We Live to Build

Hosted by Sean Weisbrot

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326

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Sep 2026

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About the show

We Live to Build is the interview series for founders who are serious about building something that lasts. Hosted by serial entrepreneur and angel investor Sean Weisbrot, the show features 300+ raw conversations with 7-9 figure founders and investors, the people who've actually done it and are willing to talk about what it really took. Every episode goes deep on networking, AI, fundraising, and the harsh realities of scaling a company. Subscribe to upgrade how you build. Hosted on Acast. See acast.com/privacy for more information.

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September 22, 202635 min

He Built a 7-Figure Nearshoring Agency

What if one hire from Bogota could take your agency from a team of one to twelve almost overnight? In this episode, Sean sits down with Mike Bodkin, who built a staffing and talent placement agency around sourcing senior-level marketing professionals from Latin America. Mike shares how shifting his client targeting in the first six months led him to raise his pricing from a band of 2,500 to 3,500 per month all the way up to 3,500 to 4,500, without changing his markup model at all. You will also learn how his fixed-fee, month-to-month contract structure gives both clients and his business far better cash flow predictability than the hourly models most competitors rely on. If you have ever wondered whether one strategic hire or one pricing shift could completely change the trajectory of your business, this conversation will make you rethink what is actually holding you back. ------------------------------------ 📈 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 - From Agency Owner to Nearshore Talent Scout 01:14 - Raising Prices Without Losing Clients 02:14 - The Fixed Fee Model That Fixed Cash Flow 03:29 - "They Pay Us, We Pay Them" 05:17 - Solving the Problem He Lived Through 10:09 - Why Networking Beats Paid Acquisition 14:30 - Founder-Led Sales and Shaking Hands 20:19 - Sean's Focus Problem — And How He Fixed It 21:40 - The Two Career Lessons That Shaped Mike Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

September 15, 202632 min

99% of Swag Is Never Sold - Here Is What Actually Works

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 Matters 07:10 - The Origin Story Behind Ross's Company 12:15 - Building Your Own Tech Stack vs. Third Party 21:05 - The International Expansion Problem 26:15 - Bootstrapping a Tech Company for Ten Years 30:12 - The Long Game Mindset Ross Swears By 31:32 - Empathy for Clients Drives Every Decision Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

September 8, 202632 min

Getting Laid Off Led Him to Buy the Company That Hired Him

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 Olivine 00:47 - Product Marketing Is Really a Business Strategy Role 04:13 - Why Deep Links Matter After the Paywall 07:05 - Building Solo With AI Changes Everything 08:05 - The MVP vs MMP Distinction Clayton Uses With Clients 12:33 - Why Marketing Shouldn't Set the Launch Date 20:57 - How AI Is Reshaping the Product Marketer's Job 24:11 - Review Sites Are Feeding AI Search Results 28:34 - Every Career Mistake Led Clayton Here Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

September 1, 202634 min

Nobody Wakes Up Excited to Use Software - So He Built This Instead

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 Online 02:53 - The Cold Start Problem Bryan Didn't Expect 06:07 - Why Bryan Swears by Online Challenges 09:12 - Tightening the Feedback Loop for Habit Formation 17:53 - Stop Chasing Recurring Revenue Too Soon 19:50 - Service as Software: The AI Shift Explained 24:28 - Heights AI Three and the Proactive Agent Vision 31:37 - Small Team's Secret Weapon Over VC-Funded Giants 32:55 - Consistency Over Speed: Bryan's Biggest Lesson Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

August 25, 202637 min

Would You Rather Be a CEO or COO?

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 COOs 02:36 - The Right Revenue Stage for Fractional Help 04:01 - Signs You're Too Deep in the Weeds 05:56 - Start With a VA, Not a COO 09:05 - Founder-Led Sales as Product Research 24:20 - AI Adoption Depends on the Client's Appetite 29:00 - Data Without Accountability Is Just Numbers 35:32 - Know How You're Wired Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

August 18, 202632 min

3,000 Tools and Enterprises Only Use 15% of Them

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 Abused 00:17 - Convincing Skeptical Customers in Six Weeks 01:44 - The "Focus on Outcomes" Pitch That Works 03:13 - First Two Weeks Are Make or Break 04:22 - Your Data Is Your Most Valuable Asset 06:37 - Why Bad Data Breaks AI Too 10:27 - Getting Closer to the Source of Truth 18:00 - The Modern Data Stack Is Bloated 20:50 - AI Will Swallow the Analytical Layer 25:00 - Three Weeks Compressed Into Three Minutes Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

August 11, 202631 min

AI Is a Block of Clay and Most Founders Never Sculpt It

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 Trust 00:28 - The Three Men on a Ship Story 02:05 - Running a $3M Agency in a Storm 04:54 - Should You Actually Start an Agency? 08:10 - The Trust Engine Concept Explained 10:28 - AI as a Block of Clay 20:48 - Building in Public Before You Have Proof 26:10 - Guru Culture's Dirty Secret 30:08 - It's Okay Not to Have All the Answers Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

August 4, 202629 min

Talking to the $25/hr Shop Floor Worker Beat Every Spreadsheet

What if the most valuable business intelligence in your company is sitting on the shop floor, earning $25 an hour? In this episode, Sean sits down with Dustin Snyder, a human systems consultant who helps founders and CEOs understand what's actually happening on the ground inside their organizations. Dustin explains how leaders often design broken systems without realizing it, and why the frontline workers they rarely talk to hold insights that no spreadsheet can capture. You'll also hear why delivering that truth to founders requires as much emotional intelligence as it does hard data, especially when the leader's own decisions are part of the problem. If you've ever assumed you had a clear picture of your business just because the numbers looked right, this conversation will challenge that assumption entirely. ────────────────────────────────────────────────────── 📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M) ────────────────────────────────────────────────────── Get my brand new eBook free - https://welivetobuild.com/network ────────────────────── 📋 WORK WITH ME ────────────────────── ▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook ▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship ────────────────────── 🔗 CONNECT WITH SEAN ────────────────────── ▶ LinkedIn: https://linkedin.com/in/seanweisbrot ▶ Inquiries: welivetobuild@gmail.com ────────── 🕐 CHAPTERS ────────── 00:00 - The $25/Hour Guy Knows Your Business 00:33 - Delivering Hard Truths to Founders 02:09 - When the Founder Is the Problem 05:48 - Founder Proximity and the Scaling Trap 07:53 - Layers of Time Horizons, Not Tasks 13:59 - Workforce Insight Mapping Explained 17:42 - How AI Cut Analysis from Weeks to Hours 23:12 - Can AI Replace Human Trust in Interviews 27:21 - What Doing This Taught Him About Leadership Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

July 28, 202626 min

His Grandpa Worked Until 90 and Changed How He Sees Aging

What if the key to rethinking aging came from watching one man work joyfully into his nineties? In this episode, Sean sits down with Igor Gurovich, founder building AI-powered support for senior citizens, who shares how his grandfather's vitality well into old age reshaped his entire perspective on what it means to grow older. Igor explains why the global healthcare system is approaching a breaking point as the retired population grows faster than the workforce funding it, and why he believes the window to fix this is closing faster than most people realise. You'll also hear how his company sidestepped the challenge of getting elderly users to adopt new technology by replacing apps entirely with simple phone calls, and how that decision unexpectedly revealed just how deep the loneliness crisis among seniors truly runs. Check out the company: https://getcallie.care // https://www.linkedin.com/in/iogurovich ────────────────────────────────────────────────────── 📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M) ────────────────────────────────────────────────────── Get my brand new eBook free - https://welivetobuild.com/network ────────────────────── 📋 WORK WITH ME ────────────────────── ▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook ▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship ────────────────────── 🔗 CONNECT WITH SEAN ────────────────────── ▶ LinkedIn: https://linkedin.com/in/seanweisbrot ▶ Inquiries: welivetobuild@gmail.com ────────── 🕐 CHAPTERS ────────── 00:00 - Why Senior Care Is a Ticking Time Bomb 01:51 - AI Filling the Caregiver Shortage Gap 02:46 - Seniors Actually Love Talking to AI 03:08 - The Phone Call Hack That Changed Everything 04:31 - SaaSpocalypse and the Death of UI 11:42 - One Founder Disrupting Legacy Businesses Alone 13:22 - The Commercialization Wall No One Warns You About 15:18 - Building a Digital Memory of Your Loved Ones 20:31 - Elders Have Wisdom Nobody's Unlocking 23:39 - Do Only Things You Love Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

July 21, 202632 min

80% of the Workload Done Before a Human Touches It

What if 80% of the work in your industry could be done before a human ever gets involved? In this episode, Sean sits down with Ray Meiring, a founder rethinking the proposal process from the ground up, challenging decades-old workflows in an industry that has barely changed in fifty years. Ray shares how his team is using AI to reimagine RFP responses in a fully agentic world, why bouncing ideas off Claude at 3AM is now part of his product development process, and how he balances the speed of AI-driven iteration with the reality of customers who are still mailing binders. You'll come away with a sharper understanding of what it actually looks like to disrupt your own business model before someone else does it for you. ────────────────────────────────────────────────────── 📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M) ────────────────────────────────────────────────────── Get my brand new eBook free - https://welivetobuild.com/network ────────────────────── 📋 WORK WITH ME ────────────────────── ▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook ▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship ────────────────────── 🔗 CONNECT WITH SEAN ────────────────────── ▶ LinkedIn: https://linkedin.com/in/seanweisbrot ▶ Inquiries: welivetobuild@gmail.com ────────── 🕐 CHAPTERS ────────── 00:00 - Disrupting Your Own Business Before Others Do 00:57 - What Keeps Founders Up at 3AM 02:01 - Bouncing Ideas Off Claude Before Your Team 04:01 - Why Enterprise Customers Still Mail Binders 05:17 - Release to Sales First, Not Existing Customers 07:19 - Agents Talking to Agents: 18 Months Away 10:36 - Why Smaller Companies Should Sell Into Enterprise Now 17:24 - Building Agents on Microsoft Frameworks Explained 22:37 - Weeks of RFP Work Compressed Into Hours 30:25 - Stay the Course or Innovate Your Way Out Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.