SAAS Operators

SAAS Operators
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3 CEOs from some of the fastest growing software brands and Jack trying to get as much information out of them as possible.

  1. 6D AGO

    E45: Swiping Left on Ads Like Tinder with John Gargiulo

    In 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?

    54 min

  2. FEB 23

    E44: 3,500 Customers and Zero Outbound with Shaan Arora

    In 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.

    53 min

  3. FEB 16

    E43: How to Survive The SaaS Sell Off with Dipti Desai

    In 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.

    53 min

  4. FEB 9

    E42: SaaS is changing with Yash Chavan

    In 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.

    57 min

  5. FEB 2

    E41: How to build for Shopify in 2026 with Daniel Patricio

    In 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.

    51 min

  6. JAN 26

    E40: Making Money with Memes with Jason Levin

    In this episode of the SAAS Operators Podcast, we talked to Jason Levin, the founder of Memelord. Jason explained how memes are the most useful tool for growth on the internet, and how “posting” is quickly becoming a necessity skill. We talked about government accounts memeing like creators, why shareability is more important than polish and professionalism and how Jason thinks about “memetic warfare” as distribution for ideas. Jason explains why he chose SAAS over media, how Memelord grew out of a simple problem he had himself and built in Bubble, and how improvements in AI agentic coding have made commercializing what you build the challenge, not building. We talked about how great ads might actually be memes, the decision between hard work and leverage work, and why most people are building random side projects with no business model. We also talk about copycats, why building one is a waste of a life, and how building software is getting easier every month.

    57 min

  7. JAN 19

    E39: Jack learns about Tech Debt

    In this episode of the SAAS Operators, we go from HVAC techs to stablecoins to tech debt, the question is the balance between speed to market and borrowing from the future.The trades, like HVAC techs, are winning because real work still needs to get done. Zach explains about how he's running ads for his brothers home services business, and says it’s basically shooting fish in a barrel. If he ever moves to the jungle he's turning into a media buyer.Then we talk about 2026, how building is getting cheaper, teams are getting smaller, and the bar is moving. Taylor Holiday describes stablecoins as contribution margin tech because traditional rails, wires and card fees are stuck in the Stone Age.The conversation closes on velocity and speed of change. How most decisions are two way doors, and why Jack believes shipping more, worrying less, and how “doing it right” kills momentum. But let's be honest, Jack's still learning about tech debt.

    44 min

  8. JAN 5

    E38: The Repeatable Launch Strategy with Matt Espinoza and Ryan Kaufman from Clover Labs

    In this episode of the SAAS Operators Podcast, we sat down with Matt Espinoza and Ryan Kaufman, the founders of Clover Labs to unpack how they're building a holding company designed to launch and scale multiple SaaS offers in parallel. Clover Labs is a 6 month old, 42 man team that increased MRR by 200K with one Slack message. We talk how they deliver LLM SEO in a fast changing environment, how organic is hard to measure, and the three buckets they anchor on when clients ask “what am I buying?” Matt and Ryan explain why they're starting as a done for you service powered by internal tooling, how Echo fits into the portfolio, and why Reddit is one of the most interesting high intent channels again. They also talk about how Clover Labs is mostly bootstrapped, and why they prioritized exit optionality while building a portfolio instead of one brand with many products. We talk about risk reversals by showing value first, and the challenge of keeping vision and direction clear once you're managing 40 people.

    46 min
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About

3 CEOs from some of the fastest growing software brands and Jack trying to get as much information out of them as possible.

Information

  • Creator
    SAAS Operators
  • Years Active
    2025 - 2026
  • Episodes
    45
  • Rating
    Explicit
  • Copyright
    © SAAS Operators
  • Show Website
    SAAS Operators

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