YouSaid · the spoken record

Jake Saper

lines on the record: 123
first: 2025-03-10
most recent: 2025-03-10
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“But we led Rick Series A probably in 2016. So I've been on the board there for almost a decade. And it's a knowledge management product that grew really quickly. And then during COVID, started to stall a bit. And to Rick's credit and his executive team's credit, they realized as AI started to pop up, if I pair a knowledge management tool with generative AI and build generative AI-enabled search and offer both knowledge management and an AI-enabled search product together, that's a very compelling offering. They've done that and now growth has reaccelerated. Through the journey, he did have to restructure the company, right? So he cut the company. I think now we have like 60 employees or something, but he's doing that profitably and growing quickly again. So in some ways, like these moments actually make the business.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Rick is like, is one of the most amazing human beings I've ever met. Yeah, he looks like Jesus. He looks like a Savior, actually. If you look at a picture of him”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, what happens to those? I think all of those companies are in this existential moment to figure out okay, what do I do? How much do I invest in agents? How real is it going to be? Are my customers going to adapt it? How complimentary is that to my core product? Or am I just kind of shouting in the wind? And the honest truth is most of them aren't going to make it, unfortunately.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. Again, some of these companies catch a second wave. And we talked last night, we talked a bit about what about the even smaller ones, the ones that are at 50, 100 million AR.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a really good question. Savior's too strong of a word because most private equity outcomes don't generate incredible returns for the VC. So savior is not the right. Maybe Savior in the sense that like get your money back. The sales loft outcome was an awesome one, but that was an exception where private equity was willing to pay whatever 20 times AR. But most cases, they're paying whatever three to five X. So it's a different thing.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“There will be consolidation, there will be private equity, and there will be a few that reinvent themselves. There will be a few that are nimble enough to figure out how to adapt to the new era. But I think most will get consolidated.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Large players in the incumbency, which supports the fact that there could be multiple large players in this next generation as well.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a good company. And no one knows about it. Yeah, it's crazy. So we led the series A there, my partner, Kevin, led that Series A. Kevin's still on the board there. And that company is just absolutely hitting and it continues to hit in the public markets. Like read up on it's amazing. That's a winner-take-all business because it's LinkedIn for doctors. And so having a number two there doesn't make any sense. So that investment we definitely underwrote to that and it worked. But let's take the lovable, like that dynamic that we were talking about last night. For folks who aren't aware, these are companies that help you build web apps with no coding experience. So you can go to bolt.new and you can write, build me a website for the new 20 VC product and have it blue and put these buttons here and make it do this, this, and this, and then it just happens. It's kind of astounding how easily it happens. And it puts a lot of questions around what are the knock-on effects of that in our economy. But those businesses will clearly disrupt the squarespace and the web flows and et cetera, et cetera, et cetera. And what's fascinating about that space is that there are many, many very”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think you can make money both ways. So let's take the winner take all market. So network effect businesses generally obviously win or take all. In our experience, we invested in a company called Doximity, which is like started as LinkedIn for doctors. Are you familiar with this? Yeah.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Because a sales loft, because of course, and there's a bunch of others, and there's some much of there's still gestating. There's companies like drone deploy and others in that company. We just had a big crypto outcome in that company called Zappo that just distributed large multi-billion dollar distribution.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“By far, the most of it. But what's interesting is that fund also had sales loft. It was the highest multiple ever paid by private equity for a software company. Companies acquired for $2.3 billion. And we were the Series A investors there. So that was a very good outcome. But that returned the firm, the fund a few times. I can't remember how many times it returned it. But Zoom returned it, you know, more than 10.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“We made, I forgot the specific multiple, it was definitely more than 3x in that one. I don't remember the specific number, but I think it was north of 5x. The challenge with that is when you have a fund that's of a certain size, even if it's a 10x, it's still not going to necessarily move the needle, that fund, I believe, was fund three, which is the same fund that has Zoom. It's the same fund that has some other really large outcomes. And so that fund is already at a, I think it's a 16 times DPI, even with a 10x on the chorus investment. It's not necessarily going to move the needle.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Forms a broader thesis beyond the sales specific use case the course was focused on that could help inform how we invest more broadly.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so when we got the real thing, I was like, oh, great, I've already studied for, like, they basically gave me the test before the test. So it is true we have had prepared minds, but sometimes it's not always obvious. In the case of chorus, for example, so chorus.ai is an early competitor to gong that was acquired by Zoom Info for a little less than $500 million. We led the seed round. We were the early investors there. It was sort of the first voice AI company. We had some prepared mind around like we thought voice would matter. My partner Gordon really thought voice would matter in the enterprise, but we didn't have like a full conception of what was going on. We just liked the young founder. We thought there might be something here. So we made the investment. Ultimately, it grew nicely and was acquired a little early, but it was acquired for a nice outcome. And that helped inform a broader thesis that we've since developed around voice AI. We made a bunch of investments in BLAND and Regal and assembled and a bunch of vertical specific ones as well. So I personally, I think we more broadly, develop prepared minds from the portfolio company investments we make. Like what is the thing about what's happening at Chorus that”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so the reality is, I don't think any venture firm makes all their money on prepared mines. I just think that is bullshit. I do think because I've lived it that you can have prepared minds and it can't help you get there sooner or faster than others. I mean, in the Zoom case, it's a great example. They literally gave me my interview case on a competitor.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the reason why a founder chooses a VC is because they believe that you'll help them bend the odds of success on the journey. It could be in helping them with something like go to market. It could be them helping bring them people to hire. It could be helping give with advice. It could be because you're a great therapist to the founder. There's lots of ways where you can help bend those odds. Ultimately, that's why someone chooses you. You need a reason, right? You need a reason to be chosen. I agree that in general, if the founder doesn't need to rely on you a lot, that's great. But the reality is the odds of success of these things are so low that if you can even bend the odds of success incrementally, it matters a lot.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It was competitive. It was competitive both because there was early growth, but also because the company was profitable. And so we didn't have to raise capital, which is part of the reason why the price got as high as it did. Ultimately, I think the reason why he chose us is because we committed to him that we would help him build out a proper enterprise sales motion on top of his product-led growth motion. I think that's a really important point, which is as exciting as bottoms up PLG is, all PLG companies eventually need to layer on enterprise software motions to be sustainable and enduring. And Eric, while he was great technologically, didn't know how to do it. So we committed to helping him do it. We hired a guy named Dave Berman after we made the investment from Ring Central. And we built out a proper enterprise sales motion. The company's off the races.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Fortunately, the way our firm operates is a fairly collaborative approach, so I reached out to my teammate, Joe, Joe, who has a private equity background and was a math Olympian child kid. And I was like, help me. And Joe dove in and figured out that the numbers that Eric had given us around the churn for the business were wrong. Eric himself was miscalculating churn. Specifically, he was counting upgrades from low tier to high tier as churn.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's It was going to be priced at $200 million post money valuation. And this, again, remember the company was at around $2 million revenue. And this was 2014. In 2014, right? This wasn't 2021 peaks. This was pre AI, all the rest of it. But we really believed in the thesis. We believed in Eric. And the product-led growth was really strong. Even though it was early, it was super strong. So I'm tactically diligent, but the numbers are really going to matter here just because of the scale of this decision. I flew out to Boston because I was visiting my then girlfriend, Danny Hertzberg, who was an employee at HubSpot at the time. And I'm sitting in the HubSpot cafeteria frantically trying to build the financial model for this company to justify the investment. Brian Halligan walks over who's then the CEO of HubSpot and gives me a hard time the first time I met him that added to the stress of the whole experience. I don't have a background as a banker. I was an operator and a consultant before, so I didn't really know much about how to build a financial model. So I'm stressed out trying to build this thing, trying to make the numbers tie, and some numbers just won't tie, specifically the churn numbers. So Eric had given us a bunch of churn data on his business, and I was trying to figure out how that ticked and tied with the numbers that I was calculating, and it was just off.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Called the codec, and it worked really, really well. My partner Santi, who ultimately led the deal, is from Argentina, and he used the product to call his parents or to call his family back in Argentina and discovered like, hey, this thing works way better than everything else on the market. This codec is real. We should take this really seriously. And we paired that with the growth. And we're like, let's dive in. However, the deal was not straightforward. The reason the deal was not straightforward is it was going to be the largest check we'd ever written at amongst the highest prices we'd ever paid and the company was incredibly early. So for context, it was going to be a $20 million check out of a $250 million fund, which is a lot of concentration.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“So we aspire to be a thesis driven firm. Before I even joined Emergence in 2014 and 2013, the firm had developed a thesis around the fact that there was an opportunity to replace WebEx, that Webex was a tired product that wasn't very good. In fact, when I was interviewing an emergence, the case they gave me to interviewed emergence was for a company called Fuse. Fuse was video conferencing software, an early competitor to Zoom, and I was supposed to diligence that case and then make the recommendation should or shouldn't invest, and they were going to hire me based upon that. Ultimately concluded we shouldn't invest, made that case. Fortunately, I made the right call. That was also the decision they made. They hired me. Fast forward a few months, I joined the firm, and the very first deal that we're pursuing where I'm tapped to lead diligence is him. So the good news was we had a prepared mind around the space. We also saw incredible early product-led growth. The company was around $2 or $3 million in revenue, was growing very quickly, but obviously very, very early. And we believed in Eric. Eric was the VP image at WebEx before, so knew a lot about the space, and he'd rebuilt the core technology.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I was thinking this is a PSA for anyone who visits London. You give them the most enchanting walking tours at this place. Like some might say romantic, just like incredibly beautiful, such appreciation for the history of this thing. So thank you.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“We have deployed a little less than $2 billion in capital. We've returned in cash a little over $8 billion. That fund, I believe, was fund three, which is the same fund that has Zoom. I think it's a 16 times DPI. We did this analysis on how have our deals fared certain graduation metrics relative to market. Nine out of 10 of our deals have gone on to raise successful fall-in rounds. One out of five have gone on to raise rounds at north of a billion dollars. One out of 10 of our early stage investments have gone public.”
2025-03-10 · The Twenty Minute VC · 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital · IDENTIFIED FROM THE TRANSCRIPT · source