We Live to Build

Which is harder: being a founder or being an investor? Mike Lazerow has done both, building and selling companies for nearly $1 billion and now running a $400M VC fund and a PE firm. His answer might surprise you. In this interview, Mike unpacks the "existential dread" of entrepreneurship versus the challenges of deploying capital. He shares why he's most excited about AI transforming "boring" businesses , the reality of feeling lost and purposeless after a massive exit, and the single most important lesson he's learned: your network is your net worth. Check out the company: https://velvetseavc.com

Jeff Archibald is one of the lucky few who was able to sell his agency, and now he advises other agency owners. In this interview, he reveals what he would do differently if he had to start his agency all over again. We break down the critical mistakes most founders make, starting with the failure to set revenue goals and reverse-engineer a plan to meet them. Jeff explains why being too risk-averse and not reinvesting a portion of revenue into promotion hindered his agency's growth. He also shares the powerful 3-tier proposal method he adopted that transformed his pricing strategy by removing the fear of overpricing , and explains why you must proactively plan for your company's future instead of just reactively hiring when you get busy. This is a masterclass in building a sellable agency the right way. Check out the company: https://www.jeffarchibald.caBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Everyone is talking about an "AI-First" content strategy, but it's the wrong mentality, and it's killing your founder authority. In a world drowning in noise, you don't need to be everywhere; you need to be "undeniable where it counts." This interview with Ethan Monkhouse, founder of Naviro, breaks down the new rules for building authority as a founder. We explore why quality content is a hundredfold more important than quantity and how to use AI as a co-pilot for the heavy lifting, not as a replacement for human creativity. You'll learn the fatal flaw in most AI content tools and the framework for a content funnel that attracts your ideal customers without turning you into just another "supplier." Check out the company: https://naviro.aiBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

For many ambitious founders, bootstrapping is a slow death. After building a profitable, high seven-figure SaaS company for 10 years, Sameer Narkar realized his self-funded model was no longer enough to win. In this interview, Sameer explains why the AI revolution is forcing successful bootstrapped companies into raising funds to move faster. He breaks down his decision to seek investment after a decade of profitability, why he believes thinking about an exit is a distraction from building a great product, and how he plans to use the new capital to "buy growth" by investing in experienced sales teams and partnerships rather than burning cash on ads. Check out the company: https://konnectinsights.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Are you making the #1 mistake in AI pricing? Many founders are using their old SaaS pricing model, but for AI, that's a huge error. As pricing expert Dan Balcauski explains, it's like showing customers your “underpants”, and it's killing your sales. In this guide to AI pricing, Dan breaks down why the game has changed. Unlike traditional SaaS, AI products have significant variable costs and unpredictable customer value, creating a new set of challenges for founders. We explore the psychology of value-based pricing, how to choose the right pricing metric, and the strategies companies like Google and OpenAI are using to price their AI tools. Check out the company: https://www.producttranquility.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

How do you get a 70% reply rate on LinkedIn DMs? In this episode, I sit down with Gabe Lullo, CEO of the 8-figure sales development agency Alleyoop, who shares his exact method for filling his sales pipeline every single day. Gabe unpacks the hard truths about modern sales, explaining why most LinkedIn outreach is just noise and how hyper-personalized voice notes can get you a 7x higher response rate. He also breaks down his "calls and content" strategy, why prospecting for one hour daily is more effective than batching it once a week , and the critical difference between being a founder and being a CEO. Check out the company: https://alleyoop.ioBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

A shocking statistic reveals that 80% of leaders are dangerously behind on AI, and the window to catch up is closing fast. Most are trapped by day-to-day "urgent" tasks, ignoring the "important" work of AI adoption that will determine their company's future. In this episode, executive coach and founder of NewPo, Arielle Lechner, explains why so many leaders are failing to integrate AI and provides a clear roadmap to get started. We discuss how AI is transforming industries like executive coaching with tools like custom GPTs, how to automate workflows to save countless hours, and why you need to start thinking of AI as the most powerful assistant you've never hired. Check out the company: https://newpo.ioBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

What if your "great" work ethic is secretly sabotaging your business? It's a tough question, but one every founder needs to confront. The toxic hustle culture sold by Silicon Valley isn't just unhealthy, it's often unprofitable. In this episode, Personal Growth Advisor Brad Farris joins me to dismantle the "grind" mindset. We explore why overworking kills the creativity needed for breakthroughs , and how things like sleep, exercise, and hobbies are actually critical tools for productivity and sustainable success. If you're an entrepreneur chasing growth without burning out, this conversation will shift your entire approach to work. Check out the company: https://anchoradvisors.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Why stop building a startup from scratch when you could just buy a profitable business instead? For many entrepreneurs, acquiring an established company is a faster and more direct path to success. In this interview, Neel Bhargava, Founding Partner of the private equity firm NB Group Investors, unpacks his playbook for entrepreneurial investing. He explains the real differences between private equity and the venture capital world , how he raises capital on a deal-by-deal basis , and the unique investment themes he's currently pursuing, from youth enrichment to end-of-life care. If you're a founder tired of the startup grind, this conversation will show you an alternative path to building your empire. Check out the company: https://nbgroup.usBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Ever wonder how someone bought an $8M/year company with only $5,000? Gary Shelton did just that, and in this interview, he reveals his exact model. Gary is "The Coaching King," having acquired, scaled, and sold 12 different businesses over the last 50 years, each hitting 8-figures per year. He explains why mindset is the #1 reason most entrepreneurs never hit $1M a year in revenue and shares the lessons he learned from his mentor who built the first black-owned billion-dollar company. If you want to learn how to acquire businesses with little of your own money, build systems that allow them to run without you, and develop the perseverance to succeed, this conversation is for you. Check out the company: https://goshelton.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Are you accidentally destroying your team with a "Hero Leader" mindset? Many leaders believe their job is to be the primary problem-solver, but this approach can secretly sabotage team performance and create a massive bottleneck. This is the "Hero Leader" Delusion. In this interview, executive coach Dr. Carla Fowler (MD, Ph.D.) breaks down the psychology of leadership and reveals how even well-intentioned leaders stifle growth. We explore the critical differences between strategic thinkers and action-takers, why leaders must stop "putting out fires," and how to truly empower your team to achieve breakthrough results. If you're an entrepreneur, CEO, or founder, this conversation will challenge everything you thought you knew about building a high-performing team. Check out the company: https://thaxa.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Why do billionaires subtract? It's a powerful mindset that separates the ultra-successful from everyone else. In this dense masterclass on productivity, Todd Hagopian, who runs a $90 million business division, breaks down the wealth framework he learned from a billionaire: poor people add, rich people multiply, and billionaires subtract. He explains why you must ruthlessly focus on your "profit per minute" and eliminate the 80% of tasks that are wasting your time and mental energy. You'll also learn his "mind-blowing" SEO strategy to generate thousands of high-authority backlinks from evergreen content. Check out the company: https://playerone.sppx.ioBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

The New B2B Buyer Doesn't Want to Talk to You. Nearly 60% of B2B buyers are now millennials who grew up online and expect a seamless, self-service experience. In this interview, B2B expert David explains why personalization and a frictionless, multi-channel journey are the keys to winning over the modern buyer. Learn how to blend digital self-service with a strategic sales team, why your business may be "dead in 24 months" without AI, and his 6-month rule for making new hires. Check out the company: https://www.saltboxmgmt.comBook a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

Do you know Why AI Makes Your Website MORE Important, Not Less? While AI agents seem to be replacing everything, your website is the one place you control your message and the primary "repository of information" that large language models use to learn about your business. In this interview, domain broker Jeffrey Gabriel explains that without a well-written website, AI models can't easily find, understand, or prioritize your business over competitors. Learn why your site is the essential "home base" you need to succeed in the age of AI.Book a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisoryGuest: Jeffrey Gabriel, Founder of SawWebsite: https://saw.com

Every founder needs to hear this: A Bad Investor is Worse Than No Investor. Before you start chasing venture capital, you must understand the risks. In this interview, M&A expert Scott Kelly explains why bootstrapped founders of seven, eight, and even nine-figure brands often love their lives, while many VC-backed founders are miserably stressed. We break down the cautionary tale of FanDuel, whose founders got "little or nothing" after raising hundreds of millions, versus MailChimp, whose founders kept 98% of the proceeds from their exit after bootstrapping. This is a must-watch for any entrepreneur deciding how to fund their business.Book a 1-on-1 advisory session with me to apply these principles to your business: https://calendly.com/wltb/advisory

I took a sales ability test, and this sales test revealedmy #1 weakness. The results showed that in a sales context, I have a tendency to believe that talking is more important than asking good questions.In this unique episode, sales expert Mike Irving, founder of Advanced Business Abilities, analyzes my live test results, breaking down my strengths (like being a "Hunter") and my opportunities for growth (like "Discernment" ). We explore why everyone is in sales, whether they know it or not, and how understanding your personal traits can make you a more effective communicator.00:00 - Taking a Sales Test on a Live Podcast 01:00 - Why Everyone is in Sales (Even If You're Not a Salesperson) 02:50 - My Overall Results: The Good News 05:50 - A Surprising Weakness: "Knowing How to Deal With People" 07:50 - My #1 Weakness: The "Questioner" Trait 10:05 - Why I Subconsciously Talk More Than I Ask 14:35 - The Key to Success: Understanding "Discernment" 20:45 - My Unexpected Strength: The "Hunter" Trait 24:00 - My Secret Weapon: A High "Not Nice" Score 29:30 - Key Takeaways & How to Improve Your Own Sales Skills

To learn for free on Brilliant, go to https://brilliant.org/SeanWeisbrot/ . You'll also get 20% off an annual premium subscription.What if the fastest way to grow your company was to create problems on purpose? In this episode, Sean Weisbrot sits down with Ted Santos, President of Turnaround Investment Partners, to explore how problem creation sparks business transformation, leadership growth, and innovation.We dive into why questioning everything you know is essential, how neuroplasticity rewires the brain for change, and why self-mastery is the foundation of effective leadership. Together, we challenge traditional views on education, change management, and chaos to uncover a new paradigm for organizational success.You'll learn:Why CEOs should create problems to fuel transformationHow questioning established paradigms leads to growthThe role of neuroplasticity in problem-solving and innovationWhy self-mastery matters for leadership in times of chaosHow education conditions us to avoid the hard questions

AI is changing the way we discover, judge, and trust brands. In this episode, Sean Weisbrot sits down with Curtis Sparrer, Principal of Bospar, to explore how generative engine optimization, SEO, and authenticity are shaping the future of marketing and PR. From why FAQs might be your secret weapon to why AI should never be your final draft, this conversation reveals what every brand needs to know to stay ahead.

Borja Cuan is the Co-Founder of Four15Digital, a growth marketing firm that focuses on helping clients grow through strategic advertising.

Neil Twa is the Co-Founder of Voltage Holdings, which invests in and acquires ecommerce brands and SaaS brands.

Frank Hepworth is the founder of Yield School, a boutique consultancy that helps high-net-worth individuals gain intelligent exposure to digital assets. We discuss the evolving role of cryptocurrencies like Bitcoin and Ethereum in modern portfolios, the difference between ETFs and holding assets directly, and what smart, risk-aware investors are doing to navigate today's fast-moving market.Whether you're crypto-curious or already allocating capital into digital assets, this conversation explores frameworks, not financial advice, for understanding this volatile but increasingly relevant asset class.

William Welser IV, CEO/CTO & Co-Founder of Lotic.ai, explores how AI and behavioral science intersect, and why the way you use AI might be shaping your mind more than you think.We unpack the dangers of sycophantic AI, the importance of cognitive responsibility, and how education can protect us from blindly following tech.Topics include:* How AI mirrors your mindset* Why feedback from AI isn't always helpful* Empowerment vs. control in the age of algorithms* How to stay cognitively sharp in an AI-driven world

If you think adopting AI is optional, think again. In this episode, host Sean Weisbrot sits down with Alberto Rizzoli, Co-Founder & CEO of V7, to explore how businesses can build an AI moat—a defensible advantage through in-house AI capabilities.They discuss why relying on consultants isn't enough, how AI agents are transforming workflows, and what it takes to future-proof your business in an increasingly automated world. From law and insurance to professional services, this conversation shows how AI isn't just a tool—it's your next competitive edge.

Are you tired of low open rates, manual data entry, and sales reps burning out? Sean Weisbrot sits down with Jim Weldon, Founder/CEO of Prospect Desk to answer the question: “Can Agents Replace Cold Outreach?” Discover how smart agents, powered by AI, CRM integration, and advanced data enrichment—are transforming prospecting and scaling sales without the typical grind.

Is relentless hustle the only path to business success? Not according to Alexandra Gonzalez, founder & CEO of Savvy Marketers. In this insightful conversation, Alexandra shares why intention, planning, and anticipating client needs consistently outperform brute-force grind—especially in today's AI-powered world.We dive deep into:* Why “what if” thinking makes your business more agile and scalable* The playbooks Fortune 500 companies rely on (and how to adapt them for your startup)* How Alexandra landed corporate giants using relationships, certifications, and smart positioning* How to use AI without losing your human edge* The power of storytelling and personalized outreach in winning big clients

Why Can't You Fix an Order After Checkout? | Hamish McKay on E-Commerce, AI, and the Future of WorkIn this episode, Sean Weisbrot speaks with Hamish McKay, Co-Founder and CEO of a startup solving one of e-commerce's most frustrating issues: editing orders after checkout.We explore why platforms like Shopify haven't solved this yet, the technical and psychological challenges of post-purchase changes, and how AI is reshaping the customer experience.This conversation goes far beyond e-commerce, it touches on automation, the future of work, and how human creativity fits into an AI-driven world.

Thinking about bringing your manufacturing back to the U.S.? Wondering if it's worth the cost, risk, and effort?In this episode, I sit down with Samuel Fish, founder of Shield Security Doors and Shield Metal Works, who shares why he made the strategic decision to move his manufacturing from overseas back to the United States, and how it changed everything.We explore:✅ Why manufacturing where you sell can improve operations✅ The hidden impact of tariffs, currency fluctuations, and supply chain risk✅ How timing and the messenger can shape million-dollar decisions✅ The pride and power of Made in America✅ What most entrepreneurs get wrong about global productionWhether you're a founder, operator, or investor thinking about reshoring, supply chain optimization, or long-term brand positioning, this conversation will give you grounded insights from someone who's been through the fire.

Renan Devillieres is the Founder/CEO of OSS Ventures. We discuss how reshoring, automation, and shifting consumption patterns are changing the industrial landscape in the US and beyond.We dive deep into:* Why reshoring manufacturing is critical for long-term resilience* How automation and software are transforming factory design* What founders need to know about scaling production* The role of entrepreneurial spirit in revitalizing Europe's economy* How modern dealmaking and understanding your counterpart unlock real innovation

What if the smartest investment strategy in 2025... is ignoring AI completely?Travis Jamison, Founder of CapitalPad sits down with Sean Weisbrot to break down how he's making big bets on boring businesses, staying liquid in turbulent markets, and using under-the-radar SEO tactics to quietly dominate niche industries.

Do you trust AI in Architecture?Brian Corcodilos is the CEO of DesignBlendz, an AI-enabled architecture firm serving massive brands, to explore how AI, 3D visualization, and virtual reality are transforming the world of architecture. We dive into the future of building design, the rise of digital collaboration, and how emerging tech is reshaping the way we live and work.

What really drives successful private equity deals?Brandon Wolfe is the Co-Founder and Partner at Jordan Partners, a private equity firm that offers Wall Street experience and Main Street charm.Trust, emotional intelligence, and strategic capital allocation matter more than just the numbers. Risks of majority control, the emotional weight of selling a business, and how automation is reshaping private equity. Whether you're a founder or investor, this conversation is packed with real insights you won't want to miss.

Monica Garcia Duggal, Founder of Whole Health Plan, joins us to break down what most entrepreneurs get wrong about money. As the creator of the Financial Bytes method, Monica helps founders go beyond spreadsheets to build real, sustainable wealth — from budgeting and cash flow to strategic investing, taxes, and exit planning. In this episode, we dive into how to structure your business for profit from day one, why paying yourself first is non-negotiable, and how to use money as a tool for long-term legacy, not short-term stress. Whether you're bootstrapped or funded, this conversation will change how you think about financial health.

Stewart Cohen is the founder of SuperStock, a large media licensing platform.We explore licensing and ownership in the digital age. We break down the difference between copyright and licensing, reveal the traps hidden in social media T&Cs, and tackle the legal gray zones around AI-generated content. With lawsuits brewing and platforms shifting power away from creators, this episode is a must-watch for artists, photographers, filmmakers, and content creators navigating the modern landscape.

Ryan Davis is the Co-Founder of People First, which connects brands to creators.We discuss the evolving landscape of creator collaborations with brands, emphasizing the importance of niche positioning, the role of AI, and the need for authenticity in sponsored content. We explore strategies for monetization, the significance of creative control, and the metrics that influence sponsorship decisions. The dialogue also touches on innovative content creation methods and the potential for leveraging data to enhance future opportunities in the creator economy.takeaways

Is AI really objective, or just reflecting our human flaws?Daniel Nikic, the President and Founder of Cohres, explores the urgent need for auditing AI systems. We dive into how human bias, bad data, and lack of oversight are already shaping the way AI behaves and the very real ethical challenges that follow.From the dangers of unchecked algorithms to the importance of proper AI governance, this conversation will change how you think about artificial intelligence and what we must do to keep it in check.

Your website is bleeding money. Matthew Stafford, Managing Partner at Build Scale Grow, breaks down the brutal truths behind conversion rate optimization (CRO) and how AI, simplicity, and better communication can save your business from digital death.We talk about:⚙️ The CRO mistakes killing your conversions

Derrick Girard is the Owner of DGirard Consulting and the Author of Put to the Test.He shares his experiences of running a tech company while navigating the complexities of people management and the challenges posed by multiple lawsuits. He emphasizes the importance of self-awareness in leadership and discusses how external pressures can impact business growth. Derrick also reflects on the role of AI in management and the significance of bootstrapping in entrepreneurship. The conversation culminates in a powerful message about accountability and problem-solving without excuses.

Adam Schell is the of Brain Supreme, a 7 figure supplement business that produces a proprietary Psilocybin mushroom blend customers can use to microdose.

Arpan Nanavati is the Co-Founder & CEO of Cimphony, a Silicon Valley backed startup that recently raised over $5M USD, and the company has an AI that helps startups get access to smarter legal advice for less money.

Sze Wong is the Co-founder and General Partner of Zenith Venture Studio, which focuses on building AI startups.

Matthew Yahes is the CEO of Extend Your Team, a 7 figure, fully remote staffing agency that gets mid to high level remote employees to fill out your team.

David Miller is the Founder and CEO of Alchemy of Scale, a coaching practice that helps entrepreneurs systematize their operations and unlock true business growth.

Ryaan Ibtisam is the Co-Founder & Head of Legal of Cimphony, a Silicon Valley backed startup that recently raised over $5M USD, and the company has an AI that helps startups get access to smarter legal advice for less money.

Vol Goloshuk is the Founder and CEO of AI Champ.

Joshua Hale is the owner of JH Media and Consulting, which leverages cutting-edge AI technology and strategic business insights to help entrepreneurs realize their full potential.

Brook Shepard is the CEO and Managing Partner of Mason Interactive, a performance marketing agency that helps Higher Education and D2C brands with their Media buying strategy and execution, SEO, Creative, and Email Marketing.

Salim Rennewi is the Founder and CEO of SellAbroad, which helps brands expand into the MENA market (Middle East).

Russell Brand is the Founder & Managing Director of Resonsible, which consults companies on their IT and general strategy.

Matt Strippelhoff is the Partner and CEO/CRO of Red Hawk Technologies, which develops game-changing custom software and platform integration solutions for private equity and mid-market clients.

Ken Lundin is the Founder & CEO of RevHeat, which has taught businesses how to sell over $1B USD to date.In this episode we talk all about sales, the AI takeover, building a sales team, and more.