This Week in Startups - Ask Jason LIVE! Returns to TWiST! | E1905

Episode Date: February 27, 2024

This Week in Startups is brought to you by… Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at http://www.vanta.com/twist LinkedIn Ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to http://www.linkedin.com/thisweekinstartups * Todays show: Jason kicks off Ask Jason live! Six live guests ask questions on key topics like career paths in fintech (1:14), startup challenges (8:48), pivoting strategies (34:23), fundraising (46:54), and customer engagement strategies (52:30). * Timestamps: (0:00) Jason kicks off another Ask Jason! (1:14) Tommy asks about getting a degree in fintech in order to join startups (7:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (8:48) Sam asks about common mistakes for first time founders (16:40) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist (17:32) Clint asks about startups surviving the period before VC investments (33:12) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups (34:23) Daniel asks about startups pivoting in the wrong direction (46:54) Greg asks about raising funds before product-market fit (52:30) Oliver wants to know if it is better to go deep with a few customers or gain entry to multiple customers with a more lightweight solution * Apply to the LAUNCH Accelerator here: https://launchaccelerator.co/ Just getting started? Apply to Founder.University Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Follow Jason: X: ⁠https://twitter.com/jason⁠ Instagram: ⁠https://www.instagram.com/jason⁠ LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (7:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (16:40) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist (33:12) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

All right, everybody, welcome to this week in startups. We wanted to try something new, a live, L-I-V-E, a live call-in show where you get to Ask Jason. People love to do Ask Jason, but previously, you know, we get a sound file like people would leave a voicemail. Sometimes they would send a short video or they would just email us to question. That lacked the dynamic nature, the dangerousness of having a live caller. So we wanted to try doing live Q&A. And so let's get started. This week in startups is brought to you by Lemon.io. Need to speed up your product development without draining your budget? Hire vetted engineers from Europe at Lemon.io.

Go to lemon.io slash twist to get 15% off for the first four weeks. Vanta. Compliance and security shouldn't be a deal breaker for startups to win new business. Vanta makes it easy for companies to get a SOC2 report fast. Twist listeners can get $1,000 off for a limited time at vanta.com slash twist. And LinkedIn ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com slash this week in startups. Let's get our first caller on the line.

Tommy, are you there? Yeah, I'm here. Oh, great. Awesome. You have a question for me? Yes. I was wondering, in 2024, would you, think pursuing a master's in fintech is a worthwhile thing?

Okay, I've never heard there was a master's in FinTech, because FinTech usually refers to startups and applications, but who's giving a master's degree in this, and what do you learn in that? It's through the University of Missouri-Sing-Lewis. And like the main, it's like normal finance stuff, and that you learn about like applications of blockchain and AI

and like how they work in the finance world. So, and how much is this going to cost you? And how much in time and money? Like what does it cost to do this? Time it would be like an extra year of school for me because I can do the accelerated version. And then in terms of money, I think it would cost. Yeah, it would be normal tuition.

which would be ballpark 10,000, 50,000, 25,000? 20,000 a semester, I think. 20,000 a semester? And you'd have to do two semesters or four? Just two of the masters. Okay, so $40,000 for you to get a master's in fintech. Okay.

So the degree is going to mean nothing to anybody in our industry. So is your goal eventually to work in 10,000? and what type of job do you think you want to have in tech? Yeah, I mean, working for a startup, like finance side of any startup would be a dream job, I guess. Okay, so you want to work at a startup, and you want to work on the finance side? You're an accountant, you're a CPA? You're... Not yet, yes.

Okay. So, you know, adding 40,000, I mean, if you're independently wealthy and you want to take a year to, you know, talk about fintech stuff that seems expensive and it seems like it takes a lot of time. How old are you? Tommy. Oh, 23. 23. Okay. So, man, my guess is what you're going to learn there is not going to match what's happening in the marketplace. I think being a CPA is great because you're always going to have work. And if you love accounting and you love finance, that's great. Finance is a really good skilled to have, I think a better thing for you to do would be to get inside of a startup that's working in the fintech space and be able to be a jack of all trades operations person

where you could help the startup and try to be a co-founder and you could help with accounting, you could help with raising money, building decks, building models, you know, doing HR, all that kind of stuff. So there's typically somebody in a startup who does all of the tasks operationally that the developer or the salespeople don't want to do. So that's kind of the jack of all trades. I don't know you're going to learn a ton in this. I don't mean that as a dig to anybody, but a year of your life and $40,000 plus living expenses, you're going to still go on, right?

So you're talking about 60, 70 grand with your living expenses. I assume you spend three grand a month living. I'd rather see you just take a, get a job at a startup, you know, just find a co-founder, start hanging out. Where do you live, Tommy? St. Louis. St. Louis. Okay.

So I'm going to give you a piece of advice right now. Take the 40, get the hell out of St. Louis, move to Silicon Valley, and just start going to demo days, get a cheap apartment, and just plunker yourself down right in the middle of all the action. literally get a apartment somewhere on the peninsula, San Mateo, San Carlos, whatever. And just start meeting with people there and trying to get yourself into a startup and then have some discernible skill that they need. Now, right now, finance, you're going to have your, you have your undergrad now or no? No, I'll get it after the semester. Any work experience to date? Not in that sector, no.

Any specific skill that you have that startups need, a specific skill set that they can't live without that you know of? Other than accounting, no, not really. Accounting is a skill, people know. So then the other possibility is try to find a startup that works in the accounting space, and there are tons of them. But have you spent much time outside of St. Louis in your line? No, like traveling, you know, for weeks out of time, but nothing like living there, no. Yeah. So I'm going to give you like the best piece of advice you ever had, I think, which is get the hell out of St. Louis.

Put yourself in San Jose. Okay. Get out of St. Louis, go to San Jose, San Mateo. Just get yourself into California. You find yourself a small apartment and then just be part of it. If you want to be part of it, then you got to be there. So just be there. And then you'll figure it out.

Get yourself an apartment, get a roommate, start going to all the events, start going to the demo days. There's like, you know, all kinds of events going on where you can network and then start a blog about startup accounting and finance, right? And then just try to find an internship or a job anywhere and just tell any founder you'll work for free. You'll work for $3,000 a month, $4,000 a month. You'll be an operations person. Just try to break even, right? if you're willing to do that, right? And just be part of it.

Sounds like you have a little bit of resources to do that, right? Yeah, yeah. It sounds like $40,000 living in, for your living expenses in San Mateo will get you further than getting that master's degree. Nobody in our business cares about the degrees anymore. Less and less every day. In 40, 40, 50, 60 grand.

It's way too much money. Just get your ass to Silicon Valley. One way ticket. That's it. All right. Talk to you soon, but let me know how it works out. Yeah. We'll check you with you in a year. See if you have the hootspa to just get that one-way ticket. Right now, startups have to do more with less. We all know that. It's rough out there, folks.

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Next up is Sam. Sam, question number two here. Hey, Jason. My question for you is, what are some common mistakes you see first time founders make? Wow. Where do I begin? You know, the number one mistake is probably building a product without talking to customers. you know, essentially using your incredible brain power, having two founders sit around,

and they just brainstorm ideas. And then you figure out some really killer idea in your mind because you imagine if the world had this, it would be better. But you don't actually have that coming from a specific customer need. And so, you know, people will be like, oh, you know, dentists should, you know, be able to manage their businesses over their phone or they should be a marketplace to get dental cleanings because isn't it hard to get your teeth cleaned? And it's like, is it hard to get your teeth cleaned? I don't know. Is there a better solution to that? I'm not so sure.

You know, what you want to do is go talk to a dentist and say how much of your business is teeth cleaning and tell me about that and just listen. You say, okay, you're a single solo practitioner. You've got one dentist in this practice. Tell me about your day. You know, what do you do all day? And you just kind of of keep double-clicking, right? So you try to see if there's something that's missing from dentists. And then maybe they say, you know, yeah, we have a lot of last-minute cancellations. Okay, last-minute cancellations, okay.

Or we, you know, insurance is the problem or, you know, we don't have reoccurring customers or whatever. And so, oh, okay, maybe there's a membership club where you can get unlimited, you know, teeth-kating, whatever it is. And you kind of come up with an idea based upon an actual customer need. I think that's not talking to customers would be number one. Number two is I think people sometimes don't have skills. And so they build a team of idea people. What you really need in this kind of a business is to have a team of builders. And so the companies that go far tend to have three co-founders, sometimes two, sometimes four.

And so I would say, Sam, you want to have two or three co-founders in the team and have at least two of the three be actually building the product. So you have a startup, I take it. If AI is your startup? Yep, we do. How many co-founders? Just one other. He's a technical co-founder.

He's a recent CS script in Berkeley. Great. So there's two of you. And what do you do at the startup? You're the idea guy. You're the business guy. You're the sales guy. U.X.

Yeah, just what everything he said, UX, biz dev, sales, talking to customers. and part of the reason we asked that question is the first time we took a spin in our idea. We weren't talking to customers. We just kind of thought of the solution first and kind of in search for a problem. How did that go? It didn't go well. We had to pivot our product quite a bit.

We actually talked to Sonny Madra, your friend, and he kind of guided us in the right direction and to first speak to customers and come back to me and we'll talk about the idea. And so we gathered a lot of feedback. And now we think we're building a product that, customers actually want, and now it's just about execution and kind of beating the competition. Yeah. Who are the customers

you're going after? We're starting, you know, primarily startups and fast-growing companies, small businesses. I don't think we have quite the, our platform, not the technical capability to reach kind of the enterprise. They have a kind of a different set of requirements.

So you want to go with emerging high-growth companies. So, you know, three-person companies, 10-person companies, something like that? Yeah, we're doing AI-powered sourcing and interviewing for recruiters. And so the enterprises typically have a little bit different requirements, which like several integrations and kind of compliance needs that we're not quite there yet. But initially we have onboarded, you know, quite a few beta customers and we're kind of iterating the product still. But yeah, we're really excited. I send a link to a potential candidate and they talk to a chatbot, which asks them a series of questions.

How would it work? Sort of. So we're kind of trying to do the entire pipeline of recruiting. So first of all, it's a sourcing tool for recruiters, right? So instead of using LinkedIn, which is what most recruiters do today, where they kind of just scroll through LinkedIn, doing all these Boolean filters to manually click and click. Now we can just use natural language, just like you do with chat GPT, but it's pretty much like chatDBT for people search. So recruiter can just give a long thing. Like, I'm looking for a software engineer in the Bay Area that has fintech experience at a series of A or series B start. Something super specific that LinkedIn and other platforms kind of struggle with. And then we'll return a list of results, our best ones that we kind of vetted using our kind of AI and other filters we have. And we kind of give like certain analytics and a certain one-something summary of the candidate. And then we also link to their GitHub account so you can kind of show like what they've actually

built and not just what's on list on their LinkedIn. And so I guess then the question is, is the H-CHAs. are people you're talking to or the founder who's looking for a person, everybody would love to just have the list of ideal candidates. So the question is, can the software do that, give you the list of ideal candidates? And is that actually the problem, the list of the ideal candidates? Or is it getting a meeting with them or is it qualifying them? So what's the good part now is you could actually give the product to somebody, the people

you talk to and say, hey, remember we talked, here's the product we built. and I remember you're looking for developers and you're looking for developers who are on this time zone and who have experience working at a fintech company. Here's the results we got. We did a combination of crunch base and LinkedIn and we found these folks

and then we got their GitHubs automatically and put them in a table. What do you think? Then you can at least have the next conversation where the person says, okay, well next I want to get them on to, I want to get a meeting with them. How would I do that? Oh, well, you have to send him an email, send him an email, whatever it is. So I think you've learned one of the first lessons of startups, which is you can't talk

to customers too much. Now, they might tell you things they want that they don't actually want. So there's a whole other series in this science where sometimes people will be nice to a founder because they know you're a struggling founder or you're trying to do something entrepreneurial. So you have to be careful that sometimes, you know, you'll ask them, hey, do you need something? and maybe they are just being kind to you. So you'll find out, or how do you think you would find out

if this is mission critical for that founder to have the process you just described? How would you find out if it actually was important to them or how important it was to them? Well, first of all, whether they're paying or not

instead of just being like, yeah, it's whether they're putting their credit card in. It's really the thing. And one of the things we actually did is for early customers, we are requiring like a payment. I mean, we're not pricing it fully what we would price, but they are still paying customers,

kind of testing it out. So we tried to vet it that way a bit. And yeah, I think just whether they actually put their credit card in and not just saying. That's it. You got it. And that was how Raul, you know, with Superhuman figured it out as well.

You can only sign up if you put your credit card in and you're willing to do a half hour onboarding call. So he sort of challenged people, put up those roadblocks, and then you actually know if people really need a high-end email client that saves them an hour a day or, you know, 10 hours a month, whatever it does for a person. So congratulations, well done, and keep grinding. We'll talk you soon. Yeah, of course.

My pleasure. Listen, a strong sales team can make all the difference for a B2 startup, but if you're going to hire sharks, you need to let them hunt and you can't slow them down with compliance hurdles like SOC2. What is SOC2? Well, any company that stores customer data in the cloud needs to be SOC2 compliant. If you don't have your sock too tight, your sales team can't close major deals. It's that simple.

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Get $1,000 off at vanta.com slash twist. That's Vanta.com slash twist for $1,000 off your sock, too. Next up on Ask Jason Live is Clint. All right, Clint, you are here on Ask Jason Live. This is live. You're looking good. You got a great podcast studio. Yeah.

You got a great beard. We have to do things right. You got the lava lamp and a great shirt. I get in the sense I'm going to get an arm. awesome question. Give me a nice thing. You absolutely are. I'm just waiting for you to grow the beard out so we can fit in.

You know, come on. It comes in pretty rough. It comes in pretty rough. It's not a great beard. Yeah. Yeah. Firstly, thanks for your time. Also, just want to thank you.

Beginning of last year, beginning of 2020, you said, just a minute of audio that you said on the podcast about the need for startups to survive 2023 and that those have a great proposition for investment and to become the next unicorns. And that clip we actually took and that fed us through 2023 just that minute. So it fed us, it fed me, it fed our team. And I think there's a lot through that in cultivating hope as we made it through that. Brutal, yeah.

So thanks for that. If you survive, you can thrive. So survival is super important. And a lot of times you survive and then things can break your way. You know, timing is everything. So, you know, we have this amazing startup CafeX, the robotic coffee machines you may have seen me talk about or I talked about in my book and made that investment, you know, I don't know, seven years ago or inkie made it eight years ago. And man, it's been hard to launch a robotic coffee machine in San Francisco where they fought against it. They wanted us to use powdered milk. Homeless people were

breaking the machine. People were stealing the iPad ordering system. Just really gnarly. Couldn't get into airports. And then also trying to make the software work, the hardware work, the retail experience work, and a great actual drink. So you start thinking about how complex that was. And here we are now. I just was going through the airport. with my daughters who were born right around the time Cafe X was born and they were thrilled to order their drinks from this machine, order cookies and they went crazy and there were 10 people around the machine ordering and, you know,

just warm my heart that that company survived. And there were many times where, you know, COVID, etc., it should not have survived and it did. So the founders who survive have, you know, a special place in my heart. But you have a question for me. Let's hear it. Yeah, thanks for that. So my question really does go around that period of time. I'd just like to hear your thoughts on companies like ours, startups like ours that have been going about three years.

We launched on the downturn. We made it through the 2023. We're now extremely tight on funding. We stuck between not having the metrics to raise some of the investment we need and not having the money to build those metrics. My personal belief is really around that if we can't find a way to help these startups in this position, that it's really quite a detriment to innovation for us as a country in particular, because I am in the States. And so, you know, that's kind of a problem that's developed over the last three years. How do those start-up survive this period?

And they're kind of feeling like they've been left out in the cold a bit as well. And then if you have time, if you could just tap on something about valuations, because obviously when we had our previous and now is different. Yeah, so this is a really, really tough situation to be in. You start during the ZERP environment. You're able to close the seed round. You get to work. You get some level of product market fit. And then the market bottoms out.

Funding dries up. Company's not dead. You've learned a bunch. But now it's a three-year-old company. And you don't get the benefit of selling hope, right, in a dream. Yeah, yeah. And you've got investors now who just want to see metrics, as you're saying, right? And they're saying, prove it to me.

And so, yeah, you're caught between a rock and a hard place here. There's no easy answer other than solving a problem, an acute problem for a small number of customers and then using that customer love and data to try to win over angel investors and seed investors. And having a low burn rate is very attractive today. So if you're only burning 10, 25K a month, 50K a month, I'm sure you're probably in that range of had to guess. Yeah.

So how many employees do you have full? time on the project? Three. Perfect. Well, we had more before. One of the things that you did as well is prompted us really early with your foresight to cut our spending. So we were one of the earlier ones.

So, yeah. You took the medicine. Yes, sir. Absolutely. Yeah. Well, and what's happening is you are part of the ZERP era of startups who has made the transition to the AI lean startup methodology. So there was lean startup methodology.

People threw it out the window. There was like, you know, Steve Blank, Eric. They did a great job of explaining to people how to do stuff really affordably. I'm sure you read the books. I'm sure you understand the concepts. Then there was Zerp where people were like, well, we can always raise. We're optimizing for raising the next round. So we raised the million dollars in this round.

We got 10 people. Yeah, they're just being, we'll raise two million in the next round. If we did a million in the last round, we'll just raise two million in the next run. And then the bottom drops out and the game on the field changes. Because now you're up against startups and we're seeing this over and over again. They have three founders. and they're each taking a draw. Two of the three are builders.

So this team is super lean and their shipping product constantly. And the Zerp era startups might have, you know, six or seven people in the company who don't build the product and three or four people who do build the product. And they probably need to get rid of a couple of those people and get back down to basics and just be grinding on product until you have market pull. Right?

And so it's very depressing when these companies get big and you get to 10 people, you probably experience this because you don't have product market fit. And then there's five or six people who are in sales, marketing, growth, whatever, operations. And they're like, hey, when are we going to have a business here? When are we going to have a kick-ass product that people want? You're better off just not having those people hang around and be annoying, pesky, depressing, and then a weight on the founder. Better off just having three, a lean product team, boom. And I'm assuming that's what you have now, a lean product team? Yeah, lean product team.

You know, honestly, the last year has been just one of the best moments in the company when we look back on it. It was not fun to go through. It was terrible. But I do know that had we raised their money earlier, we would be spending it on the wrong thing. So hindsight's 2020. And as, you know, to your point, the buy-in from the team through difficulty, through struggle, has just been amazing. So, yeah, a lot to learn from it. But, yeah, I do think that-

Tell me about the three people. What's every, you're the founder? What do you do at the startup? What do you contribute? And then who are the other two? What does they contribute? I'm just curious, the composure here of the team. Yeah, absolutely.

It has changed over time. We had three founders initially. We had a release one. Usual story, right? I'm the CEO, and so I obviously, or what don't I oversee, right, everything. And then I've got my other co-founder as chief product officer, so he's a builder, which we like to have, obviously. UX design or a developer. Yeah, yeah, UX design, but overseas development.

Can't code himself, but very close to it. Got it. And then, you know, in replacing the third co-founder, kind of got creative, brought on COO for equity. And yeah, it's been really good. Who's doing the development of the product? You have an outsource dev team or something? Outsource dev team that we have used for two years, actually initially out of the Ukraine, now it's scattered, but haven't missed a beat. So really good.

Obviously, the goal is now to build our own. Yeah. So that's the question is, like, this team out of Ukraine and maybe scattered, are there one or two of those that want to come? on full time and make this the mission, you know, which may or may not be possible. That'll make the optics look even better for you. And then any customers, people paying, what does the company do? And do you have ideal customers using the product and do you have the credit currency? Yeah, we did a weird thing.

We built in the live space within 11 months of the company, we went live on the app stores and got approved in seven countries. Google then ran an article saying we wanted the apps that they love. So we picked up all these users before we were ready for them. That was good and bad, you know. But ultimately, ended up around 1,300 users, 380 those active, converted only 40 to subscription. The subscription model. We actually took a leaf from your book.

What is the app do? Point to socials. Yeah. So the app gives you a space to capture all your meaningful moments in life. So we know how superficial, you know, social media has made us. But this is really a first person, my insights, my thoughts, my experiences, completely private, shared privately. and shared forever generationally. So you can be known in first person forever.

Got it. So you got a little ancestry in there. You got a little journaling in there. And what's really nice about those kind of apps is, yeah, people will want to pay to maintain that stuff. So if you can come up with a format, then you just have to figure out who is the documentarian, who is the archivist of that family. And then those are the people who are motivated to use these kind of apps. How do you find them?

You got 40 of them. How do you find 40 more? Yeah, our initial testing was actually with a nonprofit. We launched the MVP through a nonprofit of 5,500 families that all have life-threatening illnesses in their kids. That was tough, you know, communication through nonprofits, difficult. That was our initial push. But, yeah, I mean, we've got quite a few strategies.

One of the things is we're building a podcast. My background is radio. So that'll build the wait list. And we go after interviewing people on the podcast that have good audiences. So it's not to build a podcast, it's to reach, reach scale. I've been pitched on these kind of memory apps all the time. I think they're very interesting. You know, people a lot of times do it after the person dies and then they start doing this.

I've given a lot of advice over the years of, you know, giving people prompts to ask family members and then collecting those videos for future generations. So I would love if my two brothers as but one example and I, ask my parents questions, you know, every time we saw them and then videotape them and then somehow put them together and then it became some kind of output like a documentary about my parents' lives. But that kind of app or scripting, I've been pitched on people. There are people doing this service where they charge you $10,000 or $5,000 to make a documentary about your life, your family's life, et cetera. And they kind of do this. I think they give you a script. You make the videos and then they stitch it together. Are you aware of these like documentaries?

Do it work for hire? Yeah, but it's not frictionless, you know. No, I agree, but it is indicative of there's something there on the high end. It's a developing landscape, no question about it. And we think our timing's really good. So, yeah, it can do something with the wheel or something. And the price points there. I mean, $7.99 a month, $79 annually works pretty well.

We're looking at bringing that down to $5.99 because it's a kind of a throwaway number. It almost feels too cheap, yeah. I like the idea. Yeah, I wonder if there's. a higher-end version of this. Yeah. But where, I'm just going to think out loud here

for a second with you. Yeah. There are archivists in the world or documentarians. They need work. I wonder if you could match me with a documentarian who I paid

to ask my parents in an app on a Zoom call, whatever it is, you know, 20 questions, and then put those answers into the app for me. In other words, I'm thinking of like a marketplace here of documentarians to jumpstart this.

Now, there are people with more money than time, and those people tend to be, you know, really great customers. And then over time, you automate that, right? So what are the 20 questions every child should ask their parent and document for future generations? You know, tell me about grandma. Tell me about your childhood. Tell me about how you met mom. Tell me about the day I was born. Tell me what you remember about my childhood, whatever it is.

You know, what was I like as a child? And, you know, those kind of things are people would be willing to pay for it. I know I would pay as a high-end consumer. If you said this was available for $1,000 or $500 to hire a documentarian and have them fill out these videos into my, you know, app. What is your app called? CIPA. Yeah, capsule.

If there was like capsule pro, you know, and I could spend $500, bucks, you know, having somebody interview my parents, I would do it. I'd do it in a heartbeat. Yeah, no, totally. I hear that. Can I just change the perspective a little bit in that sense? Sure, please. Yeah, so, you know, when we speak about this sort of thing, one of the things we've got to deal with as a company is that it's not a for one day.

It's not only memories that we're dealing with. Actually, the way we engage in these moments now actually has a lot of meaning right now. It builds authentic connection, the opposite of social media. That reveals yourself worth, the worth of those, and obviously passing it on is cross-generational, which we've done in humanity from the beginning of time. So it is a one-day thing, but actually that's not an application.

Our application is to save your moments now. That one-day add-on is a great feature set for that. But we think we can reverse the division that we've seen in social media through this kind of activation. Interesting. What are we doing now. Yeah. And there's a lot of study around that too, which is great.

And did the 40 people who pay you have something in common? Generally, moms, families, particularly age. We aim at Gen X's. in particular. Perfect. Gen X is. We're all got kids and we're all trying to. Very nostalgic.

It's grandma's photo albums that are no longer relevant, right? That's what it is. It's amazing. I wish you great success with it. I think, you know, keep grinding it out, understand the customers, and then in terms of raising money, you know, I think raising prices and showing growth and then going to raise money with, you know,

a vision of how this could go from 40 to 400 to 40,000 is what you need to show, right? Yeah. what you are maybe going to prove inadvertently is it's a niche product, right? And so that's one of the other things you'll contend with is sometimes startups run experiments. You get to year three, four, five. And what you've proven is, oh, there's a niche market for this, right? Yeah. And so how do you break it out, right?

And I've been in this position myself many times where we're working on a startup and it proves, okay, yeah, there's a $10 million business here or a $5 million business, which then takes you out of the VC race. So you've got to be figuring out how does this get. millions of people every day to use it or tens of thousands of people to pay hundreds of dollars a year, something in that range where you can get to millions of people who are part of this editorial hook. You know, there's usually some behavioral loop in these apps that make people come back every day

and pull them in. Have you figured that out the behavioral loop or no? Yeah, yeah. So while we had the MVP live for two years, we were doing picture, audio, and video in digital time capsules to be passed on. We learned that video is the place to be. You know, we already do this with our phone. We already do selfie videos at like concerts, moments like that.

Or when you're capsuling a moment, that's what you want. Kids first steps or your thoughts after something happened, after you fell in love, remembering those memories. So video only, and I won't say too much more than that. Well, I think going for the vertical video is a smart move. You may eliminate some people who don't want to be on camera, but then you gain the lunatics who live on camera all day long. All right, great job and keep us up to date on your progress.

Well done, Clint. Thank you very much. B2B marketing is not an easy job. It's much different than B2C. Why? Well, enterprise buying cycles are much longer. It's not like you see some cool mug and you buy it as a consumer. No, enterprise buying cycles are long,

and it's hard to find and reach decision makers through most marketing channels. We all know that. So that's why you need to check out LinkedIn ads. LinkedIn recently passed a billion users, which includes 100, 80 million senior executives. That's right. About 18% are senior executives. But there's also 10 million C-suite executives on LinkedIn, CEOs, CFO, CTO's, chief strategy officers, you know what I'm talking about. This means you can find and target these decision makers in a respectful environment, LinkedIn. And according to

LinkedIn, their ads platform generated two to five X higher return on ad spend when compared to other social media platforms. And it's easy to understand why. LinkedIn equals business. Business equals LinkedIn, you understand this. When people are on LinkedIn, they're there to do business. They're not there to talk about politics or pop culture. They're there to do business, right? So your business message is going to be in the right place. Make B2B marketing everything it can be

and get a $100 credit on your next campaign. Go to LinkedIn.com slash this week in startups. To claim your credit, that's linkton.com slash this week in startups. Terms and conditions do apply. Daniel's up next. Good to have one of our portfolio companies come on. Yeah, great to be here. Thanks for having me. So I'm Daniel, founder of Hay Hire. We help the

service industry, hire locals in two days or less, LA 26. And my question to you, Jason, especially because it's relevant to us right now. So in a world full of pivots where pivot has become a buzzword, can you share a story of a pivot gone wrong and the lessons learned from it that people don't really talk about? Yeah, I mean, I could tell you one from myself. When I was doing Mahalo, we were trying to do this like search engine, which actually perplexed. is now doing, which was instead of just 10 blue links, pulling in some editorial.

So my idea was like Wikipedia plus Google search results or Yahoo search results. And it started to get some traction. We had SEO. And the SEO was printing $10 million a year in advertising. It was really starting to crank. And then Google got, you know, kind of kicked our ass with the Panda update. And we lost her all over SEO. know, as did E-How, how to this, how to that.

Everybody who had Demand Media was a company that had a lot of SEO juice, and they just basically cut off everybody. And so then I had this other business, which was YouTube, and we had done a bunch of shows, well-cast, Being Fat Sox, a recipe show, or Mahalo video games, etc. And those channels had really started to get traction. But it wasn't interesting to me, the YouTube kind of ecosystem, but we were having success.

And then I just started doing inside because I was more interested in the journalist in, you know, content side. And I probably should have just stuck with the YouTube side because YouTube was very tiny back then, 10 plus years ago. We were part of their like programming group where they had given like little bits of money to it. And I should have not pivoted to news and inside. I should have just stuck with the YouTube thing and I probably would have had a great

exit. So that was a mistake on my part. I just thought YouTube couldn't work because they were taking 45% of the revenue. When I built my model, I was like, this can never work because you're giving away 45% of the revenue. What I didn't realize was it was going to get to as big as it got in billions of people. So that was, you know, just a strategic mistake on my part. So if I could have changed it, I probably would have just done video games. I probably would have made Mahalo, Mahalo video games that just done one thing. So almost always, you know, something's getting traction and you don't

stick with it enough. And yeah, it's just, you know, people make that mistake all the time. The best way to understand what to do is to obviously listen to customers and see what's going on there. And we knew that they were having breakout video after breakout video after breakout video after breakout video on YouTube. But it wasn't interesting to the founder, right? And so there's, I probably should have just handed the company off to somebody who

did care about video at that point and just let them run with it. So that's kind of the dilemma that we're having right now. We're listening to our customers. We mostly help restaurants, but we have a few restaurants that also do catering, and they want something that's just going to help them with last-minute staffing, and there's a huge need for it, and the dollar amount on these deals is going to be 10 to 50x, potentially. So right now we're at that crossroads. Do we focus on this and just building a pilot for that?

Because even like a minimal pilot will take some work, and we're kind of limited. Or do we stick to our bread and butter, which has been proven to work, but lower ticket. Yeah. So, yeah, and I know what your startup does just briefly. You help restaurants who need workers where there's a big shortage here in America, you know, use your software and platform to get waiters, dishwashers, runners, I guess all of those different people, yeah?

And what you learned was that there's another group of people, catering companies who need 50 waiters tomorrow. And so this happened to a company called Point. And the guy Andrew running it had an issue where people started using Point. Instead of to do surveys and it was kind of like a survey tool, they started using it to you know, like for petitions and stuff like that, they started to petition businesses to give them better deals. So people started using his platform,

instead of to petition people to, you know, save the whales, they started doing petitions to, can I get a free yoga class, an introductory class for $5? Or can I get half off if I buy, you know, a hundred hoagies or who it is? And then everybody, what Andrew told me on this very podcast was everybody started working on that idea. Everybody in the company wanted to work on that. Because it was succeeding.

And the other thing wasn't succeeding. It was having modest success. And so he was like, well, I can't stop everybody in the company because they want to work on this. So we'll just work on that. And he let the employees and the customers determine where they went. And that became Groupon, which became a huge success for a significant amount of time. So my question to you, Daniel, is what does the team want to work on? And, you know, are these customers more interesting, catering companies that need 50

people, 25 people, are they a more interesting customer base? Because, man, you can get 50 people work, 100 people work, 25 people work just by working with one of those companies, right? And handling it. It's a bigger ticket size. And, you know, the people who are on the other side of the marketplace who want work, yeah, maybe they like those jobs better because they pay twice as much, right? Or three times as much. And they're looking for more freelance than going to the same place every day. So, I guess that's my question. What is your team find more exciting? The existing business or this new business?

This adjacent business, I'll call it. I would say exciting. We're all looking at the catering part sounding more exciting. But again, I mean, it's kind of a 50-50 right now between me and my co-founder and our advisors are like, yes, focus everything on catering or no, stick to the bread and butter. And it also depends because most of our restaurant customers, well, not most of them, but I would say about half of them, they also do. catering. So it's going to be the same customer, but just another feature that they really want to use. And if they're not able to do that with us, they're just going to pay someone else for that software. Also, our job seekers, we currently have 20,000 job seekers on the platform. They're also

going to be able to opt in for last minute job request. So it's going to just make it a more wholesome experience for both sides, business and job seeker. Sounds like it's part of the same flywheel then. this is like an adjacent thing. So in some ways, this is your Uber eats to your Uber business, right? Or this is your Uber. This is like DoorDash going into convenience stores after doing restaurants, right? It's kind of an adjacency rather than a hard pivot. And that's why I really like it, because it does seem like if you have those 20,000 folks

and there's no jobs for them or they are looking for extra work, man, you can just email them. Hey, there's a thousand of these people in Texas. that we have their contact info and we can say, hey, we've got a catering job, it pays this much. Would you like to qualify for it? You have to answer these five questions, you know, and then you get more data from them. It's like another reason to leverage the supply side,

which is what Uber found, you know, is another way for them to get the drivers more work. And actually Uber now has an Uber task rabbit type service, I heard. So if you're an Uber driver, you can also deliver goods, and then you can also work in somebody's house as an assistant or, you know, and I think what Dara was saying on one of the earnings calls is it's like they're getting more work for the same base of people, which then is super efficient. So I like it a lot, actually. And this doesn't feel like an or, it feels like an end. Right? And then you just have to think MVP-wise, what's the lightest version of this you can create that solves the problem?

and then price it right. So don't be afraid to price out the bottom half or the bottom two-thirds of people for this product. Make it expensive and just capture the top 20% of people for catering to start. So it's profitable out of the gate. Does that make sense? I like it. No, it makes total sense.

What are you planning on charging for it? So that's the thing. We had our customer that suggested he asked us for it. He's like, can you please build something like this? And he said that he works with certain venues that are paying a 100k a year licensing fee just for access to a certain list and people who are opted in for last minute jobs. So we don't really know. It will really depend on the size of the venue. Sounds like $500 a month is a good starting point.

You know, if they're a caterer, how much money do they make per year, you think, this customer, you think they make millions per year, one million, five million? It really varies. It can be in the mid-hundreds. It can go to the eight figures too. Right. So if this is a mid six figure business, often low seven figure, let's say. So your ideal customer profile is somebody doing a million dollars in catering business a year, 80,000 a month, let's say. Yeah.

So if they're doing a million a year and this is their most painful thing, 500 a month is 6,000 a year. That's not even 1% of what if you go for just people who make a million. this is 1% would be 10K. So this is 50 basis points a year, $6,000 a year, whatever it is, to solve their most acute problem. And this sounds like it's their most acute problem. They're constrained, right? Yeah. And our money for value is definitely our value for money because most of them are currently using gig platforms that charge them double to triple the hourly rate of what they're currently paying.

They're, you know, I'm not catering company owners telling me, like, I pay my in-house cooks 20 bucks an hour and my last-minute waiters, 50, bucks an hour and I feel terrible about it. It just doesn't make sense. And we're not going to do any of that. We're just going to connect them with the people. You pay them how you want. You onboard them how you want. We just get you the people. Yeah. So in a way, you're like this database. You're like LoopNet or something or just Craig's List in a way. So if you just said, listen, it's $5,000 a year and you can post up to $10, 20 jobs a year, or whatever it is, right? So you could just give them $500 a month. You can post five times a month, different jobs. And you know, some, you know, rate per usage or something.

But yeah, start with 500 bucks a month and ask the person for their credit card and just send them to a type form and see if they pay it. You know, and then you can, as Paul Graham has always said, like do things that don't scale, you can just be all bespoke to start. You just email your database manually. You just do slices of your database. So if it was 500 bucks a month or even a thousand, you say, it's $1,000 bucks a month and you have to buy a six-month subscription.

And we're going to go to, we're going to really work hard. You'll be our first customer. and we'll solve this problem for you. Man, they're going to, I mean, they might just have, you know, half million dollars in profits sitting in their bank account and $6,000 is a lot cheaper than hiring somebody who's a manager for $50, $70,000 a year to solve the problem.

So maybe $1,000 a month you do. See how that goes. But whatever you do, overpriced it. So you get only the serious folks. And just tell people, this is for people who make a million dollars or more in catering. That's why it starts at $6,000. a year. This isn't for people with a quarter million dollar a year. I like that. Catering business, just, just neg them, you know. This probably, this isn't for you. If you're making, if you're only

doing like one or two catering jobs a year, you need three or four waiters, not for you. You know, this is a more bespoke, high-powered, you know, industrial strength solution for million dollars in catering up. We don't do like small catering jobs. If you need three or four people, go use Craigslist, you know, or text people. This is for, you know, you need 20 waiters. You need to do 10 jobs a year. 30 jobs a year. And, you know, it's a serious problem for you. I love it. Great job. That's great. I appreciate that. And I'm going to definitely bring it up on our next call with everyone. All right. Great job. Next on the program is Greg. Greg, you have a question for me. Yeah. Hey, Jake. I was curious to get your take on, you know,

is it worth trying to raise before product market fit? You know, for example, you know, we're currently in a pre-seed stage with a rolling safe and trying to determine what metrics and are most critical for pre-seed and seed investors. And when several of those are metrics related to product market fit or revenue generation, you know, capitals often needed to get there also to thoroughly test acquisition models, you know, to generate, you know, the desired data that they're looking for. I'm just curious what investors prioritize from a startup, you know, before product market fit and, you know, free revenue versus after.

So before there's product market fit, they're going to be looking at the team. So how, and this is what our firm launch would do. How many people, how many co-founders do you have? We got three. Three. Perfect. Okay. So you got multiple co-founders.

That's a checkbox of our 13 things we look at in the pre-seeds. You got one of the 13. Have you raised venture capital before? Yes. Great. Check box. So now you've. got multiple co-founders and you've raised venture capital. Have you had a successful exit before? Have you

sold the business to another company or money or stock in that company? No, I've not. Okay, great. So, you don't have that one. Do you have world-class design of the current product, even if it's not launch? World-class design being Apple would feature it and it's got like an incredible, you'd win a design award for it, or are you not there yet? Yes, no, our design is probably one of our strong suits. Okay. So for us, if we see world-class design, like Robin Hood level, you know, calm level, we like that too. And then product velocity. So how often is the product, would you say, how often do you ship new features in your product right now? We're probably shipping new features. I mean, two weeks, Brent, usually a core feature is

included in one of those. So we look for product velocity. As well. So you probably have that. So you have like three or four of the things we're probably looking for in that. Has your team worked together before? Are you previously the three co-founders? Did you work together on your last startup or at Google or something? One of the co-founders, him and I worked together in consulting capacities together alongside with clients. Pretty much in the last step and the other one is known. Great. So that's another thing. We like people who've worked together before because we've seen that have greater, you know, greater. success. So you've got a couple of the checkboxes we like to look for. Congratulations. That's awesome. And that'll help you in your journey, I think, um, with this. So you could raise based on those factors from seed funds, potentially from angel investors, just on like, hey, here's the pitch. This is what we're going after. You might be able to get 25k to 250K checks. Where are you based?

I'm in St. Pete, just outside Tampa in Florida. Yeah. So there's no VCs there to speak of, angel investors, maybe, but you're in a tough location, right? So if you were based in Silicon Valley and you were meeting with people, this would go a lot faster, like 10 times faster because you could be meeting with folks all the time and showing your progress. Generally speaking, if you can get the product launched and get 10 customers for it, people would love to see that because now you're off to the races. And then that unlocks about, you know, 50 times the number of investors. who just want to see a little bit of early product market fit. And so your instincts are correct. You're living way outside, you know, Silicon Valley, New York City kind of Austin hubs where, you know, there might be some VCs who, oh, you're local, we can meet together, you've got a track record, sort of, you've worked together before. You might be able to convince them to do a little pre-seed investment because you're in their

backyard, but being in Tampa all the way away from the action, going to be hard. right? So then I think you do have to prove it. I would get the product launch. I get to 10 customers and then start talking to them about it. You're going to have to perform two or three times your Silicon Valley, New York, Austin contemporaries to get the funding. So just be aware of that as well.

It is what it is, right? Yeah, right. That's it. So good job. And yeah, customer traction is great. And then you could, you know, take 10 meetings with seed funds. And then the other thing is, you know, is you could join an accelerator or an incubator.

And that hacks as a validating proof point because you would have to beat out, like, for example, in our accelerators and our pre-accelerator founder, university, you're going to beat out 90 to 99 percent. Pre-accelor, you have to beat out 90 percent of people. Accelerating, you got to beat out 99 percent of people. YC, excepts one and a half. You got to beat out, you know, whatever it is, 98.5 percent of the, you know, 100 people. So if you can get into a higher-end accelerator, that can be.

also be the start of the validation process. You got through that filter. And seed funds do look at that. They'll say, oh, this person got through the TechStars filter, the launch filter, the YC filter. That means something as a first level pass. But ultimately, the good investors will want to talk to your customers and ask them, hey, what do you think of this product? How good is it?

Right. And that's going to be the big unlock. Yeah. That's all right. All right. Well done. I think we have time for one more. Okay, Oliver, what's your question?

question. Thank you. One question pretty much just on the initial push for customers. So we serve real estate agents and real estate brokerages. We're getting a lot of interest from brokerages for like a complex solution, which would be a heavy build-out, but would also be like five or 10 grand a month. And then we're also getting interest from agents, which would be like $20 a month. So we have like 23 different brokerages on wait list, about 2,500 agents. And we just don't know which one to prepare manpower towards initially. So we go lightweight and then add or, or Yeah. So you're now getting into total addressable market kind of discussion, Tam. So how many real estate agents are there in the United States right now? It's hundreds of thousands active and over a million who've got the certification. Am I ballpark correct? Yeah. Do you know the exact number of active real estate agents? It's like 1.3 million total and then about 20% of them do the majority of the business. About half of them sell more than one deal a year. So got it. So. If 20%, you think there's 300,000 people who are in the $20 a month, Tam?

Yeah. Okay. So $20 a month, $300,000. If you capture the whole thing, $6 million a month, $72 million a year. Pretty good. Pretty good. Question is, $20. Would they pay $50, you think, if you added features over time?

Yeah. So it could double in terms of those individuals paying for it. So it could go from $20 to $40, maybe even $100 a month at some point. Seems reasonable? I think it's reasonable. Definitely. Right. So what that means is the 72 million, there's room for it to 4x in terms of how much you charge,

or 5x in terms of how you charge. And now you got $350 million, $10 for them. Now, for brokerages who would pay $5,000 a month, $60,000 a year, how many of those do you think there are? Like the regional brokerages, probably like 2 to $3,000. That would have good targets. Okay, so $3,000. And you think $60,000 a year. So now a thousand at 60 would be 60 million.

3,000 at 60,000 a year would be 180 million. So they seem like similar TAMs. So then the question becomes, you know, are there competitors for either of these products in the market? And is one of them going to be harder to displace than the other? It's another way to look at this. What's the answer to that question? Do you have more competition for going direct to brokers

or more competition with the $5,000 a month solution to brokerage houses? Like going direct to agents, there's not a lot of brokerage solutions currently. Yeah. So, you know, if you can get those brokerages to put down the money, then you're a SaaS business. And it feels like, you know, you could have a sales team and an onboarding team and a customer success team and land and expand and raise prices over time. And then you've got a smaller number of targets to go after. you just could have somebody in Manila, you know, research 3,000 people

who have these agencies put their names into a database for you. And then you're just going to spend the next 10 years seeing of those 3,000 how many you can get. Now, if you were going to do the one for brokers, you're going to have to figure out a way at scale to get to a large number of brokers, podcasts, Google search, influencer TikToks, I don't know how you reach them, where they hang out, message boards.

I know there's like a real estate message board where they all hang out and, you know, ring their hands, Reddit forums, whatever. And so you just have a different life where you'd be trying to do. In one case, you're going to have a sales team targeting leads, warming them up, you know, doing meetings, maybe whining and dining people. And it's a small number of people paying you a large amount of money, low churn. On the other side, high churn, high marketing, you know, having to, you know, reach a ton of them. Now, a lot of them may sample it.

So it's going to be a high churn business. But it would be more defensible, right? Because if you did get to scale with a large number of brokers, you got 100,000 brokers. Well, yeah, you're not, if you lose a thousand of them, it's no big deal, right? You've lost 1%. Whereas in the other case, if you start losing dozens of them, it could have a serious impact. So I think you know the answer to this question that you're asking. You're probably just looking for confirmation.

Was my assessment where you wound up? Yeah, it was just like a little insight. I guess. Yeah. But no, I appreciate you thinking through this. Thank you very much. I clarify a fallout.

Yeah. Have you done an enterprise software company for a B2B company before? Yeah. Is this your first company? Yeah, first AI company. I was in real estate and then I did my master's in AI. So I just kind of like know the domain.

And so we have like two pilot programs with brokerages. And then we did a conference and then it's just exploded. So I was like, oh, Twitter, we got. put it out. I like the idea of going after the big high-end folks. You could eventually, you know, if you look at something like Slack, you know, there are people using Slack with five people in their Slack instance, and there are people using it with $5,000, right?

The solution kind of works for all of them. If you make this industrial slang solution and people are paying $60,000 for it, you could always have a lightweight version eventually, I guess. I don't know why you'd want to. It sounds like if you own the brokerage, you could own the whole business. and it's going to be a much easier business. And it sounds like they want what you're selling. And it sounds like you can name your price if you're saying it's five to ten a month.

So I'd say you name your price. And let's see if they actually give you, if they pay a six months, you charge up front six months. You know, you do those strategies to make sure they're serious. Say, hey, you know, we're only going to be able to have five pilots this year. It's, you know, $5,000 a month. It's $25,000 on signing for the first six months. And then you go to monthly payments after that. Might that work for you?

And just be a little bold. And then if everybody says yes, then just raise the price, just literally double the price for the next 10 phone calls and say, hey, you know, we can only do 10 of these trials this year. And it's not cheap. You know, this is a high-end software, but, you know, it's $10,000 a month. You got to pay $60 on signing. But of course, if you sell one home, you know, your average home sells a million or two.

So it would pay for itself with but one sale. So that's all you need to determine is if you can sell one. And you may have heard on the earlier phone I did, we're always saying, like, just chat. challenge people and go after the high end first, as opposed to what a lot of founders do is they go for the low end and then they got problems later because they run out of money. All right, great job. I wish you great success, Oliver. All right, everybody, this has worked out fantastic.

We'll do more next time and we'll see you next time on This Week in Startups. Bye-bye. Hey, everybody. I talk to a lot of founders here on This Week in Startups and as an investor. And they tell me the same thing over and over again. They want to spend time together. So we've been working here on a new meetup program. We call it Founder Fridays.

And Founder Fridays are an event by founders for founders. This is an event that is hosted in cities by people like you. If you're listening to This Week in startups, you're a founder. Now, why is it important for founders to get together? Shouldn't you be at home just focusing? Shouldn't you be in the office just focusing on your startup? Well, if you get together with other founders, true founders who are in the arena, building like you are, you're going to get a lot of value from that because you can trade

notes about what's working at your startup and what's not working. The truth is, if you're facing a problem, there are hundreds of founders out there who have probably solved it already. And instead of you banging your head against the wall, when you sit there and you talk to three or four founders, somebody say, oh, you know what, I had that same human resources problem. Oh, I had that same technical problem. Oh, I had that same marketing problem. And they might tell you about a tool or a service that'll solve that problem for you. This happens over and over and over again when I do founder Fridays with our portfolio companies. Now we're going to give you that same experience, but here's what I need you to do. I need you to host this in your city. So you're going to go to

this week in startups.com slash meetups. That's it. And you'll see a landing page where you can sign up and you can say, I want to host in my city. Now, your city may already be hosting so you can just join that person. We're using a wonderful piece of software that we've invested in called River. You can sign up for a River account just by going to this week in startups.com slash meetups. And we're going to do these on a rolling basis. You can join an again. existing meetup, if it's already occurring in your city, or you and one or two other founders can start your own. Please go to this week in startups.com slash meetups if you are a founder. This is for founders by founders. We vet everybody to make sure you're a founder. And if you host it,

it's a non-com commercial event. So this is your chance to connect. Go to this week in startups.com slash meetups.