Why must I learn to build again to compete with AI?

Ep 109 Jess Mah Transcription Jason Kirby (00:15.556) Everyone welcome back to a hundred million dollar exits. Today I have Jess Ma on the show with us, a founder who started her first company in college, led it to a nine figure valuation and has since founded over 10 plus companies to evaluation over a billion dollars across them all. Jess, you are very welcome to the show and I'm excited to talk about your experience building in Silicon Valley and what's happening in Silicon Valley today with all the rapid developments in AI. Jess (00:50.424) Thank you. So excited to be here and thanks for inviting me. Jason Kirby (00:56.146) So Jess, you have a fascinating story in of itself, but it's been heard before you, you've been on another podcast. You've shared these stories about what happened with Ingeniero, albeit a very interesting and fascinating story of scaling the ups and downs of that business. You've since gone on to do many other things and you have your ear to the pulse or finger on the pulse in Silicon Valley in terms of what's going on, what's happening. And I think that's going be a far more interesting topic for our guests today, trying to figure out how the hell do we navigate. What's going on when there's a million different companies starting up with AI and how everything's changing so rapidly. So with that intro, I'd be curious to just kind of hear what you're seeing right now. And then we'll start having some conversations about what founders can do to prepare. Jess (01:41.932) Yeah, sounds good. I would like to start by just sharing that I've had many ups and downs over my career, probably more downs than ups. And I think most entrepreneurs would say the same. recently I have been spending a lot of time with friends who built phenomenal companies, unicorn companies that all of you would have heard of. And I'm having lunch, I'm having dinner with these folks and the anxiety right now as of March, 2026, it's astronomical. It's through the roof. mean, these people are barely sleeping, Jason. Okay. These are people who you and I would read on the news and think, my God, you are super successful. Okay. Last week I had dinner with a friend of mine whose company just raised on a multi-billion dollar valuation and you know, all over the news and you know, All the announcements on LinkedIn with a, you know, raised nine figures from these species, blah, blah, blah. And so I read them like, my God, this guy feels like he's on fire and he's set. meanwhile, we're hanging out and he's on the verge of a panic attack every single day. And I'm thinking that's not good. And so he's asking me for advice on how to deal with that. And I'm like, well. Ironically, by not having as much success, it makes it a little bit easier to learn how to deal with these things. And by having so many downs in my career, I've been so practiced at this, but this example is not isolated, Jason. This is, I'd say, the norm. And so you're going around at these conferences, people have another... persona, right? The persona of I'm winning, I'm crushing it because they're trying to sell, they're trying to get customers, they're trying to get big enterprises to adopt their solution. They're trying to raise more capital. So to be able to actually get a pulse on what's going on, it's very difficult unless you're having these one-on-one conversations, ideally in the heart of Silicon Valley in San Francisco. So that's what's happening right now in a nutshell. It's very stressful times here. Don't trust what you read in the news. It's largely fake and manufactured. Jess (03:49.076) It's, yeah, mean, happy to go into more detail, but that's my read on what's going on. Jason Kirby (03:52.925) So, and so when it comes to these anxiety levels, like you look at the Elon Musk of the world, which everyone points to as very public and visible of his high levels of anxiety and like intense, you know, days of impossible work hours. Is that just the nature of these founders or has something changed? Did he not take second or he or she not take secondary in that big transaction and feeling a little scared or, you know, did they get secondary and they're just naturally just. Jess (04:06.957) Yeah. Jason Kirby (04:21.83) scared for what's around the corner. Jess (04:25.344) Yeah, I mean, I think for me and for a lot of my my peers in business, it's actually not financial, Jason. I think if you don't have any money, if you're struggling financially, you you think that it's about the money. But then when you actually pull back the curtain and talk to these folks, it's about relevancy. It's about importance. It's about ego. It's about like, well. And in this case, yeah, these founders are taking secondaries and they have side hustles that make money. So it's not about that. They think it's about that. They're like, okay, I got X million off the table. That's not enough. actually need, you know, I'll feel better if I could take 30 off the table. But that isn't the satisfying thing. They're actually worried about the existential threat posed by AI to their business. Sorry, I'm gonna pause for sec, my dog here is going fucking crazy. What the fuck are you doing? You're ruining my fucking podcast. I was on a roll, Luke. Oh my God. What is wrong with you, Luke? I love you, but I'm gonna give you something to fucking stop on, so you just fucking stop bothering me. Jason Kirby (05:19.816) Yeah, I'm just gonna pause because your dog's going nuts over there. Jason Kirby (05:28.904) you Jess (05:42.22) That's like very noticeable. I can see it on the microphone. Jason Kirby (05:46.076) Yeah, the audio level's peaking. Jess (05:48.622) Yeah, I know. All right, here, Teresa, go away and leave me alone. All right, so where were we? I'm sorry, is there a good pick-up point? Jason Kirby (05:57.393) Yeah, you hit your point. So we'll kind of just transition to the next question for me. So that's why I asked that question in terms of financial, because when it comes to what I see is like the billion dollar founders, like the ones that are truly unicorn founders, that I would say is more the attributes that I picked up on is relevance, scale, power, influence, is more of what they're concerned about. So what is happening now? Jess (06:02.062) Share. Jason Kirby (06:26.908) that you think this level of anxiety is increasing when it comes to those attributes being threatened. Jess (06:34.498) I think it's a lot of what I went through, Jason. mean, throughout my 20s, I felt like I was on fire. I thought I was unstoppable, you know, on the cover of magazines and featured in the press in a very great way. And then now I'm in my mid thirties and no one cares about me, Jason. Okay. Like now it's about the cool AI kids who are like 22 years old with like, you know, $10 billion companies. And if you look at Y Combinator, the famed accelerator that's responsible for, you know, Coinbase, DoorDash, Stripe, all these hot companies. And I went through Y Combinator. I was mentored by Paul Graham like over 15 years ago. I read all his essays through college, was totally obsessed and enamored by him. And I wrote a few blog posts that got to the top of hacker news. And then he emailed me saying, Hey, like you should come to Y Combinator and join. And I did. And, and Y Combinator today, they are still producing very good companies. I the talk of Y Combinator being irrelevant and dead, I think is total nonsense. Now granted, there's a lot of companies in Y Combinator and not all are going to be good, but there are going to be a lot that are great. And they are taking on kids who haven't even finished college yet, who study computer science, who are just very, very fast at building and shipping and deploying product. And I think that made me realize, my God, like I am becoming less relevant right now if I can't move as fast as they can. And so that basically caused me to pause for the past. basically 12 months, Jason, to recalibrate and get back to building myself hands on, which sounds ridiculous because I've had many hundreds of employees reporting to me. I've hired thousands of employees across my career. So I thought I was past all of that. I'm like, yes, now I get, just manage and operate from a strategic level, right? Like all that, all those buzzwords of like, all right, now I can, you know. Jason Kirby (08:40.141) Ha ha. Jess (08:44.684) be like strategic and not have to do. Well, that's completely backwards now. Now at the highest levels you have to do. And if you're not able to do, then your products are gonna fall behind and your whole strategy, you can't execute it as quickly as you want because you have to wait to hire other people to do it. Like AI's completely flipped that on its head. So for me, a few years ago, I thought, okay, I'm gonna be able to build a system around me, hire a bunch of people who can help me start a bunch of companies and incubate a bunch of things. And today that's absolutely not true. Today, I'm personally working on an idea and I'm personally going to build the product website prototype, because if I don't, it's going to take another two months to get to realize this vision that I so clearly have in my head. And because we don't have like Neuralink yet or, you know, whatever way to plug into my brain and download what I'm thinking. It, it's too time consuming. to communicate what I want than for me to just build it now with AI. And so you might say, that's not so bad. I'll just take you a little bit more time. No, it's terrible, Jason. It's existential because my competitor could just build it themselves. These YC kids who are working 9-9-6, which means 9 AM to 9 PM, six days a week, and living on pizza and ramen and study computer science and just finished like six months ago, that's your competition now, you know? Jason Kirby (10:15.108) And what I also want to bring up about that is like, they now have access to the knowledge and tools of, you know, the, the, the most elite to, you know, the bot, like it levels of playing field in terms of access to be able to build something like you don't have to have 10 years of experience in, you know, Python react, you know, whatever language, your product language you need to build something from scratch. Like you can just have persistence. think that's one of the most important things with AI is I build things myself. I'm just like, it's like, okay, I know if I'm to start this, I'm going to have to do this for the next like four to six hours uninterrupted. Otherwise I'm not, I'm not going to make any progress. So I have a filter for everything I do, as you kind of see, you're seeing this and you talked about these, you know, unicorn powers that are experiencing this level of anxiety of just like, how do I compete? How are you? Jess (10:45.376) Yes, exactly. Jess (10:59.894) Mm-hmm. Jason Kirby (11:14.576) How are you seeing them respond? So it's like, okay, they have the anxiety, they have the concern, they have the feeling of threat, but how are they basically turning that into an action? And what are you seeing them do? Jess (11:28.054) I'm seeing them not react to this gracefully, to say the least. So it's kind of like there are a few stages, right? There's just like basic fear of being irrelevant or having their company go under and or just falling behind, right? Like I know one founder whose company indirectly competes with cursor and cloud code. And, you know, he's got a unicorn and now his product is falling behind and now he's worried that the whole business will implode in the next 36 months. Right. Then meanwhile, yesterday I had lunch with an engineering lead at cursor who talks to all of these customers and says that a lot of these engineers at these companies. that are YC backed even, but they're unicorn companies now, well-known companies, including some that I mentioned. The culture is actually not as fast moving as you would think. These are engineers who are now mid-career and they're like, why are you telling me what to do? I know how to do things. Like I, you know, I am, you know, using AI to code. like stop micromanaging me, but. But they're only applying the stuff from six months ago. And what's been released by, Cursor this month is already going to level them up by 20%. And the point being that these founders aren't taking as much of a top-down approach to this as they should. A lot of them are still. running their engineering teams and their product teams and their companies in a very like, you know, kumbaya, like, all right, like it's, we'll figure it out together. What do you guys want to do? We're going to empower our workforce, which works for many other things, but for transitioning into this new AI first culture, I don't think that works. You have to be very, a bit more. Jess (13:28.462) top down and demanding candidly as a CEO if you're going to pivot your culture successfully. And then also your other question on their psychology, right? It's like, that's another problem. Because if they're just like feeling burned out and like scared all the time, there's only so much work you can do here. know, a lot of that's internal and you you don't want to fry yourself out in the meantime. So we could talk about that as well. Jason Kirby (13:54.921) So how, maybe you can share a personal story in this regard of like this choice of like, you had an engineer, had like hundreds of employees, thousands of people. We went from this culture of scaling by head count, like you scale with head count and now you you scale with head count and then you go into this world where it's like head count. Isn't necessarily the driver for success. And it could be a liability in terms of scaling with headcount. How, how should founders be preparing for this shift? How should they be, or like, I'd not say like, how are you preparing for this shift? Jess (14:39.778) Well, I have the gift of starting a lot of companies from scratch right now. And in my work now, we are structuring these teams and companies to not need a lot of talent and to be seven figure, eight figure ARR companies with only a few employees. And I've got a few examples of that right now where we've got contracts lined up, making several of my companies, seven figure, eight figure ARR companies, once. you know, a certain feature or product set is delivered and being able to have that commitment lined up before I devote resources to something. That's pretty unusual, but that's unlocked now in 2026 because I know I can move so fast and deliver a promise within a few months versus a years ago that could have taken years. Jason Kirby (15:28.136) So this is very important. I literally just got off a call with another founder and I was telling him, he's like, you know, Hey, I'm going to start raising money. And I was just like, you know, he's a friend. know him well. And, um, you know, it was too early for most, you know, capital, for most capital raises. And I was trying to have a conversation with him. like, look, like the bar has moved dramatically in terms of what's expected. a seed stage round of raising a couple of million dollars or whatever it be, like has moved to where it's like, need a couple million potentially and like rapidly. And I'm like, well, that's, crazy. Like, how's that possible? It's like, that's what everyone else is doing. Like there's enough people that are having these insane ramp ups because they just, they tested and iterated fast enough with AI to figure out what actually worked and then got to market as fast as possible. failed, tried something else, try, you know, and that's like in a week or two weeks worth of time. Whereas historically, you know, if you have team of developers and you're going back and forth, it would take a couple of months to kind of have that kind of, iteration. so that's kind of, and I'd be curious, can you get your take, especially in Silicon Valley, like the. Expected ramp up of traction and how you're seeing that divvy up between say more complicated deep tech AI type products versus like application layer. And what are you kind of seeing get funded in those kind of early to mid stages? Jess (16:59.374) It's a lot harder to get funded in the early and mid stages. mean, a lot of my friends who are GPs of funds are focusing on second time founders now and third time founders. So it's a bit harder for the first timers unless they go through Y Combinator, I would say, or something like that. Deep tech is totally different because they need capital still. But yeah, I mean, I totally agree with your assessment, Jason. The ramp up, the expectation is totally different. Jess (17:28.308) And I think everyone's trying to get used to that now. And also I think what a lot of founders don't have perspective on is if founders make friends with a bunch of GPs, it would be really helpful for them because then they realize how there are so many companies that look like them and sound like them. And like, I'll see a deck, I'm like, oh my God, I've seen like 20 companies just like this in the past year. It's just too easy to have competition. So the obvious ideas are no longer viable anymore, unless you are a repeat founder who already has connections in that industry and customers lined up. Without that and some other uniqueness, it's impossible. And yeah, mean, how do you see with that? Because you see so many deals too that probably look identical. Jason Kirby (18:11.538) I get it. Jason Kirby (18:17.256) And that's why I try to tell people all the time. It's just like, so many founders are just like in the weeds, like I'm building my dream and building the future, blah, blah, blah, blah, blah. it's like, cool product, bro. But there's 40 other deals just like yours at your stage. Like how are you truly differentiated and how it's an oversimplification. Cause like, I think there are cases where founders have connections with investors and they're shooting the shit and they get an agreement. Jess (18:26.264) Hi. Jason Kirby (18:47.186) You like they get a term she relatively easily because they have a trust of relationship. Those things are, you know, happen all the time. It's not the anomaly. It's just not visible for everyone. But then there's like founders that are just have to bust their ass off and run a proper process. If they don't have traction, if they don't have the ramp up and acceleration, cause like I've seen definitely people get funded at the first million, 2 million relatively easily. If they just have a generally good team and a good idea, but it's that next round. like the seed stage round has become like it was series A was like the big wall and now it's like moving to seed. It's just like, Jess (19:22.638) It's all, it's all language though. Cause like the seed rands from when I was doing a seed round, it was like half a million to a million bucks. Right. So, so yeah. Jason Kirby (19:30.344) Yeah. And that could still happen, but it's, you know, well, in terms of raise back then, yeah, it was about a half a million million. Now it's like two to 10. Yeah. Jess (19:36.398) It's a small amount. Yeah, exactly. Exactly. It's just so crazy, right? But there's no pre seed concept when I was going. It was seed series A pre seed. Jason Kirby (19:45.577) Yeah, was Angel and Seed and like Seed was relatively new in like the kind of early 2015 or 2010 and stuff like that. And so what I tell founders is like, what will you win? Like what niche will you win? Cause like everyone's like, well, I to be a billion dollar company. I got to have like a billion dollar outcome. So they boil the ocean. say like, oh, we're going to do everything. It's like, well, no one, no one believes you're capable of that today. Jess (19:51.894) Yeah, exactly. I know. Jason Kirby (20:13.224) So tell me like how you're gonna win one thing and be the best at one thing and how that creates a wedge for an expanded market opportunity once it's appropriate. And I'm here. Well, from yourself. Good. Jess (20:22.678) Yeah, that's really well said. But how do you, yeah. Cause like you see so many founders, like, like, are you seeing that the repeat founders, are they able to adapt and, you know, get on top of all the AI stuff or do, are a bunch of them having trouble because they're thinking, okay, I already had some success. Therefore this should be easier. Jason Kirby (20:49.064) It's mixed bag and like running. So being in the post-exit, the founder community, which are both members of, I run the London chapter here and I see. I see the range. Like I see the venture studio path, which is a similar path that you took where it's like, I don't want to do one. I want to do many. And, and they, you know, feel like that the Midas touch, a lot of those don't work out a lot of those, you know, they try for a little bit and then if it fizzles out, I would say the general theme I see is like, if they made enough. They either have the ego kind of pieces that you talked about in terms of like, they want the influence, they want the relevance, they want the ability to create and they will build. And they are the ones that are adapting relatively quickly. The, they're going into something new, where the ones that had had a success way back and they already have another successful company now, not seeing them iterate as fast. and. kind of waiting like, let's see where this plays out as opposed to like getting ahead of the curve. Um, and so I see the different range, but I would say like, what is just a big stark difference between like a beginner first time founder and a repeat founder, uh, in today's market. It just depends on the, I hate to say it, but it does have an age quite a bit. Like the younger founders just go straight into native AI and there's just not even a concept of what was. And the ones that have been in the game for a little bit, trying to replicate their old playbook. And those that are trying to play their own playbook, not like, I'm like, sorry. It's like it worked before, but it's not going to work now. Tough conversation. Jess (22:33.626) Yeah, well, mean, a lot of it's really tough conversation. A lot of a lot of people I've had conversation with say that investors in Silicon Valley are sexist and ageist. And there's a bias towards the young 22 year old male founder. And I believe that's the case. just based on the data and what I've seen from like women getting funded, younger, know, men versus older men even. And, you know, since you're not an employer, if you're, if you're, you know, funding companies, you don't have any liability there, but is there still like a bigger, you know, cultural problem we're creating by having this be so Jason? Jason Kirby (23:30.696) What was that? Jess (23:32.186) Is there a bigger cultural challenge that we're creating by the fact that we are disproportionately not funding women and not funding more... Sorry, someone just like went, my fiance just went through the door and now it's like, I took him out. Yeah, but he's just being annoying and I'm trying to record a podcast right now. Thank you. Okay. I'll say that again. Yeah, so Jason, are we creating a cultural problem by the fact that we're not funding women as much according to the data and we're not funding. Jason Kirby (23:48.528) Ely wants to be a part of the show. Jason Kirby (24:00.33) So ask that question again on the funding. Peace. Jess (24:15.498) mid-career, later-career founders who have a lot of experience who might not be as on top of the technology. It's kind of weird because you are allowed to discriminate as an investor. In fact, in the investor circles, I believe it's actively encouraged based on what I've been reading from a bunch of these chat groups I'm in. But Also, it's a bit unnerving at the same time and I'm trying to make sense of it and curious if you have an opinion. Jason Kirby (24:51.175) I do. see, you know, it's obviously been a hot topic for years in terms of the, the lack of diversification or diversity in capital allocation. And, you know, it's just, it's a natural progression of where capital concentrates typically middle-aged older white men who know middle-aged, you know, like no more white men, that they typically just are in circles with, they trust more already and they will do business amongst themselves. And it's a self-fulfilling prophecy that creates pattern recognition. And they're like, well, it worked. You know, it's not to say that had they gone out of their comfort zone and, you know, listen to other people, you know, women, people of color, whatever it might be to, you know, actually see them through. It's just so much easier for them to justify the pattern recognition than it is to. And ironically, I always hate saying it's like, take the risk. It's like the whole fucking job is to take a risk. Um, but. They don't take the risk on kind of unproven, you know, founder or pattern recognition. And so whether that's right or wrong, it's what's led to such a minuscule amount of capital going outside of, you know, kind of a, you know, non-white male capital in terms of founders. And also I think there's a natural progression for people typically have more of a comfort. so like the, the people that get funded typically have come from a more comfortable life, had more access to better schooling, better networks, better resources. And so therefore they have, you know, more doors open for them to pursue this or those that come from more adverse backgrounds. They don't necessarily have those connections nor the means to not make an income for a year or two years. And, you know, take those types of risks. So that's a general theme I've seen. whether you know, it's unfortunate for greater society, because I think if women were in more empowered positions of power, we probably wouldn't have the wars and conflicts that we would have today. But just just the first opinion. But so I guess from Jess (26:56.428) Yeah, I agree. know. I mean, what this is kind of forcing, which is kind of interesting is a lot of the women I know, because I have a few groups where it's just a bunch of women who are entrepreneurs. And in the past, it's been a lot of like griping about how Silicon Valley is sexist. And one of the things I tell all these women is how In many ways, it's a gift and a blessing that it kind of forces us to be so much more on top of our unit economics, so much more efficient with how we build our businesses. How do we do more with less? And obviously, it's not ideal of a situation, but how do we turn lemons into lemonade? sometimes people get around and, Jason Kirby (27:43.273) How are you seeing, how are you seeing women in these groups? cause like it's, it's so unfortunate because you're sitting there, like you're talking about pragmatic business, you know, economics from like a women's leadership. And like, that's typically the direction I see. I've usually meet women that have just more, like better run businesses from the get go. Cause that's the benchmark they have, whereas their counterparts, that are raising obscene amounts of money. Yeah. You know, typically men. They don't have those at all. And they're yet free to, you know, kind of sell the vision and sell the story and not so much the economics of the business where women are being kind of told, you should just run a better business. Well, despite that's not where the capital really goes in venture. Like what's kind of your perception, perception of that. Jess (28:34.286) I agree with you that a lot of women have better run businesses and I think ironically it creates a perception from lot of the male VCs that, okay, this is a better run business, but that also makes it like less likely that this will be a venture scale outcome. So it kind of like, it kind of supports the story of, okay, this is a good business, but not meant to be a venture business. And then of course all the women are like, my God, this is so crazy. This is so terrible for us. Jason Kirby (28:50.62) Yeah. Jason Kirby (29:01.394) You Jess (29:02.29) And it's like, we're running better businesses, but why don't they see that this is fundable? And so in some ways, actually, think AI is going to be the great equalizer here because it will enable anyone who's motivated enough to just get more impact. Now the businesses that I'm starting, I'm probably not going to have any of them funded, a lot of them. I'd say of the next 10 businesses I start, my guess is that eight of them won't. take any outside funding. Two out of the 10 might take outside funding. If I really see that it could be a venture scale outcome, but why do that if, you cause a lot of, you know, the founders I talk to, they say, oh, I raised all this money, but you know what? Secretly, I'd be happy if I could just walk away with 20 million bucks. I would be thrilled with that outcome, but don't tell the VCs that's how I feel. I hear this all the time, Jason, all the time. including from my unicorn founders who were like, yeah, I got a few million off the table, but if I could just get 30 off the table and if the whole thing shut down, I wouldn't care that much. I hear that, you know? And so that's just to me, well, if you could own 100 % of this company and just get it to, you know, 5 million in ARR and, you know, just pocket the profit, you don't even need to sell the company because you have the cashflow that you generate from all the money you get from secondary that you have to reinvest anyway after tax, you know? Jason Kirby (29:54.276) every day. Jess (30:21.688) and figure that whole thing out too, right? So you could get to that outcome in the next 12 months on your own with no funding. That's really special. And so that's my other way of putting a positive spin on this for women and for minorities and for people who are having more trouble raising capital. But that also might just be my optimism, Jason. Jason Kirby (30:48.072) I think it's mission critical to have the optimism if you're building companies. Building a company as a pessimist is a bad place to be. Let's kind transition to that. You've raised capital. You've built a nine-figure business in the past. You've had that trajectory. You've had your ups and downs. You've made the decision for yourself that it's not go big with one company or not even go lifestyle business or like profitable business with one company. Looking at 10 companies. So I guess walk us through the decision process for you to decide on why 10 companies or like, you know, maybe more, but just like why you chose the businesses you chose to build the way you built. Jess (31:30.798) I get asked this question all the time, Jason, including by my fiance, who's constantly like, why don't you just focus on one thing? Put all the wood behind one arrow. My mom says the same thing. She bootstrapped her business and created a great business that's done hundreds of millions of dollars in sales and just had one thing. Jason Kirby (31:39.153) Just do one. Jess (31:53.806) I have a few friends who are parallel entrepreneurs, as I like to say, meaning they like to have multiple things going on. And I asked all of them, like, why do we do this guys? Like, wouldn't it be better if we just did fewer things? And the answer across all of these people is the same, Jason. It's, that would be the optimal thing to do, but I'm just not wired that way. If this was purely an IRR maximization play, then maybe that would be their better approach. Find one thing, do it really well, do it over and over and over again. But I think what's beautiful about AI is that it makes it so that actually that is no longer the case. IRR maximization may actually be more possible with the strategy because it's so cheap and easy to create many things and get them to scale really quickly. So two, three years ago, I would have agreed with that today. I'm not sure I agree with that assessment anymore. so to directly answer your question, a, I think it's more fun B I think you see more, more, different industries. could build out more expertise areas. could apply your expertise to multiple things. and, and also you don't know what's going to hit sometimes, right? I've started a bunch of things that have not worked out and And most things will not work out as well as I want them to work out. would say, you know, 90 % of these projects will not realize what I want to see happen. And so you kind of have to try more things anyway. And also if you think about some of these companies, like look at Alphabet, is Alphabet really just doing one thing? No, Alphabet does like, they have a ton of different business lines, Amazon, Microsoft, you know, same thing. Jason Kirby (33:41.232) Yeah, in all fairness of those companies, they have one mega cash cow that funds everything else. Jess (33:45.23) They do. They do. But if you're an entrepreneur, you could argue the same thing. If you're a multi-entrepreneur, you know, you have one or two things that pay your bills and, you know, and then you have the freedom and the flexibility to try other things. And if you want to have fun with that, you know, by all means do it. But is it the optimal strategy, Jason? The question that that's the ultimate question. The answer is I don't know. And I don't think for a of these multi-entrepreneurs that that's what they're optimizing for anyway. Jason Kirby (34:14.984) That's fair. What are you building? Jess (34:18.67) Um, I'm building a lot of different AI businesses that are in stealth right now and that I'm not posting anywhere and I'm not talking about them. And I'm not talking about them for a few reasons. One, because it's just so noisy and loud out there. it's too easy to copy stuff right now. Um, and three, um, yeah, I just, uh, I just like building in, in quiet right now. I think I spent so much of my career being a bit too exposed where I was too clear, like what my ups and downs and left sprites were. And I think in the age of AI, you know, you see all these companies that are bragging about how much money they raised and how much growth they have and how much revenue they have. think right now it's actually better to be a lot more low key and quiet and humble because yeah, I might have a few businesses that are going to be great this year. Get to, you know, mid seven figures or low eight figures, but they might be out of business in three years from now, Jason. So if I'm here bragging about them and then three years from now, that business is like nothing because of AI. I got to a great point because of AI and then the business totally went out of business because of AI. That's going to be embarrassing. So I want to just recognize that head on that that's a real vulnerability and risk here. And I don't feel comfortable. don't think entrepreneurs, if they feel too comfortable, then that's not a good feeling either. But I don't think it's good either to be so paranoid. and be so nervous that you can't enjoy your life either. There's this balance that has to exist energetically in order for an entrepreneur to create from a positive place. Jason Kirby (35:58.281) So when you're looking at building these companies, you won't disclose, which unfortunate, but when it comes to the, um, the actual bill, like, are you building this entirely by yourself? You, you vibe coding to the point where it's like in market and you're creating like agents to do the marketing for you. Are you assembling teams? Are you hiring like a CEO to take it over? Like, tell us a little bit about how you think about. the way these businesses should be built, knowing the existential threat that could exist. Jess (36:31.136) Yeah, I like to build with partners. I think it's really fun to build with other people. I don't like to build solo. I think right now it's really important to have multiple perspectives on an idea. So I'll find a friend. We're having lunch, we're having dinner. So it's like, all right, Jason, we're hanging out in London. I'm visiting you and you're telling me about like, yeah, there's this like interesting opportunity with, you know, water sanitization plants and like. The software is really bad and the service providers who help monitor them, like they're antiquated and we could create this cool thing and I already have the connections. and they would pay tens of millions of dollars for this Jess, but I just don't have the time. got like, you know, I'm running thunder right now, but I wish I had the bandwidth to create this and, and, and, and And let's just assume Jason, you're not in technology, you're not an AI, you're just a random, you know, you know, person who has great sales connections. So this is an example. I'd be like, awesome. I'll just like throw in five engineers. I've got a ton of engineers in Latin America. And, you know, it'll cost pretty much nothing to fund this because it's so cost effective. You already have con you you'll get the contracts lined up. And then boom, we're in business. And so I'm finding probably one or two opportunities like that every single week right now, which I might do one in three of those. So that's why I have dinner. That's why I go to lunch. That's why I'm traveling all the time to like find those hidden gem opportunities that are just very opaque or in some very non-obvious area where only you as a domain expert in that area would have actual knowledge and connections. I really like those ideas because they're non-obvious. You're not going to read about that in TechCrunch. You're not going to see that on LinkedIn. It's not that sexy. And they're abundant. They're everywhere. Jason Kirby (38:39.622) Yeah, I'm glad you say this because this is something I encourage people to do. And this is what I did before I launched Thunder. I just met with people all the time, just like have coffees, have lunches, have dinners, host dinners. And I think it's, you know, for a founder that's like in the midst of building and like blitzing their, their market and whatnot, maybe not the highest priority, but for those that are exploratory or trying to figure out the edge, or have reached a certain level of success where they have. real teams underneath them and they need to see what's coming. I feel exactly what you described is one of the best ways to have your kind of your pull. I have the finger on the pulse of what's going on in the market. What are the opportunities that could happen? Like I know open clog kind of like took the world by storm the last couple of months. I have an avid user myself and now integrating like cloud code remote and all these different things. Definitely think this feature, but like I'm so like at the You barely scratching the surface in terms of this true capability. I'm like 10 million tokens in, you know, measured by tokens. but for, like I, I host lunches and dinners and events. Like I'm hosting an, an event on Wednesday about poop and claw. Like, that's secretly for me to get a ton of input from other people that are passionate about the topic. it's how I hacked college. would. Organized study groups and never study. I would just listen to the smartest person in the class, you know, talk about the topic. I'd organize it and put it together. And then I've the benefit of all the data that came from it. and so I totally agree. I think it's one of the smartest ways to spend time, especially after you've, you have the clout to kind of meet with people that are, you know, maybe have a more influence or a broader perspective on the market. when you look at how you choose to spend your time. with these, with the people you're going out with, like, how do you choose? How do you choose who you do? reach out to them as it's serendipitous. They kind of reach out to you. Like, how do you manage your time on who you spend time Jess (40:50.486) It's usually pretty meaningful. It's someone who I feel like I'm interested in learning more about. their what's going through their head and you know what they're working on and yeah I'll reach out and I'll say hey I'll travel to you wherever you are and I will take you to lunch or dinner and you know I'm block off three hours so we could really you know immerse I'm not a fan of like 45 minute coffee meetings I don't think you get any value out of those it's either 30 minute phone calls or three hour meals is kind of my general approach 30 minute phone calls or Jason Kirby (41:24.028) You say three minute phone calls. he's in three minutes. Whoa. OK. Jess (41:28.782) Sorry, 30, 30 minute phone calls or three hour meals is my general preferred approach. And also Jason, what you're doing with like the ski trip for entrepreneurs. Um, right. That's really cool because that's, that's three days exactly. So it's like 30 minutes, three hours or three days. And I'm doing the same thing, right? Like I'm doing, um, I just decided to launch an AI sleep away camp, which is going to be three nights. And it's just a bunch of AI nerds and hanging out at a hotel, just like hacking away together. Jason Kirby (41:41.448) Three days. Jess (41:58.228) We'll do a few of those this year. And then I've got a few other retreats that are three, four nights as well for other entrepreneurs and people I can do business with. So I probably have six, seven weekends a year for retreats and events I'm organizing just to be able to spend all that time with people. And I'm sourcing great opportunities through doing this and you're doing this podcast, right? You're over a hundred episodes into this and now you have a hundred friends who, know, who now will do a favor for you if you ever wanted to. right? Like, so you're doing this really well, I think, Jason. People should just copy you. Jason Kirby (42:35.464) Easy, said than done. and so, yeah, I, completely agree. And as we kind of look at the future of AI and everyone's kind of scared for the massive rifts that are going to happen, which like Jack Dorsey had squared or block, basically just laying, I think it was like 40 % of the staff. you know, just kind of seeing those types of things happen as some people adopt AI or blame it on something else. Jess (42:38.658) Yeah. Jason Kirby (43:05.274) And as AI consumes our lives, I feel it's so important for these types of interaction, like the three hour lunch, like the, human connection. Cause we can spend that time getting to know someone, understanding something, and then we can execute 10 times. fact, we work less on the actual execution with AI, which I think is how I've been enjoying my time. It's I'm getting far more done with less hours, basically less hours and spending more time on calls and meetings. but still getting shit done because like maybe we'll put together decks, models, collateral all within like 30 minutes. It's like what took me eight hours. I can have like an acceptable version in 30 to 45 minutes, which is just like insane in terms of productivity gains. Jess (43:51.214) Yeah, I agree for investors and board members and entrepreneurs. It's a huge gift, right? So now I'm spending most of my time meeting with really cool people and getting ideas. And this is stuff that you're not going to be able to learn just from chatting with Claude or ChatGPT, right? You know, if you're trying to go deep into a specific domain and really understand something. a lot of those experts, they're not blogging about it. They're not putting out publicly accessible research papers in a timely manner. Like lot of the academic bio research papers you read, this is from stuff from 12, 18, 24 months ago and stuff that if you were just meeting with them 24 months ago, you would have found out about it then. So because of that, you know, inaccessibility, Jason Kirby (44:16.252) No. Jess (44:40.148) of this proprietary knowledge still, especially if you're an investor, right? It is about timeliness. You want to know about these hot things before they become hot. You got to meet people. so in a weird way, AI is leading me to spending more time off my computer than on my computer. Jason Kirby (44:58.856) I'd say that I feel like that's the unlock that a lot of people are realizing. They see like, oh, yeah, I was going to take my job. It's like, no, what does it open up in terms of, you know, productivity? But you bring up a really interesting point in terms of like inside information or just kind of knowing what's going on. Like I was maybe the VC the other day and they were walking me through like this really cool thing that they're doing, which I can't disclose. But I was just like, like, why does why are you not talking about this more? Like, this is so fascinating. It's like, well, that's my edge. Like, why would I publish my edge? And I was like, touche. Makes perfect sense. Like, yeah, he should not. Jess (45:33.518) Yeah, exactly. And now you have to be even more careful about protecting your edge, right? That's why I'm not talking about a lot of the stuff I'm doing. Whereas before I would gladly broadcast what I'm doing, right? That's so much more important now to protect your information edge and to not have it be online and scrapeable by the LLMs, you know? And now, you know, I see the the pain to look on your face. So if you want to challenge that, I actually really welcome that. Jason Kirby (46:00.489) No, no, it's, peaking my interest. Cause I'm sitting there. like, it's a, it's change of reality. Like it was so much about thought leadership, you know, sharing your insight, you know, secrets and stuff like that. But there it's going to be such a short lived window of opportunity that kind of a trade secret model of like, you're not going to patent it. You're not going to publish what you're doing. You're going to operate in silence for as long as you can to maximize. the gain that you get because the moment it's public, the algorithms could scoop it up. Someone could ask a question and open call or clock could just build it. And you're just like, shit. Jess (46:39.402) Exactly. Exactly. mean, what, another thing that I found interesting is, when we're diligent seeing opportunities, we've spent a lot of time with experts on those expert network platforms. So GLG is a popular one. AlphaSites is another popular one. And you're paying a ridiculous amount of money per hour to talk to these experts. For those who never worked here, worked with these expert networks. Jason Kirby (46:51.816) Okay. Jess (47:05.902) I mean, you could be paying $500 to $1,000 to $1,500 for an hour with someone, but they'll find you an expert, like the world's expert in X or Y or Z, whatever you're trying to do within 48 hours. And you'll learn things that you're never going to learn by an LLM or Googling around. And that just shows that there are going to be long-term limitations to doing research with these. LLMs. And so one of my ideas was like, you know, can I just have open cloth work with GLG and like run these calls for it, but there's still so much intuition. Yeah, exactly. I, and it could probably do a lot of round one interviews actually. Like if, if money was no object, you would just have like, you know, have a Opus 4.6, you know, put together a whole brief on the questions to ask all the experts and just like negotiate with the next for network on who to call and call them all and then ask the questions. Jason Kirby (47:39.472) I just do budget interviews. Jess (48:02.412) and then synthesize all of that and then come up with around two questions and then do that. And then you might come in for round three. That would actually be maximally efficient. So I've thought about that and actually I very well may build that for myself as well. Because you want, no, it's fine. This is just a mechanism of doing work and research. And I don't think most people are actually going to do it because most people are lazy. Okay. Most people who listen to this aren't going to actually put the time and effort to do these things. Jason Kirby (48:16.642) Well now you've publicized it, so everyone's gonna do it. Jess (48:32.682) that's the saddest part of this content. You know, there's so much available content out there, on how to get better. but, but still there's this follow through component that's, you know, there, there's still the psychological gap for whatever reason, you know, Jason Kirby (48:32.968) 100%. Jason Kirby (48:49.992) I feel like just riffing off the GLG idea, like the expert network idea, the problem I have with that is I feel the nuance of how people answer the questions. Now, granted, Opus is probably capable of picking it up. I'm not sure about this. If I will interpret the impact as much when presented to me in text as I would having a connection with them on a... I feel like when I kind of hear something from someone in terms of an expert opinion, I feel like there's a way to re-ask the question or poke and dive a little bit deeper that Opus might not have that genuine curiosity to do so. Jess (49:31.02) Yes, I agree with you completely. And also with all these calls, you know how you'll do like five expert calls to understand like how to invest in whatever, like pick your thing, you know, clean energy or solar, okay? You're doing five expert calls. All of those five expert calls. Two of them are really amazing. The other three, they're okay. You got some information and you're happy with it, but it's really those top two that you want to talk to more and schedule that second or third call with, right? So at least, you know, you know, AI could get you to that round too, and do what that analyst would have done for you. So instead of hiring an analyst to have those first calls and pay a salary for that, you have AI do that, you know? Jason Kirby (50:14.184) That's true. I see a lot of recruiter products coming out promising to do that kind of stuff now. Jess (50:15.346) And Jess (50:20.256) Yeah, totally. It's awesome. anyway, we're now talking about the obvious and what everyone's going to be doing. Jason Kirby (50:25.979) Yeah. Jason Kirby (50:29.97) So Jess, with you and what you have going on, like from everything you've experienced and the conversations that you're having at your level in Silicon Valley with the Unicorn founders, like what would be your advice that we haven't covered today for founders that are in that build node? Maybe they have a couple million ARR, they have a product that's been in market for a couple of years. Like what's your advice to people like them? Jess (50:58.437) Um, so the folks who already have a few million in ARR, I mean, if they're able to get to that point and deliver that because of AI, like, I don't think those people need as much wisdom and advice, you know? Jason Kirby (51:08.634) No, no, no, no, without AI. they're, they're now they're, they were pre AI built product and now they're dealing with their harsh reality that someone could build their app in 30 minutes on a weekend. Jess (51:14.432) Okay. Jess (51:22.072) man, that's tricky. I mean, think that's just as tricky as the other category, which is second time, third time founders who built their company in an older time with a lot of headcount. And now their skillset is hiring and managing people in raising capital. That was really their area of leverage and unique impact. And I'm sure you know a lot of those people, right? Like they're so charismatic. They're great at raising capital. They're great at doing all those things. But yeah, they're kind of out of the loop now. I'd say create a side hustle business that can get to a million in ARR and do it yourself. And do it in under 10 hours a week. Do it on the weekend. Do it on nights. Whenever you can, if you can do that, that will give you the confidence that you can now pivot your business and adapt and change course so that you survive the next 36 months. Jason Kirby (52:15.794) That's an interesting way to look at it. So rather than disrupt the entity as it is with AI, go fiddle and experiment with a completely separate idea or product and kind of like a sandbox to test your theories before kind of migrating the team over. Jess (52:30.541) Yep. Jess (52:37.634) Yeah, because you want to have the confidence that you know what you're going to say before you disrupt 50 people's work. You know, you want to be able to say, Hey, like, look at what I've been doing. And like you guys, like we're not doing it right anymore. And like, was able to, you know, take on all these, you know, I built an, like, you could also make your side project, like a new expansion or, you know, adjacent thing to your business. You know, that might be your idea just to showcase your people. look at what I'm able to do. And so you're, you're getting respect from your team that you're able to get your hands dirty with stuff. B, you make some extra side money, right? So this is your backup in case AI decimates your business and you have no investors and it's just money you got to put in your pocket. And C, it's fun and you really get into it. And then you learn how to learn an AI, which means watching the podcasts and You know, like all the nerdy like coding and design podcasts online and, know, you have to obsess with over that and learn that over the weekend in order to build the side projects. And you get into this loop over a 90 day period of like learning, applying, learning, applying that you now know how to teach the rest of your team on how to have that same learn, apply framework. And then I ideally, then you have your, your team leaders, you know, creating personal development. plans for every single person every month to help them level up their skill set. And if they're far behind, then they're going to have to do extra work to learn how to get caught up. And they might not make it. And I have people in my companies who are not making it because they're not obsessing about learning and applying their knowledge. But. you know, everyone I work with now is doing that. And I think a lot of that is because I'm doing this, right? Like I have these side projects that are just, you know, I'm not spending a lot of time on and, you know, I'm able to, you know, make money on them. Jason Kirby (54:37.708) I find that incredibly valid in terms of advice for founders, whether it's like a whole separate company or like more of like build it yourself. Cause I've run into that problem where it's like in my past companies, I'm like, build this please. And then it's like, okay, we'll add it to the backlog and da da da. It's like three months later. and now it's like, I'm just going to do it myself. I'm just going to connect to our GitHub and I'm just going to vibe code this exact feature that I want. Jess (55:01.527) Yeah. Jason Kirby (55:06.414) And it will be like 60, 80 % of way there. And then I'll be like, Hey, look what I was able to do last night. That changes the dynamic. Like, like you did that in a day. Like, yeah, no, did last night. It wasn't even a day. That was like two hours. And, yeah. And then demoing into the team. think that demo culture, is now, like a prelude, like it's a must have, or for companies that really want to adopt AI is like have your team demoing, and showing up. Jess (55:06.414) Totally. Jess (55:12.854) Yeah, that's great. Jason Kirby (55:35.218) they build because it gives a little bit more sense of pride and more momentum around it. Jess (55:39.372) Yeah, well, before we transition out of this topic, have a, the friend I was having lunch with yesterday who works at Cursor. He was telling me how he is able to code extremely fast and release new product stuff immediately. like within 24, 48 hours, the bigger problem is how do you politically get everyone in the organization, all the stakeholders bought in along the way that's actually 80 % of the time and the slowdown. So you're, so your engineering, you know, skillset is actually partially now leadership skillset and like, you know, trying to pull out feedback from people. And, I thought that was really profoundly interesting. Jason Kirby (56:22.514) That's interesting. That definitely put like, yeah, especially for big orgs, like, you know, again, like founder coming in and stepping on everyone's toes or, you know, mid manager trying to like convince the app that who was who didn't do the job, like it didn't do the work. It's like, why do we need like, well, that's not in our roadmap until like 2027. I was like, but it's ready now. It's like having to manage the politics that unfortunately, AI has not fixed. Jess (56:31.362) Yeah. Jess (56:45.164) Mm-hmm. Jason Kirby (56:51.848) Maybe maybe one day when we just eliminate humans altogether, then you know, it's probably more efficient. I guess there's no point living in that. Jess (56:56.462) my God, I know, I know that is sad, but this comes to show how like when you're starting from scratch on something and when you have a really small micro team that can, you know, not have politics, that really does change the game for deliverability. So that's why now I think it's reasonable that these big public companies are getting hammered. They just can't move that fast. mean, if you look at the, like right here, we have Salesforce tower and the culture at Salesforce, you know, based on this is from friends who sold their companies to Salesforce. Okay. This is not my opinion. This is their opinion. The opinion is it's really slow. It's really difficult to get your things shipped. The amount of review and stuff you have to go through. It's so hard. And it's reasonable why it is because it's all like big enterprise and Jason Kirby (57:31.944) Yep, not going to Jess (57:54.542) everything's got to be compliant and secure and all the checks and boxes you have to go through. But then on top of that, you also have the political buy-in you need along the way, even without the check marks and stuff. Because that part you could automate away with AI. But the political buy-in is impossible. So it makes sense that if you're starting from scratch, it'll be better. And so If you could create smaller micro teams in your business, you'll move faster. But that means that if you're CEO, big part of your job right now is trying to map out what is the future or structure of this company. Like this concept of just a broad engineering team, a broad product team, and everything being completely spread out like that, where you have these choke points of approval. That, and this is, you know, again, based on opinions from my other friends who are at these bigger companies who've sold to bigger companies or our executives at companies like cursor or open AI, you know, that's kind of where we need to move to. And I say, well, have you talked to these big companies like Salesforce or Meta or whoever to like get their opinion on how hard it is to shift into this new direction? And I'll tell you the answer. The answer is there's a lot of resistance and it's really difficult to get them to do that because if they did that, they'd have to blow up their whole org, right? Like who you're reporting to will be different, right? Like the whole structure to change that at a fundamental level, that needs a top down, you know, CEO board level approach. You can't just have a middle manager say, okay, I agree. Like we should reorg this whole thing, you know? So unless you as the CEO come up with this. It's just never gonna happen. Jason Kirby (59:44.231) I think this is a really good note to, wrap on. think this was a harsh reality, but also an opportunity for many, uh, you know, founders that it's like, you, you put the extra time in it sucks. Cause like, you know, you have to basically go back to work. You know, have to really like go back to the early days, like the zero to one days to address this. Yeah. And, we saw, you know, we've covered some cases, but it's just like, I think without. That tenacity and movement from leadership or the founders, it's nearly impossible. That's why Google's, you know, that's why they came back. You know, the founders of Google came back was like to get back into the mix. Cause like they needed to draw, they needed to have that level of singularity authority, singular authority to kind of push the needle, um, to, where they needed to. And they rapidly are releasing like crazy. Like they're, they're not behind, uh, well, maybe a little bit, but you know, still, still quality coming out the door. Um, but. Jess, this has been an amazing show to have you on. I guess what would be the best way for founders or investors that are listening to this conversation that might want to follow you or connect with you? Jess (01:00:52.14) Yeah, just find me on LinkedIn, linkedin.com slash in slash Jessica Ma and, send me a DM if you want to reach out and thanks for having me, Jason. Super fun to chat. And I love these fruitful debates. And I know this has sounded, well, you know, a little gloom, but I am net net optimistic. And I think everyone has the opportunity to be on the winning side of this whole conversation. Jason Kirby (01:01:20.871) 100 % completely agree and thanks again for coming on and look forward to getting this out to our audience Jess (01:01:27.274) Awesome.