In this episode of the SaaS Operators Podcast, we sat down with Laura Lalonde, founder and CEO of Gridbank, to unpack how she built a global marketplace for authentic, phone-shot content. Laura shares how her experience running creative for a gaming company spending millions per month on advertising led her to spot the demand for real, user-shot video before it was mainstream.
She describes how Gridbank pays creators for video content, using data to incentive supply that meets user demand, and has stayed profitable by focusing on one clear idea. We talk about why AI-generated content has only fueled Gridbank’s growth, how browsing real videos feels better prompting synthetic ones, and Laura’s vision to make uploading to Gridbank as natural as posting to social media.
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 sat down with Jason Lemkin who explains how AI and Shopify have completely reshaped the landscape, eliminating lifestyle businesses and forcing founders to adapt or get steamrolled.
He describes how defensibility in B2B SaaS is eroding, success in the Shopify ecosystem, and why hitting $10M ARR no longer guarantees a path to $100M.Jason Lemkin shares his rule for founders and execs. Deploy one new AI tool every month. Speed, brand, and execution matter more than ever.
The episode closes with an honest take on raising capital in ecom SAAS, why VCs avoid the category, and what it will take to build a truly fundable business in the age of AI.
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 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.
