SAAS Operators Podcast

In this episode of the SaaS Operators Podcast, we talked to Oliver Brocato, founder of Bustem.com and former founder of Tabs Chocolate, to unpack how he turned a pain point from his ecommerce days into a fast-growing SaaS business, protecting brands from copycats, counterfeiters, and scammers. Oliver breaks down how Bustem detects and removes bad actors across the internet, how most brands lose 5–15% of revenue to copycats, and how his platform recovers that value without expensive lawyers or lawsuits. We talk about building software as a non-technical founder, the slow grind of product iteration, and the transition from DTC storytelling to high-ticket B2B sales. Oliver shares how having 50,000 followers on X became a growth engine, how one tweet drove 400 signups in a day, and how he Bustem on authenticity and proof. He explains Bustem’s performance-based pricing model, how showing real ROI closes deals, and why transparency isn't the same as vanity metrics. The conversation dives into ecommerce versus SaaS economics, predictable inputs versus hits-driven luck, and the mindset shift from hype to value driven retention. Oliver closes by reflecting on automation, brand defense as a service, and the uncertain future of ecommerce in an AI-driven world where algorithms might shop for us before we even click “buy.”

In this episode of The SaaS Operators Podcast, we sat down with Tomer Tagrin, Founder & CEO of Yotpo, to talk about how he built a billion-dollar company, and navigated one of the boldest pivots in SaaS. Tomer tells the story about how Yotpo shut down its high growth email and SMS products to focus on reviews, loyalty, and AI, and how he’s rebuilding the company to be AI-native from the ground up. We talk about making tough decisions, sunsetting products to create focus and creating Yotpo Labs to move fast inside a large org. Tomer also shares his take on Shopify’s ecosystem, the reality that commerce is bigger than DTC, and how focus became Yotpo's competitive edge. The episode closes with a powerful explanation of what really matters, and what it's all for.

In this episode of The SaaS Operators Podcast, we sat down with Bennett Spooner, Co-founder of OperatorOS, to explore how he’s turning an automation agency into something that looks and feels like software. Bennett shares how his team built a customer service automation system that handles up to 90% of support without humans, and why Foreplay’s API is at the center of how he's productizing agency work. He explains how APIs, agents, and e-commerce automation are reshaping the line between service and SaaS, and why scalability isn’t about code, it’s about leverage. We dive into the debate over service versus software models, how to think about margins and multiples when you’re in the middle, and what the next phase of AI-powered automation means for operators at both marketing agencies and software companies. The episode wraps with a bigger conversation on what it takes to build a business that compounds while the rest of the industry tries to catch up.

In this episode of the SaaS Operators Podcast, we sat down with PJ Celis, founder of Judge.me, to unpack how he bootstrapped one of Shopify’s most dominant apps to $13M ARR without raising a single dollar. PJ shares the counterintuitive strategy behind Judge.me’s rise, why he built a company that drives prices down, creates consumer surplus, and wins by aligning perfectly with Shopify’s incentives. He explains how a low-cost, high-support model became an unbeatable moat inside the Shopify App Store, and why he believes price is the real innovation. We talk about the tradeoffs of running lean, how Judge.me scaled self serve, why simplicity beats ambition, and the organizational challenges of staying efficient as success compounds. PJ also talks about his shift into "founder mode," a philosophy of using software and structure to enforce accountability without middle management. The conversation ends with a deep dive into Shopify’s broader strategy to commoditize its ecosystem, the future of app store distribution, and what it really takes to build defensible SaaS without outside capital.

In this episode of The SaaS Operators Podcast, we dig into what it takes to scale a Shopify Plus SaaS when the market is no longer surging. Stuart Chaney, founder of Rivo, joins us to talk about the ceiling on Shopify’s TAM, the realities of platform risk, and why he keeps all his chips on Shopify despite the threat of sudden policy changes. We break down agentic coding with LLM guardrails, the grind of high-touch onboarding, and the what happens when you're building in public and growth slows down. The conversation moves through pricing power, competitor takeovers, and the simple truth that fixing the product beats every hack.

In this episode of the SaaS Operators Podcast, we talk about the changing landscape for ecommerce. We start with why venture-backed founders are leaving Shopify, unpacking the brutal math of cash conversion cycles and the near-impossible path to a true venture-scale outcome. From there the conversation moves into the “barbell effect” where tiny teams and massive enterprises thrive while the middle market gets hollowed out. We break down why Klaviyo became a pillar while most Shopify apps struggle, how AI is giving superpowers to the talented operators, and why survival is really a test of operator skill, not runway. We wrap with a conversation about the flow of capital, where dollars are headed next, and whether a new e-commerce boom is closer than anyone thinks.

In this episode of The SAAS Operators Podcast, we sit down with Drew Fallon, founder of Iris, to unpack his story moving from brand side to building finance software. Drew shares how Iris grew from a scrappy $500 a month product to a multi-million ARR platform helping brands forecast working capital and scale with confidence. We dig into the real differences between e-commerce and SAAS, the people challenges behind scaling a go-to-market team, and why raising prices can actually reduce churn. Drew also opens up about his playbook for partnerships, inbound growth, and the wave of distressed SAAS acquisitions he sees on the horizon. The episode closes on how Iris plans to reach $10M ARR and why finance tools can win by being embedded directly into a company’s weekly decisions.

In this episode of the SAAS Operators Podcast, we talk about the different games founders decide to play, and different definitions of success. Why the pursuit of money is the most noble thing you can do, and what happens when the next million doesn't meaningfully improve your life. The boys talk about different incentives, like status and legacy and how art and fashion can be tools for leverage and access outside of politics. They talk about what it means to play the long game, how sacrifice, consistency, and clarity on priorities influence decision making. But it's not without tradeoffs, founders trade friendships, fitness, presence with their family, and sometimes their own wellbeing. Ultimately, time in exchange for an outcome. The idea that everyone has to decide when the next incremental dollar, or representation of value, stops being worth the next incremental hour. The episode closes on conviction, choosing your game, accepting its sacrifices, and playing it hard enough to see compounding rewards over time.

In this episode of the SAAS Operators Podcast, we’re joined by Eli Weiss for a conversation about competition, focus, and culture in SAAS. We start with Judge.me, Yotpo, and Eli’s perspective on why competitors make you better, even when you want them to lose. From Olipop vs. Poppy to Shein and Temu, the group unpacks how competitors expand categories, legitimize markets, and drive product innovation. We talk about operating rhythms, how sequencing work accelerates learning, and how transparency in the form of receipts keep people accountable to delivering. Eli brings a hot take on brand, culture, and the differences between running fast-growth DTC brands and building software as a service. The episode closes on leadership lessons, bias to action, hiring fit, and the realities of scaling in a world where features can be copied overnight but brand and culture cannot.

In this episode of The SAAS Operators Podcast, we sat down with Jacob Posel to talk about his journey navigating the earliest stage of building a SAAS business and how he is thinking about AI, distribution and product-market fit. Jacob shares why chasing the “biggest opportunity” is not enough without obsession. How his background in marketing and advertising gives him an edge. He explains why stealth mode matters, how he is thinking about first hires, and why great tech is still the foundation of any surviving SAAS business. We talk about Icon’s controversial move into managed services, whether software as a service companies are destined to become... just service companies, and the reputational risks of overpromising when you only get so many first impressions. From cycle times in SAAS, to the important of momentum, and how AI is changing the way founders meddle directly in product development, this conversation is an exploration of how SAAS businesses starting today in 2025 operate.

In this episode of the SaaS Operators Podcast, we’re joined by Dan Pantelo, founder of Marpipe, for a deep dive into SaaS growth strategy, pricing, and go-to-market plays. We kick off with Judge.me’s $12M ARR business, debating whether it’s a massive success or still untapped potential, and explore why moving upmarket is often easier than defending the bottom. Rishabh shares how a $500/month SMB version of Fermat is scaling quickly through cold calling while email struggles in crowded inboxes. Dan walks us through Marpipe’s new free feed management tool and the upsell strategy behind it, sparking a discussion on “good enough” vs. “better” positioning. We wrap with a breakdown of SaaS pricing myths, the real role of subscriptions, and how events plus consistent social content create the “everywhere” effect.

In this episode of The SaaS Operators Podcast, we dive into the tradeoffs of venture capital, bootstrapping, and the gray area in between. Josh Perk, Founder & CEO of Vector, joins the crew to talk about building a YC-backed company and why his $130K AWS bill makes bootstrapping impossible. The conversation covers how Vector is taking on giants like 6sense and Demandbase with contact-based marketing, why fundraising isn’t just about dilution but also about partner quality, and how capital markets are shifting as funds scramble to deploy earlier. We talk about secondary liquidity, founder motivations, and the real math behind VC outcomes, and when it makes sense to turn down the sure thing. The conversation wraps up on the messy reality of employee equity, acquisitions, and how founders navigate the tension between personal wealth, team outcomes, and long-term vision.

In this episode of The SaaS Operators, we dive into Prime Day data, shifting consumer behavior, and what it signals about the broader slowdown in e-commerce. Jeremiah breaks down why Prime Day underperformed and why Amazon is no longer the discovery engine it once was. We explore how DTC brands are getting squeezed and why the winners are pulling further ahead. Rishabh raises tough questions around pricing strategy, flat-rate ceilings, and whether today’s growth is just pulling forward demand. We talk through SaaS retention, CAC misalignment, and why median order value might be the better metric. Zach shares how one DTC brand rebuilt their business from the ground up post-tariffs and the pricing insights that unlocked their next wave of growth. We also go deep on nostalgia-driven investing, broken brand stories like Harley-Davidson and Kodak, and the case for a PE fund that buys and revives brands built on childhood memories. The episode closes with a debate on flat pricing, competition, NRR tradeoffs, and whether private equity will start using AI agents to turn around bloated service-heavy SaaS companies.

In this episode of the SAAS Operators Podcast, Sean Frank, The CEO of Ridge and one of the hosts of the Operators podcast joins us for a frank conversation state of ecommerce on Shopify, Amazon and how SAAS is adapting. From pricing, to surviving market conditions, we talk about the tradeoffs between usage, seat-based and flat-rate pricing. Sean shares why Ridge is scaling through new product categories, not just wallets, and what it really means to have leverage as a $100M+ brand. We talk about ecommerce’s post-COVID contraction, the fading flood of VC money, and why fewer founders are entering the space. And we close with a debate on whether vibe coders will eat the Shopify App Store, how to survive rising CAC, and why niche monopolies might be the most underrated startup strategy.

In this episode of the SaaS Operators Podcast, we sat down with Niels Klement, CMO at Perspective.co, to talk about how they bootstrapped their way to $10M ARR almost all in Germany, primarily through paid ads. Niels breaks down how webinar funnels let them acquire customers profitably on the front end, why they collect annual revenue up front, and how they’ve avoided raising capital by staying cashflow positive. We talk about the economics of annual plans, free trials with credit card upfront. Niels shares why recruiting exploded as a vertical in Germany, why lead gen is their winning use case in the US, and how adapting their messaging has been their unlock as they expand globally. The episode ends with a deep dive into pricing, leverage, CAC payback rules, and what it really takes to build a profitable growth engine without venture money.

In this episode of the SAAS Operators Podcast, we sat down with Amit RG, the founder of Richpanel, to unpack how he built a profitable, efficient SaaS business serving e-commerce brands. Amit shares why he turned down Y Combinator and a Series A after raising and the choice to stay lean. We talk about why advertising hasn't worked for Richpanel, and how their $2K Automation Success Kit drives adoption, and why 40% of their customers sign multi-year contracts without being pushed. Amit opened up about the tension between being seen as the “affordable” option and building a premium product, and how brand perception plays into defensibility. The episode ends with a candid discussion on churn, customer success at scale, and whether we’re all thinking too small in the age of AI.

In this episode of the SaaS Operators Podcast, we sat down with Stephen Hakami, the founder of Wiza, to talk about his journey bootstrapping Wiza to $10M+ ARR and what happens when you hit an inflection point. Stephen shares why he's now considering raising capital after years of profitable growth, and has shifted from a profit-first mindset to a platform play that focuses on enterprise value. We dig into the tradeoffs between bootstrapping vs. venture scaling, the importance of retention metrics, and why gross logo retention tells a deeper story. Stephen also opens up about a near-death moment for the company when his sole developer passed away suddenly, leaving the entire product in limbo. The episode ends with a broader look at enterprise value, multi-product strategy, and the real meaning of resilience in SaaS.

In this episode of the SaaS Operators podcast, we unpack how FERMAT raised a $45 million. Rishabh breaks down why they went raised more than they initially planned to, how market pull forced their hand, and the exact process he used to close the round in just 10 days. We also get into ad efficiency, pricing psychology, why most brands under-segment their websites, and how generative AI is already building full funnels off a single goal input. The episode wraps with a spicy take on angel investing, risk math, and why you probably shouldn’t change your entire life strategy right after it starts working.

In this episode of the SAAS Operators Podcast, we talk about product launches, market expansion and building a system for reliable growth. Zach shares what he learnt from Foreplay’s latest product launch for Lens, including lessons around pricing, bundling and execution. The boys explores the difference between adding new customers vs. deepening value for existing ones, and why stacking launches can backfire. They talk about the power of referrals, how to operationalize them, and the surprising story of a DMT shaman that inspired a one-referral-per-user strategy. The episode ends with a broader conversation about motivating adoption, integrating into workflows, and what it actually takes to compound growth in SAAS.

In this episode of the SAAS Operators Podcast, we get into the realities of trust in business. What it means to break it, rebuild it, and keep moving. The boys open with stories of personal betrayal and reconciliation, then shift into platform tradeoffs, debating whether Shopify’s distribution is worth the cost. We talk about customer behavior across different ecosystems, how to think about pricing power, and the rising cost of growth in a tightening market. And the episode wraps with sharp takes on ad arbitrage, interpreting creative through customer eyes, and how one great ad can change a business.

In this episode of the SAAS Operators Podcast, the boys are joined by Cory Gill, founder of Alia. After a brief discussion on the pursuit of money and happiness and the stigma around being successful financially, they dive into the impact of fees on developer ecosystems. They talk about the long-term effects of market pressures and how to navigate cost pressures and efficiencies. The episode ends with a discussion about attribution challenges in customer acquisition and the importance of customer feedback.

In this episode of the SAAS Operators Podcast the hosts talk about the launch of Meta’s new AI App and how AI is changing the future of shopping and consumer behavior. They discuss the value of SAAS and its perception challenges, focusing on the evolution of software and customer expectations. They have a brief conversation about the impact of incumbents on Startups and end with a discussion on market saturation and product innovation where we all find out how much Jack loves butter.

In this episode of the SAAS Operators Podcast Danilo Vicioso, the founder of Mainstreet, joins the hosts and things get deep. They talk about systems, have a debate on raising vs bootstrapping and tell the stories behind how they named their companies. Zach tries to convince the boys that all legal disputes should be dealt with in a mud pit and the episode ends with a discussion on why subscriptions are the best thing since sliced bread.

In this episode of the SAAS Operators Podcast, Jeremiah is back with that “3 kid hair” and the hosts talk about the importance of buying your time back to maximize your effectiveness. They dive deep into how AI is changing SAAS and Jeremiah gives insights on how Shopify surpassed WooCommerce as the preferred website builder that leaves Rishabh speechless (almost). The episode ends with an update on what the hosts are doing to help their clients with the tariffs.

In this episode of the SAAS Operators Podcast, Jeremiah is still out and the hosts dive into why daily routines are so popular right now. They talk about the bad advice some of their VC friends are giving and the episode ends with a discussion about growth vs profitability.

In this episode of the SAAS Operators Podcast, Jeremiah is off having a baby and in the meantime, the hosts discuss what's new at Fermat and Foreplay, their daily routines and how software is immune to tariffs.

In this episode of the SAAS Operators Podcast, the hosts discuss OpenAI ad generation. They dive deep into solving problems vs following demand trends, highlighting the difference between tools and solutions. The episode ends with a brief discussion on the role of AI in SAAS PMF.

In this episode of the SAAS Operators Podcast, the hosts discuss the pros and cons of Bootstrapping vs VC Funding. They dive deep into the difference of lifestyle businesses vs the expectations of a VC. The conversation highlights their personal goals and entrepreneurial aspirations as well as the differences of a CEO and an entrepreneur and the psychology behind entrepreneurship. The episode ends with a brief discussion on product-led vs sales-led strategies.