web3. I'm half joking, but I'm somewhat wary of people that make big, splashy public announcements. I am not poo-pooing the commercial applications and the potential business transformation that a lot of these new tools can bring. Specifically for us at Electric, we're making IT really easy for small businesses. They don't really care how we do it. They care that it gets done. They care that they can click a button and the computer gets provisioned and sent to the new hire.
38:07They care that they can click a button and we can tell them a whole bunch of things about how they can make their environment more secure. I think AI for the time being is certainly a useful buzzword. It's a useful hook. It's getting a certain type of early adopter SMB customer into our funnel. But specifically on this end of the market, if you do a great job with your software, it kind of disappears in the background. And so I think ultimately, one of the things we talk about a lot internally is that AI didn't all of a sudden overnight change the fundamentals of product management. You start with the problem and work backwards.
38:46And I think there's a lot of great things that AI can do to accelerate the solutions that you want to deliver to your customers. Beyond that, I think I probably have a bit more skepticism than some people. I'm very curious, Ryan, you've fractionalized IT services for electric. Do you see the fractionalization of AI in the future where large companies will have their internal AI teams and tools, but you'll see SMBs benefit from broader platforms? Yeah, specifically, I think like vertical SaaS and SMB vertical SaaS stands to gain the most from AI, as we've probably all seen playing around in these LLMs.
39:20They do much better when they can index something more specific than the entire internet, right? So when you're dealing with a constrained set of problems, a constrained set of intended solutions, and like many vertical SaaS companies, you're sitting on a pretty juicy proprietary data set. You can do some really cool stuff with that. And you can produce, I think, extraordinary customer outcomes. So that's the part I get really excited about is I think a lot of these companies don't need to be built new from scratch. I think there's a lot of great companies that might have been around 7, 10, 12 years that are actually in pole position to become the next great AI story because they have a 90-yard head start with an existing solution, existing data, existing set of customers.
40:09And now with the air cover of all this macro uncertainty and a lot of businesses rewriting the way they do things, this is a great time for a lot of those companies to reimagine themselves and what they can do with this technology. Jeff, I see you nodding your head. How do you see enterprise companies integrating AI? Yeah, I think, look, Ryan makes a great point about companies wanting to sort of jump onto the bandwagon. We see this in venture capital. You go back a decade ago, and there were folks creating funds dedicated to mobile apps. There were people who created cling tech funds that sort of were there and then went away.
40:44So I think, look, I've been in Silicon Valley since 1995. You get these paradigm shifts every decade or so. We had it with dot-com and the internet. We had it with cloud and mobile. I think this is a massive paradigm shift. I think this is probably bigger than those because the world is ready for it. The infrastructure is there. The compute is there. If you think about the S &B segment where Ryan plays, one of the reasons we're so bullish on that segment, it's 42 % of US GDP. It's 55 % of US employment. Because SMBs 15 years ago didn't have any technology. Most of them didn't even have internet access in their shop.
41:23Now they're running Shopify for e-commerce. They're running Square for payments. They're running Toast inside their business. They're running Homebase for payroll and time clock management. They've all bought technology. And the layer is there for now, to Ryan's point, for the incumbent vendors to roll out AI features and modules that make those businesses more productive. I think one of the cool things there, it's not going to be a headwind for labor. In big tech, we're definitely seeing a headwind for labor because of AI. We saw that Jason mentioned the efficiency wave with Zuck and Elon and others.
41:56And I think everybody's gotten religion around the idea you can build much bigger companies today than you used to with less headcount. In small business, if you take the average 10-person shop, the owner is doing accounting, the owner is doing finance, the owner is doing sales, marketing, payroll, etc. etc. So when you give them an AI tool built on top of their existing software or a module on top of their existing software that can do those things for them, it's going to make that shop that much more productive. It's not going to allow them to eliminate headcount inside the shop because nobody's doing those functions inside the shop.
42:27If you take that 42 % of US GDP in America, and you give it a 5 % or 10 % boost because of AI, that's huge. That's huge for our economy. And so one of the things I'd love to see us get the narrative out, there's a lot of negative headlines around AI, it's going to reduce labor, the robots are coming, et cetera, et cetera. I'm not saying those are valid questions. I just don't know why nobody's focusing on the potential benefit of this technology, particularly to small business, which is almost half of our economy. I think it's going to be huge and we're betting big on it. I think for LPs, it's a category that will generate a ton of returns.
43:02As Ryan mentioned, it'll probably come from companies we've already funded. But one of the challenges in the venture capital world today, it's not that easy to go fund new ideas and AI other than the infrastructure space. In the application layer space, it's a little bit hard to imagine a brand new company today coming in with something with AI that will displace a, call it 100 million ARR business that already has thousands of customers because they're rolling out that same functionality. It depends on the category. It depends on the category. Yeah, I might take the other side of it. I think it's a low probability that somebody coming in with an AI first solution displaces the incumbent, but it's possible.
43:36And so, you know, when they do, it'll be big. Yeah. Yeah. Or they can, you know, M &A can, can take them out. So it's just such a transformative technology. And I don't see a world in which all workers do not become a minimum of one or 2 % more efficient every month because of it. I'm picking the lowest possibility, 2%. that means every 35 months everybody's twice as good at their jobs just take the rule of 72 right um now if people were you know became you know five percent six percent maybe even seven percent better at their jobs every month which i do think in certain jobs is not just possible but probable we can all think of a developer getting seven percent better every month at writing code we can all think about a writer or a researcher or an sdr or an account executive getting seven percent every month that means every 10 months or 10.2 months you can look up the rule 72 they're gonna get twice as good at their jobs and so this is why i think it's it there's you know like all these hype waves whether it's mobile broadband cloud you have this weird you know overhyped underhyped you know moments that happen overfunded underfunded um you got to take a relentless paced approach to this as a founder for those founders who are listening and as an investor i think you just have to let the founders show you how they're using it and then look for those those clues we have an incredible company called podcastai.com and they did a very simple thing for us and the podcast the liquidity pod.com uses them and uh so does this week in startups.com it started with taking every episode transcribing it by the way that used to be a 500 to a thousand dollars per hour to get a decent transcript you know then it became an international thing and it because it used to be like five dollars a minute here ten dollars a minute in the u.s international made it one to three dollars a minute using people in manila but you know had error rates now it's getting better and better and better now it's telling us the chapters in each of these then it's giving us what clips we should do now it's uploading those clips to twitter and linkedin for us so you start looking you know every quarter this company pockets ai.com which we've invested in three times they release something that we buy i pay 500 a month for this and i'm like charge us two thousand a month thousand a month and we'd still pay it but anyway and then our producers here at this podcast and you know uh and at this week in startups they free up 10 hours a week well what can they do with that 10 hours they can do better research uh for each episode they can book better guests there's always something to do to make this better um and then they came to me today and they said oh by the way um if you tell us who your next guest is we're going to go out for all the web find the podcast youtube videos social medias of that person and build you some notes and i'm like okay here we go now this idea of getting seven percent better a month at being a podcast producer is here and who are they going up against a wordpress site is what we used to use but it didn't have any of this functionality the wordpress site was just you know shout out to my friend matt mullenweg and brian alvey over there fantastic the greatest publishing platform in the world but you start thinking about a niche like podcasting and then you put ai on it and you have a team of you know right now they're three people but they were 30 people oh my lord like what they're gonna do is just gonna you know free us to do so much more work so i am over the moon with the application layer imagine every small business in america you're you're running a 500 000 a bit small business that does 500 000 a year and you get a 10 bump in cash flow because you're better at sales and marketing, you're better at finance and accounting, you're saving money on your taxes, that 50K almost just sort of appears out of nowhere.
47:31It doesn't hurt anyone. Where does that 50K get spent? It gets recycled back into the growth of the business, potentially gets recycled into more headcount. So I just think long term, I put a long thread about this on Twitter, I started writing and just kept going. I just don't see how this isn't a huge tailwind for our economy. I feel like this paradigm, and you and I lived through the dotcom era, ryan i'm not sure how old you are if you did but i feel like if you take all the different paradigm shifts we lifted live through and i lived through the pc era which was after client server and the cloud era the online era broadband era mobile era cloud era i think that's all the eras and then ai it feels like this is the culmination of all the in other words everything has been a setup to this point and we're seeing and we're funding companies in the precede stage that get to 250k in revenue per year with two people three people and they're like yeah i'm like how much you're gonna raise and normally it would be three million dollar seed run and they're like yeah how about 500k for five percent and i'm like well if you're gonna go out and raise why not raise two million like i don't think we know how to where we spend it oh whoa that's a very interesting moment for lps and vcs to noodle on maybe they don't need as much money from us maybe we're the problem maybe dropping too much money into this you know system the same way in america we dropped too many calories on america and 60 70 of the country got fat who's responsible for that you know big ag we had a really great idea there was this thing called dwarf wheat and they did these wheat studies of how to get more calories out of a hectare um you look up the dwarf wheat studies i think it happened in mexico and all these great scientists came together into all hybrid versions of wheat and the book wheat belly and other things go over they were so good at concentrating calories into the wheat chaff that they made it so fat and the husk so then that it made it a super wheat that wheat spiked your blood sugar and made you fat and the reason they call it dwarf is because it was so fat the husk that it would break the long strand of a wheat like you know amber waves of gold kind of situation so they just said oh let's just make them shorter so they don't fall over.
49:41Sometimes you can just make something so efficient that it makes everybody fat. And the reason we're fat today is just bread and calories and cereal. When you started talking about super wheat, I thought you were talking about something else that's very popular here in California. A whole different economy. But it's a great point because if you think about it, my first company started in 2007. Okay, back then, it was impossible to raise money. If you did raise money, maybe you raised a few million bucks. Maybe really big. raised like 10 or 20. And that was like the absolute most. And like, there was a time when we all believe like software is efficient.
50:17Software businesses have these big margins and you can, you know, and I think there's almost kind of like it's come full circle in that sense, because, you know, Jason, to your point, it's like this culmination of all these different eras, right? Like this, you know, and Jeff, to your point about the productivity increase, right? Like this isn't an AI headwind that's going to negatively impact the average and worker like this is an ai stimulus that no one's really talking about yet and back in the 99 2000 era we raised money to build data centers we there was no aws we ran little mini data centers all over the country that's where the money how much did that cost cost a fortune right it cost a fortune what did it cost per startup to put up your co-location it was so expensive it was so we weren't even the world sass hadn't been invested invented we were an asp back then but you had to raise capital to buy hardware build your own data centers pay for the bandwidth and then amazon came along and solved that for everybody so i just think this is the net this is knowing what we know now about how transformational aws was it's hard not to look at this wave and say gosh this is going to be a huge turbocharger for our economy i just what aws did yeah that went from i think the average startup probably spent 500k in the first year to set this up about 250k service i know we did at mahalo when i did my last startup mahalo we spent about a quarter million dollar putting servers together and putting bandwidth together at a co-location facility plus you had to have two sys admins sys ops people so you're at about a half million dollars and then steady state probably a half million dollars a year so first three years we probably spent 1.5 million our friends at microsoft uh our friends at oracle um they're being really aggressive and trying to get into the startup community i've had good relationships with both of them um they'll offer our startups you know 100 000 250 000 in credits and that covers them for the first five years so it went from 1.5 million over three years to free i mean that's extraordinary and just going up a level jason you know david you mentioned lps how are they looking at this whole ai universe and there's been a lot of capital thrown into the infrastructure layer all that money that is being spent on infrastructure not only by amazon microsoft Google, etc.
52:33But some of the newer companies, OpenAI, Anthropic, and these other companies are raising capital, is going to benefit the startup community that we're talking about. And I think the output of that, one of the reasons all of us are bullish on the next three, five, seven years, you're going to have more well-run companies that need to raise less capital. The founders are going to own more. Investors will get a better return on their capital. And the outcomes could be bigger. We should have more profitable companies where the outcomes are bigger. Because some of those infrastructure companies today are absorbing, they're going to spend a lot of money.
53:05I mean, one of the challenges Sam has publicly talked about with OpenAI, he had to go out and raise billions of dollars to build out the infrastructure for OpenAI. It wasn't doable on a shoestring budget. But once all that infrastructure is there, it's kind of what Level 3 did for the internet way back when. Go back 20 years ago, somebody had to build out all the bandwidth that we're now running the internet on. And it was very expensive and there was a bubble and it popped and level three stock tank but the output of that was there was fiber everywhere and we take sort of gig to the home for granted but you know wind back the clock 15 17 20 years ago you couldn't get fiber to the home yeah look at this the headline you just put up all that fiber that people thought was crazy yeah 2002 people thought it was crazy and today it's all getting used and think about all the amazing things that are happening in science and healthcare and banking and all these other things.
53:54We're in the first or second inning of even understanding what this next wave of AI is going to do. You know, they overbuilt fiber to the point at which the companies went out of business. Yeah. They invested so much and they couldn't sell it. They went out of business and then Google and other folks bought this fiber up. It became, there was a term, dark fiber, fiber laying around. Jeff and I are all of them to remember these days. Yeah, yeah, yeah. um and the the the paradox the irony was internet traffic they were correct internet traffic continued to grow who was the beneficiary the beneficiary of all this was youtube and netflix dropbox you couldn't build applications like that in the 90s in fact my friend mark cuban who did broadcast.com said youtube and netflix are insane it will never work they will break the internet and in some ways he was right if everybody had gotten onto netflix at the same time youtube at the same time and it had gotten to where it is now but we were able to keep up with it a lot of other things happened with compression and storage and plumbing costs of storage but sometimes it overbuilt in a glut it kind of makes people be like oh yeah you know i can get uh truffles and lobster at a lower price yeah let's make you know lobster sandwiches for everybody and we'll charge 20 bucks like if there were too many lobsters available and you know in new york at the turn of the century lobsters were so available it's what poor people ate they were considered like the cockroaches of the ocean and they take them out of the east river in the 1800s and that's what poor people ate because everybody else is like oh my god you want to eat those things those bottom feeders like nobody wants that supply went down they became elite uh items but it's really such a great thing and i just wonder are we going to be sitting here in two or three years and there's h100s and data centers everywhere and the software developers have figured out how to build these language models so efficiently and small and in verticals that you don't need all this um and you know people like grok doing inference so well and efficiently they you know get rid of 99 of what people need in terms of compute this could go in the opposite direction if we overbuild so i am fascinated to watch this um one of the things i think with these generational transfers is that every time the game changes you mentioned the early 2000s is about who could fundraise five,$10 million pre-product.
56:19Then it went to the engineering phase where it's who could build the best product. One of the inevitable things that I think we'll see in the next five to 10 years is who could distribute their product in the most effective way. You see the rise of influencers, you see other clever ways to hack distribution. I think will be an inevitable battle line once you have products that are able to scale very quickly and very cost effectively. Well, one of the reasons I love where Ryan is sitting is he is sitting at the epicenter of the way small businesses buy software and technology. If you wind back the clock to why Bessemer and Notable and a bunch of other good firms got excited about his vision, it was, here's a$500 billion category where small businesses spend on technology and we're going to sit at the center of that.
57:02And Ryan, you mentioned earlier, we're joking that you bought the domain for$50 because nobody was buying AI domains, but you were ahead of the curve. And I think we're seeing that today. a lot of businesses that we're pretty excited about at series B and C and D got started seven, eight years ago and made the bet on this AI trend before it was cool. Yeah, exactly. And also, Jason, your point about YouTube, for example, being the beneficiary of kind of in the dot-com era, everyone laying all this fiber and building the infrastructure. I think folks in the application layer, we're going to reap a lot of benefits of a lot of the money being put on the ground.
57:36Now, I mean, one thing we've talked about internally here is if you think about like who was the biggest winner as a result of refrigeration technology it wasn't the refrigerator companies it was kookola should give us another minute to figure that out who was it i was gonna think ice because ice you know you had to um there were people who were taking ice from canada or something cutting it up or whatever putting in boxes and putting in boxes there were ice delivery so like then all of a sudden you could make your ice at home and that was like pretty crazy i'm also wondering if like meat and milk going bad and you know you can have your milk for longer but that's more efficient on the consumer side but yeah coca-cola yeah stuff like this warm coca-cola is awful right and so with that ice cold coke is delish yeah and so i think you know all of this stuff to me it kind of feels like a a tale as old as time right you know you look at sort of like the size of a computer that would be you know needed to to do basically what a Casio watch could do today.
58:39It's the same. I mean, how many times has this cycle repeated itself? I think the other point about some engineers somewhere are going to figure out how they can operate their own models with vastly less compute. That's probably something that will happen. And again, I think folks in the application layer who are solving very specific, often vertically oriented business problems stand to be some of the biggest winners. And it's all tied together in the economy, right? I had lunch yesterday with a guy who started a chain of restaurants. He's got several locations in the Bay Area. And he was telling me how he started his business pre-pandemic, but just as DoorDash was starting to get scale.
59:21And he said, I don't know if you could build my business today without that. I rode that tailwind on Uber, Uber Eats, DoorDash. We built a social media business where people understand what our brand is. We're doing a lot of volume. has a location in San Francisco that the area no longer has as many people living there, no longer has people coming into the office. And so the foot traffic went way down, but their door dash traffic has gone way up. And so there's just, there's all these interplays in the economy that I don't think we quite understand yet. I think economists are really, you know, everybody's projecting recession for the last two years.
59:52It didn't happen. Why not? People are having a very hard time getting their head around all these different variables. We've got a record number of people that have started small businesses, right? 10, 15 million small business applications in the last three, four years. We've never seen anything like it and nobody can get their heads around it. Well, guess what? They've got Shopify, they've got Square, they've got all these tools and technologies they can use to launch a business today. So it's just, I just think we're in the middle of a really interesting timeframe where all these things are connected.
1:00:18And AI, Jason, back to your point about productivity, it's gonna be a turbocharger. It's gonna be like lighter fluid on a fire that's just getting going around technology. It's gonna be, it's a good reason to be long. Having said that, I do think we're just entering into the it's over hype cycle. so back half of 24 it's overhyped stocks are going to take a hit people are going to be on tv saying all these guys have no real ai yep and then in 25 and 26 you'll see these things that come out of nowhere and everybody's like oh my god i can't believe all the success i think there's like a major macro discussion that has occurred for the past two or three years that we're going to need to reset going into 20 or as we wrap up 2024 and go to the back fact nine which is wait a second all these layoffs were done companies got stronger we thought that earnings were going to go down but earnings are a function of how much you spend to make money and the earnings are doing fabulous and the efficiency means you can be uber and uber i think didn't add any employees for two years but they keep growing 30 percent and you know obviously we saw what happened at x but meta getting rid of 20 or 30 000 people i'm not sure what the exact number was and you know he's going to do it again there's a rumor he's going to do another 10 it's like already you you five extra stock from 92 where i bought it up to 500 or whatever it was it took a little hit today but there's a macro discussion here of how come unemployment is so low how come inflation you know gets to three percent we can't get it back down we're still at five whatever we're at you know in terms of like the rate cuts and we're not having rate cuts like what is going on in the actual economy in america that you know it feels like people should be in a panic and then i open up like tiktok or twitter and i i start seeing because i like to look at layoff talk which is like a very specific tiktok um because i i like to have my finger on that because i'm i'm hiring i'm gonna i'm gonna hire three four or five people this year um and i'm investing in our business i'm like hmm These people are saying they can't find jobs or that they're finding jobs that are 50 % that are offering 50 % less salary.
1:02:29And I'm like, huh, so that's what's going on here. It's not that the economy is going to crash or something. It's that I think leadership is taking it really seriously. This, you know, get fit movement that Brad Gerstner talked about a whole bunch or that Elon kind of led. And I think Brad kind of named it after that and then pushed Zuck to do it. And he did it. Now it's got all this momentum about getting fit. you know part of getting fit is saying you know what we used to pay 150k for your position but we can have somebody out of school do it for 70 and you know what there's people in portugal and manila who will do it for 35 and that's a very weird thing that occurred jeff because you mentioned remote work essentially i think what remote work is such a major driver of this what lead what leadership figured out during covid i know i did was that you know hiring somebody in another country who doesn't care about stock options or carry in a venture firm like this they don't have this in portugal or manila whatever so that's like they don't even want it you would have to like spend months explaining it to them for them to even care about and they probably wouldn't they would think it's some kind of a scam putting that aside i have uh two virtual uh folks i'll talk about this another i'm gonna make an announcement about this virtual investment i made next week in a virtual uh assistant company and i'm the first investor in it um but i don't want to spoil it yet i'm gonna announce next week and this company um we have two virtual assistants for 36 000 a year each and then i compare them to entry-level americans and they're both in the slack there and they cost half the price and somebody else manages them and trains them and if they don't work out they give you a new one next week and i'm like huh i don't know there's about a third of jobs i could see these folks doing uh what are the constraints jason so obviously they could replace many other functions but what functions could a remote not replace you tell me you know because how much of what we do is in person now and did you see the uh new york there was a restaurant that had a uh you know the standard you said you're an investor in toast by the way jeff no but one of the former exec from toast is on the board of electric with ryan emmanuel scala she's terrific i mean think about how toast just has changed the restaurant business you don't need waiters you just transformational transformational and by the way if you've got kids and you got to order an extra round of dumplings trying to flag a waiter down for 10 minutes is death but ordering it and getting it to your table in 10 minutes is life you know especially when you know two eight-year-old daughters are fighting over who got the last dumpling they had a person from manila philippines somewhere or india it's like 1 a.m their time they're taking new yorkers orders over zoom they're literally just in a zoom window and zoom basically 24 hours a day for free and so you could order from the kiosk or you can order from the woman on the computer okay that person's getting paid i can tell you what people in manila get paid cashier manila gets paid a dollar an hour um a serious person you know with a college education gets paid five an hour so you start thinking you know ten thousand twelve thousand a year is like what a college educated person gets two or three thousand dollars a year is what a cashier would get a non-trained person a very you know entry level first run so um yeah it's kind of nuts and if a restaurant can figure it out what's happening in corporate america ryan i just hired a phenomenal executive assistant in the philippines he's fantastic on top of things uh hard to imagine going back and yeah got us thinking internally you know what what yeah what What else is there?
1:06:27And I think when I moved back to New York City in 2016, Google had that big office over meatpacking. And a couple of friends who worked there, said, Oh, come by, we've got this sushi chef and all this stuff. And we go over there and there's a table full of product managers bragging about the fact that they can't remember the last time they did any meaningful amount of work in a given day. And they're all making$500 ,000,$600 ,000,$700 ,000 a year. And I think rightfully, that was the biggest heist in tech for a long time. It's like, I'm just going to go there and hang out and do nothing for a while and make way too much money.
1:07:04And then people are surprised when those jobs start evaporating. So I think there's going to be a flight to quality. There's going to be a flight to what are the things that you as a human can do and you can do better than anyone else. But even for us, we've got some phenomenal stateside engineers. We also have a lot of excellent people in Brazil, both ICs and engineering managers. And so it's hard for me to imagine a world where to be competitive, you don't think globally and don't think much more holistically about where everyone sits and what that means for the business. And that process of working with those folks overseas has gotten so smooth.
1:07:44I have another company that I'm involved in where, Jason, back to your point about setting aggressive goals, I remember we were having a December board meeting and the founder said, we want to move all of our basically front end lead gen and go to market to this other area in Argentina by June. And several of the board members said, well, why don't we do it by April? And he said, well, that seems a little crazy. We got a lot of this. And ultimately he said, you know what? Let's do it. We'll do it by April because we're going to learn in that three month window from April to June. We're going to make some mistakes.
1:08:15We're also going to learn a ton. Guess what? Rolled it out, did it, cut their tack in half. It's going to be the reason that he's pointing the company towards profitability later this year. So, savvy, sophisticated founders, they're not waiting, they're figuring this stuff out. AI is going to play a role, offshore is going to play a role, and all of it is connected because of remote, right? We are now much more comfortable as a society working remote. Think about our industry. I mean, we're a tiny microcosm of the universe, but how much more effective are we as investors meeting people over Zoom than we were five years ago?
1:08:47I remember driving around San Francisco, walking up and down streets, you maybe met two or three people in a day. Now I can meet five or six founders in a day, half hour, it's better for them, it's better for us. If there's a great fit, we get together in person. I met somebody today, we're getting together tomorrow in person for lunch. It's a way better model. It's way more efficient. You apply that on a bunch of other industries that really matter to our economy. And I just think it's going to be not only the virtual piece, but the AI piece is going to be a huge tailwind. And to your point, Ryan, how much time did you spend raising money for your startup pre-COVID and like going to Santo Road and taking meetings you even in an aggressive day where you said I'm going to do four meetings a day you know that's a lot and you'd have a driver and you would be you know two hours at Sequoia two hours at Kleiner two hours at my last company it got to a point where my co-founder I said he goes literally he's like you need to stay in the office and run the company I'll go handle this because even at the seed stage it was a full-time job and you know every every round you know at electric covid you know onward was hop on zoom do the thing get back to work yeah i mean and you had this weird thing where as human beings if you're going to fly out for a meeting well of course i'm going to take you for a meal of course we're going to have a meeting and we probably should do one other thing so you flew out i mean to fly out and do a half hour meeting be like bye i mean it was like well ryan ryan ryan can attest to this he crushed me in soul cycle before we invested oh yeah well i'll give jeff a lot a lot of credit i think he emailed me on a monday i said hey i think the round's coming together quickly he's like we can be there tomorrow to take you for dinner i said hey well i promised the team i would go with them to soul cycle after work he goes i'm there love it we had the little barbecue uh we had a little barbecue steak and and uh and soul cycle and ryan ryan put thankfully there was somebody else on the team i'm a larger human being there was somebody else who was my size who rode in the back with me we i didn't have to be too embarrassed to there under the candlelight at soul cycle but ryan was clocking you know however fast you were riding while i was in the back huffing and puffing well what matters is you might you might have lost the soul cycle class but you won the deal yeah i was gonna say that's how you know around is truly over subscribe jeff when uh when you get beaten in soul cycle yeah yeah it was fun though on that note uh let's wrap up uh with With Jeff's latest three investments and also Ryan, you can tell the audience a little bit about Electric and what you're looking for in the market.
1:11:14Yeah, Ryan, you get a full plug. Go for it. Tell us about the company, who your customers are, and who you're hiring. Thank you. Yeah, Electric is the easiest way for small businesses to manage IT. You want to manage your devices, software, get more secure. We are designed specifically for companies that don't have any in-house IT staff. So if you are a small business and you care about the security of your employee and customer data, and you care about your staff not wasting time doing things like buying and provisioning computers, go to electric.ai, check it out, sign up for our freemium product online.
1:11:53And anything else you need, I mean, feel free to hit me up directly. I'm very easy to reach and we love our customers. Who are you hiring for? you hire a bunch of it professionals across the country to work on this uh no you know at the moment we we really don't have have too many open positions we've just got a absolutely absolutely rocking team so um speaking of remote work do people want to put employee monitoring systems on is that becoming a thing it keeps coming up like um and you know i wouldn't do it with the high-end employees we have but call centers record everything on a computer if you want to work from home for jet blue doing customer support you don't expect that like the screen's not recorded the whole time and they're tracking you how many calls you're doing and i looked into it because i wanted to increase productivity at our company and i was like hey is there a way people could get a private report or maybe them and their manager of just how much work they did because we can see it in slack and notion and google docs like we could see your activity so if you think somebody was screwing around you could say how many days did they log into slack and i look at I don't look at it every month, but I've looked at maybe twice in the last year, just who logs into Slack every day, right?
1:13:03And it was pretty interesting to see who was like 30 of 30 days and who was 19 of 30 days. And did they take vacation days? That famous incident when Marissa took over as CEO of Yahoo, and they had like 10 ,000 employees that were all working from home. And I guess they pulled the records for their VPN. And ultimately, what she found is that the vast majority of employees, when they were working from home, were in fact not working because they weren't even logging into the VPN. So they couldn't actually engage any work. I think what a lot of companies realized was that was more a function of working at Yahoo at that time than it was with anything else.
1:13:39Yeah. So do people want remote employee monitoring? And what's the best practice there? Yeah, we don't see that. And that's also something that we always tell our customers. We have an agent that's installed on the machine that cannot see anything that you're actually doing. It's really just looking at the health and the security of the device. We have no idea what you're doing. But yeah, I mean, I think what we see across particularly our startup customers, the departments where that really matters is ultimately either sales or engineering. Pretty easy for engineering teams to see just what the amount of code that folks are committing.
1:14:17and pretty easy looking at Salesforce reports, who's actually getting in there and making calls. So I don't want to say it's a solved problem, but I think for the people where it matters, a lot of the tools they use today can kind of tell them who's busy and who's not. All right, lightning round, Jeff, you're at three. Go. All right, three companies we recently invested in. We have a company called Homebase that is kind of an operating system for small businesses. So 200 ,000 merchants in America, roughly 2 million workers are on the app. This is obviously something I'm very passionate about. We talked about it earlier in the pod.
1:14:50Great company, John Waltman, terrific founder. He and Rishi have built this thing over the last decade. So note to founders, it takes time to build great companies, but this is a company that is valued in the hundreds of millions of dollars, north of 50 million in ARR, growing very quickly, doing well, and just a company that we're really excited about and extremely well run. And I will just tell, note to the world out there, it is very challenging to raise capital right now at this stage for companies. And this is a real testament to the cohort data, the margins, all the things we talked about earlier.
1:15:24These guys have their stuff together, and it's just an impressive team that we think is building in a great space, similar to what HubSpot did, Toast did, Square did, Shopify did, going after this 40 % of the economy that is small businesses. So Homebase, really exciting company. Second, I'll give you Arteria. It's an AI AI that Ryan mentioned earlier, vertical AI. So this is a company that's going after the banking industry, probably also will go after insurance, healthcare, energy, places where a lot of contracts, agreements, documentation, a lot of data surrounding all of that. Very important to the businesses.
1:16:03You think about the banking industry, literally executing contracts and trades every day. There's a lot of data there. They've built a proprietary set of AI that can extract information from that and help companies make better decisions on the fly and also just understand risk exposure and things that are really important to these very large companies that are very important to our economy. And then the third one is a company called Vercel. Hopefully all of you guys have heard of Vercel. It's an incredible infrastructure company, modern developer platform. Every month, over a million developers are building new projects on Vercel and launching them.
1:16:35Huge beneficiary of what's happening with Gen.AI and just an amazing founder in Guillermo, who has also become a great co-investor for us and great angel investor that we've partnered with on a number of new investments. So Vercel is one of those companies that we think is very well positioned to take advantage of everything that's happening in AI. It's on the infrastructure side, so not something you will hear as much about unless you're a developer, in which case you probably love Vercel. So another company we're excited about. Fantastic. Take us out, David. What a great episode. I love having Ryan on because Ryan is an angel investor and a founder.
1:17:08That is It's really dynamic to have you have both of those hats on. And Jeff, great job. Excellent. Well, it's been another great episode of the Liquidity Podcast. I love the discussion. For Jeff Richards, Ryan Dennehy, Jason Calacanis, this is your host, David Weisberg. Thanks for listening.
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David Weisburd hosts Jeff Richards, Ryan Denehy, and Jason Calacanis to discuss down rounds in startups (5:26), changing operations in response to market shifts (23:07), and impact of AI & remote work on job availability (1:02:17).
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(5:26) Down rounds and cram down rounds in VC deals
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(14:22) The terms of investment and the importance of good business fundamentals
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(37:26) AI adoption in startups and businesses
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(1:09:34) Comparing the fundraising process pre and post COVID
(1:14:30) Wrap up: Jeff's latest 3 investments and Ryan's company, https://www.Electric.ai
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