Pod Insights Equity Podcast Inside startup shutdowns with the creator of Layoffs.FYI (re-run) About this episode Today on Equity, we're throwing it back to when Mary Ann interviewed Roger Lee, an entrepreneur who’s spent the better part of a decade building tools for employees and employers alike. Lee is an angel investor as well the creator of Layoffs. FYI and co-founder of Comprehensive and Human Interest.
Roger joined us on the show last year in the wake of 2022’s tech layoffs, but this week we’re focusing on the business of shutting down and why investors are lining up to back startups in the space, including Roger.
We also talked about:
Just how many more companies shut down in 2023 compared to 2022 (spoiler alert, it was a lot!)
How many more layoffs we saw last year compared to years prior
The types of companies winding down and laying off
How his work is tied to all of it and the role of AI
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Transcript 0:11 Speaker 00 Hello and welcome back to Equity, a podcast about the business of startups where we unpack the numbers and nuance behind the headlines. I'm Mary Ann Acevedo and this is our interview show where we sit down with a guest, think about their work and unpack the rest. Today, we're talking to angel investor, creator of layoffs.fii and co-founder of comprehensive.io and Human Interest, Roger Lee. Roger, welcome back to the show. So happy to have you here.
0:37 Speaker 01 Thanks for having me again.
0:38 Speaker 00 Yeah, we're super excited. Roger joined us on the show last year in the wake of 2022's tech layoffs, but today, we're focusing on the business of shutting down and why investors are lining up to back startups in this space. Listeners may recall our coverage of Sunset and Simple Closure, two companies that recently raised capital to help other startups wind down. So we'll not only be talking about that, we'll also touch on recent layoff numbers and the outlook for the rest of the year when it comes to both shutdowns and layoffs. So to start, Roger, you invested in Sunset. They just raised capital, I believe it was about 1.4 million in funding, mostly from angel investors. Simple Closure also raised money. And Karta recently announced that it's entering the space with its own offering.
1:22 Speaker 00 I was curious, how did you hear about this company? What drew you to invest in it? And why do you think this space is one that is worth investing in overall?
1:31 Speaker 01 Well, I've always been excited about businesses that help automate very manual and tedious processes, dating back from my time at Human Interest, doing that for 401ks, to what I'm not doing now at Comprehensive in terms of helping companies automate compensation management. So when I heard about Sunset and how they can help tech startups wind down and automate all of the tedious legal compliance, tax and HR work associated with winding down a business, I was very excited about that. It's very timely because unfortunately, the reality of the current environment is that there are more companies shutdowns happening,
2:13 Speaker 01 coinciding with more layoffs in general, which I'm very in tuned to based on my work at layoffs.fii. And so I thought that that Sunset was a great service that could help.
2:25 Speaker 01 Automate these really tedious wind down processes at a time when it's very stressful for founders in general. You know, think about how tough it is just to have to wind down a startup you've been pouring your blood, sweat and tears into. And even after you've decided to shut down the business, now you realize you have to do months of work to actually formally wind down the entity. So
2:49 Speaker 00 Right.
2:49 Speaker 01 Sunset's ability to automate that is, uh, you know, really, really interesting.
2:53 Speaker 00 Yeah, I know. It seems like a lot of people think, oh, there's so much work in founding a startup, getting one off the ground. They don't really think about all the work and time, money that could go into it when it doesn't work out. And historically, actually, I saw a statistic that about 91% of startups actually fail, which means only about one out of 10 succeed. Now, we don't necessarily hear about all the startups that don't make it. So I know that what's reported in the media is far less than what actually happens. Now, in tracking closures and layoffs on layoffs.fyi, have you seen numbers go up in the past couple of years? You know, we've had a definitely a challenging fundraising environment. It's been harder for companies to raise. So my guess is you did see numbers
3:38 Speaker 00 go up in 2023 compared to 2022 and 2021, but I'd be curious to hear what your data shows.
3:45 Speaker 01 Yeah, based on what layoffs and FYI has tracked, company closures, just the ones that have been reported on, have gone up by 70% from 2022 to 2023.
3:56 Speaker 00 Wow.
3:56 Speaker 01 And
3:57 Speaker 00 That's a lot.
3:58 Speaker 01 Are on pace to do something similar, if not exceed that, in 2024. And then I know there is a stat that PitchBook put out recently that they were, they estimate 3,200 venture-backed startups were shut down in 2023. And they think that even that is likely underestimated. So we're talking, you know, thousands of companies just in the venture-backed space that are shutting down on an annual basis. If you look at just sort of businesses in general, not just the VC-backed startups, it's something close to a million businesses that get shut down every year.
4:32 Speaker 00 Right, right. I saw that statistic out there as well. I think it was like 700,000 to a million per year of businesses. But in the startup world, I mean, I have to wonder though, I mean, 70% is a huge jump. Like, that's a lot. But also 2020, 2021, we had, you know, the frenzy of capital flying everywhere and there were a lot of startups born. So I also have to wonder, is that number just proportionally higher because we saw more startups born during that period? Does that make sense? Would you agree with that?
5:02 Speaker 01 Likely the shutdowns, of course, are gonna fluctuate based on the environment in general. So it's not surprising that as layoffs have gone up over the past two or three years, so have company shutdowns. But what was eye opening to me when I was learning about space is that these company dissolutions, these kind of painful wind down processes, don't only happen when a company gets shut down. Most acquisitions actually also results in the entity being dissolved anyway.
5:32 Speaker 00 That's true.
5:32 Speaker 01 Because it's structured as asset purchase sales where the acquirer isn't actually buying the entire corporate entity and all the liabilities that come with it, but just selectively buying, you know, the IP, the team, things like that.
5:45 Speaker 00 Right, just parts of the business.
5:47 Speaker 01 Exactly. Which means the original company still has to be wound down even in, even in an acquisition. So this goes to speak that even though there's, you know, going to be some fluctuations on how many companies get shut down, this activity is always happening either due to shutdowns or even due to acquisitions. And just something that's been talked about very often, you know, I think, kind of like with layoffs, company shutdowns have sort of been this keep quiet, hush, hush thing, you know, most folks don't like to talk about it. It's not reported on the news. It kind of just goes away quietly, which is why it's sort of this interesting opportunity because now I think there is a little more transparency about it now. You're kind of seeing some founders actually become more vocal and transparent about their companies shutting down, talk through sort of the learnings from it, use
6:32 Speaker 01 it as a way to kind of give advice to other founders who Had a lot of exposure now about what it's like to start a business, but not what it's like to actually wind one down. So it comes at an interesting time when it's becoming more transparent. Folks are talking about it more and the pain of winding company down is becoming more obvious to folks who might not have realized just what goes involved in it before.
6:56 Speaker 00 Yeah, you raise a couple of good points. I think one is that there's this sort of misconception that when we talk about having to wind down, that it strictly means a company has maybe failed and that's it. They have to just shut down. But in reality, it could mean a couple of other different things. It may mean, for example, and Brendan, who I talked to, the co-founder of Sunset, pointed this out, that a lot of the companies that they work with are actually doing pretty well revenue wise, but they're just not necessarily what you would describe as venture scale businesses. So they realized, okay, rather than just keep trying like on this wheel of raising capital and trying to maybe one day exit or go public, let's just kind of cut our losses,
7:37 Speaker 00 maybe sell off parts of the business, sell off IP, do an aqua hire with another company, that sort of thing. So it's not necessarily, oh, wow, this company just failed. It ran out of money. They had a terrible business model. That's not necessarily the case. In some cases, they are actually pretty viable businesses, but where founders just decided not to keep going for one reason or another.
7:57 Speaker 01 Yeah, that's exactly right. You know, I think one thing that most folks don't realize, even founders, is just exactly what goes on having to wind down the entity. And why is it even that if they go through an aqua hire or go through an asset purchase sale, they still get stuck with all this work to wind down? You know, it's sort of all the things that you do when you start up the company, you now have to obviously do the reverse of it. So instead of incorporation process, now you have to generate a plan of dissolution to actually wind down the entity. Of course, there's the kind of all the IP. What do you do with that? If that's not part of the sale? You know, what do you do? Do you assign it? Do you try to sell to someone else? Do you auction it? Do you throw it away? Do you open source it and so on?
8:38 Speaker 00 Hmm.
8:38 Speaker 01 There's kind of all the tax stuff. So filing the final tax return. There's oftentimes kind of state level withdrawals that you have to do to formally kind of close your entity in any two different states. Then of course, there's kind of all the vendor contracts you've signed. What do you do about that?
8:54 Speaker 00 Right.
8:55 Speaker 01 If you have investors or creditors, you know, with the money that you have left in the entity, how do you distribute that? So just, you know, all this stuff and it's kind of the last thing that founders want to deal with if they've shut down or sold their company is to now be stuck with all this, you know, laborious work that often takes kind of weeks or months to kind of fully wind down. And so if they've sold their business or gotten aqua hair, they want to move on to the next thing, right? And same if they shut it down, they want to figure out what's next for them. That's what founders want to spend their time on, not on all this sort of legal and tax and compliance stuff. But it's important to get right because it's, you know, oftentimes a legal requirement. And so services like the ones that are popping up now are going to help make that a lot smoother for founders and help them kind of get back on their feet or move on to the next thing.
9:37 Speaker 00 Yeah. Infinity Ventures co-founder and managing partner Jeremy Jankar also pointed out a very similar thing. His firm invested in Simple Closure, which is also in the space. And he said, hey, look, these startups raised at pretty robust valuations. They maybe haven't grown at the metrics necessary to raise an up round. So some of them are saying rather than raising down round or, you know, totally selling, they might just sell off parts of the business. But anyway, he did also make that point of, okay, whatever we can do to help these founders move on faster, the better for everybody involved. So it sounds like that's a similar narrative that I'm hearing. Also, one thing I found interesting about Sunset is that they opted to mostly raise angel money as opposed to venture capital
10:19 Speaker 00 because of the reason that it saw many of these other startups choosing to wind down because they didn't want to be in that same position of, okay, we have a good business model, we're making money, but not at the rate that these VCs might want us to. So they decided to go the angel route. And another kind of unique thing I think about what they did was that they have this referral structure, I think with investors that each time you refer a company to Sunset, you get a greater share in the company. Can you talk a little bit about that?
10:48 Speaker 01 Yeah, exactly. I do think it was smart from them to. Raise capital from angels primarily and not VCs because it does give them that optionality where they're not going to have to sell their business just because it doesn't generate, you know, sort of the venture level expectations of growth. They can, if they want, go down that path, but if they have a viable business, they can still keep going without having to have set up for kind of these great expectations.
11:11 Speaker 00 Hmm.
11:12 Speaker 01 And speaking of that equity incentive program, I thought that was really unique too as an angel investor in Sunset is that the way I understand it works is that as investors refer companies and customers to Sunset, then they can earn more equity in Sunset as essentially a referral bonus. And it really kind of helps align the incentives for investors to actually help and provide value to Sunset even after they invest. You know, as a founder myself, I know that most investors pitch themselves as being value-added investors where they say, hey, we're going to give you money, but we're always going to help in all these ways after we invest. And the reality ends up being that that's true to some extent and maybe less true than others.
11:55 Speaker 01 And you never know quite know in advance, you know, which investors will actually follow through on that promise and which ones won't. And so what Sunset's done is they've kind of given this extra incentive where, hey, you know, if an investor just invests their money and doesn't refer customers, that's okay. But if they do want to add value to Sunset and refer customers to them, then they can get extra equity in the company and that rewards investors who really do help out and refer customers to them. So I thought also been an interesting way to reward the investors who wound up helping a lot post-investment and kind of help align incentives.
12:31 Speaker 00 Hmm. So since you have created layoffs.fyi, you're also, I think, in kind of this unique position of maybe seeing firsthand which companies are shutting down. So, but I guess, I guess one thing that popped into my mind with this though, is it? Is it in a way creating, I don't want to say a negative incentive, but would an investor be less likely to work with a company to help it succeed if they think to themselves, oh, well, I don't think this is going to work out. I'll just refer them to Sunset and let them move on. I mean, or is that just like, I know, I guess, worst case scenario, or hopefully, most investors going to act honorably and not do so unless they really think that there's just no better alternative?
13:10 Speaker 01 That's right. That's right. And, you know, in the end, investors are going to financially benefit the most if their portfolio companies succeed in spite of any referral incentive that Sunset provides. But of course, you know, especially, you know, with the angel investors and seed investors that Sunset raised from, the sad reality is, kind of like the stat that you shared, most of those startups will end up going out of business or going through some sort of back hire or asset purchase sale. And so the reality is that these investors are just naturally going to end up seeing a lot of the portfolio companies having to go through their wind down process, you know, with, of course, the consent of the founder. Oftentimes, the founder's reaching out to the investor saying, hey, we're going to have to shut this down. And so when the founder's kind of made that decision already,
13:53 Speaker 01 but now they're left with this mountain of months of work to have the wind down that the entity, you know, if the investor can recommend that company to Sunset, that could be a win-win-win. Where now that the founders are able to automate the wind down process and the investor can potentially get some incentive out of it.
14:11 Speaker 00 How long have you been angel investing, Roger?
14:13 Speaker 01 I've done off and on angel investing dating back to, you know, even before I started Human Interest, so 2013, 2014. I wouldn't say I'm an active angel investor by any means. I kind of do it particularly kind of in tech companies that I know well, where I know the founders well, or in spaces that I know well. And most of the time, I'm busy running my startups, but I do like to kind of help support other founders and ecosystem and try to be helpful where I can, especially if it's founders or spaces that I know well.
14:47 Speaker 00 One other question that I have. So obviously, you're tracking closures, you're tracking layoffs. What industries are you seeing more shutdowns in than others? I mean, obviously, I cover fintech quite a lot, so that's the one I'm most familiar with. And I know that we've seen a lot, for example, and you alluded to this earlier, about how this has been sort of a taboo topic that people always, I don't know, like, there was some kind of shame around. And now it's like, a little more acceptable to be open about it when your startup shuts down and talk about why it happened. For example, Braid, a fintech that shut down last year, the co-founder, she put out a really lengthy blog post that I thought was awesome, because she detailed very specifically what happened. She owned up to some mistakes she felt like she made that may have led to the company not
15:32 Speaker 00 succeeding. And I thought, how helpful for other founders, right? So to your point, I do feel like it is getting to be a little bit less taboo. But anyway, my original question is, are you seeing more shutdowns in certain industries than others?
15:45 Speaker 01 Yeah, it's interesting. I started layoffs at FYI in 2020, when the first wave of COVID shutdown-related layoffs started happening. And back in 2020, you did see very clear industry trends, where the most common industries within tech were transportation, travel, and retail. And that makes sense, because those are the ones who'd be most affected by COVID shutdown orders. But now, fast forward to kind of this most recent wave, what I call kind of like, the layoff wave related to interest rate hikes that started in 2022, and it's still beginning today. It's really affected all industries in tech. There's kind of no one industry that's been disproportionately affected. The top
16:26 Speaker 01 ones are consumer, retail, hardware, finance, healthcare, and so on. But that's essentially all the major sub-industries of tech in the first place. So you're kind of just seeing it all over the place in all sub-industries of tech. Of course, there are certain ones, like finance and real estate might be disproportionately affected, just because those are the most interest rate sensitive. But to be honest, it's kind of hammered all areas of tech. So there's not really that kind of industry concentration, the way that there was in 2020 with the COVID shutdown layoffs.
17:00 Speaker 00 That's really interesting. How does that correlate with the actual layoffs you've been tracking? Is it similar? Also, I'm just curious, did we see a lot more layoffs in 2023 versus the previous years? And if so, how much more?
17:13 Speaker 01 Yeah, definitely. So there were, like I mentioned, two main waves. The first was in 2020 as a result of COVID. And so we saw about eighty one thousand employees laid off in 2020.
17:25 Speaker 00 Wow.
17:25 Speaker 01 Then 2021 went down a lot, only sixteen thousand.
17:29 Speaker 00 Oh, my goodness.
17:30 Speaker 01 Twenty twenty one.
17:31 Speaker 00 I didn't realize it was that much less.
17:33 Speaker 01 Yeah, a lot less, you know, tech was booming, interest rates were low, everything was great, sixteen thousand only in 2021. Then, fast forward 2022, more than ten X jump now at one sixty five thousand.
17:48 Speaker 00 Goodness, so that's double twenty twenty.
17:51 Speaker 01 Yeah, even higher than the COVID-related shutdowns.
17:54 Speaker 00 Wow.
17:55 Speaker 01 And the 2022 layoffs, of course, spawned by the Fed's beginning of interest rate hikes. Twenty twenty three actually was even worse.
18:04 Speaker 00 Ooh.
18:05 Speaker 01 Two hundred sixty three thousand employees in twenty three, which compared to twenty two was, you know, about sixty percent more than the previous year. So that year even worse than the previous year, worse one on record of the recent years, way higher than the COVID wave, which we all thought was really bad.
18:23 Speaker 00 Hmm.
18:24 Speaker 01 Uh, when it happened.
18:25 Speaker 00 I I didn't I didn't realize it was that bad. Like, I knew there were a lot more layoffs last year, but I didn't realize it was there was that many more layoffs. That's pretty traumatic.
18:36 Speaker 01 Yeah, yeah, three X what we saw in twenty twenty and even sixty percent more than twenty twenty two. And no, it's because a lot of hiring happens in the meantime.
18:46 Speaker 00 Right.
18:47 Speaker 01 So, you know, it it is large numbers for sure, but if you kind of put it in the context of just like how much especially big tech hired during the pandemic era surge. They hired a lot, you know, between twenty twenty and twenty twenty two. So, you know, when they were cutting, there were just a lot more employees to cut from. And that partially explains why the 2022 and 2023 layoff numbers are so high. And then, of course, now we're in 2024 and only two months in, but you know, already about 50,000 employees in the first two months of 2024. So.
19:20 Speaker 00 Wow, 50,000 in the first two months alone?
19:23 Speaker 01 Mm hmm. Compared to 81,000 in all of 2020. So it was been a bad start to the year. Things are calming down, though. We have seen this pattern last year and this year where layoffs spike in January and to a lesser extent, February. Because it turns out that at least among the big tech companies or the public tech companies, have they been doing layoffs kind of on this every January, every February cycle uh likely related to annual budgeting and planning. So companies like Google and Microsoft, Amazon have announced layoffs exactly one year apart, you know, January 2023.
20:03 Speaker 01 And then again in January 2024. So so we do have this kind of seasonality effect related to annual planning. Where last year the layoffs did start dying down in Q2 and Q3. And I'm hopeful that that will happen this time around as well, especially with uh interest rate decreases potentially on the horizon end of this year.
20:22 Speaker 00 So what do you project? Will we be lower or higher than 2023?
20:27 Speaker 01 It's always tough to play.
20:28 Speaker 00 Both shutdowns and layoffs with both of them.
20:30 Speaker 01 It's tough to play the forecasting game, but so far it does seem like this year, as bad as it's been so far, has been on a pace that's lower than that of last year. So I am hoping that 2024 will finally see a lower year after two years of increases. And that I think will be true for both layoffs and shutdowns.
20:50 Speaker 00 So since last year, we saw a 70% bump in shutdowns compared to the year before. Like this year, do you expect then it'll be less than last year overall? Fewer shutdowns?
21:00 Speaker 01 I think so.
21:01 Speaker 00 Okay.
21:01 Speaker 01 I think so.
21:02 Speaker 00 That's good.
21:03 Speaker 01 Bigger crops, you know, hopefully. I think it just depends on, again, what happens with the Fed. That's kind of been the game over the past couple of years. So if the Fed is done raising rates for real, inflation keeps coming down and if the rates start going down, it's expected later this year. I do think that we'll finally kind of see layoffs and shutdowns decrease in leveling compared to previous two years. But if there's surprises and hey, the interest rate declines don't happen, or inflation becomes, you know, more persistent than expected, then unfortunately, I think we're going to see more pain if that ends up being the case.
21:38 Speaker 00 Ironically, AI, I believe, could play a role in both helping to grow jobs and startup formation and also contribute to layoffs and startup shutdowns. What are your thoughts on the role of AI here?
21:53 Speaker 01 Yeah, it's been interesting to track from a layoffs perspective because I have been seeing companies increasingly cite AI as a reason for layoffs. And it comes in kind of two forms. One is, you know, there are certain companies that are being disrupted by AI and so they have to, you know, lay off employees because their business model is threatened. Example for this is Chegg, the education technology company. And then maybe the more common reason is just companies speculating that they might not need as many employees because AI can make their teams more efficient. And also trimming down their non-AI staff can help them double down and shift resources to focus more on AI talent,
22:38 Speaker 01 even as companies eliminate jobs elsewhere in their organization. And companies like Dropbox and Meta have alluded to this reason in their layoffs. And of course, you know, final example, you know, I think we saw the headlines recently of Karna, that the fintech company mentioned that AI was potentially able to take the place of 700 customer support agents. And now they don't need as many customers for people because AI can automate all of that. And that 700 number was notable because they actually several months earlier hadn't laid off 700 employees. They may have clarified that that number was not related, but it did raise eyebrows at the time.
23:16 Speaker 00 Right.
23:16 Speaker 01 You're kind of seeing this chatter of, hey, you know, companies laying off employees because AI can do their jobs or because AI can just make their teams more efficient or just to help them clear a budget to hire an AI. And that does, you know, come with more AI hiring demands. So on the other side of things, there is of course increasing demand. And from a hiring perspective, we at Comprehensive are tracking salary trends very closely since we deal with all things compensation and are seeing that even though salaries in tech have largely stayed stagnant over the past two years, you know, AI is one area where it's not staying stagnant. And you're kind of seeing quarterly increases of a horse of 10% in AI salaries
24:01 Speaker 01 just because the demand for talent there, especially on the technical side, is so strong.
24:07 Speaker 00 Yeah, as I had mentioned in the beginning of the show, for those who are not familiar, Roger did co-found a couple of companies. One is Human Interest. It's a 401k provider mainly aimed at smaller to medium sized businesses. And it was in January of last year that that company ended up getting a minority, BlackRock ended up getting a minority stake in that company after it had reached unicorn status. Comprehensive, I covered that company as well that you started. And as you mentioned, it's trying to help other companies figure out employee compensation, which can be a difficult task. So where are you now? I think last year when we talked to you, you had just launched beta. Where are things now with Comprehensive?
24:47 Speaker 01 Yeah, we've made a ton of progress on that business. And, you know, we've now fully launched the compensation management product. Which helps companies get out of spreadsheets for things like their compensation review cycles and managing their pay ranges, as well as communicate compensation to employees, and also benchmark data on seeing where employees fit relative to the market. All of which is that, you know, helping companies up-level how they do compensation management to make sure that their pay is fair, consistent, and equitable, which is just a huge trend these days. Of course, compensation is the biggest expense by far for most companies, and also the number one driver of employee recruiting and retention
25:31 Speaker 01 outcomes. So a hugely strategic part of a business, yet most companies are still managing compensation in spreadsheets and via ad hoc processes. So we've been building a comprehensive software platform to kind of help companies get out of spreadsheets and, you know, be able to move to the cloud, which they've now done for almost every other major workflow, like performance management and recruiting, payroll, benefits are at this point all done in software. And so compensation is the next one to follow. And so we've been seeing more and more interest now from companies wanting to ditch their spreadsheets and move into our software to finally make that process really streamlined and efficient and making
26:15 Speaker 01 sure that their valuable compensation dollars are being deployed effectively.
26:20 Speaker 00 Yeah, so I realized we were just about out of time. Roger, it's been so much fun having you on the show. I, as always, really enjoy catching up with you, talking to you. You have so much fascinating data to share, so I really appreciate your sharing that with me and our listeners. How can our listeners find you on social media?
26:38 Speaker 01 Yep. So I am on Twitter. My handle is Roger underscore Lee. You can check out websites layoffs.fyi for a tracker of all the tech layoffs and comprehensive.io for the latest pay data.
26:54 Speaker 00 Great. Thanks, Roger.
26:55 Speaker 01 Thanks, Maryam.
26:56 Speaker 00 And if you want more from Equity, you can check us out on X and threads at EquityPod. I can be found on X at Bay Area Writer. We'll be back on Friday. Until then, have a great week.
27:09 Speaker 00 Equity is produced by Teresa Loconsolo with editing by Kel. Bryce Durbin is our illustrator and we'd like to give a big thanks to our audience development team and Henry Pickavet, who manages TechCrunch Audio Products. Thanks so much for listening and we'll talk to you next time.
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