Get Paid with Manny Medina

Eric Simons spent seven years building StackBlitz (now Bolt.new), a cloud IDE that millions of developers loved but almost nobody would pay for. After raising $22 million from Insight Partners in 2022, the company spent a year building enterprise features for customers who seemed excited. By launch in 2023, those customers had disappeared. The 2021 buying mania had created false demand everywhere. "Everyone was buying everything. By the time we delivered it, we turned around and they just weren't even there. They were not interested. So there was false demand effectively."With 18 months of runway and no clear path forward, Eric faced the hardest moment of his career: layoffs, followed by one final 90-day bet on a product called Bolt.The 90-Day deadline saved themEric laid off seven or eight people and told the remaining 15-person team they had 90 days to ship Bolt before the next board meeting. They'd gotten a sneak peek at upcoming Anthropic models that solved problems they'd hit earlier. If Bolt didn't work, they'd start winding down the company. "We barely got it online in 90 days. We only made it because we had no choice."They launched with a single tweet on October 3rd, 2024. Day one: $60K ARR. Day two: $80K. Week one: $1 million. Month two: $4 million to $20 million ARR. "I've been doing startups for 15 years. I've never seen anything like it. Neither had anyone else I talked to."The customer nobody expectedBolt thought they were building for developers. Within weeks, they realized their paying customers were product managers, designers, and non-technical founders at companies. "PMs' jobs have been to write JIRA tickets, assign them to developers, and hope they actually implement it. Now they write the same spec, hit enter in Bolt, and it's done in 60 seconds instead of six business days."Bolt isn't turning PMs into programmers. It's making them exponentially better at their actual job. Companies ship in one-tenth the time because engineers review AI-generated code instead of building trivial UI changes from scratch.The Twitter hackathon that cost $100K and brought in millionsA tweet changed everything: "If I was Bolt's CEO, I'd throw the world's largest hackathon." Eric replied asking about prize pool size. Within two hours, they had $1 million committed from sponsors. Bolt kicked in roughly $100K. "130,000 people signed up. Everyone got free domains through Entry. Everyone used Supabase. ROI was extremely positive. It was probably our best marketing event ever."Why Windsurf had to sellWhen Windsurf sold to Cognition, Eric wasn't surprised. Cursor was doing 5-10X Windsurf's revenue. At that scale, the gap becomes impossible to close. "Once the flywheel starts like that, it's just harder. If you're going up against a competitor with substantially more distribution, crossing that chasm isn't realistically possible. So you find someone with even MORE distribution than your competitor."The pain tolerance that built BoltEric's early career included living in an AOL office building and eating at frat houses. He compares it to Navy SEAL training: constant discomfort that builds tolerance for the startup grind."A lot of what they train you to do is to be wet and cold all the time. They don't get discouraged by that stuff because it's normal. That's your only move as an entrepreneur: turn over all the stones and be intellectually honest about whether you see a path."Companies Mentioned: StackBlitzAnthropic ClaudeCursorWindsurfCognitionDevinOpenAI ChatGPTFigmaWixReplitLovableMicrosoftGitHubGartnerInsight PartnersPaddleSupabaseSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We invited Jonathan Sanders, CEO and founder of Light, fresh off raising their $30M A round and serving some of the fastest-growing companies in the world, to share why ERP migrations are universally hated, how his company turns 18-month implementations into one-day onboardings, and why finance teams are becoming technical writers without even realizing it.Jonathan and Manny explore the death of the traditional ERP category and the birth of smart finance platforms. From working with OpenAI months before ChatGPT launched to discovering the "student assistant" mental model that shaped Light's entire product philosophy, this episode maps out the future where finance teams configure systems by writing policies in plain English instead of paying consultants $200K to write scripts nobody understands."Think of it as a student assistant that works for you 24/7. The clearer you are in your instructions, the better a job it will do."The Migration Pain That Created LightJonathan lived through two nightmare ERP migrations at Pleo and Juni. Each took 12-18 months, cost over $200K, and required constant consultant babysitting. At Outreach, Manny's board literally told leadership not to migrate because it would be a massive waste of time with zero ROI."It's like watching paint dry and getting f****. There's nothing enjoyable about it."When Jonathan decided to build a better way, investors told him it would take 10 years and $100 million. He built it in 2 years instead.The OpenAI Insight That Changed EverythingBefore ChatGPT launched, Light was working directly with OpenAI's VP of Product:"He said think of it as a student assistant. It won't always get it right, but the clearer your instructions, the better the job it'll do."Finance teams write 2-4 page documents in plain English explaining their accounting. The AI uses those policies to classify transactions and handle exceptions. No consultants. No scripts. Just instructions you'd give any new hire.The $200K Implementation Racket Is OverImplementation consultants were brutally honest with Jonathan:"If I can't sell a six-month project, I need to sell a project every week just to make payroll. Your interests are completely misaligned with your core client."Light eliminates this entirely. No implementation fees. No consultant dependency. By design, they can't build the traditional channel ecosystem because if they depend on partners for go-to-market, they can't build self-serve products.The New Finance Skill: Writing, Not Coding"The ability to clearly articulate business processes and codify them into words. That's a new skillset coming out across all applications."Finance teams are becoming policy writers. They document workflows in plain English. The AI executes it. This replaces sending instructions to BPO teams in India or calling consultants to modify scripts.Software Should Defragment Itself "Nobody goes and deactivates unused tax codes. But if it does it for you, the system becomes leaner."Light is building self-healing software that automatically identifies unused accounts and optimizes itself. Like disk defragmentation, but for your entire finance operation.How Light Hunts for CustomersLight hunts for trigger events on LinkedIn: New CFO hired, scaling globally, hit 300-400 employees, funding announcements. The fastest deal? Saturday inquiry, signed Wednesday."Nobody migrates ERPs for fun. They only do it when they have no choice."Companies MentionedLightNetSuiteSAPOracleMicrosoftSalesforceWorkdayHiBobDeelRipplingXeroQuickBooksChargebeeZuoraHubSpotOpenAIPleoJuniOutreachAccentureSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Manny and Raj sit down to celebrate closing Paid's $21M seed round just 10 months after starting the company in an Airbnb with four people. This is your inside look yet at what it takes to build a company at AI speed. They unpack why Manny took a high valuation he's confident he can deliver on, how they closed the round with a 60% working demo, and the fuckton of arguing that almost tore the cofounders apart.The valuation question"I can sell 100 million of anything. So I'm not scared of 100 million. If the evaluation was 300 or like 250, I would be super scared. 100, I can sell 50, I can sell 100 of whatever. I'm not scared of that number."Manny explains why they took a valuation between $100-200M when everyone warned them it was too high. Sales is a game of confidence. He didn't have the confidence for higher, but he's not scared of this number. They got the term sheet when their product was half demo, not more. The key insight is knowing which bar you can actually clear.From fear to winningThe shift from Outreach to Paid represents a fundamental mindset change. At Outreach, survival mode drove every decision. At Paid, with $31M in the bank ($10M pre-seed + $21M seed) for 11 people, they have time to design the future they want to build. Raj shares how his last startup died because he avoided fighting. Now he's learned that hard conversations with experienced cofounders create purer relationships. Manny reveals the marriage lesson that changed everything: give each other grace, walk away when heated, and come back to the same problem with fresh perspective and no assumptions. Be a goldfish. Have a shorter memory on the shit that bothers you.The Palantir playbookRaj brings forward deployment to Paid. Every single one of the engineers has been deployed to customers and nobody died. The traditional setup has customer research, product managers talking to customers, feeding devs tickets. That's incredibly low bandwidth. An engineer being there, talking to customers, contains everything in their head with zero information loss. Big secret: engineers can talk to people. They can figure this out. They don't need to be locked in a cupboard.Why Winning Is The Only MetricRaj doesn't consider the time somebody spends building something as precious. He considers winning precious. Getting a customer precious. The time you take to iterate is just reps. At Outreach, they considered developer time the most valuable thing. In reality, winning is the most valuable thing. This creates different behavior. When team member Atta volunteered to redeploy customers from three months ago because the technology is significantly better now, Manny knew they had something special. No public company does that. Salesforce, ServiceNow, Workday give you code to get you over the line and you're stuck with it. They don't give a fuck about you. Paid operates from duty and pride, like a doctor with a Hippocratic oath. We found new science and we're going to give it to you whether you like it or not.The UK vs US MindsetRaj from Coventry gets asked by school friends: why are you doing this when you had such a good job? Manny nails the difference between US and UK entrepreneurship. In the US, people celebrate the ability to sell your way into financial independence and doing whatever you want with your life. Why is getting a job the bar for a university student? How about starting something? Making money? Financial independence? The UK has a class system and a culture where it's not cool to be successful. You want to be like everyone else, not upper class.But Raj sees Paid as a mechanism to get Britain building again. Not cars, that ship sailed to China. But in a world where you can talk to an AI and it builds something, if you have a real problem, you have the opportunity to sell it. The positive vision of AI versus the dystopian version that robs everyone of agency.Between Seed and Series A Is Everything"Whatever you did in the between seed and A is what you're locking in. That's a time of defining how straight the tree is gonna grow. If you ended up crooked, just to put points on the board, and you try to grow crooked by putting more points on the board, you screwed it."Not quid pro quo deals, everyone does that. It's about sales efficiency, technical debt, operational debt, culture in general. Are you devoting enough time to getting it right? Culture is like being a gardener. Making sure the soil is ready, pulling weeds, giving plants water and sun so they grow. Eventually you step back from fighting and make sure your garden is flourishing.That's leadership.Companies MentionedPaidOutreachPalantirSalesforceServiceNowWorkdayReplitSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Amjad Masad, the founder and CEO of Replit, discusses the transformative power of AI-driven agents like Agent 3, which acts as a cost-effective employee alternative. He reveals how point solutions are becoming obsolete as micro-SaaS opportunities rise for tech-savvy entrepreneurs. Amjad also explains Replit's unconventional pricing strategy, emphasizing that hiring an agent can save businesses significant money. With insights on creating a more accessible programming landscape and fostering flexibility in work culture, he highlights a shift towards a distributed economy of small entrepreneurs.

We invited Nick Holzherr, founder of GitLaw and former contestant on The Apprentice, to dive deep into the legal industry's impending transformation. Nick shares his journey from paying hundreds of thousands in legal fees for what he discovered were essentially template documents, to building a platform that automates 90% of legal work. He breaks down the shocking economics of law firms where partners charge $2000/hour while paying juniors $100/hour to fill out standardized forms, and explains why this model is about to collapse entirely.Nick and Manny explore the broader implications of AI displacing entire professions. From the thousands of qualified junior lawyers who can't find work right now (but politicians don't see it yet), to the mind-bending tax revenue crisis coming when AI agents replace human workers, this episode reveals the systemic changes already happening beneath the surface. Nick also pulls back the curtain on his Apprentice experience, sharing the psychological manipulation tactics used by reality TV producers, and offers his "barbell strategy" for legal spending: automate the basics, hire only the absolute best commercial lawyers for complex deals.> "The social contract is broken now. The people at the bottom no longer get this shot of being the lazy fat ones on the top."The $200K Legal Template RevelationNick exposes how law firms charge enterprise rates for junior work using standardized templates from Practical Law and LexisNexis. While partners enjoy social events, juniors work 80+ hour weeks filling out templates that clients could complete themselves.> "90% of the bill is actually operational stuff that's not a really smart lawyer. It's someone much more junior, and they're getting charged at $500-1000/hour."This broken economic model—where partners capture massive margins while juniors do the grunt work—is about to collapse as AI eliminates the need for junior lawyers entirely.Why Most Founders Are Overpaying for LegalThe failing pattern Nick sees repeatedly: founders pay premium rates for template work that could be automated. His solution challenges conventional legal spending:> "Go tippy top or prompt. That's it. Barbell strategy."His argument: either automate the basic work or hire only the absolute best commercial lawyers who can negotiate deal terms worth hundreds of thousands. Skip everything in between.The Reality TV Psychological Manipulation PlaybookNick pulls back the curtain on The Apprentice's systematic psychological warfare tactics:> "They put ideas into your mind. They tell you 'Did you notice Nick was giving you an evil look? He thinks you're rubbish.'"The show uses sleep deprivation, 24/7 surveillance, isolation from family, and planted conflicts to break down contestants mentally. Despite the manipulation, Nick would do it again for the business exposure.The AI Unemployment Crisis Politicians Can't SeeNick reveals the hidden crisis already happening in the legal profession:> "Hundreds of applicants from great universities. They haven't got jobs."When GitLaw posts lawyer positions, they're overwhelmed with desperate qualified candidates. But politicians don't see the displacement because "we're all in a bubble."The Coming Tax Revenue DisasterThe conversation takes a speculative turn into the fiscal crisis coming from AI displacement. When AI agents replace human workers, states lose massive tax revenue but gain unemployment costs with no funding for safety nets.> "Europe has kind of got a model for that. You can tax the agents really high to pay for everyone on universal basic income."Europe's existing social safety net infrastructure gives them a massive advantage in the AI transition compared to America's lack of UBI systems.Companies Mentioned GitLawPractical LawLexisNexisHarvey AILawhiveLegoraGranolaElevenLabsSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Madhavan Ramanujam, a pricing expert and author, challenges conventional AI monetization strategies. He highlights that many founders underestimate their product's value, often leaving huge sums on the table. By sharing a case where a simple pricing option led to a 10X increase, he illustrates the importance of value over cost. Madhavan urges companies to rethink their pricing frameworks, avoid common pitfalls, and focus on profitable growth. His insights reveal how the right pricing strategy can be the true competitive advantage in the evolving AI landscape.

John Sabino, CEO of LivePerson and former Army Ranger, discusses his bold decision to pivot away from creating a traditional LLM towards their innovative Bring Your Own LLM (BYOLLM) strategy. He highlights why 95% of AI pilots fail, attributing this to overlooking essential orchestration and customer journey mapping. John emphasizes a human+AI approach, advocating for strategic augmentation instead of layoffs. His insights on targeting enterprise customers and realigning investor expectations reveal the complexities of leading a tech turnaround.

The Enterprise AI Reckoning Has ArrivedThe AI spending party is over. Ethan reveals that public companies went on unprecedented buying sprees in 2024, with procurement teams purchasing up to 500 different AI tools in a single year. Now comes the hangover - these same companies have instituted total bans on new AI vendors and are mandating 50% cuts before they'll even take another meeting."We bought 500 pieces of AI software in the past year. We have a total ban on new vendors whatsoever. We have to cut at least 250 of it before we even have conversations ever again."The dirty secret? Nobody's actually using these tools. Ethan estimates 50% of enterprise AI initiatives have already failed, but companies won't admit it publicly. Teams churned the tools internally, but the invoices keep coming because admitting failure isn't an option when boards demanded "buy one of each" strategies."Nobody on our team used it. So that's like 50% of our AI initiatives down the drain. You never want to admit that your AI initiatives have failed."Information Blindness Creates Billion-Dollar MoatsHere's the shocking truth about AI adoption: most users have no idea what they're actually using. Ethan drops a bombshell - while everyone knows ChatGPT, less than 10% of users understand that OpenAI powers it. This information blindness creates massive opportunities for vertical AI products."I think people underestimate how many companies or how many people there are, who if they use Harvey for lawyers, you might never find out what ChatGPT is. Less than 10% of them know what OpenAI is."The implication is profound: if you're first to a niche with an AI solution, you might own that market for 4-5 years. Users develop "infinite loyalty" to their first AI tool because they never discover alternatives exist. It's like Nokia still having devoted users despite the iPhone - once you capture a market segment, information penetration is so weak that switching barely happens.Data Science: The Infinite Arms RaceUnlike fixed workloads like accounting, data science has infinite demand because it's fundamentally competitive. Ethan uses a brilliant example: when Blackstone analyzes housing prices weekly by city, Cerberus counters by going daily by zip code. Then Blackstone responds with hourly analysis by square footage."If Blackstone analyzes housing prices per city per week, then Cerberus will want to analyze it per zip code per day. Then Blackstone's gonna want to do it per single family unit size square footage per hour."This creates exponential demand growth - give trading firms 10x faster analysis, and they'll make 100x more trades because they can now pursue opportunities previously too small to bother with. TextQL's entire business model depends on this dynamic: as they reduce costs, volume explodes exponentially. It's why they're usage-based while competitors offering flat pricing are getting crushed by token costs.Don't Innovate UI, Dominate DistributionEvery AI startup makes the same mistake: trying to innovate on user interface. Ethan's blunt assessment? Every single UX innovation TextQL attempted was "a horrible idea." The winning formula is surprisingly simple: copy ChatGPT's interface exactly (chat on left, workspace on right), then put all innovation into branding and distribution."Almost every single innovation we have ever tried to do with this company on UX has been a horrible idea. We always go back to the base. Your branding is entirely unrelated to your product."The painful truth for engineers: the product doesn't matter, positioning does. Say you're "the AI agent for laundromats," give it a hard hat, and hammer that message repeatedly. The opportunity isn't in better AI - it's in reaching the people who don't use AI yet and saying "I built this for you." Marketing matters 10x more than the product in today's AI landscape.OpenAI's $350 Billion Ad Platform PlayOpenAI's aggressive pricing on GPT-5 isn't about winning the API war - it's about building the world's most powerful commerce platform. Ethan paints a dystopian but likely future: you tell ChatGPT you're sad, and it recommends therapist Frederick Carlson, books the appointment, charges your credit card, and informs you it's out-of-network for $500."ChatGPT says, 'Well, you should consider talking to a licensed therapist, Mr. Frederick Carlson.' It's like, 'You want me to book a meeting for you right now? I've used your credit card to pay for this therapy.'"Every early OpenAI and Anthropic demo featured "order me a pizza" as the use case. When ChatGPT becomes the layer between you and commerce, DoorDash and Uber Eats will pay massive fees to be the "preferred carrier." With potentially a billion users, OpenAI is sacrificing API profits to build something far more valuable: the transaction layer for AI-mediated commerce. As Ethan notes, ads are a $350 billion profit business, and "people just like being sold to."The Trillion-Dollar Coin Flip StrategyWhile everyone else fights over $10 billion exits, Ethan has a different philosophy: he's only interested in trillion-dollar opportunities. His target? AWS. His strategy? Be willing to flip coins at 51% odds repeatedly, as long as the expected value is massive."I'm basically willing to flip. I'm kind of more like SBF. I'm pretty happy to flip the coin with 51% chance over and over again, as long as I have high EV. I'm only interested in trillion-dollar market opportunities."TextQL follows the Bezos doctrine: "your margin is my opportunity." They'll trade 1% of profit margin for 2% growth every time, because volume creates the ability to hire the best engineers, optimize infrastructure, and ultimately offer better prices than any competitor. It's the same playbook AWS used to become a trillion-dollar business - sacrifice margins early, dominate on volume, then own the entire market."I don't want to build a $10 billion business. That seems incredibly boring to me. I just want to go after AWS."The AI industry is experiencing a massive correction. Enterprises are drowning in unused tools, OpenAI is building an ad empire disguised as a chatbot, and the real winners will be those who understand that in AI, distribution beats innovation, volume beats margins, and the first mover in a niche might own it forever. As Ethan says - "It's not the model, it's the marketing."Companies MentionedOpenAIAnthropic (Claude)Google (Gemini)Amazon AWSMicrosoftMetaNetflixSpotifyCursorWindsurf (acquired/sold)ReplitLovableBoltClaude CodeHarveyTextQLDatabricksSnowflakeCognizantBlackstoneCerberusGoldman SachsPWCNokiaDoorDashUber EatsWalmartSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Rob Litterst, founder of PricingSaaS and writer of the insightful newsletter Good Better Best, dives into the rocky terrain of SaaS pricing. He reveals that traditional seat-based models are becoming obsolete as the industry grapples with AI. Rob stresses the urgency of innovative pricing strategies to avoid irrelevance. Excitingly, he shares Intercom's bold move to price according to growth via AI agents rather than conventional metrics. The conversation also touches on the need for creativity in marketing during these transformational times.

You know something fundamental is shifting in tech when the drama between startups and their AI providers becomes more entertaining than reality television. That's exactly where we found ourselves in this conversation with Foundation Capital partners Ashu Garg and Jaya Gupta."This is better than Love Island. I love this shit. Like the gossip and the intricacies of like the people itself. It's amazing."Manny wasn't wrong. The Cursor pricing saga - where a startup's infrastructure provider started building a competing product, leading to poached PMs, revoked discounts, and user revolts - is just one symptom of a much larger transformation happening in software.The Death of SaaS (As We Know It)The conversation started with what might be the most sobering statistic for anyone running a SaaS company today. According to Ashu, the middle market is getting absolutely crushed:"Mid-sized SaaS companies are struggling. Nine out of 10 are seeing some churn, but the churn isn't dramatic yet. They're seeing employee attrition. They're fighting a war of feature by feature. They're trying to add AI pixie dust here and there. But net-net, they're all struggling."The companies he's talking about - those between $100M and $1B in revenue - find themselves in an impossible position. They're too small to acquire their way out of trouble like the giants can, but too big and established to pivot quickly like startups.Ashu pointed to Outreach as a prime example: "Incredible company for a decade. Look at the numbers today. It's flat, maybe marginally declining."Meanwhile, tiny AI-native startups are "growing like crazy" from the bottom up. The bit hasn't flipped yet, but Ashu thinks we're not far from a tipping point where customers abandon their incumbent platforms en masse.The $20 Million First CustomerPerhaps nothing illustrates the speed of this transformation better than Ashu's revelation about deal sizes in the AI era:"I funded a company earlier this year. Their first deal, which hasn't been signed yet - knock on wood - but the first customer is likely to give them a $20 million plus TCV deal. When's the last time you saw a seed stage company get a first customer at $20 million plus?"This isn't normal SaaS growth. This is a company jumping from seed stage to Series E valuations in a single deal. The company in question? They're migrating legacy SAP and Oracle code using AI. When you're solving billion-dollar problems with AI, apparently the old rules about gradual revenue growth simply don't apply.Why Experience Became a LiabilityOne of the most controversial takes came from Jaya, who argued that in AI, youth beats experience:"AI is new for everyone. Like, if anyone can predict what's happening in six months, I would call that bullshit. No one knows what's happening. You are seeing in this market a ton of younger founders even outpace second time, third time founders that have built unicorn companies."The logic is simple but profound: everyone started learning AI at roughly the same time. But younger founders have less to unlearn, move faster, and are using AI itself to build their companies more efficiently. As Jaya put it, "Knowledge has been quickly democratized."This might explain why Foundation Capital has such an unusual approach to evaluating companies..."If You Have Revenue, Don't Call Me"In perhaps the most counterintuitive investment philosophy you'll hear, Ashu actively avoids companies with revenue:"Even though we don't really invest in companies with revenues, in fact, I always tell people, if you have revenues, don't call me. I'd rather not deal with messy revenues. I want to deal with big ideas."This isn't just contrarianism. Ashu argues that early revenue often constrains vision and forces founders to serve existing customers rather than reimagining entire categories. Even without revenue, he looks for other forms of traction: Who are the early customers you're talking to? Which engineers are you recruiting? If you're building in sales tech and haven't talked to Manny, "I'm not funding you."The 500 Agent FutureThe partners saved their boldest prediction for last. Forget building another point solution or feature company. The future belongs to companies that think bigger:"The world of AI apps and AI agents is about 500 agents from one company replacing 500 feature companies. You've got to think broad, you've got to think big, and you've got to execute like crazy to see which agent works, because very often one or two agents doesn't solve anything for a customer. They need enough of these agents to really move the meter."This runs counter to everything VCs have preached about focus for the last decade. But in Ashu's view, the narrow AI startup is already dead. Customers don't want to manage hundreds of point solutions anymore - they want comprehensive agent armies that actually move the needle.The Plot Twists Keep ComingBeyond these major themes, the conversation was peppered with surprising predictions and hot takes:On the AI giants: Despite their massive valuations and growth, Ashu is "very skeptical on both OpenAI and Anthropic." He believes that "when the dust settles, it's not clear that the winners in that category will be either of the two companies."On pricing models: While everyone talks about outcome-based pricing, Jaya thinks we'll see an evolution through usage-based and workflow-based models first. True outcome-based pricing remains elusive because, as she notes, "the outcome is actually just a function of the customer's product as well, not just your software."On commitment issues: Both partners openly admitted to having "commitment issues" when it comes to investing, preferring to "date" founders for four to five months while gathering what Jaya calls "observability data" on how they think and learn.What This Means for FoundersIf you're building in AI right now, the message is clear but daunting. The playbook that worked for SaaS won't work here. As Ashu put it:"A lot of the lessons that you and I learned over the last few decades of software apply, but a lot more don't. Knowing when to break the mold and reinvent and reimagine how you do things, I think is a big part of winning in the AI space today."For Manny, who built Outreach into a unicorn, this resonates deeply. He's now tackling the problem of monetization and margin management for AI agents - the very issue that was "the bane of his existence" at Outreach. Sometimes you do "irrational things at irrational times," as he puts it.But in a world where the drama is better than Love Island and first customers write $20 million checks, maybe irrational is exactly what we need.Companies & Products MentionedFoundation CapitalOpenAIAnthropicCursorWindsurfClaude (and Claude Code)11XHarveyScribeLovableTenorFulcrumOutreachSalesloftDatabricksSalesforceOracleSAPExcelWixMcKinseySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.