Fundraising from VCs and Hiring VPs in 2025: AMA with Jason Lemkin SaaStr CEO

Jason Lemkin covers hiring, GTM, and fundraising for early-stage SaaS. Interview 30 candidates and ask what they'd do their first weeks. Use a customer-segmentation pie chart to allocate resources. Be honest with investors about revenue mix and margins. Run 45/90/180-day check-ins for enterprise customers to measure onboarding velocity and reduce churn.
Chapters
Hey Jason Frank from salesforge so we are just an 11 month old business and grew to about 2 million ARR. So currently raising what would you be your top advice for companies that actually do well during this so you're 2.
Million in their first year growing quickly right. First great. Congratulations. Just assume you have to Talk to more VCs than you used to. Don't play any games. Don't artificially constrain the process. Don't tell people they have 37 minutes be a little more chill and talk to twice as many people as you planned. I'll take some more questions so when.
You like install the last five seven years have been wildly different is the kind of technique so how you spot those any broken pulling desk I think.
There'S a couple questions there. How do you figure out if they're any good at the role because everyone's happy right? 1 Interview 30 by the time you interview 30 the top three will stand out. 2 if it's for a role you've never hired before you don't know find someone that's great at it truly great and ask them to just interview your your final candidate simple answers but that sounds simple but that always works. Interview 30 and find if you've never hired a VP of English before find the best technical lead CTO VP events you can on planet Earth. Do whatever it takes and ask her him if they'll just interview one candidate for you it'll save you a lifetime of problems. In terms of the Burton broken I wish I had a a perfect test on it. I like to just ask a lot of open ended questions but for I'll tell you the one that's the best one first sales or product or customer success Sales product customer says there's the number one best open ended question on all of mankind since the dawn of enterprise software in the early 1500s. And the question is to sales customer service to product. What would you do your first couple weeks? Not first 30 days 69 because then they're all thinking their plan right? What would you do your first couple weeks? The best heads of product, the best heads of customer success and the best BP sales will give you the same answer. I'm gonna go meet customers. It's always the same. I remember the first great product my end of product my my ultimate full time VP of product was a guy named Aran Aloni who then became CCO@GONG CEO&CCO@ Gong. He's great. He joined very early with Amit but he was and and that's what he did his first week. But another guy, the best. This guy that was head of product, ironically at SMB, at SAP. But because SAB had acquired his startup, the best product guy I knew, I asked him to be my interim head of product. Who found me? Iran. That went to Gong and he started and I wanted him to meet with my engineering team and I wanted to work out some friction I had with my CTO and I wanted him to work on Mari API and our documentation. He said, no, I'll talk to you in two weeks. Jason. I'm like, what do you mean? God is I'm going to go talk to 20 customers. I'd never seen this before. It was new to me. I'd never hired a true pro, a VP lower product. And he came back and he wrote a whole memo of all his notes and learnings and here's what success factors said and here's what LinkedIn said and here's what said I've analyzed and here's all the issues and this is how we're going to work on your product. You don't learn the product sitting in the office for two weeks on your own or just randomly sitting there. Customer success should go visit your top customer. First job, go visit your top customers. Sales wants to get into those top accounts, right? So that's the cheat code for the broken and the bitter. When they say when they want to stay at home, when they don't say they want to meet customers. And not all of us love meeting customers. Not everyone does. Don't hire them. That's my cheat code is what are you going to do your first couple weeks listen for go meet customers. Then I'm like, I'm leaning in. Thanks. My name is Phil. Thank you for a great conference. My question is can early stage startups successfully run product led growth and enterprise go to market strategy simultaneously and can what indicators suggest they'll succeed? Yeah, this is too much is made up of this. I did like a podcast interview with Aaron Levy a little while ago and I asked him this. He's PLG is just freemium with analytics. It's just freemium that you can measure. It's just freemium that you can multivariate test. We have been doing freemium since 1996. I think since the first web apps came out. I think we make this too complicated. And early apps like WebEx was originally. I mean I'm really dating myself. It was really even before my time by the case studies and she know webex was the first billion dollar error SaaS company that blew up even before Salesforce and they started off charging per minute because that's how telephony used to charge. Right? And then they did this really stressful thing. They went to having a self serve motion that was free with upsell and they did this cannibalization. But my point is they've been doing that since 1998, right? Efax, which was a inspiration for when I create. We my team created the web based E signature. Even before Docusign we copied Efax which was freemium plg. I'm really reaching back in time. So these are not new. Freemium is not new motion. And I did write a Saster post on folks that are PLG and SVD more seriously, if you look at folks, whether you it's almost everyone that starts off self server, PLG adds more sales over time. Canva last week did their enterprise event. It's all about their new sales team, right? It happened. Asana started off all self serve. Now I think then they went about 60, 40 PLG SLG. Now they flipped it. Now it's I think it's 40% self serve, low end and 60%. So we all end up with this model. Not everyone, but maybe Squarespace and WIX don't have a sales team, but I think they might. And TikTok has a sales team. They're here. So everyone ends up with a sales LED motion. We talk like PLG is something new. It's not. It's something old that has better analytics and software. Today, people like us in the room, 9 times out of 10 we like to click and buy, don't we? So it's nothing new. It's nothing new. And certainly anyone on the developer side knows it's nothing new. And even open source is the most extreme version of it, right? It's PLG with no humans whatsoever. Okay, so when do you know what to do? Two things. First of all, if you don't start with a self onboarding, self procuring service, it's wildly difficult to start later, which we talked about. So I'm going to assume you're starting with a product that people can try and buy on their own, but you're also trying to sell it at the same time. Basically what tends to happen is by about 100 customers, you have a statistically significant distribution. I have done either on Zoom or my office. This exercise with so many folks in the early days, CEOs of Checker and Algolia and Pipedrive with Owen from Intercom. So many Folks, I brought them in half million, a million three hundred thousand in revenue. Wherever I'm. I asked them how many customers they have. It's 50, 80, 100. So it's enough. And I do this exercise all the time, either on zoom or input. I write a pie chart and I circle a pie chart and I say, how many customers are small, how many customers are medium, and how many customers are large. I don't ask them to define it because different customers, and they're like 40% small, 20% medium. What's left? 40% big. And I'm like, okay, this is you. And actually at 1, if you're at 1 million, this will be you at 10 million and a hundred million. Unless either the market changes or you change it. And then what I do is I. And sometimes if they've gotten bigger, I'll do two circles. I'll do where were you at 100k and where were you at a hundred? Or where were you at a million or 5 million? Not in a meeting, but maybe over a board meeting. And you can see the trends change. Right. It's fun to do it at 1 million, 5 million, 10 million. And see how those three, three pieces of the pie. If you have no medium or large customers, I would stay at the bottom of the market for now. Shopify stayed there for a long time, even though they're all about enterprise today. But they stayed at the bottom of the market past IPO. HubSpot stayed there intentionally. So sometimes the pie chart says stay low. Right. But if you're asking the question, it's probably because you got like a couple bigger deals, but the team's complaining. I don't know if I really want to do security. I don't really know. They want the. I don't want to do the integrations. A lot of times folks that like self serve don't really want to deal with sales or vice versa. Right. Now we got bigger deals. Yeah. Now we're building self. Okay, that's hard, man. Maybe you should be going more mid market, lower, because that's quick. Yeah, that's what VC say. They don't have to do the work. Look, the bottom line is I want to make. I want to keep this simple. It sounds like your pie chart's heavily enterprise. So if you're asking my advice, knowing almost nothing, should you go down market, should you go PLG and mid market and S and P, I'm going to say, don't. You've got no customer. If you have no. Almost no customers there, think about the energy you're going to put into that. And the other thing I do when I do this pie chart exercise, the 40, 40, 20 or whatever it is, what I basically say to founders, and this is that I 100% believe this is true over many years, is this is where your energy should be. And sometimes when I say is okay, they're like, but yeah, like, but we're going more enterprise. I'm okay. If you're 40%, 40%, 20% enterprise today, where do you want to be in a year? And they're like, in a year I want to be 40, 50% enterprise, 25% mid market, 25% SMB. I'm like, okay, great. Then half your product story points, half your product, half your engineering, half your marketing, half your CS. Half of everything should be in enterprise and 25% should be here. Roughly. It's a framework, right? So you have to decide. This is the fool's errand we talked about. And sometimes founders, as founders, we have to do fool's errands. Sometimes we're right. Sometimes HubSpot was right to do CRM. When everyone said it was silly because your customers are in marketing. That's a 700 million business today. They were right. So sometimes you have to do this as a founder, but your organic customer base isn't telling you this is it. Break the rules if you need to. This is your job. But don't listen to your VCs. They don't know what they're talking about. They're not building the software. In theory, mid market is faster than enterprise, but who cares? The thing is about long sales. Yeah, they're faster, but. But bigger deals are bigger. So we think it's better, but it's not. Because once you've been doing enterprise for a couple years, you stop actually stop caring about sales cycles. Because when you have one deal, it's really stressful when you have 50 big deals with six month sales cycles and you have a good sales team. That's why we actually have pipelines and we say, okay, this one's going to close this quarter, this one's going to close next quarter, this one's in security review and this one's in a paid pilot. It's part of the cadence. And it's not that bad if a $2 million deal takes 10 months to close, is it? So don't lead into, oh, mid market, our VCs. It's not. Nothing's easier. Let's summarize it with that. Nothing's easier. Everything's Just harder. Thank you. Thank you.
My question's about valuation multiples. You showed a slide saying that multiples are obviously down the last couple of years. But we've got some situations now where we've seen some revenue that we haven't been classifying as mrr, but the margins are lower. But we've been billing clients consistently for over 12 months and that the NRR is over 100% on it. So we now, okay, we could pull in an extra, let's say, I don't know, almost a million in ARR. In that we've got another enterprise customer who's coming on so we can add an extra couple million to our irr. It's going to drag down like our gross market.
It will.
So I'd like to get a read on you in terms of like how investors are.
Like, what's the investors are. Investors are still a little stupid here. They shouldn't be. In the old days, in the old days, we were super gross margin sensitive. In the old days, people like when Twilio started to scale everyone that was building software, like, they were like, this is the stripe of communications. This is an amazing company. The VCs were crapping on Twilio because it had 40 or 50% margins. Right? Both were right. Twio ended up being an iconic generational company. And it also trades that it traded and ended up after 2021. It ended up trading at a pretty weak multiple because of the margins. Right. And so VCs in the beginning were very wary of these lower margins from blended products. And then I know you know this some in 2021, no one cared. No one can. No one would really look at the gross margins. They just wanted the top line to be growing. And it, I didn't understand it as someone who's been in the space for a long time, but the public markets didn't care either. The public markets, I'm exaggerating slightly, but the public markets said, hey, Toast's hardware business, that is still gross margin negative counts. Toast doesn't even count it in their reporting anymore. And Shopify got too big of a boost from its blended model. Right? Shopify is epic, but its financial services margins are much lower than its software margins. Right. There's a number of examples. And so in 2021, no one cared. Today, the public markets absolutely care to an extent. Right. And a software company really does need to have north of 70% margins. But to be tactical, I would say a lot of VCs today, all they care about is top line. Growth today. So what I would do, if you have communications software and other. I would be honest. And a lot of founders today aren't honest. I would be honest and I would just do three colors on your revenue stack. Say, listen, we're at a million million in revenue today. Personally, I wouldn't even call it ARR even though everyone does. We're at a million of revenue. 300ks from software, 400ks from messaging and 200ks from services. Right? Shopify does it. Build.com breaks out their segment people Toast is very. Look at Toast. I've written up on Sasser. They're very honest about their different segments. Put it in different colors in a pie chart and let VCs come to their own conclusion. Some old timers may say I'm outta here and that's fair, right? Or they may take a marker and only give you credit for the bottom line. Others will don't, really won't care. Right? There's literally a company I invested in, great founders. They're at 25 million in ARR today, more than doubling. Pretty good, right? But 20% of the revenue was passed through. Zero margin revenue. Does that count? No. And I kept saying this to the other fancy investors on the board and the table. I'd be like, it's a good company, but 20% is pass through and another 20% is basically 5% margin for merchant services. So really it's not a 20, it's a great company. I guess I'm old school. I think there's a 14 million company and they didn't care. And this company raised 10 tons and tens and many tens of millions of dollars. And then finally a couple weeks ago, one of the investors was like, wait, how does this work? And we totally restated the revenue my way. We totally restated the revenue and the revenues. 60% of what it was, right? Does it change the ultimate company? Maybe not right? But the point, there's a lot of points of that story. But my learning is that even today, going to the opener, investors are still hunting decacorns, right? And so they're not gonna, they're not gonna give you credit because you're profitable. They're not gonna give you credit for lower growth because of macro issues. But what they will do is they get a little blind to hypergrowth. Like they're so deaf. Because fewer companies are hyper growing. The ones that are hyper growing, people will actually be more forgiving. So be honest. But I wouldn't not share that revenue if it has gross margin, if it's 30% margin grade. If it's zero like this pasta revenue, I think it's sketch. Hi, Jason, thanks for organizing a great event. I'm going to ask the same question.
I asked last year.
Terrific. Which is what are your thoughts of what the main themes you're going to be talking about next year at Saster? No idea. I don't know. I probably said that last year I. The slides I made for the opener. Really it took me a while to synthesize the B2B2B the B2B2C the AI stuff. So I don't know. I'm actually, I'm the. I'm pretty bad at the. I'm pretty overall at seeing how businesses compound. But for example, I did this, I did a couple of these like round tables with Harry Stebbings on 20VC and I did 50,000 with him and then 10,000 with a couple other top, top investors that we would have an IPO a week in the second half of the second half of this year. So July is July 1, the start of the second half. Do you think we're going to have 26 IPOs the second half of the year? I think I'm gonna lose my $80,000. Now, having said that, I'm right. I just think I'm gonna be off five quarter. Not even one quarter off five quarters. I was a little too bullish, so. I was too bullish, so I don't know. The only thing that I'm thinking for next year, I am very tactically bullish on AI. I am not excited about the 200x ARR deals. I'm not trying to see if exciting things like poolside that are worth 2 billion at less than a million. I'm not that smart to know whether those are good bets or bad bets. I do believe that any area of SaaS where AI is even a smidge helpful today, let's not be cynical. That's even a smidge helpful. I am just tactically bullish that in a year it will all be better and we're all going to benefit from these as long as your CTO can take advantage of it. Going to our point, we're all going to benefit from this rising tide. I'm not crazy. I'm not AI crazy, but I am very excited to see the block and tackling benefits that we get in core B2B SaaS. So that's what I'm. And in fact, it's Saster annual this year. We're actually going to have an entire AI day and AI summit morning till evening and it's all going to be about improving workflows with AI. We're going to have great we're going to have CEOs of Klaviyo and folks from all the top leaders but instead of talking about how to turn text into images and cartoons and we're all going to talk about how it's changing B2B stuff we care about. So that'll be the first day September. You can only come to that if that's all you care about. So I'm into that. But you can keep the cartoons and stuff. Thank you.
Hi Jason. Such a great event this year.
Indeed.
I think it was better than last year.
Good to hear content.
So my question is when it comes to marketing agency on which ones underdeliver the Most in the SaaS and the founders really need them is the legion.
Called emailing bdr which agencies?
Which marketing agencies?
Look I agencies are interesting mostly hiring agencies is the fastest way to flush your money down the toilet. As a founder I remember I invested in a third time founder that I've known for years co founded his CTO a company that was acquired for over a billion last company was acquired for a couple hundred million but this is his first time as a business CEO and it's like a couple months in things aren't working. I'm going to get some marketing help. I'm like crazy. I'm going to hire the best agency in Southern California. Everyone says they're great. I'm look at their website. I'm like and it's only a hundred thousand dollars and we're going to do a big launch around this and best one three months later he gets some really nice collateral and a really good two by two on the industry and zero leads. I just begged him not to do this. One of the smartest people I've ever worked with. I gave you a million stories. Look, there are gems and I do believe like anything that is professional services there is a gem. Find the best lawyer, it makes a difference. Find the best tax credit, find the best marketer then sometimes they are at agencies, right? But hiring an agency per se, not a person it's a way to flush your money down the toilet. It's true in marketing because all the all marketing agencies want to do is run formulaic adwords, give you formulaic collateral, give you formulaic this. It doesn't work for startups. You don't have a brand they want to flush your money down the toilet. Agencies for BDRs and SDRs never work with a few exceptions. The reason they never work is because with 20 clients you never learned the product. There were flickers of it working 10 years ago when folks weren't working Cadence and there were flickers of it working in 2021 when we bought so much software. And I'm not saying there's not someone here that but if there, there may be someone at an agency that can is almost full time for you that could run the BDR playbook but the regular agency trying to they're trying to run the exact same emails, the exact same coffees, the exact same breakup emails. No one understands your product. No one can respond to a question. Better to brute force it yourself. Don't hire an agency to do it. Hire if you can hire the person in house, great. If you can find a person. But make sure they can actually do it. Not that they say they can do it. Too many agencies say they can do it. They just want a lot of clients and have them do the exact same thing and that's more power to them. It's their business model. But it's a terrible idea. The one thing I'll say just for the broader team of niche is that is my view. There are gems at agencies and also when you go to hire your first head of marketing if they actually had a lead committed actually can do Gen duke and grow they can't do everything themselves. And a lot of marketers will want to bring in a lot of agencies. Don't let them. You got to back them but always let them pick one. Most marketers have one agency marketing agency they've worked with for 10 years, their right hand person. At least let them bring in their. Let everyone bring in one right hand person for an executive. You have to and marketers often will have one agency and whether you see it or not you got to back them.
Yes, everyone here seems to be found. I'm from a VC but I'm fairly new to the vc. We're fairly industry agnostic but it's so technical that sometimes difficult to to cut through how to find those gems, how.
To find the best startups.
What's your perspective? Obviously a very broad question.
That's a big question for vc. You either got to find the ones that other people don't find or you gotta win. You gotta win, right? You gotta be in all the deals and find a way to win to beat the other people. Right. The later stage venture is all things the more it's about winning, right? Cause you're in every deal. I remember Someone I forget who years ago told me I think they joined Andreessen Horowitz fairly early. Right. And they didn't care at Andreessen whether they ever did a deal. They weren't obviously the top. They were just going to get fired if they didn't see every deal in SaaS at the time that they just needed to make sure that no one got funded on TechCrunch or strictly VC that Andreessen didn't see. And this turns out to be true at many other funds. We got to see everything. The earlier you are, the smaller you are that that becomes impossible. Right. But so you got to either find things that other folks haven't found in places like Sasser are great. I found I've talked to so many folks here that are doing millions that are bootstrapped, there aren't on any other radars. It's one way or build a network of feeders. If you're not, if you're not super early stage unless you're pre. Pre seed there's always someone earlier than you and, and the best a investors like if Kristoff still here. Kristoff and I started co investing years ago when actually I. He used to be super early and I could invest after him. Every great SAS VC or wants to go meet with 09 because they just want to see what the hot stuff is. Everyone comes hello Pavel, what's on? What's new on the portfolio? How many of these do you get? 20 or 30 a year all the time. Right. Because it's a way to hunt the. And you can do it on media. But so my point of the story is another way to do it is just build the relationships one stage earlier. Right. And it's funny, when I started investing I didn't know what I was doing but I had a pretty good brand. Right. And all these associates and principals and others starting when I was working so they would just show up at my office and I didn't get why but they were looking. It was this is their job. And they were like hey maybe Lemkin seems to know a few things when Sasses, what are you looking at? What's in your portfolio? And I, I thought that they like Saster or something and some of them did but they just this is the job. They look to someone, have enough juice, enough whatever and you got to be all over them and, and so you're early in your career like how can I do that? But these, they all did it. They all should. But not everyone did some of these relationships have lasted for many years, right? Like I met Teddy Wardy. He runs sass at Insight. He was a junior VC at the time. Sat on my doorstep, right? I'm like oh come on in. Kid has gone on to be one of the best successful he's in everything from whiz on down sales left with me. I'm pretty good. He started off as the kid coming by to see who the Saster guy is. Not that I was necessarily the perfect one but it's just there's always someone downstream who's always hunting and so the these aren't perfect ideas but it's a hustle and sales game. This is not. It's not everyone thinks for what it's worth to be cathartic to founders. Everyone in venture thinks until they realize how it works. They think it's a game of thinking about it. All the great ones come by our office all the data dogs and lizzes and HubSpot. We see all of them. We get a couple months to hem and ha see a few reports decide is that Brian Halligan really going to go I don't really like NBAs. Something really going to happen. No, it's a frigging. It's a sales business and a hustle business for almost everybody and the only folks that don't have to hustle like that have massive inbound and there's only a handful of folks where the founders pick them. It's all. It's very rare.
Almost ruining a point that most marketing agencies flush down the money. Not all but also context. I've been and drawn like a seven figure B2B sales enablement. That's our biggest challenge, right? We tell people like hey don't give us all your money. We don't know what we're going to do in three months with you. The biggest challenge is trust and other agencies also says we just promising the moon. Are we going to find product market fit for you? We're going to flood your calendar with.
An agency cannot find product market fit for you. That, that that's my story with the cto. That's what I missed in the story really. He hired them to find product market fit for them and that's the great sucker bet of all sorts of what.
Would you advise a person like me that doesn't want to promise the moon AI based shortening sales cycles, two weeks with cold emails, whatever. The promise is that it's not going to work.
I get the competition. Here's the cheat code. If you want to build an agency, if you Want to build a services business or as founders, if you want to hire someone to help you. Here's the simple, the simplest cheat code. And this is why it's hard to run an agency. If it's the principals and take the meeting. If it's the found, if the folks running the agency. Every time I get someone reaches out to me for a need I have, we have a lot of needs assessment. When we have nine people, we have a lot to do. And sometimes I'll get a pretty good email from an agency and at the bottom it's business development associate or they want to screen me. No, you can beat out 99% of the agencies and you can decide if one of these fractional resources or worthy founder is do I get the principals. And agencies don't scale because the principals only have 50 hours a week. And so there's an overlap where you still get the principles. Right. But Taylor and Caitlin run this cred PR agency. There's Taylor right there. If you want to hire folks to help you with speakers and speaker content, hire them. They're the best. I've worked with all of them. But here's why we're lucky that they own the place. This is their fifth sasser, so I don't want to talk to their bdr. If you're lucky enough to trick someone that's a principal, that's good. That's the cheat code. So if you want to deliver, be that person. But the problem is you can only have so many clients. Right. And every agency deteriorates when the principals don't do the work. But also, how do you scale if the principals don't want to do the work? Right.
So basically, pitch that you're small enough to still be able to give the principles to clients.
Pitch that I will be there. You, I listen. We chatted for 60 seconds. I. I know that you're smart and have passion. If you told me you would come to my office and work in my office and you would be my outbound program, I'd give you a shot. But if it's. But if you want to hire me so that two kids you found for down the street are going to do it, I'm out. So that's the summary and that's what I would look for as founders is will the principals do the work? It's just very, it's very rare. So thanks for the question.
Thank you so much. Challenge accept.
All right.
Yeah. Hello. First of all, thank you for all the sales content disaster. It has helped us so much. Good to hear I'm looking for now in the implementation side.
So change the practices.
What should happen after you close the deal?
Look, there's a lot of best practices which I'll allude to but it can be hard if you have too many questions. But I love one eye opener. For us at this second Sasser annual we had Peter Gassner who is the founder of Viva, which is worth 35 billion. It only raised 3 million in primary capital. It's worth 35 billion. It owns CRM and content management for pharma and biotech. It is like the Salesforce and more for biotech. In fact he was the VP of technology at Salesforce and said hey, they're not really doing life sciences. I'll go do it. I'll raise 3 million and build a $33 billion company. Kind of a cool story and but they're very enterprise. They're very, they're all seven figure and eight figure deals. And I asked Peter, you can see it on our video, what do you do with new customers? He's I'm paraphrasing but it's we do a 45 day call. I do a 90 day call. I do 180 call myself at that time, me and my team. And so that's a. Doing these three calls for real is I think a great framework. Then back into what the KPIs are under it. People don't do enough of these calls anymore or the most. The saddest thing is in CS folks still talk about doing qbrs quarterly and I ask a lot of CS folks how many of your customers show up for your QBRs, how many you do 1 in 10 doesn't count. Force to be documented for senior leadership at least with your bigger customers to do three calls when they start so that you can hear what's happening and surface the issues and nobody really does that. And then here's the thing and then and I think we might have talked about this earlier and Sam Blonde alluded to it in the morning, measure it. Measure how what percent are being onboarded in the fastest possible time and make that a core KPI to drive it up. Almost all founders find that fewer of their customers are onboarded as quickly as they think. Fewer. They're often shocked that they sign a customer and they just assume their team's gotten them up and going and they find out what it's been 60 days, it's been 90 days and their instant churn risk right if they don't deploy. So figure out what whether it's 15 days or 30 days or maybe 60 days if you're enterprise figure out what your goal is. Ideally 90% or more of customers are onboarded in the shortest period of time. Measure it constantly, talk about it every week and use that to spot the sub issues in the sub KPIs. So thanks for the question. One more are we done? All right, one last question. Thank you.
Hey Jason Frank from Salesforge. So we are just an 11 month old business and grew to about 2 million bucks in ARR. So currently resume. What would you be your top advice for companies that actually do well during this? Looking to raise an A? Doing really well.
Okay, I'll give you two. I'll give you two pieces of advice. So you're 2 million in their first year growing quickly, right? Two things. First, great, congratulations. Just assume you have to Talk to more VCs than you used to. Don't play any games, don't artificially constrain the process. Don't tell people they have 37 minutes. Be a little more chill and talk to twice as many people as you planned. There's a lot of reasons people Those type for it, AI those types of metrics it assuming everything else, you probably have an 80% chance of getting funded in 2021 today. Maybe people are gun shy, maybe they're scared to invest. Maybe they only want to do infrastructure, maybe they don't. Maybe they're everyone's tired of sales investing, right? Even me. Like my third or fourth investment was Sales Loft which sold for two and a half billion. I'm tired of sales after that. Like I'm not I'm bored of the I'm just fatigued from the category. So there's just so many variables in this we talked about at the opener. There's just so many segments of the world and not everyone is in market. Not everyone is receptible. And you say you're AI right? But you may not be the type of AI people want. They may want OpenAI or cohere or perplexity or DeepL or so you think you're AI but you're not necessarily the flavor of talk to two to three times as many folks is my one advice. The second advice, I wrote this up on Twitter the other day and then I got just hazed on Hacker News but I was right and I wrote about there are two things I got his but I got a lot of positive engagement but I wrote one of them was. One of them was about how a founder sent me a deck in May that was dated March and I was hazed for being too critical. But my point is, there's so many wrong things. First of all, they've been fundraising for two months. Okay, but at least pretend like you're not struggling to fundraise. Three, at least pretend I'm one of your first choices. Obviously, I'm not even your top 20 if it took you two months to get to me, right? Three, you didn't even read it. You didn't even read it in two months. You didn't even update it. Right? So I got hazed on that one. The other one I just got lightly hazed on that was all over hacking. The other one I got lightly hazed on is I. And I point these all out to be helpful. You can see why. Like, you can say, hey, that doesn't matter. But it's also a reason I passed. And if I passed because you had March 2020 to 2024 at the bottom of your deck. So is someone else that has attention, someone else that has limited time, someone else that has a decent portfolio so you can make fun of it, Give a guy more another chance. It's not a meritocracy. It's a brutal business investing. It's almost impossible to make money. So when things look off. So anyhow, the related point, the second one I got hazed on was this person came in that was at 2 million and was growing like 80% and not accelerating. Okay, so just a below the line, but the email was really good. This was Clearly a great founder. Two who was in a vertical SaaS category with not a lot of competition, unlike you. And you could say, look, I know it's not quite there, but this is a really cool category. I have personal passion around it I'm interested in. The email is really good. They clearly understand this niche category that probably nobody does. Once in a while, those accelerate. They never really do. But you sometimes you get excited about one that's on the margin venture. Sometimes you get one that's on the margin. Right? You get excited almost because you have passion around it or you love the founders and so you give them a little slack. And they said at the end, they said, we're raising at least 10 million. And the problem was it was too much money for me. The one problem was they didn't go to my website, which says I only write up to $4 million checks. That's a fail to not do the right. But they all knew about Sasser. It was the greatest email and all this stuff. So they should have read the website but my real point of the story is it was a. It was too much money for me. But if she'd asked for four to five, then I would have probably leaned in when or if they asked for 10, but everything was great, I'd be like, I'll find that. I'll call Christoph. I got my buddy. I got another five. No problem. Like, I'll get all my friends. I'll get all my friends together. If you're the next whiz, right, you can ask for too much money. But here, when you're. So my point is, be. Be a little conservative in your asks. Don't be so aggro in your timeline. Don't be so aggressive in the amount you're raising. There's some minor negatives for asking for too little, which it implicitly might ask for a lower valuation. There's some minor negatives for not telling people they have an hour to decide, which is they might not ask or get off the can. But be more chill today. Be more respectful. Be conservative on how much you ask. You can always raise more. You can always raise more than you ask. And those things will just increase the odds in stressful times that you raise the money. That's my best advice. Yeah. All right, thanks, everybody, for the time.










