Independence by Design™

Ryan Tansom
  • 4.9 (37)
  • ENTREPRENEURSHIP

Independence by Design™ is a framework to help owner-operators get out of the weeds and lead from the boardroom. I built it because I lived this trap. In 2009, I joined my dad in our $21M family business. We turned it around and sold it for eight figures in 2014 — enough to pay off debt, cover taxes, let my dad retire, and leave me with a chunk of cash at 27. But the sale gutted our team, systems, and identity. It looked like a win, but it didn’t feel like freedom. I bawled in the driveway. After 450+ interviews, thousands of owners, and multiple ventures, I saw the real issue: we didn’t know the difference between being owners and operators. Our goals weren’t aligned. And we had no framework to guide us. That’s why I built iBD — to help owners avoid regret, reclaim their time, grow real equity value, and build a business that gives them freedom — whether they stay, scale, or sell. This show is the one I wish I had.

  1. 1D AGO

    #476: Tom Shipley | Why Most Owners Get Stuck at $1–$2M EBITDA (and How to Break Through)

    This conversation with Tom Shipley goes far beyond “growth” or “M&A tactics.” It’s about understanding the real game of ownership — how value is actually created, how capital really works, and why most owners unknowingly trap themselves by optimizing the wrong things.  We start by reframing business as a finite game of time, energy, and capital. Tom shares how his background in Special Forces shaped his approach to leadership, resourcefulness, and decision-making — and how those principles carried into building, acquiring, and ultimately selling businesses.  From there, we go deep into the mechanics most owners never truly understand: valuation, EBITDA vs. cash flow, multiple expansion, acquisition strategy, and deal structure. Tom breaks down how value is created before the exit, why fundamentals matter more than hype, and how acquisitions can create real wealth — or destroy it — depending on how they’re done.  We end with one of the most important insights in the episode: the “valley of despair” facing owners with $1–$2M EBITDA, and Tom’s merge-to-exit model designed to help founders escape it by building scale, optionality, and alignment before they sell.  Tom Shipley is a serial entrepreneur and M&A expert with 20+ years scaling brands to $2B+ in sales via D2C, Amazon, and retail giants like Costco and Ulta. A "lone soldier" in Israel's elite IDF Unit 669, he bootstrapped Atlantic Coast Brands to $100M (exited 2021), raised $100M for Foundry (e-com aggregator), and founded AVA Acquisitions for digital agencies. Now, via Deal Boardroom and bi-annual DealCon Summit, he empowers founders to acquire, scale, and exit—often with $0 down. Host of Deal Playbook podcast, Shipley splits time between Austin and Tel Aviv, mentoring hyper-growth via Shipley Capital.  Top 10 Takeaways  Ownership is a finite game — time, energy, and capital are limited, so priorities must be chosen deliberately.  Great leaders optimize for resourcefulness, not resources, especially when conditions get constrained.  EBITDA and cash flow serve different purposes: cash is survival, EBITDA is valuation.  Revenue growth without fundamentals often destroys value instead of creating it.  Valuation is ultimately about confidence in future cash flows, not past performance.  Multiple expansion is one of the most powerful — and misunderstood — wealth creation tools in business.  Acquisitions create value only when they are strategically complementary, not just additive.  Poor integration turns acquisitions into “Frankenstein” businesses that collapse under complexity.  Most $1–$2M EBITDA owners are stuck in a no-man’s land where selling doesn’t deliver real freedom.  Merging before exiting can dramatically increase the probability, multiple, and outcome of a successful sale.    Chapters:   (00:00) Introduction of Tom Shipley and discussion of acquisition strategies  (02:37) Finite resources require prioritizing impact, adventure, and resourcefulness  (07:10) Writing your own epic novel with five-year chapters  (09:40) Buying businesses without cash using creative deal structures  (12:16) Special Forces lessons on resourcefulness, tenacity, and team leadership  (21:30) Valuation fundamentals and confidence in future cash flows  (35:00) Multiple expansion and compounding value through strategic acquisitions  (43:32) Strategic fit and avoiding Frankenstein rollups in acquisitions  (55:13) Integration work upfront generates cash flow versus Frankenstein EBITDA  (58:36) Where to find Tom Shipley and information on Dealcon    Resources:  Tom Shipley LinkedIn: ... Chapters (00:00:00) - Independence by Design: Value of Acquisitions(00:02:03) - Tim Ferriss on Value and Time(00:06:12) - In the Elevator With Tom Cruise(00:09:40) - How to Buy a Growing Business(00:11:45) - Tom Clancy on His First 18 Year Journey(00:13:16) - Leaders: Next Chapter(00:17:12) - Steve Jobs on Valuation and His Own Experience(00:23:16) - What Do You Look At In Due Dilution?(00:24:15) - When I'm trying to sell my business,(00:26:44) - Brad Buster(00:31:26) - On The Cost of Capital(00:34:50) - Adjusted EBITDA vs Cash Flow(00:35:57) - Multiple Expansion(00:37:52) - Acquisitions and the Value of Your Business(00:40:42) - Jeff Bezos: The End of Building a Good Business(00:43:12) - Acquisitions Made With a Long Term View(00:49:01) - Have We Got The Right Strategy for the Future?(00:51:20) - How to Buy a Successful Business with a Long Term View(00:56:09) - The Value of Multiple Acquisitions(00:57:03) - Employee Stock Ownership Plans(00:58:33) - Dealcon 2012

    1 hr

  2. JAN 8

    #475: Matt Paulson | $50M & 20 Employees; Designing a Business You Never Want to Sell

    Matt is the founder of MarketBeat, a financial media company he’s built quietly over 19 years into a ~$50M/year business with around 20 employees — and what makes this episode special isn’t just the scale, it’s how he’s designed the business and his life around it. We talked about focus, attention, hiring, valuation discipline, resisting hype cycles, and why keeping the business can often be the most profitable move an owner can make.  We also unpacked the realities most people never see: what it actually takes to build leverage without blowing up the mothership, how to think clearly about valuation and selling, how AI really fits into the future of work, and what happens after you cross financial independence. This episode is about designing ownership — not chasing exits, headlines, or noise.  Matt Paulson is the founder of MarketBeat, a financial media company he’s grown over 19 years into a ~$50M annual business. He also runs Homegrown Capital, a Midwest-focused venture firm with ~$40M under management. Known for his disciplined approach to growth, valuation, and hiring, Matt focuses on building durable businesses, developing high-caliber teams, and designing work around a meaningful life beyond the balance sheet.  Top 10 Takeaways  Focus works when the owner owns the few things they are uniquely great at and delegates everything else.  Over-optimizing a healthy business often does more damage than thoughtful restraint.  The best businesses allow safe experimentation without risking the core cash-flow engine.  Most owners misunderstand valuation because they confuse effort, emotion, and market reality.  Selling a business is often driven by burnout, not strategy — and that distinction matters.  Financial freedom changes decision-making more than most people expect.  AI will reward operators who understand fundamentals, not replace them.  Strong teams are built by upgrading competence only when the business is ready for it.  The most valuable skills in the future are the ones that can’t be automated.  The “good old days” aren’t behind you — they’re happening right now if you’ve designed the margins to see them.    Chapters:   (00:00) Matt Paulson and his unexpected consulting success   (08:34) Managing attention, avoiding distractions, and setting boundaries with community involvement  (11:31) Overcoming FOMO and learning to say no to opportunities  (14:59) Delegating what you don't want to do and building systems  (19:58) Hiring great people and making MarketBeat a premier employer brand  (26:07) Homegrown Capital's venture investment thesis and evaluating startups  (37:41) Why Matt turned down acquisition offers and chose to keep MarketBeat  (40:24) Managing wealth, teaching kids about money, and charitable giving  (54:11) Being authentic versus content creation and avoiding labels in business  (59:10) Setting goals, living in the present, and thinking about succession planning  (1:08:14) Email marketing expertise and managing six million subscribers at scale    Resources:  https://www.marketbeat.com/  Matt Paulson LinkedIn: https://www.linkedin.com/in/matthewpaulson/  Ryan Tansom Website https://ryantansom.com/    Chapters (00:00:00) - Independence by Design(00:01:34) - How I Made Six Figures on My X-Feed(00:02:56) - PODCAST: Sharon on Starting a Media Business(00:04:46) - Bob O'Donnell on His Focus at 40(00:07:22) - Staying Focused on MarketBeat(00:09:27) - Meeting the Tradeoff Between Attention and Time(00:14:15) - Exercising Flexibility on the Business(00:17:23) - In the Elevator: Hiring a Team(00:19:03) - Marketing at MarketBeat: The Right People(00:22:25) - Have You Had Any Partners Leave MarketBeat?(00:23:59) - Real Estate and VC Valuations(00:26:39) - What's the Investment Value of Homegrown Companies?(00:28:11) - How To Pick The Right Tech Company(00:29:46) - Will AI Disrupt The World?(00:33:04) - Are You Seeing This In Your Pitches?(00:35:32) - Beat: I Didn't Sell My Business(00:40:06) - How to Teach Money to Your Child(00:43:43) - Matt Maher on Donor's Money(00:45:45) - Does a Christian Businessman Need a Board?(00:51:20) - Matt Walsh on the Need for Labels(00:56:04) - Want to Win Next Year? Here's Your List(00:58:36) - Letting Go of the Operations(01:00:56) - Does My Estate Need an ESOP?(01:03:30) - How to Reach 6 Million Subscribers in 2020(01:05:16) - How Many Companies Have an Email List as Big as Yahoo Finance's(01:07:35) - Markbeat: Building Relationships With Subscribers(01:08:31) - Interviewing With AI

    1h 10m

  3. JAN 1

    #474: Luke Maupin | How to Flip the Power Dynamic with Your Commercial Bank

    Most owner-operators have a complicated relationship with their bank — part dependence, part frustration, and very little transparency. I’ve lived that reality myself, and I know how powerless it can feel when decisions are made “behind the curtain.”  In this episode, I sat down with my longtime friend and commercial banker, Luke Maupin, to pull that curtain back. We walk through how banks actually make money, how credit decisions really get made, why some owners get easy access to capital while others get boxed in, and how much of this comes down to planning, storytelling, and preparation — not luck.  This conversation is about flipping the power dynamic. When owners understand the banking business model, bring a clear financial narrative, and know which questions to ask, banks stop being adversaries and start becoming tools. The goal isn’t cheaper money — it’s optionality, confidence, and control over your future.    Luke Maupin is a commercial banker with nearly two decades of experience across large national banks and community institutions. Known for advocating for owner-operators inside the banking system, Luke specializes in credit strategy, growth financing, and helping businesses align capital structures with long-term plans. He brings uncommon transparency to how banks operate and how owners can navigate lending relationships with confidence.  Top 10 Takeaways  Banks are businesses first, and their balance sheet health directly impacts your access to capital.  Most lending decisions are driven by risk allocation and capital reserves, not personal relationships.  A banker’s real job is to be a storyteller for your business inside the credit department.  Owners should ask the same hard questions of their bank that banks ask of them.  Deposit composition, portfolio concentration, and liquidity matter more than headline interest rates.  A three-statement financial forecast is the strongest leverage an owner can bring into a banking relationship.  Covenants, not rates, are usually what restrict owner freedom the most.  Personal guarantees are negotiable, especially when tied to clear performance milestones.  The right debt structure depends on timing, cash conversion, and growth visibility — not rules of thumb.  Owners who can clearly show when effort turns into cash regain control of financing conversations.    Chapters:   (00:00) Introduction, Luke Maupin - from touring musician to commercial banker  (05:50) Banking transparency: asking banks the same questions they ask you  (14:38) How banks operate: deposits, liquidity, and the business model  (37:30) How banks make money: lending margins, fees, and treasury management  (44:34) Business banking versus middle market: understanding customer segmentation  (56:00) Cash flow mastery and why three statement projections matter  (1:00:17) Credit approval process: understanding who makes the final decision  (1:19:41) Covenants and distributions: negotiating terms that don't strangle growth  (1:33:18) Personal guarantees: strategies for negotiating and eliminating recourse debt    Resources:  Lucas Maupin LinkedIn: https://www.linkedin.com/in/lucas-maupin-0501b428/  Ryan Tansom Website https://ryantansom.com/ Chapters (00:00:00) - The Best Way To Flip The Power Dynamic With Your Commercial Bank(00:01:47) - Luke Map on Why He's on the Podcast(00:04:44) - Bradley on Owning a Bank(00:08:55) - Banking Still a Business(00:10:10) - Does Basel III Impact Community Banks?(00:12:03) - Capital allocation and risk assessment(00:14:29) - How Do Banks Make Money?(00:16:45) - Business Talk: Cost of Funds(00:17:23) - Deposit vs Lending Ratio(00:23:22) - Is Loan Demand More Than Deposit Demand?(00:23:59) - Banks: Where Does the Money Come From?(00:27:35) - The First Measure of a Bank's Aggressive Lending(00:36:41) - How the Banks Make Money(00:37:51) - TREASURE Management: Can a Bank Be a Software Company(00:44:19) - Business Banking vs. Commercial Banking: What's the Difference?(00:47:09) - Financial Services Partner Stories(00:51:56) - Bradley: On Debt Financing(00:55:43) - How Many Business Owners Have a 3-Step Cash Flow Forecast(00:59:58) - Who's Actually Making the Credit Decision?(01:01:53) - Bradley: On the Bank Experience(01:09:43) - Basic Advance Rates and Marginal Lending(01:12:12) - Banking Executive: Cash Flow Forecast(01:17:02) - When Shopping for a Bank Covenants(01:22:02) - Pre- and Post-Distribution Covenants(01:24:46) - Do You Need a Bank to Financially Support an Acquisition?(01:26:43) - Risk of Leverage in Companies(01:28:38) - Bradley: Leverage and Cash Flow(01:32:54) - Private Debt Structures, Leverage(01:38:27) - Personal Guarantees--Challenging Your Bank(01:41:59) - Private Equity Money: Leveraged Bank Financing

    1h 47m

  4. 12/25/2025

    #473: John Bartlett | What Selling a Business Really Looks Like

    Most owners don’t wake up wanting to sell their business. They wake up tired, overloaded, and unsure how much longer they can keep doing everything themselves. In this conversation, John Bartlett and I start by unpacking that reality — the moment when success on paper doesn’t feel like freedom, and selling starts to feel like the only option.  From there, we zoom out and talk about what’s really going on beneath the surface: phantom wealth, misunderstood cash flow, and why many owners don’t actually see the full set of options available to them. We talk about how value is created, what actually drives multiples, and why clarity around cash flow and owner dependency changes everything.  Only after that foundation is set do we walk through the real process of selling a company — what actually happens when you go to market, how deals are structured, how long it takes, where owners get surprised, and why the headline price is often the least important part of the transaction. This episode is about helping you see the whole landscape clearly — so whether you build, transition, or sell, you’re making an intentional decision instead of reacting out of exhaustion.    John Bartlett is the founder of Brentwood Growth, where he helps owner-operators navigate valuation, growth, and M&A decisions with clarity and realism. A former serial entrepreneur, John grew and sold multiple businesses before becoming an advisor to lower middle-market owners. His work focuses on turning companies into durable assets—whether that means scaling, de-risking, or exiting on aligned terms.  Top 10 Takeaways   Most owners don’t want to sell their business — they want relief from carrying everything themselves.  Phantom wealth is common: businesses look valuable on paper but don’t produce real freedom or liquidity.  Enterprise value is driven by adjusted EBITDA and the confidence buyers have in future cash flow.  Owner dependency is one of the biggest value killers, even in otherwise strong businesses.  Selling is not a moment — it’s a long, demanding process that reshapes the owner’s life for months or years.  Deal structure (taxes, earn-outs, rollover equity, timing) often matters more than the headline price.  Most owners dramatically underestimate how long a real M&A process takes and how consuming it is.  Buyers pay for predictability, not potential, and confidence in cash flow determines the multiple.  Owners who wait until burnout have fewer options and less leverage than they realize.  The best outcomes happen when owners understand their options early and choose intentionally, not reactively.  Chapters:   (00:00) Making a meaningful difference in business owners' lives and transitions  (06:08) Three categories of sellers: burned out, transitioning, and scaling  (10:40) Life as jigsaw puzzle: balancing financial and lifestyle goals  (25:45) What owners really want is work-life balance and control  (36:10) Valuation process: determining current worth and future potential value  (46:10) Valuation fundamentals: adjusted EBITDA and multiple determine enterprise value  (01:01:40) Complete M&A process timeline from teaser to final offers  (01:10:10) Marathon hydration analogy: plan your exit before you're exhausted  (01:14:00) Quality of earnings: the detailed due diligence cavity search  (01:26:20) Critical difference between gross sale proceeds and after-tax reality  (01:28:33) Lock business down within twelve months of planned sale    Resources:  John Bartlett LinkedIn: https://www.linkedin.com/in/johnl... Chapters (00:00:00) - Independence by Design: Selling Your Company(00:01:55) - Why Business Owners Should Sell Their Companies(00:05:59) - Owners in Their 60s, 70s Should They Sell the(00:12:41) - Ownership: The 7 Levels of Growth(00:20:24) - Jack Stack on Ownership at 82(00:22:26) - Ownership vs Operator: The Problem(00:24:48) - Owner Operator Bifurcation(00:32:05) - Steve Ballentine on the Value of the Business(00:35:35) - Exploring the Value of the Business(00:43:30) - How to Win with a Size Client(00:43:49) - Private Equity Brokers: Enterprise Value of Companies(00:45:05) - Exploring the Multiple of a Private Business(00:50:43) - Adjusted EBITDA Multiple(00:57:55) - How To Find a Buyer for Your Startup(01:02:32) - Have You Validated Any Offer?(01:05:26) - Part 6: Hydration(01:11:09) - The Offer for the Business(01:15:01) - Do Over 80% of Deals Get Sold?(01:17:55) - Does an Earnout Make a Bonus?(01:27:02) - Should You Do a Significant Deal?

    1h 29m

  5. 12/18/2025

    #472: Ryan Tansom | The Only Financial Model You Will Ever Need

    Most owners make decisions in the dark. Sales over here, payroll over there, cash flow somewhere in the background — and no clear way to see how it all fits together. Watch on YouTube In this episode, I break down the 5-year, three-statement model I use with clients to finally show how revenue, margins, OpEx, working capital, cash flow, and valuation all connect. It's the system that turns guessing into clarity, scattered decisions into strategy, and helps you design a business that aligns with your goals for time, cash flow, and long-term wealth. When owners finally see the whole picture — how their decisions drive EBITDA, how working capital eats cash, how valuation is created, and how comp and accountability align to their goals — they gain the ability to run the company from the boardroom instead of the weeds. I know what it's like to feel trapped in the grind of running a business. In 2009, I joined my family's $21 million company during a financial crisis, and over five years, we turned it around and sold it for eight figures. While that sale looked like a win on paper, it left me questioning everything. The stress of running the business, the massive tax hit, and the lack of clarity about how our decisions aligned with our goals taught me a powerful lesson: most business owners don't have a framework to make decisions that lead to true freedom. That's why I created the Independence by Design™ Ownership Framework. It's a system to help owner-operators align their business decisions with their goals for time, cash flow, and wealth. Over the last decade, I've been a part of dozens of transactions and worked with thousands of business owners, helping them design businesses that work for their lives—not the other way around. On the podcast, I share strategies and insights I've learned along the way, bringing in top thought leaders like Gino Wickman, Mike Michalowicz, Jack Stack, and Bo Burlingham to provide their perspectives. Whether you're feeling stuck, planning to scale, or preparing for an exit, my goal is to give you the tools and confidence to take back control and build a life you love. This isn't just another business podcast. It's about reclaiming your independence and designing a business that gives you the freedom you deserve. Top 10 Takeaways Your ownership goals must drive the business model — not the other way around. A business is a system — and the three statements show the whole system at once. Valuation is not a mystery — it’s predictable math tied to cash flow. The "valuation gap" determines whether your dreams are mathematically possible. Revenue must be predictable — and that requires a mapped customer journey and measurable funnel. Margins are an operational scorecard — not just accounting output. Working capital is the silent killer — and explains why the bank balance never matches the P&L. The cash flow statement is the bridge between ownership and operations. Comp plans must be tied to the model — aligning the team around revenue, margin, EBITDA, and cash. The model is the owner’s decision engine — allowing them to elevate into the boardroom. Chapters: (00:00) Why ownership goals must drive your business model: time, cash and wealth (04:22) The valuation gap tab: understanding enterprise value and equity value (09:30) Projections: building your five-year revenue and growth assumptions (13:00) Revenue forecasting: line of busi... Chapters (00:00:00) - Independence by Design(00:01:51) - Why Your Own Money Is SO Important(00:09:37) - Out Year Projections(00:17:42) - Adjusted EPS and normalized EBITDA(00:19:09) - The Earnings Statement, Cash Flow Statement(00:26:38) - Distributions and Cash Flow(00:33:44) - The Sales and Marketing Journey(00:38:53) - The 3-Step Process for Operations(00:45:58) - The Business Valuation Model(00:49:20) - The Income Statement Comparison and Budget Comparison(00:51:39) - Exporting the Trial Balance from Cash Flow(00:57:40) - Grow Your Business With a Fear of the Future

    1h 2m

  6. 12/11/2025

    #471: Tyler LaFleur | Stop "Playing" With AI

    You hear the hype about AI every day, but when you try to use it, it feels like a toy rather than a tool that can actually help you reclaim your time. Watch on YouTube In this episode, I’m cutting through that noise with Tyler LaFleur, a former nurse and functional medicine practitioner turned Fractional COO. I brought Tyler on because he doesn’t look at business through the lens of "growth at all costs." He uses first principles thinking—the same diagnostic approach used in medicine—to find the root cause of what is keeping you stuck in the day-to-day. We have a candid, practical conversation about why most business owners fail with AI because of "lazy prompting," and why Artificial Intelligence is useless without "Objective Truth." If you don’t have your financial constraints and ownership goals clearly defined first, applying AI is just pouring rocket fuel into a car with no steering wheel—you’ll just hit the wall faster. Top 10 Takeaways First Principles Thinking: Just like in functional medicine, you must strip a business down to its core mechanics to find the root cause, not just treat the operational symptoms. The "More" Trap: When an owner lacks a definitive financial goal, the default strategy becomes a chaotic, exhausting pursuit of "more" revenue without more freedom. AI Needs Constraints: AI is a rocket ship, but it needs a rudder. Without the "Objective Truth" of your financial model and ownership goals, AI will hallucinate a path to nowhere. Visionary vs. Integrator: Visionaries are great at starting fires but terrible at putting them out. AI can act as the "Integrator" that documents processes and executes the details you hate. Don't Automate a Mess: Before building complex agents, start with "low-hanging fruit"—the repetitive administrative tasks that steal 6-10 hours of your time every month. Lazy Prompting: The reason AI "doesn't work" for most owners is that they treat it like Google. You must give it deep context (your strategy, constraints, and voice) to get boardroom-level output. Claude vs. ChatGPT: For business owners, Tyler recommends Anthropic’s Claude because its "Projects" feature allows you to upload your entire operating system as context. Cleaning Financial Data: You can teach AI a "Skill" (like cleaning a messy trial balance or categorizing expenses) by simply showing it a transcript of you doing it once. The "Ladder on the Wrong Wall": AI will help you execute a bad strategy faster. Efficiency is useless if it’s driving you toward a business model you hate. Just Start: You cannot break the AI. The biggest risk to your business isn't AI taking over; it's your competitor using it to move twice as fast while you wait for it to get "easier." Tyler LaFleur is a Fractional COO and AI integration specialist who helps visionaries escape the weeds. A former nurse and functional medicine practitioner, Tyler bridges the gap between biological systems and business operations, using "first principles" to diagnose and cure operational bottlenecks. He specializes in practical AI application—moving beyond the hype to build custom agents, automate workflows, and clean financial data using tools like Claude and ChatGPT.  Chapters:  (00:00) Tyler's journey from nursing to fractional COO to AI integration (06:23) First principles thinking applied to healt... Chapters (00:00:00) - Independence by Design: First Principles Thinking(00:02:59) - How to Lead an AI-Driven Company(00:06:01) - Nurses vs Business: What's The Connection?(00:08:11) - How Functional Medicine Became Outcome Driven(00:13:53) - Learning From the Pros(00:15:14) - Leadership Made Easy(00:20:32) - Dr. Thayer: I Interrupt My Guests(00:20:56) - The First Principles of Business in AI(00:28:09) - Steve Ballentine on Goals and the Process(00:32:41) - Board of Directors: The Cash Flow constraint(00:37:47) - The Objective Reality of Spending(00:42:21) - How to Manage Your Business's Financials(00:46:00) - Multiple Valuation For Small Businesses(00:47:49) - Steve Jobs on Strategic Planning, Sales and Marketing as Silos(00:53:59) - How To Manage a High Cost Business(00:54:23) - How To Build Your Business on the Wrong Wall(01:00:46) - Analytical Data Analysis with ChatGPT and Anthropic Squad(01:04:34) - Gemini 3.0 vs. OpenAI: The Best(01:06:57) - How to Use AI in Your Company's Business(01:11:09) - Building a social network with AI(01:17:42) - Beyond the Prompts: Chat(01:23:41) - How to Build a Business with AI?(01:27:47) - What's The Barrier to AI in Business?(01:33:11) - On Automation and the Future of Business(01:40:13) - Tyler the Creator on Less Needing His Business

    1h 42m

  7. 12/04/2025

    #470: Greg Meredith | Strategic Planning vs. Strategy

    In this episode, I sit down with Greg Meredith, founder of Simply Strategic, to distinguish the crucial difference between having a strategic plan and actually possessing a strategy. We dive deep into Greg’s "9 Keystones" Simply Strategic framework, exploring how companies can identify their unique "Winning Position" on the battlefield of business. Greg explains why true strategy requires painful trade-offs, the importance of the "Opposite Rule" in decision-making, and how to successfully integrate high-level strategy into a daily business operating system for long-term execution. Watch on YouTube Top 10 Takeaways Strategy vs. Planning: Planning is the process, but the goal is a specific "Winning Position" on the competitive landscape. The Opposite Rule: If the opposite of your strategy looks ridiculous (e.g., "we give bad service"), you haven't made a real choice. The Power of Trade-offs: You cannot say "yes" to what matters most without aggressively saying "no" to other opportunities. Pick Your Hill: Companies usually win on one of five hills: Singular, Integrated, Preferred, Potent, or Scaled True Company Assets: Real assets aren't just on the balance sheet; they are the rare or "unmatchable" capabilities competitors can't copy. The Bullseye: Define success multi-dimensionally: set specific targets for culture, operations, and clients, not just revenue. Embrace the "Messy Middle": High-trust teams must fight through tension and disagreement to reach true alignment. 3 Phases of Strategy: A complete cycle requires three distinct phases: Prepare, Plan, and Persist. Progress Over Perfection: A 70% plan executed today is better than waiting indefinitely for a perfect strategy. Strategy Needs a System: A strategic plan is useless without a business operating system (like EOS) to ensure execution. Key Quotes "We start with this core definition of strategy is using company assets to create a high-impact winning position." - Greg Meredith "Can you define your strategy in such a way that a logical, savvy, even wise competitor would look at the opposite of your strategy and say, hey, that's viable, that's a good strategy." - Greg Meredith "Strategy is about intentionally saying, we're gonna go there, we're gonna hold that ground, we're gonna win from that place."- Greg Meredith "It's about trade-offs... You have to say no if you're really gonna say yes to the things that are most important."- Greg Meredith "It's gravity, it's not earthquakes... We want to put in that consistent pull. Here's where we are, here's what we're working on, not we're going to have this one-time event that's going to shake everything up."- Greg Meredith Greg Meredith Greg Meredith is the founder of Simply Strategic, a consultancy dedicated to helping small and mid-sized businesses ($2M - $500M revenue) build and execute actionable strategic plans. With a background in private equity and over 75 strategic engagements, Greg guides leadership teams through his "9 Keystones" framework. He focuses on helping owners define their "winning position," leverage unique company assets, and transition from planning to persisting, ensuring strategy integrates seamlessly with daily operations. Chapters (00:00:00) - Independence by Design: Strategic Plan with Greg Meredith(00:01:08) - Back to Strategic Planning With Dan(00:01:59) - What Strategic Planning Is Really All About(00:03:51) - The 3-Step Process of Strategy(00:06:19) - What is a Strategic Plan and How to Win?(00:09:31) - Ownership Operating System vs Strategy(00:12:23) - Management: Say No to Everything(00:14:50) - The Opposite Rule in Strategy(00:19:06) - Mutual Funds and Expanding Their Business(00:24:55) - The Trust Factor in a Board Meeting(00:30:56) - President Trump on Handoff of the Ball(00:31:46) - The Winning Positions(00:34:17) - Quantum of Singularity: The Only Business with Access to Rare(00:40:29) - Importance of Scale in Building Products(00:42:03) - Three Winning Positions and None of the Others(00:44:09) - Executives: The Future of Connected Business(00:49:34) - Bradley: Strategic Planning, The 3 Phases(00:52:14) - The 3 Phases of Strategic Planning(00:55:18) - 9 Keystones of Strategic Planning(00:58:28) - Keystone 6(01:00:49) - What's The Most Valuable Idea in the Company?(01:05:42) - Importance of Core Beliefs in the Company(01:09:35) - The Process of Strategic Planning(01:13:02) - Company Assets and the Business Flywheel(01:19:00) - Steve Ballentine: The Bullseye(01:24:33) - Ownership Goals and the Operating System(01:31:19) - The Fitness Industry's 96%(01:31:54) - How to Build a Strategic Plan and Business Operating System

    1h 37m

  8. 11/27/2025

    #469: Alison Bechdol | Your Marketing Isn’t Broken — Your Data Is

    Marketing is confusing for most owners — not because the tactics don’t work, but because the data underneath is broken.   Watch on YouTube   In this episode, I sit down with Alison Bechdol, founder of Digital-ade, to break down why so many owners feel like they’re throwing money at marketing with nothing to show for it. And the truth is simple: you cannot build a predictable revenue engine without clean data, real attribution, and a clear picture of your customer acquisition cost. Most companies don’t have a marketing problem — they have a data infrastructure problem. Tracking is wrong, systems aren’t unified, and owners don’t have the visibility they need to design revenue, forecast cash flow, or make decisions from the boardroom.    We also talk through the deeper issue: the marketing industry’s incentives are misaligned. Owners need doers, not gurus — and they need a clear order of operations to diagnose, fix, and scale what actually drives margin and enterprise value.    10 Takeaways:  Most owners don’t have a marketing problem — they have a data problem.   If attribution isn’t accurate, every marketing dollar becomes guesswork.   The marketing industry runs on misaligned incentives that reward activity over outcomes.   Many “strategic” roles lack operational depth, leaving owners paying for insight without execution.   Most companies’ tools are misconfigured, creating blind spots in revenue-critical data.   Bad data kills owner confidence and leads to reactive, inconsistent decisions.   There is a clear order of operations: fix tracking → unify systems → measure → optimize → then scale.  Predictable revenue comes from diagnostics and visibility, not tactics or trends.  Clean data + a reliable conversion funnel = predictable CAC, forecastable revenue, and controllable cash flow.  Clear data empowers owners to make boardroom-level decisions and allocate capital with confidence.  Alison Bechdol is the owner of Digital-ade, specializing in analytics, tag management, event tracking, and paid media for both B2B and B2C companies. Known for cutting through noise and fixing the data foundations most businesses overlook, she helps owners build reliable tracking, clear attribution, and actionable insights. Alison also teaches GA4, KPIs, and Google Tag Manager through workshops, consulting, and speaking engagements.  Chapters:   (00:00) Alison's unconventional journey from event planning to analytics mastery  (05:45) First principles thinking and understanding consumer psychology in data  (12:37) Predictable revenue and mapping the complete customer journey  (15:37) Moving from mindset to implementation: where to start with data  (20:20) Setting goals and KPIs: working backwards from conversion points  (32:09) Building your dashboard: Looker Studio as single source of truth  (43:04) Why AI can't replace expertise: the insights problem explained  (56:00) Fractional resources and finding the right doers versus strategists  (1:12:37) Getting started today: implement tracking and identify conversion points  Rate, comment, and share with the owner/operators you know!  Resources:  Company Website http://digital-ade.com/  Ryan Tansom Website https://ryantansom.com/   Chapters (00:00:00) - Independence by Design: A Client Experience Dashboard(00:02:23) - Web Analytics: What's the Background for Everyone?(00:05:27) - WSJD Live: Exploring How Stuff Works(00:10:09) - Tim Ferriss: Predictable Revenue(00:15:41) - Pulling the financials out of the funnel(00:17:35) - How to Get Your Lead to Buy In(00:19:57) - How to Find the Right KPIs?(00:23:12) - KPI Planning: Starting at the Sales Stages(00:27:32) - How to Manage the B2B Sales Cycle(00:31:07) - Beyond GA4: Data & Analytics, Sales & Marketing(00:37:09) - WSJD Live: The Different Decisions Made by CRM and(00:38:15) - What are the Sales Stages? From Awareness To Mark(00:40:38) - Why We Can't Outsource Our GPTs(00:44:08) - How to Build a Trustful Lead(00:47:07) - Top 5 Percentimal KPIs(00:50:22) - Economic Cycles(00:57:03) - Some good people to read and learn about data analysis and analytics(00:58:22) - Why I Want You to Meet Kim Clark(01:03:59) - The Challenges of Marketing and Digital Marketing(01:05:03) - Optimizing for AI in ChatGPT(01:10:48) - Gainesville: How to start using GA4 Analytics in your

    1h 14m
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About

Independence by Design™ is a framework to help owner-operators get out of the weeds and lead from the boardroom. I built it because I lived this trap. In 2009, I joined my dad in our $21M family business. We turned it around and sold it for eight figures in 2014 — enough to pay off debt, cover taxes, let my dad retire, and leave me with a chunk of cash at 27. But the sale gutted our team, systems, and identity. It looked like a win, but it didn’t feel like freedom. I bawled in the driveway. After 450+ interviews, thousands of owners, and multiple ventures, I saw the real issue: we didn’t know the difference between being owners and operators. Our goals weren’t aligned. And we had no framework to guide us. That’s why I built iBD — to help owners avoid regret, reclaim their time, grow real equity value, and build a business that gives them freedom — whether they stay, scale, or sell. This show is the one I wish I had.

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