We Live to Build

Most companies waste their entire swag budget without ever seeing a return, and Ross Greenstein has the data to prove it. Ross, founder of a swag platform built for scaling businesses, reveals that 99% of swag is given away rather than sold, and even major brands like ESPN have tried and failed to turn branded merchandise into a real revenue stream. You will learn why rewarding your top 2% of customers with swag store credits is far more effective than expecting people to open their wallets for branded gear, and how smart companies are connecting their swag stores directly to CRM and HR systems to automate gifting at every key touchpoint. If you have ever wondered whether your company swag is actually doing anything, this episode will completely change how you think about it.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - What Is Swag and Why It Matters07:10 - The Origin Story Behind Ross's Company12:15 - Building Your Own Tech Stack vs. Third Party21:05 - The International Expansion Problem26:15 - Bootstrapping a Tech Company for Ten Years30:12 - The Long Game Mindset Ross Swears By31:32 - Empathy for Clients Drives Every Decision

What if getting laid off was actually the best thing that could ever happen to your career? Clayton Pritchard joins Sean to share how an unexpected job loss set him on a path to eventually acquiring the very company that brought him back in, turning a moment of uncertainty into one of ownership. Along the way, you'll learn why product marketing is far more than a launch function, and why embedding marketers early in the product development process leads to stronger adoption and fewer costly gaps at go-to-market time. Clayton also breaks down the information-gathering challenge at the core of great product marketing, from tracking customer behavior to aligning with engineering before the build is done. If you've ever wondered how to turn a setback into a strategic advantage, this conversation will change how you think about career pivots and business ownership.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - Clayton's Unexpected Path to Owning Olivine00:47 - Product Marketing Is Really a Business Strategy Role04:13 - Why Deep Links Matter After the Paywall07:05 - Building Solo With AI Changes Everything08:05 - The MVP vs MMP Distinction Clayton Uses With Clients12:33 - Why Marketing Shouldn't Set the Launch Date20:57 - How AI Is Reshaping the Product Marketer's Job24:11 - Review Sites Are Feeding AI Search Results28:34 - Every Career Mistake Led Clayton Here

What if the software you use every day was actually designed to make you succeed, not just to make you subscribe? In this episode, Sean Weisbrot sits down with Bryan McAnulty, founder of a platform that has helped more than 10,000 creators turn their knowledge into thriving online businesses. Bryan shares why building in the SaaS space is uniquely challenging, because your customers have to make a deep personal commitment to becoming someone before they ever log in. You will hear how Bryan approaches this by layering education directly into the product experience, helping creators get clear on their offers, build landing pages, and nurture their audiences, all because a more successful customer stays longer. It is a masterclass in building software that earns loyalty by genuinely caring whether the person on the other end actually wins.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - Helping 10,000 Creators Build Online02:53 - The Cold Start Problem Bryan Didn't Expect06:07 - Why Bryan Swears by Online Challenges09:12 - Tightening the Feedback Loop for Habit Formation17:53 - Stop Chasing Recurring Revenue Too Soon19:50 - Service as Software: The AI Shift Explained24:28 - Heights AI Three and the Proactive Agent Vision31:37 - Small Team's Secret Weapon Over VC-Funded Giants32:55 - Consistency Over Speed: Bryan's Biggest Lesson

What if the reason your business feels stuck has nothing to do with your strategy, and everything to do with who's missing from your team? In this episode, Sean sits down with Derek Fredrickson, a seasoned operator who spent fifteen years as a COO before building a company that delivers fractional COO support at scale. Derek breaks down exactly when a fractional COO makes sense for your business, why that sweet spot sits between one million and twenty-five million in annual revenue, and what founders get wrong when they think they need an executive but actually just need better operational support. You'll also hear how Derek's own experience of hitting the ceiling as a solo fractional operator led him to build a team model that now serves twenty to twenty-five companies at once, and why understanding how you're wired as either a visionary or an operator can change everything about how you grow.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - CEO vs COO: Which Role Is Harder?00:48 - Why Derek Built a Business Around COOs02:36 - The Right Revenue Stage for Fractional Help04:01 - Signs You're Too Deep in the Weeds05:56 - Start With a VA, Not a COO09:05 - Founder-Led Sales as Product Research24:20 - AI Adoption Depends on the Client's Appetite29:00 - Data Without Accountability Is Just Numbers35:32 - Know How You're Wired

What if your company is sitting on a goldmine of data but only using a fraction of it to its full potential? In this episode, Sean talks with Saurabh Gupta, an AI and enterprise data expert who reveals that while businesses have access to roughly 3,000 tools, most enterprises are only leveraging around 15% of them. Saurabh explains why focusing on outcomes rather than activities is the key to cutting through the noise of AI hype, and how his team consistently delivers results for clients in three to four weeks instead of the six weeks promised. You will also hear why the first two weeks of any engagement are the most decisive, and why protecting your company data is no longer optional in a world where someone is always ready to exploit it.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - Why Unprotected Data Gets Abused00:17 - Convincing Skeptical Customers in Six Weeks01:44 - The "Focus on Outcomes" Pitch That Works03:13 - First Two Weeks Are Make or Break04:22 - Your Data Is Your Most Valuable Asset06:37 - Why Bad Data Breaks AI Too10:27 - Getting Closer to the Source of Truth18:00 - The Modern Data Stack Is Bloated20:50 - AI Will Swallow the Analytical Layer25:00 - Three Weeks Compressed Into Three Minutes

What if the biggest mistake you're making with AI isn't using it too much, but using it without intention? In this episode, Sean sits down with Todd Anthony, an agency founder and AI-forward creative strategist, to explore why most founders treat AI like a vending machine instead of a medium they can actually shape. Todd breaks down how staying attuned to market patterns, rather than reacting to every wave of disruption, is what separates agencies that survive from those that collapse under volatility. You'll also hear his honest take on why the content landscape is flooded with hollow, AI-generated noise, and why audiences are desperately hungry for human authenticity underneath all of it. If you've been wondering whether to lean into AI or pull back, this conversation will change how you think about that question entirely.------------------------------------📈 WORK WITH SEAN------------------------------------▶ Executive Visibility: https://welivetobuild.com/services▶ Thought Leadership: https://sparkvox.io▶ Brand Visibility: https://www.welivetobuild.com/sponsorship▶ Inquiries: welivetobuild@gmail.com──────────🕐 CHAPTERS──────────00:00 - AI Slop Is Killing Audience Trust00:28 - The Three Men on a Ship Story02:05 - Running a $3M Agency in a Storm04:54 - Should You Actually Start an Agency?08:10 - The Trust Engine Concept Explained10:28 - AI as a Block of Clay20:48 - Building in Public Before You Have Proof26:10 - Guru Culture's Dirty Secret30:08 - It's Okay Not to Have All the Answers