Shows
Get Paid with Manny MedinaWe had 90 days to ship or shut down | Eric Simons (Bolt)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...
2025-10-3154 min
Get Paid with Manny MedinaNetSuite is where ERPs go to die. We're building the escape hatch | Jonathan Sanders (Light)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...
2025-10-2446 min
Get Paid with Manny MedinaBuilding Paid: $31M Raised on Confidence, Not Fear (Manny Medina, Raj Dosanjh)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...
2025-10-171h 01
Get Paid with Manny Medina"You're Not Buying Software, You're Hiring a $1K Employee" (Amjad Masad, Replit)We invited Amjad Masad, CEO and founder of Replit, fresh off raising $250M at a $3B valuation and hitting $150M ARR, to share why point solution model is dying, how his own HR person built their org chart software in 3 days (killing the need for expensive vendors), and why consumers still don't understand they're hiring employees, not buying software.Amjad and Manny explore the resurgence of the small entrepreneur enabled by AI agents. From the YouTuber doing Upwork arbitrage with Agent 3 (45 minutes, $25, full app delivered) to the VC CFO building software for other VC CFOs, this episode...
2025-10-1046 min
Get Paid with Manny MedinaThe $200K legal bills that made me automate law firms (Nick Holhzherr, GitLaw)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...
2025-10-0359 min
Get Paid with Manny MedinaPrice Before Product: The AI Monetization Playbook (Madhavan Ramanujam, 49Palms)Madhavan Ramanujam stepped into the AI pricing conversation with a contrarian view: everyone is doing it wrong. As author of "Monetizing Innovation" and founding partner of 49 Palms Ventures, he's advised 250+ companies on pricing strategy. Now he's seeing founders leave millions on the table by using outdated SaaS playbooks for AI products.> "Your moat is monetization and GTM. Can you get products in the hands of many people? Can you make it stick? And will they pay for the value?"His message is clear: the two-year coding head start you're banking on is worthless. In the...
2025-09-2658 min
Get Paid with Manny Medina“VCs wanted us to build an LLM. We said no” | John Sabino (LivePerson)John Sabino stepped into LivePerson as CEO facing a perfect storm: financial distress, harsh investor criticism, and a company that had "lost its way" trying to build the world's best LLM. Within weeks, major investors were telling him his strategy wouldn't work and that the company wasn't mentioned in critical industry reports."You have to have the wherewithal and the courage to say, I'm not doing that. I'm going to try this first."His response was to refocus on LivePerson's core strength - 30 years of orchestration expertise - while pioneering what became an industry standard...
2025-09-1950 min
Get Paid with Manny MedinaChatGPT is going to sell you therapy | Ethan Ding (TextQL)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...
2025-09-1241 min
Get Paid with Manny MedinaSaaS Revenue Bloodbath Is Coming | Rob Litterst (PricingSaaS)Rob Litterst is on a pricing island, and it's about to get very crowded. After watching traditional SaaS companies fumble with AI pricing, he's going full-time on PricingSaaS to shepherd the entire industry through what he calls "a really interesting rat's nest of questions." The biggest confusion? Everyone thinks agent pricing means outcome pricing. Spoiler: it doesn't.The Seat-Based Apocalypse Is HereRob's take on the death of traditional SaaS expansion is brutal and honest: "Seats are not an expansion lever anymore."The math is simple and terrifying for legacy SaaS. Startups now...
2025-09-0538 min
Get Paid with Manny MedinaAI is better than Love Island | Ashu Garg and Jaya Gupta (Foundation Capital)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...
2025-08-2942 min
Get Paid with Manny MedinaWill Bots Buy From Bots at $10K? | Maruthi Medisetty (Blue AI)Subscribe on https://podcast.paid.aiMaruthi Medisetty thinks your sales enablement team is wasting 50 hours a week, and he's built AI agents to prove it. After watching reps practice with AI for 60-75 minutes straight (when they won't even spend 30 with their managers), he's got some contrarian takes on why humans will always close the big deals, how to charge 10% of the value you deliver, and why companies pay McKinsey millions just to have someone to blame.The 50-Hour Week Nobody Talks AboutFive enablement people reviewing 10 calls each per week equals 50...
2025-08-2242 min
Get Paid with Manny MedinaInfinite markets: We don't optimize for COGS | Christopher O’Donnell (Day.ai)Show page: https://go.paid.ai/podcast-s2e14Christopher O'Donnell just built what might be the most technically brutal CRM ever attempted. After two years and two million lines of code connecting Gmail APIs, Google Calendar, and meeting transcripts into a preprocessing engine that actually works, he's got some spicy takes on AI economics, the coding tool wars, and why the universe might be conspiring in your favor.The "Total Piece of Cake" Preprocessing HellChristopher's favorite response when competitors think they can copy Day.ai's approach: "Good luck. Have fun. I'm here...
2025-08-1540 min
Get Paid with Manny MedinaThe Death of Traditional Startup Scaling | Amos Bar-Joseph (Swan)The venture capital model is dying, and Amos Bar-Joseph has the data to prove it. After selling two previous startups, he's now building Swan AI with an audacious goal: $30 million in revenue with just three people by 2025. The kicker? Over 50 VCs have approached him, not because he needs money, but because they're desperate to understand how autonomous businesses will reshape their entire industry.The Three-Function Business ArchitectureTraditional startups have bloated org charts with misaligned incentives. Amos stripped it down to three core functions:"An autonomous business don't have 10 different roles under the...
2025-08-0847 min
Get Paid with Manny MedinaGetting Customers to Pay Before You Code | Pukar Hamal (SecurityPal AI)When enterprise deals die at the finish line because of a 200-page security questionnaire, you know there's a billion-dollar problem hiding in plain sight. SecurityPal founder Pukar Hamal turned that pain into a service-as-software business that hit $2 million in revenue before building any actual software.The Pain That Creates Billion-Dollar MarketsPicture this: you're about to close the deal that changes your company's trajectory. The champagne is ready. Then boom - instead of DocuSign, you get 200 pages of security questionnaires:"We were like ready to pop champagne bottles. And so, you know, we...
2025-08-0134 min
Get Paid with Manny MedinaAI Agents Will Eat Everything | Jack Altman (Alt Capital)Is venture capital broken, or are we just doing it wrong? Jack Altman brings a rare founder-turned-VC perspective after scaling Lattice to $3 billion and stepping back as CEO while on top. Now managing Alt Capital with investments in Figma, Rippling, and Flexport, Jack delivers brutal honesty about what's really happening in startup investing.The Dating Analogy That Changes Everything Jack compares investor-founder relationships to dating - and the analogy is disturbingly accurate:"I think it is a little bit like dating. Even your cherished execs come and go faster than preferred board members."...
2025-07-2545 min
Get Paid with Manny MedinaWhy AI Won't Kill Salesforce | Aaron Levie (Box)Are we in the iPhone moment of AI, or are we still building janky mobile apps? Box CEO Aaron Levie brings 15+ years of enterprise software experience to break down the biggest questions facing SaaS companies today. From pricing models to regulatory risks, this conversation goes deep on what's actually happening behind the AI hype.The Great AI Pricing ExperimentEvery software company is scrambling to figure out how to monetize AI agents. Do you charge by seats, tokens, outcomes, or some hybrid model? Levie reveals the chaos happening in boardrooms:"There's no board...
2025-07-1848 min
Get Paid with Manny MedinaThe BPO Boss: Humans Are Going Premium | Bryce Maddock (TaskUs)We sit down with Bryce Maddock, CEO of TaskUs (60,000+ employees, $1B+ revenue), who delivers the most honest take you'll hear about AI's impact on the service industry. As one of the world's largest BPOs navigating the AI transition, Bryce pulls no punches about automation claims, job displacement, and what's really happening behind the headlines.Bryce exposes the disconnect between public AI claims and private reality:"I see metrics where it's like, hey, We've automated 60, 70, 80% of our customer support. And I'm in the background being like, well, we still have the same number of humans. So...
2025-07-1145 min
Get Paid with Manny Medina"You almost have to erase everything you learned in the 2010s" | Kellan Carter (FUSE)We sit down with Kellan Carter, General Partner at FUSE, where he pulled back the curtain on what's really happening in AI investing, revealing why traditional SaaS metrics are misleading and how a new generation of founders is building completely different businesses.The Revenue Quality Crisis Nobody Talks About"For the last year, this came up in every single board meeting: how do I evolve my pricing?". Yes, founders chase vanity metrics, but the underlying unit economics are falling apart. Companies love their biggest customers but are losing money on them - a classic case o...
2025-07-0444 min
Get Paid with Manny MedinaWill AI Agents Kill Customer Service Jobs? | Alexander Matthey (Parloa)We sit with CTO and co-founder of Parloa, Alexander Matthey, where he's building the AI agents that promise to revolutionize how businesses interact with their customers. Unlike the doomsday prophets predicting mass unemployment, Matthey paints a more nuanced picture of what's coming.In our latest podcast episode, we dive deep into the transformation of customer service, the survival strategies for BPOs, and why building the "Ferrari" of AI platforms matters more than ever.The Speed Game Has Changed ForeverStarting a company in AI isn't like starting one in fintech or beauty tech...
2025-06-2735 min
Get Paid with Manny MedinaHard is a moat | Max Altschuler (GTMFund)We hosted Max Altschuler, founder of Sales Hacker and GTMfund in our studio to talk about how AI is fundamentally reshaping go-to-market strategies and why he thinks most GTM software companies are in trouble.After a near-death experience, Max made a radical life change - selling his dream home in Scottsdale and going "asset light" to prioritize nature and lifestyle over traditional success metrics. As he explains:"I really am just the happiest person when I'm in nature. I'm a better father, partner, friend, and I'm better at my job. Like I need to be...
2025-06-2046 min
Get Paid with Manny MedinaWill AI Kill the SDR or Just Make Them Smarter? | Adam Schoenfeld (Keyplay)We sat down with Adam Schoenfeld, co-founder and CEO of Keyplay, to explore how AI is transforming account selection and go-to-market strategies. Adam has taken his years of experience building Simply Measured and turned it into solving one of B2B's most persistent problems: figuring out which companies to actually sell to.While everyone else is trying to use AI to spam more people, Adam sees a different future. "The biggest trap that a lot of people are falling into is they're seeing this as kind of a volume game. The best people are gonna use it...
2025-06-1331 min
Get Paid with Manny MedinaAI is Making Sales Teams MORE Important, Not Less | Sahil Mansuri (Bravado)In this eye-opening episode of Get Paid, I spoke with Sahil Mansuri, founder and CEO of Bravado, about how AI is dramatically reshaping the landscape of sales and recruiting but not in the way most people think.While many SaaS companies are seeing their business models threatened by AI's ability to automate human work, Bravado is experiencing the opposite effect. As Sahil explains, "Because we were in recruiting and what we did was more services heavy than software heavy, venture capitalists used to be less excited about our business." However, the rise of AI has transformed Bravado's...
2025-06-0640 min
Get Paid with Manny Medina$15 Trillion Mortgage Industry Being Disrupted By AI | Jim Cutillo (Alpha7x)In the latest episode of Get Paid, I had the pleasure of speaking with Jim Cutillo, a 30-year veteran of the mortgage industry and founder of Alpha7x. His company is transforming mortgage lending with AI agents that cut costs and streamline the entire process.If you've ever bought a home, you know the mortgage process can be a nightmare. What you might not know is that it's actually getting worse, not better.Jim shared a startling revelation: despite decades of technological advancements, the mortgage industry has become less efficient. "The cost today is at...
2025-05-3030 min
Get Paid with Manny MedinaBuilding a $1B Company with Only 100 Employees | Elias Torres (Agency)Elias Torres, founder of Agency and formerly Drift (which sold for $1.2B), joins us to explain why he considers that exit his "biggest failure" and how he's reimagining business building in the age of AI with his new company, Agency.The Billion-Dollar Failure That Wasn'tDespite selling Drift for $1.2 billion, Elias surprisingly calls it his "biggest failure." Why? Because his ambition was to build a $30 billion company that would go public:"My mind for Drift was we were gonna build a $30 billion company. We were gonna take it IPO... And...
2025-05-2335 min
Get Paid with Manny MedinaIs Controversy the Secret to Winning in AI Sales? | Jaspar Carmichael-Jack (Artisan)Jaspar Carmichael-Jack, Artisan's CEO, revealed his controversial strategy: deprioritizing everything except their main AI outbound agent, Ava.Why focus solely on outbound when everyone's building multi-product AI companies?Jaspar's explanation cuts through the typical startup playbook:"We have a lot of product service area to cover that we haven't covered yet. And we've seen with every incremental release we've done so far, customer outcomes just explode every single time”."I feel like we have to earn the right to [build multiple products] before we can just go multi-product im...
2025-05-1431 min
Get Paid with Manny MedinaAgent Talk #11 - Nick Mehta (Gainsight) - Most SaaS companies will die in the AI revolutionNick Mehta, Gainsight’s CEO, didn't mince words in our latest conversation. He says the entire enterprise software model we've built over the past 20 years is fundamentally broken.What doesn’t work about SaaS anymore?The model that made Salesforce, Workday, and countless others into tech giants? According to Nick, it doesn't work anymore:"We bring in data from disparate systems, we use some kind of ETL to combine it, we have rules that say if this, then that, we have workflow for humans to take action, and then reports for managers. I argu...
2025-04-3037 min
Get Paid with Manny MedinaAgent Talk #10 - Anshul Gupta (Actively) - Real Relevance, Not Lazy AI PersonalizationIn our latest episode, we talk with Anshul Gupta, who recently raised $22.5M from Bain Capital and First Round Capital for Actively.Our favorite takeaways:* Personalization at scale is actually "laziness at scale": "The amount of emails I got saying 'Anshul, congrats on your recent funding round' followed by a totally unrelated value proposition... if you're looking at thin logic like 'someone raised funding, throw them in a sequence,' that's not working anymore."* Top performers do less, not more: "When you sit down with the best reps, they're not the ones doing...
2025-04-1119 min
Get Paid with Manny MedinaAgent Talk #9 - Doreen Huber (EQTV) -We're Rethinking SaaSIn a candid conversation at Paid’s launch party, EQT Ventures investor Doreen Huber shared her razor-sharp perspective on what’s working in AI agent investing, why traditional SaaS is losing ground, and what founders need to bring to the table to secure funding in this new era.Our favorite takeaways:* SaaS is no longer the focus to the B2B Software team at EQT Ventures:"My team is not investing in traditional SaaS anymore. Our strategy is to go for agentic, AI-native companies, and we tend to disqualify what doesn’t fit that bucket."...
2025-04-0331 min
Get Paid with Manny MedinaAgent Talk #8: Amos Bar-Joseph (Swan) - The 10M ARR per employee dream with AIIn our recent conversation with Amos Bar-Joseph, CEO and co-founder of Swan AI, he shared his radical vision for the future of business: autonomous companies achieving $10M ARR per employee through strategic AI implementation. Beyond the typical AI hype, Amos details a practical roadmap for companies looking to scale with minimal headcount.Here are the key insights from our discussion:The autonomous business revolution* The next 5 years belong to SMBs: "We believe that the next five years are the year of the SMB, the year of the small business, small lean teams that...
2025-04-0126 minGet Paid with Manny MedinaAgent Talk #7: Pat Grady (Sequoia) - What actually works in AI startupsIn a recent deep dive with Sequoia Capital partner Pat Grady, he shared surprising insights about what separates winning AI companies from the rest, and challenged conventional wisdom about AI moats, pricing models, and what investors truly value.Our favorite takeaways:* Building AI companies is just building a company. It’s 95% the same and people problems still dominate* Trust is the critical design pattern most AI companies miss. Users need to see how you arrive at your results* Most AI products achieve 80% functionality quickly, but the final 20% takes 5-10x longer an...
2025-03-2633 minGet Paid with Manny MedinaAgent Talk #6: Wade Foster (Zapier) - Why Zapier Sacrificed Millions to Earn MillionsWade Foster, co-founder and CEO of Zapier, shares how they completely revamped their pricing model - and actually REDUCED revenue in the short term - to drive explosive long-term growth.Since launching in 2011, Zapier has grown to help millions connect their apps without code, reaching a valuation over $5B with minimal VC funding. Their recent pricing change offers fascinating insights for SaaS founders.Key takeaways:* Zapier eliminated their dual-metric pricing (Zaps + Tasks) to simplify the customer experience* They made unlimited Zaps available on all plans - removing a major friction point
2025-03-1330 minGet Paid with Manny MedinaAgent Talk #5: Mickey Haslavsky (Enso) - SaaS is Dead, Long Live $49 AI AgentsManny hosts Mickey Haslavsky of Enso, who's flipping the script on AI agents in the most refreshing way.Mickey says their mission at Enso is to reduce the prices of services, just in general, for small businesses.While lots of AI companies chase enterprise dollars or build complex multi-agent systems, Mickey's team is printing money with a simple contrarian approach: deliver "good enough" AI agents to small businesses at a flat $49/month.Some key insights from our conversation:* "SaaS is pretty much dead... some of the agents that we're building, you...
2025-03-0528 minGet Paid with Manny MedinaAgent Talk #4: Rob Litterst (PricingSaaS) - SaaS Pricing is Dying as AI Agents Are Eating The WorldRob Litterst (HubSpot exec & SaaS pricing guru) just dropped some mind-blowing insights about how AI is completely disrupting traditional software business models. Whether you're building AI products or just trying to stay ahead of the curve, this episode is packed with spicy takes on where the industry is headed.Three explosive themes that'll blow your mind:* The Death of Per-Seat Pricing: The old way of charging per user is getting absolutely demolished by AI agents. Rob breaks down how companies are being forced to evolve or die as AI native startups come gunning for their...
2025-02-2627 minGet Paid with Manny MedinaAgent Talk #3: Shawn Harris (Coworked) - How Coworked Solved The Impossible"35% of projects fail, and the numbers haven't budged in 20 years."That's what kept Shawn up at night before founding Coworked. After two decades in project management, he'd seen every methodology, tool, and framework come and go - yet the fundamental problems remained stubbornly unchanged.Shawn is building an AI project manager that could transform how work gets done. But not by replacing humans - by unleashing them.Harmony, Coworked's AI agent is rewriting the rules of project management. While most AI companies are focused on chatbots and automation, Coworked is tackling something far...
2025-02-1323 minGet Paid with Manny MedinaAgent Talk #2: Kelly Waldher (Zendesk) - How Zendesk Disrupted ItselfZendesk's journey isn't just another AI adoption story - it's a masterclass in how even enterprise companies can reinvent themselves in the age of AI.While others rushed to add AI features, Zendesk took the bold step of completely reimagining their business model.What's fascinating is how they navigated the classic innovator's dilemma: "It's one thing to understand it, it's another thing to be in it and live it," as Kelly puts it.They didn't just add AI - they fundamentally changed how they deliver and capture value.Think about their...
2025-02-0524 minGet Paid with Manny MedinaAgent Talk #1: Victor Riparbelli (Synthesia) - Beyond the Avatar: Building a $1B AI Video PlatformSynthesia's success wasn't about chasing the latest AI trends, but about solving real business problems with a relentless focus on enterprise-grade features and workflows.In this first episode, Manny talks to Victor Riparbelli, founder and CEO of Synthesia that raised $180M in Series D.What's fascinating is how Synthesia navigated the classic enterprise software challenge: balancing the "wow factor" with sustainable business value.While most AI companies get caught in the "sugar high" of viral demos, which is why we’re seeing massive churn problems right now. Synthesia on the other hand focused on...
2025-01-2835 min