Podcast
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Conversations with founders and operators at businesses between 1 and 100 million
23episodes
Episodes
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E59: The New Normal with Olivia Kory and Joe Wyer from Haus
2w ago00:44:46Tap to summarizeThis conversation started with a simple question: are you more productive with kids or without them?From there, we got into the operating questions AI is forcing every company to confront. When should you delegate to a person versus an agent? What happens when execution becomes cheap? How much more valuable does judgment become? And how do leaders raise the performance bar while giving their teams room to adapt?Olivia and Joe from Haus also unpack the challenge at the center of their business: giving marketers a more accurate source of truth, even when that truth changes how a company sees years of decisions. We talk about top-down AI adoption, agentic marketing systems, internal tools like Docmaster, teaching teams to work with AI, and why the gap between great and average operators is widening so quickly.A wide-ranging conversation about parenting, focus, leverage, delegation, AI-native teams, and what it takes to operate through a period of constant change.
Transcribe →E59: The New Normal with Olivia Kory and Joe Wyer
4w ago00:51:34Tap to summarizeIn this episode of the SaaS Operators Podcast, the Haus crew, Olivia and Joe, join Rishabh and Jeremiah for a wide-ranging conversation.It opens with a lighthearted riff on the explosion of "Chief [Something] Officer" titles before shifting into something every founder wrestles with: balancing total immersion in the mission with being present for family.Olivia reflects on missing the deep-flow days before kids, while Rishabh offers a counterpoint, that divided attention may actually be where the best ideas emerge.The conversation then turns to leverage and delegation in the age of agents.Rishabh notes that people increasingly build an agent rather than train a teammate, sparking a discussion about judgment becoming the scarce skill as execution gets cheaper.Joe and Olivia also share how Haus navigates this with customers, where convincing marketing teams to trust a new, sometimes unflattering, source of truth is often the hardest part, and why that shift usually has to come from the top.The episode wraps on internal operations: how do you coach a team through a moment when the performance bar keeps rising?Joe's approach, letting AI take the first crack at everything and teaching judgment relentlessly, stands out as a grounded take.Rishabh's note that the gap between A and B players has grown from 30% to roughly 4x is a line worth sitting with.
Transcribe →E58: Building AI Employees
Jun 2900:59:20Tap to summarizeIn this episode of the SaaS Operators Podcast, Jack, Jeremiah and Rishabh talk to Burak Karakan about how he's building an AI data team companies can use.They cover why his company started with a data integration layer before adding agents, how that helps tackle messy, multi-source business questions, and whether the company plans to move from time to insight toward taking action on a business's behalf.The conversation moves into open source as a trust-building strategy, Burak's reluctance to lean into services, and the SMB versus enterprise debate, with Rishabh and Jeremiah weighing in on the opportunity sitting in enterprise.Burak explains why he'd rather build like Stripe than operate like McKinsey, even if it costs him some upside.The episode opens with a detour into baby monitors and smart diapers, since everyone but Burak has just become a parent, and closes with Rishabh's "does it matter or not" framework for cutting through the noise and giving honest feedback.
Transcribe →E57: The $100M SaaS Company Nobody Wants to Buy
Jun 2600:43:29Tap to summarizeIn this episode of the SaaS Operators Podcast, Rishabh, Jeremiah, and Jack tackle an uncomfortable question: what happens to a traditional, well-run software business in the AI era?If you're running a $200-800M company with solid margins and steady growth, who's actually buying you? They dig into EBITDA multiples, why PE's old playbook looks shakier after write-offs like Medallia, and whether incumbents can out-execute the disruption by changing fast enough.They also get tactical, talking about how Claude is rewriting what it means to build a landing page or website.Jack walks through recreating a high-converting Gymshark-style page in minutes inside Shopify, fully customizable, no developer needed.They talk about what that means for tools like Replo, and why incumbents like Wix trade at sub-1x revenue multiples despite record revenue and their own AI products.They close on the people side: building AI-first teams and compensation structures, drawing on Coinbase's comments about one-person teams running fleets of agents.Rishabh shares how FERMÀT is restructuring comp around individual impact, and the group discusses the gap between San Francisco and everywhere else when it comes to AI adoption urgency.
Transcribe →E56: Building AI from Bangalore with Yash Chavan
Jun 1600:55:09Tap to summarizeIn this episode of the SaaS Operators Podcast, Rishabh Jain is fresh off three 20 hour days, a 20-minute layover in Denver, and four hours of sleep. Fueled by coffee and diet coke with zero complaints.The conversation starts with the AI adoption gap. Rishabh came back from Cincinnati with a clear read, the average person there is about two years behind SF, not nine months. Jeremiah added that the early adopter bubble is small, and the people outside it are just now using ChatGPT to rewrite website copy. Yash shares what’s happening in the India AI space. Bangalore is moving, Anthropic and Cursor both have offices there, and a generation of graduates who want startups over Infosys are driving it.Jack raises the first mover question. If anyone can build what used to take six months in an afternoon, what's the actual moat? Rishabh's answer: it depends on what the business is optimizing for. VC-backed, you land grab. Cash flow business, maybe speed matters less. Shipping velocity and stability get unpacked too, and Rishabh draws a line. Agentic workflow software doesn't have the same availability requirement as transactional software. Claude goes down for two hours while an agent runs a task, it doesn't matter.Rishabh shares how he built a bot trained on how he thinks, gave it a public Slack channel, and let the whole company use it. People ask better questions to the bot than they'd ever ask him. CEO time goes from scarce to abundant.The episode closes on when to get out of sales calls. Yash's framing is the cleanest: stay in until the rate of learning drops. Once you stop getting new insights, hand it off.
Transcribe →E55: AI Native Teams with Jacob Posel from HQ
Jun 100:45:00Tap to summarizeIn this episode of the SaaS Operators Podcast, Jacob Posel joins Jeremiah, Jack, and Rishabh to talk about HQ, a cloud-based file system built on top of Claude Code and Codex that launched two days before recording.The origin story is good. Jacob meets Corey Epstein, sees a product called Indigo that was ahead of its time but waiting on AI to catch up. They stay in touch. Corey eventually puts Jacob on an internal tool called HQ. Jacob gets hooked, starts pushing the team to build a version for multiple people, and when Ramp published their internal Glass tool, Jacob tweets that they built Ramp Glass for everyone. The demand comes in fast, so he joined the company.The core problem HQ solves is one that Jacob kept running into across every business he consulted with. AI tools are built for solo use. Everyone's working in silos, repeating work, building their own janky version of the same thing. HQ gives teams a shared cloud workspace where skills compound. One person's breakthrough becomes everyone's baseline.Then the conversation goes somewhere more interesting. Rishabh pushes on who actually buys this. His argument is that the buyer isn't the average CEO, it's the founder, because founders are transformers and CEOs are optimizers. The person most likely to get value from HQ is someone who's willing to stay on the treadmill as the technology keeps moving, not someone who wants a finished system handed to them.Jacob's take on pricing is worth sitting with. A customer costs about a dollar a month to serve. The play is distribution. Get HQ into as many businesses as possible, stay close to how people interact with AI, and the monetization builds from there.The episode closes on something most people aren't saying clearly. Getting your team AI native isn't a software problem or a gamification problem. It's a coaching problem. And right now the gap between the people doing it well and everyone else is enormous.
Transcribe →E54: Become AI Native with Jim Benton from Adapt
May 1800:49:11Tap to summarizeIn this episode of the SaaS Operators Podcast, Jim Benton, CEO of Adapt, joins Rishabh, Jeremiah, and Jack to talk about what it actually looks like to build a company brain.Adapt connects all your tools, GitHub, Linear, HubSpot, Notion, Slack, and instead of scheduling tool calls one at a time like an MCP would, it swarms them. Hits everything at once, pulls the data back, and runs the best available model against it. That's why people say the answers look and feel different to Claude.The land vs. expand question kicks things off. Jim's take is that landing still matters, you've got to cut through the noise, but the real unlock is frictionless self-serve. Get people connected to a few tools fast. Let them hit the aha moment on their own. He tells a story about a CEO who signed up on a weekend, connected several tools, ran queries, and put a card in before sales could even reach out. That's the model.Jeremiah's been using Adapt long enough to notice his spend is about four times what he budgeted when he signed up, but he's not complaining. He understands what the brain means for token efficiency over time, and how sitting closer to the data gives you a real structural advantage over just piping Claude directly into your stack.The conversation gets into AI adoption inside companies, and it's not who you'd expect resisting. Senior executives are rolling their sleeves up. Younger employees in delivery roles feel the threat more directly. Rishabh's EA told him her goal is to have Claude handle 100% of her tasks. Jim's response is nuanced: the EQ parts of the job still need to be human. What you want is AI handling the computer thinking, and people doing the people thinking.Jim closes with what Adapt is actually becoming. A proactive reasoning engine. Something that spots the pattern you never thought to ask about, cross-references a product decision from six months ago with a deal you lost last week, and brings it to you before you knew you needed it.TLDR: The AI natives don't want to work with the non-AI natives. Get in or get left behind.
Transcribe →E53: GaaS for SaaS with Ronak Shah and Ankit Patel
May 700:44:46Tap to summarizeIn this episode of the SaaS Operators Podcast, Ronak Shah breaks down what the best SaaS brands look like from inside Gaas for SaaS.Rokt gets the top spot. Smaller than the others, but the most intentional operators on the list. They get the pay it forward model, they activate partnerships, and they understand that feedback is its own thing, separate from conversion. Proxima rounds it out, having graduated from e-commerce SMB into an enterprise play with Microsoft.The through line? The best SaaS operators are calm about AI. Engineers who've sat through a few hype cycles know that 90% of what's making noise right now isn't going to land.Then Jack pulls up a landing page he vibe coded with Profit AI. A Shopify page built by an agent using a VideoWise reference. Shoppable video widgets. A coupon code that redirects to checkout. The agent scraped the videos, built the section, and added features Jack didn't ask for.Jeremiah's take is that AI is putting a ceiling on what people will pay for SaaS. The build-it-yourself option has a real price now, and brands are going to start doing the math.Ankit brings the most grounded take of the episode. AI has unlocked the generalist. One person doing packaging, ads, landing pages, and branding without a team. He's running the experiment on Avi right now. 100 AI generated static ads aren't moving the needle any more than 15 hand-crafted ones did. Output is one thing. Impact is another.The conversation closes on something most people won't say out loud. Enterprises asking how to get on the right side of AI are going to get outcompeted by 2 people, a blank slate, and a stack of agents.TLDR: The tornado's coming.
Transcribe →E52: How AI Replaces People with Chase Mohseni from Creative OS
Apr 2901:15:13Tap to summarizeIn this episode Jack, Rishabh, Chase and Jeremiah talk about how AI is changing the way they run their teams day to day. Rishabh challenged Chase on why he keeps getting pulled into problems, and his read was that Chase wants to keep his finger in the pot, so the honest move is to admit that and pick two things to drive well.We got tactical on how each of us is actually using AI right now. Rishabh has FERMÀT MCP connected to every internal system, customer data, and their own product, so he can build customer decks while pushing his daughter on the swing.He thinks humans are better deployed as empathy and joy centers, and computers should do the thinking. Chase has trained his AI tools to tell him when he's being dumb and they've literally told him to put the laptop down and go to bed. Jack shares how he built a QA skill that uses agent browser to test every piece of functionality in his app after each change, and recently watched it set up TikTok Shop and Amazon integrations from start to finish without him being involved.Chase walked through where Creative OS is heading. Canva, Figma and Adobe are going to eat the horizontal creative market, so they're going vertical on performance creative and building what he calls the creative loop, spark of an idea to finished data backed asset. The 90 day plan is to make everything work seamlessly inside Claude, Cursor, or whatever IDE the customer wants to work in. Rishabh pointed out that specialist roles are going away regardless. AI gets everyone to the 90th percentile easily, the 99th percentile is still hard and always will be. He's hiring high agency, high grit, high horsepower people and is indifferent to what they're specifically good at. We closed on the reality that we're all in an AI pilled bubble. Chase's wife works at a big company that just told employees they can maybe try ChatGPT if they want. There are hundreds of millions of people who haven't downloaded Claude yet and have no idea what we're talking about.
Transcribe →E50: The Future of Software Businesses with Maxx Blank from Triple Whale
Apr 800:54:45Tap to summarizeThis podcast features an in-depth conversation with Maxx Blank, one of the co-founders of Triple Whale. Maxx shares the company's journey from a simple ecommerce dashboard that Maxx wanted for his own Shopify brand, to an AI-native data platform that serves over 30,000 of the fastest growing Shopify stores. We talk about internal tensions (fighting at work) and leadership approaches when navigating a rapidly shifting technology landscape. As well as some uncomfortable truths. Maxx Blank has built an incredible business by asking the same question every Shopify's store owner asks, how does this make us money? With billions of dollars of orders flowing through Triple Whale, they have a pretty good idea.
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