Podcast
The Winning Momentum Podcast with Scott Sinclair
Hosted by Scott Sinclair · EN
Winning Momentum is for business leaders, entrepreneurs, owner managers, related professionals and students of business. It is about improved business performance, leadership and crisis management. Turning negative momentum into positive momentum that, in turn, renews energy and passion, attracts resources, both human and financial, and relieves the destructive personal and family pressures that come with a struggling business. Winning Momentum content consists of three parts: 1. Leadership Skills: Because troubled businesses need leadership to change. 2. Mindset Development: Because troubled businesses are always limited by the personal habits and mental filters of its leaders. 3. Technical Skills: Because running out of money during a turnaround is not an option.
11episodes
Episodes
Newest firstAll episodes
Sinclair Range Week in Review — June 15, 2026
1w ago00:29:56Tap to summarizeDIP financing, the turnaround rule nobody likes, and an honest update on our own stuck real estate.Deals on the Go• DIP financing 101 — court-approved loans that rank ahead of everyone so a stalled company has the capital to change• Sapphire Global’s DIP on Sirona Pharma: $2.5M to stabilize, stay creditors, get relicensed — business now being sold• New client: a stalled $100M+ real estate development where a small DIP relaunches it and creates huge value• Lenders — the onus is on you to create these deals. Reach outLesson Learned: Capital Won’t Fix a Refusal to Change• Rule #1 of every turnaround: accept the need to change — before capital• The over-advance trap — we’ve seen a book 90% in over-advance, an equity-risk lender at debt rates• Equity version: throwing good money after bad — a client about to write off hundreds of millions• Don’t advance more without a price, and the price is change. Boots on the ground can’t be replacedStruggles: Living the Problem I Solve• Liquidity tied up in three key assets — two are environmentally-affected real estate• Both under firm contract; both buyers failed to close — now in litigation• The exact problem we solve for clients — just living the hard version ourselvesWhat I’m Thinking About: Go Where the Energy Is• 1-minute first-principles videos — ~50k views each, ~200k in two months, big engagement• Not partisan — my concepts in a framework. Canada needs winning momentum• The Inner Circle is coming back — relaunch soon#DIPFinancing #BusinessTurnaround #PrivateCredit #Restructuring #DistressedDebt #RealEstate #SinclairRange #WinningMomentum
Transcribe →Sinclair Range Week in Review — March 27, 2026
Mar 2700:32:05Tap to summarizeI went to Mexico. Came back sick. Still ran the show.This week at Sinclair Range: three live deals including a cannabis company exiting CCAA, a $100M private credit raise, and an active enforcement file. Plus — the one turnaround lesson that changes everything, a Docusign trap that nearly cost us eight figures, and how AI has taken over our entire operation in two weeks.Deals on the GoA cannabis producer in CCAA with $47M in hard assets and an imminent Health Canada licence reinstatement — seeking C$6M to exit restructuring and relaunch into medical and international markets. A Canadian private credit raise — a 26-year-old factoring lender raising up to $100M at 10% fixed quarterly, all first secured, targeting a $1.5B+ gap in the Canadian market. And a lender enforcing its security against a transport company — equipment being collected and sold in an orderly process.Lesson Learned: Admit You're in TroubleEvery turnaround starts with one thing: changing your frame. Stop calling it a rough patch. When you admit you're actually in trouble, the problem stops being emotional and becomes math. We cover the baseline valuation concept — what each stakeholder recovers if the business blows up today — and why that number is the foundation of every serious lender negotiation.Struggles: When the Plan Doesn't WorkThe Sinclair Range turnaround was built on selling two real estate assets worth well into eight figures. Neither has sold. One buyer refused to close and put a lien on title — now in litigation. The other buried a clause in a Docusign offer letting them extend the conditional period indefinitely. We caught it and got out — but the lessons are hard-won: in a turnaround, the plan that should work often doesn't. And never sign a Docusign negotiation without reading every word — or running it through AI first.What I'm Thinking About: AI Has Taken Over Sinclair RangeIn two weeks: investment agreements, capital raise documents, liquidation analyses, contract reviews, a default notice, litigation file organization, 2,000+ transaction expense reconciliation, engagement letters, wealth management checklists, data room management, and daily CRM updates. This isn't the future. It's right now. The world is changing. Keep up.#BusinessTurnaround #PrivateCredit #CCAA #Restructuring #RealEstate #AI #SinclairRange #Deals #Leadership #SmallBusiness
Transcribe →Sinclair Range Week in Review — March 6, 2026
Mar 600:36:47Tap to summarizeThis week we tackle two small business valuations, reveal how AI collapsed 30 hours of professional work into 90 minutes, and share a golden rule every investor needs to hear: you make your money on the buy.Interesting Deal / File of the Week: Valuing a Small BusinessWe were asked to provide valuation guidance on two small businesses for partner buyouts. We walk through the full professional process — from understanding the purpose, to analyzing financials, to writing a defensible 6–10 page letter — and why that work typically costs $5,000 to $10,000. Then we show how AI let us complete both valuation letters, with full schedules and methodology, in just 90 minutes. We also discuss the growing problem of non-professionals using AI to imitate professional work — and what that means for the industry.Lesson Learned of the Week: Buy Bank DebtWorking with a manufacturing client in financial distress, we break down why understanding liquidation value from the bank's perspective is critical to your negotiating position. We also explore an alternative deal structure: instead of refinancing the full loan, have a new lender buy out the existing bank's position at a discount — illustrated by a real acquisition where $3 million in debt was purchased for $1.5 million.What I'm Thinking About: Make Money on the BuyA golden rule for investors and entrepreneurs: your profit isn't made on the sale, and it isn't made on the value you add — your profit is made on the buy. We discuss why you should avoid competitive sale processes and instead create deals from a unique knowledge base. We reference a real debtor-in-possession lending example generating 50%+ annualized returns, first secured — the kind of deal no one hands you. You have to build it.#Business #Deals #Valuation #SmallBusiness #AI #PrivateCredit #BankDebt #Investing #Leadership #SinclairRange #WinningMomentum
Transcribe →Sinclair Range Week in Review – February 13, 2026
Feb 1300:32:43Tap to summarizeThis week at Sinclair Range, we catch up on the high-stakes drama and deals of 2026. From a $100 million private credit mandate to a "hostile takeover" attempt that required a 48-hour emergency rescue, we dive into the real-world grit of restructuring and transition.Interesting Deal / File of the Week: $100M Private Credit & Ontario MachiningWe went to market on a $100 million private credit offering for an established Canadian lender filling a $1.5 billion gap in the market. We also continue to market a precision machining firm in Ontario that is successfully pivoting into the aerospace sector following a challenging 2024.Lesson Learned: Mastering the PitchStop reading AI scripts and ditch the "fluff" (p. 4). We break down the essential hierarchy of a professional pitch: the 30-second "hook," the 3-minute "how," and the 10-minute "deal"—specifically how to get in, how to get out, and what happens in between.Struggle of the Week: The Rogue Contractor & The $2M SaveA raw look at a contractor who attempted a hostile takeover of a client during a CCAA filing. We detail the immediate contract termination, the subsequent $2 million financing collapse, and the emergency Sunday night rescue through Sapphire Global Investments.What I’m Thinking About: Underestimating the UpsideA personal musing on the "3-legged stool" of business, leadership, and self-improvement. We discuss why even seasoned advisors often underestimate their own brand potential and why maintaining positivity is a functional operating requirement for any leader.
Transcribe →Sinclair Range Week in Review – January 9, 2026
Jan 900:30:41Tap to summarizeThis week at Sinclair Range, we reflect on the power of persuasion-based thinking, lessons learned from dealmaking under stress, the realities of rebuilding momentum, and why admitting trouble is the first step to any real turnaround.• Tribute & Lessons from Scott AdamsWhy persuasion-based framing explains behavior better than surface facts, how incentives and framing make seemingly irrational decisions predictable, and why this skill is critical in business, leadership, and negotiations.• Persuasion as a Business SkillKey persuasion concepts including framing, attention, repetition, visualization, and reciprocity, and how understanding persuasion improves sales, dealmaking, and decision-making in complex environments.• Momentum Requires WorkA look at the physical and mental grind behind rebuilding a business, why changing momentum is not passive, and how discipline, hustle, positivity, and integrity form a simple but effective operating formula.• Interesting Deal / File of the WeekOverview of a new going-concern sale or financing mandate for a precision machining and plastic injection mold tooling company in Ontario, including sector exposure, recent operational challenges, improving cash flow, and growth momentum in aerospace.• Lesson Learned: Deals That Die at the NDAWhy prolonged negotiations over standard agreements are a leading indicator of deal failure, how decision paralysis kills distressed companies, and why availability of capital matters more than cost when survival is at stake.• Admitting Trouble as a Turning PointWhy true turnaround begins with honestly admitting the severity of a problem, how denial slows decision-making, and why acknowledging rock bottom frees leaders to act decisively.• Struggle of the WeekProgress update on completing the Pathway to Profit Academy, why it exists for founders not yet ready to hire Sinclair Range, and how finishing long-delayed projects is part of restoring momentum.• What I’m Thinking About: Momentum and DefenseA personal reflection on illness, loss of momentum, rebuilding from defense, and why stabilizing first creates the foundation for growth, expansion, acquisitions, and private credit deployment in 2026.#Business #Deals #Turnarounds #PrivateCredit #Leadership #Momentum #Persuasion #Capital #Restructuring #SinclairRange
Transcribe →Sinclair Range Week in Review – December 12, 2025
Dec 1200:42:45Tap to summarizeThis week at Sinclair Range, we break down how to properly evaluate investment performance, why benchmarks and mandates matter more than headline returns, and why private credit generates better returns than real estate.• How to Judge Investment Performance ProperlyWhy two portfolios with similar returns can be judged very differently depending on mandate, risk, and benchmarks.• Benchmarks, Risk, and the AI BubbleWhy today’s equity benchmarks are distorted by a handful of AI-driven stocks, how diversification hurts returns in bubbles, and what happens when those bubbles burst.• Knowledge Arbitrage in InvestingWhy true outperformance comes from information and experience, not risk, and how private credit rewards those who understand complex situations.• Passive Income vs Real ReturnsWhy real estate fund marketing often obscures true performance, how fees and structure compress returns, and why institutional capital is flooding into private credit.• Lesson Learned: Power in DistributionWhy having a better product isn’t enough, how margin follows power in the value chain, and why most businesses lose to distribution - unless they go direct-to-consumer.• Struggle of the WeekWhy investors sometimes make losses worse by trying to “work with” borrowers and when you must shift from solution provider to enforcement mindset.#Finance #Investing #PrivateCredit #Wealth #Benchmarks #CapitalAllocation #Restructuring #CCAA #DIPLoans #SinclairRange
Transcribe →Sinclair Range Week in Review – November 28, 2025
Nov 2800:39:19Tap to summarizeA big week at Sinclair Range, with our first Sapphire Global Finance deal closing, a deep dive into compounding vs “passive income,” and important lessons from real restructuring work across North America.Highlights:• Interesting Deal of the Week: Sapphire Global Finance Closes Its First DIP LoanSapphire has completed its first transaction — a highly secured DIP loan for a Canadian cannabis company entering CCAA protection. Scott explains why DIP financing pays high returns, how court-ordered super-priority works, and why Sinclair Range’s expertise creates value for borrowers and investors.• Wealth & Compounding: The Truth Behind Passive IncomeAfter reviewing Grant Cardone’s “abundance mindset” message, Scott breaks down why compounding — money, skills, network, health, talent stack — is the real engine of wealth creation, and why wasting money kills momentum.• Private Credit vs Real Estate FundsScott compares real-world returns:Cardone Capital IRR (~8%)S&P 500 (~14.9%)Private credit deals Sinclair Range is closing today, often multiples higher.He also outlines upcoming ways investors may gain access to private credit opportunities alongside Sinclair Range.• Lesson Learned: The Five Ways a Borrower Can Repay a LenderScott reviews the only five paths in any restructuring: refinance, cash flow, asset/equity sale, restructure, or liquidate — and why borrowers and lenders often lose sight of these fundamentals.• Startups & CapitalFounders must focus on mission, value creation, and execution — not just raising money. Scott highlights why capital follows traction and how The Inner Circle: Deals & Capital helps founders get feedback and clarity.#Finance #Investing #PrivateCredit #Compounding #Restructuring #Turnaround #DIPLoan #CCAA #CannabisBusiness #WealthBuilding #Entrepreneurship #SinclairRange #CapitalRaising
Transcribe →Sinclair Range Week in Review – November 7, 2025
Nov 700:32:31Tap to summarizeA huge week at Sinclair Range — from Elon Musk’s trillion-dollar pay package to real-world bridge loans, litigation, and market opportunities. Scott covers it all in this episode of Week in Review, where business, deals, and persuasion meet reality.Highlights:• Opening Commentary: Elon Musk’s $1 trillion Tesla pay package — what it really means, why it’s more persuasion than pay, and how outrageous anchoring works in business negotiations.• Lesson Learned of the Week: The five real ways a borrower can repay a lender. Forget the noise — Scott walks through the only options that actually exist, how companies get stuck, and what Sinclair Range sees in real debt restructuring work across North America.• Startups & Capital: Founders, stop confusing fundraising with execution. Why mission, business plans, and adding overwhelming value come before capital — and how The Inner Circle: Deals & Capital helps entrepreneurs get clarity, feedback, and traction.• Interesting Deal of the Week: Sinclair Range launches a $6 million Debtor-in-Possession (DIP) bridge loan in Alberta under CCAA protection — a fully secured, high-yield opportunity structured in investor-friendly tranches.• Struggles of the Week: Updates on Sinclair Range’s ongoing litigation with Ninepoint Partners, plus a new case with Zurn Elkay Water Solutions (NYSE: ZWS) — a U.S. industrial giant celebrated for sustainability, yet accused in court of failing cleanup obligations at a small Ontario site.• Musings of the Week: The massive $1-trillion-plus private debt market is booming. Scott explores how Sinclair Range is uniquely positioned in high-yield, secured turnaround lending — and whether it’s time to open co-investment opportunities for accredited investors.From persuasion and planning to private debt and litigation, this episode gives a candid look at how real deals get done — and what happens when they don’t.#Business #Finance #Investing #PrivateDebt #BridgeLoan #Restructuring #Turnaround #Leadership #Entrepreneurship #SinclairRange #TheInnerCircle #Capital #CCAA #Litigation #ZurnElkay #Ninepoint #Tesla #ElonMusk #Persuasion #Negotiation #Momentum #BusinessStrategy
Transcribe →Sinclair Range Week in Review – October 31, 2025
Oct 3100:31:34Tap to summarizeIt’s Halloween and a busy week at Sinclair Range. This episode includes the usual segments — Lessons Learned of the Week, Interesting Deal of the Week, and Struggles of the Week — with sharp insights into the real world of deals, debt, and capital.Highlights:• Inside look at The Inner Circle: Deals & Capital — Sinclair Range’s free, live biweekly community for founders, executives, and advisors. Next week’s meeting features a bridge loan pitch, a private debt lender, and a retired Air Force General discussing emerging warfare technology.• Lesson Learned: What is angel investing really? Scott breaks down the three major risk profiles — private debt, PE-style equity, and VC-style equity — and shares what works (and doesn’t) for individual investors.• Interesting Deal of the Week: Sinclair Range is arranging a 5 million dollar DIP financing for a premium and medical-grade cannabis producer in Alberta. Learn how the CCAA process, secured lending, and distressed debt intersect in this real-world turnaround story.• Struggles of the Week: Behind the scenes on Ninepoint Private Debt and its Canadian Senior Debt Fund — and why OPM Wire’s coverage caught Scott’s attention. Insight into fund-agent structures, liquidity issues, and Sinclair Range’s unique perspective from direct industry involvement and ongoing litigation.From angel investing and private debt to active restructuring mandates, this week’s episode dives deep into how real deals get made — and sometimes, how they go sideways.
Transcribe →Sinclair Range Week in Review – October 24, 2025
Oct 2400:19:59Tap to summarizeThis week, Scott takes a different approach — fewer files, more reflection. Amid chaos, tough negotiations, and constant bad news, he shares how The Power of Positive Thinking and the Winning Momentum methodology apply to both global events and business turnarounds.In this episode:• Why President Trump’s first-phase peace deal between Hamas and Israel is a master class in negotiation and turnarounds.• How Scott Adams describes Trump’s “reality distortion” as persuasion — and what leaders can learn from it.• Eric Trump’s surprising comment: “It was an excellent example of the power of positive thinking.”• The connection between Norman Vincent Peale’s 1952 classic The Power of Positive Thinking and the Trump family’s mindset — and why Scott is revisiting the book today.• Lessons from Peale that align with Sinclair Range’s Winning Momentum framework: recognizing “mental garbage,” replacing fear with focus, and manufacturing momentum through compounding wins.• Behind the scenes at Sinclair Range: weeks of chaos, collapsing deals, fraud discoveries, and constant bad news — and why Scott stopped reading negative updates.• The practical leadership takeaway:o Compress your “negative time” into a small daily window.o Focus the rest of your day on progress and value creation.o Find one thing to win at each day — because small wins compound into momentum.• How positivity, reframing, and focus bring order out of chaos — in business, leadership, and life.Quote of the Week:“You don’t have to be relentlessly positive — but you must not be negative. Negativity creates fear. Fear creates paralysis. Paralysis creates more negativity.”Join the conversation:If your company is in transition — growing fast, facing distress, or doing deals — reach out. Sinclair Range exists to help you navigate chaos and create momentum.
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