We Live to Build

What if the secret to happiness wasn't a grand epiphany, but a bad movie playing at 2AM? In this episode, Sean sits down with Ben Narasin, a veteran venture capitalist who has backed companies like LendingClub, Rippling, and Omada Health, to explore what decades of investing at the highest level teaches you about life, patience, and staying true to your standards. Ben reveals why lowering the bar in venture is the beginning of the end, and how he learned to sit with the discomfort of seeing 2,500 pitches in a year and funding just one, without letting that silence become a compromise. You'll also hear his counterintuitive advice to founders: stop optimizing your valuation pitch and start treating your investor relationships like a marriage, because you'll be living with that choice for ten years or more.──────────────────────────────────────────────────────📚 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 - Happiness Is Wanting What You Have00:35 - Why Ben Only Funded 1 of 2,500 Pitches01:11 - LendingClub, Rippling, and the Fired Founder Pattern03:11 - Game Theory Will Ruin Your Investor Relationship06:44 - The ChatGPT Trick for Vetting Your VC08:14 - No Skeletons: The Open LP Meeting Experiment18:03 - Specifics Are Your Friend, Generalities Your Enemy25:04 - Work Hard When There's a Reason To31:28 - Sleep, REM, and the Brain-Cleaning Function33:46 - Life Is Hard for Everybody. Get Over It.

What if the real reason most businesses fail isn't strategy or market fit, but the behavior and value system of the owner themselves? In this episode, Sean sits down with Jay Aldebert, a business consultant who has studied patterns across 88,000 businesses and identified 11 biomarkers that predict whether a company will thrive or struggle. Jay explains why he starts every client conversation with a single pointed question about profit, and how the answer reveals far more than most owners expect. He shares why education has to come before measurement, drawing a parallel to how doctors measure without explaining, and why changing an owner's value system is often the hardest and most important part of the work. If you have ever wondered why smart, driven business owners keep hitting the same walls, Jay's framework will give you a completely new lens for looking at your own business.──────────────────────────────────────────────────────📚 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 - Business Owners Are Addicts to Their Own Behavior00:25 - Changing a Client's Value System From Scratch01:06 - The "Shock and Awe" Hook That Wins Clients04:03 - The Five Dimensions of Profit Explained05:37 - The Two-Day Diagnostic Nobody Else Offers07:45 - Why the Engagement Is a Loss Leader10:50 - Sand Castle Consulting vs. Project-Based Work14:01 - The 2-to-1 Return Assurance Unpacked22:53 - RTO Software and the 11 Business Biomarkers25:28 - One Profit Decision Affects 40 People

What if the single move almost no seller bothers to make is the one that multiplies your pipeline by eight? In this episode, Neal Goyal, a go-to-market leader who built 8x pipeline at Postpilot in just eight months, breaks down exactly how he did it using LinkedIn in a way that only one out of every hundred sellers actually does. Neal reveals why content is the last step in his three-part flywheel, not the first, and why showing up in your target ICP's comments before ever sending a message is the real foundation of trust. You'll also hear why the spray-and-pray outbound tactics that dominate most sales teams are actively eroding the trust you need to close deals, especially when thousands of software companies are all fighting for the attention of the same two thousand brands. If you want to understand how to compete for attention instead of just competing on features, Neal's approach will change how you think about pipeline building 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 - No Shortcuts to Building Real Relationships01:04 - How Neil 8x'd Postpilot's Pipeline02:45 - The Three-Part LinkedIn Flywheel Explained05:22 - Deposits Before Withdrawals on LinkedIn09:14 - Meet Your ICP Where They Actually Are18:16 - Why Neil Won't Let AI Build Relationships23:11 - Coaching Reps Out of LinkedIn Fear27:13 - Personal Brand Follows You Everywhere28:03 - Bet on Yourself Before You're Ready

What if the key to unlocking your team's potential wasn't hiring better people, but simply removing the friction slowing them down? Shelton Mercer III joins Sean to share how a shift from a 60-day process to a 60-minute one completely reframed how he thinks about the people around him and what they're truly capable of. You'll hear Shelton break down why power is less about authority and more about influence, how bringing together leaders from government, capital markets, and philanthropy in the same room creates a parity that cuts through political gridlock, and why framing collaboration around shared geography rather than competing agendas is what actually moves things forward. If you've ever wondered whether the systems your team works within are the real bottleneck, this conversation will make you think twice about where you're looking for solutions.──────────────────────────────────────────────────────📚 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 - Philanthropy Is Limited, Government Is Broken01:25 - The Power Shift Redefining Who Leads02:01 - Using the World Cup to Unlock City Change07:56 - One City, One Day, 100 Leaders08:34 - How Activate's AI Cuts 60 Days to 60 Minutes15:50 - AI Took My Designer's Job — Now What?19:21 - Upskilling Your Team Instead of Cutting Them28:05 - Pencils of Promise and Community Buy-In36:07 - The Three Traits Every Leader Needs38:00 - Mentor Told Me to Finish Some Ish

What if the key to smarter business decisions isn't more data, but knowing when to trust yourself over the algorithm? In this episode, Sean sits down with Robert Indries, a builder and investor who was working with large language models back in 2016, long before AI became a boardroom buzzword. Robert shares why, despite his deep technical background, he still believes human intuition catches what AI cannot, especially when it comes to detecting deception during company acquisitions. You'll hear how his team uses a rigorous due diligence process of up to 170 questions to surface hidden problems before they become costly headaches, and why the best questions on that list came directly from painful past experience. Robert also breaks down how he thinks about failure tolerance in acquisitions, including why growing a company's value before a black swan event can mean the difference between a loss and getting your money back.──────────────────────────────────────────────────────📚 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 - Getting Sellers to Tell You the Truth01:17 - The 21-Question Due Diligence Massage Method02:38 - Building a "Should Have Asked" Backlog04:41 - Why AI Can't Catch a Liar in M&A07:07 - Human Intuition Still Beats Generated Scripts09:06 - Sean's Podcast Pitch That Turned a Rejection Around17:25 - No Industry Is Safe From AI Disruption19:52 - Protoss, Zerg, or Terran: Which Future Wins?26:53 - Learning to Love as a Daily Skill

What does it actually take to back yourself when the whole world seems to doubt you? In this episode, Sean sits down with Travis McGregor, a technology pioneer working to reinvent how the world handles security from the cloud to the edge, including building a world-first innovation in just 90 days. Travis opens up about the defining moment at 22 years old when he froze on stage in front of a thousand people after his team changed his entire keynote without warning, and how that humbling experience shaped him into the prepared, accountable leader he is today. You'll hear how Travis learned to stop second-guessing himself, why true belief in your own ideas is a deeply personal journey, and how choosing to fall on his sword rather than point fingers became the foundation of his leadership philosophy.──────────────────────────────────────────────────────📚 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 - Believing in Yourself When Nobody Else Does01:44 - Choking on Stage at 22 Years Old05:22 - The Off-the-Cuff Pitch That Changed Everything09:21 - Patents Aren't What Most Founders Think12:27 - Why Your Data Is Never Really Yours14:56 - Flipping the Cloud-to-Edge Security Model23:13 - SLC's Play to Reach 600 Mobile Networks27:51 - 6G and the End of Anonymous Fraud Calls29:32 - Could SIMs Replace Broken Government Systems

What does it actually take to back yourself when no one else believes in you? In this episode of We Live to Build, Sean sits down with Stacie Shifflett, a self-taught entrepreneur and subject matter expert in federal government procurement and acquisition, who shares the raw story of orchestrating a 50 million dollar software company acquisition with zero prior experience at that scale. You'll hear how Stacie walked into a boardroom, discovered her name had been left off the org chart despite a signed employment contract, and chose to stand her ground rather than go along to get along. She also opens up about one of the hardest decisions entrepreneurs face, knowing when to say no, take your money, and walk away even when others frame it as a missed opportunity. If you've ever been underestimated or felt pressure to shrink yourself in a room where you clearly earned your seat, Stacie's story will resonate deeply.────────────────────────────────--─────────────────────📚 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 - Stacy Led a $50M Acquisition From Scratch01:00 - The CEO Who Didn't Know What to Do With Her03:28 - Leaving Money on the Table Was the Right Call05:22 - The One Time Stacy Actually Threw a Punch09:59 - Stacy Woke Up and Decided to Buy a Company15:40 - Self-Taught, No Degree, Still Outperformed Everyone26:02 - Peace of Mind Is Our Greatest Personal Asset29:22 - Know Yourself Before You Can Go Anywhere

What happens to marketing, consumer culture, and the businesses built around them when AI eliminates 90% of white collar jobs? In this episode, Sean sits down with Zachary Rischitelli to explore how networking, relationship-building, and human connection are becoming the most durable competitive advantages in an increasingly automated world. Zachary shares how his business has sustained client relationships for over sixteen years through genuine personal investment, not transactional card-swapping, and why showing up in person still moves the needle even as LinkedIn floods everyone's inbox. You'll also hear his simple but powerful networking reframe: be interested rather than interesting, a mindset shift that cuts through small talk and builds real trust fast. If you're thinking about how to future-proof your business and your relationships before the landscape shifts beneath you, this conversation will give you a lot to chew on.──────────────────────────────────────────────────────📚 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 Networking Hack Nobody Talks About00:22 - Building a 17-Year Business Through Relationships03:46 - "Be Interested, Not Interesting" in Practice06:22 - Reading Body Language at Networking Events08:39 - Moving Past Small Talk With Strangers11:31 - What Makes Networking Events Exhausting19:07 - Pitching a Marketing Agency in the AI Era21:15 - Who Are We Marketing to When AI Wins?28:17 - The Acquisition That Only Goes Forward36:53 - Work-Life Balance Is a Founder's Hardest Problem

What does it really take to break through a revenue plateau and build a business that outlasts your mistakes? In this episode, Ephraim Ebstein, an MSP entrepreneur who scaled past seven figures, shares the hard lessons he learned the long way. You will hear how developing financial literacy with the help of retired CEO mentors was the turning point that unstuck his business when it was trapped between seven and nine million dollars. Ephraim also breaks down why networking is never optional, showing you how a single spearfishing connection led to the job that taught him the entire industry and eventually the clients that made his company possible. And if you have ever wondered whether burning a bridge could cost you more than you think, his story of a former boss who later became his employee will make you rethink every professional relationship you have ever let go cold.──────────────────────────────────────────────────────📚 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 - Networking: Love It or Hate It?00:22 - Flying to Events to Find the Right Rooms01:08 - The One Connection That Started Everything03:49 - Retired CEOs Roasted Ephraim on Financials06:21 - Pay to Be in the Right Places11:26 - Two Takeaways, Two Relationships Per Event13:17 - Intentional Networking Beats Hoping for Luck16:00 - Never Burn Bridges Because The World Is Small21:07 - Diversifying Investments to Weather Any Storm40:00 - The Principle Behind All of Ephraim's Success