Podcast
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Conversations with founders and operators at businesses between 1 and 100 million
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Episodes
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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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E49: How To Build An App That’s Worth Buying with Varun Kundra
Mar 3000:53:03Tap to summarizeIn this episode of the SaaS Operators Podcast, Varun Kundra , co-founder of AfterSell, talks about how the business was built around post-purchase upsells on Shopify. The core product sits in the window between checkout and the order confirmation page, a moment where conversion rates on relevant offers can hit 5-15% when set up properly, and where the highest-performing stores see the biggest AOV lift. Varun walks through how AfterSell eventually caught the attention of ROKT, a much larger company running third-party offers in the same post-purchase space, which ultimately led to an acquisition.We talk about the decision to sell at 23 years old, and what drove it. AfterSell had incredible traction, but there’s a belief that the Shopify ecosystem has a ceiling. The list of companies that have scaled to meaningful size inside it is short, Klaviyo, Recharge, a handful of others. The exit to ROKT gave Varun and his co-founders liquidity and something arguably more valuable, a front-row seat to how a larger, well-run business actually operates. Management, performance reviews, culture building, commercial strategy. None of that existed inside AfterSell before the deal.The back half of the episode opens up into a broader conversation about management philosophy in a fast-moving environment. Rishabh makes the case that a lot of traditional management principles, like giving criticism in private, were built for a world where information moved slowly. That world is gone. Jack and Rishabh talk through what it looks like to run a team where almost everything happens in public channels, why top performers tend to self-select in that environment, and where the ethical lines still hold. Varun ties it back to the meta-skill that survives any wave of technology: learning how to run a business where the value you deliver exceeds what you charge, and what you charge exceeds what it costs to deliver.
Transcribe →E48: From Service to SaaS with Aaron Schwartz & Daniel Brady
Mar 2301:05:18Tap to summarizeIn this episode Aaron Schwartz and Daniel Brady, co-founders of Orita, joined us and we talked about how they built an ML-powered audience intelligence product for e-commerce brands. Orita tells you which customers on your list want to hear from you, when and what about. It started as a consulting project where 5 out of 6 cold-outreached brands booked a meeting in under thirty minutes, it grew entirely through word of mouth, and the founding team was only 2 machine learning engineers.A near-perfect close rate was a pricing signal they couldn’t ignore. DB and Zach were only charging $50 a month to manage a brand's entire email strategy. Aaron doubled the price on the next three pitches and closed all three. We talk about how every retention tool hits a ceiling eventually. How retention as a category has a budget, which determines what a founder or CFO approves, regardless of the ROI in the dashboard. For some brands, Orita generated a 17x return and still got cut because the line item looked too big for a retention budget. That's what pushed the team into performance marketing, ads and direct mail, where buyers think in multiples of spend and the ceiling moves with results.Rishabh makes the case that Shopify warps the ecommerce founder's expectation of the cost of SaaS, because the real cost is buried in payment processing fees, and that gap shapes what merchants are happy to pay for every tool around it. DB talks about how he makes the every day decision on what to build and what to ignore, which features get commoditized in 3 to 6 months, and which ones require years of domain data, expertise and ML depth to replicate. The answer is some mixture of stay on the hard problem, build something durable, and outlast the noisy low value competition.
Transcribe →E47: Building The World’s First AI Creative Strategist with Alex Cooper & Maneesh Apte
Mar 1701:06:42Tap to summarizeIn this episode Alex Cooper and Maneesh Apte, two of the co-founders of Parker, joined us to talk about building an AI creative strategist that lives inside your Slack channel. Parker feels like a senior hire on your team. It sends you ideas without you asking. It tells you when something is a bad fit for your brand. It’s the product Alex Cooper was asking for, built by marketers that ran creative strategy for some of the fastest growing consumer brands, and you can feel it when you use it.We talk about how the Parker launch did 1.4 million views in 24 hours. How X took the post down all because a launch partner congratulated the team publicly and someone at X flagged it as a paid promotion. Alex Cooper had to speak to Nikita at X and Elon Musk’s brother to get his account reinstated. They hired 3 people in 12 hours to handle all the sales calls and blew past 1 million dollars in annual recurring revenue almost overnight. Rishabh brings up a piece from a16z about cornered resources and network effects being the only 2 moats that still matter and we get into where Parker's moat actually is. The integration layer is commoditized. Anyone can connect Reddit, TikTok and YouTube to a dashboard over a weekend with Claude Code. But documenting how top strategists actually think takes years. That's the layer Parker is building on.We talk about why dashboard-only tools and workflow-only tools are both going to struggle. Why most companies are further behind on AI than you'd think, and why marketing agencies are becoming Parker's best customers.
Transcribe →E46: Acquiring Marketing SaaS & Agencies with Chase Chappell
Mar 900:51:13Tap to summarizeIn this episode Chase Chappell, the founder of Sirge, Success AI, Ads Mastery and Partner at DOE Media, joins us to talk about building a vertically integrated e-commerce operation, acquiring marketing agencies and smaller SaaS companies, and why personal brand is still the biggest moat in a saturated market.We talk about Block's 4,000-person layoff and what it says about how the public markets now value software companies. Zach makes the point that AI is great at cutting costs but nobody's figured out how to use it to make dramatically more money, and how solving that problem is not obvious.Chase breaks down his approach to acquiring TikTok shop agencies, email firms, and smaller SaaS products, why he cuts the bloat immediately, and what he's actually looking for when he brings a new team in. He also gets into the problems with AI creative generation tools, reliability. The generations look great until your logo gets redrawn and your font comes out wrong.Chase Chappell is deeply integrated in every part of ecommerce, and it shows.
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E45: Swiping Left on Ads Like Tinder with John Gargiulo
Mar 200:54:10Tap to summarizeIn this episode we talked to John Gargiulo, the founder of Airpost. Airpost makes new video ads every week for enterprise advertisers spending $1M or more a month on Facebook ads. They've got human creative strategists using a UGC footage library, AI generated clips, and an engine that orchestrates all of it into 10-40 net new ads per client per week. Some of his clients never open the platform. They get a Slack message saying ads are ready, upload them, and run.It’s an agency with full agency, and a little bit of saas.Everyone tried something new with AI. Rishabh talks about how he built an MCP in an afternoon, started using Claude to interact with his own product, and said it was better than the UI his team built. Zach used Cowork to do 3 years of tax credit documentation that would've cost $65K through Deloitte and it only took him half a day.John was running 10 Cowork windows at once, and compared it to running 8 slow cookers in a kitchen.We talked about per-seat pricing dying once customers demand MCPs. The 10/80/10 model came up too. 10% is direction, 80% is execution, 10% is evaluation. That 80% of leverage might be headed toward 98%. The only part that doesn't get handed to an agent is the judgment call. What to build, where to aim, and whether it's actually good.We talked about how AI is actually making your day harder. When the busywork disappears, every hour is focused on real decisions. You become the bottleneck to your own agents. And the people pumping the brakes? Usually working through something emotional. The question everyone keeps circling is what do humans do when AI can do the work?
Transcribe →E44: 3,500 Customers and Zero Outbound with Shaan Arora
Feb 2300:53:27Tap to summarizeIn this episode we talked to Shaan Arora, the co-founder of Alia, about bootstrapping Alia Popups from $1M to $9M ARR in a year, bootstrapped, with zero outbound, and no venture capital. He started building Alia when he was 20, because he interned at Credit Suisse and decided he would do whatever it took to work for himself. Two customers, $20 a month, getting Etsy accounts blocked from cold outreach that most people would be embarrassed to do. Now he's got 3,500 customers, up from 1,100 last year, a 30 person team, and the freedom to design whatever he wants next.60% of their revenue comes from agency partners. The rest is word of mouth and referrals. People literally right click to inspect element on sites they like, see Alia in the code, and sign up. Their ACV 3x'd in the same period because bigger brands started showing up. Rishabh shared a stat that three enterprise customers at their company represent the same GMV as thousands of Shopify brands combined, making the case that depth of scale teaches you more than breadth of scale.We talked about whether Alia should expand outside Shopify or go deeper. Rishabh's take is the business is already telling you what to do, just follow the line. Jeremiah talked about expectations being lower outside Shopify and how that might actually be a good thing.We got into the agents conversation. What happens when someone spins up an LLM, connects it to Shopify and Twilio, and just does the thing your software does for pennies.Rishabh's counter is that the real job of a software vendor was always economies of scale and knowledge across customers, and that doesn't go away. Jack talked about wanting software that just does everything for him, the supremely lazy version of agentic commerce. We also talked about why taking capital might be the move right now, why the window to use it as a weapon doesn't stay open forever, and why Shaan can basically design whatever deal he wants at this stage.
Transcribe →E43: How to Survive The SaaS Sell Off with Dipti Desai
Feb 1600:52:36Tap to summarizeIn this episode we talked to Dipti Desai, the founder and CEO of Crstl, about why traditional SaaS pricing is dying and what actually makes software defensible in 2025. Rishabh posted on X that traditional SaaS doesn't survive the next two years. We talk about why vibe coding is a feature problem, not a cost problem. Zach tells a story about a friend with a door knocking app and a companion mobile app. Jeremiah tried to vibe code a trading bot. The code worked, but the math didn't math, describing his belief that domain expertise still matters. The underserved categories nobody wants to build for might get disrupted first or last, who knows and the companies with proprietary data underneath their workflows might be the ones that survive. We also talked about why product managers might be the most important job of the AI era, why OpenAI is burdened by 800 million weekly actives and still doesn't have a pixel for their marketing product, why Anthropic is shipping something useful every two days but attacking open source developers in their ecosystem, and whether staying in second place is actually a competitive advantage when the cost to solve problems keeps dropping.
Transcribe →E42: SaaS is changing with Yash Chavan
Feb 900:57:02Tap to summarizeIn this episode of the SaaS Operators, we talked to Yash Chavan, the founder and CEO of SARAL. We talked about why the pace of building has fundamentally changed and most SaaS is falling behind.Rishabh shares how his company went from one product to five in five months, why he stopped buying SaaS, and why doing anything manually at his company is a problem.Yash breaks down how Saral went from zero to a one million in 14 months on self-serve SMB, then tore the whole thing down. Tripled prices, went sales led, replaced the entire customer base with sticky mid market revenue. Now they're going multi-product and launching on the Shopify App Store.We talked about why quarterly planning is breaking, what Decagon's fundraise signals about how investors value agentic platforms, and whether AI tools make teams worse or just give them more swings. Jeremiah burned $400 in Replit credits in a week and still needed his own technical skills to ship. We also get into Alex Cooper's Parker launch, how Icons venture funded marketing left people confused even after 1.4 million views on Parkers launch video, and why most AI output sits in the boring middle of the distribution curve, where only the bleeding edge matters.
Transcribe →E41: How to build for Shopify in 2026 with Daniel Patricio
Feb 200:51:17Tap to summarizeIn this episode of the SaaS Operators, we talked to Daniel Patricio, the founder of ABRA Promotions. Daniel told us his story, from building startups in university, to working at a fast growing design agency, to spending eight years at Shopify through the IPO, and then leaving in 2021 to go full time on his own ecommerce business, selling South African Biltong.We talked about what broke for him after iOS 14, how discounts and offers are still way more complicated than they should be, and the moment he realized merchants needed storefront pricing that actually changes for the customer who is eligible.Daniel explains how ABRA started as a prototype in 2022, why the first year hard because nobody understood the product, and how Shopify’s shift from Scripts to Functions helped ABRA become the answer for more advanced discount use cases. He also shares what it looked like to grow 14x in a year, then another 3x the year after, and why staying bootstrapped gave them more optionality.We talked about Shopify’s direction, what “enterprise” really means in ecommerce, why the best merchants move fast and the enterprise moves slowly, and whether Shopify could ever build around ABRA or if the discount problem becomes big enough, just acquire a discounts app.We also get into ABRA’s partnership driven go to market, why positioning is less important than finding specific cracks partners care about, and how an eight person team ships quickly by keeping engineers close to the problem and avoiding heavy specialization.
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