141 | The investing Lesson Every Entrepreneur Learns the Hard Way with Andrew Horowitz

141 | The investing Lesson Every Entrepreneur Learns the Hard Way with Andrew Horowitz

What happens to an entrepreneur's wealth the day they finally step back from the business they spent decades building? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Andrew Horowitz, a nearly 40-year veteran of the financial services industry and host of The Disciplined Investor podcast, to break down why so many successful business owners struggle to invest their wealth with the same discipline they used to build their company. Horowitz and Lonergan dig into why an entrepreneur's own business behaves like one of the riskiest assets in their portfolio, the real math behind a market drawdown, and a practical dollar-cost-averaging strategy called "one foot in, one foot out" that helps investors get off the sidelines without the fear of a lump-sum decision gone wrong. Whether an entrepreneur is still building free cash flow inside the business or preparing for a future liquidity event, this conversation lays out a clear framework for separating business risk from investment risk, building an all-weather portfolio, and making decisions based on process instead of emotion. Key Takeaways: * Why business owners often confuse business success with investing skill, and why that gap creates unnecessary risk * How a founder's business behaves like a micro-cap stock, exposed to shocks that can undo years of hard work * The real math behind a drawdown: why a 50% loss requires a 100% gain just to break even * The psychology of a liquidity event, and why mark-to-market investing feels different than watching a home value rise * The "all-weather portfolio" (or "flower garden") approach to true diversification * The "one foot in, one foot out" dollar-cost-averaging strategy for investing without the fear of bad timing * Why waiting for a market pullback can end up costing more than staying invested * How to separate business risk from investment risk after selling or exiting a company Learn More About Andrew: * The Disciplined Investor podcast / Andrew Horowitz [https://thedisciplinedinvestor.com] * DH Unplugged podcast (Andrew Horowitz & John C. Dvorak) [https://www.dhunplugged.com/category/podcasts/] Resources:    * Visit vitalwealth.com/resources [http://www.vitalstrategies.com/] to download FREE resources      * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

140 | Business Fuel: How to Find the Right Capital for Every Stage of Growth with Levi King

What does it actually take to get a business loan and why are so many successful entrepreneurs getting denied? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Levi King, co-founder of Nav and one of the foremost experts on small business credit and financing in the country. Levi brings a rare combination of real-world experience, having started five businesses, secured over forty commercial loans across multiple industries, and built Lendio, the nation's largest commercial loan broker and the technical depth of a fintech founder who has spent a decade solving the financing gap for millions of small business owners. This conversation goes far beyond the basics and delivers a masterclass on what lenders are actually looking at, why most entrepreneurs are flying blind, and what to do about it. Patrick and Levi unpack why business credit and personal credit operate by entirely different rules, how a single bounced check can quietly disqualify an otherwise strong borrower, and why the way a business is structured legally can make or break a loan application before it ever reaches an underwriter. With credit markets expected to tighten in the months ahead, Levi makes a compelling case for why right now, not when you need capital, is the time to build your financial foundation. Whether you are actively seeking financing or simply want to be prepared when the opportunity arises, this episode will change the way you think about capital, credit, and the financial infrastructure of your business. Key Takeaways: * Business credit and personal credit are completely different, low data consistency across commercial bureaus means a strong D&B score does not guarantee strong Experian or Equifax scores * The Fair Credit Reporting Act does not apply to business credit, disputes move slower and protections are weaker * Bounced checks are one of the most common and costly mistakes, even three per month can disqualify an otherwise strong borrower from many lenders * Lenders use AI and trending deposit data to determine whether a business is growing or quietly in distress * Sole proprietors face significant financing disadvantages, forming a legal entity is critical for access to business loans and credit cards * Mixing personal and business finances is an automatic decline with most lenders * Get a line of credit before you need one, in a tightening credit cycle, existing facilities stay active longer than new approvals get through * Nav aggregates personal credit, all three commercial bureau data sets, and cash flow data via Plaid to show business owners exactly how a lender sees them * The best time to build your financial profile is before you need capital, subprime emergency loans often accelerate business failure rather than prevent it * Customer revenue is always the best capital, financing should be a growth lever, not a lifeline Learn More About Levi: * Nav platform: nav.com [nav.com] Resources:    * Visit vitalwealth.com/resources [http://www.vitalstrategies.com/] to download FREE resources      * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

139 | How to a Build a Sales Team so the Business can Scale with Mike Huey

Are you still the most important person in your sales process? For most entrepreneurs, the honest answer is yes and it's the single biggest thing capping their revenue, their company's value, and their freedom. In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Mike Huey, founder of Scalable Sales Solutions and a sales veteran with 30 years of experience building, breaking, and rebuilding sales organizations from coast to coast. Mike has taken companies from founder-led sales to national scale, including growing a seven-employee facility services business into a nationwide operation and today he helps business owners get the sales hat off so they can build something that runs, grows, and eventually sells without them. Patrick and Mike dig into the exact system that attracts A-player salespeople (and why hiring from inside your own industry almost guarantees you a B or C player), the compensation structures that actually drive new business instead of rewarding the wrong behavior, and the five sales metrics every owner should be tracking. They also cover the recruiting trick Mike uses to screen hundreds of applicants down to true A players, why you have to be willing to fire your top performer over a values violation, and how to know when your business is truly ready to scale or sell. Whether you're stuck as the bottleneck in your own company or preparing for an exit in the next five years, this conversation is a blueprint for turning a personality-driven business into a transferable asset. Key Takeaways: * If your business can't grow without you personally closing every deal, you own a high-paying job, not a transferable asset * A-player salespeople are attracted by five things: a sales playbook, a lead generation system, a CRM everyone uses, scorecards and accountability, and a compensation plan that rewards the right activities * Hiring salespeople from within your own industry usually lands you B and C players, true A players won't leave a strong book of business * Compensation plans should adjust every year; stairstep and hurdle models push reps toward new accounts, new territories, and new products * Track five metrics: sales activity, average deal size, close rate, repeat purchase rate, and referral rate * Culture comes down to two things, the right scorecards and core values and you must be willing to fire top performers over value violations * A business is only ready to scale when it cash flows completely with the owner stepped out of the process * Start exit planning long before the emergency: "life after the business" is one of the biggest reasons deals fall apart * This week's action step: identify the two or three things you're doing that hold the company back, and build a plan to offload them Learn More About Mike: * Mike Huey's website / consultation: mikehuey.com [mikehuey.com] * Leadership Blueprint: Accountability in Action by Mike Huey [https://www.amazon.com/dp/B0F6NNJFS2?lv=shuf&channelId=520&plpRedirect=mhFallback] * The Art of War for Business by Mike Huey [https://www.amazon.com/Art-War-Business-Leaders-Executives/dp/B0GS2Y3N16/ref=sr_1_1?crid=24CH2HIYCVL62&dib=eyJ2IjoiMSJ9.0fVrK25PwBkgrYpAqwD1q4iVQMxuHN5N33NcxTg0ldH4v8BWl8E-6pobs0BDfuwYIu-qtC95l_QwxT28SW2CGM8v5fE9x3OzuGtwt-NXq6WvkGMpIhzjgMGOkX95B3Iw7Ncy3YhhpYRXwOY0brhk3xGR1ogf9aW6l2k3hKWvj2r6_4cS3iziNg4z2yUFqdB3LrbLYtXUV6E5L5j1rb0WCTa8M_oaNLbxyBB01oxag5s.uqMi3qrz555rjDRdMuHKOxadbmvNIO3bf6WD0xi3NyE&dib_tag=se&keywords=The+Art+of+War+for+Business+by+Mike+Huey&nsdOptOutParam=true&qid=1783357736&s=books&sprefix=the+art+of+war+for+business+by+mike+huey+%2Caps%2C243&sr=1-1] * Make Your Company Scalable and Saleable by Mike Huey [https://www.amazon.com/Make-Your-Company-Scalable-Saleable/dp/B0DPKF2N8G/ref=sr_1_1?crid=JZ83EN4E85EK&dib=eyJ2IjoiMSJ9.r65y8n2WrZVtlqLCdvkv1ge9TJYrWG8DHqGAp5uOj1XGjHj071QN20LucGBJIEps.fDFlXEd2f5hSubZfEWtt-zZac7n3NuO2oVaCJNhhfB8&dib_tag=se&keywords=%E2%80%A2+Make+Your+Company+Scalable+and+Saleable+by+Mike+Huey&nsdOptOutParam=true&qid=1783357767&s=books&sprefix=make+your+company+scalable+and+saleable+by+mike+huey%2Caps%2C232&sr=1-1] Resources:    * Visit vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      * Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/] * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

138 | 83% of Businesses Fail Because of This… Here's How to Make Sure Yours Doesn't with Gretchen Roberts

What would it look like if your business finally stopped bleeding money through taxes, messy books, and financial blind spots and instead became the wealth-building machine it was always meant to be? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Gretchen Roberts, CEO of Red Bike Advisors, a national tax, accounting, and advisory firm that has helped hundreds of business owners improve financial performance, reduce taxes, and build long-term wealth since 2009. Gretchen brings a rare combination of deep financial expertise and an operator's mindset as a multi-time entrepreneur herself, making her advice as practical as it is powerful. Whether you're drowning in disorganized books or already running a profitable business and looking to keep more of what you earn, this conversation delivers a clear roadmap for getting from financially stressed to financially free. Gretchen walks Patrick through her firm's proprietary SOAR Framework - Stabilize, Optimize, Accelerate, and Retire; a four-stage journey designed to take business owners from financial chaos to tax-efficient wealth creation. From cleaning up years of messy books and benchmarking profit margins against industry standards, to building a 10-year tax savings blueprint and creating a business that can run without you, this episode is packed with actionable strategies that apply no matter where you are in your entrepreneurial journey. Gretchen and Patrick also dig into cash flow planning, the danger of reactive tax decisions, and what it truly means to be "financially retired", not just done working, but free to choose. This is a must-listen for any entrepreneur who wants to build a business that funds the life they actually want. Key Takeaways: * Messy books are more common than you think and you can't grow, optimize, or sell a business without a clean financial foundation * The SOAR Framework (Stabilize, Optimize, Accelerate, Retire) gives business owners a clear, stage-by-stage path from financial disorganization to wealth creation * 83% of businesses fail due to cash flow problems, building a cash cushion of 3–6 months is a critical protection strategy * Your P&L is a management tool - knowing how to read it and track trends month-over-month can help you spot problems before they become crises * An S Corporation election is often the lowest-hanging fruit for tax savings, opening up significant self-employment tax reduction year after year * Tax strategy must fit your cash flow reality, a great strategy on paper can cause serious problems if it drains liquidity at the wrong time * Exit-readiness starts long before you're ready to sell, if the business can't run without you, it's not ready for the market * "Financially retired" doesn't mean stopping work, it means having the freedom to choose your role and step back from daily operations Learn More About Gretchen: * Official Website: redbikeadvisors.com [redbikeadvisors.com]  Resources:    * Visit vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      * Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/] * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

137 | How Entrepreneurs Use Real Estate to Build Wealth Without Becoming a Landlord with Chris Larsen

What if your business is generating great income but you're still not financially free? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Christopher Larsen, founder and Principal of Next-Level Income, to tackle one of the biggest blind spots entrepreneurs face, building income without building lasting wealth. Chris brings over 20 years of real estate investing experience, an MBA in Finance, and a track record of over $2 billion in real estate acquisitions to the conversation. He walked away from an 18-year career in the medical device industry because he built something better, and now he dedicates his time to helping other entrepreneurs do the same. If you've ever wondered whether you're truly building wealth or just generating a bigger paycheck, this episode was made for you. Patrick and Chris break down the exact framework entrepreneurs need to achieve real financial freedom, including Chris's DIAL method for evaluating investments, the 7-year formula for replacing active income with passive income, and why owning a duplex is not the passive income strategy most people think it is. They also get into the power of real estate cycles, how to use depreciation to legally reduce your tax burden, and the generational wealth strategies that separate the Rockefellers from the Vanderbilts. Whether you're just starting to think about investing outside your business or you're ready to scale your portfolio, this conversation will challenge the way you think about money, freedom, and legacy. Key Takeaways: * Financial freedom is not a net worth number, it's the point where your passive income exceeds your monthly expenses * The DIAL framework helps investors identify what matters most: Depreciation, Income, Appreciation, and Liquidity * Owning small residential rentals is rarely passive, true passive income comes from partnering with an experienced operator * Real estate follows an approximately 18.5-year cycle, knowing where you are in that cycle determines which asset class makes the most sense * Buying the real estate your business occupies creates a powerful tax and wealth-building strategy * Diversification is critical, don't concentrate all your wealth in your business alone * Liquidity planning is non-negotiable, always maintain a minimum cash threshold to protect against black swan events * Teaching your children about money early and giving them real financial responsibility, is the foundation of generational wealth Learn More About Chris: * nextlevelincome.com * nextlevelincome.com/financialfreedombook * nextlevelincome.com/kids Episode Resources: * The Simple Path to Wealth by JL Collins [https://www.amazon.com/Simple-Path-Wealth-Revised-Expanded/dp/B0DQJMVM59/ref=asc_df_B0DQJMVM59?tag=bingshoppinga-20&linkCode=df0&hvadid=80264559055743&hvnetw=o&hvqmt=e&hvbmt=be&hvdev=c&hvlocint=&hvlocphy=93688&hvtargid=pla-4583864042563249&psc=1&hvocijid=12259141047151673049-B0DQJMVM59-&hvexpln=0] * The Secret Life of Real Estate and Banking [https://www.amazon.com/Secret-Life-Real-Estate-Banking/dp/0856832634/ref=asc_df_0856832634?tag=bingshoppinga-20&linkCode=df0&hvadid=80264559055743&hvnetw=o&hvqmt=e&hvbmt=be&hvdev=c&hvlocint=&hvlocphy=93688&hvtargid=pla-4583864043871633&psc=1&hvocijid=865586334049621129-0856832634-&hvexpln=0] Resources:    * Visit vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      * Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/] * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien