SaaS Fuel

Jeff Mains
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  • UPDATED WEEKLY

Want to know why some SaaS companies scale while others stagnate? It's not just code and capital. You've found SaaS Fuel, where every Tuesday and Thursday, we're brewing up the kind of conversations you wish you could have over coffee with successful founders and industry experts. Join five-time entrepreneur and adventure seeker Jeff Mains every Tuesday as he gets real with visionary founders and executives who've built stellar software companies. They share the raw truth about their ups, downs, and 'I can't believe that worked' moments. Looking for practical tips you can use right now? Our Thursday 'SaaS Fuel Expert Series' brings you the smartest minds in the game, dishing out actionable advice on everything from AI and marketing to sales strategies and leadership. No fluff, just real tactics that are working right now. This isn't your typical 'how I built this' show. Whether you're figuring out product-market fit, building your first real team, or pushing past that million-dollar milestone, each episode packs the kind of insights you'd normally have to learn the hard way. Let's face it – running a SaaS company can feel like juggling while riding a unicycle. But you're not alone. Join our growing crew of founders and leaders who are figuring it out together, one episode at a time. New episodes drop every Tuesday and Thursday. Fuel your next big move. Hit subscribe and let's grow something amazing.

  1. AI in Marketing: What to Automate—and What to Never Hand Off | Paige Wiese | 376

    2D AGO

    AI in Marketing: What to Automate—and What to Never Hand Off | Paige Wiese | 376

    In this episode, Jeff Mains sits down with Paige Wiese — founder and CEO of Tree Ring Digital, a Denver-based digital agency with 16 years in the business. Paige brings a unique perspective to digital marketing rooted in her background in architecture, and uses that framework to help companies build websites and marketing systems with intentional structure, clear user flow, and long-term durability. The conversation covers the growing crisis of digital asset chaos — lost logins, expired domains, departed vendors, and employees who leave with critical access — and how Paige built a proprietary system tracking 200+ data points to help companies protect what they've built. They also dig into the dangerous temptation of blindly trusting AI for SEO, content, and ad campaigns, why the "mushy middle" of AI-generated content is killing brand differentiation, and how founders can build marketing foundations that actually convert rather than just generate traffic. Key Takeaways5:02 **From Architecture to Digital Marketing** — The shift wasn't intentional. A career pivot driven by health challenges in 2008 led Paige to teach herself to code — and her architectural background shaped everything that followed. 6:14 **User Flow = Website Architecture** — Just as architects think about how people move through a building (sink → kitchen → stove), Paige applies the same logic to website navigation. How does a user move efficiently through your digital "house"? 6:53 **The Build Sequence Matters** — Concrete can't be poured before the rebar is set. The same sequencing discipline from construction drives Tree Ring's website development process and is a key reason for their success. 10:09 **The Aha Moment for Digital Asset Protection** — The surge in calls from companies saying "my developer passed away," "my vendor disappeared," or "an employee left and I have no idea how to recover what she set up" crystallized the need for a systematic solution. 11:29 **Password Managers Aren't Enough** — They track passwords, not expiration dates, responsible parties, cards on file, or who has access to what. Digital asset protection is a much broader problem than most founders realize. 13:00 **AI Moved Fast — and That Was the Surprise** — The capabilities of AI weren't a shock; the speed of adoption was. In 18 months, the landscape shifted dramatically, and most companies are still catching up. 16:45 **Intent-Driven Marketing Starts With the Goal** — Never just run ads. Always start with: What's the goal? How quickly do you need ROI? Is this desperation mode or growth mode? The answer completely changes the strategy. 17:49 **KPIs Before Campaigns** — Too many founders start marketing before they've defined what success looks like. Without the right conversion tracking and KPIs in place, you'll never know if campaigns are working — and you'll be setting your agency up to fail. 19:23 **Tried-and-True SEO Still Wins** — Best practices, not hype, deliver long-term results. Mass AI page generation will eventually get your site penalized, just like mass backlink building did before it. 20:59 **Mass AI Content Is a Dead End** — Just going out and mass producing tons of content and FAQs is not the solution — especially if people can't find your site to begin with. 23:45 **When AI Almost Derailed a Google Ads Campaign** — Blindly following AI setup recommendations without understanding conversion tracking led a client to run an entire campaign with no way to measure results — and blow through a budget. 26:28 **AI Sourcing the Internet Isn't Your Expertise** — The reason people hire you is for *your* answer. AI is sourcing the internet for the answer. If your content doesn't reflect your values, mindset, and unique perspective, it's indistinguishable from everyone else's. 29:31 **AI as a Tool, Not a Crutch** — Not using AI as the end all be all, but a tool in your toolbox. Use it to start, then finish it yourself — especially when it comes to brand voice and product differentiation. 33:43 **You Own Everything** — Paige's founding principle: no matter what she sets up for a client, they own it. This ethical differentiator is what led naturally to building digital asset protection services. 35:23 **Holistic Marketing Metrics** — Looking at everything from start to finish. Traffic, rankings, and click-throughs are only a fraction of the story. Trace the full journey: did traffic convert, engage, and move toward a decision? 38:20 **Know Where Your Audience Is** — There are too many channels to be everywhere. Focus on where your exact audience lives. Sometimes direct outreach or speaking beats a $30K/month ad budget. 40:05 **Slow Down to Speed Up** — Getting to market with the wrong product or wrong audience won't get you anywhere faster. Slow down, validate your messaging, test your product, and know your audience before you hit go. Tweetable QuotesJust because AI told you that's the keyword phrase to put in doesn't mean it's right. You need to know what you're actually putting in there for a reason." — Paige Wiese"The reason people hire you is for YOUR answer. AI is sourcing the internet for the answer." — Paige Wiese"Getting to market with a crappy product or the wrong audience is not gonna get you anywhere faster." — Paige Wiese"If your messaging isn't tight, it's not going to get the results that you want — no matter how much you spend." — Paige Wiese"We want to make you happy, and if you're not, then go someplace else — but we're gonna do the right work to make sure you're staying happy." — Paige Wiese"You own this company. You own these assets. Why are you leaving so much on the table for other people to manage when that's part of your brand?" — Paige Wiese"Hope is not a strategy — especially in marketing." — Jeff MainsSaaS Leadership Lessons1. Build Your Infrastructure Like an Architect Sequence matters in construction and in SaaS. You can't pour concrete before the rebar is set. Nail the foundation — product-market fit, clear messaging, tracking infrastructure — before scaling marketing or launching campaigns. Skipping steps creates expensive debt you'll pay later. 2. Own Your Digital Ecosystem — All of It Most founders have no idea how many critical business assets live outside their control: logins, domain registrars, social accounts, third-party tools, ad accounts. If a key employee left tomorrow, what would you lose access to? Audit and centralize ownership now, not after a disaster. 3. Define Success Before You Start Spending Too many founders launch campaigns without defining KPIs, conversion paths, or what a "win" actually looks like. Your agency can't deliver results you haven't defined. Slow down, set the metrics, then execute. 4. Stop Chasing AI as a Silver Bullet AI is a tool, not a strategy. Mass-producing AI content, blindly following AI ad setup recommendations, or adopting every new tool because it promises results is a path to wasted spend and diluted brand. Use AI to accelerate, but apply human judgment at every critical decision point. 5. Differentiation Lives in Your Voice, Not Your Volume In a world where AI can generate thousands of pages overnight, the only thing that can't be replicated is your specific point of view. Your brand voice, your expertise, your perspective on why your product matters — that's what earns trust and drives conversions. Content without that is noise. 6. Marketing Should Convert, Not Just Attract Traffic, rankings, and click-throughs are vanity metrics without a functioning conversion path. Trace the full journey from first click to closed deal. Where do users drop off? What friction exists between intent and action? Fix the funnel, not just the top of it. Guest Resourcespaige@treeringdigital.com treeringdigital.com https://www.linkedin.com/in/paigewiese/ https://www.instagram.com/treeringdigital/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel’ Champion Leadership Group – https://championleadership.com/ SaaS Fuel ResourcesWebsite - https://championleadership.com/ Jeff Mains on LinkedIn - https://www.linkedin.com/in/jeffkmains/ Twitter - https://twitter.com/jeffkmains Facebook - https://www.facebook.com/thesaasguy/ Instagram - a href="https://instagram.com/jeffkmains" rel="noopener noreferrer"...

    45 min
  2. SaaS Longevity: How to Adapt in Tech Shifts and Customer Demands | AJ | 375

    4D AGO

    SaaS Longevity: How to Adapt in Tech Shifts and Customer Demands | AJ | 375

    AJ, founder and CEO of Daylight — an award-winning, Mac-exclusive CRM — joins Jeff Mains to share one of the most quietly remarkable stories in SaaS: a decades-long journey from refugee to bootstrapped CEO. AJ traces his path from arriving in Canada with nothing, to bartering his labor for computer access, to navigating the dot-com crash, multiple pivots, and a delicate transition from on-premise software to the cloud — all without outside funding. At the heart of his story is a deceptively simple framework: build strong systems, hire good people, and stay close to profitability. This episode is a masterclass in endurance, disciplined reinvention, and what it really means to build a company that outlasts technological waves and market cycles. Key Takeaways6:42 Adversity doesn't kill you — AJ's foundational lesson from arriving in Canada as a refugee: there is always a way out. That mindset became his default response to every business challenge. 7:36 Self-reliance as a survival skill — Indoctrinated early by family: don't count on anyone else. Combine curiosity with self-reliance and you'll find the knowledge you need. 12:27 Bartering for access — AJ traded free labor — sweeping floors, running errands — for equal computer time to teach himself to code. Grit over credentials. 14:38 Naivety as a founder asset — Market Circle was founded after watching eBay and asking "how hard could that be?" Sometimes naive conviction is the fuel that gets you started. 16:18 Timing killed the idea, not the idea itself — The dot-com bubble burst derailed AJ's first venture mid-fundraise. The idea was validated; the timing was wrong. Lesson: markets don't care about your timeline. 19:36 Apple community validation — People inside Apple told AJ to stop using the CRM as a portfolio piece and sell it. External market signals matter — listen when the right voices say "people want this." 27:08 The gradual pivot saved the business — A VC in San Francisco warned AJ about the "road of carcasses" of companies that ripped the band-aid on on-premise-to-cloud transitions. AJ changed strategy to a gradual 3-year migration and survived where others failed. 28:54 Let customers get comfortable with change — The gradual approach gave customers time to adjust, and gave the team time to fix infrastructure, scaling, and reliability issues before fully committing. 34:03 Bootstrapped discipline — Without outside capital, the rule is simple: stay close to the profitability line and reinvest constantly. Running a small deficit is only acceptable if you can make it up quickly. 40:43 Jobs to be done never change, tools do — Building relationships is a timeless job. The Rolodex became the CRM. AI will change the tools again. Anchor your product to the job, not the method. 44:30 Hire people who find solutions — Good people aren't just smart — they're open-minded, willing to work, and always looking for new ways forward. 45:22 Take vacations to test your systems — If the business collapses when you're gone for three days, you don't have a business — you have a job. Use time off to expose what's not yet built to run without you. Tweetable Quotes"Adversity doesn't kill you. As long as you take it in stride, whenever you run into adversity there is always a way out — you just start thinking, what's the way out?" — AJ"Don't count on anybody else. You count on yourself. That means you always have to prepare for you doing the work — and to do the work, you've got to go get the knowledge." — AJ"I'll work for free if you give me equal time on a computer. I'll sweep the floor, run errands, do whatever — just give me equal time." — AJ"There's no divine inspiration. You wanna do something, just do it." — AJ, on starting Market Circle"Had we not done the gradual approach, we would have killed the business." — AJ, on the on-premise to cloud migration"Help customers become comfortable with the change somehow. Whenever people are involved, things have to be carefully managed." — AJ"You wanna test that the business can run without you — because if it can't, you just have a job." — AJ"The job to be done — building relationships — doesn't change. The Rolodex became a CRM, and AI will change the tools again, but the job remains." — AJSaaS Leadership Lessons1. Adversity is a training ground, not a stop sign. AJ's early life as a refugee didn't break him — it gave him the mental framework that every business obstacle has a way out. That mindset compounds over time. Founders who've faced real hardship often have a quiet durability that's hard to replicate. 2. Curiosity + self-reliance is a compounding advantage. AJ didn't have resources, mentors, or credentials. He had a burning need to know why things worked, and the conviction that no one else was coming to save him. Those two traits drove him to bookstores he couldn't afford, to companies that rejected him, and eventually to building a product customers love. 3. Gradual > dramatic when navigating major transitions. The on-premise to cloud migration is a case study every SaaS founder should memorize. The "hard cutover" approach — common, intuitive, and fast — kills companies. The slow approach feels inefficient but it gives you the runway to fix your mistakes before they cost you everything. 4. Bootstrapped? Stay close to the line and keep reinvesting. Without VC money as a buffer, the game is different. AJ's rule: stay profitable (even by a dollar), and put every spare dollar back into the product. This isn't about being conservative — it's about staying alive long enough to adapt. 5. Anchor your product to the timeless job, not the current tool. "Build relationships" was the job 60 years ago and it will still be the job in 50 years. The tools evolve — Rolodex → CRM → AI-assisted CRM. If you stay anchored to the job your customers need done, you'll always have a reason to exist. If you anchor to your current feature set, you'll be disrupted. 6. Build a business, not a job — test it with a vacation. AJ recommends every founder take a deliberate vacation specifically to stress-test the organization. Two to three days first. Then longer. If it falls apart, you've just identified your most important engineering project. The goal isn't the beach — it's proving the system runs without you. Guest Resourcesaj@marketcircle.com https://www.daylite.app/ https://www.linkedin.com/in/alykhanjetha/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel’ Champion Leadership Group – https://championleadership.com/ SaaS Fuel ResourcesWebsite - https://championleadership.com/ Jeff Mains on LinkedIn - https://www.linkedin.com/in/jeffkmains/ Twitter - https://twitter.com/jeffkmains Facebook - https://www.facebook.com/thesaasguy/ Instagram - https://instagram.com/jeffkmains

    49 min
  3. Aligning Sales and Marketing for Scalable SaaS Growth | Javier Lozano | 374

    MAR 26

    Aligning Sales and Marketing for Scalable SaaS Growth | Javier Lozano | 374

    Javier Lozano Jr. didn't come up through brand or PR. He came through sales — and that lens has shaped everything about how he approaches growth marketing. Starting his first business in the teeth of the 2008 recession with a personal guarantee on a five-year lease, Javier learned early that you have to be strategic when the market won't forgive waste. That crucible turned him into one of the sharper go-to-market operators in B2B tech. In this episode, Javier walks through exactly how he scaled RapMate from roughly $1M to $20M ARR — not through guesswork or gut feel, but through a disciplined system of ICP targeting, messaging tested internally before it touched the market, channel diversification based on real signals, and a coordinated email engine that generated $1.5–2M annually on its own. If you're a SaaS founder trying to graduate from scrappy growth to a repeatable revenue machine, this episode is a masterclass in doing it the right way. Key Takeaways6:12 — Marketing through a sales lens Javier came into marketing through sales, not PR or brand. That background means everything he builds is oriented toward one outcome: influencing revenue. 7:03 — Marketing must influence revenue It can't be all demand gen all day. There has to be a balance — and a direct line connecting marketing activity to revenue outcomes. 7:52 — Enter old-school industries with a modern playbook In a facilities management company founded in 1976, Javier applied a B2C/SaaS marketing approach and stood out immediately — landing enterprise calls from Raytheon, Anheuser-Busch, and Dollar General. 10:35 — Ask more questions, peel back more layers The real pain is never the first thing a prospect tells you. The more you ask, the deeper you go — and agitating the real pain point changes the entire sales conversation. 12:44 — Don't try to boil the ocean When taking over as CMO, Javier's first move was to observe, not overhaul. Understand what's working before you touch the website, the messaging, or the budget. 14:22 — Test messaging internally before going external Instead of redesigning the website, Javier reoriented messaging inside existing email communications first. Lower risk, faster feedback, and you learn whether the market resonates before making expensive public changes. 15:34 — Only 15% of leads were in the ICP With 85% of leads outside their ICP, the team was burning money chasing the wrong people. The fix wasn't the message — it was the targeting. 16:11 — Meta delivered higher-quality leads than Google Even though Meta represented only 10–20% of ad spend, it was producing higher connection rates and close rates. Finding that signal — and gradually shifting budget — moved ICP match rate from 15% to 65%+. 19:01 — CAC dropped from $1,000 to $300 Better targeting and aligned metrics turned customer acquisition cost into a competitive weapon. At $300 CAC with a $2,250 average cart value, the math became predictable and scalable. 23:39 — "If it ain't broke, why fix it" has a shelf life Channel concentration is a real risk. Milk what's working, but always be looking 6–12 months ahead at diversification — before an algorithm change or account shutdown forces the issue. 27:10 — Signals don't have to be stats A VP calling your cell after two LinkedIn DMs is a signal. Three prospects in a row mentioning the same thing on sales calls is a signal. The sales team's frontline feedback is some of your most valuable go-to-market data. 32:05 — The $1 per lead per month email goal Javier set a simple but disciplined baseline for email: generate $1 per lead per month. That framework forced the team to think about email as a revenue channel, not just a nurture activity. 33:22 — Sales email from a real inbox: 40–50% open rates Emails sent from a salesperson's actual Gmail account opened at 40–50%. From a marketing email address, it was 15–20%. The channel doesn't change — the sender does. 36:53 — Leads closed 12 months after entry — from a Halloween email Buyers are in different stages at different times. If you stop communicating, you disappear. The long game in email is just staying visible until they're ready. 40:27 — The human experience is the last moat As AI slop floods inboxes and feeds, the people who create genuine human connection with their audience will stand out. That's not automate-able — and that's the point. 41:57 — Build the system manually before you automate it AI exposes broken systems. If you don't have a clear step-by-step process built out internally, automation will just break things faster. Do it by hand first. 44:36 — Find the one wedge and own it Founders go to market with too many use cases. Pick the one thing you can win in your sleep, get it so dialed in it's predictable, close that deal — then expand from there. Tweetable Quotes"Marketing needs to be influencing revenue in one way, shape, or form. It just can't be demand all day long." — Javier Lozano Jr."If you just ask more questions, you start unveiling more layers of the onion — and eventually they just tell you: you're the one I want." — Javier Lozano Jr."Don't try to boil the ocean. Go in and look at everything holistically before you change a single thing." — Javier Lozano Jr."I can't optimize a funnel based on feelings. Come to me with stats." — Javier Lozano Jr."Signals don't always have to be stats. A signal can be literally what the marketplace is telling you." — Javier Lozano Jr."The people who can create a true human experience with their audience are going to stand out over everybody else." — Javier Lozano Jr."Build the system first. Do it internally. Hate it until you don't like doing it anymore — then automate it." — Javier Lozano Jr."Find one wedge. Find one thing you can crush in your sleep — then go to market with that." — Javier Lozano Jr.SaaS Leadership Lessons1. Observe before you optimize. Javier's first move at every company is to audit, not overhaul. He doesn't change the website, the messaging, or the budget until he understands what's actually happening. Knee-jerk reactions from new CMOs — or founders trying to fix everything at once — destroy momentum. See the full picture first. 2. CPL is a vanity metric. CAC is the business metric. Getting 300 leads at $2 each sounds better than 40 leads at $15 each — until you realize none of the cheap leads are closing. Javier reduced CAC from $1,000 to $300 not by chasing lower cost-per-lead, but by improving targeting quality. The math only works when you trace the full line from spend to closed revenue. 3. Test messaging inside before you put it outside. Before touching the website, Javier retooled how the company communicated with existing leads in email. Lower risk, faster feedback loop, and real signal from a warm audience. Only after internal validation does it earn the right to go public. 4. Channel diversification is a survival strategy, not a growth strategy. Concentration risk is real. If 90% of your pipeline comes from one channel and that channel turns on you, you don't have a business — you have a dependency. Javier's approach: milk the winning channel, document the learnings, then gradually replicate the model on a second channel 6–12 months later. 5. Sales and marketing alignment requires a shared scoreboard. The marketing-sales tension is universal, but it's solvable. Javier's fix: define what a qualified lead looks like, track conversion rates at every stage, and make data — not feelings — the language of every internal conversation. When both teams are speaking the same statistical language, you stop fighting about whose fault it is and start building together. 6. AI amplifies what you already have — good or bad. Automation doesn't fix a broken system; it just accelerates the breakage. Build the process manually first, iterate until it works, then automate the parts that are truly repeatable. The human elements — curiosity, genuine connection, nuanced judgment — are your competitive moat in an AI-saturated world. Protect them. Guest Resourcesjavier@boldermediasolutions.com https://boldermediasolutions.com https://www.facebook.com/javykixs https://www.linkedin.com/in/javierlozanojr/ https://www.instagram.com/javy_is_bold/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond –a...

    50 min
  4. Building a Shopper-First Platform in a Retail-Driven Industry | Andy Ellwood | 373

    MAR 24

    Building a Shopper-First Platform in a Retail-Driven Industry | Andy Ellwood | 373

    Andy Ellwood is a repeat founder whose career took him from early-stage mobile startups acquired by Facebook and Google, through eight years building Basket.com, to shutting it down during the pandemic — and ultimately back into the arena with Stretch, an AI-powered grocery platform built to give families price transparency, shopping intelligence, and an advocate at checkout. In this conversation, Andy shares the through-lines connecting his entire career: curiosity as a competitive edge, falling in love with problems instead of solutions, and the hard-earned wisdom of setting non-negotiables before jumping back into founding mode. He explains why the $1.8 trillion grocery industry still lacks a single source of truth for pricing, how pre-purchase intent data is more valuable than post-purchase receipts, and why he built Stretch around shoppers first — even when the money is on the retailer side. Andy also makes a bold case that the AI moment mirrors the early app store era, and that the next wave of breakthroughs will come when AI agents start negotiating on behalf of consumers, not just serving the brands selling to them. Key Takeaways4:35 — Curiosity is a superpower Asking one more question than you're comfortable asking demonstrates understanding and opens doors that statements never could. 5:43 — Right place, right time isn't enough Being at Facebook and Waze during acquisition moments taught Andy that you have to know what to do when opportunity arrives — not just show up. 7:36 — One feature unlocked a trillion-dollar industry Location sharing on the iPhone made Airbnb, Uber, DoorDash, and Waze possible. Andy sees AI's current "education phase" as a direct parallel to early mobile. 10:08 — Fall in love with the problem, not the solution The best entrepreneurs define success as the pain point no longer existing — not the solution they built. As technology changes, the solution has to evolve. 12:01 — PTSD is real for founders After shutting down Basket.com, Andy took four years away. People kept asking who would solve the grocery pricing problem — and that pull eventually brought him back. 13:48 — Grocery lacks a source of truth Every major purchase category has an aggregator (Expedia, Zillow, GoodRx) — but not groceries. Stretch is building that missing layer. 15:52 — A list is not a cart Brand loyalty and substitution preferences make shopping lists deeply personal. Understanding this on the backend enables true personalization, not just price comparison. 18:01 — Grocery prices are up 25% since the pandemic Consumer loyalty is now up for grabs. 84% of Americans are considering trading down on brands, nutrition, and stores. 18:47 — 17% of surveyed shoppers skipped a meal In the richest country in history, food insecurity driven by pricing opacity is what makes Andy more determined than ever. 21:50 — Pre-purchase intent is the missing data set The $10B grocery data industry is built entirely on post-purchase receipts. Stretch captures what shoppers intended to buy — the seven items they didn't find are more valuable than the 18 they did. 23:32 — Receipt Checker: a patented AI agent for refunds 10–15% of the time, store discounts don't ring up correctly. Stretch's upcoming Receipt Checker will automatically identify overcharges and file refund claims on the shopper's behalf. 26:26 — People do what they're incentivized to do Charlie Munger's principle guides all of Stretch's product design. The receipt scan behavior is unlocked by giving shoppers a reason — get your money back. 28:24 — Serving shoppers is the thing nobody else is doing Most grocery tech serves brands and retailers. Andy chose the harder path — shopper first — and is walking alone for a while to get somewhere no one else has been. 34:38 — People buy from people, not logos Andy put himself on TikTok as a new dad documenting grocery savings. A single screenshot of the app's price map got 150K views and 8,000 waitlist signups before launch. 38:46 — The CEO has three jobs Ruthless commitment to the vision. Don't run out of money. Make sure your team is not blocked from doing their best work. 40:14 — Write your non-negotiables before you get pulled back in Andy had four criteria that all had to be true simultaneously before he'd found again. Having them written down protected him from jumping into things that weren't his work. 44:31 — The shopper-side AI agent The future Andy is building toward: your AI agent negotiates against retailer AI agents — finding the best deal on your specific basket within your driving radius — before you ever leave the house. Tweetable Quotes"Curiosity is a superpower. The questions you ask demonstrate more understanding than any statement ever could." — Andy Ellwood"It's not just about being in the right place at the right time. It's about knowing what to do when you're there." — Andy Ellwood"Fall in love with the problem, not the solution. The solution will have to change. The problem won't." — Andy Ellwood"Show me the incentives and I'll show you the outcome." — Charlie Munger (quoted by Andy Ellwood)"Serving the shopper is the thing that nobody else is doing with the determination that we are." — Andy Ellwood"Sometimes you have to walk alone for a little while to get to a place that nobody else has ever gone." — Andy Ellwood"The CEO has three jobs: ruthless commitment to the vision, don't run out of money, and make sure your team is not blocked from doing their best work." — Andy Ellwood"People don't buy from logos. They buy from people. They want to know who's behind this." — Andy EllwoodSaaS Leadership Lessons1. Fall in love with the problem, not the solution. Andy built Basket.com for eight years and watched it die when the pandemic wiped out their business model. What survived was his obsession with the problem — price opacity in grocery. The solution changed. The problem didn't. This is the only durable foundation for a long-building company. 2. Align incentives at every layer of your model. Stretch doesn't ask shoppers to scan receipts out of the goodness of their hearts — it offers them refunds on overcharges. Every feature is built around what shoppers are actually incentivized to do. As a SaaS founder, if your users aren't adopting a feature, ask what they think their incentives are — not what you want them to be. 3. Choose your non-negotiables before the pull comes. Andy spent four years away from founding after Basket. Rather than react emotionally when opportunity knocked, he had four written criteria that all had to be met simultaneously. Having those guardrails meant he didn't jump into something that was merely good enough — he waited until it was unambiguously right. 4. The CEO's only three jobs: vision, money, team. Ruthless commitment to the vision. Don't run out of money. Ensure your team is unblocked. Everything else is noise. This simple framework protects founders from diffusing their energy across low-leverage activities and helps them stay in their highest-value lane. 5. Forego early revenue to earn the right to build what matters. Inspired by Duolingo's founder, Andy made a deliberate commitment to B2B data revenue while resisting the temptation to monetize shoppers early. He told investors: "You're signing up to reshape a $1.8T industry — not to extract day-one ad revenue." Getting clear on what you won't do is often as strategic as knowing what you will. 6. Founders build trust. Logos don't. One TikTok video with a genuine story about grocery savings led to 150K views and 8,000 waitlist signups. No ad spend. Andy showed up as a real person — a new dad, worried about costs, building something to fix it. In a world where it takes an afternoon to spin up a company, the human behind the product is often the last true differentiator. Guest Resourcesandy@stretchai.com https://stretchformore.com/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel’ Champion Leadership Group – https://championleadership.com/ SaaS Fuel ResourcesWebsite - https://championleadership.com/ Jeff Mains on LinkedIn - a...

    48 min
  5. Why Most SaaS Companies Fail at Performance Marketing (And How to Fix It) | Anthony Chiaravallo | 372

    MAR 19

    Why Most SaaS Companies Fail at Performance Marketing (And How to Fix It) | Anthony Chiaravallo | 372

    Anthony Chiaravallo, founder and CEO of Vallo Media — a performance marketing agency that has placed over $100 million in paid media — joins Jeff Mains on SaaS Fuel for a candid, no-BS conversation about what actually works (and what doesn't) in B2B paid advertising. The conversation goes deep on performance media for SaaS: why cold lead gen ads are the fastest way to burn budget, how to build warm audiences before asking for a demo, and the massive cost savings that come from full-funnel thinking. Anthony exposes the hidden world of click fraud and bot traffic, explains how to set up clean data signals, and makes the case for why last-click attribution is quietly killing B2B ad performance. He closes with a pointed recommendation on where SaaS founders should — and should not — spend their limited marketing dollars. Key Takeaways3:44 — Anthony's Origin Story: From SVP to Founder Anthony's position was eliminated during COVID after five years building a paid media practice at a 4,000-person agency. He turned a side consulting hustle into Vallo Media, gave himself 6–12 months to match his corporate salary, and never looked back. 5:50 — Founder Mindset: Replace Yourself First The biggest shift from agency leader to founder is understanding that your primary job as CEO is to replace yourself. Anthony systematically identified what he was spending the most time on and hired for it — starting with paid media execution so he could focus on sales and strategy. 8:42 — How to Prioritize Your First Hires Start by asking: what am I spending the most time on that someone else could do better? Anthony's first hire was a paid search specialist — a person he found on LinkedIn, contracted for a project, and who has now been with him for six years running his entire paid media department. 11:43 — What Makes B2B SaaS Performance Media Unique Running cold lead gen ads against a B2B SaaS audience is "a fast way to set cash on fire." One client was paying $8,000 per ebook download — from unqualified leads. The fix: build warm audiences through awareness and video campaigns first, then retarget. That same client dropped CPL from $8,000 to $115. 16:49 — The Most Common Ad Waste Traps Brands celebrate cheap clicks without ever checking if those clicks are from real, qualified people. The most dangerous trap: reporting 1,000 clicks at $1 CPC while 90% of those users bounced in two seconds — bots or totally unqualified traffic. 17:46 — Clean Data Signals & Behavioral Conversions Instead of only tracking form fills, set up behavioral conversions: time on site, page views, video engagement. These "quality signals" train the ad platform's AI to find more people like your best visitors — not just whoever clicks cheapest. 20:40 — How Click Fraud Actually Works Bad actors spin up thousands of AI-generated fake websites, embed programmatic ad code, and deploy click bots to generate revenue from every ad served. Over half of annual digital ad spend is estimated to hit fake sites and bots. 21:39 — How to Protect Your Ad Budget Set up behavioral conversion tracking in Google Tag Manager, link it to GA4, and monitor closely whether platform-reported clicks match actual engagement in your web analytics. Vallo Media manually excludes 50,000+ fraudulent domains per month in programmatic campaigns. 26:56 — When a Flawed UX Tanks a Campaign Anthony walked a healthcare client through a campaign where 1,100 people clicked and zero downloaded the app — because the user flow required a QR code scan, app download, account setup, and SMS verification in sequence. He couldn't even complete it himself. 30:39 — UX Is a Paid Media Problem Your landing page, checkout, and signup flow are part of your paid media strategy. A client ignored Anthony's landing page recommendations for eight months — performance suffered the entire time. Paid ads don't exist in a silo. 36:18 — AI for Ad Creative: Useful Starting Point, Not a Replacement AI design tools can quickly improve creative direction (simplify text, modernize layouts, test variations) — but they need a human with marketing knowledge and taste to direct them and approve the output. "AI is only as good as the human giving it direction." 39:32 — The Right Way to Test Ads Reserve 5–10% of monthly budget for digital experiments. Test one variable at a time. Run AB tests monthly. One surprise finding: ads showing a person looking at the product outperformed ads with the person making eye contact with the camera for driving direct sales. 41:37 — Why Last-Click Attribution Is Killing B2B Ads Last-click attribution only credits the final touchpoint and ignores every podcast listen, social impression, and website visit that built purchase intent. In B2B SaaS, buying cycles can span a year — you need a mixed media model that assigns value across all touchpoints. 46:31 — Where to Spend (and Not Spend) Your Budget Don't start with Google Ads — competition is high and lead quality is inconsistent without brand foundation. Instead: invest in data immersion first, then build brand through top/middle funnel awareness and engagement campaigns. Once you've built warm audiences, bring Google Ads online to capture the demand you've already generated. Tweetable Quotes"The worst thing a B2B SaaS company can do in performance media is run lead gen ads against a cold audience." — Anthony Chiaravallo"Paid media doesn't exist in a silo. It's part of your overall marketing mix — and there's an effective way to do it." — Anthony Chiaravallo"You can't just turn on a paid ad and expect the leads to flow. Especially in B2B, you're skipping five steps." — Anthony Chiaravallo"Over half of annual digital ad spend is going to fake websites, fake bots, and hackers collecting a payday on every click." — Anthony Chiaravallo"AI is only as good as the human giving it direction. It doesn't have taste, context, or discernment." — Anthony Chiaravallo"Build demand before you try to capture it. Your whole job becomes easier when it comes to conversion." — Anthony Chiaravallo"If your user experience is not totally frictionless, your campaigns are not going to be successful." — Anthony Chiaravallo"You eat what you kill as a founder. It was much more rewarding — you see your business grow, your team grow." — Anthony ChiaravalloSaaS Leadership Lessons1. Replace Yourself Systematically, Starting on Day One Anthony's first move as a founder was identifying what he was doing that someone else could do better. He hired a paid search specialist immediately, freeing himself for sales and strategy. The lesson: your job as CEO is to continuously remove yourself from execution and move toward empowerment. 2. Sales Is Never Someone Else's Responsibility No matter how strong your sales team gets, as a founder you never fully hand off sales. Anthony kept business development as his north star from day one — because as he puts it, founders "eat what they kill." Staying close to the sale means staying close to the customer. 3. Hire People Smarter Than You in Their Lane Don't try to be an expert in everything. Find people who are better than you at the specific skill you need, give them the resources and autonomy to outperform you, and focus your energy on orchestration and vision. 4. Strategy Before Spend — Always 90% of success in paid media comes from setup: campaign structure, tracking, data signals, and understanding the customer journey. Before spending a dollar on ads, conduct a data immersion, audit your analytics, and map what your best customers' buying journey actually looked like. 5. Full-Funnel Thinking Beats Tactical Execution SaaS founders who jump straight to lead gen ads skip the awareness and engagement layers that warm audiences and reduce acquisition costs. Brands that invest in the top and middle of the funnel — video, content, thought leadership — have dramatically lower cost-per-pipeline when they eventually run conversion campaigns. 6. Measure What the Platform Won't Tell You Ad platforms report the metrics that make them look good. Real performance intelligence lives in your web analytics: time on site, page views, branded search volume, brand recall lift. Close the loop by sending quality signals back to the algorithm, and insist on UTM hygiene and proper GA4 setup before running a single dollar in spend. Guest Resourcesanthony@vallomedia.com https://www.vallomedia.com/ https://www.facebook.com/vallomedia/ https://www.linkedin.com/in/anthonychiaravallo/ https://www.linkedin.com/company/vallomedia https://www.instagram.com/vallomedia/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – a href="https://smallfishbigpond.com/" rel="noopener noreferrer"...

    51 min
  6. The Long Game in UGC: Building Trust Between Creators and Brands | Elijah Khasabo | 371

    MAR 17

    The Long Game in UGC: Building Trust Between Creators and Brands | Elijah Khasabo | 371

    What happens when a bored teenager starts a Discord trading group and accidentally discovers the power of video? For Elijah Khasabo, co-founder of Vidovo, it became the foundation for a bootstrapped UGC and influencer platform now serving over 200 brands and 20,000 creators. In this episode, Elijah shares the unfiltered origin story of Vidovo — from running negative for the first six months to crossing 20,000 organic creators without spending a dollar on paid acquisition. He breaks down why building for creators (not brands) is the real flywheel, how AI is actually strengthening the case for real human content, and what it means to stay gritty when the Stripe dashboard shows zero day after day. This is a masterclass in marketplace strategy, relationship-driven growth, and the kind of founder mindset that turns dark days into fuel. Key Takeaways3:52 — **The Origin Story:** Elijah explains how a Discord trading community led to TikTok affiliates generating 100M+ views, sparking his obsession with video and UGC. 5:25 — **First Big Win (That Was Really an L):** The Life Fuel cold email that landed after a month of silence — they lost money on the deal but it taught Elijah how to brief, strategize, and actually create content that converts. 7:05 — **Going All In:** Why December 2023/January 2024 was the turning point — when brands started buying in and creators began leaving full-time jobs for UGC income. 8:22 — **The Creator-First Flywheel:** Why most platforms build for brands (and why that's wrong). Vidovo built for creators first, which indirectly built for brands — because brands go where the best creators are. 10:09 — **Growth Without Paid Ads:** Relationship-building and showing up hungry at New York events — how sweating through the city and connecting person-to-person fueled 50–100 new creators per day organically. 11:31 — **Bootstrapping Philosophy:** Why going net negative in the early months actually built the right muscles — and why having no investors means entering future fundraising from a position of power. 14:02 — **SaaS is Humbling:** Launching at 19, learning to drop the ego, spending months alone building, and understanding that success requires working for it — nobody is just handed a software company. 16:04 — **Dark Days:** How Elijah nearly quit multiple times in the first six to eight months when the Stripe dashboard showed zero — and why "I have nothing to lose" became his survival mindset. 19:10 — **What Brands Get Wrong with UGC:** Volume is the real issue. Brands come in wanting 2–3 videos when they need 10 minimum to test, iterate, and find what actually converts. 20:52 — **AI's Surprising Impact on UGC:** AI content is actually driving more brands *toward* real creators — because consumers don't connect with AI ads the same way, and brands are noticing. 24:27 — **Building Creator Community:** Why quality beats quantity in community building — taking negative feedback seriously, building features from creator input, and making people feel heard. 31:13 — **Advice for Bootstrapped Founders:** Network relentlessly. Send 5–10 connection requests a day. Ask questions. Be the person willing to help, connect, and listen — doors open through people, not platforms. 33:48 — **Final Mindset Principle:** "You can really do anything you put your mind to" — when your goals are all you think about every day, you naturally become the person who achieves them. Tweetable Quotes"When you build for the creator, you're indirectly building for the brand. Brands wanna be where the best creators are." — Elijah Khasabo"I have nothing to lose. I'm 19. Where would I go if I quit? That's the mindset that kept me going through the dark days." — Elijah Khasabo"Entrepreneurship is a game of who. Build the right relationships and doors will open that no budget could buy." — Elijah Khasabo"If you give me a million dollars on day one, it would all be gone. Now I know exactly what to do with it — that's the value of bootstrapping." — Elijah Khasabo"Volume testing is everything in UGC. Don't launch 3 ads and call it a failure. Launch 10, find what works, and iterate." — Elijah Khasabo"AI UGC actually made our industry better. Brands are realizing consumers want real people — and they're coming to us because of it." — Elijah Khasabo"Put your mind toward the right things. If it's all you think about every single day, you're just naturally going to become that person." — Elijah KhasaboSaaS Leadership Lessons1. Build for the underserved side of your marketplace. Vidovo chose creators over brands — the side that doesn't pay. That counterintuitive decision created loyalty, word-of-mouth, and a quality flywheel that now attracts the paying side (brands) naturally. In any two-sided market, ask: who is underserved? That's your moat. 2. Losses that teach you are wins in disguise. The Life Fuel campaign cost Elijah money. But it forced him to learn strategy, briefing, and how to create content that converts. In SaaS, early customers who expose your weaknesses are more valuable than easy wins that mask them. 3. Bootstrapping builds judgment that money can't buy. Going net negative for six months taught Elijah exactly where dollars should go. When you bootstrap through adversity, you develop operational discipline that funded founders often skip — and that discipline becomes leverage when you do have capital. 4. Relationships are your most scalable growth channel. Vidovo scaled to 20,000 creators and 200+ brands without paid acquisition. The engine? Showing up to events, following up, being genuinely helpful, and playing the long game. In a world of funnels and paid media, personal relationships remain the highest-ROI growth lever. 5. Volume and iteration beat perfection. Brands that win with UGC don't launch one great video. They launch 10, find 3 winners, iterate on those 3, and test 7 new concepts. This is exactly how product-led SaaS should work too — ship fast, measure, iterate, and let data drive the roadmap. 6. Your mindset is your product roadmap. Every dark day Elijah survived made the next one lighter. The founders who push through are the ones who refuse to let the fire go out — not because it's easy, but because they've tied their identity to the mission. Grit isn't a strategy; it's the prerequisite. Guest Resourceselijah@vidovo.com vidovo.com https://www.linkedin.com/in/elijah-khasabo/ Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel’ Champion Leadership Group – https://championleadership.com/ SaaS Fuel ResourcesWebsite - https://championleadership.com/ Jeff Mains on LinkedIn - https://www.linkedin.com/in/jeffkmains/ Twitter - https://twitter.com/jeffkmains Facebook - https://www.facebook.com/thesaasguy/ Instagram - https://instagram.com/jeffkmains

    37 min
  7. Building Omnipresence: A Practical Guide to CEO-Led Content Strategy | Jake Isham | 370

    MAR 12

    Building Omnipresence: A Practical Guide to CEO-Led Content Strategy | Jake Isham | 370

    In this episode, filmmaker-turned-brand strategist Jake Isham breaks down what authentic storytelling really looks like in business. Jake has worked with over 150 entrepreneurs and brands, including Grant Cardone, Callaway, and 511 Tactical, creating content that's generated over 1 billion views. He shares practical frameworks for translating product features into compelling narratives, why consistency beats perfection every time, and how founders can overcome the fear of being the face of their brand. If you're ready to stop chasing attention and start earning trust through story-driven content, this episode delivers a human-centered approach to building brand authority. Key Takeaways[3:02] - The Trust Formula: People do business with people they know and trust. "Know" is just attention—they need to know you exist. "Trust" comes from showing you understand their problem, can solve it, and have proof you've solved it for others. [4:57] - Features to Benefits: Don't communicate what the feature is—communicate the pain it solves. Look at the "why" behind feature requests in customer comments. [7:10] - Everyone Sucks at First: Being on camera is just a skill that can be learned, like coding. Start with internal videos, get on other people's podcasts, and practice in low-stakes environments. [8:46] - Build Your Personal Brand: Founders like Elon Musk demonstrate that personal brands transfer from company to company. Most SaaS founders don't stay at one company—building that personal brand allows your audience to follow you. [11:45] - Consistency is the Biggest Killer: The biggest problem isn't doing anything wrong—it's being inconsistent or not starting at all. The voice saying "you suck" is usually your own, not others. [13:53] - Commit to 50: Jeff shares his strategy of committing to 50 episodes before deciding whether to continue—pushing past the discomfort to over 380 episodes. [14:26] - Batch Your Content: You can spend half a day per month and get all your content for that month. It doesn't have to be time-intensive if built correctly. [16:38] - Pre-Production is Key: The biggest growth from 1% improvements comes from pre-production—better questions, better guests, better thumbnails, better titles. [19:48] - Just Show Up: Like going to the gym, you just need to show up consistently. Even 20-30 minutes of pushing weight regularly will yield results. [20:06] - Two Years of Daily Content: Jake's brother posted multiple videos daily for two years before one video got 3 million views in 48 hours—proof that consistency compounds. [22:08] - The Dog Video Problem: Jake's dog video got 10 million views and gained him 180,000 followers—but they wanted dog content, not his actual business content. Make sure content aligns with what you want to be known for. [22:49] - Stay in Your Lane: Your SaaS solves one problem—your videos should address that one thing. Don't talk about unrelated topics just because they might go viral. [24:25] - Interest-Based Content Strategy: Start with what you're willing to do consistently. If you hate writing, don't start a blog. If you love podcasts, start there. [27:27] - Long-Form Leverage: Long-form video content is the king right now—easiest mass appeal, can be posted across multiple platforms with no extra work, and can be cut into vertical shorts. [28:30] - You Can't Oversaturate: People who will buy from you will consume content like candy. Those who complain about over-posting aren't your customers anyway. [28:47] - Present the Pain Point Early: Your audience needs to know immediately that your content is relevant to their problem—especially for long-form content where they're investing 10-60+ minutes. [33:42] - Never Add a CTA: A health influencer with 15 million subscribers shared that he's never put a call-to-action for his products and makes "an obscene amount of money"—when he does add CTAs, people actually stop buying. [38:22] - AI is Just a Tool: AI is a tool like the internet or digital cameras. Creativity and imagination are uniquely human—AI learns from people but can't create futures or "the new thing." [40:33] - Build a Feedback Group: Create a small group of peers at similar skill levels to critique each other's content with love. Beta test your content like you would your SaaS. [42:39] - It's Annoyingly Simple: Success isn't about being clever—it's about doing the obvious basic things for long enough. Tweetable Quotes"People do business with people they know and trust. The 'know' is just attention. The 'trust' is showing you understand their problem and can solve it." "Being on camera is just a skill. We all suck at everything when we start. The only way to get good at it is to do it." "By building that personal brand, your audience grows with you as you move from company to company. Most SaaS founders don't live in just one SaaS." "The biggest mistake isn't doing anything wrong—it's being inconsistent or not starting at all." "Content is never perfect. It will be a life of 1% improvements. The same way your SaaS is never done." "Unless you sit there and start coding, the app will not be built. Content is the same—just start." "If this video goes viral and this is the thing I'm known for, am I okay with that? Make sure every piece of content relates to what you want people to know." "Your SaaS doesn't do six things. Your SaaS does one thing—solves one problem. Your videos should address that one thing." "You can't oversaturate your content. The people who will buy from you will consume it like candy." "I've never put a call to action to any of my products, and I make an obscene amount of money. When I do, I actually lose money." - 15M subscriber health influencer "AI learns from people. What only humans are capable of is creativity and imagination. AI will always just put pieces together, but humans create futures." "It's annoyingly simple. Success is not about being clever—it's about doing the obvious basic things for long enough." SaaS Leadership Lessons1. Translate Features into Customer Pain PointsStop listing what your product does. Instead, communicate the specific pain your customers experience and how your feature solves it. When customers request features, they usually tell you why in their comments—that "why" is your marketing message. Example: Instead of "our CRM has date fields," say "Do you struggle to track your first call, shoot date, and release date? Our CRM is built specifically for podcasters." 2. Consistency Compounds More Than PerfectionShip your MVP. Release version 1.0. Start your podcast even if episode 1 isn't perfect. The biggest killer of content (and products) is inconsistency or never starting. Like building a SaaS, each iteration improves—but only if you ship. Jake's brother posted multiple videos daily for two years before one went viral with 3 million views. That's 730+ days of "failure" before breakthrough success. 3. Build Personal Brand as Portable EquityYour personal brand is the asset that travels with you from company to company. Most SaaS founders build, sell, invest, repeat. Elon Musk's audience followed him from PayPal to Tesla to SpaceX. Being the face of your brand isn't about ego—it's about building transferable authority that multiplies the impact of your next venture. 4. Batch Production Eliminates ExcusesFounders are busy, but you can create a month's content in half a day with proper batching. Record 4 podcast episodes in one session. Shoot 20 short-form videos at once. Build content creation into your operating system the same way you build product development sprints. Once it's part of the machine, time stops being the limiting factor. 5. Pre-Production Drives 1% GainsThe biggest improvements come before you hit record: better questions, better guest selection, better titles, better thumbnails. Spend 30 minutes thinking through titles instead of 5 minutes. Survey 30 options. This is your "version 10" optimization—but start with version 1. Don't let pre-production planning become a procrastination tool. 6. Content-Market Fit Mirrors Product-Market FitIf a video about your dog goes viral and gains 180K followers, but you're building B2B SaaS—you've built the wrong audience. Every piece of content should align with what you want to be known for. If you're building FinTech, talk about the financial space. If you're building for podcasters, talk about podcasting problems. Your content strategy should have the same focus as your product strategy: solve one problem for one audience. Guest Resourcesjake@jakeisham.com https://digitalshow.creativemindsofficial.com/ https://www.linkedin.com/in/jakeisham/ https://instagram.com/Jakecreativemarketing Episode SponsorThe Futureproof Series - a href="https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N" rel="noopener noreferrer"...

    46 min
  8. How to Sell SaaS in a Slow-Moving, Regulated Industry | Allen Cooper | 369

    MAR 10

    How to Sell SaaS in a Slow-Moving, Regulated Industry | Allen Cooper | 369

    In this episode of SaaS Fuel, host Jeff Mains sits down with Allen Cooper, co-founder and CEO of Ready List, to unpack what it really takes to build and scale SaaS companies in healthcare—one of the slowest, most regulated industries on the planet. The conversation dives deep into navigating 12-18 month enterprise sales cycles, recovering from product failures, hiring salespeople with domain credibility, and building remote culture that sticks. Allen candidly discusses which products flopped (and why early validation matters), how piloting with hospitals builds irreplaceable trust, and where healthcare technology is headed as AI and automation remove low-value tasks from clinicians. If you're building SaaS in a complex, regulated space—or considering it—this episode offers grounded, real-world insights on winning where speed isn't optional, but patience is mandatory. Key Takeaways[5:45] - From Investor to Operator: Allen explains how he transitioned from working capital partner to healthcare entrepreneur, finding the intersection between business interest and solving real transparency problems in healthcare quality metrics. [7:05] - The Transparency Gap: Healthcare's biggest early pain point was lack of transparency and the over-utilization problem driven by low-deductible plans that conditioned patients to overuse the system. [9:39] - The Ready List Origin Story: Ready List was born from a partnership with a West Coast hospital opening with a mission to eliminate paper—specifically targeting environmental services teams still relying on paper-based cleaning protocols. [10:57] - BR90 & Birth Registration: How a gap in the birth registration process led to building VR90, which reduced what used to take hospitals 15-20 minutes per birth down to 15-20 seconds using robotics process automation (RPA). [16:43] - Products That Flopped: Allen admits early products failed because they relied on someone's opinion and story without proper market validation—a costly lesson in distinguishing wants from true needs. [17:02] - The Pilot-First Approach: The critical shift to piloting products with early adopters before full investment, ensuring real validation and ironing out issues with actual users rather than guessing. [20:50] - Timing & Government Risk: Why timing matters enormously in regulated industries, where a single law or government decision can make or break your product overnight. [22:33] - Navigating Long Sales Cycles: Healthcare sales cycles run 12-18 months, complicated by varied fiscal years across hospitals. Allen shares how understanding budget cycles and offering no-cost pilots can compress timelines. [25:16] - The Trust Equation: Piloting builds trust exponentially faster than cold outreach. When hospitals experience both your product and your support, they become far more tolerant when issues arise. [28:34] - Sales Hiring Evolution: Allen's shift from hiring SaaS-savvy generalists to requiring healthcare domain expertise—seasoned salespeople who already have relationships and understand the ecosystem. [34:18] - Building Remote Culture: How Ancilla moved from full in-office to hybrid, discovering that quarterly in-person gatherings plus weekly virtual team socials (online games, baking sessions) build the trust needed for remote teams to thrive. [39:38] - Advice for Complex Industries: Time is both friend and enemy—don't give up prematurely on Blue Ocean products, but also don't drag on what isn't working. Always validate that you're solving a need, not a want. [42:05] - The Future of Healthcare Tech: Allen predicts increased adoption of robots and AI to handle low-value tasks (documentation, routine activities), freeing providers to focus on direct patient care where they add the most value. Tweetable Quotes"A want is hard to sell. It's gotta be something that's needed—if you take it away from them, you're gonna be giving back a pain point." - Allen Cooper"Don't rely on someone's opinion and idea and hope that it works. Partner up, pilot it, validate it—especially if you're not an industry person." - Allen Cooper"Getting a sales individual that is in the network really goes a long way with that trust. Being in that space is the lens that I have now." - Allen Cooper"When you just get bombarded by vendors you don't know, you're just like 'I don't want it'—I'm trying to find a way to navigate through that to build trust." - Allen Cooper"Time heals anything you think you can't get out of. Don't drag your feet, but don't get discouraged when things aren't working today, this week, or this month." - Allen Cooper"A need is resilient to any downturn of a market because a need will be needed regardless of what happens. Always serve a need, not a want." - Allen CooperSaaS Leadership Lessons1. Validate Relentlessly Before You BuildAllen's biggest failures came from building products based on someone's opinion and compelling story without market validation. The lesson: Don't invest heavily until you've piloted with real users. Early adopters will tell you if you're solving a real problem or chasing a phantom need. Partner with 2-3 hospitals (or relevant organizations in your industry) to validate assumptions before going all-in. 2. Solve Needs, Not WantsHealthcare taught Allen the critical difference between "nice to have" and "must have." Products solving true needs become indispensable—customers can't imagine operating without them. Wants are vulnerable to budget cuts and competitive pressure. Ask yourself: if we removed this solution tomorrow, would it create genuine pain or just mild inconvenience? 3. Pilot Your Way to Trust in Skeptical MarketsIn industries like healthcare where skepticism runs high and relationships matter, free pilots are worth their weight in gold. Allen shortens sales cycles and builds trust by offering 30-day no-cost pilots. Prospects experience both the product AND the support, building confidence that pays dividends when inevitable issues arise. In tight-knit markets, trust beats features every time. 4. Hire for Domain Expertise Over Sales SkillsAllen initially hired SaaS-savvy salespeople and trained them on healthcare. That didn't work. Healthcare sales requires understanding the ecosystem, knowing who to talk to, navigating 12-18 month cycles, and—crucially—having existing relationships. You can teach technology; you can't quickly teach 10 years of industry credibility. Hire seasoned professionals who already speak your customer's language. 5. Understand Timing and External ForcesIn regulated industries, government decisions, new laws, and policy shifts can make or break your product overnight. Allen experienced this when Wisconsin threatened to roll out a state solution that could have eliminated his product's value proposition. Stay attuned to stakeholders beyond your customers: regulators, payers, associations. Build products resilient to foreseeable changes, and always have a Plan B. 6. Remote Culture Requires Intentional ConnectionVideo calls alone won't build deep trust. Allen learned that purely remote employees struggled to integrate into company culture. The solution: quarterly in-person gatherings for team building plus weekly virtual social hours (online games, cooking together) to break down surface-level barriers. Hybrid models work when you're intentional about creating shared experiences that help teams weather challenges together. Guest Resourcesallen@ancillaventures.com www.ancillaventures.com linkedin.com/in/allen-c00per Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1N The Captain's Keys Small Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel’ Champion Leadership Group – https://championleadership.com/ SaaS Fuel ResourcesWebsite - https://championleadership.com/ Jeff Mains on LinkedIn - https://www.linkedin.com/in/jeffkmains/ Twitter - https://twitter.com/jeffkmains Facebook - a href="https://www.facebook.com/thesaasguy/"...

    47 min
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Want to know why some SaaS companies scale while others stagnate? It's not just code and capital. You've found SaaS Fuel, where every Tuesday and Thursday, we're brewing up the kind of conversations you wish you could have over coffee with successful founders and industry experts. Join five-time entrepreneur and adventure seeker Jeff Mains every Tuesday as he gets real with visionary founders and executives who've built stellar software companies. They share the raw truth about their ups, downs, and 'I can't believe that worked' moments. Looking for practical tips you can use right now? Our Thursday 'SaaS Fuel Expert Series' brings you the smartest minds in the game, dishing out actionable advice on everything from AI and marketing to sales strategies and leadership. No fluff, just real tactics that are working right now. This isn't your typical 'how I built this' show. Whether you're figuring out product-market fit, building your first real team, or pushing past that million-dollar milestone, each episode packs the kind of insights you'd normally have to learn the hard way. Let's face it – running a SaaS company can feel like juggling while riding a unicycle. But you're not alone. Join our growing crew of founders and leaders who are figuring it out together, one episode at a time. New episodes drop every Tuesday and Thursday. Fuel your next big move. Hit subscribe and let's grow something amazing.

Information

  • Creator
    Jeff Mains
  • Years Active
    2022 - 2026
  • Episodes
    377
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Jeff Mains
  • Show Website
    SaaS Fuel